# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_ak79m _database_code_depnum_ccdc_archive 'CCDC 857953' #TrackingRef 'web_deposit_cif_file_0_B.Sridhar_1323691733.ak79mf.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H7 N5 O2' _chemical_formula_sum 'C9 H7 N5 O2' _chemical_formula_weight 217.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 9.8335(7) _cell_length_b 8.2851(6) _cell_length_c 12.1849(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.006(0) _cell_angle_gamma 90.00 _cell_volume 971.01(12) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 7652 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 27.99 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.112 _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 294(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_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8941 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0139 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1715 _reflns_number_gt 1647 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material SHELXL97 _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^)+(0.0513P)^2^+0.2293P] 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 0.077(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1715 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0898 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 0.61478(12) 0.20906(16) 0.62317(10) 0.0382(3) Uani 1 1 d . . . C2 C 0.72478(14) 0.28637(19) 0.59191(13) 0.0520(4) Uani 1 1 d . . . H2 H 0.7930 0.2292 0.5658 0.062 Uiso 1 1 calc R . . C3 C 0.72940(16) 0.4524(2) 0.60101(14) 0.0605(4) Uani 1 1 d . . . H3 H 0.8028 0.5082 0.5812 0.073 Uiso 1 1 calc R . . C4 C 0.62751(17) 0.53768(19) 0.63890(14) 0.0610(4) Uani 1 1 d . . . H4 H 0.6336 0.6495 0.6444 0.073 Uiso 1 1 calc R . . C5 C 0.51638(15) 0.45863(17) 0.66878(12) 0.0513(4) Uani 1 1 d . . . H5 H 0.4469 0.5159 0.6931 0.062 Uiso 1 1 calc R . . C6 C 0.51185(12) 0.29279(15) 0.66141(10) 0.0377(3) Uani 1 1 d . . . C7 C 0.40777(11) 0.17200(15) 0.68746(9) 0.0358(3) Uani 1 1 d . . . C8 C 0.47354(12) 0.00845(15) 0.66217(9) 0.0350(3) Uani 1 1 d . . . C9 C 0.26799(11) 0.19102(15) 0.61030(9) 0.0346(3) Uani 1 1 d . . . N1 N 0.58851(10) 0.04200(13) 0.62378(9) 0.0393(3) Uani 1 1 d . . . N2 N 0.23300(10) 0.15119(13) 0.50372(8) 0.0401(3) Uani 1 1 d . . . N3 N 0.09853(11) 0.19865(15) 0.47033(9) 0.0464(3) Uani 1 1 d . . . N4 N 0.05373(11) 0.26389(16) 0.55223(9) 0.0505(3) Uani 1 1 d . . . N5 N 0.15960(10) 0.25918(15) 0.64081(9) 0.0432(3) Uani 1 1 d . . . O1 O 0.42744(10) -0.12498(11) 0.67601(8) 0.0474(3) Uani 1 1 d . . . O2 O 0.38329(9) 0.17528(13) 0.79730(7) 0.0483(3) Uani 1 1 d . . . H2O H 0.4558(19) 0.222(2) 0.8434(15) 0.067(5) Uiso 1 1 d . . . H5N H 0.1503(17) 0.299(2) 0.7068(15) 0.058(4) Uiso 1 1 d . . . H1N H 0.6432(17) -0.033(2) 0.6021(12) 0.055(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 C1 0.0291(6) 0.0472(7) 0.0374(6) 0.0024(5) 0.0049(5) -0.0008(5) C2 0.0347(7) 0.0641(9) 0.0594(8) 0.0064(7) 0.0146(6) -0.0046(6) C3 0.0477(8) 0.0645(10) 0.0677(9) 0.0114(8) 0.0087(7) -0.0172(7) C4 0.0635(10) 0.0462(8) 0.0687(10) 0.0023(7) 0.0032(8) -0.0117(7) C5 0.0485(8) 0.0476(8) 0.0561(8) -0.0050(6) 0.0070(6) 0.0026(6) C6 0.0307(6) 0.0462(7) 0.0346(6) -0.0010(5) 0.0031(5) -0.0002(5) C7 0.0286(6) 0.0491(7) 0.0301(6) -0.0015(5) 0.0068(4) 0.0009(5) C8 0.0295(6) 0.0459(7) 0.0287(5) 0.0033(5) 0.0042(4) 0.0002(5) C9 0.0284(6) 0.0435(6) 0.0332(6) -0.0007(5) 0.0096(5) 0.0011(5) N1 0.0313(5) 0.0446(6) 0.0441(6) 0.0011(4) 0.0128(4) 0.0039(4) N2 0.0310(5) 0.0550(7) 0.0339(5) -0.0014(4) 0.0059(4) 0.0030(4) N3 0.0320(5) 0.0675(7) 0.0379(6) 0.0016(5) 0.0031(4) 0.0029(5) N4 0.0300(5) 0.0776(8) 0.0431(6) 0.0010(5) 0.0054(5) 0.0087(5) N5 0.0301(5) 0.0640(7) 0.0359(6) -0.0050(5) 0.0079(4) 0.0067(5) O1 0.0480(5) 0.0465(6) 0.0506(6) 0.0052(4) 0.0174(4) -0.0041(4) O2 0.0370(5) 0.0785(7) 0.0301(5) -0.0070(4) 0.0085(4) -0.0028(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 C1 C2 1.3772(18) . ? C1 C6 1.3853(17) . ? C1 N1 1.4083(17) . ? C2 C3 1.380(2) . ? C2 H2 0.9300 . ? C3 C4 1.381(2) . ? C3 H3 0.9300 . ? C4 C5 1.386(2) . ? C4 H4 0.9300 . ? C5 C6 1.3770(19) . ? C5 H5 0.9300 . ? C6 C7 1.5116(17) . ? C7 O2 1.4085(14) . ? C7 C9 1.5035(16) . ? C7 C8 1.5595(17) . ? C8 O1 1.2198(15) . ? C8 N1 1.3395(15) . ? C9 N2 1.3144(15) . ? C9 N5 1.3260(15) . ? N1 H1N 0.897(17) . ? N2 N3 1.3582(15) . ? N3 N4 1.2903(16) . ? N4 N5 1.3352(15) . ? N5 H5N 0.891(17) . ? O2 H2O 0.90(2) . ? 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 C1 C6 122.07(13) . . ? C2 C1 N1 127.88(12) . . ? C6 C1 N1 110.05(10) . . ? C1 C2 C3 117.13(14) . . ? C1 C2 H2 121.4 . . ? C3 C2 H2 121.4 . . ? C2 C3 C4 121.50(14) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C3 C4 C5 120.83(14) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 118.09(14) . . ? C6 C5 H5 121.0 . . ? C4 C5 H5 121.0 . . ? C5 C6 C1 120.38(12) . . ? C5 C6 C7 131.37(12) . . ? C1 C6 C7 108.25(11) . . ? O2 C7 C9 106.11(9) . . ? O2 C7 C6 116.34(10) . . ? C9 C7 C6 111.73(10) . . ? O2 C7 C8 111.37(10) . . ? C9 C7 C8 109.28(9) . . ? C6 C7 C8 101.95(9) . . ? O1 C8 N1 126.96(12) . . ? O1 C8 C7 125.37(10) . . ? N1 C8 C7 107.67(10) . . ? N2 C9 N5 108.87(10) . . ? N2 C9 C7 127.51(10) . . ? N5 C9 C7 123.57(10) . . ? C8 N1 C1 112.01(10) . . ? C8 N1 H1N 124.0(10) . . ? C1 N1 H1N 124.0(10) . . ? C9 N2 N3 105.17(10) . . ? N4 N3 N2 110.93(10) . . ? N3 N4 N5 106.19(10) . . ? C9 N5 N4 108.83(10) . . ? C9 N5 H5N 130.5(11) . . ? N4 N5 H5N 120.7(11) . . ? C7 O2 H2O 109.4(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.5(2) . . . . ? N1 C1 C2 C3 -178.60(13) . . . . ? C1 C2 C3 C4 -0.6(2) . . . . ? C2 C3 C4 C5 -0.2(2) . . . . ? C3 C4 C5 C6 1.1(2) . . . . ? C4 C5 C6 C1 -1.14(19) . . . . ? C4 C5 C6 C7 179.72(13) . . . . ? C2 C1 C6 C5 0.35(19) . . . . ? N1 C1 C6 C5 179.60(12) . . . . ? C2 C1 C6 C7 179.68(11) . . . . ? N1 C1 C6 C7 -1.08(13) . . . . ? C5 C6 C7 O2 -57.13(18) . . . . ? C1 C6 C7 O2 123.65(11) . . . . ? C5 C6 C7 C9 64.92(17) . . . . ? C1 C6 C7 C9 -114.30(11) . . . . ? C5 C6 C7 C8 -178.49(13) . . . . ? C1 C6 C7 C8 2.29(11) . . . . ? O2 C7 C8 O1 52.08(15) . . . . ? C9 C7 C8 O1 -64.83(14) . . . . ? C6 C7 C8 O1 176.82(11) . . . . ? O2 C7 C8 N1 -127.54(10) . . . . ? C9 C7 C8 N1 115.55(10) . . . . ? C6 C7 C8 N1 -2.80(11) . . . . ? O2 C7 C9 N2 -159.38(12) . . . . ? C6 C7 C9 N2 72.86(16) . . . . ? C8 C7 C9 N2 -39.19(16) . . . . ? O2 C7 C9 N5 23.46(16) . . . . ? C6 C7 C9 N5 -104.30(13) . . . . ? C8 C7 C9 N5 143.65(12) . . . . ? O1 C8 N1 C1 -177.25(11) . . . . ? C7 C8 N1 C1 2.36(13) . . . . ? C2 C1 N1 C8 178.31(12) . . . . ? C6 C1 N1 C8 -0.88(14) . . . . ? N5 C9 N2 N3 0.24(14) . . . . ? C7 C9 N2 N3 -177.26(12) . . . . ? C9 N2 N3 N4 -0.05(15) . . . . ? N2 N3 N4 N5 -0.15(15) . . . . ? N2 C9 N5 N4 -0.34(15) . . . . ? C7 C9 N5 N4 177.28(11) . . . . ? N3 N4 N5 C9 0.30(15) . . . . ? 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 O2 H2O N3 0.90(2) 1.97(2) 2.8565(14) 167.7(16) 4_666 O2 H2O N4 0.90(2) 2.530(19) 3.2475(14) 137.5(14) 4_666 N5 H5N O1 0.891(17) 1.864(17) 2.7259(14) 162.1(16) 2_556 N1 H1N N2 0.897(17) 2.181(17) 3.0316(15) 158.0(13) 3_656 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.202 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.040 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_ak94m _database_code_depnum_ccdc_archive 'CCDC 857954' #TrackingRef 'web_deposit_cif_file_2_B.Sridhar_1323691733.ak94mf.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 N6 O' _chemical_formula_sum 'C15 H12 N6 O' _chemical_formula_weight 292.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 12.6583(8) _cell_length_b 7.1048(4) _cell_length_c 15.7542(10) _cell_angle_alpha 90.00 _cell_angle_beta 104.404(1) _cell_angle_gamma 90.00 _cell_volume 1372.31(15) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 9213 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 28.97 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.096 _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 294(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_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12706 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0129 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2426 _reflns_number_gt 2261 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material SHELXL97 _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^)+(0.0542P)^2^+0.3038P] 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 2426 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0976 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 0.28007(10) 0.16982(18) 0.09672(8) 0.0342(3) Uani 1 1 d . . . C2 C 0.31620(11) 0.0058(2) 0.06846(10) 0.0494(4) Uani 1 1 d . . . H2 H 0.2783 -0.0507 0.0166 0.059 Uiso 1 1 calc R . . C3 C 0.41048(13) -0.0737(2) 0.11902(13) 0.0611(5) Uani 1 1 d . . . H3 H 0.4369 -0.1846 0.1007 0.073 Uiso 1 1 calc R . . C4 C 0.46574(12) 0.0091(2) 0.19618(11) 0.0547(4) Uani 1 1 d . . . H4 H 0.5283 -0.0482 0.2298 0.066 Uiso 1 1 calc R . . C5 C 0.43032(10) 0.1750(2) 0.22462(9) 0.0418(3) Uani 1 1 d . . . H5 H 0.4677 0.2313 0.2767 0.050 Uiso 1 1 calc R . . C6 C 0.33765(10) 0.25389(18) 0.17300(8) 0.0334(3) Uani 1 1 d . . . C7 C 0.20267(9) 0.46504(17) 0.11898(7) 0.0312(3) Uani 1 1 d . . . C8 C 0.18012(9) 0.28736(17) 0.05923(7) 0.0311(3) Uani 1 1 d . . . C9 C 0.08173(9) 0.20240(17) 0.08110(7) 0.0305(3) Uani 1 1 d . . . C13 C 0.23416(10) 0.38619(18) -0.07409(8) 0.0348(3) Uani 1 1 d . . . C14 C 0.23408(12) 0.3084(2) -0.15419(9) 0.0476(4) Uani 1 1 d . . . H14 H 0.1821 0.2183 -0.1787 0.057 Uiso 1 1 calc R . . C15 C 0.30985(13) 0.3626(3) -0.19800(10) 0.0565(4) Uani 1 1 d . . . H15 H 0.3086 0.3101 -0.2523 0.068 Uiso 1 1 calc R . . C16 C 0.38727(12) 0.4933(2) -0.16233(10) 0.0544(4) Uani 1 1 d . . . H16 H 0.4393 0.5288 -0.1917 0.065 Uiso 1 1 calc R . . C17 C 0.38754(14) 0.5710(3) -0.08341(11) 0.0599(4) Uani 1 1 d . . . H17 H 0.4400 0.6605 -0.0591 0.072 Uiso 1 1 calc R . . C18 C 0.31110(13) 0.5189(2) -0.03896(10) 0.0513(4) Uani 1 1 d . . . H18 H 0.3118 0.5738 0.0148 0.062 Uiso 1 1 calc R . . N1 N 0.28819(8) 0.42522(16) 0.18529(7) 0.0362(3) Uani 1 1 d . . . N2 N 0.15082(8) 0.33195(16) -0.03338(7) 0.0354(3) Uani 1 1 d . . . N3 N 0.08285(9) 0.09172(16) 0.14752(7) 0.0411(3) Uani 1 1 d . . . N4 N -0.02257(9) 0.05502(18) 0.14430(8) 0.0457(3) Uani 1 1 d . . . N5 N -0.08569(9) 0.13945(17) 0.07926(8) 0.0436(3) Uani 1 1 d . . . N6 N -0.02091(8) 0.23320(16) 0.03882(7) 0.0364(3) Uani 1 1 d . . . O1 O 0.14804(7) 0.60739(13) 0.10750(6) 0.0396(2) Uani 1 1 d . . . H2N H 0.1144(12) 0.235(2) -0.0626(10) 0.046(4) Uiso 1 1 d . . . H3N H -0.0528(13) 0.306(2) -0.0078(12) 0.053(4) Uiso 1 1 d . . . H1N H 0.3121(12) 0.496(2) 0.2304(11) 0.049(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 C1 0.0295(6) 0.0362(7) 0.0352(6) -0.0010(5) 0.0045(5) -0.0033(5) C2 0.0406(7) 0.0443(8) 0.0567(9) -0.0149(7) -0.0006(6) 0.0018(6) C3 0.0472(8) 0.0469(9) 0.0795(11) -0.0169(8) -0.0025(8) 0.0109(7) C4 0.0375(7) 0.0487(8) 0.0684(10) 0.0002(7) -0.0047(7) 0.0082(6) C5 0.0338(7) 0.0464(8) 0.0398(7) 0.0004(6) -0.0009(5) -0.0015(6) C6 0.0297(6) 0.0368(7) 0.0326(6) 0.0007(5) 0.0054(5) -0.0020(5) C7 0.0312(6) 0.0346(6) 0.0274(6) 0.0014(5) 0.0066(5) -0.0023(5) C8 0.0294(6) 0.0342(6) 0.0277(6) -0.0001(5) 0.0034(5) -0.0032(5) C9 0.0306(6) 0.0320(6) 0.0265(6) 0.0008(5) 0.0024(4) -0.0018(5) C13 0.0333(6) 0.0390(7) 0.0314(6) 0.0035(5) 0.0070(5) 0.0001(5) C14 0.0479(8) 0.0568(9) 0.0390(7) -0.0073(6) 0.0125(6) -0.0087(7) C15 0.0588(9) 0.0731(11) 0.0431(8) -0.0027(7) 0.0229(7) 0.0012(8) C16 0.0469(8) 0.0694(10) 0.0522(9) 0.0145(8) 0.0225(7) -0.0008(7) C17 0.0554(9) 0.0676(11) 0.0593(10) -0.0001(8) 0.0189(8) -0.0243(8) C18 0.0555(9) 0.0585(9) 0.0428(8) -0.0087(7) 0.0178(7) -0.0216(7) N1 0.0355(6) 0.0399(6) 0.0292(5) -0.0059(5) 0.0001(4) 0.0010(5) N2 0.0336(5) 0.0443(6) 0.0261(5) -0.0008(5) 0.0036(4) -0.0093(5) N3 0.0366(6) 0.0485(7) 0.0358(6) 0.0120(5) 0.0047(5) -0.0030(5) N4 0.0402(6) 0.0531(7) 0.0432(6) 0.0133(5) 0.0092(5) -0.0062(5) N5 0.0340(6) 0.0507(7) 0.0456(7) 0.0087(5) 0.0086(5) -0.0065(5) N6 0.0303(5) 0.0412(6) 0.0349(6) 0.0088(5) 0.0029(4) -0.0025(4) O1 0.0421(5) 0.0381(5) 0.0353(5) -0.0001(4) 0.0038(4) 0.0052(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 C1 C2 1.3661(19) . ? C1 C6 1.3772(17) . ? C1 C8 1.5083(17) . ? C2 C3 1.380(2) . ? C2 H2 0.9300 . ? C3 C4 1.375(2) . ? C3 H3 0.9300 . ? C4 C5 1.375(2) . ? C4 H4 0.9300 . ? C5 C6 1.3701(18) . ? C5 H5 0.9300 . ? C6 N1 1.4041(17) . ? C7 O1 1.2131(15) . ? C7 N1 1.3344(15) . ? C7 C8 1.5580(17) . ? C8 N2 1.4483(15) . ? C8 C9 1.4992(16) . ? C9 N3 1.3062(16) . ? C9 N6 1.3225(16) . ? C13 C18 1.3696(19) . ? C13 C14 1.3775(19) . ? C13 N2 1.4174(16) . ? C14 C15 1.369(2) . ? C14 H14 0.9300 . ? C15 C16 1.366(2) . ? C15 H15 0.9300 . ? C16 C17 1.360(2) . ? C16 H16 0.9300 . ? C17 C18 1.379(2) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? N1 H1N 0.860(17) . ? N2 H2N 0.889(16) . ? N3 N4 1.3481(15) . ? N4 N5 1.2810(16) . ? N5 N6 1.3349(15) . ? N6 H3N 0.907(18) . ? 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 C1 C6 120.46(12) . . ? C2 C1 C8 131.36(11) . . ? C6 C1 C8 108.17(11) . . ? C1 C2 C3 118.20(13) . . ? C1 C2 H2 120.9 . . ? C3 C2 H2 120.9 . . ? C4 C3 C2 120.79(14) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C4 C3 121.30(13) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C6 C5 C4 117.25(13) . . ? C6 C5 H5 121.4 . . ? C4 C5 H5 121.4 . . ? C5 C6 C1 121.98(12) . . ? C5 C6 N1 128.19(12) . . ? C1 C6 N1 109.81(11) . . ? O1 C7 N1 127.94(11) . . ? O1 C7 C8 124.99(10) . . ? N1 C7 C8 106.99(10) . . ? N2 C8 C9 107.48(9) . . ? N2 C8 C1 119.68(10) . . ? C9 C8 C1 110.55(10) . . ? N2 C8 C7 113.20(10) . . ? C9 C8 C7 103.01(9) . . ? C1 C8 C7 101.67(9) . . ? N3 C9 N6 108.46(11) . . ? N3 C9 C8 125.62(10) . . ? N6 C9 C8 125.86(10) . . ? C18 C13 C14 119.00(12) . . ? C18 C13 N2 122.60(12) . . ? C14 C13 N2 118.32(12) . . ? C15 C14 C13 120.54(14) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C16 C15 C14 120.33(15) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 119.39(13) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 120.87(15) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C13 C18 C17 119.86(14) . . ? C13 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C7 N1 C6 112.25(10) . . ? C7 N1 H1N 125.0(11) . . ? C6 N1 H1N 122.7(11) . . ? C13 N2 C8 118.84(10) . . ? C13 N2 H2N 108.9(10) . . ? C8 N2 H2N 108.9(10) . . ? C9 N3 N4 105.84(10) . . ? N5 N4 N3 110.74(10) . . ? N4 N5 N6 106.29(10) . . ? C9 N6 N5 108.68(10) . . ? C9 N6 H3N 133.3(10) . . ? N5 N6 H3N 118.0(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 C6 C1 C2 C3 1.0(2) . . . . ? C8 C1 C2 C3 -177.76(15) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C2 C3 C4 C5 -1.2(3) . . . . ? C3 C4 C5 C6 0.1(2) . . . . ? C4 C5 C6 C1 1.5(2) . . . . ? C4 C5 C6 N1 -176.77(13) . . . . ? C2 C1 C6 C5 -2.1(2) . . . . ? C8 C1 C6 C5 176.87(11) . . . . ? C2 C1 C6 N1 176.46(12) . . . . ? C8 C1 C6 N1 -4.55(14) . . . . ? C2 C1 C8 N2 -46.8(2) . . . . ? C6 C1 C8 N2 134.36(11) . . . . ? C2 C1 C8 C9 78.85(17) . . . . ? C6 C1 C8 C9 -99.98(12) . . . . ? C2 C1 C8 C7 -172.30(14) . . . . ? C6 C1 C8 C7 8.86(12) . . . . ? O1 C7 C8 N2 42.84(16) . . . . ? N1 C7 C8 N2 -140.11(10) . . . . ? O1 C7 C8 C9 -72.91(14) . . . . ? N1 C7 C8 C9 104.13(11) . . . . ? O1 C7 C8 C1 172.53(11) . . . . ? N1 C7 C8 C1 -10.42(12) . . . . ? N2 C8 C9 N3 156.83(12) . . . . ? C1 C8 C9 N3 24.58(17) . . . . ? C7 C8 C9 N3 -83.38(14) . . . . ? N2 C8 C9 N6 -26.32(17) . . . . ? C1 C8 C9 N6 -158.58(12) . . . . ? C7 C8 C9 N6 93.46(14) . . . . ? C18 C13 C14 C15 0.1(2) . . . . ? N2 C13 C14 C15 177.03(14) . . . . ? C13 C14 C15 C16 0.7(3) . . . . ? C14 C15 C16 C17 -0.9(3) . . . . ? C15 C16 C17 C18 0.3(3) . . . . ? C14 C13 C18 C17 -0.7(2) . . . . ? N2 C13 C18 C17 -177.46(14) . . . . ? C16 C17 C18 C13 0.5(3) . . . . ? O1 C7 N1 C6 -174.56(12) . . . . ? C8 C7 N1 C6 8.51(13) . . . . ? C5 C6 N1 C7 175.71(13) . . . . ? C1 C6 N1 C7 -2.76(15) . . . . ? C18 C13 N2 C8 -47.92(18) . . . . ? C14 C13 N2 C8 135.29(13) . . . . ? C9 C8 N2 C13 -170.00(11) . . . . ? C1 C8 N2 C13 -42.91(16) . . . . ? C7 C8 N2 C13 76.93(14) . . . . ? N6 C9 N3 N4 0.27(15) . . . . ? C8 C9 N3 N4 177.58(12) . . . . ? C9 N3 N4 N5 -0.22(16) . . . . ? N3 N4 N5 N6 0.08(16) . . . . ? N3 C9 N6 N5 -0.23(15) . . . . ? C8 C9 N6 N5 -177.53(11) . . . . ? N4 N5 N6 C9 0.09(15) . . . . ? 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 N3 0.860(17) 2.159(17) 2.9770(15) 158.8(15) 2 N6 H3N O1 0.907(18) 1.832(18) 2.7095(14) 162.1(15) 3_565 N2 H2N N5 0.889(16) 2.691(16) 3.4818(17) 148.7(13) 3 N2 H2N N4 0.889(16) 2.553(17) 3.4404(17) 175.9(13) 3 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.172 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.064