# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_address ;College of Chemistry and Molecular Sciences Wuhan University Wuhan 430072 P. R. China ; _publ_contact_author_address ;College of Chemistry and Molecular Sciences Wuhan University Wuhan 430072 P. R. China ; _publ_contact_author_email chenshuoping_777@163.com _publ_contact_author_fax 86-27-68752800 _publ_contact_author_phone 86-27-68752800 _publ_contact_author_name 'Shuoping Chen' _publ_author_name 'Shuoping Chen' # Attachment 'S-2.cif' data_61227csp3_0m _database_code_depnum_ccdc_archive 'CCDC 682746' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H9 N O6 P2' _chemical_formula_weight 205.04 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' H H 0.0000 0.0000 '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 5.5780(4) _cell_length_b 5.9177(4) _cell_length_c 11.3992(12) _cell_angle_alpha 82.368(2) _cell_angle_beta 82.198(2) _cell_angle_gamma 78.166(8) _cell_volume 362.72(5) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3176 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 29.65 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.877 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 0.586 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8123 _exptl_absorpt_correction_T_max 0.9069 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 1930 _diffrn_reflns_av_R_equivalents 0.0121 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 25.49 _reflns_number_total 1307 _reflns_number_gt 1248 _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^)+(0.0427P)^2^+0.4537P] 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 SHELXL _refine_ls_extinction_coef 0.107(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1307 _refine_ls_number_parameters 119 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0878 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.010 _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 C1 C 0.3029(4) 0.8557(4) 0.75611(18) 0.0178(4) Uani 1 1 d . . . C2 C 0.3924(4) 0.6698(4) 0.8560(2) 0.0247(5) Uani 1 1 d . . . H5A H 0.4314 0.7431 0.9193 0.037 Uiso 1 1 calc R . . H5B H 0.5368 0.5667 0.8253 0.037 Uiso 1 1 calc R . . H5C H 0.2649 0.5831 0.8858 0.037 Uiso 1 1 calc R . . H1 H 0.063(5) 0.950(9) 0.516(5) 0.042(19) Uiso 0.50 1 d PD . . H2 H -0.024(5) 0.511(2) 0.687(2) 0.027(7) Uiso 1 1 d D . . H3 H 0.477(13) 0.573(10) 0.540(2) 0.05(2) Uiso 0.50 1 d PD . . H6 H 0.163(6) 1.137(5) 0.9704(12) 0.037(8) Uiso 1 1 d D . . N1 N 0.5128(3) 0.9814(4) 0.70692(17) 0.0253(5) Uani 1 1 d . . . H6A H 0.6367 0.8829 0.6727 0.038 Uiso 1 1 calc R . . H6B H 0.5642 1.0366 0.7660 0.038 Uiso 1 1 calc R . . H6C H 0.4604 1.0983 0.6532 0.038 Uiso 1 1 calc R . . O1 O 0.2091(3) 0.9133(4) 0.52673(15) 0.0353(5) Uani 1 1 d D . . O2 O -0.0266(3) 0.6569(3) 0.67308(14) 0.0226(4) Uani 1 1 d D . . O3 O 0.4272(3) 0.5201(4) 0.60947(16) 0.0417(5) Uani 1 1 d D . . O4 O -0.0444(4) 1.2390(3) 0.7150(2) 0.0452(6) Uani 1 1 d . . . O5 O -0.1477(3) 0.9510(3) 0.88548(16) 0.0330(4) Uani 1 1 d . . . O6 O 0.1736(3) 1.1951(3) 0.89815(16) 0.0299(4) Uani 1 1 d D . . P1 P 0.22063(10) 0.72681(11) 0.63241(5) 0.0241(2) Uani 1 1 d D . . P2 P 0.04958(10) 1.07270(9) 0.81870(5) 0.0206(2) Uani 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 C1 0.0145(10) 0.0233(10) 0.0161(10) -0.0002(8) -0.0020(8) -0.0061(8) C2 0.0282(12) 0.0229(11) 0.0230(11) 0.0012(9) -0.0086(9) -0.0035(9) N1 0.0173(9) 0.0379(11) 0.0223(10) 0.0022(8) -0.0026(8) -0.0118(8) O1 0.0284(10) 0.0626(13) 0.0177(8) 0.0048(8) -0.0047(7) -0.0194(9) O2 0.0175(8) 0.0211(8) 0.0297(8) -0.0059(6) -0.0031(6) -0.0028(6) O3 0.0231(9) 0.0698(14) 0.0282(10) -0.0240(10) -0.0030(8) 0.0124(9) O4 0.0591(13) 0.0205(9) 0.0623(13) 0.0023(8) -0.0418(11) -0.0036(8) O5 0.0209(9) 0.0479(11) 0.0360(10) -0.0206(8) 0.0045(7) -0.0148(8) O6 0.0331(9) 0.0289(9) 0.0334(10) -0.0092(7) -0.0076(8) -0.0131(7) P1 0.0176(4) 0.0406(4) 0.0164(3) -0.0067(2) -0.0014(2) -0.0090(3) P2 0.0190(3) 0.0186(3) 0.0261(4) -0.0048(2) -0.0065(2) -0.0039(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 C1 N1 1.518(3) . ? C1 C2 1.534(3) . ? C1 P2 1.838(2) . ? C1 P1 1.840(2) . ? C2 H5A 0.9600 . ? C2 H5B 0.9600 . ? C2 H5C 0.9600 . ? N1 H6A 0.8900 . ? N1 H6B 0.8900 . ? N1 H6C 0.8900 . ? O1 P1 1.5205(18) . ? O1 H1 0.82(2) . ? O2 P1 1.5156(16) . ? O2 H2 0.852(10) . ? O3 P1 1.5224(19) . ? O3 H3 0.846(10) . ? O4 P2 1.5129(19) . ? O5 P2 1.5037(18) . ? O6 P2 1.5403(17) . ? O6 H6 0.847(10) . ? P1 H1 1.91(2) . ? P1 H3 1.81(6) . ? 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 N1 C1 C2 108.10(17) . . ? N1 C1 P2 106.89(14) . . ? C2 C1 P2 109.38(15) . . ? N1 C1 P1 107.46(14) . . ? C2 C1 P1 111.73(15) . . ? P2 C1 P1 113.03(11) . . ? C1 C2 H5A 109.5 . . ? C1 C2 H5B 109.5 . . ? H5A C2 H5B 109.5 . . ? C1 C2 H5C 109.5 . . ? H5A C2 H5C 109.5 . . ? H5B C2 H5C 109.5 . . ? C1 N1 H6A 109.5 . . ? C1 N1 H6B 109.5 . . ? H6A N1 H6B 109.5 . . ? C1 N1 H6C 109.5 . . ? H6A N1 H6C 109.5 . . ? H6B N1 H6C 109.5 . . ? P1 O1 H1 106(2) . . ? P1 O2 H2 115.8(19) . . ? P1 O3 H3 96(5) . . ? P2 O6 H6 113(2) . . ? O2 P1 O1 112.38(10) . . ? O2 P1 O3 112.84(11) . . ? O1 P1 O3 111.82(11) . . ? O2 P1 C1 106.99(9) . . ? O1 P1 C1 106.51(10) . . ? O3 P1 C1 105.73(10) . . ? O2 P1 H1 88.1(9) . . ? O1 P1 H1 24.4(9) . . ? O3 P1 H1 127.1(19) . . ? C1 P1 H1 114(2) . . ? O2 P1 H3 127(2) . . ? O1 P1 H3 84.2(12) . . ? O3 P1 H3 27.6(12) . . ? C1 P1 H3 116(2) . . ? H1 P1 H3 101(2) . . ? O5 P2 O4 111.70(12) . . ? O5 P2 O6 113.84(10) . . ? O4 P2 O6 110.87(10) . . ? O5 P2 C1 109.03(10) . . ? O4 P2 C1 106.82(11) . . ? O6 P2 C1 104.04(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 N1 C1 P1 O2 -165.68(13) . . . . ? C2 C1 P1 O2 75.90(16) . . . . ? P2 C1 P1 O2 -47.99(13) . . . . ? N1 C1 P1 O1 -45.29(16) . . . . ? C2 C1 P1 O1 -163.71(15) . . . . ? P2 C1 P1 O1 72.40(13) . . . . ? N1 C1 P1 O3 73.81(17) . . . . ? C2 C1 P1 O3 -44.61(18) . . . . ? P2 C1 P1 O3 -168.50(12) . . . . ? N1 C1 P2 O5 -171.26(13) . . . . ? C2 C1 P2 O5 -54.45(17) . . . . ? P1 C1 P2 O5 70.71(13) . . . . ? N1 C1 P2 O4 67.88(15) . . . . ? C2 C1 P2 O4 -175.32(14) . . . . ? P1 C1 P2 O4 -50.15(14) . . . . ? N1 C1 P2 O6 -49.47(15) . . . . ? C2 C1 P2 O6 67.34(16) . . . . ? P1 C1 P2 O6 -167.49(11) . . . . ? 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 O1 H1 O1 0.82(2) 1.668(18) 2.471(4) 165(4) 2_576 O2 H2 O4 0.852(10) 1.625(11) 2.476(2) 175(3) 1_545 O3 H3 O3 0.846(10) 1.84(4) 2.544(3) 140(6) 2_666 O6 H6 O5 0.847(10) 1.653(11) 2.498(3) 174(3) 2_577 N1 H6A O2 0.89 2.07 2.888(3) 152.4 1_655 N1 H6B O5 0.89 2.18 2.928(3) 140.7 1_655 N1 H6C O3 0.89 2.45 3.194(3) 141.0 1_565 _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.362 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.066 data_100402csp_0m _database_code_depnum_ccdc_archive 'CCDC 782031' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 N4 O6 P2' _chemical_formula_weight 324.17 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' P P 0.1023 0.0942 '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 5.4483(15) _cell_length_b 9.366(3) _cell_length_c 12.918(4) _cell_angle_alpha 94.059(4) _cell_angle_beta 95.706(4) _cell_angle_gamma 99.278(4) _cell_volume 644.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1783 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.670 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.370 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9263 _exptl_absorpt_correction_T_max 0.9569 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 3638 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2465 _reflns_number_gt 2042 _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^)+(0.1341P)^2^+0.0522P] 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 2465 _refine_ls_number_parameters 199 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1753 _refine_ls_wR_factor_gt 0.1642 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.029 _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 C1 C 0.3619(5) 0.7465(3) 0.3738(2) 0.0235(6) Uani 1 1 d . . . C2 C 0.2463(6) 0.5973(3) 0.3164(2) 0.0335(7) Uani 1 1 d . . . H2A H 0.1418 0.5427 0.3604 0.050 Uiso 1 1 calc R . . H2B H 0.3776 0.5454 0.2998 0.050 Uiso 1 1 calc R . . H2C H 0.1477 0.6109 0.2532 0.050 Uiso 1 1 calc R . . C3 C -0.0891(7) 0.8158(4) 0.8876(2) 0.0379(8) Uani 1 1 d . . . C4 C -0.0296(6) 0.7530(3) 0.9797(2) 0.0328(7) Uani 1 1 d . . . C5 C 0.1479(7) 0.6598(3) 0.9867(3) 0.0411(8) Uani 1 1 d . . . H5 H 0.1936 0.6207 1.0485 0.049 Uiso 1 1 calc R . . C6 C 0.2493(7) 0.6304(4) 0.8961(3) 0.0508(9) Uani 1 1 d . . . H6 H 0.3650 0.5675 0.8965 0.061 Uiso 1 1 calc R . . C7 C 0.1866(8) 0.6906(5) 0.8034(3) 0.0587(11) Uani 1 1 d . . . H7 H 0.2614 0.6660 0.7445 0.070 Uiso 1 1 calc R . . C8 C 0.0177(8) 0.7851(4) 0.7961(3) 0.0510(10) Uani 1 1 d . . . H8 H -0.0227 0.8260 0.7344 0.061 Uiso 1 1 calc R . . H2 H -0.311(8) 0.963(3) 0.871(3) 0.055(12) Uiso 1 1 d D . . H4 H -0.170(7) 0.797(4) 1.1151(10) 0.038(9) Uiso 1 1 d D . . H9 H 0.618(7) 1.053(3) 0.376(3) 0.051(12) Uiso 1 1 d D . . H10 H 0.298(9) 0.5517(18) 0.537(3) 0.072(15) Uiso 1 1 d D . . N1 N 0.1483(4) 0.8240(3) 0.39907(18) 0.0265(5) Uani 1 1 d . . . H1A H 0.0465 0.8257 0.3410 0.040 Uiso 1 1 calc R . . H1B H 0.2095 0.9145 0.4255 0.040 Uiso 1 1 calc R . . H1C H 0.0636 0.7771 0.4455 0.040 Uiso 1 1 calc R . . N2 N -0.2540(6) 0.9054(3) 0.9121(2) 0.0408(7) Uani 1 1 d D . . N3 N -0.3008(5) 0.9011(3) 1.0091(2) 0.0398(7) Uani 1 1 d . . . N4 N -0.1690(5) 0.8081(3) 1.0501(2) 0.0337(6) Uani 1 1 d D . . O1 O 0.6154(4) 0.8713(2) 0.55942(16) 0.0337(5) Uani 1 1 d . . . O2 O 0.3403(4) 0.6348(2) 0.55898(16) 0.0284(5) Uani 1 1 d D . . O3 O 0.7476(4) 0.6450(2) 0.47561(16) 0.0291(5) Uani 1 1 d . . . O4 O 0.7278(4) 0.7734(2) 0.24171(16) 0.0343(5) Uani 1 1 d . . . O5 O 0.3403(4) 0.8938(2) 0.20573(16) 0.0353(5) Uani 1 1 d . . . O6 O 0.6910(4) 0.9939(2) 0.35053(18) 0.0366(5) Uani 1 1 d D . . P1 P 0.54109(13) 0.72566(7) 0.49971(5) 0.0235(3) Uani 1 1 d . . . P2 P 0.53891(13) 0.85666(8) 0.28309(5) 0.0259(3) Uani 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 C1 0.0161(14) 0.0272(13) 0.0280(14) 0.0045(11) 0.0051(10) 0.0035(11) C2 0.0312(17) 0.0323(15) 0.0355(16) 0.0014(12) 0.0039(13) 0.0015(13) C3 0.0355(19) 0.0381(16) 0.0349(17) 0.0053(13) 0.0032(13) -0.0095(14) C4 0.0280(17) 0.0338(15) 0.0361(16) 0.0039(12) 0.0095(13) -0.0007(13) C5 0.038(2) 0.0378(17) 0.0470(19) 0.0061(14) 0.0077(15) 0.0018(15) C6 0.039(2) 0.047(2) 0.066(2) -0.0038(18) 0.0186(18) 0.0013(17) C7 0.054(3) 0.065(2) 0.050(2) -0.0114(19) 0.0251(18) -0.015(2) C8 0.052(2) 0.062(2) 0.0307(18) 0.0062(16) 0.0074(15) -0.018(2) N1 0.0164(12) 0.0311(12) 0.0337(13) 0.0071(10) 0.0069(9) 0.0045(10) N2 0.0391(17) 0.0394(15) 0.0429(16) 0.0153(13) -0.0011(13) 0.0017(13) N3 0.0335(16) 0.0417(15) 0.0441(16) 0.0101(12) 0.0027(12) 0.0047(12) N4 0.0335(15) 0.0396(14) 0.0304(14) 0.0104(11) 0.0070(11) 0.0078(12) O1 0.0316(13) 0.0319(11) 0.0365(12) 0.0040(9) 0.0022(9) 0.0025(9) O2 0.0235(11) 0.0303(11) 0.0342(11) 0.0091(9) 0.0136(8) 0.0033(9) O3 0.0165(10) 0.0302(10) 0.0438(12) 0.0108(9) 0.0095(8) 0.0068(8) O4 0.0258(12) 0.0492(13) 0.0339(11) 0.0109(10) 0.0124(9) 0.0162(10) O5 0.0222(11) 0.0492(13) 0.0379(12) 0.0189(10) 0.0063(9) 0.0084(10) O6 0.0270(13) 0.0365(12) 0.0454(13) 0.0071(10) 0.0107(10) -0.0029(10) P1 0.0174(4) 0.0257(4) 0.0286(4) 0.0069(3) 0.0054(3) 0.0038(3) P2 0.0171(4) 0.0340(5) 0.0291(5) 0.0098(3) 0.0076(3) 0.0052(3) _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 C1 N1 1.517(3) . ? C1 C2 1.542(4) . ? C1 P1 1.851(3) . ? C1 P2 1.856(3) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 N2 1.369(4) . ? C3 C4 1.396(4) . ? C3 C8 1.400(5) . ? C4 N4 1.366(4) . ? C4 C5 1.404(5) . ? C5 C6 1.372(5) . ? C5 H5 0.9300 . ? C6 C7 1.394(6) . ? C6 H6 0.9300 . ? C7 C8 1.377(6) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? N2 N3 1.306(4) . ? N2 H2 0.849(10) . ? N3 N4 1.322(4) . ? N4 H4 0.853(10) . ? O1 P1 1.493(2) . ? O2 P1 1.570(2) . ? O2 H10 0.798(10) . ? O3 P1 1.498(2) . ? O4 P2 1.504(2) . ? O5 P2 1.498(2) . ? O6 P2 1.566(2) . ? O6 H9 0.801(10) . ? 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 N1 C1 C2 107.6(2) . . ? N1 C1 P1 107.00(17) . . ? C2 C1 P1 111.02(19) . . ? N1 C1 P2 106.66(16) . . ? C2 C1 P2 108.77(19) . . ? P1 C1 P2 115.43(15) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N2 C3 C4 105.1(3) . . ? N2 C3 C8 132.9(3) . . ? C4 C3 C8 122.0(4) . . ? N4 C4 C3 104.8(3) . . ? N4 C4 C5 133.4(3) . . ? C3 C4 C5 121.7(3) . . ? C6 C5 C4 115.4(3) . . ? C6 C5 H5 122.3 . . ? C4 C5 H5 122.3 . . ? C5 C6 C7 123.0(4) . . ? C5 C6 H6 118.5 . . ? C7 C6 H6 118.5 . . ? C8 C7 C6 122.2(3) . . ? C8 C7 H7 118.9 . . ? C6 C7 H7 118.9 . . ? C7 C8 C3 115.6(4) . . ? C7 C8 H8 122.2 . . ? C3 C8 H8 122.2 . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? N3 N2 C3 111.9(3) . . ? N3 N2 H2 123(3) . . ? C3 N2 H2 125(3) . . ? N2 N3 N4 106.4(3) . . ? N3 N4 C4 111.7(3) . . ? N3 N4 H4 118(2) . . ? C4 N4 H4 130(2) . . ? P1 O2 H10 115(4) . . ? P2 O6 H9 119(3) . . ? O1 P1 O3 117.01(12) . . ? O1 P1 O2 107.14(12) . . ? O3 P1 O2 112.55(11) . . ? O1 P1 C1 108.87(12) . . ? O3 P1 C1 107.31(12) . . ? O2 P1 C1 103.00(13) . . ? O5 P2 O4 117.51(12) . . ? O5 P2 O6 112.49(13) . . ? O4 P2 O6 106.60(13) . . ? O5 P2 C1 104.23(13) . . ? O4 P2 C1 109.04(12) . . ? O6 P2 C1 106.43(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 N2 C3 C4 N4 1.4(3) . . . . ? C8 C3 C4 N4 -179.8(3) . . . . ? N2 C3 C4 C5 -176.3(3) . . . . ? C8 C3 C4 C5 2.4(5) . . . . ? N4 C4 C5 C6 -179.7(3) . . . . ? C3 C4 C5 C6 -2.7(5) . . . . ? C4 C5 C6 C7 1.4(5) . . . . ? C5 C6 C7 C8 0.3(6) . . . . ? C6 C7 C8 C3 -0.7(5) . . . . ? N2 C3 C8 C7 177.7(3) . . . . ? C4 C3 C8 C7 -0.7(5) . . . . ? C4 C3 N2 N3 -0.7(3) . . . . ? C8 C3 N2 N3 -179.2(4) . . . . ? C3 N2 N3 N4 -0.4(3) . . . . ? N2 N3 N4 C4 1.4(4) . . . . ? C3 C4 N4 N3 -1.8(4) . . . . ? C5 C4 N4 N3 175.6(3) . . . . ? N1 C1 P1 O1 -54.25(19) . . . . ? C2 C1 P1 O1 -171.37(19) . . . . ? P2 C1 P1 O1 64.26(17) . . . . ? N1 C1 P1 O3 178.21(15) . . . . ? C2 C1 P1 O3 61.1(2) . . . . ? P2 C1 P1 O3 -63.28(17) . . . . ? N1 C1 P1 O2 59.24(18) . . . . ? C2 C1 P1 O2 -57.9(2) . . . . ? P2 C1 P1 O2 177.75(13) . . . . ? N1 C1 P2 O5 -44.72(19) . . . . ? C2 C1 P2 O5 71.1(2) . . . . ? P1 C1 P2 O5 -163.42(14) . . . . ? N1 C1 P2 O4 -171.00(16) . . . . ? C2 C1 P2 O4 -55.2(2) . . . . ? P1 C1 P2 O4 70.30(18) . . . . ? N1 C1 P2 O6 74.37(19) . . . . ? C2 C1 P2 O6 -169.86(19) . . . . ? P1 C1 P2 O6 -44.33(18) . . . . ? 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 H1C O3 0.89 2.04 2.835(3) 148.1 1_455 N1 H1B O1 0.89 2.07 2.925(3) 162.1 2_676 N1 H1A O4 0.89 2.02 2.862(3) 156.6 1_455 O2 H10 O3 0.798(10) 1.812(17) 2.585(3) 163(5) 2_666 O6 H9 O1 0.801(10) 1.800(18) 2.567(3) 160(4) 2_676 N4 H4 O4 0.853(10) 1.796(15) 2.623(3) 163(4) 1_456 N2 H2 O5 0.849(10) 1.748(16) 2.574(3) 164(4) 2_576 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.871 _refine_diff_density_min -0.582 _refine_diff_density_rms 0.114 data_101123csp_0m _database_code_depnum_ccdc_archive 'CCDC 805173' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H7 N3 O' _chemical_formula_weight 149.16 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)/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 7.503(2) _cell_length_b 9.923(3) _cell_length_c 9.413(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.388(4) _cell_angle_gamma 90.00 _cell_volume 697.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1298 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 25.13 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9607 _exptl_absorpt_correction_T_max 0.9811 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 4402 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 28.00 _reflns_number_total 1676 _reflns_number_gt 1197 _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^)+(0.0683P)^2^+0.0451P] 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 SHELXL _refine_ls_extinction_coef 0.009(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1676 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1347 _refine_ls_wR_factor_gt 0.1252 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 0.71606(16) 0.47861(11) 0.09610(11) 0.0620(4) Uani 1 1 d . . . H1 H 0.7316 0.4033 0.0636 0.093 Uiso 1 1 calc R . . N1 N 0.64372(17) 0.43177(12) 0.32971(14) 0.0522(4) Uani 1 1 d . . . C5 C 0.7676(2) 0.41435(15) 0.54753(16) 0.0500(4) Uani 1 1 d . . . C6 C 0.71434(18) 0.50740(14) 0.44156(15) 0.0457(4) Uani 1 1 d . . . N3 N 0.72615(19) 0.28798(12) 0.49383(16) 0.0591(4) Uani 1 1 d . . . N2 N 0.65334(19) 0.30035(12) 0.36372(16) 0.0595(4) Uani 1 1 d . . . C1 C 0.7369(2) 0.64529(15) 0.46180(18) 0.0557(4) Uani 1 1 d . . . H1A H 0.6998 0.7071 0.3909 0.067 Uiso 1 1 calc R . . C7 C 0.5792(2) 0.47396(18) 0.18401(18) 0.0615(5) Uani 1 1 d . . . H7A H 0.4883 0.4113 0.1448 0.074 Uiso 1 1 calc R . . H7B H 0.5246 0.5624 0.1874 0.074 Uiso 1 1 calc R . . C4 C 0.8483(2) 0.45721(18) 0.67909(18) 0.0603(5) Uani 1 1 d . . . H4 H 0.8846 0.3959 0.7508 0.072 Uiso 1 1 calc R . . C3 C 0.8720(2) 0.59234(18) 0.6987(2) 0.0648(5) Uani 1 1 d . . . H3 H 0.9263 0.6237 0.7853 0.078 Uiso 1 1 calc R . . C2 C 0.8164(2) 0.68509(17) 0.5914(2) 0.0624(5) Uani 1 1 d . . . H2 H 0.8343 0.7766 0.6090 0.075 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 0.0833(9) 0.0500(6) 0.0533(7) -0.0006(5) 0.0100(6) -0.0039(5) N1 0.0572(8) 0.0435(7) 0.0568(8) 0.0004(5) 0.0101(6) -0.0011(5) C5 0.0484(8) 0.0454(8) 0.0584(9) 0.0017(6) 0.0156(7) 0.0058(6) C6 0.0432(8) 0.0430(8) 0.0522(8) -0.0004(6) 0.0124(6) 0.0030(5) N3 0.0699(9) 0.0423(8) 0.0668(9) 0.0051(6) 0.0153(7) 0.0028(6) N2 0.0706(9) 0.0435(7) 0.0659(9) 0.0003(6) 0.0143(7) -0.0040(6) C1 0.0561(9) 0.0435(8) 0.0693(11) 0.0016(7) 0.0161(8) 0.0047(6) C7 0.0631(10) 0.0603(10) 0.0599(10) 0.0027(7) -0.0016(8) 0.0030(8) C4 0.0556(9) 0.0692(11) 0.0566(10) 0.0048(8) 0.0083(7) 0.0146(7) C3 0.0569(10) 0.0710(11) 0.0664(11) -0.0153(9) 0.0053(8) 0.0066(8) C2 0.0607(10) 0.0488(9) 0.0792(12) -0.0137(8) 0.0139(8) 0.0005(7) _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 C7 1.379(2) . ? O1 H1 0.8200 . ? N1 N2 1.3431(17) . ? N1 C6 1.3593(19) . ? N1 C7 1.472(2) . ? C5 N3 1.377(2) . ? C5 C6 1.390(2) . ? C5 C4 1.393(2) . ? C6 C1 1.390(2) . ? N3 N2 1.299(2) . ? C1 C2 1.365(2) . ? C1 H1A 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C4 C3 1.363(2) . ? C4 H4 0.9300 . ? C3 C2 1.401(3) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? 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 C7 O1 H1 109.5 . . ? N2 N1 C6 110.07(13) . . ? N2 N1 C7 120.26(13) . . ? C6 N1 C7 129.42(13) . . ? N3 C5 C6 107.56(14) . . ? N3 C5 C4 131.98(15) . . ? C6 C5 C4 120.45(15) . . ? N1 C6 C1 133.11(14) . . ? N1 C6 C5 104.71(14) . . ? C1 C6 C5 122.17(14) . . ? N2 N3 C5 108.70(12) . . ? N3 N2 N1 108.96(12) . . ? C2 C1 C6 116.41(15) . . ? C2 C1 H1A 121.8 . . ? C6 C1 H1A 121.8 . . ? O1 C7 N1 111.75(13) . . ? O1 C7 H7A 109.3 . . ? N1 C7 H7A 109.3 . . ? O1 C7 H7B 109.3 . . ? N1 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C3 C4 C5 117.46(15) . . ? C3 C4 H4 121.3 . . ? C5 C4 H4 121.3 . . ? C4 C3 C2 121.50(17) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C1 C2 C3 121.99(16) . . ? C1 C2 H2 119.0 . . ? C3 C2 H2 119.0 . . ? 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 N2 N1 C6 C1 179.91(15) . . . . ? C7 N1 C6 C1 5.8(3) . . . . ? N2 N1 C6 C5 -0.30(15) . . . . ? C7 N1 C6 C5 -174.38(14) . . . . ? N3 C5 C6 N1 -0.03(15) . . . . ? C4 C5 C6 N1 179.52(13) . . . . ? N3 C5 C6 C1 179.80(13) . . . . ? C4 C5 C6 C1 -0.7(2) . . . . ? C6 C5 N3 N2 0.35(17) . . . . ? C4 C5 N3 N2 -179.13(15) . . . . ? C5 N3 N2 N1 -0.54(18) . . . . ? C6 N1 N2 N3 0.53(17) . . . . ? C7 N1 N2 N3 175.24(13) . . . . ? N1 C6 C1 C2 -179.51(14) . . . . ? C5 C6 C1 C2 0.7(2) . . . . ? N2 N1 C7 O1 -87.31(17) . . . . ? C6 N1 C7 O1 86.25(19) . . . . ? N3 C5 C4 C3 179.47(15) . . . . ? C6 C5 C4 C3 0.0(2) . . . . ? C5 C4 C3 C2 0.5(2) . . . . ? C6 C1 C2 C3 -0.2(2) . . . . ? C4 C3 C2 C1 -0.4(2) . . . . ? 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 O1 H1 N3 0.82 2.01 2.8184(18) 169.9 4_565 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.240 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.036