# 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_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Tim Snape' _publ_contact_author_email TJSNAPE@UCLAN.AC.UK _publ_section_title ; Towards a chemo-enzymatic method for the asymmetric synthesis of ?-amino tertiary alcohols ; loop_ _publ_author_name 'Tim Snape' 'Andrea March-Cortijos' # Attachment 'Compound_15.cif' data_s3151 _database_code_depnum_ccdc_archive 'CCDC 736703' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H17 N O4' _chemical_formula_weight 203.24 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 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 9.763(6) _cell_length_b 14.702(10) _cell_length_c 7.816(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.886(10) _cell_angle_gamma 90.00 _cell_volume 1061.5(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 187 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 14.51 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.099 _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 3837 _diffrn_reflns_av_R_equivalents 0.1552 _diffrn_reflns_av_sigmaI/netI 0.2038 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 21.96 _reflns_number_total 1297 _reflns_number_gt 732 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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. Because the crystal was weakly diffracting, it was necessary to use rigid bond and similarity restraints on the anisotropic atomic displacement parameters to avoid them becoming unrealistic, leading to the application of a total of 108 restraints. ; _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^)+(0.0054P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1297 _refine_ls_number_parameters 130 _refine_ls_number_restraints 108 _refine_ls_R_factor_all 0.2039 _refine_ls_R_factor_gt 0.1069 _refine_ls_wR_factor_ref 0.1379 _refine_ls_wR_factor_gt 0.1130 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.055 _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 O1 O 0.1149(4) 0.1657(3) 0.6583(6) 0.0202(13) Uani 1 1 d U . . H1 H 0.1580 0.1763 0.5832 0.030 Uiso 1 1 calc R . . O2 O 0.2552(5) 0.3008(3) 0.9218(5) 0.0193(13) Uani 1 1 d U . . H2 H 0.2451 0.3332 0.8299 0.029 Uiso 1 1 calc R . . O3 O 0.2068(5) 0.0943(3) 1.1250(6) 0.0261(14) Uani 1 1 d U . . H3 H 0.2334 0.0399 1.1251 0.039 Uiso 1 1 calc R . . O4 O 0.2669(6) -0.0732(3) 1.0300(7) 0.0375(16) Uani 1 1 d U . . N1 N 0.2294(6) -0.0258(4) 0.7449(8) 0.0215(16) Uani 1 1 d U . . C1 C 0.3077(7) 0.0583(5) 0.8064(9) 0.0252(19) Uani 1 1 d U . . H1A H 0.3584 0.0750 0.7198 0.030 Uiso 1 1 calc R . . H1B H 0.3828 0.0465 0.9244 0.030 Uiso 1 1 calc R . . C2 C 0.2185(7) 0.1396(5) 0.8280(10) 0.0153(17) Uani 1 1 d U . . C3 C 0.3225(7) 0.2166(5) 0.9030(9) 0.0201(19) Uani 1 1 d U . . H3A H 0.3891 0.1984 1.0231 0.024 Uiso 1 1 calc R . . H3B H 0.3814 0.2264 0.8226 0.024 Uiso 1 1 calc R . . C4 C 0.1230(7) 0.1199(4) 0.9465(9) 0.0198(19) Uani 1 1 d U . . H4A H 0.0659 0.1749 0.9517 0.024 Uiso 1 1 calc R . . H4B H 0.0543 0.0704 0.8908 0.024 Uiso 1 1 calc R . . C5 C 0.2185(8) -0.0884(5) 0.8670(10) 0.023(2) Uani 1 1 d U . . C6 C 0.1563(8) -0.1799(4) 0.7979(9) 0.033(2) Uani 1 1 d U . . H6A H 0.1802 -0.2234 0.8982 0.049 Uiso 1 1 calc R . . H6B H 0.1973 -0.2010 0.7058 0.049 Uiso 1 1 calc R . . H6C H 0.0509 -0.1750 0.7446 0.049 Uiso 1 1 calc R . . C7 C 0.1789(7) -0.0425(5) 0.5475(9) 0.0223(19) Uani 1 1 d U . . H7A H 0.1446 0.0157 0.4841 0.027 Uiso 1 1 calc R . . H7B H 0.0955 -0.0847 0.5174 0.027 Uiso 1 1 calc R . . C8 C 0.2926(8) -0.0815(4) 0.4796(10) 0.0167(19) Uani 1 1 d U . . H8 H 0.2647 -0.0936 0.3536 0.020 Uiso 1 1 calc R . . C9 C 0.4257(8) -0.1007(5) 0.5740(9) 0.031(2) Uani 1 1 d U . . H9A H 0.4594 -0.0899 0.7006 0.037 Uiso 1 1 calc R . . H9B H 0.4893 -0.1255 0.5163 0.037 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 O1 0.018(3) 0.028(3) 0.016(3) -0.001(3) 0.007(2) 0.001(2) O2 0.039(4) 0.010(3) 0.010(3) 0.006(3) 0.010(3) 0.000(3) O3 0.044(4) 0.020(4) 0.011(3) 0.002(3) 0.004(3) 0.000(3) O4 0.067(5) 0.026(4) 0.015(3) -0.003(3) 0.007(3) -0.002(3) N1 0.030(5) 0.023(4) 0.016(3) -0.003(3) 0.012(3) -0.010(3) C1 0.034(6) 0.022(4) 0.020(5) 0.006(4) 0.010(4) -0.001(3) C2 0.003(5) 0.027(4) 0.015(4) -0.003(4) 0.002(3) -0.004(3) C3 0.024(5) 0.023(4) 0.012(5) -0.002(4) 0.005(4) -0.002(3) C4 0.019(5) 0.014(5) 0.022(4) 0.002(4) -0.001(4) 0.004(3) C5 0.026(6) 0.016(5) 0.025(4) 0.004(4) 0.007(4) -0.001(4) C6 0.054(7) 0.023(5) 0.025(5) 0.001(4) 0.017(4) -0.005(4) C7 0.024(5) 0.023(5) 0.013(4) 0.003(4) -0.004(4) 0.009(4) C8 0.024(5) 0.011(5) 0.017(5) -0.006(4) 0.008(4) -0.004(4) C9 0.038(6) 0.035(6) 0.023(5) 0.000(4) 0.015(4) 0.012(4) _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 C2 1.435(7) . ? O1 H1 0.8400 . ? O2 C3 1.431(7) . ? O2 H2 0.8400 . ? O3 C4 1.421(7) . ? O3 H3 0.8400 . ? O4 C5 1.227(8) . ? N1 C5 1.355(8) . ? N1 C1 1.451(8) . ? N1 C7 1.480(8) . ? C1 C2 1.521(9) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.507(9) . ? C2 C4 1.540(9) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.503(9) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.492(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.301(8) . ? C8 H8 0.9500 . ? C9 H9A 0.9500 . ? C9 H9B 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 C2 O1 H1 109.5 . . ? C3 O2 H2 109.5 . . ? C4 O3 H3 109.5 . . ? C5 N1 C1 119.9(6) . . ? C5 N1 C7 123.1(6) . . ? C1 N1 C7 116.7(6) . . ? N1 C1 C2 116.6(6) . . ? N1 C1 H1A 108.2 . . ? C2 C1 H1A 108.2 . . ? N1 C1 H1B 108.2 . . ? C2 C1 H1B 108.2 . . ? H1A C1 H1B 107.3 . . ? O1 C2 C3 110.1(6) . . ? O1 C2 C1 111.4(6) . . ? C3 C2 C1 107.2(6) . . ? O1 C2 C4 102.9(6) . . ? C3 C2 C4 111.7(6) . . ? C1 C2 C4 113.5(6) . . ? O2 C3 C2 114.6(6) . . ? O2 C3 H3A 108.6 . . ? C2 C3 H3A 108.6 . . ? O2 C3 H3B 108.6 . . ? C2 C3 H3B 108.6 . . ? H3A C3 H3B 107.6 . . ? O3 C4 C2 111.8(6) . . ? O3 C4 H4A 109.2 . . ? C2 C4 H4A 109.2 . . ? O3 C4 H4B 109.2 . . ? C2 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? O4 C5 N1 121.1(7) . . ? O4 C5 C6 120.7(7) . . ? N1 C5 C6 118.0(7) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C7 C8 113.5(6) . . ? N1 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? N1 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C9 C8 C7 127.1(7) . . ? C9 C8 H8 116.4 . . ? C7 C8 H8 116.4 . . ? C8 C9 H9A 120.0 . . ? C8 C9 H9B 120.0 . . ? H9A C9 H9B 120.0 . . ? 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 O3 H3 O4 0.84 1.89 2.691(7) 158.1 . O2 H2 O3 0.84 1.86 2.697(6) 175.3 4_565 O1 H1 O2 0.84 1.84 2.679(6) 179.0 4_565 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 21.96 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.236 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.060 # Attachment 'Compound_13.cif' data_s3170 _database_code_depnum_ccdc_archive 'CCDC 736704' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H15 N O4' _chemical_formula_weight 201.22 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 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 9.2759(13) _cell_length_b 14.318(2) _cell_length_c 7.9435(11) _cell_angle_alpha 90.00 _cell_angle_beta 110.024(3) _cell_angle_gamma 90.00 _cell_volume 991.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 882 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 21.06 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.106 _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 5675 _diffrn_reflns_av_R_equivalents 0.0588 _diffrn_reflns_av_sigmaI/netI 0.0886 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 26.44 _reflns_number_total 2032 _reflns_number_gt 1344 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0203P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2032 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.0787 _refine_ls_wR_factor_gt 0.0718 _refine_ls_goodness_of_fit_ref 0.881 _refine_ls_restrained_S_all 0.881 _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 O1 O 0.79347(14) 0.40739(9) 0.45959(17) 0.0198(3) Uani 1 1 d . . . H1 H 0.7568 0.4611 0.4309 0.030 Uiso 1 1 calc R . . O2 O 0.87627(13) 0.33065(9) 0.06654(16) 0.0165(3) Uani 1 1 d . . . H2 H 0.8288 0.3255 -0.0440 0.025 Uiso 1 1 calc R . . O3 O 0.72596(14) 0.19336(8) 0.21124(16) 0.0182(3) Uani 1 1 d . . . H3 H 0.7548 0.1675 0.1333 0.027 Uiso 1 1 calc R . . O4 O 0.72868(15) 0.58292(9) 0.30757(18) 0.0248(4) Uani 1 1 d . . . N1 N 0.76339(16) 0.52762(10) 0.0581(2) 0.0146(4) Uani 1 1 d . . . C1 C 0.8769(2) 0.38019(13) 0.3454(2) 0.0163(4) Uani 1 1 d . . . H1A H 0.9390 0.3241 0.3963 0.020 Uiso 1 1 calc R . . H1B H 0.9482 0.4310 0.3422 0.020 Uiso 1 1 calc R . . C2 C 0.77196(19) 0.35871(12) 0.1542(2) 0.0137(4) Uani 1 1 d . . . C3 C 0.6570(2) 0.28106(12) 0.1453(2) 0.0164(4) Uani 1 1 d . . . H3A H 0.5921 0.3003 0.2155 0.020 Uiso 1 1 calc R . . H3B H 0.5892 0.2732 0.0192 0.020 Uiso 1 1 calc R . . C4 C 0.67616(19) 0.44310(12) 0.0618(2) 0.0146(4) Uani 1 1 d . . . H4A H 0.6160 0.4256 -0.0632 0.018 Uiso 1 1 calc R . . H4B H 0.6024 0.4577 0.1233 0.018 Uiso 1 1 calc R . . C5 C 0.8108(2) 0.54074(13) -0.0986(2) 0.0169(4) Uani 1 1 d . . . H5A H 0.8535 0.4813 -0.1244 0.020 Uiso 1 1 calc R . . H5B H 0.8934 0.5881 -0.0696 0.020 Uiso 1 1 calc R . . C6 C 0.6854(2) 0.57055(12) -0.2600(3) 0.0169(4) Uani 1 1 d . . . C7 C 0.5881(2) 0.59290(13) -0.3922(3) 0.0202(5) Uani 1 1 d . . . H7 H 0.5092 0.6110 -0.4995 0.024 Uiso 1 1 calc R . . C8 C 0.7729(2) 0.59654(13) 0.1795(3) 0.0185(5) Uani 1 1 d . . . C9 C 0.8387(2) 0.68900(13) 0.1550(3) 0.0244(5) Uani 1 1 d . . . H9A H 0.7853 0.7119 0.0333 0.037 Uiso 1 1 calc R . . H9B H 0.9482 0.6817 0.1738 0.037 Uiso 1 1 calc R . . H9C H 0.8258 0.7338 0.2420 0.037 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 O1 0.0308(8) 0.0164(8) 0.0164(8) 0.0016(6) 0.0132(6) 0.0044(7) O2 0.0188(7) 0.0205(8) 0.0119(7) 0.0001(6) 0.0074(6) 0.0030(6) O3 0.0288(8) 0.0142(7) 0.0139(7) -0.0003(6) 0.0101(6) 0.0016(6) O4 0.0421(9) 0.0189(8) 0.0207(8) 0.0002(6) 0.0201(7) 0.0000(7) N1 0.0206(9) 0.0126(9) 0.0129(9) 0.0000(7) 0.0085(7) -0.0003(7) C1 0.0202(10) 0.0150(11) 0.0157(11) 0.0001(8) 0.0087(9) 0.0006(8) C2 0.0152(10) 0.0148(11) 0.0138(10) -0.0003(8) 0.0085(8) 0.0011(8) C3 0.0208(11) 0.0142(11) 0.0147(11) -0.0001(8) 0.0069(9) 0.0015(8) C4 0.0154(10) 0.0145(11) 0.0140(10) -0.0001(8) 0.0051(8) -0.0014(8) C5 0.0191(10) 0.0171(12) 0.0168(11) -0.0008(8) 0.0093(9) 0.0003(8) C6 0.0213(11) 0.0145(11) 0.0190(11) -0.0004(8) 0.0121(10) -0.0004(9) C7 0.0245(11) 0.0194(12) 0.0171(11) 0.0012(9) 0.0076(10) 0.0030(9) C8 0.0220(11) 0.0149(11) 0.0175(11) 0.0009(9) 0.0051(9) 0.0014(9) C9 0.0373(12) 0.0159(12) 0.0232(12) -0.0023(9) 0.0145(10) -0.0026(10) _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 C1 1.433(2) . ? O1 H1 0.8400 . ? O2 C2 1.4296(19) . ? O2 H2 0.8400 . ? O3 C3 1.425(2) . ? O3 H3 0.8400 . ? O4 C8 1.235(2) . ? N1 C8 1.361(2) . ? N1 C4 1.462(2) . ? N1 C5 1.467(2) . ? C1 C2 1.528(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.525(2) . ? C2 C4 1.530(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.469(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.171(2) . ? C7 H7 0.9500 . ? C8 C9 1.499(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 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 C1 O1 H1 109.5 . . ? C2 O2 H2 109.5 . . ? C3 O3 H3 109.5 . . ? C8 N1 C4 119.21(15) . . ? C8 N1 C5 122.88(15) . . ? C4 N1 C5 116.83(14) . . ? O1 C1 C2 112.69(14) . . ? O1 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? O1 C1 H1B 109.1 . . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? O2 C2 C3 110.58(14) . . ? O2 C2 C1 103.51(13) . . ? C3 C2 C1 112.94(15) . . ? O2 C2 C4 111.53(14) . . ? C3 C2 C4 105.76(13) . . ? C1 C2 C4 112.66(15) . . ? O3 C3 C2 114.01(14) . . ? O3 C3 H3A 108.8 . . ? C2 C3 H3A 108.8 . . ? O3 C3 H3B 108.8 . . ? C2 C3 H3B 108.8 . . ? H3A C3 H3B 107.6 . . ? N1 C4 C2 115.39(14) . . ? N1 C4 H4A 108.4 . . ? C2 C4 H4A 108.4 . . ? N1 C4 H4B 108.4 . . ? C2 C4 H4B 108.4 . . ? H4A C4 H4B 107.5 . . ? N1 C5 C6 113.58(14) . . ? N1 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? N1 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C7 C6 C5 177.6(2) . . ? C6 C7 H7 180.0 . . ? O4 C8 N1 120.64(17) . . ? O4 C8 C9 120.76(18) . . ? N1 C8 C9 118.59(17) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 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 O1 C1 C2 O2 -178.18(13) . . . . ? O1 C1 C2 C3 -58.56(19) . . . . ? O1 C1 C2 C4 61.20(19) . . . . ? O2 C2 C3 O3 53.81(19) . . . . ? C1 C2 C3 O3 -61.65(19) . . . . ? C4 C2 C3 O3 174.69(14) . . . . ? C8 N1 C4 C2 -100.03(19) . . . . ? C5 N1 C4 C2 91.50(19) . . . . ? O2 C2 C4 N1 -61.11(19) . . . . ? C3 C2 C4 N1 178.62(14) . . . . ? C1 C2 C4 N1 54.8(2) . . . . ? C8 N1 C5 C6 -92.2(2) . . . . ? C4 N1 C5 C6 75.8(2) . . . . ? N1 C5 C6 C7 -154(5) . . . . ? C4 N1 C8 O4 10.8(3) . . . . ? C5 N1 C8 O4 178.50(16) . . . . ? C4 N1 C8 C9 -169.57(16) . . . . ? C5 N1 C8 C9 -1.8(3) . . . . ? 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 O3 H3 O1 0.84 1.88 2.7067(17) 169.5 4_565 O2 H2 O3 0.84 1.87 2.7079(17) 176.6 4_565 O1 H1 O4 0.84 1.97 2.7639(18) 156.3 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.44 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.196 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.046