# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_shrv77 _database_code_depnum_ccdc_archive 'CCDC 861470' #TrackingRef 'shrv77-final.cif' _audit_creation_date 2009-09-28 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; 2-(1H-tetrazol-1-yl)acetic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C3 H4 N4 O2' _chemical_formula_sum 'C3 H4 N4 O2' _chemical_formula_weight 128.10 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 12.4884(7) _cell_length_b 5.0947(3) _cell_length_c 17.4942(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.9410(10) _cell_angle_gamma 90.00 _cell_volume 1096.35(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'thick needle' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.6774 _exptl_absorpt_correction_T_max 0.7454 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8688 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2252 _reflns_number_gt 1873 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2009.3-0 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 v2009.3-0 (Bruker, 2006)' _computing_data_reduction ; Bruker SAINT v7.60A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_structure_refinement 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_molecular_graphics 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_publication_material 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _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^)+(0.0420P)^2^+0.2884P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2252 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0891 _refine_ls_wR_factor_gt 0.0835 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 N1A N -0.73305(10) 0.1783(3) 0.09501(8) 0.0550(4) Uani 1 1 d . . . N2A N -0.67875(10) 0.0900(3) 0.04017(7) 0.0462(3) Uani 1 1 d . . . N3A N -0.58588(9) 0.2061(3) 0.04409(7) 0.0427(3) Uani 1 1 d . . . N4A N -0.57924(8) 0.3753(2) 0.10288(6) 0.0300(3) Uani 1 1 d . . . C5A C -0.66853(11) 0.3539(4) 0.13349(9) 0.0471(4) Uani 1 1 d . . . H5AA H -0.6833 0.4489 0.1759 0.056 Uiso 1 1 calc R . . C6A C -0.48095(10) 0.5260(3) 0.12893(7) 0.0339(3) Uani 1 1 d . . . H6AA H -0.4997 0.6919 0.1505 0.041 Uiso 1 1 calc R . . H6AB H -0.4452 0.5633 0.0851 0.041 Uiso 1 1 calc R . . C7A C -0.40443(10) 0.3748(3) 0.18986(7) 0.0326(3) Uani 1 1 d . . . O8A O -0.31618(7) 0.5110(2) 0.21328(6) 0.0469(3) Uani 1 1 d . . . H8AA H -0.2753 0.4273 0.2462 0.070 Uiso 1 1 calc R . . O9A O -0.42460(8) 0.1613(2) 0.21253(6) 0.0519(3) Uani 1 1 d . . . N1B N -0.15594(9) 0.2377(3) 0.29995(7) 0.0402(3) Uani 1 1 d . . . N2B N -0.12316(10) 0.0172(3) 0.26686(7) 0.0462(3) Uani 1 1 d . . . N3B N -0.02632(10) -0.0451(3) 0.29936(7) 0.0425(3) Uani 1 1 d . . . N4B N 0.00493(8) 0.1358(2) 0.35501(6) 0.0309(3) Uani 1 1 d . . . C5B C -0.07526(10) 0.3068(3) 0.35427(8) 0.0332(3) Uani 1 1 d . . . H5BA H -0.0743 0.4513 0.3868 0.040 Uiso 1 1 calc R . . C6B C 0.11508(10) 0.1357(3) 0.39893(9) 0.0374(3) Uani 1 1 d . . . H6BA H 0.1227 0.2780 0.4363 0.045 Uiso 1 1 calc R . . H6BB H 0.1660 0.1662 0.3638 0.045 Uiso 1 1 calc R . . C7B C 0.14248(11) -0.1206(3) 0.44110(8) 0.0347(3) Uani 1 1 d . . . O8B O 0.24887(8) -0.1533(2) 0.45555(7) 0.0515(3) Uani 1 1 d . . . H8BA H 0.2634 -0.2928 0.4784 0.077 Uiso 1 1 calc R . . O9B O 0.07721(8) -0.2696(2) 0.45967(6) 0.0474(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 N1A 0.0432(7) 0.0707(10) 0.0509(8) -0.0114(7) 0.0070(6) -0.0223(7) N2A 0.0457(7) 0.0426(7) 0.0462(7) -0.0094(6) -0.0037(5) -0.0098(6) N3A 0.0412(7) 0.0462(7) 0.0388(6) -0.0128(6) 0.0019(5) -0.0035(6) N4A 0.0277(5) 0.0319(6) 0.0280(5) -0.0018(4) -0.0016(4) -0.0021(4) C5A 0.0346(7) 0.0636(11) 0.0438(8) -0.0161(7) 0.0093(6) -0.0111(7) C6A 0.0306(6) 0.0361(8) 0.0326(7) 0.0035(6) -0.0013(5) -0.0069(6) C7A 0.0277(6) 0.0380(8) 0.0308(6) -0.0001(6) 0.0015(5) -0.0010(6) O8A 0.0319(5) 0.0510(7) 0.0512(6) 0.0056(5) -0.0112(4) -0.0062(5) O9A 0.0445(6) 0.0461(7) 0.0591(7) 0.0190(5) -0.0075(5) -0.0050(5) N1B 0.0282(6) 0.0466(8) 0.0436(7) -0.0012(6) -0.0004(5) 0.0008(5) N2B 0.0409(7) 0.0473(8) 0.0464(7) -0.0082(6) -0.0035(5) -0.0046(6) N3B 0.0434(7) 0.0364(7) 0.0454(7) -0.0087(6) 0.0010(5) 0.0008(5) N4B 0.0285(5) 0.0278(6) 0.0344(6) -0.0001(5) 0.0004(4) 0.0012(4) C5B 0.0286(6) 0.0336(7) 0.0363(7) 0.0000(6) 0.0024(5) 0.0022(5) C6B 0.0284(7) 0.0298(7) 0.0500(8) 0.0053(6) -0.0042(6) 0.0009(5) C7B 0.0356(7) 0.0291(7) 0.0363(7) -0.0011(6) -0.0027(5) 0.0019(6) O8B 0.0353(5) 0.0416(6) 0.0724(7) 0.0196(5) -0.0054(5) 0.0057(5) O9B 0.0447(6) 0.0383(6) 0.0570(7) 0.0117(5) 0.0024(5) -0.0035(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 N1A C5A 1.3096(19) . ? N1A N2A 1.3444(19) . ? N2A N3A 1.2931(17) . ? N3A N4A 1.3335(16) . ? N4A C5A 1.3222(17) . ? N4A C6A 1.4530(16) . ? C5A H5AA 0.9300 . ? C6A C7A 1.5136(17) . ? C6A H6AA 0.9700 . ? C6A H6AB 0.9700 . ? C7A O9A 1.1993(17) . ? C7A O8A 1.3068(16) . ? O8A H8AA 0.8200 . ? N1B C5B 1.3082(17) . ? N1B N2B 1.3587(18) . ? N2B N3B 1.2844(17) . ? N3B N4B 1.3487(16) . ? N4B C5B 1.3255(17) . ? N4B C6B 1.4552(16) . ? C5B H5BA 0.9300 . ? C6B C7B 1.5096(19) . ? C6B H6BA 0.9700 . ? C6B H6BB 0.9700 . ? C7B O9B 1.1990(17) . ? C7B O8B 1.3195(16) . ? O8B H8BA 0.8200 . ? 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 C5A N1A N2A 104.71(12) . . ? N3A N2A N1A 111.56(12) . . ? N2A N3A N4A 105.79(11) . . ? C5A N4A N3A 108.34(11) . . ? C5A N4A C6A 129.97(12) . . ? N3A N4A C6A 121.35(11) . . ? N1A C5A N4A 109.58(13) . . ? N1A C5A H5AA 125.2 . . ? N4A C5A H5AA 125.2 . . ? N4A C6A C7A 110.39(11) . . ? N4A C6A H6AA 109.6 . . ? C7A C6A H6AA 109.6 . . ? N4A C6A H6AB 109.6 . . ? C7A C6A H6AB 109.6 . . ? H6AA C6A H6AB 108.1 . . ? O9A C7A O8A 126.27(12) . . ? O9A C7A C6A 123.46(12) . . ? O8A C7A C6A 110.27(12) . . ? C7A O8A H8AA 109.5 . . ? C5B N1B N2B 106.32(11) . . ? N3B N2B N1B 110.24(11) . . ? N2B N3B N4B 106.46(11) . . ? C5B N4B N3B 108.55(11) . . ? C5B N4B C6B 130.48(12) . . ? N3B N4B C6B 120.67(11) . . ? N1B C5B N4B 108.43(12) . . ? N1B C5B H5BA 125.8 . . ? N4B C5B H5BA 125.8 . . ? N4B C6B C7B 111.86(11) . . ? N4B C6B H6BA 109.2 . . ? C7B C6B H6BA 109.2 . . ? N4B C6B H6BB 109.2 . . ? C7B C6B H6BB 109.2 . . ? H6BA C6B H6BB 107.9 . . ? O9B C7B O8B 125.26(13) . . ? O9B C7B C6B 124.93(12) . . ? O8B C7B C6B 109.80(12) . . ? C7B O8B H8BA 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 C5A N1A N2A N3A -0.46(19) . . . . ? N1A N2A N3A N4A -0.16(17) . . . . ? N2A N3A N4A C5A 0.72(16) . . . . ? N2A N3A N4A C6A 174.64(12) . . . . ? N2A N1A C5A N4A 0.90(19) . . . . ? N3A N4A C5A N1A -1.04(18) . . . . ? C6A N4A C5A N1A -174.26(13) . . . . ? C5A N4A C6A C7A 83.85(18) . . . . ? N3A N4A C6A C7A -88.61(15) . . . . ? N4A C6A C7A O9A -0.32(19) . . . . ? N4A C6A C7A O8A -179.89(11) . . . . ? C5B N1B N2B N3B -0.29(16) . . . . ? N1B N2B N3B N4B 0.40(16) . . . . ? N2B N3B N4B C5B -0.36(15) . . . . ? N2B N3B N4B C6B -174.73(12) . . . . ? N2B N1B C5B N4B 0.05(15) . . . . ? N3B N4B C5B N1B 0.19(15) . . . . ? C6B N4B C5B N1B 173.82(13) . . . . ? C5B N4B C6B C7B 128.40(15) . . . . ? N3B N4B C6B C7B -58.63(17) . . . . ? N4B C6B C7B O9B -24.1(2) . . . . ? N4B C6B C7B O8B 157.02(12) . . . . ? 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 O8A H8AA N1B 0.82 1.89 2.6822(15) 163.6 . O8B H8BA N2A 0.82 1.93 2.7382(16) 169.8 4_656 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.153 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.036 data_cnu935 _database_code_depnum_ccdc_archive 'CCDC 899437' #TrackingRef 'web_deposit_cif_file_0_Young-HyukJoo_1358438524.compound5 - 899437.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; guanidinium 1-methoxy-5-nitroiminotetrazolate ; _chemical_name_common 'guanidinium 1-methoxy-5-nitroiminotetrazolate' _chemical_melting_point ? _chemical_formula_moiety '3(C2 H3 N6 O3), 3(C H6 N3), H2 O' _chemical_formula_sum 'C9 H29 N27 O10' _chemical_formula_weight 675.59 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5920(4) _cell_length_b 13.7908(8) _cell_length_c 15.7389(9) _cell_angle_alpha 114.474(2) _cell_angle_beta 100.4090(10) _cell_angle_gamma 90.831(5) _cell_volume 1467.75(14) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9033 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 27.00 _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 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.133 _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 296(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 SMART CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28334 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 28.28 _reflns_number_total 7254 _reflns_number_gt 4988 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0701P)^2^] 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 0.0125(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7254 _refine_ls_number_parameters 496 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1287 _refine_ls_wR_factor_gt 0.1192 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.001 _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 0.71999(17) 0.47247(10) 0.89739(9) 0.0408(3) Uani 1 1 d . . . N2 N 0.63825(16) 0.55371(9) 0.88637(8) 0.0481(3) Uani 1 1 d . . . N3 N 0.59212(19) 0.53361(11) 0.79403(9) 0.0619(4) Uani 1 1 d . . . N4 N 0.6462(2) 0.44088(11) 0.74967(9) 0.0638(4) Uani 1 1 d . . . N5 N 0.72602(17) 0.40008(9) 0.81033(8) 0.0526(3) Uani 1 1 d . . . N6 N 0.77676(15) 0.48382(8) 0.98874(7) 0.0429(3) Uani 1 1 d . . . N7 N 0.85113(15) 0.40286(8) 0.99959(8) 0.0443(3) Uani 1 1 d . . . O8 O 0.86308(16) 0.31642(8) 0.93198(7) 0.0649(3) Uani 1 1 d . . . O9 O 0.91167(15) 0.41667(8) 1.08340(7) 0.0565(3) Uani 1 1 d . . . O10 O 0.59260(14) 0.64314(8) 0.95498(7) 0.0550(3) Uani 1 1 d . . . C11 C 0.7109(3) 0.73586(12) 0.97454(13) 0.0680(5) Uani 1 1 d . . . H11A H 0.6761 0.7978 1.0231 0.102 Uiso 1 1 calc R . . H11B H 0.7030 0.7464 0.9174 0.102 Uiso 1 1 calc R . . H11C H 0.8325 0.7251 0.9962 0.102 Uiso 1 1 calc R . . N12 N 0.8739(2) 0.03199(10) 0.59489(9) 0.0514(3) Uani 1 1 d . . . H12A H 0.947(2) -0.0115(13) 0.6100(12) 0.060(5) Uiso 1 1 d . . . H12B H 0.810(2) 0.0150(13) 0.5414(14) 0.064(5) Uiso 1 1 d . . . C13 C 0.85460(19) 0.12439(10) 0.66377(9) 0.0430(3) Uani 1 1 d . . . N14 N 0.9439(2) 0.15247(12) 0.75239(9) 0.0544(3) Uani 1 1 d . . . H14A H 1.014(2) 0.1128(15) 0.7673(13) 0.068(6) Uiso 1 1 d . . . H14B H 0.928(2) 0.2145(14) 0.7952(12) 0.062(5) Uiso 1 1 d . . . N15 N 0.7472(2) 0.18985(11) 0.64514(12) 0.0599(4) Uani 1 1 d . . . H15A H 0.691(3) 0.1736(16) 0.5887(16) 0.085(7) Uiso 1 1 d . . . H15B H 0.736(3) 0.2468(16) 0.6930(14) 0.076(6) Uiso 1 1 d . . . C16 C 0.35406(18) 0.10630(10) 0.28870(9) 0.0407(3) Uani 1 1 d . . . N17 N 0.24639(17) 0.08026(9) 0.20225(8) 0.0515(3) Uani 1 1 d . . . N18 N 0.16614(19) 0.16399(11) 0.19885(9) 0.0587(3) Uani 1 1 d . . . N19 N 0.22377(19) 0.24125(10) 0.28156(9) 0.0587(3) Uani 1 1 d . . . N20 N 0.33950(18) 0.20882(9) 0.33935(8) 0.0513(3) Uani 1 1 d . . . N21 N 0.44793(16) 0.02906(9) 0.30250(8) 0.0461(3) Uani 1 1 d . . . N22 N 0.53794(16) 0.05410(9) 0.39049(8) 0.0461(3) Uani 1 1 d . . . O23 O 0.53808(17) 0.14298(9) 0.45720(7) 0.0678(3) Uani 1 1 d . . . O24 O 0.62281(16) -0.01673(9) 0.40318(8) 0.0611(3) Uani 1 1 d . . . O25 O 0.20042(17) -0.02027(9) 0.13083(7) 0.0705(3) Uani 1 1 d . . . C26 C 0.2669(4) -0.0306(2) 0.04956(13) 0.1058(8) Uani 1 1 d . . . H26A H 0.2379 -0.1028 0.0015 0.159 Uiso 1 1 calc R . . H26B H 0.3952 -0.0138 0.0668 0.159 Uiso 1 1 calc R . . H26C H 0.2129 0.0177 0.0252 0.159 Uiso 1 1 calc R . . N27 N -0.2681(2) 0.75305(11) 0.32736(9) 0.0533(3) Uani 1 1 d . . . H27A H -0.325(2) 0.8028(14) 0.3203(12) 0.063(5) Uiso 1 1 d . . . H27B H -0.209(2) 0.7603(13) 0.3791(12) 0.054(5) Uiso 1 1 d . . . C28 C -0.23233(18) 0.67195(11) 0.25199(9) 0.0430(3) Uani 1 1 d . . . N29 N -0.30832(19) 0.65916(12) 0.16530(9) 0.0532(3) Uani 1 1 d . . . H29A H -0.280(2) 0.6109(14) 0.1161(13) 0.062(5) Uiso 1 1 d . . . H29B H -0.379(2) 0.7094(15) 0.1625(13) 0.068(5) Uiso 1 1 d . . . N30 N -0.1241(2) 0.60319(12) 0.26383(11) 0.0576(4) Uani 1 1 d . . . H30A H -0.093(2) 0.5566(14) 0.2171(13) 0.061(5) Uiso 1 1 d . . . H30B H -0.069(3) 0.6113(14) 0.3188(14) 0.071(5) Uiso 1 1 d . . . C31 C 0.16642(18) 0.82837(11) 0.68082(9) 0.0409(3) Uani 1 1 d . . . N32 N 0.25853(16) 0.83810(9) 0.76618(8) 0.0460(3) Uani 1 1 d . . . N33 N 0.26085(19) 0.93747(10) 0.83327(8) 0.0565(3) Uani 1 1 d . . . N34 N 0.17131(19) 0.98787(10) 0.78938(9) 0.0587(3) Uani 1 1 d . . . N35 N 0.10905(17) 0.92283(9) 0.69478(8) 0.0498(3) Uani 1 1 d . . . N36 N 0.15737(16) 0.73117(9) 0.60459(8) 0.0461(3) Uani 1 1 d . . . N37 N 0.06722(17) 0.72437(10) 0.52264(8) 0.0481(3) Uani 1 1 d . . . O38 O -0.01516(17) 0.79637(9) 0.51228(8) 0.0659(3) Uani 1 1 d . . . O39 O 0.06739(17) 0.63646(9) 0.45195(7) 0.0662(3) Uani 1 1 d . . . O40 O 0.34442(14) 0.76213(8) 0.78708(7) 0.0541(3) Uani 1 1 d . . . C41 C 0.2230(2) 0.70367(13) 0.81473(12) 0.0621(4) Uani 1 1 d . . . H41A H 0.2852 0.6509 0.8298 0.093 Uiso 1 1 calc R . . H41B H 0.1220 0.6689 0.7630 0.093 Uiso 1 1 calc R . . H41C H 0.1816 0.7525 0.8696 0.093 Uiso 1 1 calc R . . N42 N 0.4228(2) 0.37391(11) 0.53871(10) 0.0566(4) Uani 1 1 d . . . H42A H 0.418(2) 0.3174(15) 0.4846(13) 0.066(5) Uiso 1 1 d . . . H42B H 0.498(3) 0.3799(14) 0.5882(14) 0.068(5) Uiso 1 1 d . . . C43 C 0.3391(2) 0.45633(11) 0.53706(9) 0.0452(3) Uani 1 1 d . . . N44 N 0.3591(2) 0.54723(11) 0.61476(9) 0.0598(4) Uani 1 1 d . . . H44A H 0.308(2) 0.6000(13) 0.6104(11) 0.055(5) Uiso 1 1 d . . . H44B H 0.440(3) 0.5506(16) 0.6634(15) 0.086(6) Uiso 1 1 d . . . N45 N 0.23407(19) 0.44968(11) 0.45780(10) 0.0559(3) Uani 1 1 d . . . H45A H 0.183(2) 0.5092(15) 0.4621(12) 0.064(5) Uiso 1 1 d . . . H45B H 0.228(2) 0.3903(15) 0.4002(14) 0.073(5) Uiso 1 1 d . . . O46 O 0.5234(2) 0.18118(11) 0.84072(11) 0.0781(4) Uani 1 1 d . . . H46A H 0.641(4) 0.2084(19) 0.8670(18) 0.110(8) Uiso 1 1 d . . . H46B H 0.526(3) 0.1192(17) 0.7971(15) 0.081(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 C1 0.0405(7) 0.0355(6) 0.0368(6) 0.0071(5) 0.0052(5) 0.0027(5) N2 0.0547(7) 0.0465(6) 0.0346(6) 0.0107(5) 0.0041(5) 0.0110(5) N3 0.0728(9) 0.0661(9) 0.0379(6) 0.0173(6) 0.0012(6) 0.0143(7) N4 0.0760(9) 0.0644(9) 0.0367(6) 0.0109(6) 0.0031(6) 0.0099(7) N5 0.0602(8) 0.0467(7) 0.0363(6) 0.0047(5) 0.0067(5) 0.0052(6) N6 0.0533(7) 0.0346(6) 0.0352(5) 0.0099(4) 0.0071(5) 0.0073(5) N7 0.0474(6) 0.0345(6) 0.0427(6) 0.0095(5) 0.0067(5) 0.0016(5) O8 0.0821(8) 0.0373(5) 0.0533(6) 0.0020(5) 0.0030(5) 0.0149(5) O9 0.0751(7) 0.0511(6) 0.0445(6) 0.0227(5) 0.0089(5) 0.0092(5) O10 0.0659(7) 0.0471(6) 0.0478(5) 0.0143(5) 0.0151(5) 0.0197(5) C11 0.0883(13) 0.0454(9) 0.0636(10) 0.0168(8) 0.0148(9) 0.0107(8) N12 0.0706(9) 0.0404(7) 0.0361(6) 0.0109(5) 0.0066(6) 0.0138(6) C13 0.0532(8) 0.0337(6) 0.0393(7) 0.0114(5) 0.0129(6) 0.0000(6) N14 0.0708(9) 0.0443(7) 0.0380(6) 0.0097(6) 0.0067(6) 0.0014(7) N15 0.0774(10) 0.0409(7) 0.0507(8) 0.0105(6) 0.0087(7) 0.0160(7) C16 0.0448(7) 0.0410(7) 0.0336(6) 0.0118(5) 0.0113(5) 0.0029(6) N17 0.0631(8) 0.0470(7) 0.0354(6) 0.0094(5) 0.0080(5) 0.0115(6) N18 0.0676(9) 0.0599(8) 0.0476(7) 0.0220(6) 0.0102(6) 0.0196(7) N19 0.0697(9) 0.0497(7) 0.0533(7) 0.0188(6) 0.0110(6) 0.0154(6) N20 0.0616(8) 0.0418(6) 0.0433(6) 0.0122(5) 0.0078(5) 0.0086(5) N21 0.0549(7) 0.0414(6) 0.0366(6) 0.0119(5) 0.0078(5) 0.0076(5) N22 0.0541(7) 0.0409(6) 0.0404(6) 0.0156(5) 0.0068(5) 0.0003(5) O23 0.0971(9) 0.0463(6) 0.0413(6) 0.0073(5) -0.0033(6) 0.0105(6) O24 0.0732(7) 0.0498(6) 0.0584(6) 0.0253(5) 0.0024(5) 0.0115(5) O25 0.0913(9) 0.0575(7) 0.0429(6) 0.0056(5) 0.0055(6) 0.0041(6) C26 0.152(2) 0.1051(17) 0.0437(10) 0.0111(10) 0.0295(12) 0.0260(16) N27 0.0678(9) 0.0518(8) 0.0349(6) 0.0136(6) 0.0086(6) 0.0128(7) C28 0.0461(8) 0.0434(7) 0.0361(6) 0.0142(6) 0.0076(5) 0.0004(6) N29 0.0626(8) 0.0555(8) 0.0335(6) 0.0120(6) 0.0070(6) 0.0137(7) N30 0.0710(9) 0.0556(8) 0.0390(7) 0.0145(6) 0.0068(7) 0.0175(7) C31 0.0426(7) 0.0449(7) 0.0385(7) 0.0210(6) 0.0086(5) 0.0044(6) N32 0.0535(7) 0.0473(6) 0.0373(6) 0.0190(5) 0.0069(5) 0.0052(5) N33 0.0675(8) 0.0530(7) 0.0401(6) 0.0126(6) 0.0083(6) -0.0012(6) N34 0.0724(9) 0.0478(7) 0.0499(7) 0.0150(6) 0.0128(6) 0.0041(6) N35 0.0583(7) 0.0442(6) 0.0470(7) 0.0193(5) 0.0107(6) 0.0063(5) N36 0.0541(7) 0.0473(6) 0.0359(6) 0.0189(5) 0.0029(5) 0.0090(5) N37 0.0565(7) 0.0491(7) 0.0389(6) 0.0203(5) 0.0055(5) 0.0108(6) O38 0.0853(8) 0.0593(7) 0.0478(6) 0.0230(5) -0.0015(5) 0.0263(6) O39 0.0955(9) 0.0551(6) 0.0365(5) 0.0127(5) 0.0019(5) 0.0222(6) O40 0.0543(6) 0.0673(7) 0.0481(6) 0.0331(5) 0.0068(5) 0.0136(5) C41 0.0804(12) 0.0596(9) 0.0597(9) 0.0338(8) 0.0249(8) 0.0158(8) N42 0.0800(10) 0.0418(7) 0.0389(7) 0.0119(6) 0.0023(7) 0.0151(6) C43 0.0556(8) 0.0403(7) 0.0385(7) 0.0149(6) 0.0106(6) 0.0079(6) N44 0.0842(10) 0.0462(8) 0.0390(7) 0.0111(6) 0.0050(7) 0.0207(7) N45 0.0709(9) 0.0450(7) 0.0428(7) 0.0139(6) 0.0014(6) 0.0135(6) O46 0.0705(9) 0.0450(7) 0.0936(10) 0.0059(7) 0.0141(7) 0.0120(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N5 1.3293(16) . ? C1 N2 1.3463(17) . ? C1 N6 1.3657(17) . ? N2 N3 1.3384(16) . ? N2 O10 1.3607(14) . ? N3 N4 1.2924(18) . ? N4 N5 1.3570(19) . ? N6 N7 1.3175(15) . ? N7 O8 1.2443(13) . ? N7 O9 1.2481(15) . ? O10 C11 1.441(2) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? N12 C13 1.3188(17) . ? N12 H12A 0.898(18) . ? N12 H12B 0.829(19) . ? C13 N15 1.311(2) . ? C13 N14 1.3258(19) . ? N14 H14A 0.843(19) . ? N14 H14B 0.871(18) . ? N15 H15A 0.85(2) . ? N15 H15B 0.85(2) . ? C16 N20 1.3227(17) . ? C16 N17 1.3540(17) . ? C16 N21 1.3592(17) . ? N17 N18 1.3294(17) . ? N17 O25 1.3639(15) . ? N18 N19 1.2856(17) . ? N19 N20 1.3634(18) . ? N21 N22 1.3263(16) . ? N22 O23 1.2402(14) . ? N22 O24 1.2420(15) . ? O25 C26 1.413(2) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? N27 C28 1.3259(18) . ? N27 H27A 0.851(18) . ? N27 H27B 0.822(17) . ? C28 N30 1.3123(19) . ? C28 N29 1.3186(18) . ? N29 H29A 0.853(18) . ? N29 H29B 0.893(19) . ? N30 H30A 0.827(17) . ? N30 H30B 0.85(2) . ? C31 N35 1.3224(18) . ? C31 N32 1.3492(17) . ? C31 N36 1.3698(17) . ? N32 N33 1.3367(16) . ? N32 O40 1.3634(15) . ? N33 N34 1.2900(18) . ? N34 N35 1.3681(17) . ? N36 N37 1.3114(16) . ? N37 O38 1.2324(15) . ? N37 O39 1.2612(15) . ? O40 C41 1.450(2) . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? N42 C43 1.3173(19) . ? N42 H42A 0.878(18) . ? N42 H42B 0.852(19) . ? C43 N45 1.3208(19) . ? C43 N44 1.3218(17) . ? N44 H44A 0.851(17) . ? N44 H44B 0.88(2) . ? N45 H45A 0.894(18) . ? N45 H45B 0.929(19) . ? O46 H46A 0.91(3) . ? O46 H46B 0.85(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 N5 C1 N2 106.46(12) . . ? N5 C1 N6 136.74(13) . . ? N2 C1 N6 116.78(11) . . ? N3 N2 C1 110.90(11) . . ? N3 N2 O10 121.12(12) . . ? C1 N2 O10 127.84(11) . . ? N4 N3 N2 104.53(12) . . ? N3 N4 N5 112.29(12) . . ? C1 N5 N4 105.82(12) . . ? N7 N6 C1 116.89(10) . . ? O8 N7 O9 120.11(12) . . ? O8 N7 N6 123.70(11) . . ? O9 N7 N6 116.19(10) . . ? N2 O10 C11 111.01(12) . . ? O10 C11 H11A 109.5 . . ? O10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 N12 H12A 118.1(10) . . ? C13 N12 H12B 117.7(12) . . ? H12A N12 H12B 123.9(16) . . ? N15 C13 N12 120.21(14) . . ? N15 C13 N14 119.25(14) . . ? N12 C13 N14 120.54(15) . . ? C13 N14 H14A 122.2(13) . . ? C13 N14 H14B 117.1(11) . . ? H14A N14 H14B 120.7(17) . . ? C13 N15 H15A 120.4(14) . . ? C13 N15 H15B 115.8(13) . . ? H15A N15 H15B 123.7(19) . . ? N20 C16 N17 105.54(12) . . ? N20 C16 N21 136.39(12) . . ? N17 C16 N21 118.05(11) . . ? N18 N17 C16 111.24(11) . . ? N18 N17 O25 121.77(12) . . ? C16 N17 O25 126.32(12) . . ? N19 N18 N17 105.08(12) . . ? N18 N19 N20 111.50(12) . . ? C16 N20 N19 106.64(11) . . ? N22 N21 C16 116.41(11) . . ? O23 N22 O24 121.16(12) . . ? O23 N22 N21 122.45(12) . . ? O24 N22 N21 116.39(11) . . ? N17 O25 C26 110.98(15) . . ? O25 C26 H26A 109.5 . . ? O25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 N27 H27A 120.0(12) . . ? C28 N27 H27B 115.3(12) . . ? H27A N27 H27B 122.4(17) . . ? N30 C28 N29 120.07(13) . . ? N30 C28 N27 119.89(14) . . ? N29 C28 N27 120.02(14) . . ? C28 N29 H29A 121.2(11) . . ? C28 N29 H29B 115.4(12) . . ? H29A N29 H29B 122.9(16) . . ? C28 N30 H30A 119.7(12) . . ? C28 N30 H30B 122.0(12) . . ? H30A N30 H30B 117.4(17) . . ? N35 C31 N32 106.49(12) . . ? N35 C31 N36 136.28(13) . . ? N32 C31 N36 117.21(12) . . ? N33 N32 C31 110.84(12) . . ? N33 N32 O40 121.18(11) . . ? C31 N32 O40 127.96(11) . . ? N34 N33 N32 104.94(11) . . ? N33 N34 N35 111.70(12) . . ? C31 N35 N34 106.03(12) . . ? N37 N36 C31 115.72(11) . . ? O38 N37 O39 120.30(11) . . ? O38 N37 N36 124.38(12) . . ? O39 N37 N36 115.32(11) . . ? N32 O40 C41 110.20(11) . . ? O40 C41 H41A 109.5 . . ? O40 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? O40 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C43 N42 H42A 118.5(12) . . ? C43 N42 H42B 120.7(12) . . ? H42A N42 H42B 119.6(17) . . ? N42 C43 N45 120.63(13) . . ? N42 C43 N44 120.53(14) . . ? N45 C43 N44 118.84(14) . . ? C43 N44 H44A 118.1(11) . . ? C43 N44 H44B 115.5(14) . . ? H44A N44 H44B 125.3(18) . . ? C43 N45 H45A 115.4(11) . . ? C43 N45 H45B 121.0(11) . . ? H45A N45 H45B 122.9(16) . . ? H46A O46 H46B 105.9(19) . . ? 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 N12 H12A N35 0.898(18) 2.133(18) 2.992(2) 159.7(14) 1_645 N12 H12A O38 0.898(18) 2.504(17) 3.1516(17) 129.4(13) 1_645 N12 H12B O24 0.829(19) 2.24(2) 3.0650(19) 174.5(16) . N14 H14A N34 0.843(19) 2.22(2) 3.053(2) 171.3(17) 1_645 N14 H14A N35 0.843(19) 2.561(19) 3.251(2) 139.9(16) 1_645 N14 H14B O8 0.871(18) 2.178(18) 2.9748(17) 152.1(15) . N15 H15A O23 0.85(2) 2.05(2) 2.8942(19) 175(2) . N15 H15B N5 0.85(2) 2.17(2) 3.0183(19) 174.3(18) . N15 H15B N4 0.85(2) 2.59(2) 3.331(2) 145.6(16) . N27 H27A O24 0.851(18) 2.362(18) 3.0795(18) 142.3(15) 1_465 N27 H27B O38 0.822(17) 2.192(18) 3.0038(18) 169.7(16) . N29 H29A N6 0.853(18) 2.167(18) 3.0188(17) 176.5(16) 1_454 N29 H29B O46 0.893(19) 1.89(2) 2.783(2) 178.3(18) 2_566 N30 H30A O9 0.827(17) 2.195(18) 3.0003(18) 164.5(16) 1_454 N30 H30B O39 0.85(2) 2.05(2) 2.8967(18) 177.8(18) . N42 H42A N20 0.878(18) 2.114(19) 2.9581(18) 161.0(16) . N42 H42A O23 0.878(18) 2.481(18) 3.1073(17) 128.8(14) . N42 H42B N4 0.852(19) 2.37(2) 3.1832(19) 161.0(16) . N44 H44A N36 0.851(17) 2.180(18) 3.028(2) 174.5(16) . N44 H44B N3 0.88(2) 2.27(2) 3.126(2) 164.9(19) . N45 H45A O39 0.894(18) 2.026(19) 2.9144(18) 171.9(16) . N45 H45B N19 0.929(19) 2.12(2) 3.0449(19) 171.2(16) . N45 H45B N20 0.929(19) 2.502(19) 3.2611(19) 139.0(15) . O46 H46A O8 0.91(3) 2.04(3) 2.914(2) 160(2) . O46 H46B N21 0.85(2) 2.04(2) 2.8836(17) 175.7(19) 2_656 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.551 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.057 data_cnu936 _database_code_depnum_ccdc_archive 'CCDC 899438' #TrackingRef 'web_deposit_cif_file_1_Young-HyukJoo_1358438524.compound6 - 899438.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; aminoguanidinium 1-methoxy-5-nitroiminotetrazolate ; _chemical_name_common 'aminoguanidinium 1-methoxy-5-nitroiminotetrazolate' _chemical_melting_point ? _chemical_formula_moiety 'C2 H3 N6 O3, C H7 N4' _chemical_formula_sum 'C3 H10 N10 O3' _chemical_formula_weight 234.21 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 C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.1247(6) _cell_length_b 9.7122(3) _cell_length_c 13.4618(8) _cell_angle_alpha 90.00 _cell_angle_beta 119.073(2) _cell_angle_gamma 90.00 _cell_volume 1956.84(15) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4594 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 23.20 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.19 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_max 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.137 _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 296(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 SMART CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23975 _diffrn_reflns_av_R_equivalents 0.0722 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 28.33 _reflns_number_total 2422 _reflns_number_gt 1355 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0619P)^2^+0.3555P] 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 2422 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0859 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1241 _refine_ls_wR_factor_gt 0.1044 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 0.53576(11) 0.46384(17) 0.14339(13) 0.0411(4) Uani 1 1 d . . . N2 N 0.61591(10) 0.40290(16) 0.18090(12) 0.0489(4) Uani 1 1 d . . . N3 N 0.68194(11) 0.49444(19) 0.22970(15) 0.0621(5) Uani 1 1 d . . . N4 N 0.64234(11) 0.61095(19) 0.22211(15) 0.0654(5) Uani 1 1 d . . . N5 N 0.55162(10) 0.59599(16) 0.16873(13) 0.0522(4) Uani 1 1 d . . . N6 N 0.46247(9) 0.37985(14) 0.09628(12) 0.0487(4) Uani 1 1 d . . . N7 N 0.38430(10) 0.44093(15) 0.05134(11) 0.0446(4) Uani 1 1 d . . . O8 O 0.37347(8) 0.56723(13) 0.04481(12) 0.0608(4) Uani 1 1 d . . . O9 O 0.31782(8) 0.36102(13) 0.01238(12) 0.0610(4) Uani 1 1 d . . . O10 O 0.63277(9) 0.27083(14) 0.16351(11) 0.0626(4) Uani 1 1 d . . . C11 C 0.63560(16) 0.1816(2) 0.25021(19) 0.0727(6) Uani 1 1 d . . . H11A H 0.6475 0.0891 0.2364 0.109 Uiso 1 1 calc R . . H11B H 0.5792 0.1847 0.2491 0.109 Uiso 1 1 calc R . . H11C H 0.6820 0.2115 0.3231 0.109 Uiso 1 1 calc R . . N12 N 0.10919(13) 0.4080(2) 0.03962(18) 0.0612(5) Uani 1 1 d . . . H12A H 0.0918(16) 0.322(3) 0.008(2) 0.095(9) Uiso 1 1 d . . . H12B H 0.1470(17) 0.393(3) 0.116(2) 0.093(9) Uiso 1 1 d . . . N13 N 0.15715(12) 0.47217(17) -0.00789(15) 0.0582(4) Uani 1 1 d . . . H13 H 0.2111(18) 0.435(3) 0.003(2) 0.097(8) Uiso 1 1 d . . . C14 C 0.12687(12) 0.58726(18) -0.06767(15) 0.0480(4) Uani 1 1 d . . . N15 N 0.17648(13) 0.6449(2) -0.10745(17) 0.0627(5) Uani 1 1 d . . . H15A H 0.2359(18) 0.619(3) -0.081(2) 0.097(9) Uiso 1 1 d . . . H15B H 0.1591(15) 0.723(3) -0.147(2) 0.084(8) Uiso 1 1 d . . . N16 N 0.04878(11) 0.63673(19) -0.09040(16) 0.0568(5) Uani 1 1 d . . . H16A H 0.0361(13) 0.716(2) -0.1130(16) 0.058(6) Uiso 1 1 d . . . H16B H 0.0170(15) 0.599(2) -0.058(2) 0.079(8) 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 0.0453(10) 0.0436(10) 0.0342(8) 0.0029(7) 0.0191(7) 0.0052(7) N2 0.0451(8) 0.0506(9) 0.0480(9) -0.0014(7) 0.0203(7) 0.0063(7) N3 0.0459(9) 0.0699(12) 0.0634(11) -0.0035(9) 0.0209(8) -0.0040(8) N4 0.0534(10) 0.0636(11) 0.0705(12) -0.0076(9) 0.0233(9) -0.0090(8) N5 0.0501(9) 0.0478(9) 0.0544(9) -0.0028(7) 0.0220(7) -0.0018(7) N6 0.0405(8) 0.0438(8) 0.0524(9) 0.0012(7) 0.0152(7) 0.0037(6) N7 0.0461(8) 0.0443(8) 0.0396(8) 0.0029(6) 0.0178(7) 0.0033(7) O8 0.0524(8) 0.0421(7) 0.0750(9) 0.0048(6) 0.0207(7) 0.0084(6) O9 0.0434(7) 0.0523(8) 0.0748(9) -0.0049(7) 0.0190(7) -0.0046(6) O10 0.0700(9) 0.0614(9) 0.0571(8) -0.0007(7) 0.0315(7) 0.0197(7) C11 0.0791(15) 0.0580(12) 0.0684(14) 0.0086(11) 0.0260(12) 0.0180(11) N12 0.0696(12) 0.0527(11) 0.0637(12) 0.0062(9) 0.0344(10) 0.0122(9) N13 0.0572(10) 0.0511(9) 0.0656(11) 0.0086(8) 0.0292(9) 0.0129(8) C14 0.0452(10) 0.0412(9) 0.0447(10) -0.0072(8) 0.0115(8) 0.0022(8) N15 0.0574(11) 0.0539(11) 0.0731(12) 0.0075(9) 0.0287(10) 0.0037(9) N16 0.0517(11) 0.0433(10) 0.0658(11) 0.0059(8) 0.0211(9) 0.0090(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N5 1.322(2) . ? C1 N2 1.348(2) . ? C1 N6 1.367(2) . ? N2 N3 1.334(2) . ? N2 O10 1.3598(19) . ? N3 N4 1.298(2) . ? N4 N5 1.366(2) . ? N6 N7 1.3126(19) . ? N7 O8 1.2373(18) . ? N7 O9 1.2622(18) . ? O10 C11 1.435(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? N12 N13 1.408(2) . ? N12 H12A 0.92(3) . ? N12 H12B 0.92(3) . ? N13 C14 1.327(2) . ? N13 H13 0.93(3) . ? C14 N16 1.310(2) . ? C14 N15 1.328(3) . ? N15 H15A 0.93(3) . ? N15 H15B 0.89(3) . ? N16 H16A 0.82(2) . ? N16 H16B 0.92(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 N5 C1 N2 106.59(15) . . ? N5 C1 N6 136.57(16) . . ? N2 C1 N6 116.75(15) . . ? N3 N2 C1 110.93(15) . . ? N3 N2 O10 120.91(15) . . ? C1 N2 O10 127.78(15) . . ? N4 N3 N2 104.89(15) . . ? N3 N4 N5 111.47(15) . . ? C1 N5 N4 106.12(15) . . ? N7 N6 C1 116.41(14) . . ? O8 N7 O9 120.41(14) . . ? O8 N7 N6 124.40(15) . . ? O9 N7 N6 115.19(14) . . ? N2 O10 C11 110.82(15) . . ? O10 C11 H11A 109.5 . . ? O10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N13 N12 H12A 109.0(16) . . ? N13 N12 H12B 109.0(16) . . ? H12A N12 H12B 105(2) . . ? C14 N13 N12 120.41(17) . . ? C14 N13 H13 118.9(16) . . ? N12 N13 H13 120.7(16) . . ? N16 C14 N13 120.3(2) . . ? N16 C14 N15 122.11(19) . . ? N13 C14 N15 117.50(18) . . ? C14 N15 H15A 121.2(16) . . ? C14 N15 H15B 120.3(15) . . ? H15A N15 H15B 117(2) . . ? C14 N16 H16A 119.3(14) . . ? C14 N16 H16B 120.9(15) . . ? H16A N16 H16B 116(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 N12 H12A N6 0.92(3) 2.33(3) 3.238(3) 172(2) 7 N12 H12A O9 0.92(3) 2.46(3) 3.119(2) 128.9(19) 7 N13 H13 O9 0.93(3) 1.91(3) 2.843(2) 175(2) . N15 H15A O8 0.93(3) 2.19(3) 3.071(2) 157(2) . N15 H15B N4 0.89(3) 2.30(3) 3.150(3) 159(2) 8_465 N16 H16A N5 0.82(2) 2.25(2) 3.008(2) 154.4(19) 7_565 N16 H16A O8 0.82(2) 2.51(2) 3.102(2) 130.5(17) 7_565 N16 H16B N12 0.92(2) 2.30(2) 3.126(3) 150(2) 5_565 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.163 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.042 data_test4_0m _database_code_depnum_ccdc_archive 'CCDC 899439' #TrackingRef 'web_deposit_cif_file_2_Young-HyukJoo_1358438524.compound7 - 899439.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; diaminoguanidinium 1-methoxy-5-nitroiminotetrazolate ; _chemical_name_common 'diaminoguanidinium 1-methoxy-5-nitroiminotetrazolate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H11 N11 O3' _chemical_formula_weight 249.23 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 6.5764(12) _cell_length_b 9.2377(17) _cell_length_c 9.8647(18) _cell_angle_alpha 105.849(4) _cell_angle_beta 100.993(4) _cell_angle_gamma 103.370(4) _cell_volume 539.86(17) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3874 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 28.32 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.131 _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 296(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6313 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1964 _reflns_number_gt 1793 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0912P)^2^+0.2828P] 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 0.059(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1964 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1600 _refine_ls_wR_factor_gt 0.1560 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.005 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 0.3564(3) 0.1503(2) 0.6618(2) 0.0324(5) Uani 1 1 d . . . N2 N 0.3891(3) 0.1172(2) 0.78650(18) 0.0363(4) Uani 1 1 d . . . N3 N 0.4879(3) 0.2600(2) 0.89694(19) 0.0438(5) Uani 1 1 d . . . N4 N 0.5163(3) 0.3761(2) 0.8462(2) 0.0469(5) Uani 1 1 d . . . N5 N 0.4333(3) 0.3097(2) 0.7006(2) 0.0403(5) Uani 1 1 d . . . N6 N 0.2696(3) 0.0674(2) 0.51621(18) 0.0387(5) Uani 1 1 d . . . N7 N 0.2040(3) -0.0884(2) 0.48045(18) 0.0378(5) Uani 1 1 d . . . O8 O 0.2142(3) -0.15929(18) 0.57114(18) 0.0504(5) Uani 1 1 d . . . O9 O 0.1271(3) -0.1627(2) 0.34563(18) 0.0597(5) Uani 1 1 d . . . O10 O 0.4429(3) 0.3984(2) 0.6108(2) 0.0552(5) Uani 1 1 d . . . C11 C 0.2618(5) 0.4630(3) 0.5996(4) 0.0679(8) Uani 1 1 d . . . H11A H 0.1281 0.3790 0.5689 0.102 Uiso 1 1 calc R . . H11B H 0.2640 0.5170 0.5292 0.102 Uiso 1 1 calc R . . H11C H 0.2734 0.5358 0.6933 0.102 Uiso 1 1 calc R . . N12 N 0.3531(3) 0.1348(3) 0.2328(2) 0.0501(5) Uani 1 1 d . . . H12A H 0.4221 0.1926 0.1911 0.060 Uiso 1 1 calc R . . H12B H 0.4206 0.0901 0.2843 0.060 Uiso 1 1 calc R . . N13 N 0.1311(3) 0.1137(2) 0.2169(2) 0.0481(5) Uani 1 1 d . . . H13 H 0.0609 0.0561 0.2583 0.058 Uiso 1 1 calc R . . C14 C 0.0303(3) 0.1842(2) 0.1367(2) 0.0334(5) Uani 1 1 d . . . N15 N 0.1395(3) 0.2600(2) 0.06440(19) 0.0386(5) Uani 1 1 d . . . H15 H 0.2725 0.2629 0.0696 0.046 Uiso 1 1 calc R . . N16 N 0.0376(3) 0.3353(2) -0.0205(2) 0.0460(5) Uani 1 1 d . . . H16A H -0.0954 0.3322 -0.0256 0.055 Uiso 1 1 calc R . . H16B H 0.1080 0.3847 -0.0677 0.055 Uiso 1 1 calc R . . N17 N -0.1757(3) 0.1740(3) 0.1264(2) 0.0510(6) Uani 1 1 d . . . H17A H -0.2413 0.2170 0.0720 0.061 Uiso 1 1 calc R . . H17B H -0.2444 0.1243 0.1741 0.061 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 C1 0.0292(10) 0.0381(10) 0.0374(10) 0.0190(8) 0.0136(8) 0.0127(8) N2 0.0367(9) 0.0414(9) 0.0340(9) 0.0168(7) 0.0101(7) 0.0124(7) N3 0.0426(10) 0.0498(11) 0.0373(10) 0.0141(8) 0.0101(8) 0.0117(8) N4 0.0457(11) 0.0447(10) 0.0445(11) 0.0115(8) 0.0128(8) 0.0062(8) N5 0.0463(10) 0.0376(9) 0.0427(10) 0.0205(8) 0.0173(8) 0.0106(8) N6 0.0459(10) 0.0411(10) 0.0347(9) 0.0183(7) 0.0128(7) 0.0151(8) N7 0.0330(9) 0.0445(10) 0.0351(9) 0.0132(7) 0.0082(7) 0.0111(7) O8 0.0572(10) 0.0407(9) 0.0486(9) 0.0213(7) 0.0038(7) 0.0070(7) O9 0.0671(12) 0.0600(11) 0.0365(9) 0.0065(8) 0.0078(8) 0.0066(9) O10 0.0660(11) 0.0495(9) 0.0667(11) 0.0370(9) 0.0291(9) 0.0183(8) C11 0.0663(17) 0.0533(15) 0.093(2) 0.0420(15) 0.0158(15) 0.0181(13) N12 0.0397(10) 0.0710(13) 0.0607(13) 0.0430(11) 0.0195(9) 0.0259(9) N13 0.0399(10) 0.0654(12) 0.0594(12) 0.0436(10) 0.0209(9) 0.0206(9) C14 0.0346(10) 0.0357(10) 0.0323(10) 0.0138(8) 0.0113(8) 0.0101(8) N15 0.0316(9) 0.0490(10) 0.0451(10) 0.0280(8) 0.0135(7) 0.0134(7) N16 0.0384(10) 0.0584(12) 0.0539(12) 0.0370(10) 0.0134(8) 0.0154(9) N17 0.0368(10) 0.0753(14) 0.0615(13) 0.0443(11) 0.0222(9) 0.0218(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 C1 N2 1.337(3) . ? C1 N5 1.357(3) . ? C1 N6 1.364(3) . ? N2 N3 1.378(3) . ? N3 N4 1.293(3) . ? N4 N5 1.342(3) . ? N5 O10 1.362(2) . ? N6 N7 1.327(3) . ? N7 O8 1.245(2) . ? N7 O9 1.257(2) . ? O10 C11 1.449(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? N12 N13 1.400(3) . ? N12 H12A 0.8600 . ? N12 H12B 0.8600 . ? N13 C14 1.331(3) . ? N13 H13 0.8600 . ? C14 N17 1.318(3) . ? C14 N15 1.323(2) . ? N15 N16 1.398(2) . ? N15 H15 0.8600 . ? N16 H16A 0.8600 . ? N16 H16B 0.8600 . ? N17 H17A 0.8600 . ? N17 H17B 0.8600 . ? 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 N2 C1 N5 106.12(17) . . ? N2 C1 N6 136.71(18) . . ? N5 C1 N6 117.17(17) . . ? C1 N2 N3 105.99(16) . . ? N4 N3 N2 111.64(17) . . ? N3 N4 N5 105.25(17) . . ? N4 N5 C1 110.99(17) . . ? N4 N5 O10 121.14(17) . . ? C1 N5 O10 127.77(18) . . ? N7 N6 C1 116.04(16) . . ? O8 N7 O9 121.06(18) . . ? O8 N7 N6 123.90(17) . . ? O9 N7 N6 115.04(17) . . ? N5 O10 C11 110.72(19) . . ? O10 C11 H11A 109.5 . . ? O10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N13 N12 H12A 120.0 . . ? N13 N12 H12B 120.0 . . ? H12A N12 H12B 120.0 . . ? C14 N13 N12 118.86(17) . . ? C14 N13 H13 120.6 . . ? N12 N13 H13 120.6 . . ? N17 C14 N15 121.11(18) . . ? N17 C14 N13 120.32(18) . . ? N15 C14 N13 118.54(18) . . ? C14 N15 N16 119.68(17) . . ? C14 N15 H15 120.2 . . ? N16 N15 H15 120.2 . . ? N15 N16 H16A 120.0 . . ? N15 N16 H16B 120.0 . . ? H16A N16 H16B 120.0 . . ? C14 N17 H17A 120.0 . . ? C14 N17 H17B 120.0 . . ? H17A N17 H17B 120.0 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.494 _refine_diff_density_min -0.526 _refine_diff_density_rms 0.054 data_cnu912 _database_code_depnum_ccdc_archive 'CCDC 899440' #TrackingRef 'web_deposit_cif_file_3_Young-HyukJoo_1358438524.compound8 - 899440.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; triaminoguanidinium 1-methoxy-5-nitroiminotetrazolate ; _chemical_name_common 'triaminoguanidinium 1-methoxy-5-nitroiminotetrazolate' _chemical_melting_point ? _chemical_formula_moiety 'C H9 N6, C2 H3 N6 O3' _chemical_formula_sum 'C3 H12 N12 O3' _chemical_formula_weight 264.25 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.93360(10) _cell_length_b 7.97080(10) _cell_length_c 10.6766(2) _cell_angle_alpha 103.9800(10) _cell_angle_beta 97.668(3) _cell_angle_gamma 100.9850(10) _cell_volume 552.022(15) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6261 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 27.93 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.16 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_max 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.136 _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 296(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 SMART CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14907 _diffrn_reflns_av_R_equivalents 0.0576 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 28.35 _reflns_number_total 2746 _reflns_number_gt 2194 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0589P)^2^+0.0090P] 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 0.086(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2746 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.1032 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.115 _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 0.24060(15) 0.96459(13) 0.32994(10) 0.0353(2) Uani 1 1 d . . . N2 N 0.29737(14) 1.08411(13) 0.44939(9) 0.0422(2) Uani 1 1 d . . . N3 N 0.26505(16) 1.00628(16) 0.54489(10) 0.0518(3) Uani 1 1 d . . . N4 N 0.18770(16) 0.84051(15) 0.48442(10) 0.0517(3) Uani 1 1 d . . . N5 N 0.16829(15) 0.80868(13) 0.35107(10) 0.0446(3) Uani 1 1 d . . . N6 N 0.27322(14) 1.02786(12) 0.22492(9) 0.0409(2) Uani 1 1 d . . . N7 N 0.20221(14) 0.91614(11) 0.10733(9) 0.0383(2) Uani 1 1 d . . . O8 O 0.10741(13) 0.76035(10) 0.09012(8) 0.0499(2) Uani 1 1 d . . . O9 O 0.23591(16) 0.97447(12) 0.01237(9) 0.0595(3) Uani 1 1 d . . . O10 O 0.38800(12) 1.25968(11) 0.47796(9) 0.0514(2) Uani 1 1 d . . . C11 C 0.24085(19) 1.36389(16) 0.47085(13) 0.0510(3) Uani 1 1 d . . . H11A H 0.3068 1.4872 0.4912 0.076 Uiso 1 1 calc R . . H11B H 0.1556 1.3474 0.5328 0.076 Uiso 1 1 calc R . . H11C H 0.1619 1.3266 0.3837 0.076 Uiso 1 1 calc R . . C12 C 0.46264(15) 0.49783(13) 0.81998(9) 0.0324(2) Uani 1 1 d . . . N13 N 0.64297(14) 0.47271(13) 0.85326(10) 0.0421(2) Uani 1 1 d . . . H13 H 0.645(2) 0.371(2) 0.8667(13) 0.052(4) Uiso 1 1 d . . . N14 N 0.81026(15) 0.58685(15) 0.83380(12) 0.0469(3) Uani 1 1 d . . . H14A H 0.883(2) 0.628(2) 0.9116(16) 0.056(4) Uiso 1 1 d . . . H14B H 0.863(2) 0.516(2) 0.7780(15) 0.066(5) Uiso 1 1 d . . . N15 N 0.44204(14) 0.64453(12) 0.78794(10) 0.0385(2) Uani 1 1 d . . . H15 H 0.540(2) 0.7208(19) 0.7946(14) 0.049(4) Uiso 1 1 d . . . N16 N 0.24941(14) 0.67614(13) 0.76271(11) 0.0417(2) Uani 1 1 d . . . H16A H 0.244(2) 0.774(2) 0.8303(15) 0.059(4) Uiso 1 1 d . . . H16B H 0.238(2) 0.707(2) 0.6852(16) 0.070(5) Uiso 1 1 d . . . N17 N 0.30415(16) 0.37514(12) 0.82213(10) 0.0411(2) Uani 1 1 d . . . H17 H 0.194(2) 0.3831(18) 0.8012(14) 0.051(4) Uiso 1 1 d . . . N18 N 0.34131(17) 0.21836(14) 0.84801(12) 0.0483(3) Uani 1 1 d . . . H18A H 0.289(2) 0.203(2) 0.9190(16) 0.074(5) Uiso 1 1 d . . . H18B H 0.300(2) 0.134(2) 0.7743(16) 0.066(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0333(5) 0.0320(5) 0.0390(6) 0.0089(4) 0.0072(4) 0.0045(4) N2 0.0421(5) 0.0395(5) 0.0400(5) 0.0078(4) 0.0055(4) 0.0031(4) N3 0.0542(6) 0.0626(7) 0.0414(6) 0.0181(5) 0.0098(5) 0.0143(5) N4 0.0570(6) 0.0573(6) 0.0485(6) 0.0253(5) 0.0168(5) 0.0131(5) N5 0.0503(6) 0.0385(5) 0.0471(6) 0.0172(4) 0.0133(4) 0.0054(4) N6 0.0524(6) 0.0291(4) 0.0380(5) 0.0080(4) 0.0119(4) 0.0012(4) N7 0.0454(5) 0.0315(4) 0.0397(5) 0.0113(4) 0.0086(4) 0.0104(4) O8 0.0611(5) 0.0322(4) 0.0465(5) 0.0097(3) -0.0064(4) -0.0001(4) O9 0.0945(7) 0.0488(5) 0.0427(5) 0.0199(4) 0.0244(5) 0.0174(5) O10 0.0415(4) 0.0382(4) 0.0594(5) -0.0006(4) 0.0014(4) -0.0028(3) C11 0.0541(7) 0.0414(6) 0.0517(7) 0.0060(5) 0.0101(6) 0.0058(5) C12 0.0398(5) 0.0305(5) 0.0255(5) 0.0058(4) 0.0063(4) 0.0068(4) N13 0.0417(5) 0.0383(5) 0.0486(6) 0.0172(4) 0.0049(4) 0.0106(4) N14 0.0363(5) 0.0468(6) 0.0539(7) 0.0134(5) 0.0020(5) 0.0061(4) N15 0.0332(5) 0.0320(5) 0.0514(6) 0.0160(4) 0.0066(4) 0.0049(4) N16 0.0400(5) 0.0385(5) 0.0495(6) 0.0132(4) 0.0093(4) 0.0143(4) N17 0.0420(5) 0.0350(5) 0.0498(6) 0.0186(4) 0.0108(4) 0.0067(4) N18 0.0653(7) 0.0339(5) 0.0501(6) 0.0191(5) 0.0157(5) 0.0087(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N5 1.3322(13) . ? C1 N2 1.3509(14) . ? C1 N6 1.3639(14) . ? N2 N3 1.3373(14) . ? N2 O10 1.3615(12) . ? N3 N4 1.2945(16) . ? N4 N5 1.3678(14) . ? N6 N7 1.3189(13) . ? N7 O9 1.2443(11) . ? N7 O8 1.2467(11) . ? O10 C11 1.4386(16) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N13 1.3194(14) . ? C12 N15 1.3223(13) . ? C12 N17 1.3314(14) . ? N13 N14 1.4035(13) . ? N13 H13 0.862(14) . ? N14 H14A 0.863(16) . ? N14 H14B 0.886(17) . ? N15 N16 1.4089(13) . ? N15 H15 0.801(15) . ? N16 H16A 0.937(16) . ? N16 H16B 0.919(16) . ? N17 N18 1.4053(13) . ? N17 H17 0.787(14) . ? N18 H18A 0.907(16) . ? N18 H18B 0.874(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 C1 N2 106.29(10) . . ? N5 C1 N6 137.39(10) . . ? N2 C1 N6 116.30(9) . . ? N3 N2 C1 111.07(10) . . ? N3 N2 O10 121.05(10) . . ? C1 N2 O10 127.76(10) . . ? N4 N3 N2 104.87(10) . . ? N3 N4 N5 111.86(10) . . ? C1 N5 N4 105.91(9) . . ? N7 N6 C1 116.73(9) . . ? O9 N7 O8 120.96(9) . . ? O9 N7 N6 116.12(9) . . ? O8 N7 N6 122.92(9) . . ? N2 O10 C11 110.41(8) . . ? O10 C11 H11A 109.5 . . ? O10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N13 C12 N15 119.96(9) . . ? N13 C12 N17 118.78(9) . . ? N15 C12 N17 121.24(10) . . ? C12 N13 N14 119.55(9) . . ? C12 N13 H13 114.9(9) . . ? N14 N13 H13 123.6(9) . . ? N13 N14 H14A 102.8(10) . . ? N13 N14 H14B 104.1(10) . . ? H14A N14 H14B 113.1(14) . . ? C12 N15 N16 119.34(9) . . ? C12 N15 H15 119.3(10) . . ? N16 N15 H15 120.6(10) . . ? N15 N16 H16A 106.9(9) . . ? N15 N16 H16B 106.8(10) . . ? H16A N16 H16B 108.2(14) . . ? C12 N17 N18 116.80(10) . . ? C12 N17 H17 122.3(10) . . ? N18 N17 H17 120.4(10) . . ? N17 N18 H18A 108.9(10) . . ? N17 N18 H18B 106.8(11) . . ? H18A N18 H18B 118.0(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 N13 H13 N18 0.862(14) 2.179(13) 2.6049(14) 110.2(11) . N13 H13 O8 0.862(14) 2.226(14) 2.8810(13) 132.8(12) 2_666 N14 H14A O8 0.863(16) 2.186(17) 3.0377(15) 168.8(13) 1_656 N14 H14B N5 0.886(17) 2.573(17) 3.3328(16) 144.3(13) 2_666 N15 H15 N6 0.801(15) 2.242(15) 3.0028(12) 158.9(14) 2_676 N16 H16A O9 0.937(16) 2.213(16) 3.1396(14) 169.8(13) 1_556 N16 H16B N4 0.919(16) 2.623(16) 3.5331(15) 170.9(14) . N18 H18A O9 0.907(16) 2.273(16) 2.9735(13) 133.8(14) 1_546 N18 H18B N3 0.874(17) 2.374(17) 3.1891(16) 155.3(13) 1_545 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.197 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.035 data_cnu921 _database_code_depnum_ccdc_archive 'CCDC 899441' #TrackingRef 'web_deposit_cif_file_4_Young-HyukJoo_1358438524.compound9 - 899441.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; carbohydrazidinium 1-methoxy-5-nitroiminotetrazolate ; _chemical_name_common 'carbohydrazidinium 1-methoxy-5-nitroiminotetrazolate' _chemical_melting_point ? _chemical_formula_moiety '2(C2 H3 N6 O3), C H8 N4 O' _chemical_formula_sum 'C5 H14 N16 O7' _chemical_formula_weight 410.32 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.37150(10) _cell_length_b 7.44260(10) _cell_length_c 15.3365(3) _cell_angle_alpha 101.616(3) _cell_angle_beta 97.4510(10) _cell_angle_gamma 94.214(5) _cell_volume 812.91(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5430 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 26.57 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_max 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.149 _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 296(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 SMART CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21966 _diffrn_reflns_av_R_equivalents 0.0533 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4040 _reflns_number_gt 2764 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0566P)^2^] 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 4040 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1032 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _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 0.13835(18) 0.44362(18) 0.77897(9) 0.0290(3) Uani 1 1 d . . . N2 N 0.08662(16) 0.51275(17) 0.85874(8) 0.0363(3) Uani 1 1 d . . . N3 N 0.22798(18) 0.6083(2) 0.91694(9) 0.0490(4) Uani 1 1 d . . . N4 N 0.36594(18) 0.6016(2) 0.87233(10) 0.0507(4) Uani 1 1 d . . . N5 N 0.31686(16) 0.49893(17) 0.78683(8) 0.0376(3) Uani 1 1 d . . . N6 N 0.00631(15) 0.33975(16) 0.71344(8) 0.0328(3) Uani 1 1 d . . . N7 N 0.06075(15) 0.27169(15) 0.63673(8) 0.0303(3) Uani 1 1 d . . . O8 O 0.22001(14) 0.29637(17) 0.62102(7) 0.0467(3) Uani 1 1 d . . . O9 O -0.06079(14) 0.17528(14) 0.57579(7) 0.0396(3) Uani 1 1 d . . . O10 O -0.08091(15) 0.47323(16) 0.88360(8) 0.0485(3) Uani 1 1 d . . . C11 C -0.1590(2) 0.6388(3) 0.92019(12) 0.0545(5) Uani 1 1 d . . . H11A H -0.2762 0.6068 0.9370 0.082 Uiso 1 1 calc R . . H11B H -0.1748 0.7127 0.8757 0.082 Uiso 1 1 calc R . . H11C H -0.0780 0.7073 0.9723 0.082 Uiso 1 1 calc R . . C12 C 0.69740(18) 1.02102(18) 0.25655(9) 0.0297(3) Uani 1 1 d . . . N13 N 0.64174(17) 0.92538(17) 0.17203(8) 0.0375(3) Uani 1 1 d . . . N14 N 0.7789(2) 0.9242(2) 0.12296(9) 0.0513(4) Uani 1 1 d . . . N15 N 0.9179(2) 1.0192(2) 0.17721(10) 0.0532(4) Uani 1 1 d . . . N16 N 0.87238(16) 1.08143(18) 0.26090(8) 0.0386(3) Uani 1 1 d . . . N17 N 0.57585(16) 1.02230(16) 0.31690(8) 0.0340(3) Uani 1 1 d . . . N18 N 0.61175(16) 1.15199(17) 0.39068(8) 0.0362(3) Uani 1 1 d . . . O19 O 0.74044(15) 1.27545(15) 0.40539(8) 0.0503(3) Uani 1 1 d . . . O20 O 0.50418(16) 1.1451(2) 0.44713(8) 0.0580(4) Uani 1 1 d . . . O21 O 0.47507(15) 0.82744(15) 0.13855(8) 0.0485(3) Uani 1 1 d . . . C22 C 0.3441(2) 0.9469(3) 0.10943(14) 0.0608(5) Uani 1 1 d . . . H22A H 0.2275 0.8762 0.0860 0.091 Uiso 1 1 calc R . . H22B H 0.3879 1.0011 0.0633 0.091 Uiso 1 1 calc R . . H22C H 0.3300 1.0426 0.1596 0.091 Uiso 1 1 calc R . . O23 O 0.26257(15) 0.32212(13) 0.29369(7) 0.0406(3) Uani 1 1 d . . . C24 C 0.27638(17) 0.42828(18) 0.36571(9) 0.0283(3) Uani 1 1 d . . . N25 N 0.18957(17) 0.39116(16) 0.43503(9) 0.0328(3) Uani 1 1 d . . . H25 H 0.235(2) 0.441(2) 0.4885(12) 0.049(5) Uiso 1 1 d . . . N26 N 0.12719(15) 0.20150(15) 0.42276(8) 0.0315(3) Uani 1 1 d . . . H26A H 0.0720 0.1839 0.4691 0.047 Uiso 1 1 calc R . . H26B H 0.2226 0.1351 0.4194 0.047 Uiso 1 1 calc R . . H26C H 0.0479 0.1666 0.3721 0.047 Uiso 1 1 calc R . . N27 N 0.37703(16) 0.59676(17) 0.38459(9) 0.0332(3) Uani 1 1 d . . . H27 H 0.358(3) 0.681(3) 0.4317(14) 0.067(6) Uiso 1 1 d . . . N28 N 0.40491(16) 0.66173(16) 0.30609(8) 0.0341(3) Uani 1 1 d . . . H28A H 0.4708 0.7714 0.3217 0.051 Uiso 1 1 calc R . . H28B H 0.2966 0.6722 0.2754 0.051 Uiso 1 1 calc R . . H28C H 0.4648 0.5824 0.2719 0.051 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 C1 0.0275(7) 0.0288(7) 0.0321(7) 0.0073(6) 0.0069(6) 0.0058(5) N2 0.0302(6) 0.0428(7) 0.0339(7) 0.0008(5) 0.0088(5) 0.0032(5) N3 0.0392(8) 0.0588(9) 0.0403(8) -0.0068(7) 0.0032(6) 0.0012(6) N4 0.0354(7) 0.0608(9) 0.0459(8) -0.0076(7) 0.0015(6) 0.0009(6) N5 0.0279(6) 0.0437(7) 0.0378(7) 0.0009(6) 0.0057(5) 0.0014(5) N6 0.0278(6) 0.0369(7) 0.0319(6) 0.0018(5) 0.0076(5) 0.0009(5) N7 0.0302(6) 0.0302(6) 0.0319(6) 0.0079(5) 0.0056(5) 0.0062(5) O8 0.0284(5) 0.0737(8) 0.0362(6) 0.0041(5) 0.0103(5) 0.0049(5) O9 0.0393(6) 0.0372(6) 0.0359(6) -0.0019(5) 0.0012(5) -0.0032(5) O10 0.0409(6) 0.0552(7) 0.0491(7) 0.0014(6) 0.0229(5) 0.0018(5) C11 0.0483(10) 0.0720(12) 0.0485(10) 0.0107(9) 0.0191(8) 0.0266(9) C12 0.0313(7) 0.0250(7) 0.0319(7) 0.0056(6) 0.0026(6) 0.0018(5) N13 0.0361(7) 0.0361(7) 0.0357(7) -0.0011(5) 0.0027(5) 0.0025(5) N14 0.0499(9) 0.0636(9) 0.0388(8) 0.0019(7) 0.0126(7) 0.0104(7) N15 0.0441(8) 0.0724(10) 0.0430(8) 0.0069(7) 0.0158(7) 0.0049(7) N16 0.0323(7) 0.0469(7) 0.0360(7) 0.0067(6) 0.0087(5) 0.0001(6) N17 0.0345(6) 0.0331(6) 0.0326(6) 0.0039(5) 0.0069(5) -0.0028(5) N18 0.0299(6) 0.0456(7) 0.0317(7) 0.0058(6) 0.0012(5) 0.0086(6) O19 0.0429(7) 0.0462(7) 0.0510(7) -0.0104(5) 0.0041(5) -0.0023(5) O20 0.0391(6) 0.1015(10) 0.0339(6) 0.0108(6) 0.0112(5) 0.0102(6) O21 0.0439(6) 0.0366(6) 0.0541(7) -0.0027(5) -0.0093(5) -0.0026(5) C22 0.0467(10) 0.0649(12) 0.0625(12) 0.0055(10) -0.0129(9) 0.0110(9) O23 0.0557(7) 0.0332(6) 0.0305(5) 0.0008(4) 0.0132(5) -0.0072(5) C24 0.0245(6) 0.0288(7) 0.0310(7) 0.0051(6) 0.0046(5) 0.0006(5) N25 0.0362(7) 0.0301(6) 0.0301(7) 0.0029(5) 0.0084(5) -0.0052(5) N26 0.0306(6) 0.0325(6) 0.0318(6) 0.0084(5) 0.0072(5) -0.0023(5) N27 0.0328(6) 0.0316(6) 0.0339(7) 0.0028(5) 0.0110(5) -0.0038(5) N28 0.0277(6) 0.0309(6) 0.0443(7) 0.0092(5) 0.0094(5) -0.0025(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N5 1.3322(17) . ? C1 N2 1.3428(17) . ? C1 N6 1.3703(18) . ? N2 N3 1.3351(17) . ? N2 O10 1.3678(15) . ? N3 N4 1.2958(19) . ? N4 N5 1.3664(18) . ? N6 N7 1.3093(16) . ? N7 O8 1.2368(14) . ? N7 O9 1.2686(14) . ? O10 C11 1.4401(19) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N16 1.3231(17) . ? C12 N13 1.3426(18) . ? C12 N17 1.3684(18) . ? N13 N14 1.3361(18) . ? N13 O21 1.3633(16) . ? N14 N15 1.2950(19) . ? N15 N16 1.3674(18) . ? N17 N18 1.3141(17) . ? N18 O19 1.2361(16) . ? N18 O20 1.2534(16) . ? O21 C22 1.448(2) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? O23 C24 1.2092(16) . ? C24 N27 1.3667(17) . ? C24 N25 1.3729(18) . ? N25 N26 1.4194(16) . ? N25 H25 0.842(18) . ? N26 H26A 0.8900 . ? N26 H26B 0.8900 . ? N26 H26C 0.8900 . ? N27 N28 1.4176(16) . ? N27 H27 0.89(2) . ? N28 H28A 0.8900 . ? N28 H28B 0.8900 . ? N28 H28C 0.8900 . ? 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 N5 C1 N2 106.14(12) . . ? N5 C1 N6 136.64(13) . . ? N2 C1 N6 117.22(12) . . ? N3 N2 C1 111.33(12) . . ? N3 N2 O10 122.41(12) . . ? C1 N2 O10 125.72(12) . . ? N4 N3 N2 104.94(12) . . ? N3 N4 N5 111.37(12) . . ? C1 N5 N4 106.18(11) . . ? N7 N6 C1 116.06(11) . . ? O8 N7 O9 119.41(11) . . ? O8 N7 N6 124.21(12) . . ? O9 N7 N6 116.38(11) . . ? N2 O10 C11 111.39(12) . . ? O10 C11 H11A 109.5 . . ? O10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N16 C12 N13 106.60(12) . . ? N16 C12 N17 135.52(13) . . ? N13 C12 N17 117.61(12) . . ? N14 N13 C12 110.87(12) . . ? N14 N13 O21 121.81(12) . . ? C12 N13 O21 127.12(12) . . ? N15 N14 N13 105.12(12) . . ? N14 N15 N16 111.17(13) . . ? C12 N16 N15 106.23(12) . . ? N18 N17 C12 116.43(12) . . ? O19 N18 O20 120.57(12) . . ? O19 N18 N17 123.98(12) . . ? O20 N18 N17 115.44(13) . . ? N13 O21 C22 110.37(12) . . ? O21 C22 H22A 109.5 . . ? O21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O23 C24 N27 122.94(13) . . ? O23 C24 N25 122.83(13) . . ? N27 C24 N25 114.22(12) . . ? C24 N25 N26 112.57(11) . . ? C24 N25 H25 119.5(12) . . ? N26 N25 H25 113.6(12) . . ? N25 N26 H26A 109.5 . . ? N25 N26 H26B 109.5 . . ? H26A N26 H26B 109.5 . . ? N25 N26 H26C 109.5 . . ? H26A N26 H26C 109.5 . . ? H26B N26 H26C 109.5 . . ? C24 N27 N28 112.73(11) . . ? C24 N27 H27 119.0(12) . . ? N28 N27 H27 116.3(12) . . ? N27 N28 H28A 109.5 . . ? N27 N28 H28B 109.5 . . ? H28A N28 H28B 109.5 . . ? N27 N28 H28C 109.5 . . ? H28A N28 H28C 109.5 . . ? H28B N28 H28C 109.5 . . ? 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 N25 H25 O19 0.842(18) 2.371(18) 3.0744(16) 141.4(15) 2_676 N25 H25 O8 0.842(18) 2.494(17) 3.0581(17) 125.2(14) . N26 H26A O9 0.89 2.02 2.9076(16) 173 . N26 H26A O8 0.89 2.40 2.9557(16) 121 . N26 H26B O20 0.89 2.06 2.8291(16) 145 1_545 N26 H26C N16 0.89 1.96 2.8530(16) 178 1_445 N27 H27 O20 0.89(2) 2.12(2) 2.8789(18) 142.4(17) 2_676 N27 H27 O9 0.89(2) 2.51(2) 3.0358(16) 118.5(15) 2_566 N27 H27 O19 0.89(2) 2.66(2) 3.4117(17) 143.4(15) 2_676 N28 H28A N17 0.89 1.99 2.8437(16) 161 . N28 H28B N6 0.89 2.26 3.0061(16) 142 2_566 N28 H28C N5 0.89 2.02 2.8460(16) 155 2_666 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.164 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.046 data_cnu951 _database_code_depnum_ccdc_archive 'CCDC 899442' #TrackingRef 'web_deposit_cif_file_5_Young-HyukJoo_1358438524.compound10 - 899442.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-amino-1,2,4-triazolium 1-methoxy-5-nitroiminotetrazolate ; _chemical_name_common '3-amino-1,2,4-triazolium 1-methoxy-5-nitroiminotetrazolate' _chemical_melting_point ? _chemical_formula_moiety 'C2 H3 N6 O3, C2 H5 N4' _chemical_formula_sum 'C4 H8 N10 O3' _chemical_formula_weight 244.20 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 P2(1)/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 3.8294(3) _cell_length_b 27.714(2) _cell_length_c 9.5787(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.7960(10) _cell_angle_gamma 90.00 _cell_volume 1007.18(14) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2573 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 22.10 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_max 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.610 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.137 _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 296(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 SMART CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15247 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 28.31 _reflns_number_total 2489 _reflns_number_gt 1461 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0404P)^2^] 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 2489 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0850 _refine_ls_wR_factor_gt 0.0765 _refine_ls_goodness_of_fit_ref 0.861 _refine_ls_restrained_S_all 0.861 _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 -0.0132(3) 0.12816(5) 0.34047(13) 0.0337(3) Uani 1 1 d . . . N2 N 0.1148(3) 0.17321(4) 0.33617(12) 0.0365(3) Uani 1 1 d . . . N3 N 0.0704(3) 0.19804(4) 0.45164(13) 0.0451(3) Uani 1 1 d . . . N4 N -0.0876(3) 0.16820(4) 0.52628(12) 0.0457(3) Uani 1 1 d . . . N5 N -0.1435(3) 0.12450(4) 0.46139(12) 0.0402(3) Uani 1 1 d . . . N6 N 0.0134(3) 0.09894(4) 0.22774(11) 0.0431(3) Uani 1 1 d . . . N7 N -0.1036(3) 0.05468(4) 0.23688(12) 0.0452(3) Uani 1 1 d . . . O8 O -0.2259(3) 0.03885(4) 0.34154(11) 0.0654(4) Uani 1 1 d . . . O9 O -0.0842(4) 0.02811(4) 0.13176(11) 0.0647(4) Uani 1 1 d . . . O10 O 0.2974(3) 0.19223(4) 0.23659(10) 0.0471(3) Uani 1 1 d . . . C11 C 0.0647(5) 0.22010(6) 0.13438(17) 0.0608(5) Uani 1 1 d . . . H11A H 0.1973 0.2332 0.0651 0.091 Uiso 1 1 calc R . . H11B H -0.0385 0.2459 0.1816 0.091 Uiso 1 1 calc R . . H11C H -0.1184 0.1996 0.0890 0.091 Uiso 1 1 calc R . . C12 C -0.4981(4) 0.08020(5) 0.73815(14) 0.0381(3) Uani 1 1 d . . . N13 N -0.4209(3) 0.12660(5) 0.75737(13) 0.0433(3) Uani 1 1 d . . . H13 H -0.317(4) 0.1443(6) 0.6983(17) 0.059(5) Uiso 1 1 d . . . N14 N -0.5067(3) 0.14351(5) 0.88423(13) 0.0520(4) Uani 1 1 d . . . C15 C -0.6349(4) 0.10607(6) 0.93789(17) 0.0517(4) Uani 1 1 d . . . H15 H -0.719(4) 0.1065(5) 1.0269(17) 0.063(5) Uiso 1 1 d . . . N16 N -0.6381(3) 0.06639(5) 0.85321(12) 0.0446(3) Uani 1 1 d . . . H16 H -0.725(4) 0.0337(6) 0.8654(17) 0.070(6) Uiso 1 1 d . . . N17 N -0.4478(4) 0.05283(5) 0.63133(15) 0.0532(4) Uani 1 1 d . . . H17A H -0.359(5) 0.0651(6) 0.5622(18) 0.068(6) Uiso 1 1 d . . . H17B H -0.534(5) 0.0234(7) 0.6328(18) 0.069(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 C1 0.0371(8) 0.0312(8) 0.0341(7) 0.0036(6) 0.0092(6) 0.0022(6) N2 0.0388(7) 0.0341(7) 0.0386(7) 0.0050(5) 0.0123(5) -0.0024(5) N3 0.0502(8) 0.0397(7) 0.0459(7) -0.0043(6) 0.0081(6) -0.0010(6) N4 0.0571(8) 0.0408(7) 0.0406(7) -0.0026(6) 0.0114(6) -0.0006(6) N5 0.0514(8) 0.0367(7) 0.0346(6) 0.0004(5) 0.0138(5) 0.0005(6) N6 0.0628(9) 0.0331(7) 0.0373(7) -0.0004(5) 0.0205(6) -0.0039(6) N7 0.0629(9) 0.0375(7) 0.0377(7) -0.0012(6) 0.0161(6) -0.0009(6) O8 0.1110(11) 0.0432(7) 0.0495(7) -0.0014(5) 0.0377(7) -0.0202(6) O9 0.1074(10) 0.0450(7) 0.0462(7) -0.0125(5) 0.0271(7) -0.0094(6) O10 0.0400(6) 0.0495(6) 0.0548(6) 0.0167(5) 0.0173(5) -0.0029(5) C11 0.0607(12) 0.0624(11) 0.0604(11) 0.0277(9) 0.0126(9) -0.0004(9) C12 0.0409(9) 0.0401(9) 0.0337(8) 0.0042(6) 0.0067(6) 0.0003(7) N13 0.0532(8) 0.0423(8) 0.0365(7) -0.0005(6) 0.0144(6) -0.0050(6) N14 0.0601(9) 0.0578(9) 0.0404(7) -0.0086(6) 0.0156(6) -0.0047(7) C15 0.0550(11) 0.0658(12) 0.0366(9) -0.0003(8) 0.0147(8) -0.0013(9) N16 0.0515(8) 0.0480(8) 0.0362(7) 0.0052(6) 0.0128(6) -0.0046(6) N17 0.0797(11) 0.0403(9) 0.0444(8) -0.0014(7) 0.0257(8) -0.0096(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N5 1.3257(16) . ? C1 N2 1.3442(16) . ? C1 N6 1.3645(16) . ? N2 N3 1.3329(15) . ? N2 O10 1.3630(13) . ? N3 N4 1.2957(16) . ? N4 N5 1.3648(15) . ? N6 N7 1.3128(15) . ? N7 O8 1.2427(14) . ? N7 O9 1.2577(14) . ? O10 C11 1.4535(18) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N17 1.3088(18) . ? C12 N13 1.3266(18) . ? C12 N16 1.3450(16) . ? N13 N14 1.3829(16) . ? N13 H13 0.883(16) . ? N14 C15 1.285(2) . ? C15 N16 1.3657(19) . ? C15 H15 0.952(16) . ? N16 H16 0.978(16) . ? N17 H17A 0.855(18) . ? N17 H17B 0.881(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 N5 C1 N2 106.25(11) . . ? N5 C1 N6 136.34(12) . . ? N2 C1 N6 117.41(11) . . ? N3 N2 C1 111.47(10) . . ? N3 N2 O10 121.09(11) . . ? C1 N2 O10 127.20(11) . . ? N4 N3 N2 104.49(11) . . ? N3 N4 N5 111.78(11) . . ? C1 N5 N4 106.01(11) . . ? N7 N6 C1 116.03(11) . . ? O8 N7 O9 120.58(12) . . ? O8 N7 N6 123.58(11) . . ? O9 N7 N6 115.84(11) . . ? N2 O10 C11 110.55(10) . . ? O10 C11 H11A 109.5 . . ? O10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N17 C12 N13 128.07(14) . . ? N17 C12 N16 126.37(14) . . ? N13 C12 N16 105.56(13) . . ? C12 N13 N14 112.06(12) . . ? C12 N13 H13 124.1(10) . . ? N14 N13 H13 123.8(10) . . ? C15 N14 N13 103.12(13) . . ? N14 C15 N16 112.70(14) . . ? N14 C15 H15 122.9(10) . . ? N16 C15 H15 124.4(10) . . ? C12 N16 C15 106.56(13) . . ? C12 N16 H16 122.8(9) . . ? C15 N16 H16 130.6(9) . . ? C12 N17 H17A 119.5(11) . . ? C12 N17 H17B 115.4(11) . . ? H17A N17 H17B 124.7(16) . . ? 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 N13 H13 N4 0.883(16) 2.079(16) 2.9368(17) 163.8(14) . N13 H13 N5 0.883(16) 2.511(16) 3.1603(16) 130.9(12) . N16 H16 O9 0.978(16) 1.863(17) 2.8374(17) 173.7(15) 3_456 N17 H17A N5 0.855(18) 2.131(18) 2.9100(19) 151.3(15) . N17 H17A O8 0.855(18) 2.355(17) 3.0361(17) 136.9(14) . N17 H17B O8 0.881(18) 1.986(19) 2.8587(19) 170.8(16) 3_456 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.165 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.041