# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Ranu, Brindaban' _publ_contact_author_email ocbcr@iacs.res.in _publ_section_title ; Amphiphilic allylation of activated alkenes by allyl acetates and allylstannanes catalyzed by palladium nanoparticles: an easy access to stereodefined substituted cyclohexene derivatives ; loop_ _publ_author_name B.Ranu L.Adak S.Bhadra K.Chattopadhyay data_3a _database_code_depnum_ccdc_archive 'CCDC 787993' #TrackingRef '3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H14 N2 O2' _chemical_formula_sum 'C16 H14 N2 O2' _chemical_formula_weight 266.29 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 11.2763(14) _cell_length_b 7.4688(9) _cell_length_c 17.260(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.039(3) _cell_angle_gamma 90.00 _cell_volume 1416.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour gray _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9875 _exptl_absorpt_correction_T_max 0.9900 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13287 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.44 _reflns_number_total 2612 _reflns_number_gt 1894 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SMART 3' _computing_structure_solution 'BRUKER AXS SMART 3' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'BRUKER SHELXLTL' _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^)+(0.0906P)^2^+0.1880P] 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 2612 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1326 _refine_ls_wR_factor_gt 0.1162 _refine_ls_goodness_of_fit_ref 0.882 _refine_ls_restrained_S_all 0.882 _refine_ls_shift/su_max 0.036 _refine_ls_shift/su_mean 0.005 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 C13 C 0.66717(14) 1.2148(2) 0.51904(9) 0.0442(4) Uani 1 1 d . . . C10 C 0.76153(13) 1.0935(2) 0.56464(9) 0.0432(4) Uani 1 1 d . . . C7 C 0.92447(13) 0.8659(2) 0.67285(9) 0.0428(4) Uani 1 1 d . . . H7 H 0.8934 0.9268 0.7145 0.051 Uiso 1 1 calc R . . C12 C 0.81080(13) 0.7827(2) 0.61445(9) 0.0417(4) Uani 1 1 d . . . C14 C 0.84490(15) 0.7228(2) 0.54040(10) 0.0494(4) Uani 1 1 d . . . C4 C 1.01323(13) 0.7259(2) 0.71448(9) 0.0418(4) Uani 1 1 d . . . C9 C 0.88020(14) 1.1290(2) 0.57941(10) 0.0496(4) Uani 1 1 d . . . H9 H 0.9049 1.2330 0.5579 0.059 Uiso 1 1 calc R . . C8 C 0.97666(14) 1.0119(2) 0.62848(11) 0.0520(4) Uani 1 1 d . . . H8A H 1.0320 1.0856 0.6667 0.062 Uiso 1 1 calc R . . H8B H 1.0231 0.9564 0.5940 0.062 Uiso 1 1 calc R . . C2 C 1.09517(17) 0.5648(3) 0.83525(11) 0.0644(5) Uani 1 1 d . . . H2 H 1.0993 0.5471 0.8891 0.077 Uiso 1 1 calc R . . C11 C 0.71123(13) 0.9265(2) 0.59413(10) 0.0470(4) Uani 1 1 d . . . H11A H 0.6439 0.8816 0.5535 0.056 Uiso 1 1 calc R . . H11B H 0.6809 0.9543 0.6411 0.056 Uiso 1 1 calc R . . C3 C 1.02000(16) 0.6951(2) 0.79454(10) 0.0510(4) Uani 1 1 d . . . H3 H 0.9729 0.7636 0.8212 0.061 Uiso 1 1 calc R . . C15 C 0.76398(15) 0.6273(2) 0.65119(10) 0.0521(4) Uani 1 1 d . . . C5 C 1.08321(15) 0.6192(2) 0.67572(11) 0.0538(4) Uani 1 1 d . . . H5 H 1.0804 0.6373 0.6220 0.065 Uiso 1 1 calc R . . C6 C 1.15696(16) 0.4862(3) 0.71700(12) 0.0641(5) Uani 1 1 d . . . H6 H 1.2019 0.4137 0.6905 0.077 Uiso 1 1 calc R . . C1 C 1.16426(17) 0.4605(3) 0.79659(12) 0.0672(5) Uani 1 1 d . . . H1 H 1.2156 0.3732 0.8243 0.081 Uiso 1 1 calc R . . N2 N 0.87285(16) 0.6850(3) 0.48303(10) 0.0740(5) Uani 1 1 d . . . N1 N 0.72513(16) 0.5102(3) 0.67971(11) 0.0781(5) Uani 1 1 d . . . O2 O 0.56197(10) 1.20819(17) 0.52296(7) 0.0589(4) Uani 1 1 d . . . O1 O 0.70920(10) 1.32836(17) 0.47228(8) 0.0597(4) Uani 1 1 d . . . C16 C 0.61942(18) 1.4459(3) 0.42471(13) 0.0711(6) Uani 1 1 d . . . H16A H 0.6582 1.5226 0.3932 0.107 Uiso 1 1 calc R . . H16B H 0.5825 1.5175 0.4590 0.107 Uiso 1 1 calc R . . H16C H 0.5581 1.3756 0.3903 0.107 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 C13 0.0428(9) 0.0447(9) 0.0451(9) -0.0032(7) 0.0102(7) -0.0037(7) C10 0.0399(8) 0.0461(9) 0.0437(9) -0.0004(7) 0.0094(7) -0.0024(7) C7 0.0383(8) 0.0467(9) 0.0426(8) -0.0029(7) 0.0076(7) -0.0019(7) C12 0.0375(8) 0.0466(9) 0.0416(8) 0.0026(7) 0.0103(7) -0.0077(7) C14 0.0465(9) 0.0523(10) 0.0491(10) -0.0014(8) 0.0101(8) -0.0111(8) C4 0.0357(8) 0.0466(9) 0.0425(8) -0.0014(7) 0.0074(6) -0.0034(7) C9 0.0437(9) 0.0445(9) 0.0601(10) 0.0073(8) 0.0109(8) -0.0055(7) C8 0.0374(8) 0.0491(9) 0.0664(11) 0.0030(8) 0.0050(8) -0.0061(7) C2 0.0680(12) 0.0741(13) 0.0494(10) 0.0116(9) 0.0098(9) 0.0121(10) C11 0.0360(8) 0.0546(10) 0.0499(9) 0.0056(8) 0.0083(7) -0.0036(7) C3 0.0517(10) 0.0556(10) 0.0445(9) -0.0033(8) 0.0086(7) 0.0054(8) C15 0.0461(9) 0.0579(10) 0.0528(10) 0.0066(8) 0.0123(8) -0.0091(8) C5 0.0503(10) 0.0643(11) 0.0513(10) 0.0036(8) 0.0207(8) 0.0049(8) C6 0.0548(11) 0.0641(11) 0.0797(14) 0.0036(10) 0.0287(10) 0.0146(9) C1 0.0574(11) 0.0700(12) 0.0733(13) 0.0179(10) 0.0129(10) 0.0170(10) N2 0.0797(12) 0.0906(12) 0.0561(10) -0.0151(9) 0.0248(9) -0.0133(10) N1 0.0779(11) 0.0756(11) 0.0848(12) 0.0164(10) 0.0271(10) -0.0219(10) O2 0.0410(7) 0.0663(8) 0.0691(8) 0.0087(6) 0.0119(6) 0.0019(6) O1 0.0484(7) 0.0613(7) 0.0701(8) 0.0219(6) 0.0151(6) 0.0064(6) C16 0.0619(12) 0.0705(13) 0.0796(14) 0.0273(11) 0.0132(10) 0.0127(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 C13 O2 1.2043(18) . ? C13 O1 1.3299(19) . ? C13 C10 1.481(2) . ? C10 C9 1.331(2) . ? C10 C11 1.505(2) . ? C7 C4 1.512(2) . ? C7 C8 1.524(2) . ? C7 C12 1.569(2) . ? C12 C15 1.476(2) . ? C12 C14 1.484(2) . ? C12 C11 1.536(2) . ? C14 N2 1.140(2) . ? C4 C3 1.386(2) . ? C4 C5 1.394(2) . ? C9 C8 1.500(2) . ? C2 C3 1.375(3) . ? C2 C1 1.376(3) . ? C15 N1 1.138(2) . ? C5 C6 1.385(3) . ? C6 C1 1.371(3) . ? O1 C16 1.447(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 O2 C13 O1 123.39(15) . . ? O2 C13 C10 122.95(14) . . ? O1 C13 C10 113.64(13) . . ? C9 C10 C13 123.40(14) . . ? C9 C10 C11 122.65(14) . . ? C13 C10 C11 113.95(12) . . ? C4 C7 C8 116.35(12) . . ? C4 C7 C12 112.85(12) . . ? C8 C7 C12 108.21(12) . . ? C15 C12 C14 108.65(13) . . ? C15 C12 C11 109.52(12) . . ? C14 C12 C11 109.40(13) . . ? C15 C12 C7 110.80(13) . . ? C14 C12 C7 109.86(12) . . ? C11 C12 C7 108.59(12) . . ? N2 C14 C12 176.69(18) . . ? C3 C4 C5 118.27(15) . . ? C3 C4 C7 118.05(13) . . ? C5 C4 C7 123.57(14) . . ? C10 C9 C8 124.17(15) . . ? C9 C8 C7 112.80(13) . . ? C3 C2 C1 120.26(17) . . ? C10 C11 C12 110.16(11) . . ? C2 C3 C4 121.07(16) . . ? N1 C15 C12 178.08(19) . . ? C6 C5 C4 120.15(16) . . ? C1 C6 C5 120.61(17) . . ? C6 C1 C2 119.62(17) . . ? C13 O1 C16 115.59(13) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.44 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.152 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.030 # Attachment '3b.cif' data_3b _database_code_depnum_ccdc_archive 'CCDC 787994' #TrackingRef '3b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 N2 O2 S' _chemical_formula_sum 'C14 H12 N2 O2 S' _chemical_formula_weight 272.32 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 monoclinic _symmetry_space_group_name_H-M P2(1)/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 9.031(8) _cell_length_b 7.178(6) _cell_length_c 21.954(18) _cell_angle_alpha 90.00 _cell_angle_beta 93.07(2) _cell_angle_gamma 90.00 _cell_volume 1421(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13038 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 25.3 _exptl_crystal_description block _exptl_crystal_colour gray _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.226 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9604 _exptl_absorpt_correction_T_max 0.9668 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13038 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.30 _reflns_number_total 2561 _reflns_number_gt 1743 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SMART 3' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'BRUKER SHELXLTL' _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^)+(0.2000P)^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 2561 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1480 _refine_ls_R_factor_gt 0.1208 _refine_ls_wR_factor_ref 0.4144 _refine_ls_wR_factor_gt 0.3785 _refine_ls_goodness_of_fit_ref 1.644 _refine_ls_restrained_S_all 1.644 _refine_ls_shift/su_max 0.041 _refine_ls_shift/su_mean 0.008 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 -0.0648(3) -0.0592(4) 0.27440(11) 0.1272(12) Uani 1 1 d . . . C12 C -0.2292(4) 0.0332(5) 0.36753(16) 0.0277(9) Uani 1 1 d . . . H12 H -0.2648 0.0757 0.4040 0.033 Uiso 1 1 calc R . . N2 N 0.0323(6) -0.2379(7) 0.4736(2) 0.0733(15) Uani 1 1 d . . . O1 O 0.5611(4) 0.2747(6) 0.48553(18) 0.0727(13) Uani 1 1 d . . . O2 O 0.5730(4) 0.4427(5) 0.40015(19) 0.0721(12) Uani 1 1 d . . . C7 C 0.1768(5) -0.0087(7) 0.4045(2) 0.0487(12) Uani 1 1 d . . . C11 C -0.0674(5) 0.0453(8) 0.3417(2) 0.0571(14) Uani 1 1 d . . . C6 C 0.0652(5) 0.1340(7) 0.3750(2) 0.0506(12) Uani 1 1 d . . . C8 C 0.2967(5) 0.0957(7) 0.4455(2) 0.0507(13) Uani 1 1 d . . . H8A H 0.2518 0.1444 0.4814 0.061 Uiso 1 1 calc R . . H8B H 0.3743 0.0093 0.4589 0.061 Uiso 1 1 calc R . . C4 C 0.2954(6) 0.3269(7) 0.3607(2) 0.0576(14) Uani 1 1 d . . . H4 H 0.3438 0.4221 0.3410 0.069 Uiso 1 1 calc R . . N1 N 0.3085(6) -0.1969(7) 0.3209(3) 0.0812(16) Uani 1 1 d . . . C3 C 0.3628(5) 0.2538(7) 0.4106(2) 0.0504(12) Uani 1 1 d . . . C5 C 0.1461(6) 0.2658(8) 0.3341(2) 0.0620(14) Uani 1 1 d . . . H5A H 0.1593 0.2048 0.2953 0.074 Uiso 1 1 calc R . . H5B H 0.0850 0.3752 0.3262 0.074 Uiso 1 1 calc R . . C9 C 0.2497(6) -0.1168(7) 0.3581(2) 0.0562(13) Uani 1 1 d . . . C1 C 0.7117(7) 0.5252(9) 0.4229(3) 0.0812(19) Uani 1 1 d . . . H1A H 0.7475 0.6085 0.3928 0.122 Uiso 1 1 calc R . . H1B H 0.7835 0.4286 0.4313 0.122 Uiso 1 1 calc R . . H1C H 0.6960 0.5930 0.4597 0.122 Uiso 1 1 calc R . . C2 C 0.5066(6) 0.3238(7) 0.4368(2) 0.0567(13) Uani 1 1 d . . . C13 C -0.3081(8) -0.0705(13) 0.3137(5) 0.109(3) Uani 1 1 d . . . H13 H -0.4081 -0.1011 0.3138 0.131 Uiso 1 1 calc R . . C14 C -0.2299(10) -0.1130(13) 0.2684(4) 0.107(3) Uani 1 1 d . . . H14 H -0.2709 -0.1729 0.2339 0.129 Uiso 1 1 calc R . . C10 C 0.0958(5) -0.1408(7) 0.4430(2) 0.0526(13) 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 S1 0.1027(19) 0.169(2) 0.1067(18) -0.0428(15) -0.0239(13) 0.0081(15) C12 0.0201(17) 0.0349(19) 0.0283(17) -0.0033(14) 0.0034(13) -0.0001(14) N2 0.074(3) 0.080(3) 0.067(3) 0.016(3) 0.009(2) -0.021(3) O1 0.067(2) 0.078(3) 0.071(2) 0.015(2) -0.0227(19) -0.0195(19) O2 0.069(3) 0.067(2) 0.080(3) 0.013(2) 0.002(2) -0.0230(19) C7 0.046(3) 0.056(3) 0.045(2) 0.005(2) 0.002(2) -0.007(2) C11 0.042(3) 0.065(3) 0.064(3) 0.000(2) -0.002(2) 0.002(2) C6 0.051(3) 0.057(3) 0.044(2) 0.002(2) -0.004(2) -0.001(2) C8 0.052(3) 0.052(3) 0.047(3) 0.007(2) -0.010(2) -0.010(2) C4 0.058(3) 0.057(3) 0.058(3) 0.019(2) 0.004(2) -0.010(2) N1 0.077(4) 0.091(4) 0.077(3) -0.009(3) 0.021(3) 0.006(3) C3 0.049(3) 0.054(3) 0.048(3) 0.005(2) 0.003(2) -0.005(2) C5 0.069(3) 0.066(3) 0.050(3) 0.016(2) -0.005(2) -0.003(3) C9 0.057(3) 0.059(3) 0.053(3) 0.004(2) 0.003(2) -0.006(2) C1 0.064(4) 0.077(4) 0.102(5) 0.002(3) 0.002(3) -0.027(3) C2 0.059(3) 0.044(3) 0.068(3) 0.004(2) 0.006(3) -0.003(2) C13 0.056(4) 0.107(6) 0.162(8) 0.031(6) -0.028(5) -0.021(4) C14 0.098(6) 0.114(6) 0.104(6) -0.021(5) -0.042(5) 0.004(5) C10 0.047(3) 0.058(3) 0.052(3) 0.001(2) -0.003(2) -0.010(2) _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 C14 1.540(9) . ? S1 C11 1.659(6) . ? C12 C13 1.539(11) . ? C12 C11 1.597(6) . ? N2 C10 1.144(6) . ? O1 C2 1.206(6) . ? O2 C2 1.337(6) . ? O2 C1 1.451(7) . ? C7 C9 1.464(7) . ? C7 C10 1.489(7) . ? C7 C6 1.554(7) . ? C7 C8 1.563(6) . ? C11 C6 1.509(7) . ? C6 C5 1.518(7) . ? C8 C3 1.510(6) . ? C4 C3 1.332(7) . ? C4 C5 1.506(7) . ? N1 C9 1.151(6) . ? C3 C2 1.480(7) . ? C13 C14 1.286(12) . ? 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 C14 S1 C11 97.5(4) . . ? C13 C12 C11 98.5(5) . . ? C2 O2 C1 117.4(5) . . ? C9 C7 C10 108.1(4) . . ? C9 C7 C6 111.4(4) . . ? C10 C7 C6 109.2(4) . . ? C9 C7 C8 109.4(4) . . ? C10 C7 C8 108.9(4) . . ? C6 C7 C8 109.8(4) . . ? C6 C11 C12 124.7(4) . . ? C6 C11 S1 124.9(4) . . ? C12 C11 S1 110.4(3) . . ? C11 C6 C5 111.8(4) . . ? C11 C6 C7 113.8(4) . . ? C5 C6 C7 109.6(4) . . ? C3 C8 C7 110.4(3) . . ? C3 C4 C5 124.4(4) . . ? C4 C3 C2 122.6(4) . . ? C4 C3 C8 122.5(4) . . ? C2 C3 C8 114.9(4) . . ? C4 C5 C6 113.7(4) . . ? N1 C9 C7 178.0(5) . . ? O1 C2 O2 123.0(5) . . ? O1 C2 C3 123.6(4) . . ? O2 C2 C3 113.3(4) . . ? C14 C13 C12 117.2(6) . . ? C13 C14 S1 116.3(6) . . ? N2 C10 C7 178.0(6) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.541 _refine_diff_density_min -1.033 _refine_diff_density_rms 0.128