# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2009 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Patrick Batail' _publ_contact_author_email PATRICK.BATAIL@UNIV-ANGERS.FR _publ_section_title ; Charge Ordering, Symmetry and Electronic Structure Issues and Wigner Crystal Structure of the Quarter-Filled Band Mott Insulators and High Pressure Metals delta-(EDT-TTF-CONMe2)2X, X = Br and AsF6 ; loop_ _publ_author_name 'Patrick Batail' 'Stuart E. Brown' 'Enric Canadell' 'Pierre Fertey' 'Pascale Foury-Leylekian' ; C.Meziere ; 'Jean-Paul Pouget' 'Sergey Simonov' 'Steve Suh' 'Leokadiya V. Zorina' # Attachment 'AsF6-100K.CIF' data_delta-(EDT-TTF-CONMe2)2AsF6_(P21/a,100K) _database_code_depnum_ccdc_archive 'CCDC 727931' _audit_creation_method ; CrysAlis RED (Oxford Diffraction Ltd.), SHELXL-97 and WinGX routine-INITIALISE ; _chemical_name_systematic ; ? ; _chemical_compound_source 'synthesis as described' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C11 H11 N O S6), As F6' _chemical_formula_sum 'C22 H22 As F6 N2 O2 S12' _chemical_formula_weight 920.06 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' As As 0.0499 2.0058 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 1 21/a' _symmetry_space_group_name_Hall '-P 2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' _cell_length_a 7.0157(8) _cell_length_b 6.4219(13) _cell_length_c 35.465(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 92.255(13) _cell_volume 1596.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 90 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.228 _exptl_crystal_size_mid 0.052 _exptl_crystal_size_min 0.050 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.914 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 926 _exptl_absorpt_coefficient_mu 1.915 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.7476 _exptl_absorpt_correction_T_max 0.9152 _exptl_absorpt_process_details 'see N.W. Alcock (1970). Cryst. Computing, p.271' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD' _diffrn_measurement_method 'combined \f and \w-scans' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_detector_area_resol_mean 9 _diffrn_standards_decay_% 0 _diffrn_reflns_number 46120 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0876 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -52 _diffrn_reflns_limit_l_max 52 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 32.07 _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 46120 _reflns_number_gt 28241 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'Direct methods (Sir92,Altomare et al.,1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1 (Crystal Impact GbR 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1073P)^2^+4.8322P] 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 46120 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1471 _refine_ls_R_factor_gt 0.0784 _refine_ls_wR_factor_ref 0.2160 _refine_ls_wR_factor_gt 0.1832 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 1.747 _refine_diff_density_min -0.909 _refine_diff_density_rms 0.202 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 As1 As 0.0000 0.0000 0.0000 0.01978(8) Uani 1 2 d S . . F1 F 0.0181(3) -0.1357(2) 0.04074(4) 0.0766(6) Uani 1 1 d . . . F3 F 0.1746(2) 0.1698(3) 0.01559(5) 0.0610(5) Uani 1 1 d . . . F2 F -0.1644(2) 0.1492(3) 0.02092(5) 0.0681(6) Uani 1 1 d . . . S3 S 0.00277(7) 0.48789(8) 0.310099(13) 0.01624(11) Uani 1 1 d . . . S6 S 0.01141(7) 0.69112(8) 0.116931(13) 0.01704(11) Uani 1 1 d . . . S2 S 0.03535(7) 0.77584(8) 0.198809(14) 0.01701(11) Uani 1 1 d . . . S1 S -0.00318(7) 0.33910(8) 0.222154(14) 0.01902(12) Uani 1 1 d . . . S4 S 0.03564(7) 0.92270(8) 0.285259(14) 0.01893(12) Uani 1 1 d . . . S5 S -0.03912(8) 0.16903(8) 0.145438(14) 0.02190(13) Uani 1 1 d . . . C2 C 0.0174(2) 0.6600(3) 0.27251(5) 0.0134(4) Uani 1 1 d . . . O1 O 0.00520(18) 0.3842(2) 0.38225(4) 0.0201(3) Uani 1 1 d . . . C4 C 0.0071(2) 0.5902(3) 0.16273(5) 0.0136(4) Uani 1 1 d . . . C3 C -0.0104(3) 0.3896(3) 0.17386(5) 0.0161(4) Uani 1 1 d . . . C7 C 0.0589(3) 0.2683(3) 0.10199(6) 0.0192(4) Uani 1 1 d . . . H7A H 0.1939 0.3009 0.1055 0.023 Uiso 1 1 calc R . . H7B H 0.0461 0.1607 0.0829 0.023 Uiso 1 1 calc R . . C8 C -0.0362(3) 0.4606(3) 0.08817(6) 0.0187(4) Uani 1 1 d . . . H8A H -0.1730 0.4319 0.0873 0.022 Uiso 1 1 calc R . . H8B H 0.0063 0.4900 0.0626 0.022 Uiso 1 1 calc R . . N1 N 0.0026(2) 0.6874(3) 0.41527(4) 0.0179(4) Uani 1 1 d . . . C1 C 0.0154(2) 0.5990(3) 0.23580(5) 0.0158(4) Uani 1 1 d . . . C9 C 0.0052(2) 0.5779(3) 0.38312(5) 0.0146(4) Uani 1 1 d . . . C5 C 0.0121(3) 0.6812(3) 0.34532(5) 0.0154(4) Uani 1 1 d . . . C6 C 0.0268(2) 0.8795(3) 0.33313(5) 0.0174(4) Uani 1 1 d . . . H6 H 0.0321 0.9901 0.3501 0.021 Uiso 1 1 calc R . . C10 C -0.0103(3) 0.5761(4) 0.45113(6) 0.0236(5) Uani 1 1 d . . . H10A H -0.0082 0.4288 0.4466 0.035 Uiso 1 1 calc R . . H10B H -0.1271 0.6080 0.4636 0.035 Uiso 1 1 calc R . . H10C H 0.0960 0.6183 0.4668 0.035 Uiso 1 1 calc R . . C11 C 0.0028(3) 0.9147(3) 0.41752(6) 0.0275(5) Uani 1 1 d . . . H11A H 0.1198 0.9727 0.4073 0.041 Uiso 1 1 calc R . . H11B H -0.0086 0.9564 0.4434 0.041 Uiso 1 1 calc R . . H11C H -0.1029 0.9645 0.4034 0.041 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 As1 0.03300(18) 0.01799(18) 0.00813(15) 0.00169(12) -0.00046(12) -0.00188(13) F1 0.1872(19) 0.0278(10) 0.0142(8) 0.0066(7) -0.0186(10) -0.0045(11) F3 0.0658(10) 0.0791(13) 0.0346(10) -0.0267(9) 0.0123(8) -0.0399(9) F2 0.0576(10) 0.0962(15) 0.0530(12) -0.0479(11) -0.0145(8) 0.0334(10) S3 0.0218(3) 0.0167(3) 0.0102(2) 0.00036(19) -0.00004(18) 0.0011(2) S6 0.0245(3) 0.0169(3) 0.0096(2) 0.00053(19) -0.00003(19) 0.0012(2) S2 0.0250(3) 0.0158(3) 0.0101(2) 0.00022(19) 0.00085(18) 0.0005(2) S1 0.0297(3) 0.0168(3) 0.0107(2) 0.00157(19) -0.00071(19) 0.0017(2) S4 0.0277(3) 0.0170(3) 0.0120(3) 0.0008(2) -0.00028(19) -0.0007(2) S5 0.0375(3) 0.0158(3) 0.0122(3) -0.0001(2) -0.0014(2) -0.0013(2) C2 0.0128(9) 0.0166(11) 0.0107(9) -0.0004(7) 0.0009(7) 0.0015(8) O1 0.0267(8) 0.0186(8) 0.0149(7) 0.0020(6) 0.0006(6) 0.0011(6) C4 0.0125(9) 0.0183(11) 0.0101(9) -0.0022(8) 0.0002(7) 0.0025(8) C3 0.0184(10) 0.0183(11) 0.0117(10) -0.0003(8) -0.0012(7) 0.0019(8) C7 0.0246(11) 0.0183(12) 0.0146(10) -0.0029(8) 0.0004(8) 0.0010(9) C8 0.0247(11) 0.0197(12) 0.0118(10) -0.0023(8) -0.0009(8) 0.0018(8) N1 0.0224(9) 0.0203(10) 0.0111(8) 0.0001(7) 0.0007(7) 0.0013(7) C1 0.0142(9) 0.0200(11) 0.0136(10) 0.0020(8) -0.0010(7) 0.0038(8) C9 0.0106(9) 0.0185(11) 0.0145(10) 0.0017(8) -0.0016(7) -0.0011(8) C5 0.0144(9) 0.0214(12) 0.0104(9) -0.0016(8) -0.0009(7) 0.0018(8) C6 0.0188(10) 0.0248(12) 0.0083(9) -0.0023(8) -0.0017(7) -0.0017(8) C10 0.0289(12) 0.0299(13) 0.0118(10) 0.0040(9) 0.0017(8) -0.0005(9) C11 0.0403(13) 0.0267(13) 0.0157(11) -0.0053(10) 0.0045(9) 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 As1 F1 1.6945(15) . ? As1 F1 1.6945(15) 3 ? As1 F2 1.6988(15) . ? As1 F2 1.6988(15) 3 ? As1 F3 1.7002(14) 3 ? As1 F3 1.7002(14) . ? S3 C2 1.732(2) . ? S3 C5 1.761(2) . ? S6 C4 1.7483(19) . ? S6 C8 1.818(2) . ? S2 C1 1.737(2) . ? S2 C4 1.755(2) . ? S1 C1 1.738(2) . ? S1 C3 1.744(2) . ? S4 C6 1.7208(19) . ? S4 C2 1.746(2) . ? S5 C3 1.744(2) . ? S5 C7 1.794(2) . ? C2 C1 1.359(3) . ? O1 C9 1.244(2) . ? C4 C3 1.349(3) . ? C7 C8 1.509(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? N1 C9 1.340(2) . ? N1 C10 1.460(3) . ? N1 C11 1.462(3) . ? C9 C5 1.496(3) . ? C5 C6 1.345(3) . ? C6 H6 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? 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 F1 As1 F1 180.00(10) . 3 ? F1 As1 F2 89.07(9) . . ? F1 As1 F2 90.93(9) 3 . ? F1 As1 F2 90.93(9) . 3 ? F1 As1 F2 89.07(9) 3 3 ? F2 As1 F2 180.00(13) . 3 ? F1 As1 F3 90.80(9) . 3 ? F1 As1 F3 89.20(9) 3 3 ? F2 As1 F3 90.89(8) . 3 ? F2 As1 F3 89.11(8) 3 3 ? F1 As1 F3 89.20(9) . . ? F1 As1 F3 90.80(9) 3 . ? F2 As1 F3 89.11(8) . . ? F2 As1 F3 90.89(8) 3 . ? F3 As1 F3 180.00(14) 3 . ? C2 S3 C5 95.54(9) . . ? C4 S6 C8 102.69(10) . . ? C1 S2 C4 95.90(10) . . ? C1 S1 C3 95.54(10) . . ? C6 S4 C2 95.68(10) . . ? C3 S5 C7 100.22(10) . . ? C1 C2 S3 123.61(16) . . ? C1 C2 S4 121.72(16) . . ? S3 C2 S4 114.67(10) . . ? C3 C4 S6 128.72(15) . . ? C3 C4 S2 116.05(15) . . ? S6 C4 S2 115.21(11) . . ? C4 C3 S5 127.61(15) . . ? C4 C3 S1 117.57(15) . . ? S5 C3 S1 114.83(12) . . ? C8 C7 S5 113.23(14) . . ? C8 C7 H7A 108.9 . . ? S5 C7 H7A 108.9 . . ? C8 C7 H7B 108.9 . . ? S5 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C7 C8 S6 114.28(14) . . ? C7 C8 H8A 108.7 . . ? S6 C8 H8A 108.7 . . ? C7 C8 H8B 108.7 . . ? S6 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C9 N1 C10 119.10(17) . . ? C9 N1 C11 124.81(17) . . ? C10 N1 C11 116.02(16) . . ? C2 C1 S2 122.37(16) . . ? C2 C1 S1 122.88(15) . . ? S2 C1 S1 114.75(11) . . ? O1 C9 N1 123.11(18) . . ? O1 C9 C5 114.82(17) . . ? N1 C9 C5 122.06(18) . . ? C6 C5 C9 135.09(18) . . ? C6 C5 S3 116.03(15) . . ? C9 C5 S3 108.87(14) . . ? C5 C6 S4 118.09(16) . . ? C5 C6 H6 121.0 . . ? S4 C6 H6 121.0 . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? # Attachment 'Br-150K.CIF' data_delta-(EDT-TTF-CONMe2)2Br_(P21/a,150K) _database_code_depnum_ccdc_archive 'CCDC 727932' _audit_creation_method ; CrysAlis RED (Oxford Diffraction Ltd.), SHELXL-97 and WinGX routine-INITIALISE ; _chemical_name_systematic ; ? ; _chemical_compound_source 'synthesis as described' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C11 H11 N O S6), Br' _chemical_formula_sum 'C22 H22 Br N2 O2 S12' _chemical_formula_weight 811.05 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' 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 1 1 21/a' _symmetry_space_group_name_Hall '-P 2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' _cell_length_a 6.9762(9) _cell_length_b 6.4800(12) _cell_length_c 32.671(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 92.446(18) _cell_volume 1475.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 100 _cell_measurement_theta_min 3 _cell_measurement_theta_max 30 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.227 _exptl_crystal_size_mid 0.054 _exptl_crystal_size_min 0.038 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.825 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 822 _exptl_absorpt_coefficient_mu 2.271 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.7353 _exptl_absorpt_correction_T_max 0.9199 _exptl_absorpt_process_details 'see N.W. Alcock (1970). Cryst. Computing, p.271' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD' _diffrn_measurement_method 'combined \f and \w-scans' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_detector_area_resol_mean 9 _diffrn_standards_decay_% 0 _diffrn_reflns_number 37386 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0836 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 30.20 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _reflns_number_total 37386 _reflns_number_gt 23511 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'Direct methods (Sir92,Altomare et al.,1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1 (Crystal Impact GbR 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0721P)^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 37386 _refine_ls_number_parameters 189 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1026 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1274 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 1.169 _refine_diff_density_min -0.703 _refine_diff_density_rms 0.111 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 Br Br 0.0000 0.0000 1.0000 0.03101(7) Uani 1 2 d S . . S1 S 0.51106(6) 0.44616(6) 0.715037(11) 0.02378(10) Uani 1 1 d . . . S2 S 0.52823(6) 0.87922(6) 0.689811(10) 0.02094(9) Uani 1 1 d . . . S3 S 0.51470(6) 0.59847(6) 0.811258(10) 0.02039(9) Uani 1 1 d . . . S4 S 0.53249(6) 1.02743(6) 0.782750(11) 0.02565(10) Uani 1 1 d . . . S5 S 0.49442(7) 0.27586(6) 0.631616(12) 0.03150(11) Uani 1 1 d . . . S6 S 0.51177(5) 0.79663(6) 0.600733(10) 0.01942(9) Uani 1 1 d . . . C1 C 0.5200(2) 0.7040(2) 0.72996(4) 0.0179(3) Uani 1 1 d . . . C2 C 0.5214(2) 0.7663(2) 0.76979(4) 0.0181(3) Uani 1 1 d . . . C3 C 0.5076(2) 0.4956(2) 0.66236(4) 0.0196(3) Uani 1 1 d . A . C4 C 0.5148(2) 0.6954(2) 0.65032(4) 0.0159(3) Uani 1 1 d . A . C5 C 0.5197(2) 0.7931(2) 0.84869(4) 0.0177(3) Uani 1 1 d . . . C6 C 0.5277(2) 0.9890(2) 0.83501(4) 0.0234(4) Uani 1 1 d . . . H6 H 0.5305 1.0999 0.8531 0.028 Uiso 1 1 calc R . . C7 C 0.5729(3) 0.3816(3) 0.58325(5) 0.0213(5) Uani 0.867(3) 1 d PD A 1 H7A H 0.7078 0.4233 0.5851 0.026 Uiso 0.867(3) 1 calc PR A 1 H7B H 0.5592 0.2754 0.5624 0.026 Uiso 0.867(3) 1 calc PR A 1 C8 C 0.4606(3) 0.5651(3) 0.57056(5) 0.0197(5) Uani 0.867(3) 1 d PD A 1 H8A H 0.3248 0.5282 0.5727 0.024 Uiso 0.867(3) 1 calc PR A 1 H8B H 0.4882 0.5960 0.5421 0.024 Uiso 0.867(3) 1 calc PR A 1 C7B C 0.443(2) 0.3806(17) 0.5822(4) 0.0213(5) Uani 0.133(3) 1 d PD A 2 H7B1 H 0.4635 0.2758 0.5617 0.026 Uiso 0.133(3) 1 calc PR A 2 H7B2 H 0.3080 0.4119 0.5813 0.026 Uiso 0.133(3) 1 calc PR A 2 C8B C 0.561(2) 0.574(2) 0.5710(4) 0.0197(5) Uani 0.133(3) 1 d PD A 2 H8B1 H 0.5393 0.6056 0.5424 0.024 Uiso 0.133(3) 1 calc PR A 2 H8B2 H 0.6961 0.5463 0.5740 0.024 Uiso 0.133(3) 1 calc PR A 2 C9 C 0.5145(2) 0.6959(2) 0.89032(4) 0.0178(3) Uani 1 1 d . . . C10 C 0.4958(2) 0.7051(3) 0.96411(4) 0.0295(4) Uani 1 1 d . . . H10A H 0.3800 0.7412 0.9778 0.044 Uiso 1 1 calc R . . H10B H 0.6045 0.7478 0.9805 0.044 Uiso 1 1 calc R . . H10C H 0.4947 0.5583 0.9601 0.044 Uiso 1 1 calc R . . C11 C 0.5087(3) 1.0345(3) 0.92609(5) 0.0454(5) Uani 1 1 d . . . H11A H 0.6276 1.0911 0.9153 0.068 Uiso 1 1 calc R . . H11B H 0.4949 1.0778 0.9540 0.068 Uiso 1 1 calc R . . H11C H 0.4040 1.0826 0.9101 0.068 Uiso 1 1 calc R . . N1 N 0.50803(17) 0.8090(2) 0.92433(3) 0.0236(3) Uani 1 1 d . . . O1 O 0.51455(14) 0.50338(15) 0.89034(3) 0.0241(2) 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 Br 0.05542(18) 0.02306(13) 0.01436(11) -0.00022(9) 0.00225(11) -0.00068(11) S1 0.0437(3) 0.01532(19) 0.01232(17) 0.00318(15) -0.00042(17) 0.00147(18) S2 0.0388(3) 0.01479(19) 0.00920(16) 0.00113(14) 0.00005(16) 0.00116(17) S3 0.0331(3) 0.0176(2) 0.01048(17) 0.00197(14) -0.00016(16) 0.00190(17) S4 0.0482(3) 0.0167(2) 0.01188(17) 0.00205(15) -0.00044(18) -0.00018(18) S5 0.0662(3) 0.0135(2) 0.0148(2) 0.00029(15) -0.00084(19) 0.0016(2) S6 0.0340(2) 0.01504(18) 0.00931(17) 0.00102(14) -0.00024(15) 0.00196(16) C1 0.0229(9) 0.0175(8) 0.0133(7) 0.0016(6) -0.0006(6) 0.0020(6) C2 0.0225(9) 0.0179(8) 0.0141(7) 0.0017(6) 0.0000(6) 0.0017(6) C3 0.0283(9) 0.0176(8) 0.0130(7) 0.0004(6) -0.0013(6) 0.0024(7) C4 0.0201(9) 0.0163(8) 0.0117(7) -0.0008(6) -0.0010(6) 0.0031(6) C5 0.0201(9) 0.0219(8) 0.0112(7) 0.0002(6) 0.0002(6) 0.0013(7) C6 0.0381(11) 0.0203(8) 0.0118(7) 0.0000(6) 0.0005(7) -0.0004(7) C7 0.0271(14) 0.0199(9) 0.0171(8) -0.0030(7) -0.0006(9) 0.0022(9) C8 0.0280(14) 0.0169(9) 0.0139(8) -0.0002(7) -0.0022(10) -0.0021(10) C7B 0.0271(14) 0.0199(9) 0.0171(8) -0.0030(7) -0.0006(9) 0.0022(9) C8B 0.0280(14) 0.0169(9) 0.0139(8) -0.0002(7) -0.0022(10) -0.0021(10) C9 0.0156(9) 0.0238(8) 0.0139(7) 0.0042(6) -0.0001(6) 0.0022(6) C10 0.0420(11) 0.0357(10) 0.0109(7) 0.0024(7) 0.0010(7) 0.0042(8) C11 0.0941(16) 0.0282(10) 0.0142(8) -0.0062(7) 0.0040(9) 0.0062(10) N1 0.0356(8) 0.0235(7) 0.0119(6) 0.0013(5) 0.0011(6) 0.0037(6) O1 0.0360(7) 0.0197(6) 0.0164(5) 0.0036(4) 0.0007(5) 0.0009(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.7388(15) . ? S1 C3 1.7511(15) . ? S2 C1 1.7344(14) . ? S2 C4 1.7560(14) . ? S3 C2 1.7368(15) . ? S3 C5 1.7563(15) . ? S4 C6 1.7257(15) . ? S4 C2 1.7427(15) . ? S5 C3 1.7418(15) . ? S5 C7B 1.794(12) . ? S5 C7 1.7984(18) . ? S6 C4 1.7483(14) . ? S6 C8B 1.783(14) . ? S6 C8 1.8176(18) . ? C1 C2 1.3624(19) . ? C3 C4 1.3516(19) . ? C5 C6 1.344(2) . ? C5 C9 1.4987(19) . ? C6 H6 0.9300 . ? C7 C8 1.510(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C7B C8B 1.520(14) . ? C7B H7B1 0.9700 . ? C7B H7B2 0.9700 . ? C8B H8B1 0.9700 . ? C8B H8B2 0.9700 . ? C9 O1 1.2478(17) . ? C9 N1 1.3328(18) . ? C10 N1 1.4643(18) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 N1 1.4621(19) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C3 95.74(7) . . ? C1 S2 C4 96.44(7) . . ? C2 S3 C5 95.41(7) . . ? C6 S4 C2 95.76(7) . . ? C3 S5 C7B 102.4(4) . . ? C3 S5 C7 100.99(8) . . ? C4 S6 C8B 101.3(4) . . ? C4 S6 C8 101.41(8) . . ? C2 C1 S2 121.91(12) . . ? C2 C1 S1 123.52(12) . . ? S2 C1 S1 114.57(8) . . ? C1 C2 S3 124.03(12) . . ? C1 C2 S4 121.30(11) . . ? S3 C2 S4 114.67(8) . . ? C4 C3 S5 127.85(11) . . ? C4 C3 S1 117.46(11) . . ? S5 C3 S1 114.69(8) . . ? C3 C4 S6 128.94(11) . . ? C3 C4 S2 115.76(11) . . ? S6 C4 S2 115.30(8) . . ? C6 C5 C9 134.25(14) . . ? C6 C5 S3 116.43(11) . . ? C9 C5 S3 109.32(10) . . ? C5 C6 S4 117.72(12) . . ? C5 C6 H6 121.1 . . ? S4 C6 H6 121.1 . . ? C8 C7 S5 112.43(15) . . ? C8 C7 H7A 109.1 . . ? S5 C7 H7A 109.1 . . ? C8 C7 H7B 109.1 . . ? S5 C7 H7B 109.1 . . ? H7A C7 H7B 107.9 . . ? C7 C8 S6 114.27(14) . . ? C7 C8 H8A 108.7 . . ? S6 C8 H8A 108.7 . . ? C7 C8 H8B 108.7 . . ? S6 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C8B C7B S5 114.7(10) . . ? C8B C7B H7B1 108.6 . . ? S5 C7B H7B1 108.6 . . ? C8B C7B H7B2 108.6 . . ? S5 C7B H7B2 108.6 . . ? H7B1 C7B H7B2 107.6 . . ? C7B C8B S6 114.7(10) . . ? C7B C8B H8B1 108.6 . . ? S6 C8B H8B1 108.6 . . ? C7B C8B H8B2 108.6 . . ? S6 C8B H8B2 108.6 . . ? H8B1 C8B H8B2 107.6 . . ? O1 C9 N1 123.43(13) . . ? O1 C9 C5 114.80(12) . . ? N1 C9 C5 121.76(13) . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 N1 C11 125.69(12) . . ? C9 N1 C10 119.34(13) . . ? C11 N1 C10 114.97(12) . . ? # Attachment 'Br-295K.CIF' data_delta-(EDT-TTF-CONMe2)2Br_(Pmna,295K) _database_code_depnum_ccdc_archive 'CCDC 727933' _audit_creation_method ; CrysAlis RED (Oxford Diffraction Ltd.), SHELXL-97 and WinGX routine-INITIALISE ; _chemical_name_systematic ; ? ; _chemical_compound_source 'synthesis as described' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C11 H11 N O S6), Br' _chemical_formula_sum 'C22 H22 Br N2 O2 S12' _chemical_formula_weight 811.05 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' 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 orthorhombic _symmetry_space_group_name_H-M 'P m n a' _symmetry_space_group_name_Hall '-P 2ac 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x, -y, -z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x, y, z' 'x-1/2, -y, z-1/2' _cell_length_a 7.1097(4) _cell_length_b 6.5049(9) _cell_length_c 32.691(3) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 1511.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 70 _cell_measurement_theta_min 3 _cell_measurement_theta_max 30 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.227 _exptl_crystal_size_mid 0.054 _exptl_crystal_size_min 0.038 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.782 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 822 _exptl_absorpt_coefficient_mu 2.216 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.7317 _exptl_absorpt_correction_T_max 0.9218 _exptl_absorpt_process_details 'see N.W. Alcock (1970). Cryst. Computing, p.271' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD' _diffrn_measurement_method 'combined \f and \w-scans' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_detector_area_resol_mean 9 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18647 _diffrn_reflns_av_R_equivalents 0.0674 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 30.02 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.984 _reflns_number_total 2333 _reflns_number_gt 1477 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'Direct methods (Sir92,Altomare et al.,1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1 (Crystal Impact GbR 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0310P)^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 2333 _refine_ls_number_parameters 134 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0767 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0676 _refine_ls_wR_factor_gt 0.0599 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.312 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.064 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 Br Br 0.0000 0.0000 1.0000 0.05840(16) Uani 1 4 d S . . S1 S 0.0000 0.44645(9) 0.784559(19) 0.04662(19) Uani 1 2 d S . . S2 S 0.0000 0.87619(9) 0.809827(18) 0.04186(18) Uani 1 2 d S . . S3 S 0.0000 0.59893(9) 0.688473(18) 0.03917(17) Uani 1 2 d S . . S4 S 0.0000 1.02480(10) 0.71711(2) 0.0506(2) Uani 1 2 d S . . S5 S -0.0311(10) 0.27808(12) 0.86770(3) 0.0488(14) Uani 0.50 1 d P . . S6 S 0.0000 0.79425(9) 0.898629(17) 0.03770(17) Uani 1 2 d S . . C1 C 0.0000 0.7026(4) 0.76974(7) 0.0354(5) Uani 1 2 d S . . C2 C 0.0000 0.7648(4) 0.72989(7) 0.0350(5) Uani 1 2 d S . . C3 C 0.0000 0.4958(4) 0.83707(7) 0.0383(6) Uani 1 2 d S . . C4 C 0.0000 0.6933(4) 0.84898(6) 0.0319(5) Uani 1 2 d S . . C5 C 0.0000 0.7924(4) 0.65110(7) 0.0323(5) Uani 1 2 d S . . C6 C 0.0000 0.9860(4) 0.66496(8) 0.0447(6) Uani 1 2 d S . . H6 H 0.0000 1.0966 0.6469 0.054 Uiso 1 2 calc SR . . C7 C -0.0678(4) 0.3812(5) 0.91631(10) 0.0426(11) Uani 0.50 1 d P . . H7A H -0.1993 0.4196 0.9184 0.051 Uiso 0.50 1 calc PR . . H7B H -0.0456 0.2732 0.9362 0.051 Uiso 0.50 1 calc PR . . C8 C 0.0496(5) 0.5659(5) 0.92850(9) 0.0345(14) Uani 0.50 1 d P . . H8A H 0.1816 0.5315 0.9255 0.041 Uiso 0.50 1 calc PR . . H8B H 0.0272 0.5960 0.9572 0.041 Uiso 0.50 1 calc PR . . C9 C 0.0000 0.6971(4) 0.60951(7) 0.0358(6) Uani 1 2 d S . . O1 O 0.0000 0.5063(3) 0.60942(5) 0.0465(5) Uani 1 2 d S . . N1 N 0.0000 0.8094(3) 0.57546(6) 0.0439(5) Uani 1 2 d S . . C10 C 0.0000 0.7054(5) 0.53602(7) 0.0576(8) Uani 1 2 d S . . H10A H -0.0827 0.7763 0.5176 0.086 Uiso 0.50 1 calc PR . . H10B H -0.0425 0.5665 0.5395 0.086 Uiso 0.50 1 calc PR . . H10C H 0.1252 0.7050 0.5250 0.086 Uiso 0.50 1 calc PR . . C11 C -0.036(2) 1.0311(5) 0.57354(11) 0.058(4) Uani 0.50 1 d P . . H11A H -0.0769 1.0673 0.5465 0.087 Uiso 0.50 1 calc PR . . H11B H 0.0774 1.1045 0.5799 0.087 Uiso 0.50 1 calc PR . . H11C H -0.1320 1.0668 0.5929 0.087 Uiso 0.50 1 calc PR . . 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 Br 0.0985(4) 0.0461(2) 0.0306(2) -0.00032(17) 0.000 0.000 S1 0.0860(5) 0.0288(3) 0.0251(3) -0.0065(3) 0.000 0.000 S2 0.0782(5) 0.0269(3) 0.0205(3) -0.0026(2) 0.000 0.000 S3 0.0628(4) 0.0323(3) 0.0224(3) -0.0044(2) 0.000 0.000 S4 0.0949(6) 0.0322(3) 0.0248(3) -0.0049(3) 0.000 0.000 S5 0.089(4) 0.0255(3) 0.0317(4) -0.0002(3) 0.0037(7) -0.0052(7) S6 0.0649(4) 0.0277(3) 0.0205(3) -0.0023(2) 0.000 0.000 C1 0.0483(15) 0.0342(12) 0.0238(12) -0.0049(10) 0.000 0.000 C2 0.0490(15) 0.0331(12) 0.0230(13) -0.0069(10) 0.000 0.000 C3 0.0623(16) 0.0300(12) 0.0227(12) -0.0023(9) 0.000 0.000 C4 0.0463(15) 0.0310(12) 0.0184(11) -0.0010(9) 0.000 0.000 C5 0.0389(14) 0.0354(12) 0.0226(12) 0.0004(10) 0.000 0.000 C6 0.0726(18) 0.0396(14) 0.0218(12) 0.0017(11) 0.000 0.000 C7 0.061(3) 0.0366(17) 0.0305(17) 0.0069(15) -0.0016(15) -0.0047(14) C8 0.041(4) 0.0354(16) 0.0277(15) 0.0025(13) -0.0026(13) 0.0047(14) C9 0.0363(15) 0.0462(15) 0.0248(13) -0.0072(11) 0.000 0.000 O1 0.0696(12) 0.0387(10) 0.0313(10) -0.0091(8) 0.000 0.000 N1 0.0611(14) 0.0480(13) 0.0226(11) -0.0018(9) 0.000 0.000 C10 0.077(2) 0.0716(19) 0.0240(14) -0.0057(14) 0.000 0.000 C11 0.082(12) 0.058(2) 0.0347(18) 0.0065(15) -0.002(3) -0.004(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 C1 1.735(2) . ? S1 C3 1.746(2) . ? S2 C1 1.730(2) . ? S2 C4 1.747(2) . ? S3 C2 1.731(2) . ? S3 C5 1.754(2) . ? S4 C6 1.724(3) . ? S4 C2 1.742(2) . ? S5 C7 1.744(4) . ? S5 C3 1.749(3) . ? S6 C4 1.751(2) . ? S6 C8 1.812(3) . ? C1 C2 1.364(3) . ? C3 C4 1.343(3) . ? C5 C6 1.338(3) . ? C5 C9 1.494(3) . ? C6 H6 0.9300 . ? C7 C8 1.517(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O1 1.241(3) . ? C9 N1 1.332(3) . ? N1 C10 1.456(3) . ? N1 C11 1.466(5) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C3 95.61(11) . . ? C1 S2 C4 96.35(11) . . ? C2 S3 C5 95.59(11) . . ? C6 S4 C2 95.46(12) . . ? C7 S5 C3 103.25(14) . . ? C4 S6 C8 101.09(13) . . ? C2 C1 S2 122.0(2) . . ? C2 C1 S1 123.47(19) . . ? S2 C1 S1 114.55(13) . . ? C1 C2 S3 124.2(2) . . ? C1 C2 S4 121.14(19) . . ? S3 C2 S4 114.67(13) . . ? C4 C3 S1 117.46(19) . . ? C4 C3 S5 127.51(19) . . ? S1 C3 S5 114.46(13) . . ? C3 C4 S2 116.04(18) . . ? C3 C4 S6 128.88(19) . . ? S2 C4 S6 115.08(13) . . ? C6 C5 C9 134.3(2) . . ? C6 C5 S3 116.07(18) . . ? C9 C5 S3 109.63(17) . . ? C5 C6 S4 118.2(2) . . ? C5 C6 H6 120.9 . . ? S4 C6 H6 120.9 . . ? C8 C7 S5 117.5(3) . . ? C8 C7 H7A 107.9 . . ? S5 C7 H7A 107.9 . . ? C8 C7 H7B 107.9 . . ? S5 C7 H7B 107.9 . . ? H7A C7 H7B 107.2 . . ? C7 C8 S6 113.6(2) . . ? C7 C8 H8A 108.8 . . ? S6 C8 H8A 108.8 . . ? C7 C8 H8B 108.8 . . ? S6 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? O1 C9 N1 123.1(2) . . ? O1 C9 C5 114.7(2) . . ? N1 C9 C5 122.2(2) . . ? C9 N1 C10 119.0(2) . . ? C9 N1 C11 125.1(2) . . ? C10 N1 C11 114.8(2) . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? # Attachment 'Br-P2nn.cif' data_delta-(EDT-TTF-CONMe2)2Br_(P2nn,RT) _database_code_depnum_ccdc_archive 'CCDC 727934' _audit_creation_method ; CrysAlis RED (Oxford Diffraction Ltd.), SHELXL-97 and WinGX routine-INITIALISE ; _chemical_name_systematic ; ? ; _chemical_compound_source 'synthesis as described' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C11 H11 N O S6), Br' _chemical_formula_sum 'C22 H22 Br N2 O2 S12' _chemical_formula_weight 811.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0061 0.0029 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -7.7429 0.5071 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0136 0.0059 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0191 0.0108 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1845 0.2085 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2nn _symmetry_space_group_name_Hall 'P -2n 2' _symmetry_Int_Tables_number 34 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, y+1/2, -z+1/2' 'x, -y, -z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 7.1126(5) _cell_length_b 13.0250(7) _cell_length_c 32.7590(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3034.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 59837 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 44.50 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.055 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.775 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1644 _exptl_absorpt_coefficient_mu 2.261 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.467 _exptl_absorpt_correction_T_max 0.918 _exptl_absorpt_process_details ; Scale3AbsPack program, CrysAlis RED, Oxford Diffraction Ltd. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.92072 _diffrn_radiation_type synchrotron _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Cristal beamline, SOLEIL' _diffrn_radiation_detector 'Oxford Diffraction 2D CCD Ruby detector' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Newport 4-circles dirractometer' _diffrn_measurement_method 'combined \f and \w-scans' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 42335 _diffrn_reflns_av_R_equivalents 0.0773 _diffrn_reflns_av_sigmaI/netI 0.0643 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -52 _diffrn_reflns_limit_l_max 52 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 47.69 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 47.69 _diffrn_measured_fraction_theta_full 0.991 _reflns_number_total 12895 _reflns_number_gt 6858 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_structure_solution 'Direct methods (Sir92,Altomare et al.,1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1 (Crystal Impact GbR 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0791P)^2^+0.5750P] 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 0.39(5) _refine_ls_number_reflns 12895 _refine_ls_number_parameters 356 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0962 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1671 _refine_ls_wR_factor_gt 0.1418 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.027 _refine_ls_shift/su_mean 0.005 _refine_diff_density_max 0.868 _refine_diff_density_min -1.197 _refine_diff_density_rms 0.177 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 Br1 Br 0.4999(2) 0.75054(2) 0.000231(9) 0.05860(13) Uani 1 1 d . . . S1 S 0.50131(18) 0.47314(3) 0.784518(13) 0.04764(15) Uani 1 1 d . B . S2 S 0.50009(17) 0.68839(3) 0.809815(12) 0.04158(13) Uani 1 1 d . . . S3 S 0.49949(15) 0.54940(3) 0.688425(13) 0.04171(13) Uani 1 1 d . . . S4 S 0.50279(19) 0.76318(3) 0.717172(13) 0.04993(16) Uani 1 1 d . . . S5 S 0.5020(2) 0.38874(3) 0.867542(16) 0.0696(2) Uani 1 1 d . B . S6 S 0.50129(15) 0.64652(3) 0.898516(12) 0.03738(12) Uani 1 1 d . . . C1 C 0.5013(6) 0.60170(12) 0.76964(4) 0.0371(4) Uani 1 1 d . . . C2 C 0.5041(7) 0.63176(13) 0.73007(5) 0.0397(5) Uani 1 1 d . . . C3 C 0.5076(6) 0.49837(12) 0.83687(5) 0.0373(5) Uani 1 1 d . . . C4 C 0.4994(6) 0.59854(12) 0.84866(4) 0.0345(4) Uani 1 1 d . B . C5 C 0.5048(6) 0.64602(13) 0.65117(5) 0.0396(5) Uani 1 1 d . . . C6 C 0.5019(7) 0.74135(14) 0.66522(5) 0.0500(6) Uani 1 1 d . . . H6 H 0.4993 0.7964 0.6471 0.060 Uiso 1 1 calc R . . C7 C 0.5692(4) 0.43984(17) 0.91641(7) 0.0481(6) Uani 1 1 d D . . H7A H 0.5043 0.3978 0.9364 0.058 Uiso 1 1 calc R A 1 H7B H 0.7017 0.4238 0.9193 0.058 Uiso 1 1 calc R A 1 C8A C 0.5507(7) 0.5377(3) 0.92983(12) 0.0354(4) Uani 0.60 1 d PD B 1 H8A1 H 0.6666 0.5536 0.9441 0.042 Uiso 0.60 1 calc PR B 1 H8A2 H 0.4527 0.5361 0.9504 0.042 Uiso 0.60 1 calc PR B 1 C8B C 0.4463(10) 0.5228(4) 0.92582(18) 0.0354(4) Uani 0.40 1 d PD B 2 H8B1 H 0.4510 0.5352 0.9550 0.042 Uiso 0.40 1 calc PR B 2 H8B2 H 0.3188 0.5025 0.9191 0.042 Uiso 0.40 1 calc PR B 2 C9 C 0.4989(6) 0.59798(15) 0.60991(5) 0.0408(5) Uani 1 1 d . . . O1 O 0.5055(5) 0.50334(11) 0.60873(4) 0.0502(4) Uani 1 1 d . . . N1 N 0.5046(5) 0.65514(13) 0.57521(4) 0.0439(4) Uani 1 1 d . . . C10 C 0.5055(8) 0.6050(2) 0.53510(6) 0.0616(7) Uani 1 1 d . . . H10A H 0.4626 0.5355 0.5379 0.092 Uiso 1 1 calc R . . H10B H 0.6309 0.6052 0.5243 0.092 Uiso 1 1 calc R . . H10C H 0.4236 0.6415 0.5169 0.092 Uiso 1 1 calc R . . C11 C 0.5081(14) 0.76553(18) 0.57397(8) 0.0848(12) Uani 1 1 d . . . H11A H 0.3836 0.7916 0.5785 0.127 Uiso 1 1 calc R . . H11B H 0.5523 0.7878 0.5477 0.127 Uiso 1 1 calc R . . H11C H 0.5908 0.7908 0.5948 0.127 Uiso 1 1 calc R . . S21 S 0.50128(18) 1.02637(3) 0.215542(13) 0.04780(15) Uani 1 1 d . D . S22 S 0.50019(18) 0.81230(3) 0.190272(12) 0.04443(14) Uani 1 1 d . . . S23 S 0.49900(14) 0.95038(3) 0.311458(12) 0.03765(12) Uani 1 1 d . . . S24 S 0.5026(2) 0.73829(4) 0.282957(14) 0.05402(17) Uani 1 1 d . . . S25 S 0.5027(2) 1.11141(3) 0.132200(15) 0.0693(2) Uani 1 1 d . D . S26 S 0.50156(16) 0.85237(3) 0.101386(12) 0.04026(13) Uani 1 1 d . . . C21 C 0.5001(6) 0.89973(13) 0.22984(5) 0.0390(5) Uani 1 1 d . . . C22 C 0.5006(6) 0.86650(12) 0.27023(4) 0.0329(4) Uani 1 1 d . . . C23 C 0.5075(7) 1.00324(14) 0.16297(5) 0.0432(5) Uani 1 1 d . . . C24 C 0.5018(6) 0.90386(11) 0.15086(5) 0.0328(4) Uani 1 1 d . D . C25 C 0.5018(5) 0.85373(12) 0.34883(4) 0.0314(4) Uani 1 1 d . . . C26 C 0.5031(6) 0.75378(13) 0.33514(5) 0.0435(5) Uani 1 1 d . . . H26 H 0.5043 0.6982 0.3530 0.052 Uiso 1 1 calc R . . C27 C 0.5660(4) 1.05843(16) 0.08420(6) 0.0427(5) Uani 1 1 d D . . H27A H 0.5498 1.1114 0.0637 0.051 Uiso 1 1 calc R C 1 H27B H 0.6989 1.0418 0.0851 0.051 Uiso 1 1 calc R C 1 C28A C 0.4701(9) 0.9721(3) 0.07127(14) 0.0354(4) Uani 0.50 1 d PD D 1 H28A H 0.5075 0.9579 0.0434 0.042 Uiso 0.50 1 calc PR D 1 H28B H 0.3370 0.9883 0.0709 0.042 Uiso 0.50 1 calc PR D 1 C28B C 0.5600(8) 0.9625(3) 0.07214(16) 0.0354(4) Uani 0.50 1 d PD D 2 H28C H 0.6837 0.9484 0.0610 0.042 Uiso 0.50 1 calc PR D 2 H28D H 0.4742 0.9617 0.0491 0.042 Uiso 0.50 1 calc PR D 2 C29 C 0.4980(6) 0.90154(12) 0.39051(5) 0.0340(4) Uani 1 1 d . . . O21 O 0.5019(5) 0.99689(10) 0.39012(4) 0.0476(4) Uani 1 1 d . . . N21 N 0.5016(5) 0.84598(14) 0.42414(5) 0.0493(4) Uani 1 1 d . . . C30 C 0.5065(8) 0.8984(2) 0.46335(6) 0.0601(7) Uani 1 1 d . . . H30A H 0.4658 0.9682 0.4599 0.090 Uiso 1 1 calc R . . H30B H 0.6325 0.8977 0.4738 0.090 Uiso 1 1 calc R . . H30C H 0.4244 0.8641 0.4822 0.090 Uiso 1 1 calc R . . C31 C 0.5092(14) 0.73259(19) 0.42646(8) 0.0841(12) Uani 1 1 d . . . H31A H 0.3865 0.7048 0.4212 0.126 Uiso 1 1 calc R . . H31B H 0.5498 0.7123 0.4532 0.126 Uiso 1 1 calc R . . H31C H 0.5962 0.7071 0.4065 0.126 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 Br1 0.0993(3) 0.0459(2) 0.03058(18) -0.00114(14) 0.0006(2) -0.0001(2) S1 0.0884(4) 0.0301(2) 0.0244(2) -0.00640(14) 0.0021(5) -0.0006(5) S2 0.0773(4) 0.02484(17) 0.02261(19) -0.00326(13) 0.0028(4) 0.0001(5) S3 0.0664(4) 0.0349(2) 0.02377(19) -0.00455(15) 0.0034(4) -0.0014(5) S4 0.0960(5) 0.02958(19) 0.0242(2) -0.00565(15) 0.0012(5) -0.0026(5) S5 0.1517(7) 0.02294(19) 0.0341(2) 0.00115(16) -0.0009(8) -0.0002(6) S6 0.0624(3) 0.02855(18) 0.02117(17) -0.00273(13) 0.0007(4) -0.0004(3) C1 0.0628(14) 0.0346(8) 0.0138(6) -0.0016(5) -0.0057(13) 0.0062(14) C2 0.0627(14) 0.0330(7) 0.0234(7) 0.0008(6) -0.0105(14) -0.0013(16) C3 0.0648(14) 0.0238(6) 0.0232(7) 0.0019(5) -0.0030(14) 0.0102(14) C4 0.0498(12) 0.0349(8) 0.0188(6) -0.0064(5) 0.0031(14) 0.0101(14) C5 0.0567(14) 0.0402(9) 0.0219(7) 0.0068(6) -0.0020(15) 0.0138(14) C6 0.0864(18) 0.0379(9) 0.0257(8) -0.0039(6) -0.0087(18) 0.0103(19) C7 0.0667(16) 0.0364(10) 0.0411(11) 0.0021(8) -0.0041(11) 0.0052(11) C8A 0.0515(13) 0.0312(8) 0.0234(6) 0.0002(6) -0.0096(10) -0.0088(11) C8B 0.0515(13) 0.0312(8) 0.0234(6) 0.0002(6) -0.0096(10) -0.0088(11) C9 0.0477(13) 0.0542(10) 0.0205(7) -0.0139(7) 0.0072(14) -0.0027(17) O1 0.0730(11) 0.0463(7) 0.0314(6) -0.0114(6) -0.0008(13) 0.0084(14) N1 0.0628(12) 0.0500(9) 0.0188(6) 0.0020(6) 0.0025(13) 0.0119(16) C10 0.0847(19) 0.0764(16) 0.0237(9) -0.0144(9) -0.0031(19) -0.017(2) C11 0.167(4) 0.0480(12) 0.0390(12) 0.0136(10) -0.017(3) -0.004(3) S21 0.0879(4) 0.0296(2) 0.0258(2) -0.00600(14) 0.0010(5) -0.0023(5) S22 0.0826(4) 0.03100(19) 0.01967(18) -0.00099(14) -0.0002(4) -0.0020(5) S23 0.0620(3) 0.02950(18) 0.02142(18) -0.00309(13) 0.0064(4) -0.0038(5) S24 0.1004(5) 0.0351(2) 0.0266(2) -0.00527(16) 0.0061(5) 0.0080(5) S25 0.1504(7) 0.0282(2) 0.0294(2) -0.00217(16) 0.0018(7) 0.0021(6) S26 0.0708(4) 0.02842(18) 0.02154(18) -0.00218(14) 0.0051(4) -0.0054(4) C21 0.0548(13) 0.0315(8) 0.0308(8) -0.0074(6) 0.0051(13) -0.0241(13) C22 0.0451(11) 0.0345(7) 0.0193(6) -0.0076(5) 0.0017(13) -0.0004(14) C23 0.0716(16) 0.0335(8) 0.0246(8) -0.0064(6) 0.0108(15) 0.0024(16) C24 0.0525(13) 0.0225(6) 0.0235(7) 0.0023(5) 0.0079(15) 0.0060(13) C25 0.0381(10) 0.0342(7) 0.0220(7) -0.0102(5) -0.0056(14) 0.0060(12) C26 0.0734(16) 0.0329(8) 0.0242(7) 0.0024(6) 0.0079(16) 0.0182(16) C27 0.0662(15) 0.0365(10) 0.0255(9) 0.0072(7) -0.0056(9) -0.0014(10) C28A 0.0515(13) 0.0312(8) 0.0234(6) 0.0002(6) -0.0096(10) -0.0088(11) C28B 0.0515(13) 0.0312(8) 0.0234(6) 0.0002(6) -0.0096(10) -0.0088(11) C29 0.0415(11) 0.0350(7) 0.0256(7) 0.0053(6) 0.0041(13) 0.0058(14) O21 0.0765(11) 0.0376(6) 0.0287(6) -0.0060(5) 0.0061(13) -0.0097(13) N21 0.0690(12) 0.0529(9) 0.0259(7) -0.0052(7) -0.0041(15) 0.0067(17) C30 0.0850(19) 0.0748(15) 0.0204(8) 0.0012(8) 0.0081(19) -0.007(2) C31 0.163(4) 0.0532(13) 0.0362(11) 0.0056(10) -0.009(3) -0.016(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 C1 1.7440(17) . ? S1 C3 1.7467(16) . ? S2 C4 1.7288(17) . ? S2 C1 1.7341(15) . ? S3 C2 1.7358(17) . ? S3 C5 1.7535(17) . ? S4 C6 1.7253(18) . ? S4 C2 1.7632(17) . ? S5 C3 1.7465(17) . ? S5 C7 1.798(2) . ? S6 C4 1.7488(15) . ? S6 C8A 1.784(4) . ? S6 C8B 1.884(6) . ? C1 C2 1.354(2) . ? C3 C4 1.362(2) . ? C5 C6 1.324(2) . ? C5 C9 1.490(2) . ? C6 H6 0.9300 . ? C7 C8A 1.355(4) . ? C7 C8B 1.423(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C8B H8B1 0.9700 . ? C8B H8B2 0.9700 . ? C9 O1 1.234(2) . ? C9 N1 1.359(2) . ? N1 C11 1.439(3) . ? N1 C10 1.467(2) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? S21 C21 1.7147(18) . ? S21 C23 1.7490(17) . ? S22 C21 1.7253(16) . ? S22 C24 1.7575(15) . ? S23 C22 1.7372(14) . ? S23 C25 1.7561(17) . ? S24 C26 1.7213(17) . ? S24 C22 1.7214(17) . ? S25 C23 1.7326(19) . ? S25 C27 1.775(2) . ? S26 C24 1.7542(15) . ? S26 C28B 1.774(5) . ? S26 C28A 1.859(5) . ? C21 C22 1.392(2) . ? C23 C24 1.354(2) . ? C25 C26 1.377(2) . ? C25 C29 1.501(2) . ? C26 H26 0.9300 . ? C27 C28B 1.311(5) . ? C27 C28A 1.382(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28A H28A 0.9700 . ? C28A H28B 0.9700 . ? C28B H28C 0.9700 . ? C28B H28D 0.9700 . ? C29 O21 1.242(2) . ? C29 N21 1.318(2) . ? N21 C30 1.455(2) . ? N21 C31 1.480(3) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C3 95.39(7) . . ? C4 S2 C1 96.77(8) . . ? C2 S3 C5 95.92(8) . . ? C6 S4 C2 94.38(8) . . ? C3 S5 C7 101.74(10) . . ? C4 S6 C8A 104.74(13) . . ? C4 S6 C8B 97.82(18) . . ? C2 C1 S2 122.57(13) . . ? C2 C1 S1 123.04(12) . . ? S2 C1 S1 114.39(8) . . ? C1 C2 S3 124.98(13) . . ? C1 C2 S4 120.67(13) . . ? S3 C2 S4 114.30(9) . . ? C4 C3 S5 128.25(13) . . ? C4 C3 S1 117.23(12) . . ? S5 C3 S1 114.24(9) . . ? C3 C4 S2 116.08(12) . . ? C3 C4 S6 127.37(13) . . ? S2 C4 S6 116.45(9) . . ? C6 C5 C9 135.12(17) . . ? C6 C5 S3 115.49(14) . . ? C9 C5 S3 109.23(13) . . ? C5 C6 S4 119.83(15) . . ? C5 C6 H6 120.1 . . ? S4 C6 H6 120.1 . . ? C8A C7 S5 127.7(2) . . ? C8B C7 S5 108.1(3) . . ? C8A C7 H7A 105.4 . . ? C8B C7 H7A 89.4 . . ? S5 C7 H7A 105.4 . . ? C8A C7 H7B 105.4 . . ? C8B C7 H7B 137.6 . . ? S5 C7 H7B 105.4 . . ? H7A C7 H7B 106.0 . . ? C7 C8A S6 125.4(3) . . ? C7 C8A H8A1 106.0 . . ? S6 C8A H8A1 106.0 . . ? C7 C8A H8A2 106.0 . . ? S6 C8A H8A2 106.0 . . ? H8A1 C8A H8A2 106.3 . . ? C7 C8B S6 114.8(4) . . ? C7 C8B H8B1 108.6 . . ? S6 C8B H8B1 108.6 . . ? C7 C8B H8B2 108.6 . . ? S6 C8B H8B2 108.6 . . ? H8B1 C8B H8B2 107.6 . . ? O1 C9 N1 121.31(15) . . ? O1 C9 C5 116.53(17) . . ? N1 C9 C5 121.85(17) . . ? C9 N1 C11 124.86(17) . . ? C9 N1 C10 120.33(18) . . ? C11 N1 C10 114.80(18) . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C21 S21 C23 95.93(8) . . ? C21 S22 C24 95.97(8) . . ? C22 S23 C25 95.23(7) . . ? C26 S24 C22 97.29(8) . . ? C23 S25 C27 101.20(9) . . ? C24 S26 C28B 100.93(17) . . ? C24 S26 C28A 99.78(16) . . ? C22 C21 S21 123.96(12) . . ? C22 C21 S22 120.59(13) . . ? S21 C21 S22 115.45(10) . . ? C21 C22 S24 122.13(12) . . ? C21 C22 S23 122.92(13) . . ? S24 C22 S23 114.95(9) . . ? C24 C23 S25 127.32(14) . . ? C24 C23 S21 116.88(13) . . ? S25 C23 S21 115.61(10) . . ? C23 C24 S26 129.49(12) . . ? C23 C24 S22 115.70(12) . . ? S26 C24 S22 114.79(8) . . ? C26 C25 C29 133.52(15) . . ? C26 C25 S23 116.80(12) . . ? C29 C25 S23 109.66(11) . . ? C25 C26 S24 115.74(13) . . ? C25 C26 H26 122.1 . . ? S24 C26 H26 122.1 . . ? C28B C27 S25 129.0(3) . . ? C28A C27 S25 117.6(3) . . ? C28B C27 H27A 117.7 . . ? C28A C27 H27A 107.9 . . ? S25 C27 H27A 107.9 . . ? C28B C27 H27B 80.0 . . ? C28A C27 H27B 107.9 . . ? S25 C27 H27B 107.9 . . ? H27A C27 H27B 107.2 . . ? C27 C28A S26 117.4(3) . . ? C27 C28A H28A 107.9 . . ? S26 C28A H28A 107.9 . . ? C27 C28A H28B 107.9 . . ? S26 C28A H28B 107.9 . . ? H28A C28A H28B 107.2 . . ? C27 C28B S26 128.0(4) . . ? C27 C28B H28C 105.3 . . ? S26 C28B H28C 105.3 . . ? C27 C28B H28D 105.3 . . ? S26 C28B H28D 105.3 . . ? H28C C28B H28D 106.0 . . ? O21 C29 N21 123.84(17) . . ? O21 C29 C25 113.90(14) . . ? N21 C29 C25 122.14(15) . . ? C29 N21 C30 118.70(18) . . ? C29 N21 C31 126.27(17) . . ? C30 N21 C31 114.98(18) . . ? N21 C30 H30A 109.5 . . ? N21 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N21 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N21 C31 H31A 109.5 . . ? N21 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N21 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ?