# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_compound_10 _database_code_CSD 178401 _journal_coden_Cambridge 207 loop_ _publ_author_name 'Henrik H. Jensen' 'Astrid Jensen' 'Rita G. Hazell' 'Mikael Bols' _publ_contact_author_name 'Prof Mikael Bols' _publ_contact_author_address ; Department of Chemistry Aarhus University Aarhus C DK-8000 DENMARK ; _publ_contact_author_phone ' 4589423963 ' _publ_contact_author_fax '..4586196199 ' _publ_contact_author_email mb@chem.au.dk _publ_requested_journal 'J. Chem. Soc. Perkin 1 ' # 3. TITLE AND AUTHOR LIST _publ_section_title ; Synthesis and investigation of L-fuco- and D-glucurono-azafagomine ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. #============================================================================== _publ_section_references ; Altomare,A., Cascarano,G., Giacovazzo,C., Guagliardi,A., Moliterni,.A,G,G., Burla,M.C., Polidori,G., Camalli,M. & Spagna,R. (1997). SIR97. University of Bari, Italy. Burnett,M.N. & Johnson,C.K. (1996). ORTEP-III. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Hazell,A. (1995). KRYSTAL, An integrated system of crystallographic programs. Aarhus University, Denmark. Siemens (1995) SMART, SAINT and XPREP Area-Detector Control and Integration Software. Siemens Analytical X-ray Instruments Inc. Madison, Wisconsin, USA. ; #============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; (3S,4R,5S)-1-N-Acetyl-4,5-isopropylidene-3-methyl-hexahydropyridazine ; _chemical_formula_sum C10H18N2O3 _chemical_formula_weight 214.27 #=================================== # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P21' loop_ _symmetry_equiv_pos_as_xyz '+x,+y,+z' '-x,1/2+y,-z' _cell_length_a 6.436(1) _cell_length_b 10.547(2) _cell_length_c 8.763(2) _cell_angle_alpha 90.000 _cell_angle_beta 105.899(3) _cell_angle_gamma 90.000 _cell_volume 572.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120 _cell_measurement_reflns_used 3812 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 30.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type 'none' _exptl_aabsorpt_process_details 'none' #=================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'x-ray tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation scans with narrow frames' _diffrn_reflns_number 6253 _diffrn_reflns_av_R_equivalents 0.078 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.4 _diffrn_reflns_theta_max 30.5 _diffrn_reflns_reduction_process 6253 _reflns_number_total 3168 _reflns_number_gt 2811 _reflns_threshold_expression I>3\s(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution ; SIR97 (Altomare et al., 1997 ), KRYSTAL ; _computing_structure_refinement 'modified ORFLS(1962), KRYSTAL' _computing_molecular_graphics ; ORTEP-III (Burnett & Johnson, 1996), KRYSTAL ; _computing_publication_material KRYSTAL _atom_type_scat_source IntTabIV #=================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w= 1/{[\s~cs~(F^2^)+1.03F^2^]^1/2^- |F|}^2^ ; _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method ; Type 1 Lorentzian isotropic ( Becker and Coppens, 1974) ; _refine_ls_extinction_coef 19(11) _refine_ls_number_reflns 2811 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_gt 0.039 _refine_ls_wR_factor_ref 0.046 _refine_ls_goodness_of_fit_ref 1.37 _refine_ls_shift/su_max 0.0012 _refine_ls_shift/su_mean 0.0001 _refine_diff_density_max 0.59(7) _refine_diff_density_min -0.36(7) #========================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type N1 0.3758(2) 0.2646 0.0546(1) 0.0178(6) Uij N2 0.2067(2) 0.1866(2) -0.0356(1) 0.0171(6) Uij C3 0.0054(2) 0.2078(2) 0.0103(2) 0.0172(6) Uij C4 0.0350(2) 0.2111(2) 0.1903(2) 0.0185(7) Uij C5 0.2372(2) 0.2786(2) 0.2875(2) 0.0189(7) Uij C6 0.4330(2) 0.2477(2) 0.2269(2) 0.0196(7) Uij C7 -0.1605(2) 0.1089(2) -0.0717(2) 0.0223(8) Uij O8 0.0675(2) 0.0864(2) 0.2606(1) 0.0217(5) Uij C9 0.1531(3) 0.1075(2) 0.4278(2) 0.0225(7) Uij O10 0.2666(2) 0.2273(2) 0.4436(1) 0.0236(6) Uij C11 0.4672(2) 0.3549(2) -0.0159(2) 0.0196(7) Uij C12 0.3853(3) 0.3661(2) -0.1940(2) 0.0299(9) Uij C13 0.3105(3) 0.0019(2) 0.4974(2) 0.0354(11) Uij C14 -0.0257(3) 0.1183(2) 0.5108(2) 0.0341(10) Uij O15 0.6121(2) 0.4245(2) 0.0630(1) 0.0254(6) Uij H2n 0.247(3) 0.106(2) -0.022(2) 0.020(4) Uiso H3 -0.041(2) 0.293(1) -0.024(2) 0.005(3) Uiso H4 -0.097(3) 0.249(2) 0.211(2) 0.015(4) Uiso H5 0.219(3) 0.368(2) 0.290(2) 0.013(4) Uiso H6a 0.566(3) 0.299(2) 0.276(2) 0.028(5) Uiso H6b 0.467(3) 0.160(2) 0.246(2) 0.013(4) Uiso H7a -0.299(3) 0.118(2) -0.043(2) 0.020(4) Uiso H7b -0.100(3) 0.026(2) -0.045(2) 0.023(4) Uiso H7c -0.196(3) 0.118(2) -0.189(2) 0.033(5) Uiso H12a 0.377(4) 0.287(3) -0.245(3) 0.056(7) Uiso H12b 0.474(4) 0.427(3) -0.228(3) 0.062(8) Uiso H12c 0.237(5) 0.398(3) -0.223(3) 0.065(8) Uiso H13a 0.362(3) 0.013(2) 0.614(3) 0.036(5) Uiso H13b 0.438(4) 0.004(2) 0.455(3) 0.046(6) Uiso H13c 0.224(5) -0.074(3) 0.472(3) 0.065(8) Uiso H14a 0.038(3) 0.138(2) 0.619(2) 0.026(5) Uiso H14b -0.100(4) 0.037(2) 0.505(3) 0.043(6) Uiso H14c -0.135(4) 0.182(2) 0.469(3) 0.042(6) Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.0192(6) 0.0209(6) 0.0137(5) -0.0034(5) 0.0055(4) -0.0011(4) N2 0.0187(6) 0.0175(6) 0.0157(5) -0.0018(4) 0.0055(4) -0.0024(4) C3 0.0189(6) 0.0192(6) 0.0135(5) -0.0001(5) 0.0046(5) 0.0004(5) C4 0.0208(6) 0.0206(6) 0.0155(6) 0.0020(6) 0.0075(5) 0.0004(5) C5 0.0252(7) 0.0191(7) 0.0132(6) 0.0005(6) 0.0066(5) -0.0001(5) C6 0.0201(7) 0.0235(7) 0.0142(6) -0.0030(5) 0.0031(5) 0.0000(5) C7 0.0220(7) 0.0269(8) 0.0180(7) -0.0048(6) 0.0053(5) -0.0023(6) O8 0.0298(5) 0.0223(5) 0.0130(4) -0.0045(4) 0.0057(4) 0.0022(4) C9 0.0274(7) 0.0270(7) 0.0134(6) -0.0016(6) 0.0061(5) 0.0017(5) O10 0.0302(6) 0.0295(6) 0.0110(4) -0.0047(4) 0.0055(4) 0.0001(4) C11 0.0206(7) 0.0192(7) 0.0227(7) 0.0021(5) 0.0120(5) 0.0012(5) C12 0.0413(10) 0.0296(8) 0.0220(7) -0.0045(8) 0.0138(7) 0.0037(6) C13 0.0483(12) 0.0346(10) 0.0217(8) 0.0080(9) 0.0068(8) 0.0066(7) C14 0.0317(9) 0.0536(12) 0.0198(7) -0.0073(9) 0.0121(7) 0.0024(8) O15 0.0249(5) 0.0232(6) 0.0298(6) -0.0049(4) 0.0106(4) 0.0007(5) #================================= # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C11 1.355(2) N1 N2 1.419(2) N1 C6 1.464(2) N2 C3 1.475(2) C3 C4 1.537(2) C3 C7 1.524(2) C4 C5 1.523(2) C4 O8 1.444(2) C5 C6 1.530(2) C5 O10 1.435(2) O8 C9 1.434(2) C9 O10 1.447(2) C9 C13 1.516(2) C9 C14 1.525(2) C11 C12 1.508(2) C11 O15 1.238(2) N2 H2n 0.883(20) C3 H3 0.975(15) C4 H4 0.996(17) C5 H5 0.946(17) C6 H6a 1.005(20) C6 H6b 0.955(18) C7 H7a 0.998(17) C7 H7b 0.963(21) C7 H7c 0.994(19) C12 H12a 0.943(27) C12 H12b 0.957(27) C12 H12c 0.974(29) C13 H13a 0.991(22) C13 H13b 0.988(24) C13 H13c 0.963(31) C14 H14a 0.946(20) C14 H14b 0.976(25) C14 H14c 0.975(24) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N2 N1 C6 116.2(1) N2 N1 C11 121.1(1) C6 N1 C11 122.6(1) N1 N2 C3 110.9(1) N2 C3 C4 114.3(1) N2 C3 C7 108.8(1) C4 C3 C7 111.9(1) C3 C4 C5 115.6(1) C3 C4 O8 112.3(1) C5 C4 O8 100.7(1) C4 C5 C6 111.4(1) C4 C5 O10 103.1(1) C6 C5 O10 110.1(1) N1 C6 C5 109.5(1) C4 O8 C9 105.4(1) O8 C9 O10 106.0(1) O8 C9 C13 108.9(1) O8 C9 C14 111.7(1) O10 C9 C13 109.8(1) O10 C9 C14 108.4(1) C13 C9 C14 111.8(1) C5 O10 C9 107.9(1) N1 C11 C12 117.0(1) N1 C11 O15 121.1(1) C12 C11 O15 121.8(1) N1 N2 H2n 109.2(11) C3 N2 H2n 110.7(12) N2 C3 H3 106.0(9) C7 C3 H3 111.8(9) C4 C3 H3 103.8(9) O8 C4 H4 108.5(10) C5 C4 H4 110.6(10) C3 C4 H4 108.8(10) O10 C5 H5 109.6(10) C4 C5 H5 112.7(11) C6 C5 H5 109.8(10) H6a C6 H6b 108.7(15) N1 C6 H6b 106.2(10) C5 C6 H6b 108.6(9) N1 C6 H6a 108.8(11) C5 C6 H6a 114.7(11) H7b C7 H7c 107.2(16) H7a C7 H7b 110.6(15) C3 C7 H7b 109.1(11) H7a C7 H7c 106.7(15) C3 C7 H7c 110.9(12) C3 C7 H7a 112.2(10) H12a C12 H12b 114.1(20) H12a C12 H12c 104.7(22) C11 C12 H12a 112.3(16) H12b C12 H12c 108.5(24) C11 C12 H12b 107.6(16) C11 C12 H12c 109.5(16) H13b C13 H13c 114.9(21) H13a C13 H13c 110.0(19) C9 C13 H13c 103.6(17) H13a C13 H13b 108.0(17) C9 C13 H13b 111.2(14) C9 C13 H13a 109.0(12) H14a C14 H14c 106.9(18) H14a C14 H14b 108.7(18) C9 C14 H14a 108.7(11) H14b C14 H14c 107.4(18) C9 C14 H14c 115.8(14) C9 C14 H14b 109.2(14) loop_ _publ_manuscript_incl_extra_item '_geom_bond_atom_site_label_D' '_geom_bond_atom_site_label_H' '_geom_contact_atom_site_label_A' '_geom_bond_distance_DH' '_geom_contact_distance_HA' '_geom_contact_distance_DA' '_geom_angle_DHA' '_geom_contact_site_symmetry_A' loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A N2 H2n O15 0.883(20) 2.194(20) 3.035(2) 159.0(16) 2_645