# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999). SIR97, J. Appl. Cryst. 32, 115-119. Bruker (2009). SAINT V7.68A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2011). APEX2 v2011.4-1, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (2008). SADABS V2008/1, University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; loop_ _publ_author_name _publ_author_address 'Samuel, David' ;Department of Chemistry St. Bonaventure University St. Bonaventure, NY 14778 ; 'Norrell, Kirsten' ;Department of Chemistry St. Bonaventure University St. Bonaventure, NY 14778 ; 'Hilmey, David G.' ;Department of Chemistry St. Bonaventure University St. Bonaventure, NY 14778 ; _publ_contact_author_address ;Department of Chemistry St. Bonaventure University St. Bonaventure, NY 14778 ; _publ_contact_author_email dhilmey@sbu.edu _publ_contact_author_fax 716-375-7618 _publ_contact_author_phone 716-375-2603 _publ_contact_author_name 'David G. Hilmey' data_sbudh01-compound4 _database_code_depnum_ccdc_archive 'CCDC 894615' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common sbudh01 _chemical_melting_point ? _chemical_formula_moiety 'C8 H11 N O5' _chemical_formula_sum 'C8 H11 N O5' _chemical_formula_weight 201.18 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 'P 1 21/n 1' 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 8.1570(6) _cell_length_b 10.1367(7) _cell_length_c 10.8698(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.185(1) _cell_angle_gamma 90.00 _cell_volume 881.70(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 3949 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 37.93 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9449 _exptl_absorpt_correction_T_max 0.9555 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _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 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31864 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0147 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 37.78 _reflns_number_total 4711 _reflns_number_gt 4303 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0546P)^2^+0.1607P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4711 _refine_ls_number_parameters 171 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 O1 O 0.64176(5) 1.16643(4) 0.69540(4) 0.01416(8) Uani 1 1 d . . . O2 O 0.20467(5) 0.88688(4) 0.63237(4) 0.01202(7) Uani 1 1 d . . . H2 H 0.1314(18) 0.8881(14) 0.6778(14) 0.035(3) Uiso 1 1 d . . . O3 O 0.91086(5) 0.90836(4) 0.71721(4) 0.01192(7) Uani 1 1 d . . . H3 H 0.9019(18) 0.8403(14) 0.7527(14) 0.035(3) Uiso 1 1 d . . . O4 O 0.40486(6) 0.62758(4) 0.69421(5) 0.01531(8) Uani 1 1 d . . . H4 H 0.4681(18) 0.5609(14) 0.7180(14) 0.038(4) Uiso 1 1 d . . . O5 O 0.22968(6) 0.82331(5) 0.87289(4) 0.01619(8) Uani 1 1 d . . . N1 N 0.41234(6) 1.04312(4) 0.72344(4) 0.01101(8) Uani 1 1 d . . . H1 H 0.3516(16) 1.1066(13) 0.7471(13) 0.027(3) Uiso 1 1 d . . . C1 C 0.56230(6) 1.06241(5) 0.69013(5) 0.00990(8) Uani 1 1 d . . . C2 C 0.61502(6) 0.93314(5) 0.64533(4) 0.00916(8) Uani 1 1 d . . . C3 C 0.49582(6) 0.84369(5) 0.65155(4) 0.00910(8) Uani 1 1 d . . . C4 C 0.35941(6) 0.90523(5) 0.70935(4) 0.00903(8) Uani 1 1 d . . . C5 C 0.77995(6) 0.91583(5) 0.60748(5) 0.01108(8) Uani 1 1 d . . . H5A H 0.7793(15) 0.8357(12) 0.5581(12) 0.023(3) Uiso 1 1 d . . . H5B H 0.8057(13) 0.9916(12) 0.5588(11) 0.018(2) Uiso 1 1 d . . . C6 C 0.47843(7) 0.70357(5) 0.60859(5) 0.01212(8) Uani 1 1 d . . . H6A H 0.4013(13) 0.7008(11) 0.5247(10) 0.018(2) Uiso 1 1 d . . . H6B H 0.5884(14) 0.6666(11) 0.6042(11) 0.017(2) Uiso 1 1 d . . . C7 C 0.36162(6) 0.85124(5) 0.84377(5) 0.01114(8) Uani 1 1 d . . . C8 C 0.52717(8) 0.83924(6) 0.93172(5) 0.01662(10) Uani 1 1 d . . . H8A H 0.6009(15) 0.9135(12) 0.9276(12) 0.026(3) Uiso 1 1 d . . . H8B H 0.5807(17) 0.7590(14) 0.9086(13) 0.037(3) Uiso 1 1 d . . . H8C H 0.5124(18) 0.8353(13) 1.0172(13) 0.032(3) Uiso 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 O1 0.01312(17) 0.00850(15) 0.02106(18) -0.00171(12) 0.00379(13) -0.00227(11) O2 0.00679(14) 0.01699(17) 0.01186(15) 0.00072(12) 0.00078(11) 0.00007(11) O3 0.00836(15) 0.01045(15) 0.01638(17) 0.00204(12) 0.00098(12) -0.00044(11) O4 0.01429(17) 0.00935(15) 0.0240(2) 0.00379(13) 0.00785(14) 0.00026(12) O5 0.01353(17) 0.01950(18) 0.01682(17) 0.00539(14) 0.00611(13) 0.00077(13) N1 0.01008(16) 0.00807(15) 0.01576(18) -0.00027(12) 0.00465(13) 0.00105(12) C1 0.00898(17) 0.00859(16) 0.01199(17) 0.00000(13) 0.00171(13) 0.00017(12) C2 0.00803(17) 0.00833(16) 0.01125(17) 0.00002(12) 0.00221(13) 0.00022(12) C3 0.00787(17) 0.00834(16) 0.01113(17) 0.00019(12) 0.00198(13) 0.00032(12) C4 0.00730(16) 0.00890(16) 0.01083(17) 0.00061(12) 0.00161(13) 0.00048(12) C5 0.00880(18) 0.01260(18) 0.01241(18) 0.00020(14) 0.00345(14) 0.00017(13) C6 0.01271(19) 0.00850(17) 0.0159(2) -0.00134(14) 0.00466(15) -0.00126(14) C7 0.01136(19) 0.01081(17) 0.01127(18) 0.00139(14) 0.00222(14) 0.00118(14) C8 0.0149(2) 0.0200(2) 0.0132(2) 0.00249(17) -0.00166(16) 0.00163(17) _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 1.2332(6) . ? O2 C4 1.3850(6) . ? O2 H2 0.846(15) . ? O3 C5 1.4403(7) . ? O3 H3 0.800(15) . ? O4 C6 1.4270(7) . ? O4 H4 0.859(14) . ? O5 C7 1.2127(7) . ? N1 C1 1.3556(7) . ? N1 C4 1.4621(7) . ? N1 H1 0.881(13) . ? C1 C2 1.4901(7) . ? C2 C3 1.3408(7) . ? C2 C5 1.4915(7) . ? C3 C6 1.4932(7) . ? C3 C4 1.5143(7) . ? C4 C7 1.5571(7) . ? C5 H5A 0.973(13) . ? C5 H5B 0.978(12) . ? C6 H6A 1.002(11) . ? C6 H6B 0.982(11) . ? C7 C8 1.5005(8) . ? C8 H8A 0.970(13) . ? C8 H8B 0.979(14) . ? C8 H8C 0.961(14) . ? 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 O2 H2 108.1(10) . . ? C5 O3 H3 108.8(10) . . ? C6 O4 H4 108.5(10) . . ? C1 N1 C4 111.92(4) . . ? C1 N1 H1 124.1(8) . . ? C4 N1 H1 123.9(8) . . ? O1 C1 N1 127.18(5) . . ? O1 C1 C2 125.78(5) . . ? N1 C1 C2 107.04(4) . . ? C3 C2 C1 108.67(4) . . ? C3 C2 C5 129.50(4) . . ? C1 C2 C5 121.77(4) . . ? C2 C3 C6 130.79(5) . . ? C2 C3 C4 109.92(4) . . ? C6 C3 C4 119.26(4) . . ? O2 C4 N1 114.05(4) . . ? O2 C4 C3 110.54(4) . . ? N1 C4 C3 102.21(4) . . ? O2 C4 C7 111.28(4) . . ? N1 C4 C7 106.76(4) . . ? C3 C4 C7 111.65(4) . . ? O3 C5 C2 109.96(4) . . ? O3 C5 H5A 109.7(7) . . ? C2 C5 H5A 110.0(7) . . ? O3 C5 H5B 106.7(6) . . ? C2 C5 H5B 110.9(6) . . ? H5A C5 H5B 109.6(10) . . ? O4 C6 C3 109.63(4) . . ? O4 C6 H6A 108.0(6) . . ? C3 C6 H6A 108.4(7) . . ? O4 C6 H6B 109.2(7) . . ? C3 C6 H6B 110.3(7) . . ? H6A C6 H6B 111.3(9) . . ? O5 C7 C8 123.32(5) . . ? O5 C7 C4 118.53(5) . . ? C8 C7 C4 118.13(5) . . ? C7 C8 H8A 113.4(7) . . ? C7 C8 H8B 107.2(8) . . ? H8A C8 H8B 108.8(11) . . ? C7 C8 H8C 110.7(9) . . ? H8A C8 H8C 105.8(11) . . ? H8B C8 H8C 111.1(12) . . ? 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 C4 N1 C1 O1 -177.56(5) . . . . ? C4 N1 C1 C2 2.38(6) . . . . ? O1 C1 C2 C3 -179.12(5) . . . . ? N1 C1 C2 C3 0.94(6) . . . . ? O1 C1 C2 C5 3.38(8) . . . . ? N1 C1 C2 C5 -176.56(4) . . . . ? C1 C2 C3 C6 174.18(5) . . . . ? C5 C2 C3 C6 -8.58(9) . . . . ? C1 C2 C3 C4 -3.72(5) . . . . ? C5 C2 C3 C4 173.52(5) . . . . ? C1 N1 C4 O2 -123.67(5) . . . . ? C1 N1 C4 C3 -4.35(5) . . . . ? C1 N1 C4 C7 112.99(5) . . . . ? C2 C3 C4 O2 126.66(4) . . . . ? C6 C3 C4 O2 -51.52(6) . . . . ? C2 C3 C4 N1 4.89(5) . . . . ? C6 C3 C4 N1 -173.29(4) . . . . ? C2 C3 C4 C7 -108.89(5) . . . . ? C6 C3 C4 C7 72.93(6) . . . . ? C3 C2 C5 O3 -100.65(6) . . . . ? C1 C2 C5 O3 76.28(6) . . . . ? C2 C3 C6 O4 144.33(5) . . . . ? C4 C3 C6 O4 -37.93(6) . . . . ? O2 C4 C7 O5 -12.89(7) . . . . ? N1 C4 C7 O5 112.14(5) . . . . ? C3 C4 C7 O5 -136.93(5) . . . . ? O2 C4 C7 C8 168.42(5) . . . . ? N1 C4 C7 C8 -66.55(6) . . . . ? C3 C4 C7 C8 44.38(6) . . . . ? 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 O2 H2 O3 0.846(15) 1.940(15) 2.7384(6) 157.1(14) 1_455 O2 H2 O5 0.846(15) 2.216(15) 2.6617(6) 112.9(12) . O3 H3 O1 0.800(15) 1.906(15) 2.6943(6) 168.4(15) 2_646 O4 H4 O3 0.859(14) 1.896(15) 2.7501(6) 173.1(14) 2_646 N1 H1 O4 0.881(13) 2.312(13) 3.0211(6) 137.6(11) 2_556 N1 H1 O5 0.881(13) 2.575(13) 3.1678(7) 125.4(11) 2_556 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 37.78 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.723 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.061 _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999). SIR97, J. Appl. Cryst. 32, 115-119. Bruker (2009). SAINT V7.68A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2011). APEX2 v2011.4-1, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (2008). SADABS V2008/1, University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; data_sbudh02-compound9 _database_code_depnum_ccdc_archive 'CCDC 894616' _vrf_PLAT094_sbudh02 ; PROBLEM: _C Ratio of Maximum / Minimum Residual Density .... 2.63 RESPONSE: The largest residual electron density peaks are bonding electrons. ; _vrf_PLAT097_sbudh02 ; PROBLEM: _C Large Reported Max. (Positive) Residual Density 0.62 eA-3 RESPONSE: See above. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common sbudh02 _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 D3 N2 O5' _chemical_formula_sum 'C13 H13 D3 N2 O5' _chemical_formula_weight 283.30 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' D D 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 orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 7.8267(6) _cell_length_b 11.7766(8) _cell_length_c 26.1425(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2409.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100.0(5) _cell_measurement_reflns_used 4025 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 37.82 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9718 _exptl_absorpt_correction_T_max 0.9764 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(5) _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 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 83310 _diffrn_reflns_av_R_equivalents 0.0644 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 37.78 _reflns_number_total 6466 _reflns_number_gt 5075 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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. The identity of the deuterium atoms was provided by the chemist. ; _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^)+(0.0635P)^2^+0.4428P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6466 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1236 _refine_ls_wR_factor_gt 0.1174 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 O1 O 0.63826(9) 0.56211(6) 0.25216(3) 0.01712(12) Uani 1 1 d . . . O2 O 0.27462(10) 0.76502(6) 0.15174(3) 0.02235(15) Uani 1 1 d . . . O3 O 0.72057(9) 0.29490(5) 0.12272(3) 0.01827(13) Uani 1 1 d . . . O4 O 0.38658(10) 0.23782(6) 0.00287(3) 0.02093(14) Uani 1 1 d . . . D4 D 0.361(2) 0.1648(17) -0.0050(7) 0.042(5) Uiso 1 1 d . . . O5 O 0.20259(9) 0.50847(6) -0.00678(2) 0.01508(12) Uani 1 1 d . . . D5 D 0.265(3) 0.4744(15) -0.0326(7) 0.044(5) Uiso 1 1 d . . . N1 N 0.46738(9) 0.68485(6) 0.20721(3) 0.01257(12) Uani 1 1 d . . . N2 N 0.61364(9) 0.57297(6) 0.09026(3) 0.01067(11) Uani 1 1 d . . . D2 D 0.6462(17) 0.6395(12) 0.0990(5) 0.015(3) Uiso 1 1 d . . . C1 C 0.54742(10) 0.58211(7) 0.21552(3) 0.01213(13) Uani 1 1 d . . . C2 C 0.50369(10) 0.50395(6) 0.17166(3) 0.01107(12) Uani 1 1 d . . . H2 H 0.4683(18) 0.4277(12) 0.1852(5) 0.017(3) Uiso 1 1 d . . . C3 C 0.36254(10) 0.56583(7) 0.14198(3) 0.01117(12) Uani 1 1 d . . . H3 H 0.2502(19) 0.5329(12) 0.1457(5) 0.020(3) Uiso 1 1 d . . . C4 C 0.35839(11) 0.68392(7) 0.16546(3) 0.01356(13) Uani 1 1 d . . . C5 C 0.65462(10) 0.49263(6) 0.13143(3) 0.01051(12) Uani 1 1 d . . . C6 C 0.63257(10) 0.37438(6) 0.10799(3) 0.01128(12) Uani 1 1 d . . . C7 C 0.49098(10) 0.35937(6) 0.07087(3) 0.01101(12) Uani 1 1 d . . . C8 C 0.38315(10) 0.44795(6) 0.06368(3) 0.01041(12) Uani 1 1 d . . . C9 C 0.42737(10) 0.56325(6) 0.08572(3) 0.01033(12) Uani 1 1 d . . . H9 H 0.3819(16) 0.6229(11) 0.0652(5) 0.012(3) Uiso 1 1 d . . . C10 C 0.48100(12) 0.77890(7) 0.24281(3) 0.01686(15) Uani 1 1 d . . . H10A H 0.426(2) 0.7519(13) 0.2736(7) 0.032(4) Uiso 1 1 d . . . H10B H 0.600(2) 0.7997(14) 0.2484(6) 0.032(4) Uiso 1 1 d . . . H10C H 0.4210(19) 0.8425(12) 0.2285(6) 0.023(3) Uiso 1 1 d . . . C11 C 0.83358(11) 0.50969(8) 0.15202(4) 0.01560(14) Uani 1 1 d . . . H11A H 0.857(2) 0.5899(14) 0.1628(7) 0.029(4) Uiso 1 1 d . . . H11B H 0.8557(19) 0.4584(13) 0.1798(6) 0.025(4) Uiso 1 1 d . . . H11C H 0.918(2) 0.4948(14) 0.1237(6) 0.035(4) Uiso 1 1 d . . . C12 C 0.47565(11) 0.24061(7) 0.04998(3) 0.01344(13) Uani 1 1 d . . . H12A H 0.5878(19) 0.2069(13) 0.0469(6) 0.024(4) Uiso 1 1 d . . . H12B H 0.4111(17) 0.1934(11) 0.0758(5) 0.013(3) Uiso 1 1 d . . . C13 C 0.21082(10) 0.44110(7) 0.03840(3) 0.01285(13) Uani 1 1 d . . . H13A H 0.1854(17) 0.3644(11) 0.0308(5) 0.015(3) Uiso 1 1 d . . . H13B H 0.1252(17) 0.4769(11) 0.0630(5) 0.014(3) Uiso 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 O1 0.0215(3) 0.0178(3) 0.0121(3) -0.0007(2) -0.0045(2) 0.0022(2) O2 0.0306(4) 0.0175(3) 0.0190(3) -0.0052(2) -0.0073(3) 0.0119(3) O3 0.0220(3) 0.0122(3) 0.0206(3) -0.0023(2) -0.0052(2) 0.0065(2) O4 0.0283(4) 0.0148(3) 0.0197(3) -0.0056(2) -0.0091(3) 0.0017(2) O5 0.0164(3) 0.0169(3) 0.0119(3) -0.0011(2) -0.0004(2) 0.0049(2) N1 0.0157(3) 0.0110(3) 0.0111(3) -0.0027(2) -0.0014(2) 0.0010(2) N2 0.0118(3) 0.0085(2) 0.0117(3) 0.00015(19) 0.0004(2) -0.00102(19) C1 0.0146(3) 0.0118(3) 0.0101(3) -0.0008(2) 0.0003(2) 0.0000(2) C2 0.0138(3) 0.0098(3) 0.0095(3) -0.0005(2) -0.0002(2) 0.0001(2) C3 0.0118(3) 0.0115(3) 0.0103(3) -0.0022(2) 0.0002(2) 0.0008(2) C4 0.0153(3) 0.0137(3) 0.0116(3) -0.0028(2) -0.0007(2) 0.0029(2) C5 0.0112(3) 0.0094(3) 0.0109(3) -0.0013(2) -0.0003(2) 0.0004(2) C6 0.0125(3) 0.0098(3) 0.0115(3) -0.0013(2) 0.0003(2) 0.0010(2) C7 0.0128(3) 0.0092(3) 0.0110(3) -0.0012(2) 0.0005(2) -0.0001(2) C8 0.0124(3) 0.0098(3) 0.0090(3) -0.0013(2) 0.0005(2) -0.0005(2) C9 0.0116(3) 0.0094(3) 0.0101(3) -0.0011(2) -0.0006(2) 0.0007(2) C10 0.0218(4) 0.0135(3) 0.0153(3) -0.0055(3) -0.0013(3) 0.0003(3) C11 0.0127(3) 0.0167(3) 0.0175(4) -0.0028(3) -0.0030(3) 0.0004(3) C12 0.0163(3) 0.0100(3) 0.0140(3) -0.0029(2) -0.0006(2) -0.0001(2) C13 0.0115(3) 0.0149(3) 0.0122(3) -0.0021(2) -0.0006(2) 0.0001(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 O1 C1 1.2160(10) . ? O2 C4 1.2127(10) . ? O3 C6 1.2241(10) . ? O4 C12 1.4155(11) . ? O4 D4 0.907(19) . ? O5 C13 1.4243(11) . ? O5 D5 0.927(19) . ? N1 C1 1.3797(10) . ? N1 C4 1.3853(11) . ? N1 C10 1.4507(11) . ? N2 C9 1.4671(10) . ? N2 C5 1.4683(10) . ? N2 D2 0.856(14) . ? C1 C2 1.5096(11) . ? C2 H2 1.004(14) . ? C2 C3 1.5342(11) . ? C2 C5 1.5874(11) . ? C3 H3 0.966(15) . ? C3 C4 1.5205(11) . ? C3 C9 1.5562(11) . ? C5 C11 1.5139(11) . ? C5 C6 1.5312(11) . ? C6 C7 1.4836(11) . ? C7 C8 1.3549(11) . ? C7 C12 1.5063(11) . ? C8 C13 1.5042(11) . ? C8 C9 1.5150(11) . ? C9 H9 0.953(13) . ? C10 H10A 0.965(17) . ? C10 H10C 0.960(15) . ? C10 H10B 0.972(17) . ? C11 H11B 0.960(16) . ? C11 H11C 1.006(17) . ? C11 H11A 1.003(16) . ? C12 H12A 0.967(15) . ? C12 H12B 1.010(13) . ? C13 H13A 0.946(13) . ? C13 H13B 1.021(14) . ? 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 C12 O4 D4 109.2(12) . . ? C13 O5 D5 109.9(11) . . ? C1 N1 C4 113.37(7) . . ? C1 N1 C10 122.36(7) . . ? C4 N1 C10 123.83(7) . . ? C9 N2 C5 103.08(6) . . ? C9 N2 D2 112.9(9) . . ? C5 N2 D2 109.2(9) . . ? O1 C1 N1 124.01(7) . . ? O1 C1 C2 127.79(7) . . ? N1 C1 C2 108.19(6) . . ? H2 C2 C1 109.9(8) . . ? H2 C2 C3 113.9(8) . . ? C1 C2 C3 104.94(6) . . ? H2 C2 C5 111.3(8) . . ? C1 C2 C5 112.69(6) . . ? C3 C2 C5 103.92(6) . . ? H3 C3 C4 107.9(9) . . ? H3 C3 C2 114.4(9) . . ? C4 C3 C2 104.22(6) . . ? H3 C3 C9 112.6(9) . . ? C4 C3 C9 113.98(6) . . ? C2 C3 C9 103.53(6) . . ? O2 C4 N1 124.03(8) . . ? O2 C4 C3 127.77(8) . . ? N1 C4 C3 108.19(7) . . ? N2 C5 C11 112.16(7) . . ? N2 C5 C6 105.56(6) . . ? C11 C5 C6 111.55(6) . . ? N2 C5 C2 105.60(6) . . ? C11 C5 C2 116.21(7) . . ? C6 C5 C2 104.93(6) . . ? O3 C6 C7 122.33(7) . . ? O3 C6 C5 120.41(7) . . ? C7 C6 C5 117.02(6) . . ? C8 C7 C6 117.67(7) . . ? C8 C7 C12 127.95(7) . . ? C6 C7 C12 114.04(7) . . ? C7 C8 C13 125.32(7) . . ? C7 C8 C9 119.67(7) . . ? C13 C8 C9 114.84(6) . . ? H9 C9 N2 111.1(8) . . ? H9 C9 C8 111.2(8) . . ? N2 C9 C8 109.13(6) . . ? H9 C9 C3 113.3(8) . . ? N2 C9 C3 104.23(6) . . ? C8 C9 C3 107.60(6) . . ? H10A C10 H10C 111.3(13) . . ? H10A C10 H10B 112.5(14) . . ? H10C C10 H10B 109.2(13) . . ? H10A C10 N1 104.5(9) . . ? H10C C10 N1 108.1(9) . . ? H10B C10 N1 111.1(10) . . ? H11B C11 H11C 109.2(13) . . ? H11B C11 H11A 110.3(13) . . ? H11C C11 H11A 104.7(13) . . ? H11B C11 C5 110.6(9) . . ? H11C C11 C5 108.7(10) . . ? H11A C11 C5 113.1(9) . . ? H12A C12 H12B 106.5(12) . . ? H12A C12 O4 111.4(9) . . ? H12B C12 O4 108.8(8) . . ? H12A C12 C7 109.8(9) . . ? H12B C12 C7 108.0(8) . . ? O4 C12 C7 112.10(7) . . ? H13A C13 H13B 112.9(11) . . ? H13A C13 O5 110.4(8) . . ? H13B C13 O5 105.3(8) . . ? H13A C13 C8 109.4(8) . . ? H13B C13 C8 106.8(8) . . ? O5 C13 C8 112.02(7) . . ? 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 C4 N1 C1 O1 -174.41(8) . . . . ? C10 N1 C1 O1 -1.73(13) . . . . ? C4 N1 C1 C2 6.38(9) . . . . ? C10 N1 C1 C2 179.06(7) . . . . ? O1 C1 C2 H2 47.9(8) . . . . ? N1 C1 C2 H2 -132.9(8) . . . . ? O1 C1 C2 C3 170.71(8) . . . . ? N1 C1 C2 C3 -10.12(8) . . . . ? O1 C1 C2 C5 -76.87(10) . . . . ? N1 C1 C2 C5 102.30(7) . . . . ? H2 C2 C3 H3 12.5(13) . . . . ? C1 C2 C3 H3 -107.7(9) . . . . ? C5 C2 C3 H3 133.8(9) . . . . ? H2 C2 C3 C4 130.1(9) . . . . ? C1 C2 C3 C4 9.85(8) . . . . ? C5 C2 C3 C4 -108.66(7) . . . . ? H2 C2 C3 C9 -110.5(9) . . . . ? C1 C2 C3 C9 129.34(6) . . . . ? C5 C2 C3 C9 10.82(7) . . . . ? C1 N1 C4 O2 179.39(9) . . . . ? C10 N1 C4 O2 6.83(14) . . . . ? C1 N1 C4 C3 0.28(10) . . . . ? C10 N1 C4 C3 -172.28(8) . . . . ? H3 C3 C4 O2 -63.7(9) . . . . ? C2 C3 C4 O2 174.35(9) . . . . ? C9 C3 C4 O2 62.21(12) . . . . ? H3 C3 C4 N1 115.4(9) . . . . ? C2 C3 C4 N1 -6.58(9) . . . . ? C9 C3 C4 N1 -118.72(7) . . . . ? C9 N2 C5 C11 -165.44(6) . . . . ? C9 N2 C5 C6 72.89(7) . . . . ? C9 N2 C5 C2 -37.92(7) . . . . ? H2 C2 C5 N2 138.9(9) . . . . ? C1 C2 C5 N2 -97.08(7) . . . . ? C3 C2 C5 N2 15.97(7) . . . . ? H2 C2 C5 C11 -96.0(9) . . . . ? C1 C2 C5 C11 27.96(9) . . . . ? C3 C2 C5 C11 141.00(7) . . . . ? H2 C2 C5 C6 27.7(9) . . . . ? C1 C2 C5 C6 151.66(6) . . . . ? C3 C2 C5 C6 -95.29(7) . . . . ? N2 C5 C6 O3 148.75(8) . . . . ? C11 C5 C6 O3 26.68(11) . . . . ? C2 C5 C6 O3 -99.96(9) . . . . ? N2 C5 C6 C7 -36.75(9) . . . . ? C11 C5 C6 C7 -158.82(7) . . . . ? C2 C5 C6 C7 74.54(8) . . . . ? O3 C6 C7 C8 168.92(8) . . . . ? C5 C6 C7 C8 -5.46(11) . . . . ? O3 C6 C7 C12 -4.83(11) . . . . ? C5 C6 C7 C12 -179.22(7) . . . . ? C6 C7 C8 C13 -164.15(7) . . . . ? C12 C7 C8 C13 8.61(13) . . . . ? C6 C7 C8 C9 10.80(11) . . . . ? C12 C7 C8 C9 -176.44(7) . . . . ? C5 N2 C9 H9 167.6(8) . . . . ? C5 N2 C9 C8 -69.45(7) . . . . ? C5 N2 C9 C3 45.27(7) . . . . ? C7 C8 C9 H9 149.7(8) . . . . ? C13 C8 C9 H9 -34.8(8) . . . . ? C7 C8 C9 N2 26.86(10) . . . . ? C13 C8 C9 N2 -157.68(6) . . . . ? C7 C8 C9 C3 -85.66(9) . . . . ? C13 C8 C9 C3 89.80(8) . . . . ? H3 C3 C9 H9 80.5(13) . . . . ? C4 C3 C9 H9 -42.8(8) . . . . ? C2 C3 C9 H9 -155.3(8) . . . . ? H3 C3 C9 N2 -158.6(9) . . . . ? C4 C3 C9 N2 78.09(8) . . . . ? C2 C3 C9 N2 -34.46(7) . . . . ? H3 C3 C9 C8 -42.8(9) . . . . ? C4 C3 C9 C8 -166.11(6) . . . . ? C2 C3 C9 C8 81.33(7) . . . . ? C1 N1 C10 H10A -64.5(11) . . . . ? C4 N1 C10 H10A 107.4(11) . . . . ? C1 N1 C10 H10C 176.9(10) . . . . ? C4 N1 C10 H10C -11.2(10) . . . . ? C1 N1 C10 H10B 57.0(11) . . . . ? C4 N1 C10 H10B -131.1(11) . . . . ? N2 C5 C11 H11B 177.6(10) . . . . ? C6 C5 C11 H11B -64.2(10) . . . . ? C2 C5 C11 H11B 56.0(10) . . . . ? N2 C5 C11 H11C -62.5(10) . . . . ? C6 C5 C11 H11C 55.7(10) . . . . ? C2 C5 C11 H11C 175.9(10) . . . . ? N2 C5 C11 H11A 53.3(11) . . . . ? C6 C5 C11 H11A 171.5(11) . . . . ? C2 C5 C11 H11A -68.3(11) . . . . ? C8 C7 C12 H12A 153.1(10) . . . . ? C6 C7 C12 H12A -33.9(10) . . . . ? C8 C7 C12 H12B -91.2(8) . . . . ? C6 C7 C12 H12B 81.8(8) . . . . ? C8 C7 C12 O4 28.68(12) . . . . ? C6 C7 C12 O4 -158.34(7) . . . . ? C7 C8 C13 H13A 4.7(9) . . . . ? C9 C8 C13 H13A -170.5(9) . . . . ? C7 C8 C13 H13B 127.2(8) . . . . ? C9 C8 C13 H13B -48.0(8) . . . . ? C7 C8 C13 O5 -118.02(9) . . . . ? C9 C8 C13 O5 66.82(9) . . . . ? 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 O4 D4 O5 0.907(19) 1.91(2) 2.8011(10) 168.0(18) 8_655 O5 D5 N2 0.927(19) 1.87(2) 2.7842(10) 171.0(17) 5_665 N2 D2 O3 0.856(14) 2.195(14) 3.0389(9) 168.8(12) 8_765 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 37.78 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.621 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.072