# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_i2emimtfsa _audit_creation_method SHELXL-97 _chemical_name_systematic '4,5-diiodo-1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl)amide' _chemical_name_common ? _chemical_formula_moiety 'C6 H9 N2 I2, C2 F6 N1 O4 S2' _chemical_formula_sum 'C8 H9 F6 I2 N3 O4 S2' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour colourless _diffrn_ambient_temperature 173 _chemical_formula_weight 643.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_int_tables_number 61 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.2841(4) _cell_length_b 16.1160(8) _cell_length_c 26.3361(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3516.0(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173 _cell_measurement_reflns_used 2977 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 25.87 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2416 _exptl_absorpt_coefficient_mu 3.895 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5927 _exptl_absorpt_correction_T_max 0.8291 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 18783 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 28.56 _reflns_number_total 4197 _reflns_number_gt 3156 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0302P)^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 4197 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0466 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0704 _refine_ls_wR_factor_gt 0.0654 _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 C8 C 0.1503(4) 0.9786(2) 0.18665(13) 0.0313(8) Uani 1 1 d . . . N2 N 0.6108(3) 0.76508(15) 0.09565(10) 0.0234(6) Uani 1 1 d . . . I1 I 0.73013(3) 0.698838(15) -0.006334(10) 0.03365(8) Uani 1 1 d . . . I2 I 0.76588(3) 0.941231(14) -0.011993(9) 0.03118(8) Uani 1 1 d . . . S2 S 0.10171(10) 0.92755(5) 0.12642(3) 0.02313(18) Uani 1 1 d . . . O4 O 0.2563(3) 0.91067(14) 0.10401(9) 0.0300(6) Uani 1 1 d . . . N3 N -0.0026(3) 0.85013(15) 0.13988(10) 0.0258(6) Uani 1 1 d . . . S1 S 0.06633(10) 0.76144(5) 0.15526(3) 0.0265(2) Uani 1 1 d . . . O3 O 0.0016(3) 0.98730(13) 0.10175(8) 0.0334(6) Uani 1 1 d . . . O2 O 0.2355(3) 0.75775(14) 0.16488(9) 0.0348(6) Uani 1 1 d . . . O1 O -0.0077(4) 0.69861(13) 0.12521(10) 0.0419(7) Uani 1 1 d . . . F5 F 0.0179(3) 0.99518(13) 0.21293(8) 0.0491(6) Uani 1 1 d . . . N1 N 0.6290(3) 0.89901(14) 0.09252(9) 0.0192(6) Uani 1 1 d . . . C3 C 0.6857(4) 0.86852(19) 0.04657(11) 0.0206(7) Uani 1 1 d . . . C1 C 0.5848(4) 0.83458(18) 0.12093(12) 0.0224(7) Uani 1 1 d . . . H1 H 0.5414 0.8381 0.1542 0.027 Uiso 1 1 calc R . . C5 C 0.6167(4) 0.98686(18) 0.10747(12) 0.0252(7) Uani 1 1 d . . . H5A H 0.5131 1.0097 0.0950 0.030 Uiso 1 1 calc R . . H5B H 0.7052 1.0185 0.0912 0.030 Uiso 1 1 calc R . . C2 C 0.6751(4) 0.78415(19) 0.04864(12) 0.0223(7) Uani 1 1 d . . . C7 C -0.0310(4) 0.7499(2) 0.21719(13) 0.0326(8) Uani 1 1 d . . . F3 F 0.0086(3) 0.80965(12) 0.24914(7) 0.0414(6) Uani 1 1 d . . . F1 F 0.0129(3) 0.67793(12) 0.23805(8) 0.0506(6) Uani 1 1 d . . . C4 C 0.5748(5) 0.68108(17) 0.11523(14) 0.0325(9) Uani 1 1 d . . . H4A H 0.5154 0.6856 0.1473 0.049 Uiso 1 1 calc R . . H4B H 0.6760 0.6510 0.1210 0.049 Uiso 1 1 calc R . . H4C H 0.5091 0.6509 0.0904 0.049 Uiso 1 1 calc R . . F4 F 0.2456(2) 0.93168(12) 0.21542(8) 0.0392(5) Uani 1 1 d . . . F6 F 0.2269(3) 1.04928(12) 0.17727(9) 0.0494(6) Uani 1 1 d . . . F2 F -0.1902(3) 0.74922(16) 0.21196(8) 0.0554(7) Uani 1 1 d . . . C6 C 0.6259(5) 0.9980(2) 0.16386(12) 0.0351(9) Uani 1 1 d . . . H6A H 0.5338 0.9703 0.1799 0.053 Uiso 1 1 calc R . . H6B H 0.6235 1.0573 0.1720 0.053 Uiso 1 1 calc R . . H6C H 0.7266 0.9737 0.1765 0.053 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 C8 0.029(2) 0.032(2) 0.032(2) 0.0009(16) -0.0013(16) -0.0001(17) N2 0.0240(15) 0.0198(14) 0.0264(15) 0.0036(11) 0.0010(12) -0.0021(12) I1 0.03638(15) 0.02976(14) 0.03482(16) -0.01153(10) 0.00562(10) -0.00416(11) I2 0.04066(16) 0.03083(14) 0.02206(14) 0.00523(9) 0.00270(10) -0.00721(10) S2 0.0231(4) 0.0265(4) 0.0198(4) 0.0019(3) -0.0008(3) -0.0005(4) O4 0.0273(14) 0.0329(13) 0.0297(14) -0.0019(11) 0.0088(10) -0.0030(11) N3 0.0239(15) 0.0265(14) 0.0271(15) 0.0049(12) -0.0018(12) -0.0004(13) S1 0.0268(5) 0.0253(4) 0.0274(4) 0.0016(4) 0.0019(4) -0.0012(4) O3 0.0346(14) 0.0325(13) 0.0332(14) 0.0125(11) -0.0081(11) 0.0038(12) O2 0.0265(14) 0.0334(14) 0.0446(16) 0.0059(12) 0.0030(11) 0.0050(11) O1 0.0582(19) 0.0311(13) 0.0365(15) -0.0058(11) -0.0019(13) -0.0119(14) F5 0.0411(14) 0.0685(16) 0.0377(13) -0.0212(11) 0.0068(10) 0.0060(12) N1 0.0170(14) 0.0195(13) 0.0210(14) -0.0017(11) -0.0004(11) 0.0004(11) C3 0.0190(17) 0.0273(17) 0.0156(16) 0.0015(13) -0.0023(12) -0.0002(14) C1 0.0240(18) 0.0230(16) 0.0201(17) 0.0002(13) 0.0003(13) -0.0028(14) C5 0.0262(18) 0.0198(16) 0.0295(19) 0.0007(14) 0.0017(14) -0.0021(14) C2 0.0219(17) 0.0230(17) 0.0219(17) -0.0007(13) -0.0002(13) -0.0034(14) C7 0.028(2) 0.038(2) 0.031(2) 0.0086(17) -0.0015(16) -0.0062(17) F3 0.0518(15) 0.0447(13) 0.0276(12) -0.0014(9) 0.0013(11) -0.0031(11) F1 0.0701(18) 0.0395(13) 0.0421(14) 0.0183(10) -0.0017(12) -0.0067(12) C4 0.039(2) 0.0176(16) 0.041(2) 0.0052(15) 0.0030(18) -0.0049(15) F4 0.0407(14) 0.0467(13) 0.0301(12) 0.0011(9) -0.0115(9) -0.0032(10) F6 0.0610(17) 0.0320(12) 0.0552(16) -0.0054(10) -0.0090(12) -0.0135(11) F2 0.0294(13) 0.0961(19) 0.0407(14) 0.0131(13) 0.0040(10) -0.0157(13) C6 0.039(2) 0.035(2) 0.031(2) -0.0075(15) 0.0006(17) -0.0010(17) _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 C8 F5 1.324(4) . ? C8 F6 1.328(4) . ? C8 F4 1.330(4) . ? C8 S2 1.831(4) . ? N2 C1 1.321(4) . ? N2 C2 1.382(4) . ? N2 C4 1.479(3) . ? I1 C2 2.048(3) . ? I2 C3 2.048(3) . ? S2 O3 1.427(2) . ? S2 O4 1.436(2) . ? S2 N3 1.559(3) . ? N3 S1 1.592(3) . ? S1 O1 1.424(2) . ? S1 O2 1.425(2) . ? S1 C7 1.829(4) . ? N1 C1 1.331(4) . ? N1 C3 1.388(4) . ? N1 C5 1.473(4) . ? C3 C2 1.364(4) . ? C1 H1 0.9500 . ? C5 C6 1.498(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C7 F3 1.321(4) . ? C7 F2 1.327(4) . ? C7 F1 1.333(4) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F5 C8 F6 108.6(3) . . ? F5 C8 F4 108.0(3) . . ? F6 C8 F4 108.0(3) . . ? F5 C8 S2 111.2(2) . . ? F6 C8 S2 109.2(2) . . ? F4 C8 S2 111.6(2) . . ? C1 N2 C2 109.0(2) . . ? C1 N2 C4 124.6(3) . . ? C2 N2 C4 126.4(3) . . ? O3 S2 O4 117.32(14) . . ? O3 S2 N3 108.75(15) . . ? O4 S2 N3 115.86(14) . . ? O3 S2 C8 102.64(15) . . ? O4 S2 C8 104.19(16) . . ? N3 S2 C8 106.50(15) . . ? S2 N3 S1 125.30(18) . . ? O1 S1 O2 119.50(16) . . ? O1 S1 N3 110.03(15) . . ? O2 S1 N3 115.82(15) . . ? O1 S1 C7 103.49(16) . . ? O2 S1 C7 105.70(15) . . ? N3 S1 C7 99.24(15) . . ? C1 N1 C3 107.9(2) . . ? C1 N1 C5 125.5(2) . . ? C3 N1 C5 126.6(2) . . ? C2 C3 N1 107.2(3) . . ? C2 C3 I2 128.4(2) . . ? N1 C3 I2 124.3(2) . . ? N2 C1 N2 109.5(3) . . ? N2 C1 H1 125.3 . . ? N1 C1 H1 125.3 . . ? N1 C5 C6 112.1(2) . . ? N1 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? N1 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C3 C2 N2 106.4(3) . . ? C3 C2 I1 128.8(2) . . ? N2 C2 I1 124.7(2) . . ? F3 C7 F2 108.6(3) . . ? F3 C7 F1 107.7(3) . . ? F2 C7 F1 107.9(3) . . ? F3 C7 S1 112.6(2) . . ? F2 C7 S1 110.3(2) . . ? F1 C7 S1 109.6(2) . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? 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 F5 C8 S2 O3 59.7(3) . . . . ? F6 C8 S2 O3 -60.2(3) . . . . ? F4 C8 S2 O3 -179.6(2) . . . . ? F5 C8 S2 O4 -177.5(2) . . . . ? F6 C8 S2 O4 62.6(3) . . . . ? F4 C8 S2 O4 -56.8(3) . . . . ? F5 C8 S2 N3 -54.5(3) . . . . ? F6 C8 S2 N3 -174.4(2) . . . . ? F4 C8 S2 N3 66.2(3) . . . . ? O3 S2 N3 S1 164.43(19) . . . . ? O4 S2 N3 S1 29.7(3) . . . . ? C8 S2 N3 S1 -85.6(2) . . . . ? S2 N3 S1 O1 -129.1(2) . . . . ? S2 N3 S1 O2 10.3(3) . . . . ? S2 N3 S1 C7 122.8(2) . . . . ? C1 N1 C3 C2 -0.4(3) . . . . ? C5 N1 C3 C2 -179.6(3) . . . . ? C1 N1 C3 I2 178.9(2) . . . . ? C5 N1 C3 I2 -0.3(4) . . . . ? C2 N2 C1 N1 0.1(4) . . . . ? C4 N2 C1 N1 -179.5(3) . . . . ? C3 N1 C1 N2 0.2(4) . . . . ? C5 N1 C1 N2 179.3(3) . . . . ? C1 N1 C5 C6 27.6(4) . . . . ? C3 N1 C5 C6 -153.4(3) . . . . ? N1 C3 C2 N2 0.5(3) . . . . ? I2 C3 C2 N2 -178.8(2) . . . . ? N1 C3 C2 I1 177.8(2) . . . . ? I2 C3 C2 I1 -1.5(4) . . . . ? C1 N2 C2 C3 -0.4(4) . . . . ? C4 N2 C2 C3 179.2(3) . . . . ? C1 N2 C2 I1 -177.8(2) . . . . ? C4 N2 C2 I1 1.8(5) . . . . ? O1 S1 C7 F3 -172.6(2) . . . . ? O2 S1 C7 F3 61.0(3) . . . . ? N3 S1 C7 F3 -59.3(3) . . . . ? O1 S1 C7 F2 -51.1(3) . . . . ? O2 S1 C7 F2 -177.5(2) . . . . ? N3 S1 C7 F2 62.2(3) . . . . ? O1 S1 C7 F1 67.5(3) . . . . ? O2 S1 C7 F1 -58.9(3) . . . . ? N3 S1 C7 F1 -179.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.429 _refine_diff_density_min -1.117 _refine_diff_density_rms 0.124 _database_code_depnum_ccdc_archive 'CCDC 763036' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_br2emimtfsi _audit_creation_method SHELXL-97 _chemical_name_systematic '4,5-dibromo-1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide' _chemical_name_common ? _chemical_formula_moiety 'C6 H9 N2 Br2, C2 N1 O4 F6 S2' _chemical_formula_sum 'C8 H9 Br2 F6 N3 O4 S2' _chemical_melting_point ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _diffrn_ambient_temperature 173 _chemical_formula_weight 549.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 9.6737(5) _cell_length_b 13.8295(8) _cell_length_c 13.7694(8) _cell_angle_alpha 90.00 _cell_angle_beta 106.9790(10) _cell_angle_gamma 90.00 _cell_volume 1761.81(17) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 2036 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 23.50 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.070 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 4.918 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5258 _exptl_absorpt_correction_T_max 0.6391 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 9676 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 27.26 _reflns_number_total 3921 _reflns_number_gt 2764 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0417P)^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 3921 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0853 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _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 N3 N 0.0837(3) 0.24801(18) 0.2605(2) 0.0357(6) Uani 1 1 d . . . Br2 Br 0.59699(4) 0.13933(3) 0.32251(3) 0.04768(13) Uani 1 1 d . . . Br1 Br 0.49645(4) 0.14502(3) 0.56194(3) 0.04845(13) Uani 1 1 d . . . S1 S 0.16600(9) 0.34473(6) 0.25329(6) 0.03266(19) Uani 1 1 d . . . S2 S -0.08519(9) 0.23722(6) 0.23038(7) 0.0402(2) Uani 1 1 d . . . C2 C 0.3887(3) 0.1056(2) 0.4336(2) 0.0308(7) Uani 1 1 d . . . C3 C 0.4260(3) 0.1033(2) 0.3469(2) 0.0303(7) Uani 1 1 d . . . C1 C 0.2076(3) 0.0443(2) 0.3158(2) 0.0286(7) Uani 1 1 d . . . H1 H 0.1162 0.0171 0.2817 0.034 Uiso 1 1 calc R . . N1 N 0.3111(3) 0.06431(18) 0.27310(18) 0.0284(6) Uani 1 1 d . . . N2 N 0.2517(3) 0.06826(18) 0.41327(19) 0.0290(6) Uani 1 1 d . . . C5 C 0.3024(4) 0.0466(3) 0.1661(2) 0.0400(9) Uani 1 1 d . . . H5A H 0.3468 0.1016 0.1400 0.048 Uiso 1 1 calc R . . H5B H 0.1997 0.0425 0.1253 0.048 Uiso 1 1 calc R . . C6 C 0.3785(4) -0.0454(3) 0.1540(3) 0.0516(10) Uani 1 1 d . . . H6A H 0.4793 -0.0424 0.1964 0.077 Uiso 1 1 calc R . . H6B H 0.3756 -0.0533 0.0827 0.077 Uiso 1 1 calc R . . H6C H 0.3302 -0.1004 0.1751 0.077 Uiso 1 1 calc R . . C4 C 0.1632(4) 0.0602(3) 0.4838(3) 0.0460(9) Uani 1 1 d . . . H4A H 0.0698 0.0308 0.4485 0.069 Uiso 1 1 calc R . . H4B H 0.1473 0.1248 0.5079 0.069 Uiso 1 1 calc R . . H4C H 0.2135 0.0198 0.5417 0.069 Uiso 1 1 calc R . . O1 O 0.0815(3) 0.41961(16) 0.19230(17) 0.0441(6) Uani 1 1 d . . . O3 O -0.1159(3) 0.15327(18) 0.2806(2) 0.0645(8) Uani 1 1 d . . . O2 O 0.3015(3) 0.32081(18) 0.2398(2) 0.0514(7) Uani 1 1 d . . . O4 O -0.1673(3) 0.32268(17) 0.2307(2) 0.0512(7) Uani 1 1 d . . . C7 C 0.2095(5) 0.3904(3) 0.3827(3) 0.0552(11) Uani 1 1 d . . . C8 C -0.1314(4) 0.2036(3) 0.0963(4) 0.0558(11) Uani 1 1 d . . . F2 F 0.2870(3) 0.47044(18) 0.3913(2) 0.0801(8) Uani 1 1 d . . . F1 F 0.0899(3) 0.41217(18) 0.40674(18) 0.0766(8) Uani 1 1 d . . . F3 F 0.2829(4) 0.3271(2) 0.44837(19) 0.1092(12) Uani 1 1 d . . . F4 F -0.1049(3) 0.2736(2) 0.04033(19) 0.0854(8) Uani 1 1 d . . . F5 F -0.0582(3) 0.12419(18) 0.0853(2) 0.0780(8) Uani 1 1 d . . . F6 F -0.2698(3) 0.18130(19) 0.0622(2) 0.0876(9) 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 N3 0.0308(14) 0.0276(14) 0.0496(18) 0.0037(13) 0.0133(13) 0.0011(12) Br2 0.03099(19) 0.0608(3) 0.0534(2) 0.00896(19) 0.01560(16) -0.01132(17) Br1 0.0569(2) 0.0460(2) 0.0346(2) -0.00663(17) 0.00099(17) -0.00906(18) S1 0.0319(4) 0.0324(4) 0.0352(5) -0.0004(4) 0.0121(4) -0.0005(4) S2 0.0289(4) 0.0319(5) 0.0622(6) 0.0030(4) 0.0174(4) 0.0014(4) C2 0.0319(17) 0.0270(16) 0.0311(18) -0.0011(13) 0.0055(14) -0.0010(13) C3 0.0238(15) 0.0327(18) 0.0346(18) 0.0046(14) 0.0089(14) -0.0056(13) C1 0.0231(15) 0.0299(17) 0.0322(18) -0.0014(13) 0.0071(13) 0.0018(13) N1 0.0233(13) 0.0339(15) 0.0273(14) 0.0027(12) 0.0061(11) 0.0030(11) N2 0.0289(14) 0.0287(14) 0.0316(15) 0.0009(12) 0.0123(11) -0.0014(11) C5 0.0364(19) 0.061(2) 0.0228(17) 0.0028(16) 0.0091(15) 0.0029(17) C6 0.061(2) 0.061(3) 0.037(2) -0.0074(18) 0.0205(19) 0.009(2) C4 0.043(2) 0.060(2) 0.044(2) -0.0005(19) 0.0254(17) -0.0053(19) O1 0.0509(15) 0.0361(13) 0.0454(15) 0.0129(12) 0.0143(12) 0.0051(12) O3 0.0487(16) 0.0466(16) 0.105(2) 0.0225(16) 0.0335(17) -0.0043(13) O2 0.0351(13) 0.0525(16) 0.0725(19) -0.0076(14) 0.0251(13) -0.0054(12) O4 0.0364(14) 0.0422(15) 0.0779(19) -0.0050(13) 0.0211(13) 0.0102(12) C7 0.065(3) 0.049(2) 0.047(3) -0.009(2) 0.010(2) 0.008(2) C8 0.035(2) 0.046(2) 0.077(3) -0.016(2) 0.002(2) 0.0041(19) F2 0.0683(16) 0.0655(17) 0.096(2) -0.0414(14) 0.0078(14) -0.0104(14) F1 0.103(2) 0.0797(18) 0.0607(16) -0.0207(14) 0.0442(15) -0.0006(16) F3 0.172(3) 0.085(2) 0.0400(15) -0.0079(14) -0.0165(17) 0.051(2) F4 0.111(2) 0.082(2) 0.0504(16) 0.0020(14) 0.0031(15) -0.0117(17) F5 0.0597(16) 0.0701(17) 0.097(2) -0.0333(15) 0.0109(14) 0.0141(13) F6 0.0485(15) 0.0691(18) 0.120(2) -0.0340(16) -0.0151(15) 0.0049(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 N3 S2 1.571(3) . ? N3 S1 1.574(3) . ? Br2 C3 1.850(3) . ? Br1 C2 1.852(3) . ? S1 O2 1.416(2) . ? S1 O1 1.430(2) . ? S1 C7 1.821(4) . ? S2 O4 1.424(2) . ? S2 O3 1.427(2) . ? S2 C8 1.828(5) . ? C2 C3 1.346(4) . ? C2 N2 1.372(4) . ? C3 N1 1.378(4) . ? C1 N2 1.326(4) . ? C1 N1 1.329(4) . ? C1 H1 0.9500 . ? N1 C5 1.472(4) . ? N2 C4 1.474(4) . ? C5 C6 1.504(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C7 F3 1.310(5) . ? C7 F2 1.323(5) . ? C7 F1 1.327(5) . ? C8 F4 1.309(5) . ? C8 F6 1.320(4) . ? C8 F5 1.339(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S2 N3 S1 124.77(17) . . ? O2 S1 O1 118.99(15) . . ? O2 S1 N3 108.33(15) . . ? O1 S1 N3 116.05(14) . . ? O2 S1 C7 104.56(18) . . ? O1 S1 C7 104.62(17) . . ? N3 S1 C7 102.12(18) . . ? O4 S2 O3 118.58(16) . . ? O4 S2 N3 117.27(15) . . ? O3 S2 N3 107.29(16) . . ? O4 S2 C8 104.01(18) . . ? O3 S2 C8 105.0(2) . . ? N3 S2 C8 102.65(17) . . ? C3 C2 N2 107.6(3) . . ? C3 C2 Br1 129.2(2) . . ? N2 C2 Br1 123.1(2) . . ? C2 C3 N1 107.2(3) . . ? C2 C3 Br2 129.8(2) . . ? N1 C3 Br2 122.9(2) . . ? N2 C1 N1 109.6(3) . . ? N2 C1 H1 125.2 . . ? N1 C1 H1 125.2 . . ? C1 N1 C3 107.7(2) . . ? C1 N1 C5 125.3(3) . . ? C3 N1 C5 126.9(3) . . ? C1 N2 C2 107.9(2) . . ? C1 N2 C4 124.8(3) . . ? C2 N2 C4 127.3(3) . . ? N1 C5 C6 111.4(3) . . ? N1 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? N1 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? F3 C7 F2 108.6(4) . . ? F3 C7 F1 108.4(4) . . ? F2 C7 F1 107.5(3) . . ? F3 C7 S1 111.5(3) . . ? F2 C7 S1 109.9(3) . . ? F1 C7 S1 110.7(3) . . ? F4 C8 F6 108.5(4) . . ? F4 C8 F5 109.9(4) . . ? F6 C8 F5 106.4(3) . . ? F4 C8 S2 112.0(3) . . ? F6 C8 S2 110.0(3) . . ? F5 C8 S2 110.0(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 S2 N3 S1 O2 -153.1(2) . . . . ? S2 N3 S1 O1 -16.2(3) . . . . ? S2 N3 S1 C7 96.9(2) . . . . ? S1 N3 S2 O4 -22.8(3) . . . . ? S1 N3 S2 O3 -159.2(2) . . . . ? S1 N3 S2 C8 90.5(2) . . . . ? N2 C2 C3 N1 0.1(3) . . . . ? Br1 C2 C3 N1 177.4(2) . . . . ? N2 C2 C3 Br2 -178.1(2) . . . . ? Br1 C2 C3 Br2 -0.7(5) . . . . ? N2 C1 N1 C3 -0.3(3) . . . . ? N2 C1 N1 C5 179.3(3) . . . . ? C2 C3 N1 C1 0.2(3) . . . . ? Br2 C3 N1 C1 178.4(2) . . . . ? C2 C3 N1 C5 -179.4(3) . . . . ? Br2 C3 N1 C5 -1.1(4) . . . . ? N1 C1 N2 C2 0.4(3) . . . . ? N1 C1 N2 C4 177.3(3) . . . . ? C3 C2 N2 C1 -0.3(3) . . . . ? Br1 C2 N2 C1 -177.8(2) . . . . ? C3 C2 N2 C4 -177.0(3) . . . . ? Br1 C2 N2 C4 5.4(4) . . . . ? C1 N1 C5 C6 -99.0(4) . . . . ? C3 N1 C5 C6 80.5(4) . . . . ? O2 S1 C7 F3 -56.7(4) . . . . ? O1 S1 C7 F3 177.5(3) . . . . ? N3 S1 C7 F3 56.2(4) . . . . ? O2 S1 C7 F2 63.8(3) . . . . ? O1 S1 C7 F2 -62.0(3) . . . . ? N3 S1 C7 F2 176.7(3) . . . . ? O2 S1 C7 F1 -177.5(3) . . . . ? O1 S1 C7 F1 56.7(3) . . . . ? N3 S1 C7 F1 -64.7(3) . . . . ? O4 S2 C8 F4 56.4(3) . . . . ? O3 S2 C8 F4 -178.3(3) . . . . ? N3 S2 C8 F4 -66.2(3) . . . . ? O4 S2 C8 F6 -64.2(3) . . . . ? O3 S2 C8 F6 61.0(3) . . . . ? N3 S2 C8 F6 173.1(3) . . . . ? O4 S2 C8 F5 178.9(3) . . . . ? O3 S2 C8 F5 -55.9(3) . . . . ? N3 S2 C8 F5 56.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.385 _refine_diff_density_min -0.587 _refine_diff_density_rms 0.104 _database_code_depnum_ccdc_archive 'CCDC 942517'