# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name _publ_author_address 'Steven Zimmerman' ; University of Illinois School of Chemical Sciences, Box 59-1 505 South Mathews Avenue Urbana, Illinois 61801 USA ; 'Jonathan F Arambula' ; University of Illinois School of Chemical Sciences, Box 59-1 505 South Mathews Avenue Urbana, Illinois 61801 USA ; 'Anne M Baranger' '' 'Hugo C Ong' '' 'Sreenivasa Rao Ramisetty' '' _publ_contact_author_name 'Steven Zimmerman' _publ_contact_author_email SCZIMMER@ILLINOIS.EDU _publ_section_title ; Molecular Recognition of a Thymine Bulge by a High Affinity, Deazaguanine-based (DAD) Hydrogen Bonding Ligand ; _publ_contact_author ; Scott R. Wilson University of Illinois School of Chemical Sciences, Box 59-1 505 South Mathews Avenue Urbana, Illinois 61801 USA ; _publ_contact_author_fax '1 217 244 8068' _publ_contact_author_phone '1 217 244 1708' _publ_contact_letter ; Please consider this CIF submission for publication as a structural paper in Acta Crystallographica E. ; _publ_requested_category FO _publ_requested_coeditor_name ? # Attachment 'g52nas.cif' data_g52nas _database_code_depnum_ccdc_archive 'CCDC 704965' _audit_creation_method SHELXL-97 _audit_update_record ; 2006-10-20 text and data added, srw ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H20 N4 O4' _chemical_formula_sum 'C15 H20 N4 O4' _chemical_formula_structural ? _chemical_formula_weight 320.35 _chemical_absolute_configuration . _chemical_formula_analytical ? _chemical_compound_source ? 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 21/c ' _symmetry_space_group_name_Hall '-P 2ybc ' 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 10.566(5) _cell_length_b 11.898(6) _cell_length_c 13.224(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.221(7) _cell_angle_gamma 90.00 _cell_volume 1659.9(14) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 857 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 19.18 _exptl_crystal_description tabular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_crystal_id g52nas _exptl_crystal_preparation ; The data crystal was mounted using oil (Parantone-N, Exxon) to a 0.3 mm cryo-loop (Hampton Research) with the (0 -1 01) scattering planes roughly normal to the spindle axis. ; _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9443 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details 'SHELXTL/XPREP (Bruker, 2001)' _exptl_special_details ; The data crystal was larger than ideal; however, the weak diffraction intensity required maximum volume. One distinct cell was identified using SMART (Bruker, 2001). Four frame series were integrated and filtered for statistical outliers using SAINT (Bruker, 2001) then corrected for absorption by integration using SHELXTL/XPREP (Bruker, 2001) before using SAINT/SADABS (Bruker, 2001) to sort, merge, and scale the combined data. A series of identical frames was collected twice during the experiment to monitor decay. No decay correction was applied. ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id g52nas _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_device 'Siemens Platform/CCD' _diffrn_measurement_method 'profile data from \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 35 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 530 _diffrn_standards_decay_% 0.8 _diffrn_reflns_number 12908 _diffrn_reflns_av_R_equivalents 0.1204 _diffrn_reflns_av_sigmaI/netI 0.1275 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.41 _reflns_number_total 3036 _reflns_number_gt 1472 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT V6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT V6.22 (Bruker, 2001)' _computing_structure_solution 'SHELXTL V6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXTL V6.12 (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL V6.12 (Bruker, 2001)' _computing_publication_material 'XCIF (Bruker, 2001)' _refine_special_details ; Structure was phased by dual space methods. Systematic conditions suggested the unambiguous space group. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F^2^. The highest peaks in the final difference Fourier map were in the vicinity of atoms C17, O10, and O20; the final map had no other significant features. A final analysis of variance between observed and calculated structure factors showed no dependence on amplitude or resolution. ; _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^)+(0.0482P)^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_number_reflns 3036 _refine_ls_number_parameters 221 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1680 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.1013 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _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 N1 N 0.9658(2) 0.7309(2) 0.24308(18) 0.0285(7) Uani 1 1 d D . . H1 H 0.995(3) 0.685(2) 0.2916(17) 0.043 Uiso 1 1 d D . . C2 C 1.0076(3) 0.8395(3) 0.2558(2) 0.0260(8) Uani 1 1 d . . . N3 N 0.9794(2) 0.9212(2) 0.19283(17) 0.0290(7) Uani 1 1 d . . . C4 C 0.9037(3) 0.8875(3) 0.1111(2) 0.0270(8) Uani 1 1 d . . . C5 C 0.8594(3) 0.7798(2) 0.0897(2) 0.0258(8) Uani 1 1 d . . . C6 C 0.8880(3) 0.6943(3) 0.1608(2) 0.0280(8) Uani 1 1 d . . . C7 C 0.7848(3) 0.7847(3) -0.0028(2) 0.0300(8) Uani 1 1 d . . . H7 H 0.7420 0.7236 -0.0360 0.036 Uiso 1 1 calc R . . C8 C 0.7861(3) 0.8932(3) -0.0350(2) 0.0274(8) Uani 1 1 d . . . N9 N 0.8590(2) 0.9560(2) 0.03525(19) 0.0295(7) Uani 1 1 d D . . H9 H 0.868(3) 1.0288(15) 0.031(2) 0.044 Uiso 1 1 d D . . O10 O 0.8509(2) 0.59472(17) 0.15837(15) 0.0357(6) Uani 1 1 d . . . O11 O 1.1057(2) 0.69165(18) 0.41190(15) 0.0375(6) Uani 1 1 d . . . N12 N 1.0870(2) 0.8646(2) 0.34011(19) 0.0311(7) Uani 1 1 d D . . H12 H 1.109(3) 0.9350(16) 0.341(2) 0.047 Uiso 1 1 d D . . C13 C 1.1352(3) 0.7920(3) 0.4131(2) 0.0301(8) Uani 1 1 d . . . C14 C 1.2280(3) 0.8426(3) 0.4933(2) 0.0314(8) Uani 1 1 d . . . C15 C 1.2694(3) 0.7497(3) 0.5678(2) 0.0462(10) Uani 1 1 d . . . H15A H 1.1950 0.7192 0.5993 0.069 Uiso 1 1 calc R . . H15B H 1.3285 0.7808 0.6204 0.069 Uiso 1 1 calc R . . H15C H 1.3114 0.6896 0.5316 0.069 Uiso 1 1 calc R . . C16 C 1.1647(3) 0.9378(3) 0.5495(2) 0.0413(9) Uani 1 1 d . . . H16A H 1.1497 1.0017 0.5036 0.062 Uiso 1 1 calc R . . H16B H 1.2202 0.9613 0.6075 0.062 Uiso 1 1 calc R . . H16C H 1.0838 0.9115 0.5734 0.062 Uiso 1 1 calc R . . C17 C 1.3450(3) 0.8860(3) 0.4413(3) 0.0483(10) Uani 1 1 d . . . H17A H 1.3203 0.9486 0.3963 0.072 Uiso 1 1 calc R . . H17B H 1.3806 0.8253 0.4017 0.072 Uiso 1 1 calc R . . H17C H 1.4088 0.9118 0.4928 0.072 Uiso 1 1 calc R . . C18 C 0.7221(3) 0.9481(3) -0.1256(2) 0.0306(8) Uani 1 1 d . . . H18A H 0.7438 0.9058 -0.1867 0.037 Uiso 1 1 calc R . . H18B H 0.7565 1.0251 -0.1316 0.037 Uiso 1 1 calc R . . C19 C 0.5812(3) 0.9553(3) -0.1239(2) 0.0366(9) Uani 1 1 d . . . O20 O 0.5143(2) 0.8959(2) -0.0768(2) 0.0725(9) Uani 1 1 d . . . O21 O 0.5360(2) 1.03690(19) -0.18570(15) 0.0418(6) Uani 1 1 d . . . C22 C 0.4007(3) 1.0534(3) -0.1932(3) 0.0549(11) Uani 1 1 d . . . H22A H 0.3700 1.0734 -0.1261 0.066 Uiso 1 1 calc R . . H22B H 0.3575 0.9837 -0.2170 0.066 Uiso 1 1 calc R . . C23 C 0.3736(3) 1.1459(3) -0.2664(3) 0.0679(13) Uani 1 1 d . . . H23A H 0.2817 1.1559 -0.2766 0.102 Uiso 1 1 calc R . . H23B H 0.4092 1.1273 -0.3312 0.102 Uiso 1 1 calc R . . H23C H 0.4120 1.2157 -0.2399 0.102 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 N1 0.0387(17) 0.0181(16) 0.0280(16) 0.0019(12) -0.0045(13) -0.0007(13) C2 0.0273(19) 0.0219(19) 0.0284(18) -0.0013(16) -0.0008(15) -0.0002(16) N3 0.0362(17) 0.0228(16) 0.0272(15) 0.0030(13) -0.0060(13) 0.0002(13) C4 0.027(2) 0.0231(19) 0.031(2) 0.0030(15) 0.0010(16) 0.0044(15) C5 0.031(2) 0.0193(19) 0.0273(18) -0.0005(15) 0.0002(15) -0.0001(15) C6 0.034(2) 0.0200(19) 0.0302(19) -0.0047(15) 0.0019(16) 0.0018(16) C7 0.037(2) 0.0202(19) 0.032(2) -0.0048(16) -0.0006(16) -0.0016(16) C8 0.0282(19) 0.0254(19) 0.0282(19) -0.0038(15) -0.0032(16) -0.0017(16) N9 0.0386(17) 0.0171(14) 0.0320(15) 0.0031(14) -0.0042(13) -0.0005(15) O10 0.0471(15) 0.0199(13) 0.0392(13) -0.0015(11) -0.0067(11) -0.0012(11) O11 0.0500(15) 0.0183(13) 0.0427(13) 0.0061(10) -0.0091(11) -0.0015(11) N12 0.0397(17) 0.0179(16) 0.0343(16) 0.0027(14) -0.0102(14) -0.0027(14) C13 0.033(2) 0.025(2) 0.0320(19) -0.0006(17) 0.0039(16) 0.0057(17) C14 0.034(2) 0.028(2) 0.0312(19) 0.0038(16) -0.0051(16) 0.0027(17) C15 0.052(2) 0.043(2) 0.042(2) 0.0110(18) -0.0160(18) -0.0006(19) C16 0.052(2) 0.036(2) 0.035(2) -0.0014(16) -0.0045(18) -0.0030(18) C17 0.039(2) 0.052(2) 0.054(2) 0.0039(19) 0.0017(19) -0.0033(19) C18 0.033(2) 0.029(2) 0.0298(19) 0.0011(16) -0.0002(16) -0.0013(17) C19 0.042(2) 0.032(2) 0.034(2) 0.0055(18) -0.0031(18) -0.001(2) O20 0.0480(18) 0.079(2) 0.090(2) 0.0483(18) -0.0001(15) -0.0038(15) O21 0.0399(16) 0.0468(15) 0.0381(14) 0.0120(12) -0.0019(12) 0.0074(13) C22 0.034(2) 0.076(3) 0.054(2) 0.017(2) -0.0015(19) 0.015(2) C23 0.058(3) 0.084(3) 0.062(3) 0.029(2) 0.008(2) 0.033(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 N1 C2 1.373(4) . ? N1 C6 1.396(4) . ? N1 H1 0.888(17) . ? C2 N3 1.304(3) . ? C2 N12 1.390(4) . ? N3 C4 1.368(3) . ? C4 N9 1.357(4) . ? C4 C5 1.388(4) . ? C5 C6 1.406(4) . ? C5 C7 1.418(4) . ? C6 O10 1.248(3) . ? C7 C8 1.361(4) . ? C7 H7 0.9500 . ? C8 N9 1.391(4) . ? C8 C18 1.492(4) . ? N9 H9 0.875(17) . ? O11 C13 1.234(3) . ? N12 C13 1.372(4) . ? N12 H12 0.870(17) . ? C13 C14 1.526(4) . ? C14 C15 1.528(4) . ? C14 C16 1.530(4) . ? C14 C17 1.538(4) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.493(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 O20 1.199(4) . ? C19 O21 1.340(4) . ? O21 C22 1.441(4) . ? C22 C23 1.483(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 C2 N1 C6 124.1(3) . . ? C2 N1 H1 114(2) . . ? C6 N1 H1 122(2) . . ? N3 C2 N1 124.3(3) . . ? N3 C2 N12 117.3(3) . . ? N1 C2 N12 118.4(3) . . ? C2 N3 C4 112.8(3) . . ? N9 C4 N3 124.9(3) . . ? N9 C4 C5 107.7(3) . . ? N3 C4 C5 127.5(3) . . ? C4 C5 C6 118.2(3) . . ? C4 C5 C7 107.7(3) . . ? C6 C5 C7 134.0(3) . . ? O10 C6 N1 119.1(3) . . ? O10 C6 C5 127.9(3) . . ? N1 C6 C5 113.0(3) . . ? C8 C7 C5 107.1(3) . . ? C8 C7 H7 126.5 . . ? C5 C7 H7 126.5 . . ? C7 C8 N9 108.4(3) . . ? C7 C8 C18 130.9(3) . . ? N9 C8 C18 120.7(3) . . ? C4 N9 C8 109.2(3) . . ? C4 N9 H9 127(2) . . ? C8 N9 H9 123(2) . . ? C13 N12 C2 127.8(3) . . ? C13 N12 H12 121(2) . . ? C2 N12 H12 112(2) . . ? O11 C13 N12 121.1(3) . . ? O11 C13 C14 122.9(3) . . ? N12 C13 C14 116.1(3) . . ? C13 C14 C15 108.2(3) . . ? C13 C14 C16 110.4(3) . . ? C15 C14 C16 109.8(2) . . ? C13 C14 C17 108.9(2) . . ? C15 C14 C17 108.8(3) . . ? C16 C14 C17 110.6(3) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C8 C18 C19 114.8(3) . . ? C8 C18 H18A 108.6 . . ? C19 C18 H18A 108.6 . . ? C8 C18 H18B 108.6 . . ? C19 C18 H18B 108.6 . . ? H18A C18 H18B 107.5 . . ? O20 C19 O21 122.9(3) . . ? O20 C19 C18 126.3(3) . . ? O21 C19 C18 110.8(3) . . ? C19 O21 C22 117.3(3) . . ? O21 C22 C23 107.5(3) . . ? O21 C22 H22A 110.2 . . ? C23 C22 H22A 110.2 . . ? O21 C22 H22B 110.2 . . ? C23 C22 H22B 110.2 . . ? H22A C22 H22B 108.5 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C6 N1 C2 N3 0.3(5) . . . . ? C6 N1 C2 N12 -178.6(3) . . . . ? N1 C2 N3 C4 -0.6(4) . . . . ? N12 C2 N3 C4 178.4(3) . . . . ? C2 N3 C4 N9 179.0(3) . . . . ? C2 N3 C4 C5 -1.5(4) . . . . ? N9 C4 C5 C6 -176.7(3) . . . . ? N3 C4 C5 C6 3.7(5) . . . . ? N9 C4 C5 C7 -0.2(3) . . . . ? N3 C4 C5 C7 -179.8(3) . . . . ? C2 N1 C6 O10 -177.1(3) . . . . ? C2 N1 C6 C5 1.8(4) . . . . ? C4 C5 C6 O10 175.3(3) . . . . ? C7 C5 C6 O10 0.0(6) . . . . ? C4 C5 C6 N1 -3.5(4) . . . . ? C7 C5 C6 N1 -178.8(3) . . . . ? C4 C5 C7 C8 0.3(3) . . . . ? C6 C5 C7 C8 176.0(3) . . . . ? C5 C7 C8 N9 -0.3(3) . . . . ? C5 C7 C8 C18 -178.4(3) . . . . ? N3 C4 N9 C8 179.7(3) . . . . ? C5 C4 N9 C8 0.0(3) . . . . ? C7 C8 N9 C4 0.2(3) . . . . ? C18 C8 N9 C4 178.5(3) . . . . ? N3 C2 N12 C13 -176.0(3) . . . . ? N1 C2 N12 C13 3.0(5) . . . . ? C2 N12 C13 O11 -3.2(5) . . . . ? C2 N12 C13 C14 175.8(3) . . . . ? O11 C13 C14 C15 -1.7(4) . . . . ? N12 C13 C14 C15 179.3(3) . . . . ? O11 C13 C14 C16 -122.0(3) . . . . ? N12 C13 C14 C16 59.1(3) . . . . ? O11 C13 C14 C17 116.4(3) . . . . ? N12 C13 C14 C17 -62.6(3) . . . . ? C7 C8 C18 C19 68.4(4) . . . . ? N9 C8 C18 C19 -109.5(3) . . . . ? C8 C18 C19 O20 -23.7(5) . . . . ? C8 C18 C19 O21 158.2(3) . . . . ? O20 C19 O21 C22 1.1(5) . . . . ? C18 C19 O21 C22 179.3(3) . . . . ? C19 O21 C22 C23 -179.1(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 N1 H1 O11 0.888(17) 1.92(2) 2.649(3) 138(3) . N9 H9 O11 0.875(17) 2.09(2) 2.909(3) 155(3) 2_755 N12 H12 O10 0.870(17) 1.946(18) 2.816(3) 177(3) 2_755 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.41 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.222 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.052 _publ_section_references ; Bruker (2001). SAINT, SHELXTL, SMART, XCIF. Bruker AXS, Inc., Madison, Wisconsin, USA. Schneider, T.R. and Sheldrick, G.M. (2002). Acta Cryst. D58, 1772-1779. ; _publ_section_figure_captions ; Figure 1. SHELXTL (Bruker, 2001) plot showing 35% probability ellipsoids for non-H atoms and circles of arbitrary size for H atoms. ; _publ_section_exptl_prep ; Crystals were grown from ??. ; _publ_section_exptl_refinement ; Methyl H atom positions, R-CH~3~, were optimized by rotation about R-C bonds with idealized C-H, R--H and H--H distances. Amine H atom positions, surfaced in a late difference Fourier map and were refined with bond length restraints using an eeffective standard deviation of 0.03\%A. Methyl and amine H atom U's were assigned as 1.5 times U~eq~ of the carrier atom; remaining H atom U's were assigned as 1.2 times carrier U~eq~. ; _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_acknowledgements ; The Materials Chemistry Laboratory at the University of Illinois was supported in part by grants NSF CHE 95-03145 and NSF CHE 03-43032 from the National Science Foundation. ; loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 1.00 0.0700 0.00 0.00 -1.00 0.0700 0.00 1.00 0.00 0.4000 1.00 0.00 0.00 0.0200 -1.00 0.00 0.00 0.0200 0.00 -1.00 1.00 0.3200 0.00 -1.00 -1.00 0.3800