data_sarpong12 _audit_creation_method SHELXL-97 _chemical_name_systematic ; sarpong12 ; _chemical_name_common VM-iodolactone _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 I N O3' _chemical_formula_weight 399.21 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' 'I' 'I' -0.3257 6.8362 '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)/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 9.6608(9) _cell_length_b 7.7675(7) _cell_length_c 20.3906(19) _cell_angle_alpha 90.00 _cell_angle_beta 91.435(3) _cell_angle_gamma 90.00 _cell_volume 1529.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9871 _cell_measurement_theta_min 4.34 _cell_measurement_theta_max 67.78 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.734 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 16.536 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2416 _exptl_absorpt_correction_T_max 0.2886 _exptl_absorpt_process_details SADABS _diffrn_refln_scan_width 1.0 _diffrn_refln_scan_rate 5 _space_group.centring_type primitive _space_group.IT_number 14 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'microfocus rotating anode' _diffrn_radiation_monochromator 'HELIOS multilayer mirrors' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_reflns_number 19318 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0138 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.34 _diffrn_reflns_theta_max 68.18 _reflns_number_total 2781 _reflns_number_gt 2758 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR-2004' _computing_structure_refinement 'SHELXL-97' _computing_molecular_graphics 'ORTEP-32' _computing_publication_material 'WinGX' _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^)+(0.0281P)^2^+1.8869P] 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 2781 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0199 _refine_ls_R_factor_gt 0.0196 _refine_ls_wR_factor_ref 0.0510 _refine_ls_wR_factor_gt 0.0509 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _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 C1 C 0.1046(2) 0.1454(3) 0.62150(11) 0.0123(4) Uani 1 1 d . . . C2 C 0.1295(3) -0.0034(3) 0.57628(12) 0.0145(5) Uani 1 1 d . . . H2A H 0.1874 0.0316 0.5392 0.017 Uiso 1 1 calc R . . H2B H 0.0410 -0.0511 0.5587 0.017 Uiso 1 1 calc R . . C3 C 0.2059(2) -0.1355(3) 0.62067(11) 0.0127(5) Uani 1 1 d . . . H3 H 0.1342 -0.2114 0.6402 0.015 Uiso 1 1 calc R . . C4 C 0.3069(2) -0.2510(3) 0.58511(11) 0.0133(4) Uani 1 1 d . . . H4A H 0.2603 -0.2974 0.5451 0.016 Uiso 1 1 calc R . . H4B H 0.3317 -0.3496 0.6138 0.016 Uiso 1 1 calc R . . C5 C 0.4410(2) -0.1584(3) 0.56539(10) 0.0115(4) Uani 1 1 d . . . H5 H 0.4156 -0.0551 0.5384 0.014 Uiso 1 1 calc R . . C6 C 0.5125(2) -0.0980(3) 0.62910(10) 0.0107(4) Uani 1 1 d . . . H6 H 0.5281 -0.2003 0.6581 0.013 Uiso 1 1 calc R . . C7 C 0.4245(2) 0.0318(3) 0.66527(11) 0.0102(4) Uani 1 1 d . . . H7 H 0.4222 0.1431 0.6406 0.012 Uiso 1 1 calc R . . C8 C 0.2737(2) -0.0289(3) 0.67746(11) 0.0112(5) Uani 1 1 d . . . C9 C 0.1816(2) 0.1293(3) 0.67953(11) 0.0120(4) Uani 1 1 d . . . C10 C 0.1733(2) 0.2599(3) 0.72611(11) 0.0143(5) Uani 1 1 d . . . H10 H 0.2241 0.2532 0.7665 0.017 Uiso 1 1 calc R . . C11 C 0.0894(2) 0.3992(3) 0.71201(11) 0.0155(5) Uani 1 1 d . . . H11 H 0.0805 0.4906 0.7425 0.019 Uiso 1 1 calc R . . C12 C 0.0171(2) 0.4024(3) 0.65118(11) 0.0138(5) Uani 1 1 d . . . C13 C 0.5287(2) -0.2787(3) 0.52439(11) 0.0149(5) Uani 1 1 d . . . H13A H 0.6132 -0.2190 0.5116 0.022 Uiso 1 1 calc R . . H13B H 0.4758 -0.3135 0.4849 0.022 Uiso 1 1 calc R . . H13C H 0.5535 -0.3810 0.5503 0.022 Uiso 1 1 calc R . . C14 C 0.2921(2) -0.1235(3) 0.74282(11) 0.0133(4) Uani 1 1 d . . . H14A H 0.2081 -0.1128 0.7693 0.016 Uiso 1 1 calc R . . H14B H 0.3119 -0.2470 0.7357 0.016 Uiso 1 1 calc R . . C15 C 0.4134(3) -0.0349(3) 0.77589(12) 0.0131(5) Uani 1 1 d . . . C16 C -0.1373(3) 0.5483(4) 0.57771(14) 0.0258(6) Uani 1 1 d . . . H16A H -0.0716 0.5439 0.5419 0.039 Uiso 1 1 calc R . . H16B H -0.1909 0.6553 0.5746 0.039 Uiso 1 1 calc R . . H16C H -0.2003 0.4496 0.5744 0.039 Uiso 1 1 calc R . . N1 N 0.0219(2) 0.2792(3) 0.60635(9) 0.0139(4) Uani 1 1 d . . . O1 O 0.48307(17) 0.0604(2) 0.73083(8) 0.0134(3) Uani 1 1 d . . . O2 O 0.4510(2) -0.0359(2) 0.83247(9) 0.0194(4) Uani 1 1 d . . . O3 O -0.06283(19) 0.5428(2) 0.63959(9) 0.0189(4) Uani 1 1 d . . . I1 I 0.712457(13) 0.026585(18) 0.613543(6) 0.01166(7) 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 C1 0.0069(10) 0.0164(11) 0.0136(10) -0.0001(9) -0.0012(8) 0.0000(9) C2 0.0112(12) 0.0181(11) 0.0138(12) -0.0028(9) -0.0061(9) 0.0026(9) C3 0.0104(11) 0.0137(11) 0.0136(10) -0.0011(9) -0.0050(8) -0.0020(8) C4 0.0134(11) 0.0107(10) 0.0155(10) -0.0027(9) -0.0071(9) 0.0000(9) C5 0.0135(11) 0.0103(10) 0.0103(10) -0.0016(8) -0.0053(8) 0.0024(9) C6 0.0090(10) 0.0112(11) 0.0118(10) -0.0001(8) -0.0030(8) -0.0005(9) C7 0.0103(11) 0.0122(11) 0.0080(10) -0.0014(8) -0.0049(8) -0.0004(8) C8 0.0101(11) 0.0132(11) 0.0102(11) -0.0009(8) -0.0032(9) -0.0005(9) C9 0.0083(10) 0.0144(11) 0.0132(10) 0.0010(9) -0.0009(8) -0.0008(9) C10 0.0119(11) 0.0187(12) 0.0122(10) -0.0006(9) -0.0023(8) 0.0001(9) C11 0.0142(11) 0.0157(12) 0.0166(11) -0.0042(9) -0.0015(9) 0.0009(9) C12 0.0091(10) 0.0149(11) 0.0173(11) 0.0020(9) 0.0002(8) 0.0034(9) C13 0.0166(11) 0.0135(11) 0.0143(11) -0.0031(9) -0.0052(9) 0.0047(9) C14 0.0138(11) 0.0137(11) 0.0122(10) 0.0021(9) -0.0024(8) -0.0009(9) C15 0.0140(12) 0.0121(11) 0.0131(12) -0.0007(8) -0.0014(9) 0.0027(9) C16 0.0272(15) 0.0254(14) 0.0241(14) 0.0005(11) -0.0103(11) 0.0131(11) N1 0.0105(9) 0.0176(10) 0.0135(9) -0.0007(8) -0.0015(7) 0.0016(8) O1 0.0136(8) 0.0166(8) 0.0098(7) -0.0025(6) -0.0042(6) -0.0023(7) O2 0.0245(10) 0.0223(10) 0.0112(8) -0.0006(6) -0.0061(7) -0.0017(7) O3 0.0164(9) 0.0191(9) 0.0209(9) -0.0009(7) -0.0045(7) 0.0065(7) I1 0.00896(9) 0.01464(10) 0.01123(9) -0.00109(5) -0.00251(6) 0.00062(5) _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 C1 N1 1.343(3) . ? C1 C9 1.388(3) . ? C1 C2 1.502(3) . ? C2 C3 1.544(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.523(3) . ? C3 C8 1.555(3) . ? C3 H3 1.0000 . ? C4 C5 1.544(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C13 1.525(3) . ? C5 C6 1.530(3) . ? C5 H5 1.0000 . ? C6 C7 1.522(3) . ? C6 I1 2.190(2) . ? C6 H6 1.0000 . ? C7 O1 1.456(3) . ? C7 C8 1.556(3) . ? C7 H7 1.0000 . ? C8 C9 1.518(3) . ? C8 C14 1.528(3) . ? C9 C10 1.394(3) . ? C10 C11 1.377(3) . ? C10 H10 0.9500 . ? C11 C12 1.408(3) . ? C11 H11 0.9500 . ? C12 N1 1.325(3) . ? C12 O3 1.353(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.504(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 O2 1.201(3) . ? C15 O1 1.370(3) . ? C16 O3 1.437(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 N1 C1 C9 124.7(2) . . ? N1 C1 C2 123.9(2) . . ? C9 C1 C2 111.3(2) . . ? C1 C2 C3 103.45(19) . . ? C1 C2 H2A 111.1 . . ? C3 C2 H2A 111.1 . . ? C1 C2 H2B 111.1 . . ? C3 C2 H2B 111.1 . . ? H2A C2 H2B 109.0 . . ? C4 C3 C2 114.52(19) . . ? C4 C3 C8 113.88(18) . . ? C2 C3 C8 105.64(19) . . ? C4 C3 H3 107.5 . . ? C2 C3 H3 107.5 . . ? C8 C3 H3 107.5 . . ? C3 C4 C5 113.66(19) . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4B 108.8 . . ? C5 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C13 C5 C6 114.08(18) . . ? C13 C5 C4 109.77(18) . . ? C6 C5 C4 106.61(17) . . ? C13 C5 H5 108.8 . . ? C6 C5 H5 108.8 . . ? C4 C5 H5 108.8 . . ? C7 C6 C5 111.63(18) . . ? C7 C6 I1 106.46(14) . . ? C5 C6 I1 113.19(14) . . ? C7 C6 H6 108.5 . . ? C5 C6 H6 108.5 . . ? I1 C6 H6 108.5 . . ? O1 C7 C6 109.68(17) . . ? O1 C7 C8 104.09(17) . . ? C6 C7 C8 114.42(18) . . ? O1 C7 H7 109.5 . . ? C6 C7 H7 109.5 . . ? C8 C7 H7 109.5 . . ? C9 C8 C14 114.84(19) . . ? C9 C8 C3 102.41(18) . . ? C14 C8 C3 115.53(19) . . ? C9 C8 C7 108.10(18) . . ? C14 C8 C7 101.33(18) . . ? C3 C8 C7 114.90(19) . . ? C1 C9 C10 118.5(2) . . ? C1 C9 C8 110.6(2) . . ? C10 C9 C8 130.7(2) . . ? C11 C10 C9 118.3(2) . . ? C11 C10 H10 120.9 . . ? C9 C10 H10 120.9 . . ? C10 C11 C12 118.3(2) . . ? C10 C11 H11 120.8 . . ? C12 C11 H11 120.8 . . ? N1 C12 O3 119.4(2) . . ? N1 C12 C11 124.7(2) . . ? O3 C12 C11 115.9(2) . . ? C5 C13 H13A 109.5 . . ? C5 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C5 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C8 104.07(18) . . ? C15 C14 H14A 110.9 . . ? C8 C14 H14A 110.9 . . ? C15 C14 H14B 110.9 . . ? C8 C14 H14B 110.9 . . ? H14A C14 H14B 109.0 . . ? O2 C15 O1 120.4(2) . . ? O2 C15 C14 129.9(2) . . ? O1 C15 C14 109.68(19) . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 N1 C1 115.6(2) . . ? C15 O1 C7 110.33(17) . . ? C12 O3 C16 116.64(19) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.865 _refine_diff_density_min -0.547 _refine_diff_density_rms 0.080