# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Richard Oakley' _publ_contact_author_email oakley@sciborg.uwaterloo.ca _publ_section_title ; The first semiquinone-bridged bisdithiazolyl radical conductor: a canted antiferromagnet displaying a spin-flop transition ; loop_ _publ_author_name R.Oakley 'Xin Yu' A.Mailman P.Dube A.Assoud # Attachment '- XY_3_21_0m.cif' data_xy_3_21_0m _database_code_depnum_ccdc_archive 'CCDC 810524' #TrackingRef '- XY_3_21_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H5 F3 N2 O4 S5' _chemical_formula_weight 470.49 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 8.4534(4) _cell_length_b 12.9782(6) _cell_length_c 16.2121(7) _cell_angle_alpha 90.00 _cell_angle_beta 102.7620(10) _cell_angle_gamma 90.00 _cell_volume 1734.69(14) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.802 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.723 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8287 _exptl_absorpt_correction_T_max 0.9118 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22230 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4183 _reflns_number_gt 3525 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0138P)^2^+0.8454P] 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 SHELXL _refine_ls_extinction_coef 0.0081(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4183 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0758 _refine_ls_wR_factor_gt 0.0721 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.164 _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 S1 S 0.82979(9) 0.84481(6) 0.64019(4) 0.0807(2) Uani 1 1 d . . . S2 S 0.86255(7) 0.87339(5) 0.76741(3) 0.06206(17) Uani 1 1 d . . . S3 S 0.20926(7) 0.65675(6) 0.86133(4) 0.06857(18) Uani 1 1 d . . . S4 S 0.40341(6) 0.73938(5) 0.93029(3) 0.05749(16) Uani 1 1 d . . . N1 N 0.6623(2) 0.78287(16) 0.62686(10) 0.0639(5) Uani 1 1 d . . . N2 N 0.25938(19) 0.65855(14) 0.77113(11) 0.0563(4) Uani 1 1 d . . . O1 O 0.37368(18) 0.67475(14) 0.62188(9) 0.0681(4) Uani 1 1 d . . . C6 C 0.6021(2) 0.76968(16) 0.69373(11) 0.0465(4) Uani 1 1 d . . . C1 C 0.4476(2) 0.71226(16) 0.68694(11) 0.0480(4) Uani 1 1 d . . . C2 C 0.3929(2) 0.70666(15) 0.76829(11) 0.0442(4) Uani 1 1 d . . . C3 C 0.4877(2) 0.75401(14) 0.84425(11) 0.0408(4) Uani 1 1 d . . . C4 C 0.6335(2) 0.80437(14) 0.84839(10) 0.0396(4) Uani 1 1 d . . . C5 C 0.6870(2) 0.81178(14) 0.77316(11) 0.0426(4) Uani 1 1 d . . . C7 C 0.7330(2) 0.84627(15) 0.92866(10) 0.0412(4) Uani 1 1 d . . . C8 C 0.6795(3) 0.92741(18) 0.97035(14) 0.0618(6) Uani 1 1 d . . . H8A H 0.5799 0.9581 0.9478 0.074 Uiso 1 1 calc R . . C9 C 0.7743(4) 0.9631(2) 1.04593(16) 0.0794(8) Uani 1 1 d . . . H9A H 0.7371 1.0169 1.0745 0.095 Uiso 1 1 calc R . . C10 C 0.9216(3) 0.9198(2) 1.07850(15) 0.0772(8) Uani 1 1 d . . . H10A H 0.9844 0.9441 1.1293 0.093 Uiso 1 1 calc R . . C11 C 0.9777(3) 0.8409(2) 1.03705(15) 0.0673(6) Uani 1 1 d . . . H11A H 1.0793 0.8126 1.0590 0.081 Uiso 1 1 calc R . . C12 C 0.8834(2) 0.80319(17) 0.96240(12) 0.0513(5) Uani 1 1 d . . . H12A H 0.9210 0.7487 0.9348 0.062 Uiso 1 1 calc R . . S5 S 0.23207(6) 0.99659(4) 0.69932(3) 0.05003(13) Uani 1 1 d . A . C13 C 0.2600(4) 0.9831(2) 0.59313(18) 0.0798(8) Uani 1 1 d . . . F1 F 0.2636(4) 1.06435(16) 0.55316(12) 0.1303(8) Uani 1 1 d . A . F2 F 0.2679(13) 0.8995(5) 0.5657(5) 0.153(4) Uani 0.60 1 d P A 1 F3 F 0.0856(9) 1.0004(9) 0.5439(4) 0.123(3) Uani 0.30 1 d P A 2 F4 F 0.424(3) 1.0066(12) 0.601(2) 0.141(10) Uani 0.17 1 d P A . F5 F 0.4291(11) 0.9564(7) 0.6021(6) 0.140(3) Uani 0.48 1 d P A . F6 F 0.1691(17) 0.9146(8) 0.5492(7) 0.165(6) Uani 0.45 1 d P A . O2 O 0.1817(6) 0.9016(4) 0.7213(3) 0.0978(16) Uani 0.60 1 d P . . O3 O 0.3955(5) 1.0205(5) 0.7402(2) 0.1233(17) Uani 0.60 1 d P . . O5 O 0.1361(8) 1.0838(4) 0.7013(3) 0.0967(15) Uani 0.48 1 d P . . O6 O 0.0559(5) 1.0031(5) 0.6777(3) 0.0995(15) Uani 0.48 1 d P A . O7 O 0.2821(11) 1.0924(4) 0.7259(4) 0.106(2) Uani 0.42 1 d P A . O8 O 0.2900(11) 0.9095(6) 0.7433(5) 0.139(4) Uani 0.42 1 d P A . 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 0.0962(5) 0.1079(5) 0.0472(3) -0.0182(3) 0.0357(3) -0.0395(4) S2 0.0666(3) 0.0784(4) 0.0461(3) -0.0160(3) 0.0229(2) -0.0287(3) S3 0.0495(3) 0.0898(5) 0.0693(4) -0.0075(3) 0.0192(3) -0.0172(3) S4 0.0497(3) 0.0818(4) 0.0435(3) -0.0043(3) 0.0158(2) -0.0087(3) N1 0.0735(12) 0.0824(13) 0.0371(9) -0.0093(9) 0.0147(8) -0.0135(10) N2 0.0418(9) 0.0659(11) 0.0579(10) -0.0061(9) 0.0039(7) -0.0060(8) O1 0.0602(9) 0.0945(12) 0.0421(8) -0.0167(8) -0.0046(7) -0.0112(8) C6 0.0496(10) 0.0567(11) 0.0310(8) -0.0032(8) 0.0044(7) -0.0002(9) C1 0.0441(10) 0.0579(12) 0.0371(9) -0.0035(8) -0.0014(8) 0.0018(9) C2 0.0355(9) 0.0511(11) 0.0420(9) -0.0027(8) 0.0001(7) 0.0025(8) C3 0.0369(9) 0.0488(10) 0.0351(8) 0.0008(7) 0.0045(7) 0.0042(7) C4 0.0371(9) 0.0485(10) 0.0316(8) -0.0019(7) 0.0041(7) 0.0020(7) C5 0.0418(9) 0.0492(10) 0.0357(9) -0.0032(8) 0.0060(7) -0.0023(8) C7 0.0404(9) 0.0512(10) 0.0312(8) -0.0020(7) 0.0061(7) -0.0055(8) C8 0.0615(13) 0.0659(14) 0.0549(12) -0.0143(11) 0.0059(10) 0.0057(11) C9 0.101(2) 0.0732(17) 0.0607(15) -0.0294(13) 0.0100(14) -0.0065(15) C10 0.0864(18) 0.0847(18) 0.0496(13) -0.0128(13) -0.0085(12) -0.0300(15) C11 0.0496(12) 0.0864(17) 0.0559(13) 0.0071(12) -0.0100(10) -0.0153(12) C12 0.0414(10) 0.0652(13) 0.0445(10) -0.0011(9) 0.0034(8) -0.0021(9) S5 0.0500(3) 0.0480(3) 0.0508(3) 0.0030(2) 0.0083(2) -0.0011(2) C13 0.116(2) 0.0602(16) 0.0732(17) 0.0007(13) 0.0430(17) -0.0044(16) F1 0.226(3) 0.0969(14) 0.0818(12) 0.0230(10) 0.0629(15) -0.0020(17) F2 0.300(12) 0.081(3) 0.104(5) -0.019(3) 0.098(7) 0.042(6) F3 0.091(4) 0.193(9) 0.062(4) -0.014(5) -0.028(3) -0.004(5) F4 0.121(14) 0.074(9) 0.28(2) -0.015(12) 0.162(17) -0.007(9) F5 0.125(5) 0.163(8) 0.161(6) 0.035(6) 0.092(5) 0.083(6) F6 0.270(14) 0.153(10) 0.077(4) -0.052(7) 0.050(8) -0.132(10) O2 0.142(4) 0.079(3) 0.081(3) 0.005(2) 0.044(3) -0.048(3) O3 0.079(2) 0.188(5) 0.086(3) 0.028(3) -0.019(2) -0.058(3) O5 0.117(4) 0.087(3) 0.098(3) 0.015(3) 0.048(3) 0.050(3) O6 0.048(2) 0.162(5) 0.093(3) 0.012(3) 0.025(2) 0.011(3) O7 0.158(6) 0.076(4) 0.098(4) -0.040(3) 0.054(4) -0.058(4) O8 0.210(9) 0.105(6) 0.093(5) 0.041(4) 0.013(6) 0.089(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 N1 1.601(2) . ? S1 S2 2.0533(8) . ? S2 C5 1.7061(19) . ? S3 N2 1.6101(19) . ? S3 S4 2.0695(8) . ? S4 C3 1.7113(18) . ? N1 C6 1.306(2) . ? N2 C2 1.300(2) . ? O1 C1 1.204(2) . ? C6 C5 1.437(2) . ? C6 C1 1.486(3) . ? C1 C2 1.493(3) . ? C2 C3 1.449(2) . ? C3 C4 1.384(2) . ? C4 C5 1.395(2) . ? C4 C7 1.488(2) . ? C7 C8 1.381(3) . ? C7 C12 1.386(3) . ? C8 C9 1.388(3) . ? C9 C10 1.362(4) . ? C10 C11 1.366(4) . ? C11 C12 1.384(3) . ? S5 O7 1.353(4) . ? S5 O8 1.368(6) . ? S5 O2 1.376(4) . ? S5 O5 1.397(4) . ? S5 O3 1.429(3) . ? S5 O6 1.455(4) . ? S5 C13 1.797(3) . ? C13 F2 1.179(6) . ? C13 F1 1.242(3) . ? C13 F6 1.283(8) . ? C13 F4 1.397(19) . ? C13 F5 1.447(8) . ? C13 F3 1.530(7) . ? F1 F4 1.59(2) . ? F1 F3 1.696(9) . ? F2 F6 0.842(16) . ? F2 F5 1.547(12) . ? F3 F6 1.311(12) . ? F4 F5 0.653(15) . ? O2 O8 0.912(9) . ? O2 O6 1.742(7) . ? O3 O7 1.321(8) . ? O3 O8 1.701(10) . ? O5 O7 1.215(8) . ? O5 O6 1.261(7) . ? 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 98.35(7) . . ? C5 S2 S1 92.54(6) . . ? N2 S3 S4 98.44(7) . . ? C3 S4 S3 92.32(7) . . ? C6 N1 S1 116.66(15) . . ? C2 N2 S3 116.36(14) . . ? N1 C6 C5 119.01(18) . . ? N1 C6 C1 120.07(17) . . ? C5 C6 C1 120.92(16) . . ? O1 C1 C6 123.06(18) . . ? O1 C1 C2 123.51(19) . . ? C6 C1 C2 113.43(15) . . ? N2 C2 C3 119.67(17) . . ? N2 C2 C1 119.72(17) . . ? C3 C2 C1 120.61(16) . . ? C4 C3 C2 124.11(16) . . ? C4 C3 S4 122.66(13) . . ? C2 C3 S4 113.21(14) . . ? C3 C4 C5 116.60(16) . . ? C3 C4 C7 122.73(15) . . ? C5 C4 C7 120.65(16) . . ? C4 C5 C6 124.29(17) . . ? C4 C5 S2 122.28(14) . . ? C6 C5 S2 113.43(14) . . ? C8 C7 C12 119.08(18) . . ? C8 C7 C4 121.59(17) . . ? C12 C7 C4 119.33(17) . . ? C7 C8 C9 119.9(2) . . ? C10 C9 C8 120.3(2) . . ? C9 C10 C11 120.4(2) . . ? C10 C11 C12 120.0(2) . . ? C11 C12 C7 120.2(2) . . ? O7 S5 O8 122.9(5) . . ? O7 S5 O2 146.5(3) . . ? O8 S5 O2 38.8(4) . . ? O7 S5 O5 52.4(4) . . ? O8 S5 O5 143.1(4) . . ? O2 S5 O5 120.4(4) . . ? O7 S5 O3 56.6(4) . . ? O8 S5 O3 74.9(4) . . ? O2 S5 O3 113.4(3) . . ? O5 S5 O3 108.7(4) . . ? O7 S5 O6 104.8(4) . . ? O8 S5 O6 113.8(5) . . ? O2 S5 O6 75.9(3) . . ? O5 S5 O6 52.4(3) . . ? O3 S5 O6 158.9(3) . . ? O7 S5 C13 107.3(2) . . ? O8 S5 C13 108.2(4) . . ? O2 S5 C13 105.9(2) . . ? O5 S5 C13 107.5(2) . . ? O3 S5 C13 98.5(2) . . ? O6 S5 C13 96.8(2) . . ? F2 C13 F1 125.1(5) . . ? F2 C13 F6 39.7(7) . . ? F1 C13 F6 112.3(6) . . ? F2 C13 F4 95.6(8) . . ? F1 C13 F4 73.9(9) . . ? F6 C13 F4 131.4(11) . . ? F2 C13 F5 71.4(5) . . ? F1 C13 F5 96.8(4) . . ? F6 C13 F5 110.3(7) . . ? F4 C13 F5 26.5(6) . . ? F2 C13 F3 93.8(6) . . ? F1 C13 F3 74.6(4) . . ? F6 C13 F3 54.7(6) . . ? F4 C13 F3 146.8(12) . . ? F5 C13 F3 154.7(5) . . ? F2 C13 S5 118.7(5) . . ? F1 C13 S5 116.2(2) . . ? F6 C13 S5 114.2(6) . . ? F4 C13 S5 103.3(12) . . ? F5 C13 S5 105.3(4) . . ? F3 C13 S5 99.8(3) . . ? C13 F1 F4 57.5(6) . . ? C13 F1 F3 60.5(3) . . ? F4 F1 F3 117.1(6) . . ? F6 F2 C13 76.8(8) . . ? F6 F2 F5 137.7(11) . . ? C13 F2 F5 62.4(4) . . ? F6 F3 C13 53.0(4) . . ? F6 F3 F1 87.5(6) . . ? C13 F3 F1 44.9(2) . . ? F5 F4 C13 81(2) . . ? F5 F4 F1 122(4) . . ? C13 F4 F1 48.6(8) . . ? F4 F5 C13 72(2) . . ? F4 F5 F2 115(3) . . ? C13 F5 F2 46.2(4) . . ? F2 F6 C13 63.5(8) . . ? F2 F6 F3 134.4(12) . . ? C13 F6 F3 72.3(6) . . ? O8 O2 S5 70.1(6) . . ? O8 O2 O6 122.9(7) . . ? S5 O2 O6 54.1(2) . . ? O7 O3 S5 58.8(3) . . ? O7 O3 O8 103.8(4) . . ? S5 O3 O8 50.9(2) . . ? O7 O5 O6 127.9(5) . . ? O7 O5 S5 61.9(3) . . ? O6 O5 S5 66.1(3) . . ? O5 O6 S5 61.4(3) . . ? O5 O6 O2 105.4(3) . . ? S5 O6 O2 50.03(18) . . ? O5 O7 O3 129.7(5) . . ? O5 O7 S5 65.7(3) . . ? O3 O7 S5 64.6(3) . . ? O2 O8 S5 71.1(5) . . ? O2 O8 O3 124.9(7) . . ? S5 O8 O3 54.2(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.266 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.042 # Attachment '- XY_3_32_0m.cif' data_xy_3_32_0m _database_code_depnum_ccdc_archive 'CCDC 810525' #TrackingRef '- XY_3_32_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H5 N2 O S4' _chemical_formula_weight 321.42 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2_12_12_1 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' _cell_length_a 6.8011(7) _cell_length_b 11.3785(12) _cell_length_c 15.6252(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1209.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.766 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 0.774 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7787 _exptl_absorpt_correction_T_max 0.9847 _exptl_absorpt_process_details APEXII _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7891 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0675 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3431 _reflns_number_gt 2505 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0018P)^2^+0.7165P] 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 contr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00190(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(13) _refine_ls_number_reflns 3431 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0818 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0739 _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_restrained_S_all 1.126 _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 0.46322(18) 0.86271(8) 0.33077(6) 0.0397(2) Uani 1 1 d . . . S2 S 0.46431(18) 0.67786(8) 0.33540(6) 0.0381(2) Uani 1 1 d . . . S3 S 0.4530(2) 0.58297(9) 0.76120(6) 0.0411(3) Uani 1 1 d . . . S4 S 0.4504(2) 0.47018(7) 0.65607(6) 0.0406(3) Uani 1 1 d . . . O1 O 0.4809(5) 0.9076(2) 0.61103(16) 0.0411(7) Uani 1 1 d . . . N1 N 0.4663(6) 0.8905(2) 0.43338(18) 0.0355(7) Uani 1 1 d . . . N2 N 0.4614(6) 0.7065(2) 0.71063(17) 0.0352(7) Uani 1 1 d . . . C1 C 0.4716(6) 0.8108(3) 0.5771(2) 0.0292(8) Uani 1 1 d . . . C2 C 0.4620(6) 0.7005(3) 0.6262(2) 0.0275(7) Uani 1 1 d . . . C3 C 0.4555(6) 0.5881(3) 0.5844(2) 0.0292(7) Uani 1 1 d . . . C4 C 0.4565(7) 0.5757(3) 0.4957(2) 0.0275(7) Uani 1 1 d . . . C5 C 0.4646(6) 0.6803(3) 0.4470(2) 0.0293(7) Uani 1 1 d . . . C6 C 0.4680(6) 0.7950(3) 0.4831(2) 0.0288(7) Uani 1 1 d . . . C7 C 0.4428(6) 0.4579(3) 0.4551(2) 0.0291(8) Uani 1 1 d . . . C8 C 0.2740(6) 0.3903(3) 0.4662(2) 0.0355(9) Uani 1 1 d . . . H8A H 0.1696 0.4198 0.4980 0.043 Uiso 1 1 calc R . . C9 C 0.2605(7) 0.2787(3) 0.4299(2) 0.0416(10) Uani 1 1 d . . . H9A H 0.1469 0.2342 0.4367 0.050 Uiso 1 1 calc R . . C10 C 0.4182(7) 0.2346(3) 0.3836(2) 0.0454(12) Uani 1 1 d . . . H10A H 0.4109 0.1597 0.3600 0.054 Uiso 1 1 calc R . . C11 C 0.5842(7) 0.3007(3) 0.3723(2) 0.0424(11) Uani 1 1 d . . . H11A H 0.6889 0.2704 0.3410 0.051 Uiso 1 1 calc R . . C12 C 0.5975(6) 0.4130(3) 0.4074(2) 0.0370(10) Uani 1 1 d . . . H12A H 0.7102 0.4579 0.3988 0.044 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0476(6) 0.0343(4) 0.0370(5) 0.0096(4) -0.0030(6) -0.0036(5) S2 0.0500(6) 0.0341(5) 0.0301(5) 0.0012(4) 0.0014(6) -0.0021(5) S3 0.0584(7) 0.0374(5) 0.0275(5) 0.0028(4) -0.0011(6) 0.0022(6) S4 0.0618(7) 0.0269(4) 0.0332(5) 0.0027(4) 0.0025(6) 0.0030(5) O1 0.055(2) 0.0233(11) 0.0452(15) -0.0069(12) -0.0002(16) 0.0007(14) N1 0.043(2) 0.0261(14) 0.0379(17) 0.0030(13) -0.0028(18) -0.0042(16) N2 0.046(2) 0.0314(15) 0.0285(15) -0.0065(13) -0.0017(17) -0.0013(18) C1 0.029(2) 0.0249(15) 0.0338(19) -0.0036(15) 0.0005(18) 0.0000(17) C2 0.0287(19) 0.0264(16) 0.0275(16) -0.0016(14) -0.0010(19) 0.0027(17) C3 0.034(2) 0.0208(14) 0.0330(18) 0.0009(14) 0.0002(19) 0.0011(19) C4 0.035(2) 0.0223(15) 0.0250(17) -0.0006(13) 0.0018(18) 0.0010(18) C5 0.0309(19) 0.0283(16) 0.0287(17) 0.0004(14) 0.0007(19) -0.0011(18) C6 0.0290(19) 0.0232(15) 0.0342(18) 0.0031(15) -0.0007(19) -0.0012(16) C7 0.039(2) 0.0236(16) 0.0245(17) 0.0007(14) 0.0002(18) -0.0003(18) C8 0.046(3) 0.031(2) 0.030(2) 0.0001(17) 0.0011(19) -0.0027(18) C9 0.059(3) 0.028(2) 0.037(2) -0.0004(19) -0.003(2) -0.011(2) C10 0.085(4) 0.0223(17) 0.029(2) -0.0022(16) 0.001(2) -0.005(2) C11 0.065(3) 0.0302(19) 0.032(2) -0.0030(18) 0.009(2) 0.008(2) C12 0.047(3) 0.0291(19) 0.035(2) -0.0036(18) 0.0058(19) -0.0005(18) _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 1.634(3) . ? S1 S2 2.1046(12) . ? S2 C5 1.745(3) . ? S3 N2 1.614(3) . ? S3 S4 2.0847(13) . ? S4 C3 1.749(3) . ? O1 C1 1.225(4) . ? N1 C6 1.336(4) . ? N2 C2 1.320(4) . ? C1 C2 1.473(4) . ? C1 C6 1.479(5) . ? C2 C3 1.437(4) . ? C3 C4 1.393(4) . ? C4 C5 1.413(4) . ? C4 C7 1.485(4) . ? C5 C6 1.423(4) . ? C7 C12 1.387(5) . ? C7 C8 1.393(5) . ? C8 C9 1.393(5) . ? C9 C10 1.388(6) . ? C10 C11 1.367(6) . ? C11 C12 1.394(5) . ? 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 99.18(11) . . ? C5 S2 S1 91.07(12) . . ? N2 S3 S4 98.68(11) . . ? C3 S4 S3 91.84(11) . . ? C6 N1 S1 114.5(2) . . ? C2 N2 S3 116.3(2) . . ? O1 C1 C2 122.9(3) . . ? O1 C1 C6 122.7(3) . . ? C2 C1 C6 114.4(3) . . ? N2 C2 C3 120.1(3) . . ? N2 C2 C1 118.5(3) . . ? C3 C2 C1 121.5(3) . . ? C4 C3 C2 122.9(3) . . ? C4 C3 S4 124.0(3) . . ? C2 C3 S4 113.1(2) . . ? C3 C4 C5 116.7(3) . . ? C3 C4 C7 121.1(3) . . ? C5 C4 C7 122.2(3) . . ? C4 C5 C6 124.1(3) . . ? C4 C5 S2 121.6(2) . . ? C6 C5 S2 114.3(2) . . ? N1 C6 C5 121.0(3) . . ? N1 C6 C1 118.6(3) . . ? C5 C6 C1 120.3(3) . . ? C12 C7 C8 119.2(3) . . ? C12 C7 C4 121.0(4) . . ? C8 C7 C4 119.8(4) . . ? C7 C8 C9 120.5(4) . . ? C10 C9 C8 119.4(4) . . ? C11 C10 C9 120.4(4) . . ? C10 C11 C12 120.5(4) . . ? C7 C12 C11 120.0(4) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.402 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.082