# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Gangopadhyay, Snigdha' _publ_contact_author_email snigdhagangopadhyay@yahoo.com _publ_section_title ; In situ formation of ligand 2,2'-[(E)-diazene-1,2-diyldicarbonothioyl]diphenol and structural characterization of its binuclear rhodium(V) complex containing RhO2+ ; loop_ _publ_author_name S.Gangopadhyay P.Basak M.Drew P.Gangopadhyay #===END # Attachment '- rh[1].cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 766983' #TrackingRef '- rh[1].cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 N O4 Rh S2' _chemical_formula_weight 363.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 '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' Rh Rh -1.1178 0.9187 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2911(6) _cell_length_b 8.9330(8) _cell_length_c 10.6189(9) _cell_angle_alpha 68.437(8) _cell_angle_beta 87.346(7) _cell_angle_gamma 71.086(8) _cell_volume 606.40(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4289 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 30.00 _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.989 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 1.752 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSPACK, Oxford Diffraction Ltd' _exptl_absorpt_correction_T_min 0.881 _exptl_absorpt_correction_T_max 1.000 _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_standards_number n/a _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 4289 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3378 _reflns_number_gt 2777 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _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 ; _refine_ls_weighting_details w=1/[\s^2^(Fo^2^)+(0.1067P)^2^+3.1967P] 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 3378 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0659 _refine_ls_wR_factor_ref 0.1909 _refine_ls_wR_factor_gt 0.1844 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 Rh1 Rh 0.80240(7) 0.91205(7) 0.71581(5) 0.02819(18) Uani 1 1 d . . . S32 S 1.1343(2) 1.0940(2) 0.74524(16) 0.0275(3) Uani 1 1 d . . . O11 O 1.0356(6) 0.7704(6) 0.8398(4) 0.0260(9) Uani 1 1 d . . . O31 O 0.9171(7) 1.1156(6) 0.7345(5) 0.0313(10) Uani 1 1 d . . . O1 O 0.7578(8) 0.7531(7) 0.6843(5) 0.0357(11) Uani 1 1 d . . . O2 O 0.6233(7) 0.9755(7) 0.8135(5) 0.0374(11) Uani 1 1 d . . . C12 C 1.1918(9) 0.6465(8) 0.8229(7) 0.0274(12) Uani 1 1 d . . . N19 N 1.0249(8) 0.9284(7) 0.5602(5) 0.0266(10) Uani 1 1 d . . . C13 C 1.2672(11) 0.4967(9) 0.9356(9) 0.0410(17) Uani 1 1 d . . . H13 H 1.2062 0.4804 1.0161 0.049 Uiso 1 1 calc R . . C16 C 1.4525(10) 0.5388(13) 0.6971(13) 0.056(3) Uani 1 1 d . . . H16 H 1.5168 0.5528 0.6181 0.067 Uiso 1 1 calc R . . C14 C 1.4355(13) 0.3709(10) 0.9267(14) 0.066(4) Uani 1 1 d . . . H14 H 1.4875 0.2717 1.0026 0.079 Uiso 1 1 calc R . . C15 C 1.5258(12) 0.3907(12) 0.8082(16) 0.070(4) Uani 1 1 d . . . H15 H 1.6357 0.3044 0.8032 0.084 Uiso 1 1 calc R . . C17 C 1.2799(8) 0.6726(9) 0.6989(7) 0.0291(13) Uani 1 1 d . . . C33 C 1.1443(19) 1.2991(14) 0.6404(9) 0.065(3) Uani 1 1 d . . . H33A H 1.0941 1.3281 0.5494 0.097 Uiso 1 1 calc R . . H33B H 1.2768 1.2972 0.6399 0.097 Uiso 1 1 calc R . . H33C H 1.0674 1.3826 0.6754 0.097 Uiso 1 1 calc R . . S18 S 1.3788(6) 0.8520(5) 0.4706(3) 0.0801(10) Uani 1 1 d . . . C18 C 1.2079(9) 0.8271(9) 0.5776(7) 0.0288(13) Uani 1 1 d . . . C34 C 1.1812(10) 1.0965(10) 0.9067(7) 0.0331(14) Uani 1 1 d . . . H34A H 1.0819 1.1897 0.9198 0.050 Uiso 1 1 calc R . . H34B H 1.3057 1.1102 0.9113 0.050 Uiso 1 1 calc R . . H34C H 1.1814 0.9910 0.9763 0.050 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 Rh1 0.0276(3) 0.0309(3) 0.0262(3) -0.0098(2) 0.00021(17) -0.01038(19) S32 0.0329(7) 0.0288(8) 0.0271(7) -0.0135(6) 0.0008(6) -0.0142(6) O11 0.029(2) 0.024(2) 0.0199(19) -0.0072(16) -0.0013(15) -0.0028(16) O31 0.030(2) 0.025(2) 0.041(3) -0.018(2) -0.0080(19) -0.0037(17) O1 0.042(3) 0.039(3) 0.035(3) -0.014(2) 0.007(2) -0.024(2) O2 0.027(2) 0.046(3) 0.037(3) -0.017(2) 0.0007(19) -0.006(2) C12 0.027(3) 0.023(3) 0.035(3) -0.012(2) -0.004(2) -0.009(2) N19 0.040(3) 0.031(3) 0.016(2) -0.008(2) 0.0018(19) -0.022(2) C13 0.038(4) 0.023(3) 0.054(5) -0.004(3) -0.014(3) -0.011(3) C16 0.022(3) 0.069(6) 0.112(8) -0.073(6) 0.010(4) -0.015(3) C14 0.040(4) 0.023(4) 0.125(10) -0.022(5) -0.043(6) 0.001(3) C15 0.027(4) 0.040(5) 0.154(12) -0.062(7) -0.017(5) 0.008(3) C17 0.022(3) 0.033(3) 0.046(4) -0.029(3) 0.005(2) -0.011(2) C33 0.101(8) 0.064(6) 0.036(4) 0.000(4) -0.013(5) -0.057(6) S18 0.131(3) 0.083(2) 0.0384(13) -0.0142(13) 0.0035(15) -0.061(2) C18 0.032(3) 0.044(4) 0.029(3) -0.026(3) 0.013(2) -0.025(3) C34 0.030(3) 0.045(4) 0.028(3) -0.016(3) 0.000(2) -0.014(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 Rh1 O1 1.700(5) . ? Rh1 O2 1.712(5) . ? Rh1 O11 1.953(4) . ? Rh1 N19 2.261(5) . ? Rh1 O31 2.305(5) . ? Rh1 S18 2.340(3) 2_776 ? S32 O31 1.537(5) . ? S32 C34 1.773(7) . ? S32 C33 1.784(9) . ? O11 C12 1.365(7) . ? C12 C13 1.390(10) . ? C12 C17 1.413(10) . ? N19 C18 1.323(9) . ? N19 N19 1.393(10) 2_776 ? C13 C14 1.397(13) . ? C16 C15 1.371(17) . ? C16 C17 1.432(9) . ? C14 C15 1.372(18) . ? C17 C18 1.458(10) . ? S18 C18 1.661(7) . ? S18 Rh1 2.340(3) 2_776 ? 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 O1 Rh1 O2 105.8(3) . . ? O1 Rh1 O11 97.3(2) . . ? O2 Rh1 O11 106.1(2) . . ? O1 Rh1 N19 91.5(2) . . ? O2 Rh1 N19 159.5(2) . . ? O11 Rh1 N19 81.92(19) . . ? O1 Rh1 O31 168.4(2) . . ? O2 Rh1 O31 85.8(2) . . ? O11 Rh1 O31 78.52(18) . . ? N19 Rh1 O31 77.27(18) . . ? O1 Rh1 S18 100.0(2) . 2_776 ? O2 Rh1 S18 87.4(2) . 2_776 ? O11 Rh1 S18 154.14(17) . 2_776 ? N19 Rh1 S18 78.59(17) . 2_776 ? O31 Rh1 S18 80.72(14) . 2_776 ? O31 S32 C34 105.5(3) . . ? O31 S32 C33 103.6(4) . . ? C34 S32 C33 99.2(4) . . ? C12 O11 Rh1 127.6(4) . . ? S32 O31 Rh1 123.6(2) . . ? O11 C12 C13 117.0(7) . . ? O11 C12 C17 121.6(6) . . ? C13 C12 C17 121.3(7) . . ? C18 N19 N19 115.4(6) . 2_776 ? C18 N19 Rh1 126.6(4) . . ? N19 N19 Rh1 117.4(6) 2_776 . ? C12 C13 C14 119.3(9) . . ? C15 C16 C17 122.1(10) . . ? C15 C14 C13 121.4(9) . . ? C16 C15 C14 119.4(7) . . ? C12 C17 C16 116.4(8) . . ? C12 C17 C18 123.7(5) . . ? C16 C17 C18 119.8(7) . . ? C18 S18 Rh1 101.0(3) . 2_776 ? N19 C18 C17 121.2(5) . . ? N19 C18 S18 126.8(6) . . ? C17 C18 S18 112.0(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 O1 Rh1 O11 C12 46.8(5) . . . . ? O2 Rh1 O11 C12 155.6(5) . . . . ? N19 Rh1 O11 C12 -43.7(5) . . . . ? O31 Rh1 O11 C12 -122.2(5) . . . . ? S18 Rh1 O11 C12 -85.0(6) 2_776 . . . ? C34 S32 O31 Rh1 -116.9(4) . . . . ? C33 S32 O31 Rh1 139.3(4) . . . . ? O1 Rh1 O31 S32 -33.2(12) . . . . ? O2 Rh1 O31 S32 144.3(4) . . . . ? O11 Rh1 O31 S32 36.8(3) . . . . ? N19 Rh1 O31 S32 -47.3(3) . . . . ? S18 Rh1 O31 S32 -127.6(4) 2_776 . . . ? Rh1 O11 C12 C13 -137.5(5) . . . . ? Rh1 O11 C12 C17 46.0(8) . . . . ? O1 Rh1 N19 C18 -80.5(5) . . . . ? O2 Rh1 N19 C18 131.6(6) . . . . ? O11 Rh1 N19 C18 16.7(5) . . . . ? O31 Rh1 N19 C18 96.7(5) . . . . ? S18 Rh1 N19 C18 179.6(5) 2_776 . . . ? O1 Rh1 N19 N19 108.7(5) . . . 2_776 ? O2 Rh1 N19 N19 -39.2(9) . . . 2_776 ? O11 Rh1 N19 N19 -154.1(5) . . . 2_776 ? O31 Rh1 N19 N19 -74.1(5) . . . 2_776 ? S18 Rh1 N19 N19 8.8(5) 2_776 . . 2_776 ? O11 C12 C13 C14 -175.3(6) . . . . ? C17 C12 C13 C14 1.2(10) . . . . ? C12 C13 C14 C15 -1.3(12) . . . . ? C17 C16 C15 C14 -2.1(12) . . . . ? C13 C14 C15 C16 1.7(12) . . . . ? O11 C12 C17 C16 174.9(5) . . . . ? C13 C12 C17 C16 -1.5(9) . . . . ? O11 C12 C17 C18 -3.4(9) . . . . ? C13 C12 C17 C18 -179.8(6) . . . . ? C15 C16 C17 C12 1.9(10) . . . . ? C15 C16 C17 C18 -179.7(7) . . . . ? N19 N19 C18 C17 -179.9(6) 2_776 . . . ? Rh1 N19 C18 C17 9.1(8) . . . . ? N19 N19 C18 S18 -1.2(9) 2_776 . . . ? Rh1 N19 C18 S18 -172.1(3) . . . . ? C12 C17 C18 N19 -22.2(9) . . . . ? C16 C17 C18 N19 159.5(6) . . . . ? C12 C17 C18 S18 158.9(5) . . . . ? C16 C17 C18 S18 -19.4(7) . . . . ? Rh1 S18 C18 N19 -5.5(6) 2_776 . . . ? Rh1 S18 C18 C17 173.3(4) 2_776 . . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 2.372 _refine_diff_density_min -3.570 _refine_diff_density_rms 0.221 _publ_section_references ; Oxford Diffraction Ltd, Crysalis Program (2005) Oxford Diffraction Ltd, Abspack Program (2005) Sheldrick, G.M. (1997) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (2004) PLATON program, Utrecht University, The Netherlands ; #===END # Attachment '- HTBH.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 766984' #TrackingRef '- HTBH.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 N4 O4 S2' _chemical_formula_weight 372.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' N N 0.0061 0.0033 '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/n 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 9.2078(4) _cell_length_b 7.9309(4) _cell_length_c 11.4536(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.796(4) _cell_angle_gamma 90.00 _cell_volume 836.00(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5426 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 29.99 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.346 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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_standards_number n/a _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 5426 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 29.99 _reflns_number_total 2337 _reflns_number_gt 1783 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _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 ; _refine_ls_weighting_details w=1/[\s^2^(Fo^2^)+(0.0528P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2337 _refine_ls_number_parameters 124 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0939 _refine_ls_wR_factor_gt 0.0905 _refine_ls_goodness_of_fit_ref 0.943 _refine_ls_restrained_S_all 0.943 _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 C11 C 0.16711(17) 0.36854(17) 0.44715(11) 0.0168(3) Uani 1 1 d . . . C12 C 0.28343(18) 0.36326(19) 0.52997(12) 0.0216(3) Uani 1 1 d . . . H12 H 0.3678 0.4231 0.5152 0.026 Uiso 1 1 calc R . . C13 C 0.27616(19) 0.2719(2) 0.63251(13) 0.0252(4) Uani 1 1 d . . . H13 H 0.3539 0.2722 0.6863 0.030 Uiso 1 1 calc R . . C14 C 0.15186(19) 0.17976(19) 0.65441(13) 0.0245(3) Uani 1 1 d . . . H14 H 0.1470 0.1166 0.7226 0.029 Uiso 1 1 calc R . . C15 C 0.03519(18) 0.18144(18) 0.57541(12) 0.0216(3) Uani 1 1 d . . . H15 H -0.0477 0.1193 0.5907 0.026 Uiso 1 1 calc R . . C16 C 0.04120(17) 0.27612(18) 0.47253(12) 0.0174(3) Uani 1 1 d . . . C17 C 0.18582(16) 0.47198(17) 0.33921(11) 0.0172(3) Uani 1 1 d . . . S17 S 0.34604(4) 0.55803(5) 0.30417(3) 0.02314(12) Uani 1 1 d . . . N17 N 0.06853(14) 0.49440(15) 0.27038(10) 0.0200(3) Uani 1 1 d . . . H17 H -0.0112 0.4472 0.2899 0.024 Uiso 1 1 calc R . . O16 O -0.07467(12) 0.27841(14) 0.39561(8) 0.0222(2) Uani 1 1 d D . . H16 H -0.1468(17) 0.233(2) 0.4282(14) 0.027 Uiso 1 1 d D . . O1 O 0.31823(13) 0.83723(15) 0.51695(10) 0.0279(3) Uani 1 1 d D . . H1 H 0.341(2) 0.764(2) 0.4684(13) 0.033 Uiso 1 1 d D . . H2 H 0.3823(19) 0.867(2) 0.5627(14) 0.033 Uiso 1 1 d D . . N18 N 0.06734(17) 0.59182(18) 0.16648(11) 0.0269(3) Uani 1 1 d D . . H181 H 0.126(2) 0.545(2) 0.1215(14) 0.032 Uiso 1 1 d D . . H182 H 0.103(2) 0.6897(18) 0.1859(14) 0.032 Uiso 1 1 d 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 C11 0.0185(8) 0.0157(7) 0.0161(6) -0.0021(5) -0.0012(6) 0.0014(5) C12 0.0185(8) 0.0231(8) 0.0228(7) -0.0004(6) -0.0037(6) -0.0011(6) C13 0.0270(9) 0.0260(8) 0.0221(7) 0.0011(6) -0.0073(7) 0.0020(6) C14 0.0315(10) 0.0231(8) 0.0190(6) 0.0025(6) -0.0009(6) 0.0029(6) C15 0.0245(9) 0.0198(7) 0.0206(7) -0.0002(5) 0.0020(6) -0.0023(6) C16 0.0173(8) 0.0186(7) 0.0162(6) -0.0042(5) -0.0006(6) 0.0001(5) C17 0.0176(8) 0.0173(7) 0.0166(6) -0.0032(5) -0.0001(5) 0.0004(5) S17 0.0181(2) 0.0294(2) 0.02189(19) 0.00222(15) 0.00101(14) -0.00434(15) N17 0.0189(7) 0.0222(6) 0.0188(6) 0.0042(5) -0.0021(5) -0.0032(5) O16 0.0172(6) 0.0298(6) 0.0194(5) 0.0018(4) -0.0013(4) -0.0064(4) O1 0.0218(7) 0.0366(7) 0.0251(6) -0.0061(5) -0.0018(5) -0.0077(5) N18 0.0307(9) 0.0306(8) 0.0192(6) 0.0068(5) -0.0046(6) -0.0078(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11 C12 1.409(2) . ? C11 C16 1.410(2) . ? C11 C17 1.4982(19) . ? C12 C13 1.383(2) . ? C13 C14 1.387(2) . ? C14 C15 1.383(2) . ? C15 C16 1.3998(19) . ? C16 O16 1.3623(17) . ? C17 N17 1.3289(19) . ? C17 S17 1.6853(15) . ? N17 N18 1.4187(16) . ? 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 C12 C11 C16 117.29(13) . . ? C12 C11 C17 117.85(13) . . ? C16 C11 C17 124.85(13) . . ? C13 C12 C11 122.08(15) . . ? C12 C13 C14 119.44(15) . . ? C15 C14 C13 120.34(14) . . ? C14 C15 C16 120.37(15) . . ? O16 C16 C15 120.05(14) . . ? O16 C16 C11 119.49(12) . . ? C15 C16 C11 120.46(14) . . ? N17 C17 C11 116.77(13) . . ? N17 C17 S17 120.38(11) . . ? C11 C17 S17 122.85(11) . . ? C17 N17 N18 123.73(13) . . ? 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 C16 C11 C12 C13 -0.1(2) . . . . ? C17 C11 C12 C13 179.71(14) . . . . ? C11 C12 C13 C14 1.1(2) . . . . ? C12 C13 C14 C15 -1.1(2) . . . . ? C13 C14 C15 C16 0.0(2) . . . . ? C14 C15 C16 O16 -179.40(13) . . . . ? C14 C15 C16 C11 1.1(2) . . . . ? C12 C11 C16 O16 179.45(13) . . . . ? C17 C11 C16 O16 -0.3(2) . . . . ? C12 C11 C16 C15 -1.1(2) . . . . ? C17 C11 C16 C15 179.18(13) . . . . ? C12 C11 C17 N17 -170.89(13) . . . . ? C16 C11 C17 N17 8.9(2) . . . . ? C12 C11 C17 S17 8.96(18) . . . . ? C16 C11 C17 S17 -171.28(11) . . . . ? C11 C17 N17 N18 178.62(12) . . . . ? S17 C17 N17 N18 -1.23(19) . . . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.285 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.057 _publ_section_references ; Oxford Diffraction Ltd, Crysalis Program (2005) Oxford Diffraction Ltd, Abspack Program (2005) Sheldrick, G.M. (1997) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (2004) PLATON program, Utrecht University, The Netherlands ;