# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Karl Jorgensen' _publ_contact_author_email KAJ@CHEM.AU.DK _publ_section_title ; A modular and organocatalytic approach to gamma-butyrolactone autoregulators from Streptomycetes ; loop_ _publ_author_name 'Karl Jorgensen' 'Petteri Elsner' 'Hao Jiang.' 'Johanne B Nielsen' 'Filippo Pasi' # Attachment 'haoh.cif' data_hao _database_code_depnum_ccdc_archive 'CCDC 688507' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3R,4R)-3-(4-methylpentanoyl)-4-(nitromethyl)dihydrofuran-2(3H)-one ; _chemical_name_common ;(3R,4R)-3-(4-methylpentanoyl)-4-(nitromethyl)dihydrofuran- 2(3H)-one ; _chemical_melting_point ? _chemical_formula_moiety 'C11 H17 N O5' _chemical_formula_sum 'C11 H17 N O5' _chemical_formula_weight 243.26 _chemical_absolute_configuration unknown 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.6073(6) _cell_length_b 10.3774(11) _cell_length_c 20.890(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1215.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9977 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 30.14 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.612 _exptl_crystal_size_mid 0.354 _exptl_crystal_size_min 0.091 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2106 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_sigmaI/netI 0.0145 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 30.28 _reflns_number_total 2106 _reflns_number_gt 1915 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0503P)^2^+0.2667P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(10) _refine_ls_number_reflns 2106 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0846 _refine_ls_wR_factor_gt 0.0817 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 O4 O 0.4385(2) 0.71951(10) 1.00313(4) 0.0194(2) Uani 1 1 d . . . N N 0.4368(2) 0.81413(12) 0.96793(5) 0.0167(2) Uani 1 1 d . . . O1 O 0.9472(2) 0.70397(12) 0.81152(5) 0.0257(2) Uani 1 1 d . . . C2 C 0.5364(3) 0.64570(12) 0.80577(6) 0.0127(2) Uani 1 1 d . . . H2 H 0.4232 0.7068 0.7868 0.015 Uiso 1 1 calc R . . C3 C 0.5197(2) 0.65835(13) 0.87873(6) 0.0137(2) Uani 1 1 d . . . H3 H 0.6743 0.6379 0.8981 0.016 Uiso 1 1 calc R . . O5 O 0.4224(2) 0.92548(11) 0.98666(5) 0.0250(2) Uani 1 1 d . . . O3 O 0.4585(2) 0.44858(11) 0.74388(5) 0.0258(3) Uani 1 1 d . . . C7 C 0.8031(3) 0.66212(14) 0.70581(6) 0.0186(3) Uani 1 1 d . . . H7A H 0.6638 0.7017 0.6865 0.022 Uiso 1 1 calc R . . H7B H 0.8018 0.5715 0.6944 0.022 Uiso 1 1 calc R . . C5 C 0.4462(3) 0.79414(12) 0.89681(6) 0.0167(3) Uani 1 1 d . . . H5A H 0.5586 0.8547 0.8784 0.020 Uiso 1 1 calc R . . H5B H 0.2904 0.8121 0.8788 0.020 Uiso 1 1 calc R . . C9 C 1.0274(3) 0.71567(14) 0.60416(6) 0.0185(3) Uani 1 1 d . . . H9 H 0.8692 0.7408 0.5886 0.022 Uiso 1 1 calc R . . C8 C 1.0255(3) 0.72397(14) 0.67738(6) 0.0165(3) Uani 1 1 d . . . H8A H 1.1659 0.6811 0.6942 0.020 Uiso 1 1 calc R . . H8B H 1.0325 0.8137 0.6902 0.020 Uiso 1 1 calc R . . O2 O 0.3363(2) 0.46297(10) 0.84468(5) 0.0235(2) Uani 1 1 d . . . C6 C 0.7829(3) 0.67338(13) 0.77731(6) 0.0149(2) Uani 1 1 d . . . C1 C 0.4450(3) 0.50998(13) 0.79253(6) 0.0181(3) Uani 1 1 d . . . C4 C 0.3367(3) 0.55529(14) 0.89698(6) 0.0193(3) Uani 1 1 d . . . H4A H 0.3815 0.5137 0.9368 0.023 Uiso 1 1 calc R . . H4B H 0.1799 0.5934 0.9022 0.023 Uiso 1 1 calc R . . C10 C 1.0767(4) 0.57950(17) 0.58169(8) 0.0363(4) Uani 1 1 d . . . H10A H 0.9602 0.5221 0.5996 0.054 Uiso 1 1 calc R . . H10B H 1.2331 0.5538 0.5953 0.054 Uiso 1 1 calc R . . H10C H 1.0679 0.5762 0.5358 0.054 Uiso 1 1 calc R . . C11 C 1.2095(3) 0.80796(18) 0.57583(7) 0.0306(4) Uani 1 1 d . . . H11A H 1.1755 0.8940 0.5900 0.046 Uiso 1 1 calc R . . H11B H 1.2015 0.8044 0.5300 0.046 Uiso 1 1 calc R . . H11C H 1.3664 0.7837 0.5897 0.046 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 O4 0.0151(5) 0.0279(6) 0.0151(4) 0.0015(4) 0.0003(4) 0.0016(5) N 0.0115(5) 0.0238(6) 0.0148(4) -0.0044(4) 0.0008(4) -0.0018(5) O1 0.0158(5) 0.0451(7) 0.0162(4) -0.0004(4) -0.0013(4) -0.0044(6) C2 0.0134(5) 0.0133(5) 0.0115(5) -0.0002(4) 0.0004(5) -0.0006(5) C3 0.0143(6) 0.0152(6) 0.0115(5) -0.0001(4) 0.0002(4) 0.0004(5) O5 0.0271(6) 0.0242(5) 0.0235(5) -0.0108(4) 0.0014(5) -0.0016(5) O3 0.0361(6) 0.0215(5) 0.0198(4) -0.0069(4) 0.0047(5) -0.0076(5) C7 0.0184(6) 0.0251(7) 0.0123(5) -0.0021(5) 0.0017(5) -0.0042(6) C5 0.0225(6) 0.0158(6) 0.0117(5) -0.0015(4) 0.0005(5) -0.0003(6) C9 0.0176(6) 0.0247(7) 0.0131(5) 0.0006(5) 0.0016(5) 0.0001(6) C8 0.0155(6) 0.0198(6) 0.0142(5) -0.0011(5) 0.0004(5) -0.0014(5) O2 0.0369(6) 0.0161(5) 0.0175(4) -0.0013(4) 0.0054(4) -0.0080(5) C6 0.0160(6) 0.0161(6) 0.0125(5) 0.0004(4) 0.0011(4) 0.0006(5) C1 0.0203(6) 0.0160(6) 0.0179(5) -0.0003(5) 0.0003(5) -0.0026(6) C4 0.0260(7) 0.0165(6) 0.0153(5) 0.0003(5) 0.0033(5) -0.0035(6) C10 0.0525(12) 0.0282(8) 0.0283(7) -0.0092(6) 0.0154(9) -0.0020(9) C11 0.0323(9) 0.0355(9) 0.0240(7) 0.0087(6) 0.0064(7) -0.0054(8) _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 O4 N 1.2266(16) . ? N O5 1.2226(16) . ? N C5 1.5011(15) . ? O1 C6 1.2085(18) . ? C2 C1 1.5240(19) . ? C2 C6 1.5319(19) . ? C2 C3 1.5328(16) . ? C2 H2 0.9800 . ? C3 C5 1.5159(18) . ? C3 C4 1.530(2) . ? C3 H3 0.9800 . ? O3 C1 1.2019(16) . ? C7 C6 1.5026(17) . ? C7 C8 1.523(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C9 C10 1.514(2) . ? C9 C11 1.520(2) . ? C9 C8 1.5320(17) . ? C9 H9 0.9800 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? O2 C1 1.3402(17) . ? O2 C4 1.4532(16) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? 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 O5 N O4 124.43(11) . . ? O5 N C5 116.72(11) . . ? O4 N C5 118.84(11) . . ? C1 C2 C6 113.96(11) . . ? C1 C2 C3 103.83(10) . . ? C6 C2 C3 115.14(11) . . ? C1 C2 H2 107.8 . . ? C6 C2 H2 107.8 . . ? C3 C2 H2 107.8 . . ? C5 C3 C4 113.91(12) . . ? C5 C3 C2 110.11(10) . . ? C4 C3 C2 103.22(11) . . ? C5 C3 H3 109.8 . . ? C4 C3 H3 109.8 . . ? C2 C3 H3 109.8 . . ? C6 C7 C8 114.63(12) . . ? C6 C7 H7A 108.6 . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7B 108.6 . . ? C8 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? N C5 C3 112.62(11) . . ? N C5 H5A 109.1 . . ? C3 C5 H5A 109.1 . . ? N C5 H5B 109.1 . . ? C3 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? C10 C9 C11 110.16(14) . . ? C10 C9 C8 111.30(13) . . ? C11 C9 C8 110.97(12) . . ? C10 C9 H9 108.1 . . ? C11 C9 H9 108.1 . . ? C8 C9 H9 108.1 . . ? C7 C8 C9 111.79(11) . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? C1 O2 C4 111.75(11) . . ? O1 C6 C7 123.41(13) . . ? O1 C6 C2 120.52(11) . . ? C7 C6 C2 116.06(12) . . ? O3 C1 O2 121.53(13) . . ? O3 C1 C2 128.48(13) . . ? O2 C1 C2 109.98(11) . . ? O2 C4 C3 105.92(11) . . ? O2 C4 H4A 110.6 . . ? C3 C4 H4A 110.6 . . ? O2 C4 H4B 110.6 . . ? C3 C4 H4B 110.6 . . ? H4A C4 H4B 108.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 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 C1 C2 C3 C5 -143.26(12) . . . . ? C6 C2 C3 C5 91.45(14) . . . . ? C1 C2 C3 C4 -21.29(14) . . . . ? C6 C2 C3 C4 -146.58(12) . . . . ? O5 N C5 C3 166.96(13) . . . . ? O4 N C5 C3 -14.63(18) . . . . ? C4 C3 C5 N 67.02(16) . . . . ? C2 C3 C5 N -177.59(12) . . . . ? C6 C7 C8 C9 -176.73(12) . . . . ? C10 C9 C8 C7 -72.67(17) . . . . ? C11 C9 C8 C7 164.27(13) . . . . ? C8 C7 C6 O1 -14.7(2) . . . . ? C8 C7 C6 C2 164.28(12) . . . . ? C1 C2 C6 O1 -120.55(15) . . . . ? C3 C2 C6 O1 -0.71(19) . . . . ? C1 C2 C6 C7 60.42(15) . . . . ? C3 C2 C6 C7 -179.74(12) . . . . ? C4 O2 C1 O3 -178.54(15) . . . . ? C4 O2 C1 C2 0.63(17) . . . . ? C6 C2 C1 O3 -41.2(2) . . . . ? C3 C2 C1 O3 -167.23(17) . . . . ? C6 C2 C1 O2 139.71(13) . . . . ? C3 C2 C1 O2 13.68(16) . . . . ? C1 O2 C4 C3 -14.84(17) . . . . ? C5 C3 C4 O2 141.56(11) . . . . ? C2 C3 C4 O2 22.18(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.28 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.351 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.041