# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'J Rawson' 'Charlotte Alan' 'Delia Haynes' 'Christopher M. Pask' _publ_contact_author_name 'J Rawson' _publ_contact_author_email JMR31@CAM.AC.UK _publ_section_title ; Co-crystallisation of thiazyl radicals: Preparation and crystal structure of [PhCNSSN][C6F5CNSSN]. ; # Attachment 'cocrystal_paper.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 725685' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4-phenyl-1,2,3,5-dithiadiazolyl _chemical_formula_moiety 'C7 H5 N2 S2' _chemical_formula_sum 'C7 H5 N2 S2' _chemical_formula_weight 181.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 15.9893(4) _cell_length_b 32.8544(5) _cell_length_c 5.69680(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2992.64(10) _cell_formula_units_Z 16 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 47292 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.03 _exptl_crystal_description needle _exptl_crystal_colour green-black _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.609 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.635 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.931 _exptl_absorpt_correction_T_max 1.118 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_reflns_number 13393 _diffrn_reflns_av_R_equivalents 0.0981 _diffrn_reflns_av_sigmaI/netI 0.1037 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4656 _reflns_number_gt 3839 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution teXsan _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.0459P)^2^+0.7341P] 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 -0.04(9) _refine_ls_number_reflns 4656 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.0993 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 S21 S 0.14211(7) 0.82096(3) 0.0914(2) 0.0317(3) Uani 1 1 d . . . S22 S 0.09855(8) 0.83800(3) 0.4230(2) 0.0331(3) Uani 1 1 d . . . N21 N 0.1475(2) 0.86786(9) -0.0091(7) 0.0284(9) Uani 1 1 d . . . N22 N 0.0951(2) 0.88636(9) 0.3643(7) 0.0262(9) Uani 1 1 d . . . C21 C 0.1211(3) 0.89619(11) 0.1470(9) 0.0249(11) Uani 1 1 d . . . C22 C 0.1238(3) 0.93979(11) 0.0758(8) 0.0236(10) Uani 1 1 d . . . C23 C 0.1573(3) 0.95230(12) -0.1369(9) 0.0295(11) Uani 1 1 d . . . H23 H 0.1786 0.9327 -0.2437 0.035 Uiso 1 1 calc R . . C24 C 0.1597(3) 0.99315(12) -0.1947(9) 0.0357(12) Uani 1 1 d . . . H24 H 0.1845 1.0016 -0.3382 0.043 Uiso 1 1 calc R . . C25 C 0.1261(3) 1.02167(12) -0.0426(10) 0.0401(13) Uani 1 1 d . . . H25 H 0.1264 1.0497 -0.0837 0.048 Uiso 1 1 calc R . . C26 C 0.0923(3) 1.00960(13) 0.1664(10) 0.0427(14) Uani 1 1 d . . . H26 H 0.0691 1.0293 0.2694 0.051 Uiso 1 1 calc R . . C27 C 0.0915(3) 0.96864(12) 0.2304(9) 0.0355(13) Uani 1 1 d . . . H27 H 0.0691 0.9605 0.3776 0.043 Uiso 1 1 calc R . . S31 S -0.04495(8) 0.80970(3) -0.0678(2) 0.0355(3) Uani 1 1 d . . . S32 S -0.08254(8) 0.82192(3) 0.2761(2) 0.0326(3) Uani 1 1 d . . . N31 N -0.0537(2) 0.85613(9) -0.1589(7) 0.0230(9) Uani 1 1 d . . . N32 N -0.0975(2) 0.86989(10) 0.2302(7) 0.0305(10) Uani 1 1 d . . . C31 C -0.0813(3) 0.88248(12) 0.0142(9) 0.0280(11) Uani 1 1 d . . . C32 C -0.0950(3) 0.92622(11) -0.0441(9) 0.0255(11) Uani 1 1 d . . . C33 C -0.1373(3) 0.95109(12) 0.1136(9) 0.0306(11) Uani 1 1 d . . . H33 H -0.1568 0.9401 0.2579 0.037 Uiso 1 1 calc R . . C34 C -0.1510(3) 0.99145(12) 0.0621(10) 0.0379(13) Uani 1 1 d . . . H34 H -0.1801 1.0082 0.1710 0.046 Uiso 1 1 calc R . . C35 C -0.1230(3) 1.00773(13) -0.1462(10) 0.0410(14) Uani 1 1 d . . . H35 H -0.1320 1.0357 -0.1809 0.049 Uiso 1 1 calc R . . C36 C -0.0818(3) 0.98303(13) -0.3040(10) 0.0398(13) Uani 1 1 d . . . H36 H -0.0630 0.9941 -0.4486 0.048 Uiso 1 1 calc R . . C37 C -0.0674(3) 0.94256(12) -0.2559(9) 0.0308(12) Uani 1 1 d . . . H37 H -0.0389 0.9259 -0.3663 0.037 Uiso 1 1 calc R . . S11 S 0.36064(7) 0.80273(3) 0.1782(2) 0.0304(3) Uani 1 1 d . . . S12 S 0.31731(7) 0.77993(3) -0.1402(2) 0.0311(3) Uani 1 1 d . . . N11 N 0.4586(2) 0.80130(10) 0.1041(7) 0.0251(9) Uani 1 1 d . . . N12 N 0.4102(2) 0.77378(10) -0.2532(7) 0.0288(10) Uani 1 1 d . . . C11 C 0.4724(3) 0.78638(11) -0.1153(9) 0.0249(11) Uani 1 1 d . . . C12 C 0.5596(3) 0.78234(11) -0.2013(9) 0.0247(11) Uani 1 1 d . . . C13 C 0.5749(3) 0.76378(11) -0.4171(9) 0.0273(11) Uani 1 1 d . . . H13 H 0.5295 0.7534 -0.5068 0.033 Uiso 1 1 calc R . . C14 C 0.6553(3) 0.76041(12) -0.5009(9) 0.0350(13) Uani 1 1 d . . . H14 H 0.6654 0.7472 -0.6464 0.042 Uiso 1 1 calc R . . C15 C 0.7215(3) 0.77632(13) -0.3733(10) 0.0369(13) Uani 1 1 d . . . H15 H 0.7769 0.7744 -0.4326 0.044 Uiso 1 1 calc R . . C16 C 0.7066(3) 0.79513(13) -0.1575(10) 0.0375(13) Uani 1 1 d . . . H16 H 0.7517 0.8061 -0.0691 0.045 Uiso 1 1 calc R . . C17 C 0.6256(3) 0.79766(11) -0.0736(9) 0.0278(11) Uani 1 1 d . . . H17 H 0.6154 0.8101 0.0741 0.033 Uiso 1 1 calc R . . S41 S 0.30636(7) 0.86813(3) -0.3262(2) 0.0291(3) Uani 1 1 d . . . S42 S 0.33413(7) 0.88890(3) 0.0117(2) 0.0307(3) Uani 1 1 d . . . N41 N 0.4031(2) 0.87024(9) -0.4164(7) 0.0272(9) Uani 1 1 d . . . N42 N 0.4332(2) 0.89416(9) -0.0391(7) 0.0276(9) Uani 1 1 d . . . C41 C 0.4576(3) 0.88367(11) -0.2545(9) 0.0244(11) Uani 1 1 d . . . C42 C 0.5478(3) 0.88751(12) -0.3140(9) 0.0242(10) Uani 1 1 d . . . C43 C 0.5792(3) 0.87292(11) -0.5269(8) 0.0265(11) Uani 1 1 d . . . H43 H 0.5427 0.8614 -0.6405 0.032 Uiso 1 1 calc R . . C44 C 0.6642(3) 0.87539(12) -0.5702(9) 0.0313(11) Uani 1 1 d . . . H44 H 0.6860 0.8652 -0.7138 0.038 Uiso 1 1 calc R . . C45 C 0.7181(3) 0.89257(12) -0.4074(10) 0.0304(12) Uani 1 1 d . . . H45 H 0.7763 0.8940 -0.4394 0.036 Uiso 1 1 calc R . . C46 C 0.6870(3) 0.90769(13) -0.1985(10) 0.0343(12) Uani 1 1 d . . . H46 H 0.7235 0.9196 -0.0863 0.041 Uiso 1 1 calc R . . C47 C 0.6019(3) 0.90524(12) -0.1546(9) 0.0283(11) Uani 1 1 d . . . H47 H 0.5804 0.9160 -0.0121 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 S21 0.0324(7) 0.0259(6) 0.0368(9) -0.0003(5) 0.0078(7) 0.0022(5) S22 0.0428(7) 0.0294(6) 0.0269(8) 0.0024(5) -0.0018(7) -0.0011(5) N21 0.028(2) 0.0296(19) 0.027(3) -0.0014(17) 0.002(2) 0.0005(15) N22 0.036(2) 0.0218(17) 0.020(3) -0.0008(15) -0.002(2) -0.0028(15) C21 0.019(2) 0.029(2) 0.028(3) -0.0027(19) -0.003(2) 0.0007(17) C22 0.020(2) 0.026(2) 0.025(3) -0.0050(19) -0.003(2) -0.0011(17) C23 0.031(3) 0.034(2) 0.024(3) -0.002(2) 0.002(3) 0.0026(19) C24 0.046(3) 0.034(3) 0.028(3) 0.006(2) 0.004(3) -0.004(2) C25 0.058(3) 0.024(2) 0.038(4) 0.002(2) -0.003(3) -0.005(2) C26 0.061(4) 0.029(3) 0.039(4) -0.008(2) 0.007(3) 0.004(2) C27 0.051(3) 0.029(3) 0.027(3) -0.002(2) 0.009(3) -0.006(2) S31 0.0438(8) 0.0300(6) 0.0326(9) -0.0025(5) 0.0001(7) 0.0009(5) S32 0.0374(7) 0.0303(6) 0.0301(8) 0.0046(5) 0.0067(6) 0.0012(5) N31 0.029(2) 0.0214(17) 0.018(2) -0.0008(15) -0.0009(19) -0.0020(14) N32 0.030(2) 0.0297(19) 0.031(3) -0.0020(17) 0.010(2) 0.0008(16) C31 0.025(2) 0.033(2) 0.026(3) 0.003(2) 0.004(2) -0.0019(19) C32 0.023(2) 0.029(2) 0.025(3) -0.004(2) -0.005(2) -0.0034(18) C33 0.034(3) 0.033(2) 0.025(3) -0.001(2) -0.003(3) -0.005(2) C34 0.042(3) 0.031(3) 0.040(4) -0.008(2) 0.004(3) 0.007(2) C35 0.054(3) 0.023(2) 0.046(4) 0.003(2) -0.002(3) 0.003(2) C36 0.055(3) 0.034(3) 0.030(3) 0.009(2) 0.007(3) -0.002(2) C37 0.039(3) 0.032(3) 0.022(3) 0.000(2) 0.007(3) 0.000(2) S11 0.0309(7) 0.0388(6) 0.0214(8) -0.0009(5) 0.0019(6) -0.0021(5) S12 0.0275(6) 0.0339(6) 0.0320(8) -0.0057(5) -0.0005(6) -0.0033(5) N11 0.026(2) 0.0292(18) 0.020(2) 0.0030(16) 0.0010(19) 0.0011(15) N12 0.028(2) 0.0278(19) 0.030(3) -0.0072(16) -0.001(2) 0.0027(16) C11 0.032(3) 0.020(2) 0.023(3) 0.0010(19) 0.001(2) 0.0044(18) C12 0.026(3) 0.021(2) 0.027(3) 0.0066(19) 0.001(2) 0.0041(18) C13 0.032(3) 0.027(2) 0.024(3) 0.002(2) 0.000(3) 0.0020(19) C14 0.044(3) 0.032(2) 0.029(3) 0.008(2) 0.009(3) 0.008(2) C15 0.031(3) 0.034(3) 0.046(4) 0.016(2) 0.013(3) 0.008(2) C16 0.032(3) 0.036(2) 0.045(4) 0.007(2) 0.000(3) 0.004(2) C17 0.033(3) 0.030(2) 0.020(3) 0.0026(19) -0.001(2) 0.003(2) S41 0.0272(6) 0.0353(6) 0.0249(8) -0.0003(5) -0.0028(6) -0.0002(5) S42 0.0313(7) 0.0341(6) 0.0268(8) -0.0063(5) 0.0053(6) -0.0015(5) N41 0.028(2) 0.0339(19) 0.020(2) 0.0008(16) -0.002(2) -0.0021(16) N42 0.030(2) 0.0291(19) 0.024(3) -0.0054(16) -0.001(2) -0.0047(15) C41 0.034(3) 0.017(2) 0.022(3) 0.0031(18) 0.002(2) 0.0001(18) C42 0.026(2) 0.022(2) 0.024(3) 0.009(2) -0.003(2) 0.0016(18) C43 0.031(3) 0.030(2) 0.019(3) -0.0004(18) -0.001(2) -0.0010(19) C44 0.033(3) 0.036(2) 0.025(3) 0.007(2) 0.002(3) 0.001(2) C45 0.027(3) 0.031(2) 0.033(3) 0.006(2) 0.001(3) -0.0075(19) C46 0.029(3) 0.038(3) 0.035(4) 0.003(2) -0.004(3) -0.010(2) C47 0.034(3) 0.029(2) 0.022(3) -0.0004(18) 0.003(3) -0.0025(19) _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 S21 N21 1.646(3) . ? S21 S22 2.0899(18) . ? S22 N22 1.625(3) . ? N21 C21 1.354(5) . ? N22 C21 1.345(6) . ? C21 C22 1.490(6) . ? C22 C23 1.386(6) . ? C22 C27 1.394(6) . ? C23 C24 1.383(6) . ? C24 C25 1.385(7) . ? C25 C26 1.366(7) . ? C26 C27 1.394(6) . ? S31 N31 1.618(3) . ? S31 S32 2.0880(19) . ? S32 N32 1.615(3) . ? N31 C31 1.384(6) . ? N32 C31 1.324(6) . ? C31 C32 1.491(5) . ? C32 C33 1.390(6) . ? C32 C37 1.392(6) . ? C33 C34 1.376(6) . ? C34 C35 1.377(7) . ? C35 C36 1.379(7) . ? C36 C37 1.377(6) . ? S11 N11 1.623(4) . ? S11 S12 2.0814(18) . ? S12 N12 1.631(4) . ? N11 C11 1.361(6) . ? N12 C11 1.334(6) . ? C11 C12 1.484(6) . ? C12 C17 1.377(6) . ? C12 C13 1.394(7) . ? C13 C14 1.376(6) . ? C14 C15 1.387(7) . ? C15 C16 1.396(7) . ? C16 C17 1.383(6) . ? S41 N41 1.631(4) . ? S41 S42 2.0899(18) . ? S42 N42 1.620(4) . ? N41 C41 1.344(6) . ? N42 C41 1.333(6) . ? C41 C42 1.486(6) . ? C42 C47 1.384(6) . ? C42 C43 1.398(7) . ? C43 C44 1.384(6) . ? C44 C45 1.386(6) . ? C45 C46 1.383(7) . ? C46 C47 1.385(6) . ? 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 N21 S21 S22 94.65(14) . . ? N22 S22 S21 94.99(15) . . ? C21 N21 S21 113.5(3) . . ? C21 N22 S22 114.5(3) . . ? N22 C21 N21 122.4(4) . . ? N22 C21 C22 119.4(4) . . ? N21 C21 C22 118.2(4) . . ? C23 C22 C27 119.6(4) . . ? C23 C22 C21 122.3(4) . . ? C27 C22 C21 118.1(4) . . ? C24 C23 C22 120.4(4) . . ? C23 C24 C25 119.8(5) . . ? C26 C25 C24 120.2(4) . . ? C25 C26 C27 120.8(4) . . ? C22 C27 C26 119.2(5) . . ? N31 S31 S32 95.44(14) . . ? N32 S32 S31 94.50(16) . . ? C31 N31 S31 112.9(3) . . ? C31 N32 S32 115.2(3) . . ? N32 C31 N31 121.9(4) . . ? N32 C31 C32 118.7(4) . . ? N31 C31 C32 119.4(4) . . ? C33 C32 C37 119.2(4) . . ? C33 C32 C31 119.6(4) . . ? C37 C32 C31 121.2(4) . . ? C34 C33 C32 120.4(5) . . ? C33 C34 C35 120.4(4) . . ? C34 C35 C36 119.3(4) . . ? C37 C36 C35 121.2(5) . . ? C36 C37 C32 119.5(4) . . ? N11 S11 S12 94.83(15) . . ? N12 S12 S11 94.91(15) . . ? C11 N11 S11 113.9(3) . . ? C11 N12 S12 114.1(3) . . ? N12 C11 N11 122.1(4) . . ? N12 C11 C12 118.6(4) . . ? N11 C11 C12 119.2(4) . . ? C17 C12 C13 119.5(4) . . ? C17 C12 C11 120.9(4) . . ? C13 C12 C11 119.7(4) . . ? C14 C13 C12 120.3(5) . . ? C13 C14 C15 120.1(5) . . ? C14 C15 C16 119.9(5) . . ? C17 C16 C15 119.3(5) . . ? C12 C17 C16 120.9(5) . . ? N41 S41 S42 94.30(15) . . ? N42 S42 S41 94.48(16) . . ? C41 N41 S41 114.4(3) . . ? C41 N42 S42 115.0(3) . . ? N42 C41 N41 121.8(4) . . ? N42 C41 C42 118.1(4) . . ? N41 C41 C42 120.0(4) . . ? C47 C42 C43 119.2(4) . . ? C47 C42 C41 119.6(4) . . ? C43 C42 C41 121.2(4) . . ? C44 C43 C42 119.2(5) . . ? C43 C44 C45 121.0(5) . . ? C46 C45 C44 119.9(4) . . ? C45 C46 C47 119.2(5) . . ? C42 C47 C46 121.4(5) . . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.301 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.077 #=== END data_2 _database_code_depnum_ccdc_archive 'CCDC 725686' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4-perfluorophenyl-1,2,3,5-dithiadiazolyl _chemical_melting_point ? _chemical_formula_moiety 'C7 F5 N2 S2' _chemical_formula_sum 'C7 F5 N2 S2' _chemical_formula_weight 271.21 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' 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 monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.0888(2) _cell_length_b 10.6435(2) _cell_length_c 10.8530(1) _cell_angle_alpha 90.00 _cell_angle_beta 123.133(1) _cell_angle_gamma 90.00 _cell_volume 1749.76(4) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 10556 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 33.14 _exptl_crystal_description blocks _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.059 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.659 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.690 _exptl_absorpt_correction_T_max 0.841 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71070 _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_reflns_number 18088 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.71 _diffrn_reflns_theta_max 33.16 _reflns_number_total 3329 _reflns_number_gt 2952 _reflns_threshold_expression >2sigma(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, 1990)' _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^)+(0.0351P)^2^+1.1950P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3329 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0819 _refine_ls_wR_factor_gt 0.0787 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 S1 S 0.10985(2) 0.08935(2) 0.42756(3) 0.02501(7) Uani 1 1 d . . . S2 S 0.09152(2) 0.08613(2) 0.21980(3) 0.02461(7) Uani 1 1 d . . . N1 N 0.12186(7) -0.06293(9) 0.45111(10) 0.02392(18) Uani 1 1 d . . . N2 N 0.09859(7) -0.06670(9) 0.21539(11) 0.02316(17) Uani 1 1 d . . . F2 F 0.20895(5) -0.25500(7) 0.23508(9) 0.03273(17) Uani 1 1 d . . . F3 F 0.21922(5) -0.50448(7) 0.23174(9) 0.03293(17) Uani 1 1 d . . . F4 F 0.14624(6) -0.64960(7) 0.34338(11) 0.0415(2) Uani 1 1 d . . . F5 F 0.06074(6) -0.54169(8) 0.45756(9) 0.03499(17) Uani 1 1 d . . . F6 F 0.04915(5) -0.29179(7) 0.46433(8) 0.02930(15) Uani 1 1 d . . . C0 C 0.11483(7) -0.12348(10) 0.33733(11) 0.02015(18) Uani 1 1 d . . . C1 C 0.12704(7) -0.26191(9) 0.34719(11) 0.01986(17) Uani 1 1 d . . . C2 C 0.17074(7) -0.32135(10) 0.28981(12) 0.02186(18) Uani 1 1 d . . . C3 C 0.17781(7) -0.45092(10) 0.28881(12) 0.0240(2) Uani 1 1 d . . . C4 C 0.14118(8) -0.52488(10) 0.34640(13) 0.0265(2) Uani 1 1 d . . . C5 C 0.09870(8) -0.46929(10) 0.40633(13) 0.0245(2) Uani 1 1 d . . . C6 C 0.09281(7) -0.33968(10) 0.40798(11) 0.02125(18) 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 S1 0.03514(15) 0.01650(12) 0.02288(13) -0.00301(8) 0.01553(11) -0.00220(9) S2 0.03718(15) 0.01548(12) 0.02948(14) 0.00162(9) 0.02355(12) -0.00056(9) N1 0.0330(5) 0.0169(4) 0.0202(4) -0.0002(3) 0.0135(4) 0.0001(3) N2 0.0342(5) 0.0154(4) 0.0262(4) 0.0009(3) 0.0205(4) 0.0007(3) F2 0.0409(4) 0.0264(3) 0.0463(4) 0.0070(3) 0.0338(4) 0.0039(3) F3 0.0360(4) 0.0287(4) 0.0377(4) -0.0028(3) 0.0225(3) 0.0088(3) F4 0.0544(5) 0.0140(3) 0.0581(5) -0.0007(3) 0.0321(4) 0.0011(3) F5 0.0404(4) 0.0261(4) 0.0424(4) 0.0068(3) 0.0251(4) -0.0060(3) F6 0.0371(4) 0.0268(3) 0.0346(4) 0.0006(3) 0.0264(3) 0.0005(3) C0 0.0234(4) 0.0163(4) 0.0213(4) -0.0001(3) 0.0125(4) -0.0003(3) C1 0.0226(4) 0.0158(4) 0.0204(4) 0.0005(3) 0.0112(4) 0.0005(3) C2 0.0238(4) 0.0191(4) 0.0236(4) 0.0018(3) 0.0135(4) 0.0013(3) C3 0.0251(5) 0.0202(4) 0.0246(5) -0.0012(4) 0.0123(4) 0.0040(4) C4 0.0292(5) 0.0156(4) 0.0294(5) 0.0002(4) 0.0125(4) 0.0008(4) C5 0.0271(5) 0.0187(4) 0.0255(5) 0.0033(4) 0.0130(4) -0.0022(4) C6 0.0235(4) 0.0192(4) 0.0204(4) 0.0007(3) 0.0116(4) -0.0004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 N1 1.6367(10) . ? S1 S2 2.0925(4) . ? S1 S2 3.0755(4) 2 ? S2 N2 1.6344(10) . ? N1 C0 1.3360(13) . ? N2 C0 1.3334(13) . ? F2 C2 1.3333(12) . ? F3 C3 1.3331(13) . ? F4 C4 1.3323(13) . ? F5 C5 1.3387(13) . ? F6 C6 1.3363(12) . ? C0 C1 1.4850(14) . ? C1 C6 1.3966(14) . ? C1 C2 1.3968(14) . ? C2 C3 1.3856(15) . ? C3 C4 1.3792(17) . ? C4 C5 1.3819(17) . ? C5 C6 1.3845(15) . ? 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 N1 S1 S2 94.67(4) . . ? N1 S1 S2 95.08(4) . 2 ? S2 S1 S2 89.681(14) . 2 ? N2 S2 S1 94.53(4) . . ? C0 N1 S1 113.32(8) . . ? C0 N2 S2 113.61(8) . . ? N2 C0 N1 123.83(10) . . ? N2 C0 C1 117.69(9) . . ? N1 C0 C1 118.48(9) . . ? C6 C1 C2 116.57(9) . . ? C6 C1 C0 122.35(9) . . ? C2 C1 C0 121.02(9) . . ? F2 C2 C3 116.82(10) . . ? F2 C2 C1 121.08(9) . . ? C3 C2 C1 122.10(10) . . ? F3 C3 C4 119.85(10) . . ? F3 C3 C2 120.46(10) . . ? C4 C3 C2 119.69(10) . . ? F4 C4 C3 120.07(11) . . ? F4 C4 C5 120.10(11) . . ? C3 C4 C5 119.82(10) . . ? F5 C5 C4 119.50(10) . . ? F5 C5 C6 120.50(10) . . ? C4 C5 C6 119.95(10) . . ? F6 C6 C5 117.06(9) . . ? F6 C6 C1 121.05(9) . . ? C5 C6 C1 121.82(10) . . ? 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 N1 S1 S2 N2 1.42(5) . . . . ? S2 S1 S2 N2 -93.65(4) 2 . . . ? S2 S1 N1 C0 -0.62(8) . . . . ? S2 S1 N1 C0 89.47(8) 2 . . . ? S1 S2 N2 C0 -2.00(8) . . . . ? S2 N2 C0 N1 2.15(15) . . . . ? S2 N2 C0 C1 -176.91(8) . . . . ? S1 N1 C0 N2 -0.77(15) . . . . ? S1 N1 C0 C1 178.28(8) . . . . ? N2 C0 C1 C6 -140.21(11) . . . . ? N1 C0 C1 C6 40.68(15) . . . . ? N2 C0 C1 C2 37.09(15) . . . . ? N1 C0 C1 C2 -142.02(11) . . . . ? C6 C1 C2 F2 -177.12(10) . . . . ? C0 C1 C2 F2 5.42(16) . . . . ? C6 C1 C2 C3 1.86(16) . . . . ? C0 C1 C2 C3 -175.59(10) . . . . ? F2 C2 C3 F3 -1.67(16) . . . . ? C1 C2 C3 F3 179.30(10) . . . . ? F2 C2 C3 C4 178.78(10) . . . . ? C1 C2 C3 C4 -0.25(17) . . . . ? F3 C3 C4 F4 -0.81(17) . . . . ? C2 C3 C4 F4 178.74(10) . . . . ? F3 C3 C4 C5 179.62(10) . . . . ? C2 C3 C4 C5 -0.82(17) . . . . ? F4 C4 C5 F5 -1.79(17) . . . . ? C3 C4 C5 F5 177.78(10) . . . . ? F4 C4 C5 C6 -179.36(10) . . . . ? C3 C4 C5 C6 0.20(17) . . . . ? F5 C5 C6 F6 0.93(15) . . . . ? C4 C5 C6 F6 178.48(10) . . . . ? F5 C5 C6 C1 -176.02(10) . . . . ? C4 C5 C6 C1 1.53(17) . . . . ? C2 C1 C6 F6 -179.33(9) . . . . ? C0 C1 C6 F6 -1.91(16) . . . . ? C2 C1 C6 C5 -2.50(15) . . . . ? C0 C1 C6 C5 174.92(10) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 33.16 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.423 _refine_diff_density_min -0.498 _refine_diff_density_rms 0.080 #=== END data_3 _database_code_depnum_ccdc_archive 'CCDC 725687' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; (4-phenyl-1,2,3,5-dithiadiazolyl) (4-perfluorophenyl-1,2,3,5-dithiadiazolyl) co-crystal ; _chemical_melting_point ? _chemical_formula_moiety '(C7 H5 N2 S2), (C7 F5 N2 S2) ' _chemical_formula_sum 'C14 H5 F5 N4 S4' _chemical_formula_weight 452.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.3529(2) _cell_length_b 11.7748(2) _cell_length_c 12.2261(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.0280(10) _cell_angle_gamma 90.00 _cell_volume 1628.07(5) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 22608 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 32.03 _exptl_crystal_description plates _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.846 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.646 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.833 _exptl_absorpt_correction_T_max 0.931 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71070 _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 scan' _diffrn_reflns_number 31078 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 32.07 _reflns_number_total 5665 _reflns_number_gt 4107 _reflns_threshold_expression >2sigma(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, 1990)' _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^)+(0.0408P)^2^+0.7632P] 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 5665 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1002 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 S12 S 0.64422(4) 1.14819(4) 0.20859(4) 0.03462(11) Uani 1 1 d . . . S11 S 0.61552(4) 1.17122(4) 0.37422(4) 0.03495(11) Uani 1 1 d . . . N12 N 0.74996(12) 1.05603(13) 0.23370(12) 0.0322(3) Uani 1 1 d . . . N11 N 0.71859(13) 1.08234(13) 0.41903(12) 0.0330(3) Uani 1 1 d . . . C10 C 0.77593(13) 1.03408(14) 0.34010(13) 0.0269(3) Uani 1 1 d . . . C11 C 0.87289(13) 0.95255(14) 0.37192(13) 0.0272(3) Uani 1 1 d . . . C12 C 0.88415(14) 0.89908(15) 0.47403(14) 0.0302(3) Uani 1 1 d . . . F12 F 0.80791(10) 0.91861(10) 0.54918(8) 0.0400(3) Uani 1 1 d . . . C13 C 0.97315(16) 0.82221(15) 0.50359(15) 0.0345(4) Uani 1 1 d . . . F13 F 0.97880(11) 0.77330(11) 0.60212(10) 0.0520(3) Uani 1 1 d . . . C14 C 1.05618(15) 0.79690(16) 0.43152(16) 0.0362(4) Uani 1 1 d . . . F14 F 1.14134(10) 0.72113(11) 0.45913(11) 0.0527(3) Uani 1 1 d . . . C15 C 1.05005(15) 0.84994(16) 0.33123(16) 0.0348(4) Uani 1 1 d . . . F15 F 1.13258(10) 0.82954(11) 0.26146(10) 0.0490(3) Uani 1 1 d . . . C16 C 0.95939(14) 0.92506(15) 0.30168(14) 0.0298(3) Uani 1 1 d . . . F16 F 0.95906(9) 0.97248(10) 0.20182(9) 0.0411(3) Uani 1 1 d . . . S21 S 0.41762(4) 0.99315(4) 0.34967(4) 0.03502(11) Uani 1 1 d . . . S22 S 0.45310(4) 0.96438(4) 0.18759(4) 0.03344(11) Uani 1 1 d . . . N21 N 0.50828(13) 0.89532(13) 0.40053(11) 0.0311(3) Uani 1 1 d . . . N22 N 0.54874(12) 0.86293(12) 0.21828(11) 0.0291(3) Uani 1 1 d . . . C20 C 0.56562(13) 0.84026(13) 0.32600(12) 0.0243(3) Uani 1 1 d . . . C21 C 0.64994(13) 0.74888(13) 0.36229(12) 0.0243(3) Uani 1 1 d . . . C22 C 0.65445(14) 0.70632(14) 0.46906(13) 0.0278(3) Uani 1 1 d . . . H22 H 0.6025 0.7355 0.5191 0.033 Uiso 1 1 calc R . . C23 C 0.73441(15) 0.62168(15) 0.50246(14) 0.0325(3) Uani 1 1 d . . . H23 H 0.7370 0.5928 0.5752 0.039 Uiso 1 1 calc R . . C24 C 0.81092(16) 0.57894(15) 0.42976(15) 0.0347(4) Uani 1 1 d . . . H24 H 0.8660 0.5212 0.4528 0.042 Uiso 1 1 calc R . . C25 C 0.80657(15) 0.62096(16) 0.32332(14) 0.0328(4) Uani 1 1 d . . . H25 H 0.8587 0.5915 0.2736 0.039 Uiso 1 1 calc R . . C26 C 0.72660(14) 0.70565(14) 0.28907(13) 0.0278(3) Uani 1 1 d . . . H26 H 0.7240 0.7341 0.2162 0.033 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 S12 0.0306(2) 0.0343(2) 0.0390(2) 0.00932(18) 0.00363(17) 0.00437(16) S11 0.0355(2) 0.0294(2) 0.0396(2) -0.00326(17) 0.00099(17) 0.00867(17) N12 0.0276(7) 0.0349(8) 0.0341(7) 0.0031(6) 0.0032(6) 0.0038(6) N11 0.0334(7) 0.0306(8) 0.0344(7) -0.0046(6) -0.0010(6) 0.0083(6) C10 0.0231(7) 0.0250(7) 0.0326(8) -0.0015(6) 0.0018(6) -0.0012(5) C11 0.0228(7) 0.0244(7) 0.0338(8) -0.0047(6) -0.0012(6) -0.0008(6) C12 0.0280(8) 0.0306(8) 0.0316(8) -0.0048(6) -0.0002(6) 0.0001(6) F12 0.0427(6) 0.0453(7) 0.0325(5) 0.0011(5) 0.0062(4) 0.0078(5) C13 0.0367(9) 0.0304(9) 0.0346(9) -0.0010(7) -0.0072(7) 0.0031(7) F13 0.0602(8) 0.0520(8) 0.0417(6) 0.0081(5) -0.0075(5) 0.0133(6) C14 0.0293(8) 0.0301(9) 0.0472(10) -0.0078(8) -0.0081(7) 0.0068(6) F14 0.0442(6) 0.0459(7) 0.0654(8) -0.0068(6) -0.0108(6) 0.0202(5) C15 0.0234(7) 0.0348(9) 0.0460(10) -0.0115(8) 0.0024(7) 0.0003(6) F15 0.0308(5) 0.0579(8) 0.0590(7) -0.0121(6) 0.0082(5) 0.0072(5) C16 0.0239(7) 0.0309(8) 0.0343(8) -0.0030(7) 0.0013(6) -0.0033(6) F16 0.0319(5) 0.0511(7) 0.0413(6) 0.0050(5) 0.0090(4) 0.0002(5) S21 0.0315(2) 0.0351(2) 0.0397(2) 0.00448(18) 0.00999(17) 0.00943(17) S22 0.0340(2) 0.0323(2) 0.0327(2) 0.00181(17) -0.00487(16) 0.00538(16) N21 0.0332(7) 0.0306(7) 0.0305(7) 0.0030(6) 0.0087(6) 0.0067(6) N22 0.0320(7) 0.0289(7) 0.0255(6) -0.0017(5) -0.0026(5) 0.0049(5) C20 0.0236(7) 0.0235(7) 0.0257(7) -0.0001(6) 0.0020(5) -0.0021(5) C21 0.0250(7) 0.0234(7) 0.0241(7) -0.0013(5) 0.0003(5) -0.0011(5) C22 0.0303(8) 0.0295(8) 0.0238(7) -0.0007(6) 0.0033(6) 0.0008(6) C23 0.0368(9) 0.0323(9) 0.0276(8) 0.0041(6) -0.0019(6) 0.0004(7) C24 0.0336(8) 0.0304(9) 0.0387(9) 0.0002(7) -0.0048(7) 0.0059(7) C25 0.0325(8) 0.0332(9) 0.0329(8) -0.0042(7) 0.0031(7) 0.0065(7) C26 0.0295(8) 0.0290(8) 0.0249(7) -0.0011(6) 0.0024(6) 0.0017(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S12 N12 1.6274(15) . ? S12 S11 2.0967(7) . ? S11 N11 1.6286(14) . ? N12 C10 1.334(2) . ? N11 C10 1.337(2) . ? C10 C11 1.487(2) . ? C11 C12 1.394(2) . ? C11 C16 1.398(2) . ? C12 F12 1.3362(19) . ? C12 C13 1.381(2) . ? C13 F13 1.332(2) . ? C13 C14 1.378(3) . ? C14 F14 1.3370(19) . ? C14 C15 1.372(3) . ? C15 F15 1.343(2) . ? C15 C16 1.381(2) . ? C16 F16 1.342(2) . ? S21 N21 1.6311(15) . ? S21 S22 2.0842(6) . ? S22 N22 1.6356(14) . ? N21 C20 1.334(2) . ? N22 C20 1.341(2) . ? C20 C21 1.482(2) . ? C21 C22 1.395(2) . ? C21 C26 1.398(2) . ? C22 C23 1.385(2) . ? C22 H22 0.9500 . ? C23 C24 1.390(3) . ? C23 H23 0.9500 . ? C24 C25 1.389(2) . ? C24 H24 0.9500 . ? C25 C26 1.388(2) . ? C25 H25 0.9500 . ? C26 H26 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 N12 S12 S11 94.51(6) . . ? N11 S11 S12 94.24(6) . . ? C10 N12 S12 114.18(12) . . ? C10 N11 S11 114.28(12) . . ? N12 C10 N11 122.80(15) . . ? N12 C10 C11 118.41(14) . . ? N11 C10 C11 118.80(14) . . ? C12 C11 C16 115.55(15) . . ? C12 C11 C10 122.26(15) . . ? C16 C11 C10 122.19(15) . . ? F12 C12 C13 115.85(15) . . ? F12 C12 C11 121.60(15) . . ? C13 C12 C11 122.55(16) . . ? F13 C13 C14 120.23(16) . . ? F13 C13 C12 119.76(17) . . ? C14 C13 C12 120.01(17) . . ? F14 C14 C15 120.55(17) . . ? F14 C14 C13 120.19(18) . . ? C15 C14 C13 119.26(16) . . ? F15 C15 C14 120.17(16) . . ? F15 C15 C16 119.59(17) . . ? C14 C15 C16 120.24(16) . . ? F16 C16 C15 116.56(15) . . ? F16 C16 C11 121.09(15) . . ? C15 C16 C11 122.35(16) . . ? N21 S21 S22 94.56(5) . . ? N22 S22 S21 94.61(5) . . ? C20 N21 S21 114.36(12) . . ? C20 N22 S22 113.93(11) . . ? N21 C20 N22 122.54(15) . . ? N21 C20 C21 119.31(14) . . ? N22 C20 C21 118.13(13) . . ? C22 C21 C26 119.64(15) . . ? C22 C21 C20 120.71(14) . . ? C26 C21 C20 119.65(14) . . ? C23 C22 C21 120.24(15) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C24 120.12(15) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C25 C24 C23 119.81(16) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C26 C25 C24 120.46(16) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C25 C26 C21 119.72(15) . . ? C25 C26 H26 120.1 . . ? C21 C26 H26 120.1 . . ? 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 N12 S12 S11 N11 0.37(8) . . . . ? S11 S12 N12 C10 -0.76(13) . . . . ? S12 S11 N11 C10 0.07(13) . . . . ? S12 N12 C10 N11 1.0(2) . . . . ? S12 N12 C10 C11 -178.88(11) . . . . ? S11 N11 C10 N12 -0.7(2) . . . . ? S11 N11 C10 C11 179.24(12) . . . . ? N12 C10 C11 C12 -160.74(16) . . . . ? N11 C10 C11 C12 19.3(2) . . . . ? N12 C10 C11 C16 19.8(2) . . . . ? N11 C10 C11 C16 -160.18(16) . . . . ? C16 C11 C12 F12 179.45(14) . . . . ? C10 C11 C12 F12 -0.1(2) . . . . ? C16 C11 C12 C13 -1.3(2) . . . . ? C10 C11 C12 C13 179.18(15) . . . . ? F12 C12 C13 F13 -0.2(2) . . . . ? C11 C12 C13 F13 -179.54(16) . . . . ? F12 C12 C13 C14 -179.81(16) . . . . ? C11 C12 C13 C14 0.9(3) . . . . ? F13 C13 C14 F14 1.5(3) . . . . ? C12 C13 C14 F14 -178.90(16) . . . . ? F13 C13 C14 C15 -178.73(16) . . . . ? C12 C13 C14 C15 0.8(3) . . . . ? F14 C14 C15 F15 -2.7(3) . . . . ? C13 C14 C15 F15 177.59(16) . . . . ? F14 C14 C15 C16 177.67(15) . . . . ? C13 C14 C15 C16 -2.1(3) . . . . ? F15 C15 C16 F16 1.0(2) . . . . ? C14 C15 C16 F16 -179.36(15) . . . . ? F15 C15 C16 C11 -177.99(15) . . . . ? C14 C15 C16 C11 1.7(3) . . . . ? C12 C11 C16 F16 -178.92(14) . . . . ? C10 C11 C16 F16 0.6(2) . . . . ? C12 C11 C16 C15 0.0(2) . . . . ? C10 C11 C16 C15 179.55(15) . . . . ? N21 S21 S22 N22 -0.15(8) . . . . ? S22 S21 N21 C20 0.45(13) . . . . ? S21 S22 N22 C20 -0.17(12) . . . . ? S21 N21 C20 N22 -0.7(2) . . . . ? S21 N21 C20 C21 -179.62(11) . . . . ? S22 N22 C20 N21 0.6(2) . . . . ? S22 N22 C20 C21 179.48(11) . . . . ? N21 C20 C21 C22 11.5(2) . . . . ? N22 C20 C21 C22 -167.46(15) . . . . ? N21 C20 C21 C26 -167.88(15) . . . . ? N22 C20 C21 C26 13.2(2) . . . . ? C26 C21 C22 C23 0.0(2) . . . . ? C20 C21 C22 C23 -179.37(15) . . . . ? C21 C22 C23 C24 0.2(3) . . . . ? C22 C23 C24 C25 -0.3(3) . . . . ? C23 C24 C25 C26 0.2(3) . . . . ? C24 C25 C26 C21 0.0(3) . . . . ? C22 C21 C26 C25 -0.1(2) . . . . ? C20 C21 C26 C25 179.26(15) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 32.07 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.345 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.065