# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_Fe(Cp*)2(1) _audit_creation_date 2011-11-24T17:36:38-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 Fe1 H30, C10 H10 N2 S6' _chemical_formula_sum 'C30 H40 Fe1 N2 S6' _chemical_formula_weight 676.84 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3382(12) _cell_length_b 9.6932(12) _cell_length_c 10.4978(14) _cell_angle_alpha 76.994(6) _cell_angle_beta 64.923(6) _cell_angle_gamma 70.853(6) _cell_volume 808.93(18) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4115 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 27.44 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.877 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.863 _exptl_absorpt_correction_T_max 0.957 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_unetI/netI 0.0451 _diffrn_reflns_number 12794 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _reflns_number_total 3662 _reflns_number_gt 2971 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0366P)^2^+0.5857P] 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_number_reflns 3662 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.0983 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.01 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.568 _refine_diff_density_min -0.461 _refine_diff_density_rms 0.073 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Fe1 Fe 0.5 0 0.5 0.01988(13) Uani 1 2 d S . . C1 C 0.6996(3) -0.1229(2) 0.3432(3) 0.0295(6) Uani 1 1 d . . . C2 C 0.7557(3) -0.0624(3) 0.4204(4) 0.0393(7) Uani 1 1 d . . . C3 C 0.6933(3) -0.1183(3) 0.5651(3) 0.0368(7) Uani 1 1 d . . . C4 C 0.5987(3) -0.2129(2) 0.5781(3) 0.0272(5) Uani 1 1 d . . . C5 C 0.6015(3) -0.2156(2) 0.4420(2) 0.0221(5) Uani 1 1 d . . . C6 C 0.7420(4) -0.0979(3) 0.1870(3) 0.0618(11) Uani 1 1 d . . . H6A H 0.8477 -0.1657 0.1395 0.093 Uiso 1 1 calc R . . H6B H 0.7489 0.0034 0.1534 0.093 Uiso 1 1 calc R . . H6C H 0.6569 -0.1151 0.1659 0.093 Uiso 1 1 calc R . . C7 C 0.8649(4) 0.0403(3) 0.3580(5) 0.0792(15) Uani 1 1 d . . . H7A H 0.8429 0.1023 0.4296 0.119 Uiso 1 1 calc R . . H7B H 0.8429 0.1023 0.2772 0.119 Uiso 1 1 calc R . . H7C H 0.9799 -0.0169 0.3265 0.119 Uiso 1 1 calc R . . C8 C 0.7217(5) -0.0873(4) 0.6856(5) 0.0750(13) Uani 1 1 d . . . H8A H 0.6232 -0.0861 0.7721 0.113 Uiso 1 1 calc R . . H8B H 0.7459 0.0084 0.6635 0.113 Uiso 1 1 calc R . . H8C H 0.8145 -0.1639 0.6995 0.113 Uiso 1 1 calc R . . C9 C 0.5129(4) -0.3012(3) 0.7106(3) 0.0493(8) Uani 1 1 d . . . H9A H 0.5884 -0.3969 0.7209 0.074 Uiso 1 1 calc R . . H9B H 0.4172 -0.3155 0.704 0.074 Uiso 1 1 calc R . . H9C H 0.4773 -0.2485 0.7928 0.074 Uiso 1 1 calc R . . C10 C 0.5201(3) -0.3037(3) 0.4075(3) 0.0411(7) Uani 1 1 d . . . H10A H 0.49 -0.2525 0.327 0.062 Uiso 1 1 calc R . . H10B H 0.4212 -0.316 0.4895 0.062 Uiso 1 1 calc R . . H10C H 0.5957 -0.4003 0.3834 0.062 Uiso 1 1 calc R . . C11 C 0.7208(3) 0.5350(3) 1.0187(3) 0.0320(6) Uani 1 1 d . . . H11A H 0.7426 0.6265 0.962 0.048 Uiso 1 1 calc R . . H11B H 0.7076 0.5381 1.1158 0.048 Uiso 1 1 calc R . . H11C H 0.6202 0.5235 1.0191 0.048 Uiso 1 1 calc R . . C12 C 0.8632(3) 0.4063(3) 0.9555(2) 0.0258(5) Uani 1 1 d . . . H12A H 0.9646 0.4174 0.956 0.031 Uiso 1 1 calc R . . H12B H 0.8422 0.3141 1.0139 0.031 Uiso 1 1 calc R . . N13 N 0.8860(2) 0.39777(19) 0.80993(19) 0.0208(4) Uani 1 1 d . . . C14 C 0.8142(3) 0.3139(2) 0.7808(2) 0.0225(5) Uani 1 1 d . . . S15 S 0.85159(7) 0.33855(6) 0.60064(6) 0.02148(14) Uani 1 1 d . . . C16 C 0.9647(3) 0.4645(2) 0.5675(2) 0.0194(4) Uani 1 1 d . . . C17 C 0.9734(3) 0.4828(2) 0.6941(2) 0.0198(4) Uani 1 1 d . . . S18 S 0.70426(8) 0.20111(7) 0.89324(6) 0.03175(16) Uani 1 1 d . . . S19 S 1.07255(7) 0.59051(6) 0.71003(6) 0.02543(15) 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 Fe1 0.0164(2) 0.0144(2) 0.0296(3) -0.00578(18) -0.0099(2) -0.00109(16) C1 0.0236(12) 0.0181(11) 0.0310(13) -0.0017(10) -0.0027(10) 0.0036(9) C2 0.0137(11) 0.0165(11) 0.083(2) -0.0126(13) -0.0142(13) 0.0016(9) C3 0.0301(14) 0.0281(13) 0.0595(19) -0.0208(13) -0.0290(14) 0.0102(11) C4 0.0252(12) 0.0198(11) 0.0288(13) -0.0061(10) -0.0103(10) 0.0064(9) C5 0.0187(11) 0.0140(10) 0.0310(13) -0.0074(9) -0.0087(10) 0.0014(8) C6 0.062(2) 0.0467(18) 0.0299(16) 0.0029(14) 0.0002(15) 0.0159(16) C7 0.0212(15) 0.0292(15) 0.166(4) -0.013(2) -0.013(2) -0.0083(12) C8 0.072(2) 0.063(2) 0.124(3) -0.054(2) -0.080(3) 0.0276(18) C9 0.0499(18) 0.0364(15) 0.0326(16) 0.0022(12) -0.0062(14) 0.0084(13) C10 0.0363(15) 0.0265(13) 0.069(2) -0.0199(13) -0.0256(15) -0.0018(11) C11 0.0344(14) 0.0354(13) 0.0231(13) -0.0088(11) -0.0095(11) -0.0031(11) C12 0.0315(13) 0.0288(12) 0.0196(12) -0.0025(9) -0.0125(10) -0.0071(10) N13 0.0231(10) 0.0212(9) 0.0188(10) -0.0043(8) -0.0090(8) -0.0038(8) C14 0.0234(12) 0.0211(11) 0.0223(12) -0.0058(9) -0.0089(10) -0.0022(9) S15 0.0237(3) 0.0233(3) 0.0206(3) -0.0043(2) -0.0086(2) -0.0084(2) C16 0.0177(11) 0.0183(10) 0.0233(12) -0.0042(9) -0.0094(9) -0.0026(8) C17 0.0192(11) 0.0190(10) 0.0215(11) -0.0040(9) -0.0093(9) -0.0019(8) S18 0.0415(4) 0.0312(3) 0.0238(3) -0.0012(3) -0.0079(3) -0.0184(3) S19 0.0292(3) 0.0300(3) 0.0244(3) -0.0043(2) -0.0136(3) -0.0113(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Fe1 C2 2.087(2) . ? Fe1 C2 2.087(2) 2_656 ? Fe1 C3 2.092(2) . ? Fe1 C3 2.092(2) 2_656 ? Fe1 C4 2.100(2) 2_656 ? Fe1 C4 2.100(2) . ? Fe1 C5 2.102(2) 2_656 ? Fe1 C5 2.102(2) . ? Fe1 C1 2.104(2) . ? Fe1 C1 2.104(2) 2_656 ? C1 C5 1.427(3) . ? C1 C2 1.432(4) . ? C1 C6 1.496(4) . ? C2 C3 1.424(4) . ? C2 C7 1.505(4) . ? C3 C4 1.419(4) . ? C3 C8 1.506(4) . ? C4 C5 1.424(3) . ? C4 C9 1.509(4) . ? C5 C10 1.496(3) . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 C12 1.517(3) . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C11 H11C 0.98 . ? C12 N13 1.468(3) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? N13 C14 1.359(3) . ? N13 C17 1.405(3) . ? C14 S18 1.665(2) . ? C14 S15 1.746(2) . ? S15 C16 1.752(2) . ? C16 C16 1.409(4) 2_766 ? C16 C17 1.419(3) . ? C17 S19 1.679(2) . ? 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 C2 Fe1 C2 180 . 2_656 ? C2 Fe1 C3 39.84(12) . . ? C2 Fe1 C3 140.16(12) 2_656 . ? C2 Fe1 C3 140.16(12) . 2_656 ? C2 Fe1 C3 39.84(12) 2_656 2_656 ? C3 Fe1 C3 179.9990(10) . 2_656 ? C2 Fe1 C4 113.45(10) . 2_656 ? C2 Fe1 C4 66.55(10) 2_656 2_656 ? C3 Fe1 C4 140.44(10) . 2_656 ? C3 Fe1 C4 39.56(10) 2_656 2_656 ? C2 Fe1 C4 66.55(10) . . ? C2 Fe1 C4 113.45(10) 2_656 . ? C3 Fe1 C4 39.56(10) . . ? C3 Fe1 C4 140.44(10) 2_656 . ? C4 Fe1 C4 180 2_656 . ? C2 Fe1 C5 113.30(9) . 2_656 ? C2 Fe1 C5 66.70(9) 2_656 2_656 ? C3 Fe1 C5 113.34(9) . 2_656 ? C3 Fe1 C5 66.66(9) 2_656 2_656 ? C4 Fe1 C5 39.60(9) 2_656 2_656 ? C4 Fe1 C5 140.40(9) . 2_656 ? C2 Fe1 C5 66.70(9) . . ? C2 Fe1 C5 113.30(9) 2_656 . ? C3 Fe1 C5 66.65(9) . . ? C3 Fe1 C5 113.34(9) 2_656 . ? C4 Fe1 C5 140.40(9) 2_656 . ? C4 Fe1 C5 39.60(9) . . ? C5 Fe1 C5 180 2_656 . ? C2 Fe1 C1 39.96(11) . . ? C2 Fe1 C1 140.04(11) 2_656 . ? C3 Fe1 C1 66.98(10) . . ? C3 Fe1 C1 113.02(10) 2_656 . ? C4 Fe1 C1 113.38(9) 2_656 . ? C4 Fe1 C1 66.62(9) . . ? C5 Fe1 C1 140.33(9) 2_656 . ? C5 Fe1 C1 39.67(9) . . ? C2 Fe1 C1 140.04(11) . 2_656 ? C2 Fe1 C1 39.96(11) 2_656 2_656 ? C3 Fe1 C1 113.02(10) . 2_656 ? C3 Fe1 C1 66.98(10) 2_656 2_656 ? C4 Fe1 C1 66.62(9) 2_656 2_656 ? C4 Fe1 C1 113.38(9) . 2_656 ? C5 Fe1 C1 39.67(9) 2_656 2_656 ? C5 Fe1 C1 140.33(9) . 2_656 ? C1 Fe1 C1 180 . 2_656 ? C5 C1 C2 107.3(2) . . ? C5 C1 C6 126.6(3) . . ? C2 C1 C6 126.1(3) . . ? C5 C1 Fe1 70.11(13) . . ? C2 C1 Fe1 69.37(14) . . ? C6 C1 Fe1 127.58(18) . . ? C3 C2 C1 108.3(2) . . ? C3 C2 C7 126.1(3) . . ? C1 C2 C7 125.6(3) . . ? C3 C2 Fe1 70.28(14) . . ? C1 C2 Fe1 70.67(13) . . ? C7 C2 Fe1 125.75(17) . . ? C4 C3 C2 107.9(2) . . ? C4 C3 C8 124.6(3) . . ? C2 C3 C8 127.5(3) . . ? C4 C3 Fe1 70.55(13) . . ? C2 C3 Fe1 69.89(14) . . ? C8 C3 Fe1 125.75(18) . . ? C3 C4 C5 108.3(2) . . ? C3 C4 C9 127.1(3) . . ? C5 C4 C9 124.5(2) . . ? C3 C4 Fe1 69.89(14) . . ? C5 C4 Fe1 70.28(12) . . ? C9 C4 Fe1 127.12(17) . . ? C4 C5 C1 108.2(2) . . ? C4 C5 C10 126.0(2) . . ? C1 C5 C10 125.8(2) . . ? C4 C5 Fe1 70.12(12) . . ? C1 C5 Fe1 70.22(12) . . ? C10 C5 Fe1 126.66(16) . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N13 C12 C11 110.98(18) . . ? N13 C12 H12A 109.4 . . ? C11 C12 H12A 109.4 . . ? N13 C12 H12B 109.4 . . ? C11 C12 H12B 109.4 . . ? H12A C12 H12B 108 . . ? C14 N13 C17 116.10(18) . . ? C14 N13 C12 121.56(19) . . ? C17 N13 C12 122.20(18) . . ? N13 C14 S18 127.84(18) . . ? N13 C14 S15 110.38(16) . . ? S18 C14 S15 121.78(13) . . ? C14 S15 C16 91.94(10) . . ? C16 C16 C17 126.2(2) 2_766 . ? C16 C16 S15 123.3(2) 2_766 . ? C17 C16 S15 110.47(16) . . ? N13 C17 C16 111.09(18) . . ? N13 C17 S19 122.57(16) . . ? C16 C17 S19 126.33(17) . . ? 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 C2 Fe1 C1 C5 118.3(2) . . . . ? C2 Fe1 C1 C5 -61.7(2) 2_656 . . . ? C3 Fe1 C1 C5 80.67(15) . . . . ? C3 Fe1 C1 C5 -99.33(15) 2_656 . . . ? C4 Fe1 C1 C5 -142.53(14) 2_656 . . . ? C4 Fe1 C1 C5 37.47(14) . . . . ? C5 Fe1 C1 C5 180 2_656 . . . ? C1 Fe1 C1 C5 -111(6) 2_656 . . . ? C2 Fe1 C1 C2 180 2_656 . . . ? C3 Fe1 C1 C2 -37.64(15) . . . . ? C3 Fe1 C1 C2 142.36(15) 2_656 . . . ? C4 Fe1 C1 C2 99.16(16) 2_656 . . . ? C4 Fe1 C1 C2 -80.84(16) . . . . ? C5 Fe1 C1 C2 61.7(2) 2_656 . . . ? C5 Fe1 C1 C2 -118.3(2) . . . . ? C1 Fe1 C1 C2 130(6) 2_656 . . . ? C2 Fe1 C1 C6 -120.3(3) . . . . ? C2 Fe1 C1 C6 59.7(3) 2_656 . . . ? C3 Fe1 C1 C6 -157.9(3) . . . . ? C3 Fe1 C1 C6 22.1(3) 2_656 . . . ? C4 Fe1 C1 C6 -21.2(3) 2_656 . . . ? C4 Fe1 C1 C6 158.8(3) . . . . ? C5 Fe1 C1 C6 -58.6(3) 2_656 . . . ? C5 Fe1 C1 C6 121.4(3) . . . . ? C1 Fe1 C1 C6 10(6) 2_656 . . . ? C5 C1 C2 C3 0.3(3) . . . . ? C6 C1 C2 C3 -177.4(2) . . . . ? Fe1 C1 C2 C3 60.46(16) . . . . ? C5 C1 C2 C7 179.2(2) . . . . ? C6 C1 C2 C7 1.5(4) . . . . ? Fe1 C1 C2 C7 -120.7(2) . . . . ? C5 C1 C2 Fe1 -60.13(15) . . . . ? C6 C1 C2 Fe1 122.1(2) . . . . ? C2 Fe1 C2 C3 59(8) 2_656 . . . ? C3 Fe1 C2 C3 180 2_656 . . . ? C4 Fe1 C2 C3 142.36(14) 2_656 . . . ? C4 Fe1 C2 C3 -37.64(14) . . . . ? C5 Fe1 C2 C3 99.05(15) 2_656 . . . ? C5 Fe1 C2 C3 -80.95(15) . . . . ? C1 Fe1 C2 C3 -118.68(19) . . . . ? C1 Fe1 C2 C3 61.32(19) 2_656 . . . ? C2 Fe1 C2 C1 18E1(10) 2_656 . . . ? C3 Fe1 C2 C1 118.68(19) . . . . ? C3 Fe1 C2 C1 -61.32(19) 2_656 . . . ? C4 Fe1 C2 C1 -98.96(14) 2_656 . . . ? C4 Fe1 C2 C1 81.04(14) . . . . ? C5 Fe1 C2 C1 -142.27(13) 2_656 . . . ? C5 Fe1 C2 C1 37.73(13) . . . . ? C1 Fe1 C2 C1 180 2_656 . . . ? C2 Fe1 C2 C7 -62(8) 2_656 . . . ? C3 Fe1 C2 C7 -120.9(4) . . . . ? C3 Fe1 C2 C7 59.1(4) 2_656 . . . ? C4 Fe1 C2 C7 21.5(4) 2_656 . . . ? C4 Fe1 C2 C7 -158.5(4) . . . . ? C5 Fe1 C2 C7 -21.8(4) 2_656 . . . ? C5 Fe1 C2 C7 158.2(4) . . . . ? C1 Fe1 C2 C7 120.5(4) . . . . ? C1 Fe1 C2 C7 -59.5(4) 2_656 . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C7 C2 C3 C4 -178.9(2) . . . . ? Fe1 C2 C3 C4 60.62(16) . . . . ? C1 C2 C3 C8 179.1(2) . . . . ? C7 C2 C3 C8 0.2(4) . . . . ? Fe1 C2 C3 C8 -120.2(3) . . . . ? C1 C2 C3 Fe1 -60.71(16) . . . . ? C7 C2 C3 Fe1 120.4(2) . . . . ? C2 Fe1 C3 C4 -118.4(2) . . . . ? C2 Fe1 C3 C4 61.6(2) 2_656 . . . ? C3 Fe1 C3 C4 -8E1(3) 2_656 . . . ? C4 Fe1 C3 C4 180 2_656 . . . ? C5 Fe1 C3 C4 142.67(14) 2_656 . . . ? C5 Fe1 C3 C4 -37.33(14) . . . . ? C1 Fe1 C3 C4 -80.64(16) . . . . ? C1 Fe1 C3 C4 99.36(16) 2_656 . . . ? C2 Fe1 C3 C2 180 2_656 . . . ? C3 Fe1 C3 C2 4E1(3) 2_656 . . . ? C4 Fe1 C3 C2 -61.6(2) 2_656 . . . ? C4 Fe1 C3 C2 118.4(2) . . . . ? C5 Fe1 C3 C2 -98.93(15) 2_656 . . . ? C5 Fe1 C3 C2 81.07(15) . . . . ? C1 Fe1 C3 C2 37.75(14) . . . . ? C1 Fe1 C3 C2 -142.25(14) 2_656 . . . ? C2 Fe1 C3 C8 122.4(4) . . . . ? C2 Fe1 C3 C8 -57.6(4) 2_656 . . . ? C3 Fe1 C3 C8 16E1(3) 2_656 . . . ? C4 Fe1 C3 C8 60.8(4) 2_656 . . . ? C4 Fe1 C3 C8 -119.2(4) . . . . ? C5 Fe1 C3 C8 23.4(3) 2_656 . . . ? C5 Fe1 C3 C8 -156.6(3) . . . . ? C1 Fe1 C3 C8 160.1(3) . . . . ? C1 Fe1 C3 C8 -19.9(3) 2_656 . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C8 C3 C4 C5 -179.4(2) . . . . ? Fe1 C3 C4 C5 60.01(15) . . . . ? C2 C3 C4 C9 177.9(2) . . . . ? C8 C3 C4 C9 -1.3(4) . . . . ? Fe1 C3 C4 C9 -121.9(2) . . . . ? C2 C3 C4 Fe1 -60.20(16) . . . . ? C8 C3 C4 Fe1 120.6(2) . . . . ? C2 Fe1 C4 C3 37.90(16) . . . . ? C2 Fe1 C4 C3 -142.10(16) 2_656 . . . ? C3 Fe1 C4 C3 180 2_656 . . . ? C4 Fe1 C4 C3 -27(8) 2_656 . . . ? C5 Fe1 C4 C3 -60.8(2) 2_656 . . . ? C5 Fe1 C4 C3 119.1(2) . . . . ? C1 Fe1 C4 C3 81.62(17) . . . . ? C1 Fe1 C4 C3 -98.38(17) 2_656 . . . ? C2 Fe1 C4 C5 -81.25(15) . . . . ? C2 Fe1 C4 C5 98.75(15) 2_656 . . . ? C3 Fe1 C4 C5 -119.1(2) . . . . ? C3 Fe1 C4 C5 60.8(2) 2_656 . . . ? C4 Fe1 C4 C5 -146(8) 2_656 . . . ? C5 Fe1 C4 C5 180 2_656 . . . ? C1 Fe1 C4 C5 -37.53(14) . . . . ? C1 Fe1 C4 C5 142.47(14) 2_656 . . . ? C2 Fe1 C4 C9 159.8(3) . . . . ? C2 Fe1 C4 C9 -20.2(3) 2_656 . . . ? C3 Fe1 C4 C9 121.9(3) . . . . ? C3 Fe1 C4 C9 -58.1(3) 2_656 . . . ? C4 Fe1 C4 C9 95(8) 2_656 . . . ? C5 Fe1 C4 C9 61.1(3) 2_656 . . . ? C5 Fe1 C4 C9 -118.9(3) . . . . ? C1 Fe1 C4 C9 -156.5(3) . . . . ? C1 Fe1 C4 C9 23.5(3) 2_656 . . . ? C3 C4 C5 C1 0.4(2) . . . . ? C9 C4 C5 C1 -177.7(2) . . . . ? Fe1 C4 C5 C1 60.18(15) . . . . ? C3 C4 C5 C10 178.8(2) . . . . ? C9 C4 C5 C10 0.6(4) . . . . ? Fe1 C4 C5 C10 -121.5(2) . . . . ? C3 C4 C5 Fe1 -59.77(16) . . . . ? C9 C4 C5 Fe1 122.1(2) . . . . ? C2 C1 C5 C4 -0.5(2) . . . . ? C6 C1 C5 C4 177.3(2) . . . . ? Fe1 C1 C5 C4 -60.11(15) . . . . ? C2 C1 C5 C10 -178.8(2) . . . . ? C6 C1 C5 C10 -1.1(4) . . . . ? Fe1 C1 C5 C10 121.5(2) . . . . ? C2 C1 C5 Fe1 59.66(15) . . . . ? C6 C1 C5 Fe1 -122.6(2) . . . . ? C2 Fe1 C5 C4 80.84(16) . . . . ? C2 Fe1 C5 C4 -99.16(16) 2_656 . . . ? C3 Fe1 C5 C4 37.29(15) . . . . ? C3 Fe1 C5 C4 -142.71(15) 2_656 . . . ? C4 Fe1 C5 C4 180 2_656 . . . ? C5 Fe1 C5 C4 21(9) 2_656 . . . ? C1 Fe1 C5 C4 118.8(2) . . . . ? C1 Fe1 C5 C4 -61.2(2) 2_656 . . . ? C2 Fe1 C5 C1 -38.00(16) . . . . ? C2 Fe1 C5 C1 142.00(16) 2_656 . . . ? C3 Fe1 C5 C1 -81.56(16) . . . . ? C3 Fe1 C5 C1 98.44(16) 2_656 . . . ? C4 Fe1 C5 C1 61.2(2) 2_656 . . . ? C4 Fe1 C5 C1 -118.8(2) . . . . ? C5 Fe1 C5 C1 -98(9) 2_656 . . . ? C1 Fe1 C5 C1 180 2_656 . . . ? C2 Fe1 C5 C10 -158.5(3) . . . . ? C2 Fe1 C5 C10 21.5(3) 2_656 . . . ? C3 Fe1 C5 C10 158.0(3) . . . . ? C3 Fe1 C5 C10 -22.0(3) 2_656 . . . ? C4 Fe1 C5 C10 -59.3(3) 2_656 . . . ? C4 Fe1 C5 C10 120.7(3) . . . . ? C5 Fe1 C5 C10 142(9) 2_656 . . . ? C1 Fe1 C5 C10 -120.5(3) . . . . ? C1 Fe1 C5 C10 59.5(3) 2_656 . . . ? C11 C12 N13 C14 -92.9(2) . . . . ? C11 C12 N13 C17 82.7(3) . . . . ? C17 N13 C14 S18 179.56(16) . . . . ? C12 N13 C14 S18 -4.6(3) . . . . ? C17 N13 C14 S15 -0.5(2) . . . . ? C12 N13 C14 S15 175.30(15) . . . . ? N13 C14 S15 C16 -0.23(17) . . . . ? S18 C14 S15 C16 179.68(15) . . . . ? C14 S15 C16 C16 -179.0(2) . . . 2_766 ? C14 S15 C16 C17 0.91(17) . . . . ? C14 N13 C17 C16 1.2(3) . . . . ? C12 N13 C17 C16 -174.57(18) . . . . ? C14 N13 C17 S19 -178.86(16) . . . . ? C12 N13 C17 S19 5.3(3) . . . . ? C16 C16 C17 N13 178.6(2) 2_766 . . . ? S15 C16 C17 N13 -1.3(2) . . . . ? C16 C16 C17 S19 -1.3(4) 2_766 . . . ? S15 C16 C17 S19 178.77(13) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 951710' ####################################################################### # # 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_compound1 _audit_creation_date 2011-11-08T11:27:46-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C10 H10 N2 S6)' _chemical_formula_sum 'C20 H20 N4 S12' _chemical_formula_weight 701.12 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4387(5) _cell_length_b 8.1655(7) _cell_length_c 12.5242(9) _cell_angle_alpha 108.826(4) _cell_angle_beta 101.941(4) _cell_angle_gamma 91.319(4) _cell_volume 701.13(9) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2684 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 27.1 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description stick _exptl_crystal_colour black _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.661 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.956 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.856 _exptl_absorpt_correction_T_max 0.962 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_av_unetI/netI 0.0468 _diffrn_reflns_number 8754 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 27.41 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 3185 _reflns_number_gt 2678 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0307P)^2^+0.0759P] 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_number_reflns 3185 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.075 _refine_ls_wR_factor_gt 0.0716 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.379 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.073 _iucr_refine_instructions_details ; .res file for SHELXL : job.res ................................................................. TITL import in P -1 CELL 0.71073 7.4387 8.1655 12.5242 108.826 101.941 91.319 ZERR 1.00 0.0005 0.0007 0.0009 0.004 0.004 0.004 LATT 1 SFAC C H N S UNIT 20 20 4 12 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.030700 0.075900 FVAR 0.76798 MOLE 1 S1 4 0.479582 -0.094587 0.144992 11.00000 0.01902 0.01539 = 0.01364 0.00570 0.00401 -0.00030 S2 4 0.636318 0.365191 0.083500 11.00000 0.03018 0.01577 = 0.01823 0.00551 0.00303 -0.00535 S3 4 0.566903 0.067579 0.400564 11.00000 0.03402 0.02883 = 0.01384 0.00833 0.00705 0.00127 C1 1 0.516135 0.029626 0.059287 11.00000 0.01242 0.01402 = 0.01551 0.00553 0.00294 -0.00029 C2 1 0.586543 0.208485 0.131936 11.00000 0.01239 0.01657 = 0.01605 0.00396 0.00287 0.00105 N3 3 0.607286 0.229146 0.248260 11.00000 0.01617 0.01474 = 0.01193 0.00150 0.00154 -0.00034 C4 1 0.557881 0.084618 0.272568 11.00000 0.01470 0.01860 = 0.01462 0.00347 0.00368 0.00244 C5 1 0.668724 0.399058 0.339845 11.00000 0.02035 0.01908 = 0.01570 0.00006 -0.00092 -0.00292 AFIX 23 H5A 2 0.766456 0.460149 0.319796 11.00000 -1.20000 H5B 2 0.721646 0.380941 0.414028 11.00000 -1.20000 AFIX 0 C6 1 0.508030 0.510734 0.353950 11.00000 0.02933 0.02297 = 0.02240 -0.00319 0.00185 0.00508 AFIX 137 H6A 2 0.456400 0.529595 0.280724 11.00000 -1.50000 H6B 2 0.551998 0.623023 0.414787 11.00000 -1.50000 H6C 2 0.412418 0.451357 0.375403 11.00000 -1.50000 AFIX 0 MOLE 2 S11 4 1.086983 0.195805 0.176320 11.00000 0.01797 0.01408 = 0.01592 0.00287 0.00217 -0.00147 S12 4 0.863703 -0.330153 0.008199 11.00000 0.02500 0.01444 = 0.01967 0.00455 0.00456 -0.00266 S13 4 1.093644 0.192159 0.413456 11.00000 0.02749 0.02788 = 0.01440 0.00196 0.00236 -0.00185 C11 1 1.005076 0.007431 0.057003 11.00000 0.01140 0.01219 = 0.01721 0.00285 0.00076 0.00045 C12 1 0.948438 -0.133589 0.094466 11.00000 0.01251 0.01691 = 0.01783 0.00538 0.00489 0.00245 N13 3 0.974536 -0.078823 0.214438 11.00000 0.01757 0.01568 = 0.01439 0.00542 0.00268 0.00011 C14 1 1.047017 0.090400 0.272900 11.00000 0.01302 0.02106 = 0.01735 0.00564 0.00332 0.00165 C15 1 0.937681 -0.198137 0.276469 11.00000 0.02241 0.01955 = 0.01951 0.00960 0.00501 -0.00029 AFIX 23 H15A 2 0.827863 -0.280145 0.230185 11.00000 -1.20000 H15B 2 0.910674 -0.130230 0.351613 11.00000 -1.20000 AFIX 0 C16 1 1.101760 -0.299479 0.297403 11.00000 0.02744 0.02425 = 0.02346 0.01027 -0.00025 0.00278 AFIX 137 H16A 2 1.122600 -0.373651 0.222929 11.00000 -1.50000 H16B 2 1.076993 -0.371996 0.342647 11.00000 -1.50000 H16C 2 1.211777 -0.218315 0.340168 11.00000 -1.50000 HKLF 4 REM import in P -1 REM R1 = 0.0332 for 2678 Fo > 4sig(Fo) and 0.0417 for all 3185 data REM 165 parameters refined using 0 restraints END WGHT 0.0302 0.0613 REM Highest difference peak 0.38, deepest hole -0.33, 1-sigma level 0.07 Q1 1 0.8778 -0.2202 0.0540 11.00000 0.05 0.38 Q2 1 1.0333 0.0981 0.1040 11.00000 0.05 0.38 Q3 1 0.5250 0.0191 0.2168 11.00000 0.05 0.36 Q4 1 0.5379 0.1190 0.0812 11.00000 0.05 0.34 Q5 1 0.9502 -0.1127 0.1426 11.00000 0.05 0.32 Q6 1 1.0280 0.0008 0.2352 11.00000 0.05 0.32 Q7 1 0.9774 -0.0522 0.0713 11.00000 0.05 0.32 Q8 1 1.0714 0.1409 0.2317 11.00000 0.05 0.29 Q9 1 1.0435 0.0018 0.0252 11.00000 0.05 0.28 Q10 1 0.5000 0.0000 0.0000 10.50000 0.05 0.28 Q11 1 1.0214 0.1209 0.3392 11.00000 0.05 0.28 Q12 1 0.5187 -0.0388 0.0974 11.00000 0.05 0.27 Q13 1 0.6137 0.3057 0.2804 11.00000 0.05 0.27 Q14 1 0.8635 -0.2327 0.2564 11.00000 0.05 0.26 Q15 1 0.9507 -0.1381 0.2400 11.00000 0.05 0.26 Q16 1 0.6049 0.2729 0.1030 11.00000 0.05 0.25 Q17 1 0.7988 -0.2994 -0.0670 11.00000 0.05 0.25 Q18 1 1.1944 -0.4608 0.3995 11.00000 0.05 0.25 Q19 1 0.6385 0.1228 0.2248 11.00000 0.05 0.24 Q20 1 0.8165 -0.4370 -0.0670 11.00000 0.05 0.24 ; #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.47958(6) -0.09459(7) 0.14499(4) 0.01579(12) Uani 1 1 d . . . S2 S 0.63632(7) 0.36519(7) 0.08350(4) 0.02194(13) Uani 1 1 d . . . S3 S 0.56690(7) 0.06758(8) 0.40056(4) 0.02505(14) Uani 1 1 d . . . C1 C 0.5161(2) 0.0296(3) 0.05929(15) 0.0139(4) Uani 1 1 d . . . C2 C 0.5865(2) 0.2085(3) 0.13194(16) 0.0154(4) Uani 1 1 d . . . N3 N 0.6073(2) 0.2291(2) 0.24826(13) 0.0153(4) Uani 1 1 d . . . C4 C 0.5579(2) 0.0846(3) 0.27257(16) 0.0164(4) Uani 1 1 d . . . C5 C 0.6687(3) 0.3991(3) 0.33984(17) 0.0207(5) Uani 1 1 d . . . H5A H 0.7665 0.4601 0.3198 0.025 Uiso 1 1 calc R . . H5B H 0.7216 0.3809 0.414 0.025 Uiso 1 1 calc R . . C6 C 0.5080(3) 0.5107(3) 0.35395(19) 0.0281(5) Uani 1 1 d . . . H6A H 0.4564 0.5296 0.2807 0.042 Uiso 1 1 calc R . . H6B H 0.552 0.623 0.4148 0.042 Uiso 1 1 calc R . . H6C H 0.4124 0.4514 0.3754 0.042 Uiso 1 1 calc R . . S11 S 1.08698(6) 0.19580(7) 0.17632(4) 0.01683(12) Uani 1 1 d . . . S12 S 0.86370(7) -0.33015(7) 0.00820(4) 0.02015(13) Uani 1 1 d . . . S13 S 1.09364(7) 0.19216(8) 0.41346(4) 0.02496(14) Uani 1 1 d . . . C11 C 1.0051(2) 0.0074(3) 0.05700(15) 0.0145(4) Uani 1 1 d . . . C12 C 0.9484(2) -0.1336(3) 0.09447(16) 0.0156(4) Uani 1 1 d . . . N13 N 0.9745(2) -0.0788(2) 0.21444(13) 0.0160(4) Uani 1 1 d . . . C14 C 1.0470(2) 0.0904(3) 0.27290(17) 0.0174(4) Uani 1 1 d . . . C15 C 0.9377(3) -0.1981(3) 0.27647(17) 0.0197(4) Uani 1 1 d . . . H15A H 0.8279 -0.2801 0.2302 0.024 Uiso 1 1 calc R . . H15B H 0.9107 -0.1302 0.3516 0.024 Uiso 1 1 calc R . . C16 C 1.1018(3) -0.2995(3) 0.29740(18) 0.0254(5) Uani 1 1 d . . . H16A H 1.1226 -0.3737 0.2229 0.038 Uiso 1 1 calc R . . H16B H 1.077 -0.372 0.3426 0.038 Uiso 1 1 calc R . . H16C H 1.2118 -0.2183 0.3402 0.038 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 0.0190(2) 0.0154(3) 0.0136(2) 0.0057(2) 0.00401(18) -0.0003(2) S2 0.0302(3) 0.0158(3) 0.0182(3) 0.0055(2) 0.0030(2) -0.0054(2) S3 0.0340(3) 0.0288(4) 0.0138(3) 0.0083(2) 0.0071(2) 0.0013(2) C1 0.0124(9) 0.0140(11) 0.0155(10) 0.0055(9) 0.0029(7) -0.0003(8) C2 0.0124(9) 0.0166(11) 0.0161(10) 0.0040(9) 0.0029(7) 0.0010(8) N3 0.0162(8) 0.0147(9) 0.0119(8) 0.0015(7) 0.0015(6) -0.0003(7) C4 0.0147(9) 0.0186(11) 0.0146(10) 0.0035(9) 0.0037(7) 0.0024(8) C5 0.0203(10) 0.0191(12) 0.0157(10) 0.0001(9) -0.0009(8) -0.0029(9) C6 0.0293(11) 0.0230(13) 0.0224(11) -0.0032(10) 0.0018(9) 0.0051(10) S11 0.0180(2) 0.0141(3) 0.0159(3) 0.0029(2) 0.00217(19) -0.00147(19) S12 0.0250(3) 0.0144(3) 0.0197(3) 0.0045(2) 0.0046(2) -0.0027(2) S13 0.0275(3) 0.0279(3) 0.0144(3) 0.0020(2) 0.0024(2) -0.0019(2) C11 0.0114(9) 0.0122(11) 0.0172(10) 0.0029(9) 0.0008(7) 0.0004(7) C12 0.0125(9) 0.0169(11) 0.0178(10) 0.0054(9) 0.0049(7) 0.0024(8) N13 0.0176(8) 0.0157(10) 0.0144(8) 0.0054(7) 0.0027(6) 0.0001(7) C14 0.0130(9) 0.0211(12) 0.0174(10) 0.0056(9) 0.0033(7) 0.0016(8) C15 0.0224(10) 0.0195(12) 0.0195(10) 0.0096(9) 0.0050(8) -0.0003(9) C16 0.0274(11) 0.0242(13) 0.0235(12) 0.0103(10) -0.0002(9) 0.0028(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.7509(19) . ? S1 C4 1.761(2) . ? S2 C2 1.648(2) . ? S3 C4 1.641(2) . ? C1 C1 1.371(4) 2_655 ? C1 C2 1.465(3) . ? C2 N3 1.386(2) . ? N3 C4 1.371(3) . ? N3 C5 1.475(2) . ? C5 C6 1.525(3) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? S11 C11 1.7513(19) . ? S11 C14 1.761(2) . ? S12 C12 1.641(2) . ? S13 C14 1.643(2) . ? C11 C11 1.379(4) 2_755 ? C11 C12 1.460(3) . ? C12 N13 1.392(2) . ? N13 C14 1.373(3) . ? N13 C15 1.481(2) . ? C15 C16 1.516(3) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 H16A 0.98 . ? C16 H16B 0.98 . ? C16 H16C 0.98 . ? 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 C4 91.34(9) . . ? C1 C1 C2 123.9(2) 2_655 . ? C1 C1 S1 125.5(2) 2_655 . ? C2 C1 S1 110.52(13) . . ? N3 C2 C1 110.84(17) . . ? N3 C2 S2 124.01(15) . . ? C1 C2 S2 125.15(14) . . ? C4 N3 C2 115.99(16) . . ? C4 N3 C5 122.05(16) . . ? C2 N3 C5 121.87(17) . . ? N3 C4 S3 127.52(15) . . ? N3 C4 S1 111.30(14) . . ? S3 C4 S1 121.18(13) . . ? N3 C5 C6 110.84(15) . . ? N3 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? N3 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? 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 . . ? C11 S11 C14 91.47(9) . . ? C11 C11 C12 124.2(2) 2_755 . ? C11 C11 S11 125.2(2) 2_755 . ? C12 C11 S11 110.66(13) . . ? N13 C12 C11 110.77(17) . . ? N13 C12 S12 123.97(15) . . ? C11 C12 S12 125.26(15) . . ? C14 N13 C12 116.02(16) . . ? C14 N13 C15 121.61(16) . . ? C12 N13 C15 122.26(16) . . ? N13 C14 S13 127.47(15) . . ? N13 C14 S11 111.08(14) . . ? S13 C14 S11 121.45(13) . . ? N13 C15 C16 111.05(16) . . ? N13 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? N13 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 C4 S1 C1 C1 179.5(2) . . . 2_655 ? C4 S1 C1 C2 -0.65(14) . . . . ? C1 C1 C2 N3 -179.2(2) 2_655 . . . ? S1 C1 C2 N3 0.89(19) . . . . ? C1 C1 C2 S2 0.4(3) 2_655 . . . ? S1 C1 C2 S2 -179.47(11) . . . . ? C1 C2 N3 C4 -0.7(2) . . . . ? S2 C2 N3 C4 179.62(14) . . . . ? C1 C2 N3 C5 -177.36(15) . . . . ? S2 C2 N3 C5 3.0(2) . . . . ? C2 N3 C4 S3 179.83(14) . . . . ? C5 N3 C4 S3 -3.6(3) . . . . ? C2 N3 C4 S1 0.2(2) . . . . ? C5 N3 C4 S1 176.86(13) . . . . ? C1 S1 C4 N3 0.25(14) . . . . ? C1 S1 C4 S3 -179.36(12) . . . . ? C4 N3 C5 C6 -95.1(2) . . . . ? C2 N3 C5 C6 81.3(2) . . . . ? C14 S11 C11 C11 -180.0(2) . . . 2_755 ? C14 S11 C11 C12 -0.04(14) . . . . ? C11 C11 C12 N13 -179.8(2) 2_755 . . . ? S11 C11 C12 N13 0.27(19) . . . . ? C11 C11 C12 S12 -0.3(3) 2_755 . . . ? S11 C11 C12 S12 179.80(11) . . . . ? C11 C12 N13 C14 -0.4(2) . . . . ? S12 C12 N13 C14 -179.98(14) . . . . ? C11 C12 N13 C15 -176.75(15) . . . . ? S12 C12 N13 C15 3.7(2) . . . . ? C12 N13 C14 S13 -179.91(14) . . . . ? C15 N13 C14 S13 -3.6(3) . . . . ? C12 N13 C14 S11 0.4(2) . . . . ? C15 N13 C14 S11 176.75(13) . . . . ? C11 S11 C14 N13 -0.20(14) . . . . ? C11 S11 C14 S13 -179.90(13) . . . . ? C14 N13 C15 C16 -92.3(2) . . . . ? C12 N13 C15 C16 83.8(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 951711'