# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2002 data_global loop_ _publ_author_name 'M. Crampton' 'Thomas A. Emokpae' 'Judith A. K. Howard' 'Chukwuemeka Isanbor' 'Raju Mondal' _publ_contact_author_name 'Dr M Crampton' _publ_contact_author_address ; Chemistry Department Durham University Durham DH1 3LE UK ; _publ_contact_author_email M.R.CRAMPTON@DURHAM.AC.UK _publ_section_title ; Kinetic and equilibrium studies of sigma-adduct formation and nucleophilic substitution in the reactions of 2-phenoxy-3,5-dinitropyridine and 2-ethoxy-3,5-dinitropyridine with aliphatic amines in dipolar aprotic solvents ; data_raju242 _database_code_CSD 198285 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Ethoxyl-3,5-dinitropyridine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H7 N3 O5' _chemical_formula_weight 213.16 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)/n 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 6.4904(4) _cell_length_b 16.7850(11) _cell_length_c 8.2216(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.4540(10) _cell_angle_gamma 90.00 _cell_volume 874.60(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4987 _cell_measurement_theta_min 2.427 _cell_measurement_theta_max 28.9645 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.619 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.140 _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 120(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 'smart 1k CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9025 _diffrn_reflns_av_R_equivalents 0.0646 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 28.99 _reflns_number_total 2316 _reflns_number_gt 1979 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0464P)^2^+0.2900P] 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 2316 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.1010 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 O5 O 0.47942(13) 0.13321(5) 0.52097(10) 0.01858(19) Uani 1 1 d . . . N2 N 0.55215(16) 0.22678(6) 0.82012(13) 0.0185(2) Uani 1 1 d . . . O4 O -0.04781(15) 0.13519(6) 1.06445(12) 0.0286(2) Uani 1 1 d . . . O1 O 0.70101(13) 0.22458(5) 0.75054(12) 0.0237(2) Uani 1 1 d . . . O3 O -0.20862(14) 0.04454(6) 0.89654(12) 0.0256(2) Uani 1 1 d . . . N1 N 0.19957(15) 0.06847(6) 0.58920(12) 0.0181(2) Uani 1 1 d . . . N3 N -0.06835(16) 0.09440(6) 0.93861(12) 0.0194(2) Uani 1 1 d . . . C2 C 0.38045(17) 0.16908(6) 0.77228(14) 0.0160(2) Uani 1 1 d . . . C4 C 0.08208(17) 0.10555(7) 0.83244(14) 0.0170(2) Uani 1 1 d . . . O2 O 0.53819(15) 0.27393(6) 0.93101(13) 0.0299(2) Uani 1 1 d . . . C3 C 0.24064(18) 0.16170(7) 0.87550(14) 0.0170(2) Uani 1 1 d . . . C5 C 0.06690(18) 0.05958(7) 0.69121(15) 0.0185(2) Uani 1 1 d . . . C1 C 0.35321(17) 0.12264(7) 0.62525(14) 0.0155(2) Uani 1 1 d . . . C6 C 0.42438(19) 0.09208(7) 0.36097(15) 0.0189(2) Uani 1 1 d . . . C7 C 0.5858(2) 0.11673(8) 0.26465(17) 0.0243(3) Uani 1 1 d . . . H6A H 0.426(2) 0.0357(9) 0.3817(19) 0.021(4) Uiso 1 1 d . . . H6B H 0.281(2) 0.1087(9) 0.3068(18) 0.017(3) Uiso 1 1 d . . . H3 H 0.251(2) 0.1949(10) 0.970(2) 0.025(4) Uiso 1 1 d . . . H5 H -0.038(2) 0.0203(10) 0.662(2) 0.025(4) Uiso 1 1 d . . . H7A H 0.562(3) 0.0867(10) 0.161(2) 0.033(4) Uiso 1 1 d . . . H7B H 0.573(3) 0.1728(11) 0.234(2) 0.028(4) Uiso 1 1 d . . . H7C H 0.727(3) 0.1026(12) 0.330(2) 0.037(5) 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 O5 0.0189(4) 0.0218(4) 0.0165(4) -0.0022(3) 0.0071(3) -0.0023(3) N2 0.0179(4) 0.0172(4) 0.0195(5) 0.0001(4) 0.0020(4) -0.0018(4) O4 0.0304(5) 0.0373(6) 0.0213(5) -0.0091(4) 0.0129(4) -0.0058(4) O1 0.0191(4) 0.0260(5) 0.0270(5) -0.0003(4) 0.0070(4) -0.0046(3) O3 0.0232(4) 0.0283(5) 0.0274(5) -0.0021(4) 0.0102(4) -0.0078(4) N1 0.0206(5) 0.0166(4) 0.0178(5) -0.0018(4) 0.0056(4) -0.0014(4) N3 0.0195(5) 0.0224(5) 0.0172(5) 0.0007(4) 0.0062(4) 0.0001(4) C2 0.0158(5) 0.0148(5) 0.0168(5) 0.0006(4) 0.0024(4) -0.0009(4) C4 0.0173(5) 0.0180(5) 0.0168(5) 0.0015(4) 0.0061(4) 0.0007(4) O2 0.0303(5) 0.0293(5) 0.0313(5) -0.0145(4) 0.0091(4) -0.0097(4) C3 0.0188(5) 0.0171(5) 0.0146(5) -0.0010(4) 0.0025(4) 0.0013(4) C5 0.0197(5) 0.0170(5) 0.0189(5) -0.0006(4) 0.0046(4) -0.0025(4) C1 0.0164(5) 0.0144(5) 0.0163(5) 0.0015(4) 0.0045(4) 0.0024(4) C6 0.0217(6) 0.0203(6) 0.0157(5) -0.0015(4) 0.0060(4) 0.0001(4) C7 0.0263(6) 0.0290(6) 0.0201(6) 0.0006(5) 0.0106(5) -0.0008(5) _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 O5 C1 1.3193(13) . ? O5 C6 1.4601(14) . ? N2 O1 1.2250(13) . ? N2 O2 1.2253(14) . ? N2 C2 1.4647(14) . ? O4 N3 1.2237(13) . ? O3 N3 1.2301(13) . ? N1 C5 1.3337(15) . ? N1 C1 1.3347(15) . ? N3 C4 1.4552(14) . ? C2 C3 1.3752(16) . ? C2 C1 1.4171(16) . ? C4 C5 1.3798(16) . ? C4 C3 1.3840(16) . ? C6 C7 1.5011(17) . ? 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 O5 C6 117.15(9) . . ? O1 N2 O2 124.01(10) . . ? O1 N2 C2 119.05(10) . . ? O2 N2 C2 116.92(10) . . ? C5 N1 C1 119.29(10) . . ? O4 N3 O3 123.88(10) . . ? O4 N3 C4 118.06(10) . . ? O3 N3 C4 118.07(10) . . ? C3 C2 C1 119.95(10) . . ? C3 C2 N2 117.32(10) . . ? C1 C2 N2 122.72(10) . . ? C5 C4 C3 120.68(11) . . ? C5 C4 N3 119.83(10) . . ? C3 C4 N3 119.49(10) . . ? C2 C3 C4 117.18(11) . . ? N1 C5 C4 121.88(11) . . ? O5 C1 N1 119.09(10) . . ? O5 C1 C2 119.97(10) . . ? N1 C1 C2 120.93(10) . . ? O5 C6 C7 106.38(10) . . ? 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 N2 C2 C3 166.28(10) . . . . ? O2 N2 C2 C3 -12.52(15) . . . . ? O1 N2 C2 C1 -14.61(16) . . . . ? O2 N2 C2 C1 166.58(11) . . . . ? O4 N3 C4 C5 178.69(11) . . . . ? O3 N3 C4 C5 -1.31(16) . . . . ? O4 N3 C4 C3 -0.58(16) . . . . ? O3 N3 C4 C3 179.42(10) . . . . ? C1 C2 C3 C4 2.63(16) . . . . ? N2 C2 C3 C4 -178.24(10) . . . . ? C5 C4 C3 C2 -0.18(17) . . . . ? N3 C4 C3 C2 179.08(10) . . . . ? C1 N1 C5 C4 0.81(17) . . . . ? C3 C4 C5 N1 -1.62(18) . . . . ? N3 C4 C5 N1 179.12(10) . . . . ? C6 O5 C1 N1 8.04(15) . . . . ? C6 O5 C1 C2 -171.30(10) . . . . ? C5 N1 C1 O5 -177.60(10) . . . . ? C5 N1 C1 C2 1.73(16) . . . . ? C3 C2 C1 O5 175.81(10) . . . . ? N2 C2 C1 O5 -3.28(16) . . . . ? C3 C2 C1 N1 -3.52(16) . . . . ? N2 C2 C1 N1 177.40(10) . . . . ? C1 O5 C6 C7 177.61(10) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.296 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.050 data_sad _database_code_CSD 198286 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Piperidine-3,5-dinitropyridine ; _chemical_name_common NPIP _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 N4 O4' _chemical_formula_weight 252.24 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.9847(12) _cell_length_b 7.3833(15) _cell_length_c 12.375(3) _cell_angle_alpha 94.29(3) _cell_angle_beta 95.28(3) _cell_angle_gamma 91.80(3) _cell_volume 542.53(19) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2836 _cell_measurement_theta_min 3.1145 _cell_measurement_theta_max 27.4825 _exptl_crystal_description Cube _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.776709 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int) = 0.0301 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'smart 6k CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4225 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2484 _reflns_number_gt 2245 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0557P)^2^+0.1288P] 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 2484 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0361 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0963 _refine_ls_wR_factor_gt 0.0935 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 O4 O 0.22320(14) 0.13842(12) 0.00238(7) 0.0268(2) Uani 1 1 d . . . O2 O 0.14441(14) 0.26952(12) -0.37638(7) 0.0264(2) Uani 1 1 d . . . O3 O -0.02275(14) 0.24227(12) 0.10767(6) 0.0254(2) Uani 1 1 d . . . O1 O -0.19528(14) 0.31833(11) -0.44237(6) 0.0239(2) Uani 1 1 d . . . N3 N 0.05032(15) 0.21926(12) 0.01795(7) 0.0191(2) Uani 1 1 d . . . N2 N -0.04787(15) 0.31769(12) -0.36594(7) 0.0183(2) Uani 1 1 d . . . N4 N -0.38724(14) 0.59464(12) -0.29710(7) 0.0168(2) Uani 1 1 d . . . N1 N -0.39735(15) 0.44419(12) -0.14077(7) 0.0190(2) Uani 1 1 d . . . C4 C -0.07251(17) 0.29405(14) -0.07314(8) 0.0172(2) Uani 1 1 d . . . C5 C -0.28706(18) 0.36070(14) -0.06326(9) 0.0187(2) Uani 1 1 d . . . C6 C -0.61065(17) 0.66767(15) -0.28308(9) 0.0181(2) Uani 1 1 d . . . C3 C 0.01294(17) 0.28740(14) -0.17342(9) 0.0168(2) Uani 1 1 d . . . C2 C -0.10750(17) 0.36631(13) -0.25637(8) 0.0159(2) Uani 1 1 d . . . C10 C -0.26700(18) 0.68067(14) -0.37947(9) 0.0185(2) Uani 1 1 d . . . C1 C -0.30020(17) 0.47030(13) -0.23458(8) 0.0158(2) Uani 1 1 d . . . C9 C -0.25344(18) 0.88743(14) -0.35607(9) 0.0197(2) Uani 1 1 d . . . C8 C -0.48353(18) 0.96536(15) -0.34429(10) 0.0214(2) Uani 1 1 d . . . C7 C -0.59535(18) 0.87264(15) -0.25617(9) 0.0211(2) Uani 1 1 d . . . H10A H -0.115(2) 0.6374(19) -0.3778(11) 0.023(3) Uiso 1 1 d . . . H3 H 0.144(2) 0.226(2) -0.1851(11) 0.024(3) Uiso 1 1 d . . . H8A H -0.579(2) 0.942(2) -0.4137(12) 0.025(3) Uiso 1 1 d . . . H6A H -0.677(2) 0.6002(19) -0.2284(12) 0.024(3) Uiso 1 1 d . . . H10B H -0.347(2) 0.642(2) -0.4534(12) 0.025(3) Uiso 1 1 d . . . H6B H -0.703(2) 0.6404(19) -0.3533(12) 0.021(3) Uiso 1 1 d . . . H7A H -0.749(2) 0.9141(19) -0.2501(12) 0.025(3) Uiso 1 1 d . . . H7B H -0.511(2) 0.9044(19) -0.1834(12) 0.022(3) Uiso 1 1 d . . . H5 H -0.360(2) 0.3440(19) 0.0015(12) 0.025(4) Uiso 1 1 d . . . H9A H -0.157(2) 0.9213(19) -0.2853(12) 0.022(3) Uiso 1 1 d . . . H9B H -0.183(2) 0.9383(18) -0.4157(11) 0.020(3) Uiso 1 1 d . . . H8B H -0.470(2) 1.097(2) -0.3230(12) 0.027(4) 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 O4 0.0238(4) 0.0304(4) 0.0266(4) 0.0054(3) 0.0002(3) 0.0080(3) O2 0.0271(4) 0.0308(4) 0.0236(4) 0.0026(3) 0.0106(3) 0.0102(3) O3 0.0292(4) 0.0315(4) 0.0160(4) 0.0036(3) 0.0026(3) 0.0006(3) O1 0.0308(4) 0.0235(4) 0.0164(4) 0.0001(3) -0.0012(3) 0.0005(3) N3 0.0203(4) 0.0186(4) 0.0181(4) 0.0024(3) 0.0001(3) -0.0009(3) N2 0.0237(4) 0.0151(4) 0.0167(4) 0.0013(3) 0.0048(3) 0.0011(3) N4 0.0154(4) 0.0175(4) 0.0182(4) 0.0035(3) 0.0040(3) 0.0016(3) N1 0.0186(4) 0.0204(4) 0.0187(5) 0.0035(3) 0.0043(3) 0.0024(3) C4 0.0196(5) 0.0158(5) 0.0160(5) 0.0017(4) 0.0003(4) 0.0000(4) C5 0.0210(5) 0.0194(5) 0.0163(5) 0.0021(4) 0.0044(4) 0.0004(4) C6 0.0140(5) 0.0212(5) 0.0199(5) 0.0047(4) 0.0022(4) 0.0018(4) C3 0.0167(5) 0.0145(5) 0.0190(5) -0.0005(4) 0.0026(4) 0.0010(4) C2 0.0180(5) 0.0147(5) 0.0153(5) -0.0003(4) 0.0041(4) -0.0002(4) C10 0.0192(5) 0.0178(5) 0.0199(5) 0.0045(4) 0.0066(4) 0.0019(4) C1 0.0154(5) 0.0154(5) 0.0163(5) 0.0003(4) 0.0012(4) -0.0017(4) C9 0.0187(5) 0.0174(5) 0.0236(5) 0.0035(4) 0.0029(4) -0.0001(4) C8 0.0199(5) 0.0169(5) 0.0275(6) 0.0035(4) 0.0012(4) 0.0018(4) C7 0.0174(5) 0.0211(5) 0.0251(6) 0.0007(4) 0.0035(4) 0.0041(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 O4 N3 1.2337(13) . ? O2 N2 1.2303(13) . ? O3 N3 1.2323(13) . ? O1 N2 1.2329(13) . ? N3 C4 1.4429(14) . ? N2 C2 1.4556(13) . ? N4 C1 1.3322(14) . ? N4 C10 1.4709(13) . ? N4 C6 1.4773(13) . ? N1 C5 1.3164(15) . ? N1 C1 1.3688(14) . ? C4 C3 1.3832(15) . ? C4 C5 1.4019(15) . ? C6 C7 1.5231(15) . ? C3 C2 1.3756(15) . ? C2 C1 1.4402(14) . ? C10 C9 1.5305(15) . ? C9 C8 1.5240(15) . ? C8 C7 1.5241(16) . ? 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 O3 N3 O4 123.68(9) . . ? O3 N3 C4 117.69(9) . . ? O4 N3 C4 118.62(9) . . ? O2 N2 O1 123.63(9) . . ? O2 N2 C2 117.93(9) . . ? O1 N2 C2 118.34(9) . . ? C1 N4 C10 124.00(9) . . y C1 N4 C6 121.80(9) . . y C10 N4 C6 114.06(8) . . ? C5 N1 C1 119.58(9) . . ? C3 C4 C5 119.29(10) . . ? C3 C4 N3 120.13(10) . . ? C5 C4 N3 120.38(10) . . ? N1 C5 C4 122.54(10) . . ? N4 C6 C7 111.37(9) . . ? C2 C3 C4 117.63(10) . . ? C3 C2 C1 120.20(9) . . ? C3 C2 N2 116.26(9) . . y C1 C2 N2 123.01(9) . . y N4 C10 C9 110.49(9) . . ? N4 C1 N1 117.26(9) . . y N4 C1 C2 124.97(9) . . y N1 C1 C2 117.73(9) . . ? C8 C9 C10 112.16(9) . . ? C9 C8 C7 109.54(9) . . ? C6 C7 C8 110.04(9) . . ? 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 O3 N3 C4 C3 173.87(9) . . . . y O4 N3 C4 C3 -5.17(15) . . . . y O3 N3 C4 C5 -11.26(14) . . . . y O4 N3 C4 C5 169.70(9) . . . . y C1 N1 C5 C4 -0.90(16) . . . . ? C3 C4 C5 N1 -11.08(16) . . . . ? N3 C4 C5 N1 174.01(10) . . . . ? C1 N4 C6 C7 120.04(11) . . . . ? C10 N4 C6 C7 -55.80(12) . . . . ? C5 C4 C3 C2 7.25(15) . . . . ? N3 C4 C3 C2 -177.82(9) . . . . ? C4 C3 C2 C1 7.30(14) . . . . ? C4 C3 C2 N2 -164.58(9) . . . . ? O2 N2 C2 C3 -25.98(13) . . . . y O1 N2 C2 C3 150.49(10) . . . . y O2 N2 C2 C1 162.38(9) . . . . y O1 N2 C2 C1 -21.15(14) . . . . y C1 N4 C10 C9 -122.34(11) . . . . ? C6 N4 C10 C9 53.40(12) . . . . ? C10 N4 C1 N1 159.95(9) . . . . ? C6 N4 C1 N1 -15.47(14) . . . . ? C10 N4 C1 C2 -17.77(16) . . . . ? C6 N4 C1 C2 166.81(9) . . . . ? C5 N1 C1 N4 -162.47(10) . . . . ? C5 N1 C1 C2 15.42(14) . . . . ? C3 C2 C1 N4 158.80(10) . . . . ? N2 C2 C1 N4 -29.88(15) . . . . ? C3 C2 C1 N1 -18.92(14) . . . . ? N2 C2 C1 N1 152.40(9) . . . . ? N4 C10 C9 C8 -53.48(12) . . . . ? C10 C9 C8 C7 55.81(12) . . . . ? N4 C6 C7 C8 56.46(12) . . . . ? C9 C8 C7 C6 -56.54(12) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.317 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.047