# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Rohan Davis' _publ_contact_author_email R.DAVIS@GRIFFITH.EDU.AU _publ_section_title ; Pestalactams A-C: Novel caprolactams from the endophytic fungus Pestalotiopsis sp. ; loop_ _publ_author_name 'Rohan Davis' 'Katherine T. Andrews' 'Glen M. Boyle' 'Anthony R. Carroll' 'Peter Healy' 'John Kalaitzis' ; Truc Linh Tran ; 'Roger G. Shivas' # Attachment '633rq38.cif' data_1_633rq38 _database_code_depnum_ccdc_archive 'CCDC 748402' #TrackingRef '633rq38.cif' #=============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common 'Pestalactam A' _chemical_melting_point ? _chemical_formula_moiety 'C10 H12 Cl N O4' _chemical_formula_structural ? _chemical_formula_sum 'C10 H12 Cl N O4' _chemical_formula_iupac ? _chemical_formula_weight 245.66 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 21/a' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,-z 3 -x,-y,-z 4 1/2+x,1/2-y,z _cell_length_a 14.466(4) _cell_length_b 6.5627(19) _cell_length_c 12.390(4) _cell_angle_alpha 90 _cell_angle_beta 111.88(2) _cell_angle_gamma 90 _cell_volume 1091.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 295 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.5 _cell_measurement_theta_max 17.2 _cell_special_details ; ; _exptl_crystal_description needles _exptl_crystal_colour 'pale red' _exptl_crystal_size_max 0.550 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.150 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.348 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_absorpt_correction_T_min 0.832 _exptl_absorpt_correction_T_max 0.950 #=============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; The scan width was (1.79+0.30tan\q)\% with an \w scan speed of 16\% per minute (up to 4 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 2.44 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 2 0 -2 1 1 0 2 1 # number of measured reflections (redundant set) _diffrn_reflns_number 2152 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1919 # number of observed reflections (> n sig(I)) _reflns_number_gt 1380 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'MSC/AFC7 Diffractometer Control (MSC, 1999)' _computing_cell_refinement 'MSC/AFC7 Diffractometer Control (MSC, 1999)' _computing_data_reduction 'teXsan for Windows (MSC, 2001)' _computing_structure_solution 'teXsan for Windows (MSC, 2001)' _computing_structure_refinement 'teXsan for Windows (MSC, 2001); SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'teXsan for Windows (MSC, 2001); PLATON (Spek, 2003)' _publ_section_references ; Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Molecular Structure Corporation (1999). MSC/AFC7 Diffractometer Control for Windows version 1.02. MSC, 9009 New Trails Drive, The Woodlands, TX 77381, USA. Molecular Structure Corporation. (2001). TeXsan for Windows. Single Crystal Structure Analysis Software. Version 1.06. MSC, 9009 New Trails Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D.C. & Mathews, F.S. (1968). Acta Cryst. A24, 351-359. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13. ; #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs 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^)+(0.0865P)^2^+1.8696P] 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_number_reflns 1919 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0933 _refine_ls_R_factor_gt 0.0633 _refine_ls_wR_factor_ref 0.1815 _refine_ls_wR_factor_gt 0.1608 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.854 _refine_diff_density_min -0.886 _refine_diff_density_rms 0.096 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Cl3 Cl Uani 0.49675(7) 0.19834(17) 0.72374(8) 1.000 0.0368(3) . . O2 O Uani 0.29516(19) 0.2124(5) 0.5814(2) 1.000 0.0426(9) . . O4 O Uani 0.61892(17) 0.2203(4) 0.5968(2) 1.000 0.0338(8) . . O5 O Uani 0.58736(19) 0.2706(5) 0.3815(2) 1.000 0.0395(10) . . O9 O Uani 0.2611(4) 0.1657(14) 0.0585(5) 1.000 0.167(4) . . N1 N Uani 0.2949(2) 0.2768(5) 0.4052(3) 1.000 0.0303(10) . . C2 C Uani 0.3450(3) 0.2372(6) 0.5218(3) 1.000 0.0281(11) . . C3 C Uani 0.4537(3) 0.2292(5) 0.5750(3) 1.000 0.0257(10) . . C4 C Uani 0.5235(3) 0.2400(5) 0.5264(3) 1.000 0.0256(11) . . C5 C Uani 0.5099(3) 0.2712(6) 0.4019(3) 1.000 0.0273(11) . . C6 C Uani 0.4155(3) 0.3059(6) 0.3115(3) 1.000 0.0300(11) . . C7 C Uani 0.3223(3) 0.3137(6) 0.3124(3) 1.000 0.0275(11) . . C8 C Uani 0.2348(3) 0.3665(7) 0.2037(4) 1.000 0.0422(14) . . C9 C Uani 0.1948(3) 0.1905(10) 0.1154(4) 1.000 0.0561(16) . . C10 C Uani 0.0976(6) 0.2599(14) 0.0241(7) 1.000 0.137(4) . . C11 C Uani 0.1805(6) -0.0018(10) 0.1700(5) 1.000 0.094(3) . . H1 H Uiso 0.23130 0.27860 0.38610 1.000 0.0360 . . H2 H Uiso 0.41860 0.32700 0.23730 1.000 0.0360 . . H3 H Uiso 0.08140 0.17390 -0.04150 1.000 0.1640 . . H4 H Uiso 0.66520 0.22620 0.56890 1.000 0.0400 . . H5 H Uiso 0.04710 0.25510 0.05510 1.000 0.1640 . . H6 H Uiso 0.14140 0.02600 0.21620 1.000 0.1140 . . H7 H Uiso 0.24290 -0.05450 0.21830 1.000 0.1140 . . H8A H Uiso 0.18230 0.41150 0.22640 1.000 0.0510 . . H8B H Uiso 0.25440 0.47450 0.16580 1.000 0.0510 . . H9 H Uiso 0.27380 0.04060 0.04770 1.000 0.1760 . . H10A H Uiso 0.10540 0.39630 0.00240 1.000 0.1640 . . H11A H Uiso 0.14620 -0.09710 0.11150 1.000 0.1140 . . 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 Cl3 0.0300(5) 0.0529(7) 0.0269(5) -0.0010(4) 0.0099(4) -0.0006(4) O2 0.0209(13) 0.076(2) 0.0335(14) 0.0041(15) 0.0132(12) 0.0006(13) O4 0.0157(12) 0.0505(17) 0.0347(14) -0.0007(13) 0.0089(11) 0.0012(11) O5 0.0243(14) 0.0579(19) 0.0414(16) -0.0024(14) 0.0182(12) -0.0019(13) O9 0.097(4) 0.314(10) 0.124(5) -0.143(6) 0.082(4) -0.074(5) N1 0.0144(14) 0.0443(19) 0.0323(17) -0.0013(14) 0.0088(13) 0.0023(13) C2 0.0211(18) 0.034(2) 0.032(2) -0.0019(15) 0.0132(16) -0.0005(15) C3 0.0239(18) 0.0263(18) 0.0271(18) -0.0050(14) 0.0098(15) -0.0010(15) C4 0.0202(17) 0.0229(19) 0.0331(19) -0.0057(14) 0.0094(15) -0.0018(13) C5 0.0223(18) 0.0252(19) 0.037(2) -0.0030(15) 0.0141(16) -0.0011(14) C6 0.0247(18) 0.038(2) 0.0287(18) 0.0003(17) 0.0117(15) -0.0023(16) C7 0.0243(18) 0.0288(19) 0.0292(18) -0.0006(15) 0.0099(15) 0.0000(15) C8 0.030(2) 0.057(3) 0.036(2) 0.016(2) 0.0081(18) 0.004(2) C9 0.034(2) 0.107(4) 0.026(2) -0.002(3) 0.0098(19) -0.009(3) C10 0.108(6) 0.155(8) 0.075(5) 0.051(5) -0.050(5) -0.060(6) C11 0.127(6) 0.055(4) 0.058(4) -0.010(3) -0.013(4) -0.013(4) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl3 C3 1.723(4) . . yes O2 C2 1.220(5) . . yes O4 C4 1.336(5) . . yes O5 C5 1.237(5) . . yes O9 C9 1.396(8) . . yes O4 H4 0.8600 . . no O9 H9 0.8600 . . no N1 C2 1.378(5) . . yes N1 C7 1.370(5) . . yes N1 H1 0.8600 . . no C2 C3 1.462(6) . . no C3 C4 1.357(6) . . no C4 C5 1.495(5) . . no C5 C6 1.425(6) . . no C6 C7 1.353(6) . . no C7 C8 1.505(6) . . no C8 C9 1.547(7) . . no C9 C10 1.510(10) . . no C9 C11 1.482(9) . . no C6 H2 0.9500 . . no C8 H8A 0.9500 . . no C8 H8B 0.9500 . . no C10 H3 0.9400 . . no C10 H5 0.9400 . . no C10 H10A 0.9500 . . no C11 H6 0.9600 . . no C11 H7 0.9400 . . no C11 H11A 0.9500 . . 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O4 H4 120.00 . . . no C9 O9 H9 115.00 . . . no C2 N1 C7 135.2(4) . . . yes C2 N1 H1 112.00 . . . no C7 N1 H1 112.00 . . . no O2 C2 N1 117.5(4) . . . yes O2 C2 C3 120.1(3) . . . yes N1 C2 C3 122.4(4) . . . yes Cl3 C3 C2 112.7(3) . . . yes C2 C3 C4 130.7(3) . . . no Cl3 C3 C4 116.7(3) . . . yes O4 C4 C3 117.6(3) . . . yes O4 C4 C5 113.2(4) . . . yes C3 C4 C5 129.2(4) . . . no C4 C5 C6 123.5(4) . . . no O5 C5 C4 115.4(3) . . . yes O5 C5 C6 121.0(3) . . . yes C5 C6 C7 131.7(4) . . . no N1 C7 C8 112.4(4) . . . yes C6 C7 C8 120.6(3) . . . no N1 C7 C6 126.9(3) . . . yes C7 C8 C9 115.4(4) . . . no C8 C9 C11 113.1(4) . . . no C10 C9 C11 110.5(6) . . . no C8 C9 C10 107.6(5) . . . no O9 C9 C8 107.3(5) . . . yes O9 C9 C10 106.3(5) . . . yes O9 C9 C11 111.7(6) . . . yes C5 C6 H2 114.00 . . . no C7 C6 H2 114.00 . . . no C7 C8 H8A 108.00 . . . no C7 C8 H8B 108.00 . . . no C9 C8 H8A 108.00 . . . no C9 C8 H8B 108.00 . . . no H8A C8 H8B 109.00 . . . no C9 C10 H3 109.00 . . . no C9 C10 H5 109.00 . . . no C9 C10 H10A 109.00 . . . no H3 C10 H5 110.00 . . . no H3 C10 H10A 110.00 . . . no H5 C10 H10A 110.00 . . . no C9 C11 H6 109.00 . . . no C9 C11 H7 110.00 . . . no C9 C11 H11A 110.00 . . . no H6 C11 H7 109.00 . . . no H6 C11 H11A 109.00 . . . no H7 C11 H11A 110.00 . . . 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 C7 N1 C2 O2 179.5(4) . . . . no C7 N1 C2 C3 1.0(7) . . . . no C2 N1 C7 C6 5.3(7) . . . . no C2 N1 C7 C8 -174.9(4) . . . . no O2 C2 C3 Cl3 -3.6(5) . . . . no O2 C2 C3 C4 175.6(4) . . . . no N1 C2 C3 Cl3 174.9(3) . . . . no N1 C2 C3 C4 -5.9(6) . . . . no Cl3 C3 C4 O4 1.8(4) . . . . no Cl3 C3 C4 C5 -178.3(3) . . . . no C2 C3 C4 O4 -177.4(3) . . . . no C2 C3 C4 C5 2.4(6) . . . . no O4 C4 C5 O5 1.3(5) . . . . no O4 C4 C5 C6 -176.9(3) . . . . no C3 C4 C5 O5 -178.6(4) . . . . no C3 C4 C5 C6 3.3(6) . . . . no O5 C5 C6 C7 -180.0(4) . . . . no C4 C5 C6 C7 -1.9(7) . . . . no C5 C6 C7 N1 -4.1(7) . . . . no C5 C6 C7 C8 176.2(4) . . . . no N1 C7 C8 C9 -100.3(4) . . . . no C6 C7 C8 C9 79.5(5) . . . . no C7 C8 C9 O9 -75.9(6) . . . . no C7 C8 C9 C10 170.0(5) . . . . no C7 C8 C9 C11 47.8(6) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cl3 O2 2.791(3) . . no Cl3 O4 2.773(3) . . no Cl3 O5 3.387(4) . 3_656 no Cl3 C5 3.438(4) . 3_656 no Cl3 C6 3.629(4) . 3_656 no Cl3 C6 3.578(4) . 3_666 no Cl3 C10 3.465(8) . 4_556 no Cl3 H3 2.8300 . 4_556 no O2 Cl3 2.791(3) . . no O2 N1 3.172(5) . 2_546 no O2 O4 2.663(4) . 4_455 no O2 O5 3.104(4) . 4_455 no O4 C6 3.410(5) . 3_666 no O4 Cl3 2.773(3) . . no O4 O5 2.555(3) . . no O4 O2 2.663(4) . 4_555 no O4 C7 3.260(5) . 3_666 no O5 O2 3.104(4) . 4_555 no O5 O4 2.555(3) . . no O5 C3 3.412(5) . 3_656 no O5 C3 3.414(5) . 3_666 no O5 Cl3 3.387(4) . 3_656 no O5 N1 2.922(4) . 4_555 no O9 C6 3.232(7) . . no O2 H4 1.8700 . 4_455 no O4 H7 2.6500 . 3_656 no O5 H4 2.1900 . . no O5 H1 2.0900 . 4_555 no O5 H6 2.7900 . 4_555 no O9 H2 2.7300 . . no O9 H9 2.7500 . 2_555 no O9 H10A 2.9200 . 2_545 no N1 C11 3.314(7) . . no N1 O2 3.172(5) . 2_556 no N1 O5 2.922(4) . 4_455 no C3 C4 3.388(5) . 3_656 no C3 O5 3.412(5) . 3_656 no C3 O5 3.414(5) . 3_666 no C3 C6 3.589(5) . 3_666 no C3 C5 3.321(5) . 3_656 no C3 C5 3.316(5) . 3_666 no C4 C3 3.388(5) . 3_656 no C4 C5 3.549(5) . 3_656 no C4 C4 3.238(5) . 3_656 no C4 C4 3.494(5) . 3_666 no C4 C5 3.411(5) . 3_666 no C4 C6 3.518(5) . 3_666 no C5 C3 3.316(5) . 3_666 no C5 Cl3 3.438(4) . 3_656 no C5 C3 3.321(5) . 3_656 no C5 C4 3.549(5) . 3_656 no C5 C4 3.411(5) . 3_666 no C6 C3 3.589(5) . 3_666 no C6 O9 3.232(7) . . no C6 Cl3 3.629(4) . 3_656 no C6 Cl3 3.578(4) . 3_666 no C6 O4 3.410(5) . 3_666 no C6 C4 3.518(5) . 3_666 no C7 O4 3.260(5) . 3_666 no C10 Cl3 3.465(8) . 4_454 no C11 N1 3.314(7) . . no C2 H4 2.8800 . 4_455 no C7 H6 3.0800 . . no C7 H7 2.7400 . . no C10 H9 2.9800 . 2_555 no H1 H8A 2.0300 . . no H1 O5 2.0900 . 4_455 no H2 O9 2.7300 . . no H2 H8B 2.4100 . . no H3 H11A 2.5100 . . no H3 Cl3 2.8300 . 4_454 no H4 O5 2.1900 . . no H4 O2 1.8700 . 4_555 no H4 C2 2.8800 . 4_555 no H5 H6 2.4600 . . no H5 H8A 2.5100 . . no H6 C7 3.0800 . . no H6 H5 2.4600 . . no H6 H8A 2.5900 . . no H6 O5 2.7900 . 4_455 no H7 C7 2.7400 . . no H7 H9 2.4000 . . no H7 O4 2.6500 . 3_656 no H8A H1 2.0300 . . no H8A H5 2.5100 . . no H8A H6 2.5900 . . no H8A H10A 2.5800 . . no H8B H2 2.4100 . . no H8B H10A 2.4000 . . no H8B H9 2.5600 . 2_555 no H9 H7 2.4000 . . no H9 H11A 2.4400 . . no H9 O9 2.7500 . 2_545 no H9 C10 2.9800 . 2_545 no H9 H8B 2.5600 . 2_545 no H9 H10A 2.2700 . 2_545 no H10A H8A 2.5800 . . no H10A H8B 2.4000 . . no H10A O9 2.9200 . 2_555 no H10A H9 2.2700 . 2_555 no H11A H3 2.5100 . . no H11A H9 2.4400 . . 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N1 H1 O5 0.8600 2.0900 2.922(4) 164.00 4_455 yes O4 H4 O2 0.8600 1.8700 2.663(4) 152.00 4_555 yes C10 H3 Cl3 0.9400 2.8300 3.465(8) 126.00 4_454 yes #===END