# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2011 data_New_Global_Publ_Block _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 #TrackingRef 'BO1208.cif' _publ_section_related_literature ? # Added by publCIF - use a unique identifier for each data block #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Fu-Xue Chen' # Name of author for correspondence _publ_contact_author_address # Address of author for correspondence ; Department of Applied Chemistry, School of Chemical Engineering& the Environment Beijing Institute ofTechnology 5 SouthZhongguancun Street, Haidian district, Beijing 100081, China ; _publ_contact_author_email fuxue.chen@bit.edu.cn _publ_contact_author_fax +86-10-68918296 _publ_contact_author_phone +86-10-68918296 _publ_contact_letter ; Please consider this CIF for publication. I certify that this contibution is the original work of those listed as authors; that it has not been published before (in any language or medium) and is not being considered for publication elsewhere; that all authors concur with and are aware of the submission; that all workers involved in the study are listed as authors or given proper credit in the acknowledgements; that I have obtained permission for and acknowledged the source of any excerpts from other copyright works; and that to the best of my knowledge the paper contains no statements which are libellous, unlawful or in any way actionable. All coauthors have made significant scientific contributions to the work reported, including the ideas and their execution, and share responsibility and accountability for the results. ; _publ_requested_category ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Synthesis and Characteristics of Novel High-Nitrogen Heat-resistant Materials ; _publ_section_title_footnote # remove if not required . # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. # NB if using publCIF, the Author database tool might prove useful # (see the Tools menu in publCIF) loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Zhanda Fu' ; Department of Applied Chemistry, School of Chemical Engineering& the Environment Beijing Institute ofTechnology 5 SouthZhongguancun Street, Haidian district, Beijing 100081, China ; . 'Cheng He' ; Department of Applied Chemistry, School of Chemical Engineering& the Environment Beijing Institute ofTechnology 5 SouthZhongguancun Street, Haidian district, Beijing 100081, China ; . 'Fu-Xue Chen' ; Department of Applied Chemistry, School of Chemical Engineering& the Environment Beijing Institute ofTechnology 5 SouthZhongguancun Street, Haidian district, Beijing 100081, China ; . #============================================================================== # TEXT _publ_section_synopsis . _publ_section_abstract ; (type here to add abstract) ; _publ_section_comment ; The stucture of the title compound, (I), is shown below. Dimensions are available in the archived CIF. For related literature, see [type here to add references to related literature]. ; _publ_section_acknowledgements # remove if not required ; (type here to add acknowledgements) ; _publ_section_references ; ? ; _publ_section_figure_captions ; ; _publ_section_exptl_prep ; The crystal was obtained dy evaporation of ethycl acetate. ; _publ_section_exptl_refinement ; (type here to add refinement details) ; #============================================================================== _publ_manuscript_text # Used for convenience to store draft or replaced versions # of the abstract, comment etc. # Its contents will not be output ; ? ; #============================================================================== # Formatted by publCIF data_bo1208 _database_code_depnum_ccdc_archive 'CCDC 841480' #TrackingRef 'BO1208.cif' _audit_update_record ; 2011-08-24 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-nitro-5-methoxy-1,2,4-oxadiazole ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H7 N5 O2' _chemical_formula_weight 157.15 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 7.129(3) _cell_length_b 13.514(5) _cell_length_c 6.915(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.715(5) _cell_angle_gamma 90.00 _cell_volume 665.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 1978 _cell_measurement_theta_min 2.858 _cell_measurement_theta_max 29.102 _exptl_crystal_description Block _exptl_crystal_colour Pink _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.567 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.128 _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 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5660 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 29.10 _reflns_number_total 1753 _reflns_number_gt 1199 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0716P)^2^+0.3190P] 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 1753 _refine_ls_number_parameters 117 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1470 _refine_ls_wR_factor_gt 0.1355 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 0.15605(19) 0.83546(11) 0.3221(2) 0.0235(4) Uani 1 1 d . . . O2 O 0.1021(2) 0.58521(12) 0.3073(2) 0.0306(4) Uani 1 1 d . . . N1 N 0.0482(3) 0.75001(14) 0.2736(3) 0.0246(4) Uani 1 1 d . . . N2 N 0.3304(2) 0.70469(13) 0.4081(2) 0.0205(4) Uani 1 1 d . . . N3 N 0.4407(2) 0.87370(12) 0.4559(2) 0.0206(4) Uani 1 1 d . . . N4 N 0.6704(2) 0.75692(14) 0.5659(3) 0.0214(4) Uani 1 1 d . . . N5 N 0.7156(3) 0.92479(15) 0.5974(3) 0.0288(5) Uani 1 1 d . . . C1 C 0.1598(3) 0.67852(17) 0.3298(3) 0.0220(4) Uani 1 1 d . . . C2 C 0.3224(3) 0.80238(15) 0.4010(3) 0.0182(4) Uani 1 1 d . . . C3 C 0.6078(3) 0.84891(15) 0.5391(3) 0.0193(4) Uani 1 1 d . . . C4 C 0.2295(3) 0.50974(18) 0.3778(4) 0.0322(5) Uani 1 1 d . . . H4C H 0.3472 0.5140 0.3087 0.039 Uiso 1 1 calc R . . H4D H 0.1729 0.4444 0.3562 0.039 Uiso 1 1 calc R . . H4E H 0.2550 0.5194 0.5166 0.039 Uiso 1 1 calc R . . H4A H 0.778(4) 0.7539(18) 0.623(3) 0.020(6) Uiso 1 1 d . . . H4B H 0.602(4) 0.708(2) 0.529(4) 0.040(8) Uiso 1 1 d . . . H5A H 0.680(4) 0.984(2) 0.577(4) 0.043(9) Uiso 1 1 d . . . H5B H 0.819(5) 0.916(3) 0.638(5) 0.065(11) 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 O1 0.0159(7) 0.0248(8) 0.0292(8) -0.0019(6) -0.0068(6) -0.0007(6) O2 0.0238(8) 0.0233(8) 0.0443(10) 0.0023(7) -0.0074(7) -0.0040(6) N1 0.0186(8) 0.0258(10) 0.0291(9) -0.0025(7) -0.0050(7) -0.0066(7) N2 0.0162(8) 0.0209(9) 0.0241(8) 0.0000(7) -0.0031(6) -0.0015(6) N3 0.0187(8) 0.0173(8) 0.0255(9) -0.0005(7) -0.0057(6) 0.0012(6) N4 0.0138(8) 0.0194(9) 0.0306(9) -0.0019(7) -0.0081(7) 0.0011(6) N5 0.0187(10) 0.0214(10) 0.0454(12) -0.0008(9) -0.0149(8) -0.0009(7) C1 0.0190(10) 0.0256(11) 0.0214(9) -0.0009(8) -0.0009(7) -0.0070(8) C2 0.0112(9) 0.0240(11) 0.0191(9) 0.0002(8) -0.0015(7) 0.0028(7) C3 0.0170(9) 0.0203(10) 0.0204(9) -0.0008(8) -0.0019(7) 0.0006(7) C4 0.0329(13) 0.0230(12) 0.0403(13) 0.0022(10) -0.0029(10) -0.0022(9) _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 C2 1.366(2) . ? O1 N1 1.422(2) . ? O2 C1 1.334(3) . ? O2 C4 1.441(3) . ? N1 C1 1.303(3) . ? N2 C2 1.322(3) . ? N2 C1 1.363(3) . ? N3 C2 1.329(3) . ? N3 C3 1.350(3) . ? N4 C3 1.332(3) . ? N4 H4A 0.85(3) . ? N4 H4B 0.85(3) . ? N5 C3 1.336(3) . ? N5 H5A 0.85(3) . ? N5 H5B 0.79(4) . ? C4 H4C 0.9800 . ? C4 H4D 0.9800 . ? C4 H4E 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 N1 106.57(16) . . ? C1 O2 C4 116.16(17) . . ? C1 N1 O1 102.20(16) . . ? C2 N2 C1 101.95(17) . . ? C2 N3 C3 119.11(17) . . ? C3 N4 H4A 113.7(17) . . ? C3 N4 H4B 119.5(19) . . ? H4A N4 H4B 127(3) . . ? C3 N5 H5A 120(2) . . ? C3 N5 H5B 120(3) . . ? H5A N5 H5B 119(3) . . ? N1 C1 O2 118.88(18) . . ? N1 C1 N2 117.08(19) . . ? O2 C1 N2 124.0(2) . . ? N2 C2 N3 133.41(18) . . ? N2 C2 O1 112.20(17) . . ? N3 C2 O1 114.39(17) . . ? N4 C3 N5 119.13(19) . . ? N4 C3 N3 125.37(19) . . ? N5 C3 N3 115.50(18) . . ? O2 C4 H4C 109.5 . . ? O2 C4 H4D 109.5 . . ? H4C C4 H4D 109.5 . . ? O2 C4 H4E 109.5 . . ? H4C C4 H4E 109.5 . . ? H4D C4 H4E 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 O1 N1 C1 0.6(2) . . . . ? O1 N1 C1 O2 179.50(16) . . . . ? O1 N1 C1 N2 -0.7(2) . . . . ? C4 O2 C1 N1 -178.12(19) . . . . ? C4 O2 C1 N2 2.1(3) . . . . ? C2 N2 C1 N1 0.6(2) . . . . ? C2 N2 C1 O2 -179.65(19) . . . . ? C1 N2 C2 N3 179.1(2) . . . . ? C1 N2 C2 O1 -0.2(2) . . . . ? C3 N3 C2 N2 -0.5(3) . . . . ? C3 N3 C2 O1 178.74(16) . . . . ? N1 O1 C2 N2 -0.2(2) . . . . ? N1 O1 C2 N3 -179.66(16) . . . . ? C2 N3 C3 N4 2.7(3) . . . . ? C2 N3 C3 N5 -177.35(19) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 29.10 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.287 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.060 #============================================================================== # Formatted by publCIF data_bo1313 _database_code_depnum_ccdc_archive 'CCDC 841481' #TrackingRef 'BO1313.cif' _audit_update_record ; 2011-08-24 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,6-di(3-nitro-1,2,4-oxadiazole)-di(3-nitro-1,2,4-oxadiazole)-1,2,4,5-tetrazine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H30 N16 O10 S4' _chemical_formula_weight 734.80 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' S S 0.1246 0.1234 '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 5.750(2) _cell_length_b 8.875(3) _cell_length_c 15.739(6) _cell_angle_alpha 80.614(11) _cell_angle_beta 80.732(10) _cell_angle_gamma 81.456(10) _cell_volume 775.9(5) _cell_formula_units_Z 1 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2146 _cell_measurement_theta_min 2.650 _cell_measurement_theta_max 29.121 _exptl_crystal_description Prism _exptl_crystal_colour Pink _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 382 _exptl_absorpt_coefficient_mu 0.383 _exptl_absorpt_correction_type Multi-scans _exptl_absorpt_correction_T_min 0.8015 _exptl_absorpt_correction_T_max 0.9737 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8329 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 29.09 _reflns_number_total 4037 _reflns_number_gt 2672 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0539P)^2^+0.2690P] 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 4037 _refine_ls_number_parameters 279 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.0858 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1271 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.000 _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 0.5069(3) 0.8531(2) 0.89340(10) 0.0336(4) Uani 1 1 d . . . O2 O 1.1404(3) 0.6207(2) 0.93167(11) 0.0453(5) Uani 1 1 d . . . O3 O 1.1549(3) 0.5684(2) 0.80130(12) 0.0436(5) Uani 1 1 d . . . N1 N 0.7139(3) 0.7775(2) 0.92538(12) 0.0333(5) Uani 1 1 d . . . N2 N 0.7271(3) 0.7458(2) 0.78347(11) 0.0263(4) Uani 1 1 d . . . N3 N 0.3399(3) 0.8967(2) 0.76958(11) 0.0273(4) Uani 1 1 d . . . N4 N 0.1338(3) 0.9622(2) 0.65650(12) 0.0249(4) Uani 1 1 d . . . N5 N 0.2126(3) 0.9145(2) 0.51120(11) 0.0263(4) Uani 1 1 d . . . N6 N 0.1418(3) 0.9354(2) 0.43373(11) 0.0263(4) Uani 1 1 d . . . N7 N 0.5020(3) 0.8102(2) 0.63575(13) 0.0266(4) Uani 1 1 d . . . N8 N 1.0591(3) 0.6298(2) 0.86390(12) 0.0313(4) Uani 1 1 d . . . C1 C 0.8269(4) 0.7215(2) 0.85718(14) 0.0265(5) Uani 1 1 d . . . C2 C 0.5253(4) 0.8313(3) 0.80811(13) 0.0255(4) Uani 1 1 d . . . C3 C 0.3365(4) 0.8860(2) 0.68608(13) 0.0231(4) Uani 1 1 d . . . C4 C 0.0695(4) 0.9797(2) 0.57464(13) 0.0220(4) Uani 1 1 d . . . S1 S 0.77778(13) 0.65699(7) 0.38941(4) 0.03955(19) Uani 1 1 d . . . O4 O 0.7146(3) 0.7018(2) 0.47860(11) 0.0416(5) Uani 1 1 d . . . C5 C 0.8804(6) 0.4591(3) 0.4024(2) 0.0530(8) Uani 1 1 d . . . H5A H 1.0254 0.4407 0.4298 0.064 Uiso 1 1 calc R . . H5B H 0.9146 0.4236 0.3454 0.064 Uiso 1 1 calc R . . H5C H 0.7583 0.4025 0.4393 0.064 Uiso 1 1 calc R . . C6 C 0.5102(6) 0.6417(5) 0.3527(2) 0.0823(14) Uani 1 1 d . . . H6A H 0.4154 0.5763 0.3970 0.099 Uiso 1 1 calc R . . H6B H 0.5452 0.5960 0.2987 0.099 Uiso 1 1 calc R . . H6C H 0.4210 0.7443 0.3418 0.099 Uiso 1 1 calc R . . S2 S 0.0732(3) 0.8038(3) 1.16628(14) 0.0271(4) Uani 0.465(3) 1 d PD A 1 O5 O 0.178(2) 0.8913(13) 1.2203(7) 0.033(3) Uani 0.465(3) 1 d PD A 1 C7 C 0.3040(15) 0.6644(8) 1.1272(7) 0.0379(18) Uani 0.465(3) 1 d PD A 1 H7A H 0.4457 0.7143 1.1025 0.045 Uiso 0.465(3) 1 calc PR A 1 H7B H 0.2517 0.6181 1.0823 0.045 Uiso 0.465(3) 1 calc PR A 1 H7C H 0.3416 0.5841 1.1754 0.045 Uiso 0.465(3) 1 calc PR A 1 C8 C 0.0326(9) 0.9185(6) 1.0656(3) 0.0348(13) Uani 0.465(3) 1 d PD A 1 H8A H -0.0767 1.0116 1.0758 0.042 Uiso 0.465(3) 1 calc PR A 1 H8B H -0.0338 0.8600 1.0297 0.042 Uiso 0.465(3) 1 calc PR A 1 H8C H 0.1860 0.9474 1.0356 0.042 Uiso 0.465(3) 1 calc PR A 1 S2' S 0.1824(4) 0.8561(2) 1.12867(13) 0.0313(7) Uani 0.337(3) 1 d PD B 2 O5' O 0.207(3) 0.901(2) 1.2133(10) 0.024(3) Uani 0.337(3) 1 d PD B 2 C7' C 0.361(2) 0.6759(11) 1.1200(10) 0.0379(18) Uani 0.337(3) 1 d PD B 2 H7'1 H 0.5266 0.6868 1.1221 0.045 Uiso 0.337(3) 1 calc PR B 2 H7'2 H 0.3478 0.6425 1.0648 0.045 Uiso 0.337(3) 1 calc PR B 2 H7'3 H 0.3055 0.5993 1.1684 0.045 Uiso 0.337(3) 1 calc PR B 2 C8' C -0.0987(11) 0.7946(19) 1.1342(8) 0.049(2) Uani 0.337(3) 1 d PD B 2 H8'1 H -0.1246 0.7163 1.1853 0.059 Uiso 0.337(3) 1 calc PR B 2 H8'2 H -0.1049 0.7508 1.0815 0.059 Uiso 0.337(3) 1 calc PR B 2 H8'3 H -0.2226 0.8827 1.1391 0.059 Uiso 0.337(3) 1 calc PR B 2 S2" S 0.1542(9) 0.7606(5) 1.1896(3) 0.0346(11) Uani 0.198(4) 1 d PD C 3 O5" O 0.181(3) 0.894(2) 1.2319(13) 0.024(3) Uani 0.198(4) 1 d PD C 3 C7" C 0.3962(18) 0.7441(17) 1.1042(7) 0.0379(18) Uani 0.198(4) 1 d PD C 3 H7"1 H 0.4047 0.8438 1.0672 0.045 Uiso 0.198(4) 1 calc PR C 3 H7"2 H 0.3728 0.6671 1.0693 0.045 Uiso 0.198(4) 1 calc PR C 3 H7"3 H 0.5446 0.7122 1.1291 0.045 Uiso 0.198(4) 1 calc PR C 3 C8" C -0.078(2) 0.812(4) 1.1251(12) 0.049(2) Uani 0.198(4) 1 d PD C 3 H8"1 H -0.2312 0.8109 1.1626 0.059 Uiso 0.198(4) 1 calc PR C 3 H8"2 H -0.0645 0.7380 1.0840 0.059 Uiso 0.198(4) 1 calc PR C 3 H8"3 H -0.0662 0.9153 1.0928 0.059 Uiso 0.198(4) 1 calc PR C 3 H4N H 0.034(5) 1.002(3) 0.6930(18) 0.050(9) Uiso 1 1 d . . . H7A H 0.490(5) 0.811(3) 0.5853(18) 0.041(8) Uiso 1 1 d . . . H7B H 0.628(5) 0.771(3) 0.6560(16) 0.029(6) 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 O1 0.0298(9) 0.0478(10) 0.0246(8) -0.0120(7) -0.0102(7) 0.0056(7) O2 0.0400(10) 0.0636(13) 0.0340(9) -0.0067(9) -0.0219(8) 0.0053(9) O3 0.0376(10) 0.0512(11) 0.0434(10) -0.0204(9) -0.0135(8) 0.0134(8) N1 0.0281(10) 0.0443(12) 0.0285(10) -0.0091(9) -0.0113(8) 0.0040(8) N2 0.0273(10) 0.0281(10) 0.0250(9) -0.0065(7) -0.0092(7) 0.0002(7) N3 0.0272(10) 0.0322(10) 0.0238(9) -0.0089(8) -0.0098(7) 0.0046(8) N4 0.0244(9) 0.0275(10) 0.0225(9) -0.0067(8) -0.0067(7) 0.0047(7) N5 0.0266(10) 0.0282(10) 0.0249(9) -0.0071(8) -0.0087(7) 0.0031(7) N6 0.0283(10) 0.0279(10) 0.0233(9) -0.0067(7) -0.0089(7) 0.0036(7) N7 0.0235(10) 0.0340(11) 0.0225(10) -0.0075(8) -0.0082(8) 0.0046(8) N8 0.0292(10) 0.0335(11) 0.0323(10) -0.0048(9) -0.0119(8) 0.0003(8) C1 0.0260(11) 0.0278(11) 0.0274(11) -0.0043(9) -0.0100(9) -0.0012(9) C2 0.0292(11) 0.0282(11) 0.0207(10) -0.0072(8) -0.0053(8) -0.0029(9) C3 0.0242(11) 0.0228(10) 0.0235(10) -0.0040(8) -0.0073(8) -0.0018(8) C4 0.0235(10) 0.0218(10) 0.0218(10) -0.0043(8) -0.0063(8) -0.0017(8) S1 0.0529(4) 0.0331(3) 0.0305(3) -0.0090(3) 0.0011(3) -0.0010(3) O4 0.0442(11) 0.0482(11) 0.0323(9) -0.0190(8) -0.0086(8) 0.0127(8) C5 0.0619(19) 0.0491(17) 0.0541(17) -0.0277(14) -0.0320(15) 0.0222(14) C6 0.070(2) 0.118(3) 0.062(2) -0.055(2) -0.0457(18) 0.063(2) S2 0.0294(9) 0.0337(9) 0.0197(8) -0.0070(7) -0.0035(7) -0.0051(7) O5 0.021(4) 0.055(7) 0.028(6) -0.025(5) -0.006(3) 0.004(4) C7 0.042(4) 0.039(2) 0.033(2) -0.013(2) -0.006(3) 0.003(3) C8 0.037(3) 0.039(3) 0.030(3) -0.015(2) -0.015(2) 0.010(2) S2' 0.0423(13) 0.0308(10) 0.0227(11) -0.0010(8) -0.0103(9) -0.0073(8) O5' 0.029(5) 0.028(4) 0.014(6) -0.001(4) 0.000(4) -0.008(3) C7' 0.042(4) 0.039(2) 0.033(2) -0.013(2) -0.006(3) 0.003(3) C8' 0.044(3) 0.065(5) 0.046(4) -0.027(3) -0.021(3) 0.011(3) S2" 0.041(2) 0.039(2) 0.0229(19) -0.0068(16) -0.0061(16) 0.0023(17) O5" 0.029(5) 0.028(4) 0.014(6) -0.001(4) 0.000(4) -0.008(3) C7" 0.042(4) 0.039(2) 0.033(2) -0.013(2) -0.006(3) 0.003(3) C8" 0.044(3) 0.065(5) 0.046(4) -0.027(3) -0.021(3) 0.011(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 O1 C2 1.372(3) . ? O1 N1 1.402(2) . ? O2 N8 1.219(2) . ? O3 N8 1.217(2) . ? N1 C1 1.294(3) . ? N2 C2 1.327(3) . ? N2 C1 1.348(3) . ? N3 C2 1.323(3) . ? N3 C3 1.337(3) . ? N4 C3 1.368(3) . ? N4 C4 1.375(3) . ? N4 H4N 0.83(3) . ? N5 N6 1.323(2) . ? N5 C4 1.338(3) . ? N6 C4 1.345(3) 2_576 ? N7 C3 1.314(3) . ? N7 H7A 0.81(3) . ? N7 H7B 0.84(3) . ? N8 C1 1.467(3) . ? C4 N6 1.345(3) 2_576 ? S1 O4 1.4951(17) . ? S1 C5 1.757(3) . ? S1 C6 1.759(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? S2 O5 1.485(5) . ? S2 C8 1.767(5) . ? S2 C7 1.779(4) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? S2' O5' 1.483(6) . ? S2' C8' 1.766(6) . ? S2' C7' 1.779(4) . ? C7' H7'1 0.9800 . ? C7' H7'2 0.9800 . ? C7' H7'3 0.9800 . ? C8' H8'1 0.9800 . ? C8' H8'2 0.9800 . ? C8' H8'3 0.9800 . ? S2" O5" 1.484(6) . ? S2" C8" 1.767(6) . ? S2" C7" 1.779(4) . ? C7" H7"1 0.9800 . ? C7" H7"2 0.9800 . ? C7" H7"3 0.9800 . ? C8" H8"1 0.9800 . ? C8" H8"2 0.9800 . ? C8" H8"3 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 N1 107.61(16) . . ? C1 N1 O1 100.72(17) . . ? C2 N2 C1 100.59(17) . . ? C2 N3 C3 120.14(18) . . ? C3 N4 C4 129.14(18) . . ? C3 N4 H4N 116(2) . . ? C4 N4 H4N 115(2) . . ? N6 N5 C4 117.66(17) . . ? N5 N6 C4 117.05(17) . 2_576 ? C3 N7 H7A 120(2) . . ? C3 N7 H7B 117.7(16) . . ? H7A N7 H7B 121(3) . . ? O3 N8 O2 125.2(2) . . ? O3 N8 C1 117.30(18) . . ? O2 N8 C1 117.49(19) . . ? N1 C1 N2 119.62(19) . . ? N1 C1 N8 118.15(19) . . ? N2 C1 N8 122.22(19) . . ? N3 C2 N2 134.5(2) . . ? N3 C2 O1 114.07(18) . . ? N2 C2 O1 111.45(18) . . ? N7 C3 N3 126.0(2) . . ? N7 C3 N4 121.62(19) . . ? N3 C3 N4 112.33(18) . . ? N5 C4 N6 125.29(19) . 2_576 ? N5 C4 N4 120.28(18) . . ? N6 C4 N4 114.43(18) 2_576 . ? O4 S1 C5 106.89(13) . . ? O4 S1 C6 107.11(13) . . ? C5 S1 C6 96.35(16) . . ? S1 C5 H5A 109.5 . . ? S1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? S1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? S1 C6 H6A 109.5 . . ? S1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? S1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O5 S2 C8 109.6(6) . . ? O5 S2 C7 107.0(3) . . ? C8 S2 C7 98.2(4) . . ? O5' S2' C8' 109.9(7) . . ? O5' S2' C7' 107.2(4) . . ? C8' S2' C7' 98.3(4) . . ? S2' C7' H7'1 109.5 . . ? S2' C7' H7'2 109.5 . . ? H7'1 C7' H7'2 109.5 . . ? S2' C7' H7'3 109.5 . . ? H7'1 C7' H7'3 109.5 . . ? H7'2 C7' H7'3 109.5 . . ? S2' C8' H8'1 109.5 . . ? S2' C8' H8'2 109.5 . . ? H8'1 C8' H8'2 109.5 . . ? S2' C8' H8'3 109.5 . . ? H8'1 C8' H8'3 109.5 . . ? H8'2 C8' H8'3 109.5 . . ? O5" S2" C8" 109.7(7) . . ? O5" S2" C7" 107.0(4) . . ? C8" S2" C7" 98.2(4) . . ? 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 C2 O1 N1 C1 -0.1(2) . . . . ? C4 N5 N6 C4 -0.3(3) . . . 2_576 ? O1 N1 C1 N2 -0.8(3) . . . . ? O1 N1 C1 N8 -179.37(19) . . . . ? C2 N2 C1 N1 1.2(3) . . . . ? C2 N2 C1 N8 179.8(2) . . . . ? O3 N8 C1 N1 174.7(2) . . . . ? O2 N8 C1 N1 -5.1(3) . . . . ? O3 N8 C1 N2 -3.9(3) . . . . ? O2 N8 C1 N2 176.3(2) . . . . ? C3 N3 C2 N2 -2.3(4) . . . . ? C3 N3 C2 O1 179.13(19) . . . . ? C1 N2 C2 N3 -179.8(3) . . . . ? C1 N2 C2 O1 -1.2(2) . . . . ? N1 O1 C2 N3 179.77(19) . . . . ? N1 O1 C2 N2 0.8(3) . . . . ? C2 N3 C3 N7 2.2(3) . . . . ? C2 N3 C3 N4 -179.0(2) . . . . ? C4 N4 C3 N7 -2.7(4) . . . . ? C4 N4 C3 N3 178.4(2) . . . . ? N6 N5 C4 N6 0.3(4) . . . 2_576 ? N6 N5 C4 N4 -179.89(19) . . . . ? C3 N4 C4 N5 1.4(3) . . . . ? C3 N4 C4 N6 -178.8(2) . . . 2_576 ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 29.09 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.595 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.062