# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Peter Horton' _publ_contact_author_email P.N.Horton@soton.ac.uk loop_ _publ_author_name 'M. John Plater' 'Paul Barnes' 'Lauren K. McDonald' 'Sandy Wallace' 'Nia Archer' ; T.Gelbrich ; 'Peter N. Horton' 'Michael B. Hursthouse' data_2008src0603 _database_code_depnum_ccdc_archive 'CCDC 702015' #Dr. M. J. Plater _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H13 I N2 O' _chemical_formula_weight 292.11 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' I I -0.4742 1.8119 '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 8.5840(2) _cell_length_b 12.9688(3) _cell_length_c 10.3119(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.8520(10) _cell_angle_gamma 90.00 _cell_volume 1127.43(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2649 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description Block _exptl_crystal_colour 'Light Yellow' _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.721 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 2.808 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2928 _exptl_absorpt_correction_T_max 0.5522 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission: 0.5445 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12694 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2569 _reflns_number_gt 2409 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0143P)^2^+1.0800P] 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 2569 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0206 _refine_ls_R_factor_gt 0.0189 _refine_ls_wR_factor_ref 0.0430 _refine_ls_wR_factor_gt 0.0422 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 0.0237(3) 0.34544(17) 0.4044(2) 0.0281(5) Uani 1 1 d . . . H1A H -0.0388 0.3696 0.4687 0.042 Uiso 1 1 calc R . . H1B H -0.0475 0.3167 0.3273 0.042 Uiso 1 1 calc R . . H1C H 0.0831 0.4033 0.3766 0.042 Uiso 1 1 calc R . . C2 C 0.1376(2) 0.26360(16) 0.46641(19) 0.0197(4) Uani 1 1 d . . . C3 C 0.1859(2) 0.07851(16) 0.4905(2) 0.0220(4) Uani 1 1 d . . . H3A H 0.1144 0.0330 0.5296 0.026 Uiso 1 1 calc R . . H3B H 0.2693 0.1035 0.5635 0.026 Uiso 1 1 calc R . . C4 C 0.2636(2) 0.01547(15) 0.39781(19) 0.0178(4) Uani 1 1 d . . . C5 C 0.3343(2) -0.07783(16) 0.44211(19) 0.0210(4) Uani 1 1 d . . . H5 H 0.3291 -0.1019 0.5282 0.025 Uiso 1 1 calc R . . C6 C 0.4111(2) -0.13505(16) 0.36220(19) 0.0199(4) Uani 1 1 d . . . H6 H 0.4593 -0.1986 0.3931 0.024 Uiso 1 1 calc R . . C7 C 0.2712(2) 0.04712(16) 0.2705(2) 0.0199(4) Uani 1 1 d . . . H7 H 0.2222 0.1097 0.2367 0.024 Uiso 1 1 calc R . . C8 C 0.3501(2) -0.01254(16) 0.19361(19) 0.0208(4) Uani 1 1 d . . . H8 H 0.3560 0.0096 0.1068 0.025 Uiso 1 1 calc R . . C9 C 0.5085(3) -0.16279(17) 0.1578(2) 0.0259(4) Uani 1 1 d . . . H9A H 0.4509 -0.1637 0.0663 0.039 Uiso 1 1 calc R . . H9B H 0.5209 -0.2335 0.1917 0.039 Uiso 1 1 calc R . . H9C H 0.6134 -0.1318 0.1612 0.039 Uiso 1 1 calc R . . N1 N 0.0959(2) 0.16597(13) 0.43132(17) 0.0218(4) Uani 1 1 d . . . H1 H 0.0109 0.1552 0.3703 0.026 Uiso 1 1 calc R . . N2 N 0.4190(2) -0.10163(12) 0.23938(16) 0.0179(3) Uani 1 1 d . . . O1 O 0.26020(17) 0.28400(12) 0.54493(15) 0.0282(3) Uani 1 1 d . . . I1 I 0.746254(14) 0.102095(10) 0.193810(11) 0.01964(5) 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 0.0280(11) 0.0199(11) 0.0364(12) -0.0003(9) 0.0058(9) 0.0043(9) C2 0.0182(9) 0.0214(10) 0.0207(9) -0.0038(8) 0.0070(8) -0.0009(8) C3 0.0232(10) 0.0212(10) 0.0207(10) 0.0006(8) 0.0021(8) 0.0007(8) C4 0.0155(8) 0.0162(9) 0.0195(9) 0.0003(7) -0.0020(7) -0.0040(7) C5 0.0262(10) 0.0193(10) 0.0167(9) 0.0033(8) 0.0025(8) -0.0025(8) C6 0.0239(10) 0.0154(9) 0.0182(9) 0.0031(7) -0.0014(8) -0.0021(8) C7 0.0187(9) 0.0179(10) 0.0209(9) 0.0043(8) -0.0020(8) -0.0011(8) C8 0.0206(9) 0.0236(10) 0.0165(9) 0.0045(8) -0.0004(7) -0.0035(8) C9 0.0283(11) 0.0287(12) 0.0200(10) -0.0041(8) 0.0028(8) 0.0016(9) N1 0.0189(8) 0.0196(9) 0.0237(8) -0.0025(7) -0.0040(7) 0.0005(7) N2 0.0181(8) 0.0185(9) 0.0160(8) -0.0008(6) 0.0001(7) -0.0033(6) O1 0.0236(8) 0.0279(9) 0.0311(8) -0.0095(6) -0.0001(6) -0.0034(6) I1 0.02020(8) 0.02133(9) 0.01589(8) -0.00048(4) -0.00043(5) 0.00110(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 C2 1.502(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 O1 1.230(2) . ? C2 N1 1.347(3) . ? C3 N1 1.442(3) . ? C3 C4 1.506(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C7 1.389(3) . ? C4 C5 1.392(3) . ? C5 C6 1.368(3) . ? C5 H5 0.9500 . ? C6 N2 1.352(3) . ? C6 H6 0.9500 . ? C7 C8 1.374(3) . ? C7 H7 0.9500 . ? C8 N2 1.342(3) . ? C8 H8 0.9500 . ? C9 N2 1.473(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? N1 H1 0.8800 . ? 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 N1 122.04(19) . . ? O1 C2 C1 122.41(19) . . ? N1 C2 C1 115.54(18) . . ? N1 C3 C4 115.10(17) . . ? N1 C3 H3A 108.5 . . ? C4 C3 H3A 108.5 . . ? N1 C3 H3B 108.5 . . ? C4 C3 H3B 108.5 . . ? H3A C3 H3B 107.5 . . ? C7 C4 C5 118.16(18) . . ? C7 C4 C3 123.04(18) . . ? C5 C4 C3 118.78(17) . . ? C6 C5 C4 120.27(18) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? N2 C6 C5 120.34(18) . . ? N2 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C8 C7 C4 119.68(19) . . ? C8 C7 H7 120.2 . . ? C4 C7 H7 120.2 . . ? N2 C8 C7 120.93(18) . . ? N2 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C2 N1 C3 122.11(17) . . ? C2 N1 H1 118.9 . . ? C3 N1 H1 118.9 . . ? C8 N2 C6 120.60(17) . . ? C8 N2 C9 120.35(17) . . ? C6 N2 C9 119.03(17) . . ? 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 I1 0.88 2.72 3.5949(17) 173.9 1_455 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.334 _refine_diff_density_min -0.682 _refine_diff_density_rms 0.075 data_06src0496R _database_code_depnum_ccdc_archive 'CCDC 702097' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 I N O2' _chemical_formula_weight 331.14 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' I I -0.4742 1.8119 '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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.9338(2) _cell_length_b 14.4447(5) _cell_length_c 11.0343(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.597(2) _cell_angle_gamma 90.00 _cell_volume 1229.10(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2250 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.02 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.790 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 2.591 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6253 _exptl_absorpt_correction_T_max 0.6253 _exptl_absorpt_process_details ; Sheldrick, G. M. (2003). SADABS. Version 2.10. Bruker AXS Inc., Madison, Wisconsin, USA. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8224 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2333 _reflns_number_gt 2294 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0059P)^2^+3.1143P] 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 ? _refine_ls_number_reflns 2333 _refine_ls_number_parameters 151 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0242 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0573 _refine_ls_wR_factor_gt 0.0569 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 I1 I 0.22460(2) 0.114331(12) 0.485376(16) 0.02226(9) Uani 1 1 d . . . O1 O 0.4712(3) 0.26977(16) 0.3683(2) 0.0333(5) Uani 1 1 d D . . H1O H 0.411(4) 0.227(2) 0.394(3) 0.040 Uiso 1 1 d D . . O2 O 0.7534(2) 0.26132(14) 0.49349(17) 0.0222(4) Uani 1 1 d . . . N1 N 0.7294(3) 0.57560(16) 0.3419(2) 0.0203(5) Uani 1 1 d . . . C1 C 0.7858(3) 0.55497(19) 0.4685(2) 0.0175(5) Uani 1 1 d . . . C2 C 0.8898(4) 0.61829(19) 0.5496(3) 0.0221(6) Uani 1 1 d . . . H2 H 0.9226 0.6754 0.5191 0.026 Uiso 1 1 calc R . . C3 C 0.9436(4) 0.5963(2) 0.6742(3) 0.0244(6) Uani 1 1 d . . . H3 H 1.0146 0.6385 0.7297 0.029 Uiso 1 1 calc R . . C4 C 0.8949(4) 0.5124(2) 0.7204(3) 0.0236(6) Uani 1 1 d . . . H4 H 0.9313 0.4991 0.8069 0.028 Uiso 1 1 calc R . . C5 C 0.7955(4) 0.4497(2) 0.6419(2) 0.0210(6) Uani 1 1 d . . . H5 H 0.7642 0.3931 0.6744 0.025 Uiso 1 1 calc R . . C6 C 0.7386(3) 0.46835(19) 0.5124(2) 0.0175(5) Uani 1 1 d . . . C7 C 0.6384(3) 0.40505(19) 0.4257(2) 0.0192(5) Uani 1 1 d . . . C8 C 0.5899(4) 0.4296(2) 0.3023(3) 0.0234(6) Uani 1 1 d . . . H8 H 0.5242 0.3878 0.2432 0.028 Uiso 1 1 calc R . . C9 C 0.6365(4) 0.5153(2) 0.2634(3) 0.0240(6) Uani 1 1 d . . . H9 H 0.6004 0.5312 0.1776 0.029 Uiso 1 1 calc R . . C10 C 0.7736(5) 0.6654(2) 0.2936(3) 0.0299(7) Uani 1 1 d . . . H10D H 0.7114 0.6719 0.2061 0.045 Uiso 1 1 calc R . . H10E H 0.8988 0.6682 0.2999 0.045 Uiso 1 1 calc R . . H10F H 0.7400 0.7157 0.3426 0.045 Uiso 1 1 calc R . . C11 C 0.5944(3) 0.3093(2) 0.4659(2) 0.0206(5) Uani 1 1 d . . . H11 H 0.5472 0.3139 0.5421 0.025 Uiso 1 1 calc R . . C12 C 0.7417(4) 0.1719(2) 0.5470(3) 0.0316(7) Uani 1 1 d . . . H12A H 0.8489 0.1373 0.5500 0.047 Uiso 1 1 calc R . . H12B H 0.6432 0.1380 0.4959 0.047 Uiso 1 1 calc R . . H12C H 0.7250 0.1791 0.6317 0.047 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 I1 0.02024(12) 0.02223(12) 0.02441(12) -0.00379(6) 0.00541(8) -0.00355(6) O1 0.0297(12) 0.0353(13) 0.0339(12) 0.0018(10) 0.0057(10) -0.0066(10) O2 0.0183(10) 0.0213(10) 0.0283(10) 0.0049(8) 0.0079(8) -0.0003(8) N1 0.0242(12) 0.0196(12) 0.0191(11) 0.0027(9) 0.0089(9) 0.0054(9) C1 0.0156(13) 0.0218(13) 0.0172(12) 0.0027(10) 0.0078(10) 0.0062(10) C2 0.0226(15) 0.0195(14) 0.0255(14) -0.0004(10) 0.0085(12) 0.0021(11) C3 0.0229(15) 0.0259(15) 0.0238(13) -0.0065(11) 0.0043(11) 0.0012(12) C4 0.0249(14) 0.0287(15) 0.0176(12) 0.0003(11) 0.0057(11) 0.0034(12) C5 0.0226(14) 0.0242(14) 0.0178(12) 0.0031(10) 0.0080(11) 0.0029(11) C6 0.0144(12) 0.0201(13) 0.0192(12) 0.0005(10) 0.0064(10) 0.0046(10) C7 0.0143(13) 0.0234(13) 0.0206(13) -0.0015(11) 0.0055(10) 0.0019(11) C8 0.0212(14) 0.0284(15) 0.0189(13) -0.0003(11) 0.0013(11) -0.0004(11) C9 0.0252(15) 0.0278(15) 0.0176(12) 0.0025(11) 0.0022(11) 0.0071(12) C10 0.0429(19) 0.0208(14) 0.0277(14) 0.0076(12) 0.0120(13) 0.0039(13) C11 0.0166(13) 0.0249(14) 0.0209(13) 0.0002(11) 0.0055(10) -0.0004(11) C12 0.0247(15) 0.0315(17) 0.0370(17) 0.0160(13) 0.0040(13) 0.0004(13) _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 O1 C11 1.395(3) . ? O2 C11 1.409(3) . ? O2 C12 1.432(4) . ? N1 C9 1.324(4) . ? N1 C1 1.396(3) . ? N1 C10 1.475(4) . ? C1 C2 1.404(4) . ? C1 C6 1.423(4) . ? C2 C3 1.378(4) . ? C3 C4 1.403(4) . ? C4 C5 1.368(4) . ? C5 C6 1.419(4) . ? C6 C7 1.423(4) . ? C7 C8 1.372(4) . ? C7 C11 1.518(4) . ? C8 C9 1.389(4) . ? 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 C11 O2 C12 113.1(2) . . ? C9 N1 C1 120.9(2) . . ? C9 N1 C10 119.0(2) . . ? C1 N1 C10 120.1(2) . . ? N1 C1 C2 120.1(2) . . ? N1 C1 C6 118.7(2) . . ? C2 C1 C6 121.2(2) . . ? C3 C2 C1 118.9(3) . . ? C2 C3 C4 121.0(3) . . ? C5 C4 C3 120.6(3) . . ? C4 C5 C6 120.8(3) . . ? C5 C6 C7 123.4(3) . . ? C5 C6 C1 117.5(2) . . ? C7 C6 C1 119.1(2) . . ? C8 C7 C6 118.9(3) . . ? C8 C7 C11 119.7(2) . . ? C6 C7 C11 121.3(2) . . ? C7 C8 C9 120.3(3) . . ? N1 C9 C8 122.1(2) . . ? O1 C11 O2 113.2(2) . . ? O1 C11 C7 108.4(2) . . ? O2 C11 C7 104.8(2) . . ? 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 O1 H1O I1 0.865(19) 2.563(19) 3.424(2) 174(4) . _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 1.372 _refine_diff_density_min -0.597 _refine_diff_density_rms 0.077