# Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Wang, Mei-Xiang' 'Leng, Dong-Hui' 'Wang, De-Xian' 'Huang, Zhi-Tang' _publ_contact_author_name 'Wang, Mei-Xiang' _publ_contact_author_email mxwang@iccas.ac.cn _publ_section_title ; Highly efficient and enantioselective biotransformations of \"i \/c-lactam carbonitriles and carboxamides and their synthetic applications ; # Attachment '- betalactam.cif' data_m100106f _database_code_depnum_ccdc_archive 'CCDC 779903' #TrackingRef '- betalactam.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 Br N2 O2' _chemical_formula_weight 283.13 _chemical_absolute_configuration ad 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' Br Br -0.2901 2.4595 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 4.753(3) _cell_length_b 12.723(7) _cell_length_c 9.586(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.749(14) _cell_angle_gamma 90.00 _cell_volume 578.5(6) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 2213 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 27.9 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.626 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 3.540 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.2706 _exptl_absorpt_correction_T_max 0.8714 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type 'Rigaku Saturn CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 14.63 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5973 _diffrn_reflns_av_R_equivalents 0.1445 _diffrn_reflns_av_sigmaI/netI 0.1310 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2034 _reflns_number_gt 1557 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'CrystalStructure 3.8' _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^)+(0.0100P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.014(13) _refine_ls_number_reflns 2034 _refine_ls_number_parameters 153 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.0913 _refine_ls_wR_factor_gt 0.0898 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0.002 _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 Br1 Br 0.37391(11) -0.09482(5) -0.27033(5) 0.0463(2) Uani 1 1 d . . . O1 O 1.1193(6) -0.1157(4) 0.2598(3) 0.0285(11) Uani 1 1 d . . . O2 O 1.1433(6) 0.1814(3) 0.4560(4) 0.0272(9) Uani 1 1 d . . . N1 N 0.7180(8) 0.2238(4) 0.5287(4) 0.0218(10) Uani 1 1 d D . . N2 N 0.9211(7) 0.0524(3) 0.2458(4) 0.0178(9) Uani 1 1 d . . . C1 C 0.9740(10) -0.0448(5) 0.2990(5) 0.0200(11) Uani 1 1 d . . . C2 C 0.7856(9) -0.0264(4) 0.4185(5) 0.0220(11) Uani 1 1 d . . . H2A H 0.8850 -0.0289 0.5125 0.026 Uiso 1 1 calc R . . H2B H 0.6125 -0.0699 0.4142 0.026 Uiso 1 1 calc R . . C3 C 0.7431(9) 0.0869(4) 0.3575(5) 0.0181(11) Uani 1 1 d . . . H3 H 0.5442 0.1038 0.3248 0.022 Uiso 1 1 calc R . . C4 C 0.8859(9) 0.1702(4) 0.4518(5) 0.0179(11) Uani 1 1 d . . . C5 C 1.0170(9) 0.1057(4) 0.1236(5) 0.0204(11) Uani 1 1 d . . . H5A H 1.1809 0.0676 0.0899 0.024 Uiso 1 1 calc R . . H5B H 1.0794 0.1776 0.1501 0.024 Uiso 1 1 calc R . . C6 C 0.7877(9) 0.1121(4) 0.0071(5) 0.0200(11) Uani 1 1 d . . . C7 C 0.6586(10) 0.2071(5) -0.0299(5) 0.0267(12) Uani 1 1 d . . . H7 H 0.7196 0.2699 0.0165 0.032 Uiso 1 1 calc R . . C8 C 0.4441(10) 0.2110(5) -0.1327(5) 0.0311(13) Uani 1 1 d . . . H8 H 0.3588 0.2767 -0.1565 0.037 Uiso 1 1 calc R . . C9 C 0.3506(9) 0.1225(5) -0.2015(5) 0.0304(13) Uani 1 1 d . . . H9 H 0.1986 0.1253 -0.2709 0.036 Uiso 1 1 calc R . . C10 C 0.4855(10) 0.0276(4) -0.1667(5) 0.0254(12) Uani 1 1 d . . . C11 C 0.6993(9) 0.0220(4) -0.0636(5) 0.0220(12) Uani 1 1 d . . . H11 H 0.7863 -0.0436 -0.0410 0.026 Uiso 1 1 calc R . . H1A H 0.532(3) 0.213(4) 0.529(5) 0.038(16) Uiso 1 1 d D . . H1B H 0.789(6) 0.264(3) 0.599(3) 0.018(14) Uiso 1 1 d 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 Br1 0.0664(4) 0.0472(4) 0.0240(3) -0.0027(4) -0.0077(2) -0.0246(4) O1 0.0369(19) 0.020(3) 0.027(2) -0.0037(18) -0.0059(16) 0.0077(17) O2 0.0126(17) 0.039(2) 0.030(2) -0.0117(18) -0.0028(15) -0.0046(16) N1 0.015(2) 0.029(3) 0.021(3) -0.008(2) -0.0028(18) 0.001(2) N2 0.021(2) 0.021(2) 0.012(2) 0.0003(18) -0.0004(17) 0.0043(18) C1 0.018(3) 0.022(3) 0.019(3) 0.001(2) -0.008(2) -0.001(2) C2 0.022(2) 0.023(3) 0.020(3) 0.003(2) -0.003(2) -0.007(2) C3 0.015(2) 0.024(3) 0.015(3) -0.001(2) -0.001(2) 0.003(2) C4 0.017(3) 0.021(3) 0.015(3) 0.005(2) -0.006(2) 0.001(2) C5 0.021(2) 0.021(3) 0.019(3) 0.004(2) -0.001(2) 0.004(2) C6 0.020(2) 0.026(3) 0.015(3) 0.003(2) 0.005(2) -0.003(2) C7 0.032(3) 0.025(3) 0.023(3) 0.007(2) 0.002(2) 0.004(3) C8 0.034(3) 0.033(3) 0.025(3) 0.014(3) -0.001(2) 0.006(3) C9 0.023(3) 0.050(4) 0.017(3) 0.013(3) -0.008(2) -0.004(3) C10 0.028(3) 0.036(3) 0.012(3) 0.002(2) -0.002(2) -0.013(3) C11 0.026(2) 0.022(3) 0.018(3) 0.001(2) 0.000(2) 0.002(2) _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 Br1 C10 1.904(5) . ? O1 C1 1.210(7) . ? O2 C4 1.230(5) . ? N1 C4 1.312(6) . ? N1 H1A 0.894(10) . ? N1 H1B 0.895(10) . ? N2 C1 1.355(7) . ? N2 C5 1.452(6) . ? N2 C3 1.475(6) . ? C1 C2 1.518(7) . ? C2 C3 1.565(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.523(7) . ? C3 H3 1.0000 . ? C5 C6 1.511(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C11 1.383(7) . ? C6 C7 1.392(7) . ? C7 C8 1.372(7) . ? C7 H7 0.9500 . ? C8 C9 1.365(8) . ? C8 H8 0.9500 . ? C9 C10 1.396(7) . ? C9 H9 0.9500 . ? C10 C11 1.372(7) . ? C11 H11 0.9500 . ? 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 C4 N1 H1A 124(3) . . ? C4 N1 H1B 120(2) . . ? H1A N1 H1B 114.4(17) . . ? C1 N2 C5 132.0(4) . . ? C1 N2 C3 95.7(4) . . ? C5 N2 C3 132.2(4) . . ? O1 C1 N2 131.2(5) . . ? O1 C1 C2 136.5(5) . . ? N2 C1 C2 92.3(4) . . ? C1 C2 C3 85.9(4) . . ? C1 C2 H2A 114.3 . . ? C3 C2 H2A 114.3 . . ? C1 C2 H2B 114.3 . . ? C3 C2 H2B 114.3 . . ? H2A C2 H2B 111.5 . . ? N2 C3 C4 112.6(4) . . ? N2 C3 C2 86.0(3) . . ? C4 C3 C2 112.2(4) . . ? N2 C3 H3 114.3 . . ? C4 C3 H3 114.3 . . ? C2 C3 H3 114.3 . . ? O2 C4 N1 124.2(5) . . ? O2 C4 C3 120.3(4) . . ? N1 C4 C3 115.5(4) . . ? N2 C5 C6 111.8(4) . . ? N2 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? N2 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C11 C6 C7 118.7(5) . . ? C11 C6 C5 120.0(5) . . ? C7 C6 C5 121.3(5) . . ? C8 C7 C6 120.6(6) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C9 C8 C7 121.4(6) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C10 117.9(5) . . ? C8 C9 H9 121.1 . . ? C10 C9 H9 121.1 . . ? C11 C10 C9 121.6(5) . . ? C11 C10 Br1 120.0(4) . . ? C9 C10 Br1 118.3(4) . . ? C10 C11 C6 119.8(5) . . ? C10 C11 H11 120.1 . . ? C6 C11 H11 120.1 . . ? 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 C5 N2 C1 O1 0.5(9) . . . . ? C3 N2 C1 O1 -177.3(5) . . . . ? C5 N2 C1 C2 -179.4(5) . . . . ? C3 N2 C1 C2 2.8(4) . . . . ? O1 C1 C2 C3 177.5(6) . . . . ? N2 C1 C2 C3 -2.7(4) . . . . ? C1 N2 C3 C4 109.6(4) . . . . ? C5 N2 C3 C4 -68.1(6) . . . . ? C1 N2 C3 C2 -2.8(4) . . . . ? C5 N2 C3 C2 179.5(5) . . . . ? C1 C2 C3 N2 2.5(3) . . . . ? C1 C2 C3 C4 -110.3(4) . . . . ? N2 C3 C4 O2 -19.5(6) . . . . ? C2 C3 C4 O2 75.6(5) . . . . ? N2 C3 C4 N1 162.9(4) . . . . ? C2 C3 C4 N1 -102.1(5) . . . . ? C1 N2 C5 C6 105.6(6) . . . . ? C3 N2 C5 C6 -77.5(6) . . . . ? N2 C5 C6 C11 -69.7(6) . . . . ? N2 C5 C6 C7 109.3(5) . . . . ? C11 C6 C7 C8 1.3(7) . . . . ? C5 C6 C7 C8 -177.8(4) . . . . ? C6 C7 C8 C9 0.1(7) . . . . ? C7 C8 C9 C10 -1.7(7) . . . . ? C8 C9 C10 C11 2.1(7) . . . . ? C8 C9 C10 Br1 -175.9(4) . . . . ? C9 C10 C11 C6 -0.8(7) . . . . ? Br1 C10 C11 C6 177.2(3) . . . . ? C7 C6 C11 C10 -0.9(6) . . . . ? C5 C6 C11 C10 178.2(4) . . . . ? 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 H1A O2 0.894(10) 1.974(16) 2.826(5) 159(4) 1_455 N1 H1B O1 0.895(10) 2.069(16) 2.945(6) 166(4) 2_756 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.713 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.084 # Attachment '- fused betalactam.cif' data_sa633 _database_code_depnum_ccdc_archive 'CCDC 779904' #TrackingRef '- fused betalactam.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H10 I N O2' _chemical_formula_sum 'C7 H10 I N O2' _chemical_formula_weight 267.06 _chemical_absolute_configuration ad 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 6.634(3) _cell_length_b 9.052(3) _cell_length_c 14.778(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 887.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 483 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.999 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 3.562 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7171 _exptl_absorpt_correction_T_max 0.8420 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7896 _diffrn_reflns_av_R_equivalents 0.0608 _diffrn_reflns_av_sigmaI/netI 0.0505 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2022 _reflns_number_gt 1892 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (Sheldrick, 1997)' _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^)+(0.0358P)^2^+1.3949P] 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 0.04(6) _refine_ls_number_reflns 2022 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.0978 _refine_ls_wR_factor_gt 0.0948 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_restrained_S_all 1.144 _refine_ls_shift/su_max 0.000 _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 I1 I -0.15372(7) -0.09787(6) 0.54046(3) 0.03893(16) Uani 1 1 d . . . O1 O -0.1237(8) -0.1342(6) 0.8850(3) 0.0430(13) Uani 1 1 d . . . O2 O 0.3452(8) -0.0220(5) 0.7244(3) 0.0348(11) Uani 1 1 d . . . N1 N 0.1114(8) -0.2568(6) 0.7924(4) 0.0274(12) Uani 1 1 d . . . C1 C 0.0446(12) -0.1786(8) 0.8654(4) 0.0325(15) Uani 1 1 d . . . C2 C 0.2556(11) -0.1663(9) 0.9064(5) 0.0365(17) Uani 1 1 d . . . H2A H 0.2757 -0.2253 0.9621 0.044 Uiso 1 1 calc R . . H2B H 0.3045 -0.0637 0.9140 0.044 Uiso 1 1 calc R . . C3 C 0.3280(11) -0.2430(8) 0.8183(5) 0.0351(15) Uani 1 1 d . . . H3A H 0.3915 -0.3412 0.8305 0.042 Uiso 1 1 calc R . . C4 C 0.4501(11) -0.1516(8) 0.7541(6) 0.0388(18) Uani 1 1 d . . . H4A H 0.5771 -0.1217 0.7841 0.047 Uiso 1 1 calc R . . H4B H 0.4857 -0.2123 0.7007 0.047 Uiso 1 1 calc R . . C5 C 0.2258(10) -0.0386(8) 0.6447(5) 0.0304(15) Uani 1 1 d . . . H5A H 0.2987 -0.1022 0.6011 0.036 Uiso 1 1 calc R . . H5B H 0.2071 0.0594 0.6162 0.036 Uiso 1 1 calc R . . C6 C 0.0208(9) -0.1058(8) 0.6640(4) 0.0264(13) Uani 1 1 d . . . H6A H -0.0481 -0.0407 0.7091 0.032 Uiso 1 1 calc R . . C7 C 0.0224(10) -0.2612(7) 0.7025(4) 0.0272(14) Uani 1 1 d . . . H7A H -0.1170 -0.3000 0.7060 0.033 Uiso 1 1 calc R . . H7B H 0.1019 -0.3273 0.6628 0.033 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 0.0303(2) 0.0571(3) 0.0294(2) 0.0008(2) -0.00499(19) -0.0020(2) O1 0.034(3) 0.063(3) 0.033(3) -0.008(2) 0.009(2) 0.007(2) O2 0.026(2) 0.040(3) 0.038(3) 0.007(2) -0.009(2) -0.008(2) N1 0.023(3) 0.031(3) 0.028(3) -0.001(2) 0.002(2) 0.002(2) C1 0.033(4) 0.041(4) 0.024(3) 0.004(3) 0.005(3) -0.002(3) C2 0.032(4) 0.045(4) 0.033(4) 0.000(3) -0.005(3) 0.000(3) C3 0.027(3) 0.038(4) 0.040(4) 0.003(3) -0.004(3) 0.005(3) C4 0.026(4) 0.044(4) 0.046(4) 0.004(3) 0.001(4) 0.006(3) C5 0.019(3) 0.041(4) 0.031(4) -0.001(3) 0.001(3) -0.003(3) C6 0.019(3) 0.035(3) 0.026(3) 0.003(3) -0.005(2) -0.004(3) C7 0.028(3) 0.027(3) 0.027(3) -0.003(3) 0.001(3) -0.002(3) _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 I1 C6 2.163(6) . ? O1 C1 1.222(8) . ? O2 C5 1.427(8) . ? O2 C4 1.432(9) . ? N1 C1 1.364(8) . ? N1 C7 1.455(8) . ? N1 C3 1.492(9) . ? C1 C2 1.529(10) . ? C2 C3 1.552(10) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.498(10) . ? C3 H3A 1.0000 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.517(9) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.518(10) . ? C6 H6A 1.0000 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? 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 C5 O2 C4 115.9(6) . . ? C1 N1 C7 127.2(6) . . ? C1 N1 C3 93.8(6) . . ? C7 N1 C3 128.9(5) . . ? O1 C1 N1 131.0(7) . . ? O1 C1 C2 135.9(7) . . ? N1 C1 C2 93.1(6) . . ? C1 C2 C3 85.3(5) . . ? C1 C2 H2A 114.4 . . ? C3 C2 H2A 114.4 . . ? C1 C2 H2B 114.4 . . ? C3 C2 H2B 114.4 . . ? H2A C2 H2B 111.6 . . ? N1 C3 C4 113.9(6) . . ? N1 C3 C2 87.4(5) . . ? C4 C3 C2 116.9(6) . . ? N1 C3 H3A 112.2 . . ? C4 C3 H3A 112.2 . . ? C2 C3 H3A 112.2 . . ? O2 C4 C3 112.6(6) . . ? O2 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? O2 C4 H4B 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? O2 C5 C6 112.6(5) . . ? O2 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? O2 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? C5 C6 C7 115.8(6) . . ? C5 C6 I1 107.9(4) . . ? C7 C6 I1 110.5(4) . . ? C5 C6 H6A 107.4 . . ? C7 C6 H6A 107.4 . . ? I1 C6 H6A 107.4 . . ? N1 C7 C6 108.7(5) . . ? N1 C7 H7A 110.0 . . ? C6 C7 H7A 110.0 . . ? N1 C7 H7B 110.0 . . ? C6 C7 H7B 110.0 . . ? H7A C7 H7B 108.3 . . ? 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 C1 O1 25.9(12) . . . . ? C3 N1 C1 O1 173.0(8) . . . . ? C7 N1 C1 C2 -152.1(6) . . . . ? C3 N1 C1 C2 -4.9(6) . . . . ? O1 C1 C2 C3 -173.1(9) . . . . ? N1 C1 C2 C3 4.8(5) . . . . ? C1 N1 C3 C4 -113.4(6) . . . . ? C7 N1 C3 C4 32.9(9) . . . . ? C1 N1 C3 C2 4.9(6) . . . . ? C7 N1 C3 C2 151.2(6) . . . . ? C1 C2 C3 N1 -4.4(5) . . . . ? C1 C2 C3 C4 111.2(7) . . . . ? C5 O2 C4 C3 -89.9(7) . . . . ? N1 C3 C4 O2 41.4(9) . . . . ? C2 C3 C4 O2 -58.2(9) . . . . ? C4 O2 C5 C6 81.9(8) . . . . ? O2 C5 C6 C7 -62.5(8) . . . . ? O2 C5 C6 I1 173.0(5) . . . . ? C1 N1 C7 C6 59.7(8) . . . . ? C3 N1 C7 C6 -76.2(8) . . . . ? C5 C6 C7 N1 66.3(7) . . . . ? I1 C6 C7 N1 -170.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.603 _refine_diff_density_min -0.885 _refine_diff_density_rms 0.141