# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Alan Katritzky' _publ_contact_author_email katritzky@chem.ufl.edu loop_ _publ_author_name 'Khanh Ha' 'Jean-Christophe Monbaliu' 'Byron Williams' 'Girinath Pillai' 'Charles Ocampo' 'Matthias Zeller' 'Christian Stevens' 'Alan Katritzky' data_11mz400_0m _database_code_depnum_ccdc_archive 'CCDC 881662' #TrackingRef '- 6a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H8 N2 O2' _chemical_formula_weight 128.13 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 9.243(3) _cell_length_b 7.153(2) _cell_length_c 8.902(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.489(4) _cell_angle_gamma 90.00 _cell_volume 588.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2725 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 31.42 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.41 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6701 _exptl_absorpt_correction_T_max 0.7462 _exptl_absorpt_process_details 'Apex2 v2011.2-0 (Bruker, 2011)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 6608 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.58 _diffrn_reflns_theta_max 31.57 _reflns_number_total 1871 _reflns_number_gt 1728 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2011.2-0 (Bruker, 2011)' _computing_cell_refinement 'Apex2 v2011.2-0' _computing_data_reduction 'Apex2 v2011.2-0' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2003; Sheldrick, 2008)' _computing_structure_refinement ; SHELXTL 6.14, Shelxle (H\"ubschle et al., 2011) ; _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0551P)^2^+0.1376P] 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 1871 _refine_ls_number_parameters 106 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0965 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.052 _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 0.07488(8) 0.59207(10) 0.64259(8) 0.01246(15) Uani 1 1 d . . . C2 C 0.13001(8) 0.75826(10) 0.55510(8) 0.01373(16) Uani 1 1 d D . . H2A H 0.1313(13) 0.8620(16) 0.6278(12) 0.016 Uiso 1 1 d D . . H2B H 0.0552(12) 0.7878(16) 0.4815(12) 0.016 Uiso 1 1 d D . . C3 C 0.27495(8) 0.74406(11) 0.47806(8) 0.01480(16) Uani 1 1 d D . . H3A H 0.2696(12) 0.6497(17) 0.3960(12) 0.018 Uiso 1 1 d D . . H3B H 0.2962(13) 0.8657(16) 0.4312(13) 0.018 Uiso 1 1 d D . . C4 C 0.40859(8) 0.53868(10) 0.65324(8) 0.01293(16) Uani 1 1 d . . . C5 C 0.29750(8) 0.39067(11) 0.60837(9) 0.01429(16) Uani 1 1 d D . . H5A H 0.2936(12) 0.3756(17) 0.4994(11) 0.017 Uiso 1 1 d D . . H5B H 0.3276(13) 0.2753(15) 0.6563(13) 0.017 Uiso 1 1 d D . . N1 N 0.15559(7) 0.43823(9) 0.66784(7) 0.01375(15) Uani 1 1 d D . . H1 H 0.1142(12) 0.3510(16) 0.7213(12) 0.016 Uiso 1 1 d D . . N2 N 0.39474(7) 0.70300(9) 0.58270(7) 0.01420(15) Uani 1 1 d D . . H2 H 0.4430(13) 0.7963(15) 0.6249(13) 0.017 Uiso 1 1 d D . . O1 O -0.04836(6) 0.60298(8) 0.69575(7) 0.01622(15) Uani 1 1 d . . . O2 O 0.50337(6) 0.51117(8) 0.75193(7) 0.01737(15) 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 0.0124(3) 0.0128(3) 0.0121(3) -0.0019(2) -0.0004(2) -0.0010(2) C2 0.0130(3) 0.0132(3) 0.0150(3) 0.0015(2) 0.0007(2) 0.0002(2) C3 0.0136(3) 0.0180(3) 0.0128(3) 0.0024(2) 0.0003(2) -0.0005(2) C4 0.0112(3) 0.0133(3) 0.0144(3) -0.0021(2) 0.0020(2) 0.0009(2) C5 0.0117(3) 0.0127(3) 0.0185(3) -0.0026(2) 0.0010(2) 0.0003(2) N1 0.0122(3) 0.0123(3) 0.0169(3) 0.0007(2) 0.0019(2) -0.0006(2) N2 0.0122(3) 0.0144(3) 0.0160(3) 0.0007(2) -0.0007(2) -0.0019(2) O1 0.0128(3) 0.0164(3) 0.0196(3) -0.0007(2) 0.0033(2) 0.00015(19) O2 0.0151(3) 0.0160(3) 0.0208(3) -0.0002(2) -0.0040(2) 0.0017(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 O1 1.2472(9) . ? C1 N1 1.3451(10) . ? C1 C2 1.5165(11) . ? C2 C3 1.5242(11) . ? C2 H2A 0.984(10) . ? C2 H2B 0.963(10) . ? C3 N2 1.4581(10) . ? C3 H3A 0.995(10) . ? C3 H3B 0.987(11) . ? C4 O2 1.2401(9) . ? C4 N2 1.3371(10) . ? C4 C5 1.5210(11) . ? C5 N1 1.4671(10) . ? C5 H5A 0.976(10) . ? C5 H5B 0.967(10) . ? N1 H1 0.878(11) . ? N2 H2 0.882(11) . ? 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 O1 C1 N1 119.72(7) . . ? O1 C1 C2 117.92(7) . . ? N1 C1 C2 122.33(7) . . ? C1 C2 C3 119.33(6) . . ? C1 C2 H2A 104.6(7) . . ? C3 C2 H2A 110.5(7) . . ? C1 C2 H2B 106.0(7) . . ? C3 C2 H2B 109.4(7) . . ? H2A C2 H2B 106.1(10) . . ? N2 C3 C2 112.81(6) . . ? N2 C3 H3A 110.8(7) . . ? C2 C3 H3A 110.4(7) . . ? N2 C3 H3B 107.0(7) . . ? C2 C3 H3B 108.6(7) . . ? H3A C3 H3B 107.1(10) . . ? O2 C4 N2 121.97(7) . . ? O2 C4 C5 122.36(7) . . ? N2 C4 C5 115.64(7) . . ? N1 C5 C4 110.34(6) . . ? N1 C5 H5A 112.0(7) . . ? C4 C5 H5A 110.2(7) . . ? N1 C5 H5B 106.8(7) . . ? C4 C5 H5B 107.1(7) . . ? H5A C5 H5B 110.3(10) . . ? C1 N1 C5 128.80(7) . . ? C1 N1 H1 115.1(8) . . ? C5 N1 H1 115.9(8) . . ? C4 N2 C3 122.61(6) . . ? C4 N2 H2 115.1(8) . . ? C3 N2 H2 119.2(8) . . ? 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 C1 C2 C3 -175.19(7) . . . . ? N1 C1 C2 C3 6.85(11) . . . . ? C1 C2 C3 N2 -58.81(9) . . . . ? O2 C4 C5 N1 105.89(8) . . . . ? N2 C4 C5 N1 -72.06(9) . . . . ? O1 C1 N1 C5 175.39(7) . . . . ? C2 C1 N1 C5 -6.68(12) . . . . ? C4 C5 N1 C1 59.07(10) . . . . ? O2 C4 N2 C3 -173.37(7) . . . . ? C5 C4 N2 C3 4.58(10) . . . . ? C2 C3 N2 C4 68.30(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.878(11) 2.021(11) 2.8757(11) 163.9(11) 2_546 N2 H2 O2 0.882(11) 1.944(11) 2.8002(10) 163.2(11) 2_656 _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.473 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.046 # Attachment '- 6c.cif' data_11mz399_0m _database_code_depnum_ccdc_archive 'CCDC 881663' #TrackingRef '- 6c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H12 N2 O2' _chemical_formula_weight 156.19 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 5.6500(16) _cell_length_b 7.884(2) _cell_length_c 9.777(3) _cell_angle_alpha 110.051(3) _cell_angle_beta 90.330(4) _cell_angle_gamma 109.728(3) _cell_volume 381.49(19) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2092 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 30.80 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 168 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6852 _exptl_absorpt_correction_T_max 0.7462 _exptl_absorpt_process_details 'Apex2 v2011.2-0 (Bruker, 2011)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 7466 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0160 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 31.47 _reflns_number_total 2304 _reflns_number_gt 2184 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2011.2-0 (Bruker, 2011)' _computing_cell_refinement 'Apex2 v2011.2-0' _computing_data_reduction 'Apex2 v2011.2-0' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2003; Sheldrick, 2008)' _computing_structure_refinement ; SHELXTL 6.14, Shelxle (H\"ubschle et al., 2011) ; _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0545P)^2^+0.1036P] 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 2304 _refine_ls_number_parameters 108 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0965 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.00741(14) 0.72290(11) 0.89308(8) 0.01316(15) Uani 1 1 d . . . C2 C -0.00396(15) 0.51971(11) 0.80982(8) 0.01500(16) Uani 1 1 d . . . H2A H -0.0957 0.4725 0.7097 0.018 Uiso 1 1 calc R . . H2B H -0.0995 0.4335 0.8602 0.018 Uiso 1 1 calc R . . C3 C 0.26142(16) 0.51107(11) 0.79911(9) 0.01600(16) Uani 1 1 d . . . H3A H 0.3709 0.5975 0.8938 0.019 Uiso 1 1 calc R . . H3B H 0.2510 0.3774 0.7822 0.019 Uiso 1 1 calc R . . C4 C 0.35796(13) 0.70209(10) 0.63192(8) 0.01205(15) Uani 1 1 d . . . C5 C 0.26631(14) 0.86643(10) 0.71897(8) 0.01155(14) Uani 1 1 d . . . C6 C 0.50031(15) 1.05406(11) 0.75810(9) 0.01742(16) Uani 1 1 d . . . H6A H 0.5595 1.0697 0.6676 0.026 Uiso 1 1 calc R . . H6B H 0.6358 1.0471 0.8166 0.026 Uiso 1 1 calc R . . H6C H 0.4547 1.1649 0.8151 0.026 Uiso 1 1 calc R . . C7 C 0.05919(16) 0.86890(13) 0.61810(9) 0.01979(17) Uani 1 1 d . . . H7A H 0.1246 0.8793 0.5275 0.030 Uiso 1 1 calc R . . H7B H 0.0096 0.9801 0.6685 0.030 Uiso 1 1 calc R . . H7C H -0.0889 0.7490 0.5939 0.030 Uiso 1 1 calc R . . N1 N 0.37813(13) 0.56825(10) 0.68126(7) 0.01449(15) Uani 1 1 d D . . H1 H 0.445(2) 0.4926(17) 0.6213(13) 0.017 Uiso 1 1 d D . . N2 N 0.17224(13) 0.86774(9) 0.85955(7) 0.01401(14) Uani 1 1 d D . . H2 H 0.164(2) 0.9803(16) 0.9110(13) 0.017 Uiso 1 1 d D . . O1 O -0.11514(12) 0.75749(9) 0.99748(7) 0.01862(15) Uani 1 1 d . . . O2 O 0.42723(11) 0.70533(8) 0.51167(6) 0.01608(14) 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 0.0144(3) 0.0131(3) 0.0123(3) 0.0042(2) 0.0032(2) 0.0058(3) C2 0.0169(3) 0.0116(3) 0.0148(3) 0.0035(3) 0.0044(3) 0.0047(3) C3 0.0211(4) 0.0172(3) 0.0151(3) 0.0083(3) 0.0066(3) 0.0109(3) C4 0.0117(3) 0.0127(3) 0.0109(3) 0.0026(2) 0.0019(2) 0.0051(2) C5 0.0131(3) 0.0120(3) 0.0104(3) 0.0037(2) 0.0039(2) 0.0061(2) C6 0.0172(3) 0.0130(3) 0.0186(4) 0.0039(3) 0.0068(3) 0.0031(3) C7 0.0203(4) 0.0276(4) 0.0164(3) 0.0072(3) 0.0026(3) 0.0155(3) N1 0.0185(3) 0.0152(3) 0.0132(3) 0.0052(2) 0.0062(2) 0.0102(2) N2 0.0188(3) 0.0111(3) 0.0117(3) 0.0028(2) 0.0069(2) 0.0062(2) O1 0.0234(3) 0.0172(3) 0.0180(3) 0.0073(2) 0.0117(2) 0.0097(2) O2 0.0210(3) 0.0187(3) 0.0119(3) 0.0057(2) 0.0066(2) 0.0112(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 O1 1.2412(10) . ? C1 N2 1.3494(10) . ? C1 C2 1.5063(11) . ? C2 C3 1.5263(12) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N1 1.4595(10) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O2 1.2471(9) . ? C4 N1 1.3375(10) . ? C4 C5 1.5405(11) . ? C5 N2 1.4746(10) . ? C5 C7 1.5355(11) . ? C5 C6 1.5390(11) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? N1 H1 0.871(11) . ? N2 H2 0.874(11) . ? 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 O1 C1 N2 121.00(7) . . ? O1 C1 C2 120.82(7) . . ? N2 C1 C2 117.90(7) . . ? C1 C2 C3 111.37(6) . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? N1 C3 C2 112.86(6) . . ? N1 C3 H3A 109.0 . . ? C2 C3 H3A 109.0 . . ? N1 C3 H3B 109.0 . . ? C2 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? O2 C4 N1 120.28(7) . . ? O2 C4 C5 115.51(6) . . ? N1 C4 C5 124.11(7) . . ? N2 C5 C7 108.68(6) . . ? N2 C5 C6 105.55(6) . . ? C7 C5 C6 110.10(7) . . ? N2 C5 C4 118.55(6) . . ? C7 C5 C4 108.29(6) . . ? C6 C5 C4 105.44(6) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 N1 C3 129.11(7) . . ? C4 N1 H1 111.8(8) . . ? C3 N1 H1 117.7(8) . . ? C1 N2 C5 129.94(6) . . ? C1 N2 H2 112.1(8) . . ? C5 N2 H2 111.2(8) . . ? 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 C1 C2 C3 -128.32(8) . . . . ? N2 C1 C2 C3 45.68(9) . . . . ? C1 C2 C3 N1 -81.59(8) . . . . ? O2 C4 C5 N2 177.69(6) . . . . ? N1 C4 C5 N2 -5.87(11) . . . . ? O2 C4 C5 C7 53.36(9) . . . . ? N1 C4 C5 C7 -130.20(8) . . . . ? O2 C4 C5 C6 -64.47(8) . . . . ? N1 C4 C5 C6 111.97(8) . . . . ? O2 C4 N1 C3 -165.18(8) . . . . ? C5 C4 N1 C3 18.54(12) . . . . ? C2 C3 N1 C4 34.81(11) . . . . ? O1 C1 N2 C5 -155.74(8) . . . . ? C2 C1 N2 C5 30.26(12) . . . . ? C7 C5 N2 C1 77.18(10) . . . . ? C6 C5 N2 C1 -164.74(8) . . . . ? C4 C5 N2 C1 -46.96(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 N1 H1 O2 0.871(11) 2.006(11) 2.8733(10) 173.7(11) 2_666 N2 H2 O1 0.874(11) 2.067(11) 2.9335(12) 171.0(11) 2_577 _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.440 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.044