# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Andreas Schmidt' 'Abbas Gholipour Shilabin' 'Martin Nieger' _publ_contact_author_name 'Dr Andreas Schmidt' _publ_contact_author_address ; Institute of Organic Chemistry Technical University of Clausthal Leibnizstrasse 6 Clausthal-Zellerfeld D-38678 GERMANY ; _publ_contact_author_email SCHMIDT@IOC.TU-CLAUSTHAL.DE _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; On Benzo[b][1,4]diazepinium-olates, -thiolates and -carboxylates as Anti-Huckel Mesomeric Betaines ; #============================================================================== data_schm13_AB-2 _database_code_CSD 216056 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7-Carboxy-2,4-dimethyl-5H-benzo[b][1,4]diazepin-ium picrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C12 H13 N2 O2)+ (C6 H2 N3 O7)- MeOH' _chemical_formula_sum 'C19 H19 N5 O10' _chemical_formula_weight 477.39 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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8117(2) _cell_length_b 11.0726(2) _cell_length_c 11.2477(3) _cell_angle_alpha 79.339(1) _cell_angle_beta 73.059(1) _cell_angle_gamma 86.946(1) _cell_volume 1031.68(4) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4569 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plates _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 40 mm, 60 sec./deg., 2 deg., 9 sets, 410 frames, mos.= 0.649(2) deg. ; _diffrn_ambient_temperature 123(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 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 2 deg,' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 17842 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3648 _reflns_number_gt 3035 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-NT _computing_publication_material 'SHELXL-97 (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^)+(0.0667P)^2^+0.4235P] 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 3648 _refine_ls_number_parameters 322 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1218 _refine_ls_wR_factor_gt 0.1165 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.69336(18) 0.65468(14) 1.00103(15) 0.0226(4) Uani 1 1 d D . . H1N H 0.712(2) 0.6798(19) 1.0634(17) 0.027 Uiso 1 1 d D . . C2 C 0.6341(2) 0.73837(16) 0.92494(17) 0.0219(4) Uani 1 1 d . . . C3 C 0.5910(2) 0.72125(17) 0.82031(18) 0.0256(4) Uani 1 1 d . . . H3 H 0.5580 0.7936 0.7744 0.031 Uiso 1 1 calc R . . C4 C 0.5884(2) 0.61467(16) 0.77161(17) 0.0211(4) Uani 1 1 d . . . N5 N 0.63665(17) 0.50389(14) 0.81290(15) 0.0220(3) Uani 1 1 d D . . H5N H 0.625(2) 0.4477(17) 0.7738(19) 0.026 Uiso 1 1 d D . . C6 C 0.7158(2) 0.46251(16) 0.90699(16) 0.0195(4) Uani 1 1 d . . . C7 C 0.7730(2) 0.34344(16) 0.91057(16) 0.0206(4) Uani 1 1 d . . . H7 H 0.7588 0.2975 0.8512 0.025 Uiso 1 1 calc R . . C8 C 0.8508(2) 0.28875(16) 0.99858(17) 0.0213(4) Uani 1 1 d . . . C9 C 0.8678(2) 0.35438(16) 1.08756(17) 0.0227(4) Uani 1 1 d . . . H9 H 0.9168 0.3178 1.1504 0.027 Uiso 1 1 calc R . . C10 C 0.8123(2) 0.47415(17) 1.08362(17) 0.0218(4) Uani 1 1 d . . . H10 H 0.8252 0.5192 1.1442 0.026 Uiso 1 1 calc R . . C11 C 0.7386(2) 0.53056(16) 0.99454(16) 0.0192(4) Uani 1 1 d . . . C12 C 0.9172(2) 0.16247(16) 0.99662(17) 0.0223(4) Uani 1 1 d . . . O1 O 0.88962(17) 0.10681(12) 0.91274(13) 0.0295(3) Uani 1 1 d D . . H1O H 0.930(3) 0.0326(17) 0.917(2) 0.044 Uiso 1 1 d D . . O2 O 0.99385(17) 0.11785(12) 1.07021(13) 0.0334(4) Uani 1 1 d . . . C13 C 0.6091(2) 0.86242(17) 0.9615(2) 0.0293(4) Uani 1 1 d . . . H13A H 0.4958 0.8824 0.9826 0.044 Uiso 1 1 calc R . . H13B H 0.6679 0.9239 0.8909 0.044 Uiso 1 1 calc R . . H13C H 0.6474 0.8624 1.0351 0.044 Uiso 1 1 calc R . . C14 C 0.5222(2) 0.62325(17) 0.66138(18) 0.0272(4) Uani 1 1 d . . . H14A H 0.5795 0.5665 0.6064 0.041 Uiso 1 1 calc R . . H14B H 0.5346 0.7074 0.6136 0.041 Uiso 1 1 calc R . . H14C H 0.4094 0.6015 0.6922 0.041 Uiso 1 1 calc R . . C1' C 0.2145(2) 0.22624(17) 0.68158(17) 0.0227(4) Uani 1 1 d . . . C2' C 0.1254(2) 0.30147(16) 0.60631(17) 0.0215(4) Uani 1 1 d . . . C3' C 0.0800(2) 0.26806(17) 0.51056(17) 0.0235(4) Uani 1 1 d . . . H3' H 0.0161 0.3209 0.4683 0.028 Uiso 1 1 calc R . . C4' C 0.1297(2) 0.15501(17) 0.47688(17) 0.0235(4) Uani 1 1 d . . . C5' C 0.2180(2) 0.07653(17) 0.54016(18) 0.0247(4) Uani 1 1 d . . . H5' H 0.2531 0.0002 0.5147 0.030 Uiso 1 1 calc R . . C6' C 0.2554(2) 0.10908(17) 0.64094(18) 0.0240(4) Uani 1 1 d . . . O1' O 0.25085(16) 0.26135(12) 0.77049(12) 0.0282(3) Uani 1 1 d . . . N2' N 0.0811(2) 0.42547(15) 0.63025(14) 0.0286(4) Uani 1 1 d . . . O21' O -0.05665(18) 0.45826(13) 0.63717(13) 0.0373(4) Uani 1 1 d . . . O22' O 0.1833(2) 0.49179(13) 0.63863(15) 0.0446(4) Uani 1 1 d . . . N4' N 0.0835(2) 0.11913(15) 0.37492(16) 0.0312(4) Uani 1 1 d . . . O41' O 0.13966(18) 0.02428(13) 0.33735(14) 0.0372(4) Uani 1 1 d . . . O42' O -0.0132(2) 0.18425(15) 0.33261(16) 0.0533(5) Uani 1 1 d . . . N6' N 0.3419(2) 0.01713(15) 0.70550(16) 0.0305(4) Uani 1 1 d . . . O61' O 0.3379(2) 0.02060(15) 0.81423(16) 0.0554(5) Uani 1 1 d . . . O62' O 0.4124(2) -0.06344(17) 0.65045(17) 0.0633(6) Uani 1 1 d . . . O1E O 0.56690(18) 0.31250(15) 0.70665(17) 0.0457(4) Uani 1 1 d D . . H1E H 0.470(2) 0.300(3) 0.724(3) 0.068 Uiso 1 1 d D . . C1E C 0.6578(3) 0.2311(3) 0.6353(3) 0.0669(9) Uani 1 1 d . . . H1E1 H 0.7703 0.2447 0.6245 0.100 Uiso 1 1 calc R . . H1E2 H 0.6385 0.2443 0.5523 0.100 Uiso 1 1 calc R . . H1E3 H 0.6288 0.1466 0.6784 0.100 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 0.0282(8) 0.0199(8) 0.0240(8) -0.0082(7) -0.0125(7) 0.0055(6) C2 0.0209(9) 0.0197(9) 0.0236(9) -0.0033(8) -0.0045(8) 0.0017(7) C3 0.0336(10) 0.0193(9) 0.0255(10) -0.0007(8) -0.0136(8) 0.0040(8) C4 0.0179(9) 0.0231(9) 0.0210(9) -0.0032(7) -0.0046(7) 0.0026(7) N5 0.0247(8) 0.0206(8) 0.0259(8) -0.0092(7) -0.0128(7) 0.0050(6) C6 0.0176(8) 0.0220(9) 0.0186(9) -0.0039(7) -0.0044(7) 0.0012(7) C7 0.0221(9) 0.0191(9) 0.0201(9) -0.0051(7) -0.0045(7) 0.0001(7) C8 0.0210(9) 0.0204(9) 0.0205(9) -0.0018(7) -0.0041(7) 0.0009(7) C9 0.0257(10) 0.0219(9) 0.0206(9) -0.0017(7) -0.0085(8) 0.0024(7) C10 0.0245(9) 0.0229(9) 0.0196(9) -0.0060(7) -0.0075(8) 0.0011(7) C11 0.0176(8) 0.0184(9) 0.0205(9) -0.0041(7) -0.0034(7) 0.0009(7) C12 0.0260(10) 0.0204(9) 0.0215(9) -0.0041(8) -0.0086(8) 0.0025(7) O1 0.0412(8) 0.0204(7) 0.0326(8) -0.0094(6) -0.0176(6) 0.0079(6) O2 0.0462(9) 0.0266(7) 0.0348(8) -0.0099(6) -0.0227(7) 0.0142(6) C13 0.0390(11) 0.0199(9) 0.0333(11) -0.0067(8) -0.0165(9) 0.0054(8) C14 0.0310(10) 0.0264(10) 0.0267(10) -0.0041(8) -0.0129(8) 0.0031(8) C1' 0.0196(9) 0.0263(10) 0.0207(9) -0.0027(8) -0.0041(7) -0.0019(7) C2' 0.0223(9) 0.0197(9) 0.0212(9) -0.0031(7) -0.0049(7) 0.0016(7) C3' 0.0252(9) 0.0221(9) 0.0225(9) -0.0007(8) -0.0080(8) 0.0023(7) C4' 0.0272(10) 0.0237(9) 0.0211(9) -0.0043(8) -0.0090(8) -0.0004(8) C5' 0.0268(10) 0.0208(9) 0.0260(10) -0.0041(8) -0.0070(8) 0.0017(8) C6' 0.0228(9) 0.0237(9) 0.0251(10) -0.0013(8) -0.0087(8) 0.0024(7) O1' 0.0325(7) 0.0319(7) 0.0253(7) -0.0087(6) -0.0142(6) 0.0034(6) N2' 0.0443(11) 0.0240(8) 0.0173(8) -0.0029(7) -0.0096(7) 0.0037(8) O21' 0.0410(9) 0.0318(8) 0.0291(8) -0.0015(6) 0.0002(6) 0.0153(7) O22' 0.0717(11) 0.0270(8) 0.0472(10) -0.0073(7) -0.0349(9) -0.0045(8) N4' 0.0449(10) 0.0251(9) 0.0279(9) -0.0049(7) -0.0172(8) 0.0019(8) O41' 0.0537(9) 0.0273(7) 0.0361(8) -0.0134(6) -0.0170(7) 0.0027(7) O42' 0.0874(13) 0.0414(9) 0.0527(11) -0.0151(8) -0.0528(10) 0.0203(9) N6' 0.0348(9) 0.0267(9) 0.0336(10) -0.0027(7) -0.0179(8) 0.0037(7) O61' 0.0920(14) 0.0427(10) 0.0496(11) -0.0113(8) -0.0493(10) 0.0183(9) O62' 0.0899(14) 0.0554(11) 0.0550(11) -0.0218(9) -0.0382(10) 0.0497(11) O1E 0.0310(8) 0.0496(10) 0.0688(11) -0.0389(9) -0.0168(8) 0.0044(7) C1E 0.0381(14) 0.0746(19) 0.101(2) -0.0643(19) -0.0104(14) 0.0012(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.334(2) . ? N1 C11 1.419(2) . ? N1 H1N 0.861(15) . ? C2 C3 1.384(3) . ? C2 C13 1.493(2) . ? C3 C4 1.394(3) . ? C3 H3 0.9500 . ? C4 N5 1.323(2) . ? C4 C14 1.503(2) . ? N5 C6 1.426(2) . ? N5 H5N 0.851(15) . ? C6 C7 1.384(2) . ? C6 C11 1.409(2) . ? C7 C8 1.395(3) . ? C7 H7 0.9500 . ? C8 C9 1.386(2) . ? C8 C12 1.488(2) . ? C9 C10 1.386(3) . ? C9 H9 0.9500 . ? C10 C11 1.385(3) . ? C10 H10 0.9500 . ? C12 O2 1.235(2) . ? C12 O1 1.301(2) . ? O1 H1O 0.878(16) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C1' O1' 1.264(2) . ? C1' C2' 1.443(3) . ? C1' C6' 1.447(3) . ? C2' C3' 1.368(3) . ? C2' N2' 1.459(2) . ? C3' C4' 1.387(3) . ? C3' H3' 0.9500 . ? C4' C5' 1.374(3) . ? C4' N4' 1.448(2) . ? C5' C6' 1.380(3) . ? C5' H5' 0.9500 . ? C6' N6' 1.453(2) . ? N2' O22' 1.227(2) . ? N2' O21' 1.233(2) . ? N4' O41' 1.230(2) . ? N4' O42' 1.232(2) . ? N6' O62' 1.219(2) . ? N6' O61' 1.221(2) . ? O1E C1E 1.384(3) . ? O1E H1E 0.836(17) . ? C1E H1E1 0.9800 . ? C1E H1E2 0.9800 . ? C1E H1E3 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 C11 131.11(15) . . ? C2 N1 H1N 115.8(14) . . ? C11 N1 H1N 113.0(14) . . ? N1 C2 C3 127.28(16) . . ? N1 C2 C13 114.70(16) . . ? C3 C2 C13 118.00(16) . . ? C2 C3 C4 130.23(17) . . ? C2 C3 H3 114.9 . . ? C4 C3 H3 114.9 . . ? N5 C4 C3 127.01(17) . . ? N5 C4 C14 115.10(15) . . ? C3 C4 C14 117.89(16) . . ? C4 N5 C6 131.11(15) . . ? C4 N5 H5N 115.7(14) . . ? C6 N5 H5N 113.0(14) . . ? C7 C6 C11 118.61(16) . . ? C7 C6 N5 115.16(15) . . ? C11 C6 N5 126.23(16) . . ? C6 C7 C8 122.13(16) . . ? C6 C7 H7 118.9 . . ? C8 C7 H7 118.9 . . ? C9 C8 C7 119.08(16) . . ? C9 C8 C12 120.00(16) . . ? C7 C8 C12 120.92(16) . . ? C8 C9 C10 119.04(17) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C11 C10 C9 122.38(16) . . ? C11 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? C10 C11 C6 118.70(16) . . ? C10 C11 N1 115.28(15) . . ? C6 C11 N1 126.02(16) . . ? O2 C12 O1 124.43(16) . . ? O2 C12 C8 120.29(15) . . ? O1 C12 C8 115.27(15) . . ? C12 O1 H1O 111.1(16) . . ? C2 C13 H13A 109.5 . . ? C2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C4 C14 H14A 109.5 . . ? C4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O1' C1' C2' 122.89(17) . . ? O1' C1' C6' 125.84(17) . . ? C2' C1' C6' 111.27(16) . . ? C3' C2' C1' 125.72(16) . . ? C3' C2' N2' 115.64(16) . . ? C1' C2' N2' 118.63(15) . . ? C2' C3' C4' 118.18(17) . . ? C2' C3' H3' 120.9 . . ? C4' C3' H3' 120.9 . . ? C5' C4' C3' 121.22(17) . . ? C5' C4' N4' 120.08(16) . . ? C3' C4' N4' 118.68(16) . . ? C4' C5' C6' 119.72(17) . . ? C4' C5' H5' 120.1 . . ? C6' C5' H5' 120.1 . . ? C5' C6' C1' 123.75(17) . . ? C5' C6' N6' 115.42(16) . . ? C1' C6' N6' 120.83(16) . . ? O22' N2' O21' 123.99(17) . . ? O22' N2' C2' 118.45(17) . . ? O21' N2' C2' 117.53(16) . . ? O41' N4' O42' 123.61(16) . . ? O41' N4' C4' 118.57(16) . . ? O42' N4' C4' 117.80(16) . . ? O62' N6' O61' 121.99(17) . . ? O62' N6' C6' 118.79(16) . . ? O61' N6' C6' 119.18(16) . . ? C1E O1E H1E 113(2) . . ? O1E C1E H1E1 109.5 . . ? O1E C1E H1E2 109.5 . . ? H1E1 C1E H1E2 109.5 . . ? O1E C1E H1E3 109.5 . . ? H1E1 C1E H1E3 109.5 . . ? H1E2 C1E H1E3 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 C11 N1 C2 C3 4.6(3) . . . . ? C11 N1 C2 C13 -177.08(18) . . . . ? N1 C2 C3 C4 4.3(3) . . . . ? C13 C2 C3 C4 -173.96(19) . . . . ? C2 C3 C4 N5 -4.1(3) . . . . ? C2 C3 C4 C14 174.98(19) . . . . ? C3 C4 N5 C6 -6.4(3) . . . . ? C14 C4 N5 C6 174.49(17) . . . . ? C4 N5 C6 C7 -169.23(18) . . . . ? C4 N5 C6 C11 11.3(3) . . . . ? C11 C6 C7 C8 0.6(3) . . . . ? N5 C6 C7 C8 -178.91(16) . . . . ? C6 C7 C8 C9 1.8(3) . . . . ? C6 C7 C8 C12 -177.33(16) . . . . ? C7 C8 C9 C10 -2.4(3) . . . . ? C12 C8 C9 C10 176.71(16) . . . . ? C8 C9 C10 C11 0.7(3) . . . . ? C9 C10 C11 C6 1.7(3) . . . . ? C9 C10 C11 N1 -178.07(16) . . . . ? C7 C6 C11 C10 -2.3(2) . . . . ? N5 C6 C11 C10 177.16(16) . . . . ? C7 C6 C11 N1 177.43(16) . . . . ? N5 C6 C11 N1 -3.1(3) . . . . ? C2 N1 C11 C10 173.30(18) . . . . ? C2 N1 C11 C6 -6.5(3) . . . . ? C9 C8 C12 O2 -3.4(3) . . . . ? C7 C8 C12 O2 175.74(17) . . . . ? C9 C8 C12 O1 177.44(16) . . . . ? C7 C8 C12 O1 -3.5(3) . . . . ? O1' C1' C2' C3' -178.75(18) . . . . ? C6' C1' C2' C3' 1.6(3) . . . . ? O1' C1' C2' N2' 2.7(3) . . . . ? C6' C1' C2' N2' -176.98(15) . . . . ? C1' C2' C3' C4' -3.7(3) . . . . ? N2' C2' C3' C4' 174.97(16) . . . . ? C2' C3' C4' C5' 2.0(3) . . . . ? C2' C3' C4' N4' -179.45(16) . . . . ? C3' C4' C5' C6' 1.4(3) . . . . ? N4' C4' C5' C6' -177.08(17) . . . . ? C4' C5' C6' C1' -3.6(3) . . . . ? C4' C5' C6' N6' 176.92(16) . . . . ? O1' C1' C6' C5' -177.54(18) . . . . ? C2' C1' C6' C5' 2.1(3) . . . . ? O1' C1' C6' N6' 1.9(3) . . . . ? C2' C1' C6' N6' -178.46(16) . . . . ? C3' C2' N2' O22' -130.71(18) . . . . ? C1' C2' N2' O22' 48.0(2) . . . . ? C3' C2' N2' O21' 47.2(2) . . . . ? C1' C2' N2' O21' -134.05(17) . . . . ? C5' C4' N4' O41' -8.1(3) . . . . ? C3' C4' N4' O41' 173.34(17) . . . . ? C5' C4' N4' O42' 170.17(19) . . . . ? C3' C4' N4' O42' -8.4(3) . . . . ? C5' C6' N6' O62' 19.9(3) . . . . ? C1' C6' N6' O62' -159.6(2) . . . . ? C5' C6' N6' O61' -157.92(19) . . . . ? C1' C6' N6' O61' 22.6(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 H1N O1' 0.861(15) 2.202(16) 3.0626(19) 176.9(19) 2_667 N5 H5N O1E 0.851(15) 1.950(16) 2.793(2) 170(2) . O1 H1O O2 0.878(16) 1.758(17) 2.6354(18) 178(3) 2_757 O1E H1E O1' 0.836(17) 1.894(18) 2.728(2) 176(3) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.673 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.054 #============================================================================== #_eof # End of Crystallographic Information File