# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2004 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_requested_category FO # TITLE AND AUTHOR LIST _publ_contact_author_name 'ProfD Lech Kozerski' _publ_contact_author_address ; NMR National Institute of Public Health Chelmska 30/34 Warsaw 00-725 POLAND ; _publ_section_title ; Hydrogen bond in "push - pull" enamines ; loop_ _publ_author_name _publ_author_address L.Kozerski ; National Institute of Public Health, Chelmska 30/34, 00-725 Warsaw, Poland and Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224 Warsaw, Poland ; B.Kwiecien ; Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224 Warsaw, Poland ; R.Kawecki ; Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224 Warsaw, Poland ; Z.Urbanczyk-Lipkowska ; Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224 Warsaw, Poland ; ; W.Bocian ; ; National Institute of Public Health, Chelmska 30/34, 00-725 Warsaw, Poland ; E.Bednarek ; National Institute of Public Health, Chelmska 30/34, 00-725 Warsaw, Poland and Industrial Chemistry Research Institute, Rydygiera 8, 01-793 Warszawa, Poland ; J.Sitkowski ; National Institute of Public Health, Chelmska 30/34, 00-725 Warsaw, Poland and Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224 Warsaw, Poland ; J.K.Maurin ; National Institute of Public Health, Chelmska 30/34, 00-725 Warsaw, Poland and Institute of Atomic Energy 05-400 Otwock-Swierk Poland ; L.Pazderski ; Department of Chemistry, Nicolaus Copernicus University, Gagarina 7, 87-100 Torun, Poland ; P.E.Hansen ; Institute of Life Sciences and Chemistry, Roskilde University, 4000 Roskilde, Denmark ; _publ_contact_author_email LKOZ@IL.WAW.PL data_8 _database_code_depnum_ccdc_archive 'CCDC 233419' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H15 N O2 S' _chemical_formula_weight 177.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 5.3858(3) _cell_length_b 13.3905(9) _cell_length_c 13.4835(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.434(9) _cell_angle_gamma 90.00 _cell_volume 966.29(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15 _cell_measurement_theta_min 21.61 _cell_measurement_theta_max 23.44 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 2.645 _exptl_absorpt_correction_type 'not applied' _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'MACH3 \k-axis diffractometer' _diffrn_measurement_method 'separate \w-2\q scans for individual reflections' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 1794 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.67 _diffrn_reflns_theta_max 73.28 _reflns_number_total 1614 _reflns_number_gt 1587 _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 'XP (Bruker-AXS, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1100P)^2^+0.2472P] 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 SHELXL _refine_ls_extinction_coef 0.135(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1614 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1474 _refine_ls_wR_factor_gt 0.1447 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.19359(10) 0.33914(4) 0.48415(4) 0.0449(3) Uani 1 1 d . . . O1 O 0.2798(4) 0.41127(17) 0.41642(13) 0.0611(6) Uani 1 1 d . . . O2 O 0.2466(4) 0.23551(15) 0.46505(15) 0.0605(6) Uani 1 1 d . . . N1 N 0.3931(5) 0.35415(17) 0.77711(17) 0.0539(6) Uani 1 1 d . . . H1 H 0.344(6) 0.329(3) 0.821(3) 0.057(9) Uiso 1 1 d . . . C1 C -0.1341(5) 0.3495(2) 0.4748(3) 0.0609(7) Uani 1 1 d . . . H1A H -0.1986 0.3025 0.5192 0.069(10) Uiso 1 1 calc R . . H1B H -0.2035 0.3358 0.4075 0.078(11) Uiso 1 1 calc R . . H1C H -0.1789 0.4160 0.4927 0.079(11) Uiso 1 1 calc R . . C2 C 0.3134(5) 0.37515(19) 0.60135(17) 0.0448(6) Uani 1 1 d . . . H2 H 0.409(5) 0.435(2) 0.604(2) 0.050(7) Uiso 1 1 d . . . C3 C 0.2830(5) 0.32451(18) 0.68742(18) 0.0452(6) Uani 1 1 d . . . C4 C 0.1229(7) 0.2324(2) 0.6907(2) 0.0630(8) Uani 1 1 d . . . H4A H 0.1289 0.2092 0.7583 0.17(2) Uiso 1 1 calc R . . H4B H 0.1843 0.1811 0.6501 0.19(3) Uiso 1 1 calc R . . H4C H -0.0466 0.2482 0.6658 0.22(3) Uiso 1 1 calc R . . C5 C 0.5244(5) 0.4487(2) 0.79723(18) 0.0504(6) Uani 1 1 d . . . H5 H 0.6249 0.4625 0.7426 0.056(8) Uiso 1 1 calc R . . C6 C 0.6986(6) 0.4379(3) 0.8936(2) 0.0694(9) Uani 1 1 d . . . H6A H 0.8134 0.3841 0.8870 0.080(11) Uiso 1 1 calc R . . H6B H 0.6023 0.4240 0.9477 0.081(11) Uiso 1 1 calc R . . H6C H 0.7901 0.4989 0.9069 0.113(16) Uiso 1 1 calc R . . C7 C 0.3382(7) 0.5335(2) 0.8030(3) 0.0725(9) Uani 1 1 d . . . H7A H 0.2322 0.5380 0.7410 0.101(13) Uiso 1 1 calc R . . H7B H 0.4268 0.5952 0.8155 0.099(13) Uiso 1 1 calc R . . H7C H 0.2380 0.5206 0.8562 0.093(13) 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 0.0466(4) 0.0514(5) 0.0377(4) -0.0043(2) 0.0090(2) -0.0003(2) O1 0.0673(12) 0.0760(14) 0.0408(10) 0.0064(9) 0.0097(8) -0.0126(9) O2 0.0699(12) 0.0590(12) 0.0534(10) -0.0160(9) 0.0101(9) 0.0083(9) N1 0.0732(15) 0.0522(13) 0.0373(11) 0.0047(9) 0.0106(10) -0.0129(10) C1 0.0472(14) 0.0661(18) 0.0691(18) 0.0002(14) 0.0044(12) 0.0024(11) C2 0.0522(13) 0.0457(12) 0.0376(11) -0.0017(9) 0.0097(9) -0.0045(10) C3 0.0538(13) 0.0427(12) 0.0408(12) -0.0003(9) 0.0125(9) -0.0006(10) C4 0.083(2) 0.0525(15) 0.0538(16) 0.0011(12) 0.0107(14) -0.0165(14) C5 0.0590(15) 0.0525(14) 0.0403(12) -0.0005(10) 0.0080(10) -0.0087(11) C6 0.0705(19) 0.077(2) 0.0576(16) -0.0002(15) -0.0054(14) -0.0109(16) C7 0.081(2) 0.0606(18) 0.074(2) -0.0082(15) 0.0011(17) 0.0043(15) _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 O1 1.4414(19) . yes S1 O2 1.446(2) . yes S1 C2 1.708(2) . yes S1 C1 1.761(3) . yes N1 C3 1.346(3) . yes N1 C5 1.461(3) . yes N1 H1 0.76(3) . yes C1 H1A 0.9600 . no C1 H1B 0.9600 . no C1 H1C 0.9600 . no C2 C3 1.370(3) . yes C2 H2 0.95(3) . yes C3 C4 1.509(4) . yes C4 H4A 0.9600 . no C4 H4B 0.9600 . no C4 H4C 0.9600 . no C5 C7 1.523(4) . yes C5 C6 1.522(4) . yes C5 H5 0.9800 . no C6 H6A 0.9600 . no C6 H6B 0.9600 . no C6 H6C 0.9600 . no C7 H7A 0.9600 . no C7 H7B 0.9600 . no C7 H7C 0.9600 . no 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 S1 O2 116.50(12) . . yes O1 S1 C2 106.37(12) . . yes O2 S1 C2 111.97(12) . . yes O1 S1 C1 107.06(14) . . yes O2 S1 C1 106.23(13) . . yes C2 S1 C1 108.39(14) . . yes C3 N1 C5 125.3(2) . . yes C3 N1 H1 115(3) . . yes C5 N1 H1 116(3) . . yes S1 C1 H1A 109.5 . . no S1 C1 H1B 109.5 . . no H1A C1 H1B 109.5 . . no S1 C1 H1C 109.5 . . no H1A C1 H1C 109.5 . . no H1B C1 H1C 109.5 . . no C3 C2 S1 125.1(2) . . yes C3 C2 H2 119.9(18) . . yes S1 C2 H2 115.0(18) . . yes N1 C3 C2 122.2(2) . . yes N1 C3 C4 114.2(2) . . yes C2 C3 C4 123.6(2) . . yes C3 C4 H4A 109.5 . . no C3 C4 H4B 109.5 . . no H4A C4 H4B 109.5 . . no C3 C4 H4C 109.5 . . no H4A C4 H4C 109.5 . . no H4B C4 H4C 109.5 . . no N1 C5 C7 110.3(2) . . yes N1 C5 C6 108.4(2) . . yes C7 C5 C6 111.9(3) . . yes N1 C5 H5 108.7 . . no C7 C5 H5 108.7 . . no C6 C5 H5 108.7 . . no C5 C6 H6A 109.5 . . no C5 C6 H6B 109.5 . . no H6A C6 H6B 109.5 . . no C5 C6 H6C 109.5 . . no H6A C6 H6C 109.5 . . no H6B C6 H6C 109.5 . . no C5 C7 H7A 109.5 . . no C5 C7 H7B 109.5 . . no H7A C7 H7B 109.5 . . no C5 C7 H7C 109.5 . . no H7A C7 H7C 109.5 . . no H7B C7 H7C 109.5 . . no 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 S1 C2 C3 -177.6(2) . . . . no O2 S1 C2 C3 -49.3(3) . . . . no C1 S1 C2 C3 67.6(3) . . . . no C5 N1 C3 C2 9.4(4) . . . . no C5 N1 C3 C4 -169.8(3) . . . . no S1 C2 C3 N1 176.5(2) . . . . no S1 C2 C3 C4 -4.3(4) . . . . no C3 N1 C5 C7 77.8(3) . . . . no C3 N1 C5 C6 -159.3(3) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.76(3) 2.24(4) 2.989(3) 172(3) 4_566 C2 H2 O1 0.95(3) 2.69(3) 3.627(3) 169(2) 3_666 _diffrn_measured_fraction_theta_max 0.831 _diffrn_reflns_theta_full 73.28 _diffrn_measured_fraction_theta_full 0.831 _refine_diff_density_max 0.416 _refine_diff_density_min -0.785 _refine_diff_density_rms 0.151 data_15 _database_code_depnum_ccdc_archive 'CCDC 233420' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H17 N O2 S' _chemical_formula_weight 203.30 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.764(5) _cell_length_b 16.888(12) _cell_length_c 6.447(4) _cell_angle_alpha 90.00 _cell_angle_beta 115.20(7) _cell_angle_gamma 90.00 _cell_volume 567.8(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.5 _cell_measurement_theta_max 14 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_type 'not applied' _exptl_absorpt_process_details ? _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 'KUMA km-4 \k-axis diffractometer' _diffrn_measurement_method 'separate scans for individual reflections' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 4.17 _diffrn_reflns_number 1736 _diffrn_reflns_av_R_equivalents 0.0862 _diffrn_reflns_av_sigmaI/netI 0.0992 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 23.99 _reflns_number_total 935 _reflns_number_gt 560 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM-4 software (Kuma Diffraction, 2000)' _computing_cell_refinement 'KM-4 software (Kuma Diffraction, 2000)' _computing_data_reduction 'KM-4 software (Kuma Diffraction, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL v. 5.1 (Bruker-AXS, 1998)' _computing_publication_material 'SHELXTL v. 5.1 (Bruker-AXS, 1998)' _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^)+(0.1036P)^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 'not applied' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(3) _refine_ls_number_reflns 935 _refine_ls_number_parameters 124 _refine_ls_number_restraints 34 _refine_ls_R_factor_all 0.1155 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1522 _refine_ls_wR_factor_gt 0.1334 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.957 _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 1.0148(4) 0.49494(11) 0.6266(2) 0.0668(7) Uani 1 1 d D . . O1A O 1.098(4) 0.5512(9) 0.815(2) 0.066(7) Uiso 0.37(4) 1 d PD A 1 O1B O 1.172(2) 0.5611(4) 0.760(2) 0.072(4) Uiso 0.63(4) 1 d PD A 2 O2 O 0.9523(15) 0.4263(4) 0.7292(10) 0.106(2) Uani 1 1 d D A . N1 N 0.4285(12) 0.6289(4) 0.2451(10) 0.0628(16) Uani 1 1 d . A . H1 H 0.383(12) 0.606(4) 0.097(11) 0.042(15) Uiso 1 1 d . . . C1 C 0.7519(13) 0.5311(4) 0.3921(10) 0.0545(18) Uani 1 1 d . A . C2 C 0.7172(16) 0.4814(5) 0.1888(10) 0.067(2) Uani 1 1 d . . . H2A H 0.7065 0.5151 0.0632 0.080 Uiso 1 1 calc R A . H2B H 0.5591 0.4514 0.1391 0.080 Uiso 1 1 calc R . . C3 C 0.9404(17) 0.4258(5) 0.2528(12) 0.074(2) Uani 1 1 d . A . H3A H 0.9844 0.4195 0.1243 0.089 Uiso 1 1 calc R . . H3B H 0.8949 0.3742 0.2907 0.089 Uiso 1 1 calc R . . C4 C 1.1692(16) 0.4591(5) 0.4584(14) 0.076(2) Uani 1 1 d . A . H4A H 1.2525 0.5014 0.4139 0.091 Uiso 1 1 calc R . . H4B H 1.2937 0.4183 0.5381 0.091 Uiso 1 1 calc R . . C5 C 0.6324(14) 0.5976(4) 0.4072(11) 0.0511(16) Uani 1 1 d . . . H5 H 0.678(11) 0.615(3) 0.538(10) 0.025(13) Uiso 1 1 d . . . C6 C 0.3210(11) 0.7091(4) 0.2527(9) 0.0567(18) Uani 1 1 d D . . C7A C 0.506(3) 0.7741(9) 0.260(4) 0.079(7) Uiso 0.43(4) 1 d PD A 1 H7A1 H 0.5373 0.7710 0.1254 0.119 Uiso 0.43(4) 1 calc PR A 1 H7A2 H 0.6642 0.7678 0.3940 0.119 Uiso 0.43(4) 1 calc PR A 1 H7A3 H 0.4324 0.8248 0.2645 0.119 Uiso 0.43(4) 1 calc PR A 1 C8A C 0.071(3) 0.7164(11) 0.036(2) 0.062(6) Uiso 0.43(4) 1 d PD A 1 H8A1 H -0.0446 0.6753 0.0347 0.093 Uiso 0.43(4) 1 calc PR A 1 H8A2 H 0.1060 0.7115 -0.0960 0.093 Uiso 0.43(4) 1 calc PR A 1 H8A3 H -0.0048 0.7672 0.0345 0.093 Uiso 0.43(4) 1 calc PR A 1 C9A C 0.267(4) 0.7132(12) 0.464(3) 0.066(7) Uiso 0.43(4) 1 d PD A 1 H9A1 H 0.1473 0.6723 0.4554 0.099 Uiso 0.43(4) 1 calc PR A 1 H9A2 H 0.1946 0.7640 0.4694 0.099 Uiso 0.43(4) 1 calc PR A 1 H9A3 H 0.4234 0.7060 0.5988 0.099 Uiso 0.43(4) 1 calc PR A 1 C7B C 0.456(3) 0.7663(8) 0.157(4) 0.074(5) Uiso 0.57(4) 1 d PD A 2 H7B1 H 0.6361 0.7667 0.2552 0.111 Uiso 0.57(4) 1 calc PR A 2 H7B2 H 0.3872 0.8186 0.1497 0.111 Uiso 0.57(4) 1 calc PR A 2 H7B3 H 0.4286 0.7497 0.0061 0.111 Uiso 0.57(4) 1 calc PR A 2 C9B C 0.372(4) 0.7333(11) 0.4958(16) 0.093(6) Uiso 0.57(4) 1 d PD A 2 H9B1 H 0.5540 0.7337 0.5897 0.140 Uiso 0.57(4) 1 calc PR A 2 H9B2 H 0.2919 0.6962 0.5573 0.140 Uiso 0.57(4) 1 calc PR A 2 H9B3 H 0.3041 0.7853 0.4939 0.140 Uiso 0.57(4) 1 calc PR A 2 C8B C 0.0349(17) 0.7086(10) 0.101(3) 0.082(6) Uiso 0.57(4) 1 d PD A 2 H8B1 H 0.0051 0.6934 -0.0518 0.124 Uiso 0.57(4) 1 calc PR A 2 H8B2 H -0.0338 0.7606 0.0983 0.124 Uiso 0.57(4) 1 calc PR A 2 H8B3 H -0.0476 0.6715 0.1605 0.124 Uiso 0.57(4) 1 calc PR A 2 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 0.0742(11) 0.0684(11) 0.0403(7) -0.0036(11) 0.0075(6) 0.0139(11) O2 0.151(7) 0.107(5) 0.074(4) 0.036(4) 0.062(4) 0.030(5) N1 0.065(4) 0.065(3) 0.049(3) -0.016(3) 0.016(3) 0.009(3) C1 0.060(4) 0.058(4) 0.039(3) -0.003(3) 0.016(3) 0.007(3) C2 0.086(5) 0.064(5) 0.043(3) -0.013(4) 0.020(3) -0.002(4) C3 0.105(7) 0.074(5) 0.054(4) 0.002(4) 0.045(4) 0.017(5) C4 0.071(5) 0.071(5) 0.089(5) 0.015(4) 0.038(5) 0.014(4) C5 0.055(4) 0.058(4) 0.035(3) -0.007(3) 0.014(3) 0.000(4) C6 0.064(5) 0.048(4) 0.058(4) -0.009(3) 0.026(3) 0.008(4) _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 O2 1.454(5) . yes S1 O1A 1.455(6) . yes S1 O1B 1.464(5) . yes S1 C1 1.733(6) . yes S1 C4 1.777(9) . yes N1 C5 1.307(9) . yes N1 C6 1.499(9) . yes C1 C5 1.341(9) . yes C1 C2 1.497(9) . yes C2 C3 1.502(11) . yes C3 C4 1.525(12) . yes C6 C7A 1.517(7) . yes C6 C8B 1.517(7) . yes C6 C9A 1.521(7) . yes C6 C9B 1.522(7) . yes C6 C8A 1.523(7) . yes C6 C7B 1.524(7) . yes 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 S1 O1A 101.4(11) . . yes O2 S1 O1B 123.6(6) . . yes O1A S1 O1B 27.1(8) . . no O2 S1 C1 112.6(4) . . yes O1A S1 C1 110.7(6) . . yes O1B S1 C1 109.6(4) . . yes O2 S1 C4 107.0(4) . . yes O1A S1 C4 131.3(12) . . yes O1B S1 C4 105.8(8) . . yes C1 S1 C4 93.8(3) . . yes C5 N1 C6 125.7(5) . . yes C5 C1 C2 130.7(6) . . yes C5 C1 S1 121.1(5) . . yes C2 C1 S1 107.9(5) . . yes C1 C2 C3 109.3(5) . . yes C2 C3 C4 109.3(6) . . yes C3 C4 S1 100.6(5) . . yes N1 C5 C1 126.6(6) . . yes N1 C6 C7A 111.1(9) . . yes N1 C6 C8B 109.0(8) . . yes C7A C6 C8B 125.4(10) . . no N1 C6 C9A 108.4(8) . . yes C7A C6 C9A 110.4(4) . . yes C8B C6 C9A 89.7(7) . . no N1 C6 C9B 112.0(8) . . yes C7A C6 C9B 87.0(7) . . no C8B C6 C9B 110.3(5) . . yes C9A C6 C9B 24.7(7) . . no N1 C6 C8A 106.7(8) . . yes C7A C6 C8A 110.2(4) . . yes C8B C6 C8A 21.1(7) . . no C9A C6 C8A 109.9(4) . . yes C9B C6 C8A 127.9(10) . . no N1 C6 C7B 105.7(7) . . yes C7A C6 C7B 23.3(7) . . no C8B C6 C7B 110.1(4) . . yes C9A C6 C7B 131.8(8) . . no C9B C6 C7B 109.7(5) . . yes C8A C6 C7B 91.4(7) . . no 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 O2 S1 C1 C5 104.7(7) . . . . yes O1A S1 C1 C5 -8.0(14) . . . . yes O1B S1 C1 C5 -36.9(10) . . . . yes C4 S1 C1 C5 -145.1(7) . . . . yes O2 S1 C1 C2 -81.2(6) . . . . yes O1A S1 C1 C2 166.0(14) . . . . yes O1B S1 C1 C2 137.2(9) . . . . yes C4 S1 C1 C2 28.9(6) . . . . yes C5 C1 C2 C3 165.7(7) . . . . yes S1 C1 C2 C3 -7.6(8) . . . . yes C1 C2 C3 C4 -22.7(9) . . . . yes C2 C3 C4 S1 41.1(7) . . . . yes O2 S1 C4 C3 75.0(6) . . . . yes O1A S1 C4 C3 -162.0(10) . . . . yes O1B S1 C4 C3 -151.5(6) . . . . yes C1 S1 C4 C3 -40.0(5) . . . . yes C6 N1 C5 C1 -170.1(7) . . . . yes C2 C1 C5 N1 9.9(13) . . . . yes S1 C1 C5 N1 -177.6(7) . . . . yes C5 N1 C6 C7A 64.8(13) . . . . no C5 N1 C6 C8B -153.0(11) . . . . no C5 N1 C6 C9A -56.7(13) . . . . no C5 N1 C6 C9B -30.7(13) . . . . no C5 N1 C6 C8A -175.0(11) . . . . no C5 N1 C6 C7B 88.7(11) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1A 0.96(6) 2.08(7) 2.921(10) 146(5) 1_454 N1 H1 O1B 0.96(6) 2.13(7) 3.058(12) 163(5) 1_454 C3 H3A O2 0.97 2.48 3.405(9) 160.2 1_554 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.318 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.061