# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_s234 _database_code_depnum_ccdc_archive 'CCDC 881227' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'barium 5,5-azoxybistetrazolate pentahydrate' _chemical_melting_point ? _chemical_formula_moiety 'C2 H10 Ba N10 O6' _chemical_formula_sum 'C2 H10 Ba N10 O6' _chemical_formula_weight 407.54 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' Ba Ba -0.3244 2.2819 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/m' _symmetry_Int_Tables_number 11 _symmetry_space_group_name_Hall '-P 2yb ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 5.7898(3) _cell_length_b 14.9314(7) _cell_length_c 7.0531(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.949(3) _cell_angle_gamma 90.00 _cell_volume 596.53(5) _cell_formula_units_Z 2 _cell_measurement_temperature 233(2) _cell_measurement_reflns_used 6019 _cell_measurement_theta_min 1 _cell_measurement_theta_max 26.5 _exptl_crystal_description prism _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 3.376 _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 233(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 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3780 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 25.98 _reflns_number_total 1212 _reflns_number_gt 1177 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement ? _computing_data_reduction 'DENZO and SCALEPACK' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Half a molecule into the asymmetric unit. Occupation disorder of O1 with occupation factor of 0.5. Hydrogen atoms of water molecules were found and refined with bond restraints (d=0.85 angs.) and isotropic displacement factors. ; _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^)+(0.0032P)^2^+0.5935P] 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 refU _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1212 _refine_ls_number_parameters 117 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0177 _refine_ls_R_factor_gt 0.0169 _refine_ls_wR_factor_ref 0.0395 _refine_ls_wR_factor_gt 0.0392 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.115 _refine_ls_shift/su_max 0.002 _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 Ba1 Ba 0.18813(3) 0.2500 0.18753(3) 0.02548(8) Uani 1 2 d S . . C1 C 0.2884(4) 0.51313(16) 0.1473(4) 0.0272(5) Uani 1 1 d . . . N1 N 0.3850(3) 0.43322(14) 0.1949(3) 0.0304(5) Uani 1 1 d . . . N2 N 0.5988(4) 0.45359(16) 0.3002(3) 0.0363(5) Uani 1 1 d . . . N3 N 0.6255(4) 0.54067(17) 0.3107(4) 0.0427(6) Uani 1 1 d . . . N4 N 0.4294(4) 0.58111(15) 0.2151(4) 0.0400(6) Uani 1 1 d . . . N5 N 0.0634(3) 0.53317(13) 0.0325(3) 0.0285(4) Uani 1 1 d . . . O1 O 0.0321(7) 0.6114(3) 0.0219(7) 0.0548(12) Uani 0.50 1 d P . . O2 O 0.0173(3) 0.35765(14) 0.4485(3) 0.0439(5) Uani 1 1 d D . . H2A H 0.114(5) 0.395(2) 0.506(5) 0.064(11) Uiso 1 1 d D . . H2B H -0.112(4) 0.384(2) 0.413(6) 0.081(14) Uiso 1 1 d D . . O3 O -0.3576(5) 0.2500 0.0505(4) 0.0353(6) Uani 1 2 d SD . . H3 H -0.369(6) 0.2934(17) -0.026(4) 0.056(10) Uiso 1 1 d D . . O4 O 0.5270(5) 0.2500 0.5219(5) 0.0457(7) Uani 1 2 d SD . . H4 H 0.577(7) 0.295(2) 0.589(6) 0.096(16) Uiso 1 1 d D . . O5 O 0.0812(9) 0.2500 -0.2052(6) 0.0845(13) Uani 1 2 d SD . . H5 H 0.073(11) 0.294(3) -0.277(7) 0.14(2) Uiso 1 1 d 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 Ba1 0.02761(12) 0.02307(12) 0.02538(13) 0.000 0.00462(9) 0.000 C1 0.0276(11) 0.0278(12) 0.0285(13) -0.0026(10) 0.0109(10) -0.0044(10) N1 0.0239(9) 0.0328(12) 0.0323(12) -0.0018(9) 0.0013(9) -0.0040(9) N2 0.0256(10) 0.0494(14) 0.0329(12) -0.0043(10) 0.0035(9) -0.0047(10) N3 0.0327(12) 0.0530(15) 0.0426(14) -0.0193(12) 0.0083(10) -0.0160(11) N4 0.0368(12) 0.0336(12) 0.0511(15) -0.0136(11) 0.0124(11) -0.0121(10) N5 0.0319(10) 0.0211(10) 0.0343(12) -0.0028(9) 0.0110(9) -0.0037(8) O1 0.052(2) 0.031(2) 0.071(3) 0.005(2) -0.013(2) 0.0039(18) O2 0.0305(10) 0.0419(12) 0.0575(14) -0.0187(10) 0.0052(10) -0.0015(9) O3 0.0393(14) 0.0307(14) 0.0366(16) 0.000 0.0096(12) 0.000 O4 0.0441(16) 0.0432(18) 0.0418(18) 0.000 -0.0092(13) 0.000 O5 0.102(3) 0.121(4) 0.031(2) 0.000 0.015(2) 0.000 _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 Ba1 O5 2.710(4) . ? Ba1 O4 2.737(3) . ? Ba1 O2 2.776(2) . ? Ba1 O2 2.776(2) 4_565 ? Ba1 N1 2.960(2) . ? Ba1 O3 3.107(3) . ? C1 N4 1.328(3) . ? C1 N1 1.331(3) . ? C1 N5 1.416(3) . ? N1 N2 1.340(3) . ? N2 N3 1.310(3) . ? N3 N4 1.339(3) . ? N5 O1 1.183(4) . ? N5 N5 1.262(4) 3_565 ? O1 Ba1 2.703(4) 3_565 ? O2 H2B 0.834(19) . ? O2 H2A 0.834(18) . ? O3 H3 0.837(18) . ? O3 Ba1 2.984(3) 1_455 ? O4 H4 0.833(19) . ? O5 H5 0.83(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 O1 Ba1 O1 99.87(18) 2_545 3_565 ? O1 Ba1 O5 57.28(12) 2_545 . ? O1 Ba1 O5 57.28(12) 3_565 . ? O1 Ba1 O4 130.05(9) 2_545 . ? O1 Ba1 O4 130.05(9) 3_565 . ? O5 Ba1 O4 148.40(13) . . ? O1 Ba1 O2 127.81(11) 2_545 . ? O1 Ba1 O2 74.14(12) 3_565 . ? O5 Ba1 O2 129.82(9) . . ? O4 Ba1 O2 73.67(7) . . ? O1 Ba1 O2 74.14(12) 2_545 4_565 ? O1 Ba1 O2 127.81(11) 3_565 4_565 ? O5 Ba1 O2 129.82(9) . 4_565 ? O4 Ba1 O2 73.67(7) . 4_565 ? O2 Ba1 O2 70.77(9) . 4_565 ? O1 Ba1 N1 148.57(11) 2_545 . ? O1 Ba1 N1 55.85(10) 3_565 . ? O5 Ba1 N1 91.35(6) . . ? O4 Ba1 N1 77.30(5) . . ? O2 Ba1 N1 69.01(6) . . ? O2 Ba1 N1 135.42(6) 4_565 . ? O1 Ba1 N1 55.85(10) 2_545 4_565 ? O1 Ba1 N1 148.57(11) 3_565 4_565 ? O5 Ba1 N1 91.35(6) . 4_565 ? O4 Ba1 N1 77.30(5) . 4_565 ? O2 Ba1 N1 135.42(6) . 4_565 ? O2 Ba1 N1 69.01(6) 4_565 4_565 ? N1 Ba1 N1 135.11(8) . 4_565 ? O1 Ba1 O3 99.83(11) 2_545 1_655 ? O1 Ba1 O3 99.83(11) 3_565 1_655 ? O5 Ba1 O3 72.49(12) . 1_655 ? O4 Ba1 O3 75.91(9) . 1_655 ? O2 Ba1 O3 132.36(5) . 1_655 ? O2 Ba1 O3 132.36(5) 4_565 1_655 ? N1 Ba1 O3 69.13(4) . 1_655 ? N1 Ba1 O3 69.13(4) 4_565 1_655 ? O1 Ba1 O3 59.71(10) 2_545 . ? O1 Ba1 O3 59.71(10) 3_565 . ? O5 Ba1 O3 71.31(12) . . ? O4 Ba1 O3 140.29(9) . . ? O2 Ba1 O3 74.18(6) . . ? O2 Ba1 O3 74.18(6) 4_565 . ? N1 Ba1 O3 111.62(4) . . ? N1 Ba1 O3 111.62(4) 4_565 . ? O3 Ba1 O3 143.80(10) 1_655 . ? N4 C1 N1 113.6(2) . . ? N4 C1 N5 117.9(2) . . ? N1 C1 N5 128.5(2) . . ? C1 N1 N2 103.2(2) . . ? C1 N1 Ba1 133.17(15) . . ? N2 N1 Ba1 121.85(16) . . ? N3 N2 N1 110.0(2) . . ? N2 N3 N4 110.0(2) . . ? C1 N4 N3 103.3(2) . . ? O1 N5 N5 133.1(3) . 3_565 ? O1 N5 C1 110.8(3) . . ? N5 N5 C1 116.1(3) 3_565 . ? N5 O1 Ba1 147.1(3) . 3_565 ? H2B O2 H2A 107(4) . . ? H2B O2 Ba1 120(3) . . ? H2A O2 Ba1 115(2) . . ? H3 O3 Ba1 105(2) . 1_455 ? H3 O3 Ba1 98(2) . . ? Ba1 O3 Ba1 143.80(10) 1_455 . ? H4 O4 Ba1 126(3) . . ? H5 O5 Ba1 127(4) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.315 _refine_diff_density_min -0.605 _refine_diff_density_rms 0.070 data_s245 _database_code_depnum_ccdc_archive 'CCDC 881228' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'disodium 5,5-azoxybistetrazolate pentahydrate' _chemical_melting_point ? _chemical_formula_moiety 'C2 H10 N10 Na2 O6 ' _chemical_formula_sum 'C2 H10 N10 Na2 O6' _chemical_formula_weight 316.18 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' Na Na 0.0362 0.0249 '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_Int_Tables_number 2 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2189(6) _cell_length_b 7.6977(5) _cell_length_c 11.9774(9) _cell_angle_alpha 82.844(5) _cell_angle_beta 81.990(4) _cell_angle_gamma 68.294(4) _cell_volume 610.41(8) _cell_formula_units_Z 2 _cell_measurement_temperature 233(2) _cell_measurement_reflns_used 8833 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.214 _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 233(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 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3373 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2100 _reflns_number_gt 1916 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement ? _computing_data_reduction 'DENZO and SCALEPACK' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Position disorder of one oxygen atom over two nitrogen atoms, O1 at N5 and O1A at N6 with ratio 3:1. Hydrogen atoms at water molecules were found and refined with isotropic displacement parameters and bond restraints (d=0.84 angs.) ; _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^)+(0.0381P)^2^+0.6587P] 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 0.038(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2100 _refine_ls_number_parameters 231 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1149 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.079 _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 O1 O 0.3898(4) 0.2530(3) 0.5304(2) 0.0520(7) Uani 0.75 1 d P . . O1A O 0.0848(15) 0.7217(11) 0.5118(7) 0.060(2) Uani 0.25 1 d P . . Na1 Na 0.36347(14) 0.88657(14) 0.08521(8) 0.0346(3) Uani 1 1 d . . . Na2 Na -0.12886(15) 1.00856(14) 0.64220(8) 0.0388(3) Uani 1 1 d . . . C1 C 0.3663(4) 0.4716(4) 0.3779(2) 0.0318(6) Uani 1 1 d . . . C2 C 0.1102(3) 0.5100(3) 0.6568(2) 0.0311(6) Uani 1 1 d . . . O2 O 0.2329(3) 0.7407(3) -0.03349(17) 0.0440(5) Uani 1 1 d D . . H2A H 0.315(4) 0.683(4) -0.081(2) 0.056(10) Uiso 1 1 d D . . H2B H 0.186(6) 0.670(5) 0.011(3) 0.091(15) Uiso 1 1 d D . . O3 O 0.4548(3) 0.9856(3) 0.25130(17) 0.0399(5) Uani 1 1 d D . . H3A H 0.479(6) 1.076(4) 0.268(3) 0.075(12) Uiso 1 1 d D . . H3B H 0.554(4) 0.899(4) 0.276(3) 0.073(12) Uiso 1 1 d D . . O4 O 0.3017(3) 1.2007(3) 0.00530(16) 0.0386(5) Uani 1 1 d D . . H4A H 0.229(5) 1.253(5) -0.047(2) 0.066(11) Uiso 1 1 d D . . H4B H 0.242(5) 1.263(5) 0.059(2) 0.070(12) Uiso 1 1 d D . . O5 O -0.0260(3) 1.0210(3) 0.82373(16) 0.0382(5) Uani 1 1 d D . . H5A H 0.054(4) 0.939(4) 0.864(3) 0.058(10) Uiso 1 1 d D . . H5B H 0.015(6) 1.109(4) 0.823(3) 0.075(13) Uiso 1 1 d D . . O6 O 0.1967(3) 0.9933(4) 0.55022(19) 0.0530(6) Uani 1 1 d D . . H6A H 0.240(5) 1.080(4) 0.538(3) 0.048(10) Uiso 1 1 d D . . H6B H 0.297(5) 0.908(5) 0.576(4) 0.093(15) Uiso 1 1 d D . . N1 N 0.4984(3) 0.3389(3) 0.3162(2) 0.0408(6) Uani 1 1 d . . . N2 N 0.5225(3) 0.4326(3) 0.2173(2) 0.0408(6) Uani 1 1 d . . . N3 N 0.4103(3) 0.6110(3) 0.22140(17) 0.0357(5) Uani 1 1 d . . . N4 N 0.3076(3) 0.6423(3) 0.32353(17) 0.0329(5) Uani 1 1 d . . . N5 N 0.3049(3) 0.4214(3) 0.49084(18) 0.0346(5) Uani 1 1 d . . . N6 N 0.1747(3) 0.5546(3) 0.54005(18) 0.0346(5) Uani 1 1 d . . . N7 N 0.1661(3) 0.3522(3) 0.72100(19) 0.0398(6) Uani 1 1 d . . . N8 N 0.0576(4) 0.3973(4) 0.8197(2) 0.0485(6) Uani 1 1 d . . . N9 N -0.0598(3) 0.5799(4) 0.81203(19) 0.0451(6) Uani 1 1 d . . . N10 N -0.0265(3) 0.6523(3) 0.70894(18) 0.0361(5) 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 O1 0.0523(16) 0.0263(14) 0.0652(18) 0.0033(12) -0.0121(14) -0.0001(12) O1A 0.081(6) 0.031(4) 0.041(5) 0.010(3) 0.002(4) 0.002(4) Na1 0.0349(5) 0.0358(6) 0.0299(5) -0.0012(4) 0.0005(4) -0.0107(4) Na2 0.0426(6) 0.0351(6) 0.0327(6) -0.0063(4) 0.0014(4) -0.0076(5) C1 0.0347(13) 0.0346(14) 0.0326(13) 0.0036(10) -0.0102(10) -0.0197(11) C2 0.0280(12) 0.0286(13) 0.0367(13) -0.0080(11) -0.0045(10) -0.0080(10) O2 0.0470(12) 0.0455(12) 0.0369(11) -0.0107(10) -0.0001(9) -0.0129(10) O3 0.0443(11) 0.0308(11) 0.0453(11) -0.0041(9) -0.0120(9) -0.0111(9) O4 0.0362(10) 0.0420(11) 0.0279(10) -0.0014(8) 0.0012(8) -0.0049(9) O5 0.0372(10) 0.0356(11) 0.0396(11) -0.0031(9) -0.0043(8) -0.0106(9) O6 0.0417(12) 0.0611(16) 0.0511(13) -0.0108(11) -0.0084(10) -0.0093(12) N1 0.0356(12) 0.0275(12) 0.0546(15) -0.0068(10) -0.0021(10) -0.0057(10) N2 0.0396(12) 0.0352(13) 0.0463(14) -0.0111(10) 0.0027(10) -0.0119(10) N3 0.0390(12) 0.0347(12) 0.0309(11) -0.0048(9) -0.0003(9) -0.0106(10) N4 0.0382(11) 0.0302(12) 0.0274(11) -0.0028(9) -0.0001(9) -0.0100(9) N5 0.0349(11) 0.0286(12) 0.0380(12) -0.0034(9) -0.0069(9) -0.0074(9) N6 0.0336(11) 0.0238(11) 0.0427(12) -0.0061(9) -0.0069(9) -0.0040(9) N7 0.0407(12) 0.0357(13) 0.0407(13) -0.0033(10) -0.0067(10) -0.0098(10) N8 0.0554(15) 0.0583(17) 0.0399(13) 0.0118(11) -0.0141(11) -0.0314(13) N9 0.0392(13) 0.0607(17) 0.0368(13) -0.0120(11) 0.0026(10) -0.0193(12) N10 0.0350(11) 0.0340(12) 0.0364(12) -0.0086(9) -0.0007(9) -0.0082(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 N5 1.273(3) . ? O1A N6 1.235(8) . ? O1A Na2 2.681(8) 2_576 ? O1A Na2 2.713(8) . ? Na1 O4 2.389(2) . ? Na1 O2 2.393(2) . ? Na1 N3 2.457(2) . ? Na1 O3 2.468(2) . ? Na2 O5 2.417(2) . ? Na2 O6 2.420(3) . ? Na2 N10 2.613(2) . ? C1 N1 1.331(3) . ? C1 N4 1.335(3) . ? C1 N5 1.416(3) . ? C2 N7 1.312(3) . ? C2 N10 1.328(3) . ? C2 N6 1.451(3) . ? O2 H2A 0.809(18) . ? O2 H2B 0.840(19) . ? O3 H3A 0.834(19) . ? O3 H3B 0.839(19) . ? O3 Na2 2.503(2) 2_576 ? O4 H4B 0.821(19) . ? O4 H4A 0.842(19) . ? O4 Na1 2.391(2) 2_675 ? O5 H5B 0.831(19) . ? O5 H5A 0.838(18) . ? O5 Na1 2.409(2) 2_576 ? O6 H6A 0.827(18) . ? O6 H6B 0.845(19) . ? O6 Na2 2.425(2) 2_576 ? N1 N2 1.332(3) . ? N2 N3 1.315(3) . ? N3 N4 1.339(3) . ? N4 Na2 2.572(2) 2_576 ? N5 N6 1.251(3) . ? N7 N8 1.332(3) . ? N8 N9 1.346(4) . ? N9 N10 1.318(3) . ? 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 N6 O1A Na2 139.3(6) . 2_576 ? N6 O1A Na2 129.7(5) . . ? Na2 O1A Na2 84.9(2) 2_576 . ? O4 Na1 O4 88.93(7) . 2_675 ? O4 Na1 O2 107.01(8) . . ? O4 Na1 O2 98.22(8) 2_675 . ? O4 Na1 O5 90.32(7) . 2_576 ? O4 Na1 O5 179.18(8) 2_675 2_576 ? O2 Na1 O5 82.31(7) . 2_576 ? O4 Na1 N3 162.30(8) . . ? O4 Na1 N3 98.40(8) 2_675 . ? O2 Na1 N3 87.96(8) . . ? O5 Na1 N3 82.23(7) 2_576 . ? O4 Na1 O3 86.04(7) . . ? O4 Na1 O3 92.48(7) 2_675 . ? O2 Na1 O3 163.17(8) . . ? O5 Na1 O3 87.14(7) 2_576 . ? N3 Na1 O3 77.60(7) . . ? O4 Na1 Na1 44.50(5) . 2_675 ? O4 Na1 Na1 44.43(5) 2_675 2_675 ? O2 Na1 Na1 107.77(7) . 2_675 ? O5 Na1 Na1 134.81(7) 2_576 2_675 ? N3 Na1 Na1 140.31(7) . 2_675 ? O3 Na1 Na1 88.97(6) . 2_675 ? O4 Na1 Na2 97.93(6) . 2_576 ? O4 Na1 Na2 136.30(6) 2_675 2_576 ? O2 Na1 Na2 120.24(6) . 2_576 ? O5 Na1 Na2 43.52(5) 2_576 2_576 ? N3 Na1 Na2 65.71(5) . 2_576 ? O3 Na1 Na2 45.58(5) . 2_576 ? Na1 Na1 Na2 127.11(5) 2_675 2_576 ? O5 Na2 O6 90.56(8) . . ? O5 Na2 O6 172.86(9) . 2_576 ? O6 Na2 O6 82.61(8) . 2_576 ? O5 Na2 O3 86.16(7) . 2_576 ? O6 Na2 O3 176.28(8) . 2_576 ? O6 Na2 O3 100.73(8) 2_576 2_576 ? O5 Na2 N4 78.24(7) . 2_576 ? O6 Na2 N4 103.48(9) . 2_576 ? O6 Na2 N4 101.26(8) 2_576 2_576 ? O3 Na2 N4 77.58(7) 2_576 2_576 ? O5 Na2 N10 82.07(7) . . ? O6 Na2 N10 96.58(8) . . ? O6 Na2 N10 100.72(9) 2_576 . ? O3 Na2 N10 81.25(7) 2_576 . ? N4 Na2 N10 151.86(8) 2_576 . ? O5 Na2 O1A 113.2(2) . 2_576 ? O6 Na2 O1A 58.2(2) . 2_576 ? O6 Na2 O1A 61.3(2) 2_576 2_576 ? O3 Na2 O1A 124.8(2) 2_576 2_576 ? N4 Na2 O1A 58.77(18) 2_576 2_576 ? N10 Na2 O1A 149.05(19) . 2_576 ? O5 Na2 O1A 120.4(2) . . ? O6 Na2 O1A 60.9(2) . . ? O6 Na2 O1A 57.72(19) 2_576 . ? O3 Na2 O1A 119.5(2) 2_576 . ? N4 Na2 O1A 153.48(18) 2_576 . ? N10 Na2 O1A 54.61(17) . . ? O1A Na2 O1A 95.1(2) 2_576 . ? O5 Na2 Na1 43.33(5) . 2_576 ? O6 Na2 Na1 132.46(7) . 2_576 ? O6 Na2 Na1 142.70(7) 2_576 2_576 ? O3 Na2 Na1 44.76(5) 2_576 2_576 ? N4 Na2 Na1 63.12(5) 2_576 2_576 ? N10 Na2 Na1 88.78(6) . 2_576 ? O1A Na2 Na1 121.09(18) 2_576 2_576 ? O1A Na2 Na1 143.39(17) . 2_576 ? O5 Na2 Na2 131.88(7) . 2_576 ? O6 Na2 Na2 41.35(6) . 2_576 ? O6 Na2 Na2 41.26(6) 2_576 2_576 ? O3 Na2 Na2 141.96(7) 2_576 2_576 ? N4 Na2 Na2 106.57(6) 2_576 2_576 ? N10 Na2 Na2 101.54(6) . 2_576 ? O1A Na2 Na2 47.95(18) 2_576 2_576 ? O1A Na2 Na2 47.20(17) . 2_576 ? Na1 Na2 Na2 168.20(5) 2_576 2_576 ? N1 C1 N4 114.0(2) . . ? N1 C1 N5 118.8(2) . . ? N4 C1 N5 127.2(2) . . ? N7 C2 N10 113.7(2) . . ? N7 C2 N6 130.9(2) . . ? N10 C2 N6 115.3(2) . . ? H2A O2 H2B 111(4) . . ? H2A O2 Na1 114(2) . . ? H2B O2 Na1 105(3) . . ? H3A O3 H3B 99(4) . . ? H3A O3 Na1 138(3) . . ? H3B O3 Na1 109(3) . . ? H3A O3 Na2 108(3) . 2_576 ? H3B O3 Na2 113(3) . 2_576 ? Na1 O3 Na2 89.66(7) . 2_576 ? H4B O4 H4A 103(3) . . ? H4B O4 Na1 103(3) . . ? H4A O4 Na1 125(3) . . ? H4B O4 Na1 134(3) . 2_675 ? H4A O4 Na1 104(2) . 2_675 ? Na1 O4 Na1 91.07(7) . 2_675 ? H5B O5 H5A 100(4) . . ? H5B O5 Na1 109(3) . 2_576 ? H5A O5 Na1 111(2) . 2_576 ? H5B O5 Na2 111(3) . . ? H5A O5 Na2 131(2) . . ? Na1 O5 Na2 93.15(7) 2_576 . ? H6A O6 H6B 100(4) . . ? H6A O6 Na2 127(2) . . ? H6B O6 Na2 117(3) . . ? H6A O6 Na2 97(2) . 2_576 ? H6B O6 Na2 119(3) . 2_576 ? Na2 O6 Na2 97.39(8) . 2_576 ? C1 N1 N2 103.1(2) . . ? N3 N2 N1 110.1(2) . . ? N2 N3 N4 110.3(2) . . ? N2 N3 Na1 133.34(16) . . ? N4 N3 Na1 116.36(15) . . ? C1 N4 N3 102.5(2) . . ? C1 N4 Na2 141.95(16) . 2_576 ? N3 N4 Na2 114.24(15) . 2_576 ? N6 N5 O1 128.4(2) . . ? N6 N5 C1 113.8(2) . . ? O1 N5 C1 117.8(2) . . ? O1A N6 N5 134.3(4) . . ? O1A N6 C2 110.2(4) . . ? N5 N6 C2 115.6(2) . . ? C2 N7 N8 103.7(2) . . ? N7 N8 N9 109.6(2) . . ? N10 N9 N8 108.5(2) . . ? N9 N10 C2 104.5(2) . . ? N9 N10 Na2 126.57(16) . . ? C2 N10 Na2 126.91(17) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.888 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.050 data_s294 _database_code_depnum_ccdc_archive 'CCDC 881229' #TrackingRef 'S294_NH4_AzOxy.CIF' _vrf_PLAT780_s294 ; RESPONSE: The molecules is connected correctly. Alert could be caused by the strongly disordered azoxy moiety' ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'diammonium 5,5-azoxybistetrazolate' _chemical_melting_point ? _chemical_formula_moiety 'C2 N10 O, 2(H4 N) ' _chemical_formula_sum 'C2 H8 N12 O' _chemical_formula_weight 216.20 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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.708(1) _cell_length_b 7.429(1) _cell_length_c 7.483(1) _cell_angle_alpha 102.21(1) _cell_angle_beta 107.68(1) _cell_angle_gamma 106.78(1) _cell_volume 225.54(6) _cell_formula_units_Z 1 _cell_measurement_temperature 233(2) _cell_measurement_reflns_used 4418 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 112 _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 233(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 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1285 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0486 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 24.91 _reflns_number_total 755 _reflns_number_gt 687 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement ? _computing_data_reduction 'DENZO and SCALEPACK' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Half a molecule in the asymmetric unit, which will be completed by a symmetry center. The oxygen atom of the monoxide, which prevent the the inversion symmetry of the molecule by the bridging N2-group, is occupational disordered with an occupation factor of 0.5. Furthermore the bridging N2-group is positional disordered around 3:1 by N1 and N11. An effect of this disorder influence the displacment parameters of the oxygen atom and the ring atoms C1, N2, N3, N4 and N5, which have higher anisotropic displacement parameters, because the 5-membered rings at the bridging N2-groups doesn't overlay exactly. Several crystals were tested on the diffractometer and all show at the CCD-images reflections with broad or splitted positions. Also in the refinement nearly the 50 most disagreeable have greater values for F(obs) in comparison to F(calc). These observations can be caused by a twinned crystal. Therefore the structure was solved as twinned crystal with twin matrix 1 0 0 0 0 1 0 1 0 and a BASF factor of 0.26. This will lower the R1-value from 0.071 to 0.048. All four hydrogen atoms could be found for N6 in P-1 and were refined isotropically with bond restraints (d=0.89 angs.). Nevertheless it should by mentioned, that a cell transformation to a C-centered monoclinic lattice is possible and similar solutions of these structure can by obtained in the space group C2/m and C2. The comparable R1-values to 0.071 for P-1 (691 reflections) are 0.088 for C2/m (379 reflections) and 0.063 for C2 (668 reflections). The solution in C2 seems better, but most of the atoms shows distorted anisotropic displacement parameters and hydrogen atoms of NH4-cations couldn't be exactly determined in contrast to the centrosymmetric groups P-1 and C2/m. ; _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^)+(0.0614P)^2^+0.0760P] 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 0.52(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 755 _refine_ls_number_parameters 100 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1240 _refine_ls_wR_factor_gt 0.1186 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 0.3765(5) 0.1442(4) 0.6621(4) 0.0425(7) Uani 1 1 d . . . O1 O 0.5033(13) -0.1433(9) 0.6626(8) 0.0562(10) Uani 0.50 1 d P . . N1 N 0.4794(8) -0.0062(11) 0.5791(7) 0.0365(9) Uani 0.75 1 d P . . N11 N 0.522(3) -0.0794(19) 0.503(3) 0.034(2) Uani 0.25 1 d P . . N2 N 0.3178(7) 0.1205(4) 0.8168(4) 0.0485(7) Uani 1 1 d . . . N3 N 0.2185(6) 0.2653(4) 0.8697(4) 0.0478(8) Uani 1 1 d . . . N4 N 0.2201(6) 0.3710(4) 0.7492(4) 0.0475(7) Uani 1 1 d . . . N5 N 0.3212(6) 0.2961(4) 0.6142(4) 0.0478(8) Uani 1 1 d . . . N6 N 0.0050(7) 0.2980(4) 0.2018(4) 0.0392(6) Uani 1 1 d D . . H1 H 0.085(9) 0.299(6) 0.105(5) 0.067(11) Uiso 1 1 d D . . H2 H -0.071(9) 0.396(5) 0.228(5) 0.061(10) Uiso 1 1 d D . . H3 H 0.160(7) 0.331(5) 0.321(3) 0.051(9) Uiso 1 1 d D . . H4 H -0.145(8) 0.176(4) 0.172(6) 0.078(12) Uiso 1 1 d 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 0.0317(12) 0.0368(16) 0.0403(17) -0.0016(10) 0.0044(11) 0.0078(11) O1 0.068(2) 0.071(3) 0.069(3) 0.054(2) 0.041(2) 0.043(2) N1 0.0399(19) 0.039(3) 0.031(2) 0.014(3) 0.0125(14) 0.0144(15) N11 0.029(5) 0.032(7) 0.019(7) 0.006(7) -0.001(5) -0.005(5) N2 0.0530(16) 0.0403(15) 0.0467(15) 0.0174(12) 0.0153(12) 0.0121(12) N3 0.0462(14) 0.0484(16) 0.0381(14) 0.0045(12) 0.0164(11) 0.0100(12) N4 0.0498(15) 0.0360(14) 0.0469(15) 0.0077(11) 0.0110(12) 0.0155(12) N5 0.0526(16) 0.0500(16) 0.0355(14) 0.0145(11) 0.0159(12) 0.0129(12) N6 0.0485(12) 0.0335(15) 0.0345(14) 0.0117(8) 0.0150(10) 0.0150(11) _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 1.303(5) . ? C1 N5 1.325(4) . ? C1 N1 1.439(8) . ? O1 N1 1.316(8) . ? O1 N11 1.39(2) . ? N1 N11 0.811(15) . ? N1 N1 1.274(10) 2_656 ? N2 N3 1.325(4) . ? N3 N4 1.315(3) . ? N4 N5 1.328(4) . ? N6 H3 0.894(18) . ? N6 H4 0.908(19) . ? N6 H2 0.911(19) . ? N6 H1 0.916(19) . ? 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 113.6(2) . . ? N2 C1 N1 111.7(4) . . ? N5 C1 N1 134.7(4) . . ? N2 C1 N11 150.5(7) . 2_656 ? N5 C1 N11 95.9(7) . 2_656 ? N11 N1 N11 89.5(18) . 2_656 ? N11 N1 N1 50.0(13) . 2_656 ? N11 N1 O1 77.5(18) . . ? N11 N1 O1 167.0(19) 2_656 . ? N1 N1 O1 127.5(10) 2_656 . ? N11 N1 C1 162.4(18) . . ? N11 N1 C1 73.7(17) 2_656 . ? N1 N1 C1 113.1(9) 2_656 . ? O1 N1 C1 119.3(5) . . ? N1 N11 N1 90.5(18) . 2_656 ? N1 N11 N11 50.6(14) . 2_656 ? N1 N11 O1 67.7(19) . . ? N1 N11 O1 158(2) 2_656 . ? N11 N11 O1 118(3) 2_656 . ? N1 N11 C1 157(2) . 2_656 ? N1 N11 C1 67.5(17) 2_656 2_656 ? N11 N11 C1 107(2) 2_656 2_656 ? O1 N11 C1 134.1(12) . 2_656 ? C1 N2 N3 103.7(3) . . ? N4 N3 N2 110.1(3) . . ? N3 N4 N5 108.9(3) . . ? C1 N5 N4 103.7(2) . . ? H3 N6 H4 109(3) . . ? H3 N6 H2 99(3) . . ? H4 N6 H2 112(4) . . ? H3 N6 H1 112(4) . . ? H4 N6 H1 110(3) . . ? H2 N6 H1 114(3) . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 24.91 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.207 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.047 data_gx003 _database_code_depnum_ccdc_archive 'CCDC 881230' _audit_author_name 'Joerg Stierstorfer' _audit_block_code ? _audit_creation_method SHELXL-97 _audit_creation_date ; 'Wed Jan 05 10:56:51 2011' ; _audit_update_record 13.01.2011 _chemical_name_systematic 'dihydroxylammonium 5,5-azoxy-tetrazolate dihydrate' _chemical_compound_source ? _chemical_name_common 'dihydroxylammonium 5,5-azoxy-tetrazolate dihydrate' _chemical_formula_moiety 'C2 N10 O, 2(H4 N O), 2(H2 O)' _chemical_formula_sum 'C2 H12 N12 O5' _chemical_formula_weight 284.24 _diffrn_ambient_temperature 173 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power ? # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method omega-scan _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 5933 _diffrn_reflns_av_R_equivalents 0.0572 _diffrn_reflns_av_sigmaI/netI 0.0859 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.48 _diffrn_reflns_theta_max 25.74 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.74 _diffrn_measured_fraction_theta_full 0.995 _reflns_number_total 2257 _reflns_number_gt 1262 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0478715708 _diffrn_orient_matrix_UB_12 0.0255249618 _diffrn_orient_matrix_UB_13 0.0410855038 _diffrn_orient_matrix_UB_21 -0.0656954221 _diffrn_orient_matrix_UB_22 0.0191065316 _diffrn_orient_matrix_UB_23 -0.0505676773 _diffrn_orient_matrix_UB_31 -0.0382934173 _diffrn_orient_matrix_UB_32 -0.0009246329 _diffrn_orient_matrix_UB_33 0.0857308076 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' 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' 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 8.0709(6) _cell_length_b 22.2329(15) _cell_length_c 6.7382(6) _cell_angle_alpha 90.00 _cell_angle_beta 102.014(7) _cell_angle_gamma 90.00 _cell_volume 1182.62(16) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1447 _cell_measurement_theta_min 4.4196 _cell_measurement_theta_max 29.9984 _cell_special_details ? _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.145 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.95812 _exptl_absorpt_correction_T_max 0.99999 _exptl_absorpt_process_details ;SCALE3 ABSPACK - An Oxford Diffraction program (1.0.4,gui:1.0.3) (C) 2005 Oxford Diffraction Ltd. ; _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_diff_density_max 0.396 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.050 _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2257 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0813 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0738 _refine_ls_wR_factor_gt 0.0675 _refine_ls_goodness_of_fit_ref 0.809 _refine_ls_restrained_S_all 0.809 _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 N11 N -0.2469(3) 0.21962(10) 0.2401(4) 0.0248(5) Uani 1 1 d . . . N12 N 0.7585(3) 0.47656(10) 0.8903(4) 0.0264(5) Uani 1 1 d . . . O3 O 0.8764(2) 0.46261(8) 0.7699(3) 0.0462(5) Uani 1 1 d . . . O2 O -0.3154(2) 0.19091(7) 0.3915(3) 0.0318(4) Uani 1 1 d . . . O4 O 0.8386(2) 0.43337(8) 1.2876(3) 0.0273(4) Uani 1 1 d . . . H4A H 0.932(3) 0.4265(12) 1.332(4) 0.049(10) Uiso 1 1 d . . . H4B H 0.803(3) 0.4646(12) 1.355(4) 0.056(9) Uiso 1 1 d . . . H11A H -0.277(4) 0.1995(13) 0.107(5) 0.075(10) Uiso 1 1 d . . . H11C H -0.131(3) 0.2158(9) 0.281(4) 0.032(7) Uiso 1 1 d . . . H11B H -0.275(3) 0.2608(12) 0.234(4) 0.045(8) Uiso 1 1 d . . . H5A H 0.285(3) 0.6336(12) 0.666(4) 0.049(9) Uiso 1 1 d . . . H5B H 0.434(3) 0.6623(11) 0.699(4) 0.037(9) Uiso 1 1 d . . . H2 H -0.407(4) 0.1727(14) 0.325(5) 0.085(12) Uiso 1 1 d . . . H12C H 0.791(3) 0.4616(10) 1.019(4) 0.038(8) Uiso 1 1 d . . . H12B H 0.748(3) 0.5190(14) 0.891(4) 0.062(9) Uiso 1 1 d . . . H12A H 0.645(3) 0.4591(10) 0.826(4) 0.049(8) Uiso 1 1 d . . . H3 H 0.935(4) 0.4312(13) 0.832(5) 0.078(11) Uiso 1 1 d . . . O5 O 0.3414(3) 0.66739(8) 0.6425(3) 0.0265(4) Uani 1 1 d . . . N10 N 0.2875(2) 0.25915(8) 0.5937(3) 0.0205(5) Uani 1 1 d . . . N4 N 0.1763(2) 0.41125(8) 0.5211(3) 0.0231(5) Uani 1 1 d . . . N7 N 0.2314(2) 0.10633(7) 0.5736(3) 0.0230(5) Uani 1 1 d . . . C1 C 0.2605(3) 0.36135(9) 0.5796(3) 0.0175(5) Uani 1 1 d . . . N9 N 0.1885(2) 0.30266(7) 0.5288(3) 0.0195(4) Uani 1 1 d . . . N8 N 0.3216(2) 0.15550(7) 0.6372(3) 0.0222(5) Uani 1 1 d . . . O1 O 0.03866(19) 0.30114(6) 0.4305(3) 0.0339(5) Uani 1 1 d . . . N5 N 0.0765(2) 0.18226(7) 0.4390(3) 0.0226(5) Uani 1 1 d . . . N1 N 0.4144(2) 0.37009(7) 0.6887(3) 0.0230(5) Uani 1 1 d . . . N3 N 0.2860(2) 0.45477(8) 0.5985(3) 0.0278(5) Uani 1 1 d . . . N2 N 0.4282(2) 0.43014(8) 0.6993(3) 0.0263(5) Uani 1 1 d . . . N6 N 0.0861(2) 0.12199(8) 0.4569(3) 0.0233(5) Uani 1 1 d . . . C2 C 0.2232(3) 0.20114(9) 0.5527(3) 0.0176(5) 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 N11 0.0188(14) 0.0262(12) 0.0281(14) 0.0008(11) 0.0016(10) -0.0022(9) N12 0.0229(14) 0.0229(13) 0.0323(14) 0.0014(11) 0.0030(10) 0.0024(9) O3 0.0437(13) 0.0506(12) 0.0499(13) 0.0229(11) 0.0225(10) 0.0253(10) O2 0.0289(11) 0.0392(10) 0.0263(10) 0.0017(9) 0.0032(8) -0.0150(9) O4 0.0209(12) 0.0247(10) 0.0350(11) -0.0027(9) 0.0029(9) 0.0029(8) O5 0.0195(12) 0.0279(10) 0.0305(11) 0.0032(9) 0.0017(9) 0.0000(8) N10 0.0200(11) 0.0181(10) 0.0232(11) -0.0009(9) 0.0037(8) 0.0015(8) N4 0.0222(12) 0.0188(10) 0.0272(12) -0.0011(10) 0.0029(9) -0.0008(8) N7 0.0224(12) 0.0203(10) 0.0262(12) -0.0015(9) 0.0045(9) -0.0022(8) C1 0.0185(13) 0.0164(12) 0.0186(13) -0.0023(11) 0.0061(10) -0.0006(10) N9 0.0149(11) 0.0211(10) 0.0215(11) -0.0001(9) 0.0017(8) 0.0010(8) N8 0.0225(12) 0.0171(10) 0.0266(12) 0.0000(9) 0.0043(9) 0.0002(8) O1 0.0191(10) 0.0328(10) 0.0445(12) -0.0020(9) -0.0060(8) -0.0007(7) N5 0.0202(12) 0.0205(11) 0.0264(12) -0.0013(10) 0.0033(9) -0.0028(8) N1 0.0190(12) 0.0185(10) 0.0306(12) -0.0012(10) 0.0034(9) 0.0006(8) N3 0.0257(13) 0.0205(10) 0.0351(13) 0.0013(10) 0.0014(10) -0.0009(9) N2 0.0215(12) 0.0203(10) 0.0353(13) 0.0001(10) 0.0018(9) 0.0005(8) N6 0.0194(12) 0.0229(11) 0.0269(12) 0.0004(9) 0.0030(9) -0.0017(8) C2 0.0180(14) 0.0184(12) 0.0173(12) -0.0007(10) 0.0059(10) 0.0022(9) 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 N11 O2 1.410(2) . ? N11 H11A 0.99(3) . ? N11 H11C 0.92(2) . ? N11 H11B 0.94(3) . ? N12 O3 1.408(3) . ? N12 H12C 0.91(3) . ? N12 H12B 0.95(3) . ? N12 H12A 1.01(3) . ? O3 H3 0.90(3) . ? O2 H2 0.88(3) . ? O4 H4A 0.77(3) . ? O4 H4B 0.91(3) . ? O5 H5A 0.91(3) . ? O5 H5B 0.77(3) . ? N10 N9 1.273(2) . ? N10 C2 1.396(3) . ? N4 C1 1.318(2) . ? N4 N3 1.341(2) . ? N7 N6 1.316(2) . ? N7 N8 1.334(2) . ? C1 N1 1.320(2) . ? C1 N9 1.440(3) . ? N9 O1 1.253(2) . ? N8 C2 1.341(3) . ? N5 C2 1.336(3) . ? N5 N6 1.346(2) . ? N1 N2 1.340(2) . ? N3 N2 1.324(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 O2 N11 H11A 113.1(17) . . ? O2 N11 H11C 105.4(14) . . ? H11A N11 H11C 106(2) . . ? O2 N11 H11B 110.1(16) . . ? H11A N11 H11B 113(2) . . ? H11C N11 H11B 109.0(19) . . ? O3 N12 H12C 111.9(14) . . ? O3 N12 H12B 107.3(17) . . ? H12C N12 H12B 111(2) . . ? O3 N12 H12A 109.2(15) . . ? H12C N12 H12A 109(2) . . ? H12B N12 H12A 108(2) . . ? N12 O3 H3 105(2) . . ? N11 O2 H2 105(2) . . ? H4A O4 H4B 110(2) . . ? H5A O5 H5B 105(2) . . ? N9 N10 C2 116.93(17) . . ? C1 N4 N3 103.50(16) . . ? N6 N7 N8 109.52(16) . . ? N4 C1 N1 114.19(18) . . ? N4 C1 N9 122.30(18) . . ? N1 C1 N9 123.50(18) . . ? O1 N9 N10 128.99(18) . . ? O1 N9 C1 116.56(16) . . ? N10 N9 C1 114.44(16) . . ? N7 N8 C2 104.37(16) . . ? C2 N5 N6 103.51(17) . . ? C1 N1 N2 103.54(16) . . ? N2 N3 N4 109.42(16) . . ? N3 N2 N1 109.35(16) . . ? N7 N6 N5 110.15(16) . . ? N5 C2 N8 112.44(18) . . ? N5 C2 N10 130.69(19) . . ? N8 C2 N10 116.87(18) . . ? 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 N3 N4 C1 N1 0.3(3) . . . . ? N3 N4 C1 N9 179.9(2) . . . . ? C2 N10 N9 O1 -0.4(3) . . . . ? C2 N10 N9 C1 178.65(18) . . . . ? N4 C1 N9 O1 -2.1(3) . . . . ? N1 C1 N9 O1 177.5(2) . . . . ? N4 C1 N9 N10 178.7(2) . . . . ? N1 C1 N9 N10 -1.7(3) . . . . ? N6 N7 N8 C2 0.0(2) . . . . ? N4 C1 N1 N2 -0.1(3) . . . . ? N9 C1 N1 N2 -179.7(2) . . . . ? C1 N4 N3 N2 -0.3(2) . . . . ? N4 N3 N2 N1 0.3(3) . . . . ? C1 N1 N2 N3 -0.1(2) . . . . ? N8 N7 N6 N5 0.3(3) . . . . ? C2 N5 N6 N7 -0.5(2) . . . . ? N6 N5 C2 N8 0.5(3) . . . . ? N6 N5 C2 N10 179.9(2) . . . . ? N7 N8 C2 N5 -0.3(3) . . . . ? N7 N8 C2 N10 -179.78(18) . . . . ? N9 N10 C2 N5 6.8(3) . . . . ? N9 N10 C2 N8 -173.9(2) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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 O4 H4A N4 0.77(3) 2.14(3) 2.892(3) 167(3) 1_656 O4 H4B N3 0.91(3) 1.98(3) 2.847(3) 159(2) 3_667 N11 H11A O5 0.99(3) 1.80(3) 2.785(3) 176(3) 2_545 N11 H11C N5 0.92(2) 1.94(3) 2.801(3) 155(2) . N11 H11C O1 0.92(2) 2.43(2) 3.002(3) 120.1(16) . N11 H11B O5 0.94(3) 1.93(3) 2.788(3) 151(2) 3_566 N11 H11B O2 0.94(3) 2.50(3) 3.040(3) 116.2(19) 4_565 O5 H5A O4 0.91(3) 1.85(3) 2.763(3) 178(2) 3_667 O5 H5B N8 0.77(3) 2.06(3) 2.826(3) 175(3) 2_656 O2 H2 N1 0.88(3) 1.81(3) 2.687(2) 175(3) 4_465 O2 H2 N2 0.88(3) 2.69(3) 3.477(2) 149(3) 4_465 N12 H12C O4 0.91(3) 1.88(3) 2.790(3) 175(2) . N12 H12B N7 0.95(3) 1.96(3) 2.895(3) 169(2) 2_656 N12 H12A N2 1.01(3) 1.89(3) 2.899(3) 177(2) . O3 H3 N6 0.90(3) 1.78(3) 2.665(2) 169(3) 4_666 _geom_special_details ? data_gx428 _database_code_depnum_ccdc_archive 'CCDC 881231' _audit_author_name 'Joerg Stierstorfer' _audit_block_code ? _audit_creation_method ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _audit_creation_date ; 'Wed Jul 20 07:03:47 2011' ; _audit_update_record 26.07.2011 _chemical_name_systematic 'bisdiaminoguanidinium 5,5-azoxy-tetrazolate monohydrate' _chemical_compound_source ? _chemical_name_common 'bisdiaminoguanidinium 5,5-azoxy-tetrazolate monohydrate' _chemical_formula_moiety '2(C H8 N5), C2 N10 O, H2 O' _chemical_formula_sum 'C4 H18 N20 O2' _chemical_formula_weight 378.38 _cell_length_a 6.6702(5) _cell_length_b 10.0880(8) _cell_length_c 12.7314(11) _cell_angle_alpha 68.218(8) _cell_angle_beta 84.845(7) _cell_angle_gamma 76.760(7) _cell_volume 774.36(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3767 _cell_measurement_theta_min 4.1437 _cell_measurement_theta_max 32.2200 _cell_special_details ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9488 _exptl_absorpt_correction_T_max 0.9868 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 173 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power ? # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 11855 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.15 _diffrn_reflns_theta_max 26.25 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.25 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 3123 _reflns_number_gt 2649 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.0441752000 _diffrn_orient_matrix_UB_12 0.0381828000 _diffrn_orient_matrix_UB_13 0.0362099000 _diffrn_orient_matrix_UB_21 -0.0577076000 _diffrn_orient_matrix_UB_22 -0.0544204000 _diffrn_orient_matrix_UB_23 0.0278582000 _diffrn_orient_matrix_UB_31 0.0815633000 _diffrn_orient_matrix_UB_32 -0.0397782000 _diffrn_orient_matrix_UB_33 0.0388900000 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall -P1 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 0.993 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.053 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3123 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1075 _refine_ls_wR_factor_gt 0.1010 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 0.7318(2) 0.27076(13) -0.04220(11) 0.0251(3) Uani 1 1 d . . . N1 N 0.8242(2) 0.21618(16) -0.24017(13) 0.0249(3) Uani 1 1 d . . . N2 N 0.8880(3) 0.14444(18) -0.31251(13) 0.0296(4) Uani 1 1 d . . . N3 N 0.9047(2) 0.00267(18) -0.25634(15) 0.0302(4) Uani 1 1 d . . . N4 N 0.8536(2) -0.02202(17) -0.14710(14) 0.0269(4) Uani 1 1 d . . . N5 N 0.7425(2) 0.14249(16) -0.03993(14) 0.0255(4) Uani 1 1 d . . . N6 N 0.7075(2) 0.03246(16) 0.04169(14) 0.0272(4) Uani 1 1 d . . . N7 N 0.6199(2) 0.15997(16) 0.18197(13) 0.0223(3) Uani 1 1 d . . . N8 N 0.5802(2) 0.09884(17) 0.29291(13) 0.0259(3) Uani 1 1 d . . . N9 N 0.5918(2) -0.04208(17) 0.32076(14) 0.0279(4) Uani 1 1 d . . . N10 N 0.6389(2) -0.07865(16) 0.23029(14) 0.0274(4) Uani 1 1 d . . . C1 C 0.8063(2) 0.10993(19) -0.14254(14) 0.0200(4) Uani 1 1 d . . . C2 C 0.6557(3) 0.04711(19) 0.14628(15) 0.0217(4) Uani 1 1 d . . . N11 N 0.6403(2) 0.47091(18) 0.11658(14) 0.0253(4) Uani 1 1 d . . . N12 N 0.9712(2) 0.33721(16) 0.15755(13) 0.0225(3) Uani 1 1 d . . . N13 N 1.1810(2) 0.33572(18) 0.16557(15) 0.0248(3) Uani 1 1 d . . . N14 N 0.9066(2) 0.58606(15) 0.10702(13) 0.0206(3) Uani 1 1 d . . . N15 N 0.7637(2) 0.72063(16) 0.07727(15) 0.0239(3) Uani 1 1 d . . . C3 C 0.8378(3) 0.46567(18) 0.12633(14) 0.0185(4) Uani 1 1 d . . . N16 N 1.1456(2) 0.47312(18) 0.37063(14) 0.0238(3) Uani 1 1 d . . . N17 N 0.8063(2) 0.59350(17) 0.35751(13) 0.0237(3) Uani 1 1 d . . . N18 N 0.5974(3) 0.58663(18) 0.37452(16) 0.0280(4) Uani 1 1 d . . . N19 N 0.8853(2) 0.34339(16) 0.41526(13) 0.0230(3) Uani 1 1 d . . . N20 N 1.0351(3) 0.21250(17) 0.43456(15) 0.0255(4) Uani 1 1 d . . . C4 C 0.9478(3) 0.46825(18) 0.38160(14) 0.0195(4) Uani 1 1 d . . . O2 O 0.5156(2) 0.23445(15) 0.45733(13) 0.0259(3) Uani 1 1 d . . . H2B H 0.530(4) 0.191(3) 0.411(2) 0.046(7) Uiso 1 1 d . . . H2A H 0.486(4) 0.175(3) 0.519(3) 0.052(8) Uiso 1 1 d . . . H13B H 1.251(3) 0.296(2) 0.1194(19) 0.030(6) Uiso 1 1 d . . . H15B H 0.812(4) 0.783(3) 0.018(2) 0.038(6) Uiso 1 1 d . . . H14 H 1.034(3) 0.579(2) 0.1142(17) 0.023(5) Uiso 1 1 d . . . H15A H 0.755(3) 0.752(2) 0.1313(19) 0.028(6) Uiso 1 1 d . . . H11B H 0.605(3) 0.394(2) 0.1261(18) 0.026(5) Uiso 1 1 d . . . H18A H 0.554(4) 0.616(3) 0.432(2) 0.048(7) Uiso 1 1 d . . . H12 H 0.929(3) 0.261(2) 0.1664(18) 0.027(5) Uiso 1 1 d . . . H16B H 1.239(3) 0.393(2) 0.3887(18) 0.027(5) Uiso 1 1 d . . . H20A H 1.000(3) 0.167(2) 0.3942(19) 0.031(6) Uiso 1 1 d . . . H11A H 0.556(4) 0.556(3) 0.0972(19) 0.035(6) Uiso 1 1 d . . . H20B H 1.031(4) 0.158(3) 0.508(2) 0.044(7) Uiso 1 1 d . . . H17 H 0.844(3) 0.671(3) 0.3416(19) 0.031(6) Uiso 1 1 d . . . H16A H 1.179(3) 0.559(3) 0.3350(19) 0.029(6) Uiso 1 1 d . . . H19 H 0.758(4) 0.340(2) 0.4268(19) 0.036(6) Uiso 1 1 d . . . H18B H 0.533(4) 0.651(3) 0.314(2) 0.039(7) Uiso 1 1 d . . . H13A H 1.217(4) 0.280(3) 0.240(2) 0.045(7) 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 0.0292(7) 0.0116(6) 0.0350(7) -0.0079(5) 0.0003(5) -0.0064(5) N1 0.0251(8) 0.0201(8) 0.0270(8) -0.0054(6) 0.0003(6) -0.0056(6) N2 0.0284(9) 0.0338(9) 0.0224(8) -0.0062(7) 0.0009(6) -0.0056(7) N3 0.0260(9) 0.0283(9) 0.0388(10) -0.0169(8) -0.0038(7) -0.0012(7) N4 0.0254(8) 0.0204(8) 0.0317(9) -0.0049(7) -0.0027(6) -0.0052(6) N5 0.0194(8) 0.0163(7) 0.0384(9) -0.0060(7) -0.0058(6) -0.0038(6) N6 0.0291(9) 0.0194(8) 0.0315(9) -0.0063(7) -0.0017(7) -0.0063(6) N7 0.0219(8) 0.0187(7) 0.0259(8) -0.0078(6) 0.0021(6) -0.0048(6) N8 0.0276(8) 0.0251(8) 0.0258(8) -0.0107(7) 0.0036(6) -0.0060(6) N9 0.0290(9) 0.0228(8) 0.0289(9) -0.0060(7) 0.0023(7) -0.0064(6) N10 0.0286(9) 0.0186(8) 0.0350(9) -0.0096(7) -0.0022(7) -0.0043(6) C1 0.0153(8) 0.0219(9) 0.0213(9) -0.0052(7) -0.0015(6) -0.0049(7) C2 0.0172(8) 0.0243(9) 0.0250(9) -0.0121(7) -0.0007(7) -0.0017(7) N11 0.0236(8) 0.0143(8) 0.0370(9) -0.0068(7) -0.0024(7) -0.0052(7) N12 0.0214(8) 0.0145(7) 0.0313(9) -0.0076(6) -0.0022(6) -0.0036(6) N13 0.0212(8) 0.0257(8) 0.0277(9) -0.0113(7) -0.0008(7) -0.0024(6) N14 0.0210(8) 0.0144(7) 0.0258(8) -0.0065(6) -0.0019(6) -0.0034(6) N15 0.0306(9) 0.0127(7) 0.0271(9) -0.0055(7) -0.0023(7) -0.0038(6) C3 0.0231(9) 0.0172(8) 0.0151(8) -0.0061(7) 0.0015(6) -0.0045(7) N16 0.0241(8) 0.0167(8) 0.0283(9) -0.0044(7) -0.0015(6) -0.0056(7) N17 0.0254(8) 0.0170(8) 0.0271(8) -0.0056(6) 0.0022(6) -0.0062(6) N18 0.0257(9) 0.0252(9) 0.0313(9) -0.0096(8) 0.0051(7) -0.0047(7) N19 0.0223(8) 0.0171(7) 0.0272(8) -0.0054(6) 0.0014(6) -0.0048(6) N20 0.0305(9) 0.0167(8) 0.0275(9) -0.0065(7) 0.0002(7) -0.0041(6) C4 0.0259(9) 0.0192(9) 0.0129(8) -0.0051(7) 0.0002(6) -0.0053(7) O2 0.0317(8) 0.0220(7) 0.0263(7) -0.0096(6) 0.0034(6) -0.0103(6) 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 N5 1.2692(19) . ? N1 C1 1.323(2) . ? N1 N2 1.355(2) . ? N2 N3 1.323(2) . ? N3 N4 1.345(2) . ? N4 C1 1.318(2) . ? N5 N6 1.259(2) . ? N5 C1 1.466(2) . ? N6 C2 1.398(2) . ? N7 C2 1.341(2) . ? N7 N8 1.344(2) . ? N8 N9 1.317(2) . ? N9 N10 1.326(2) . ? N10 C2 1.343(2) . ? N11 C3 1.321(2) . ? N11 H11B 0.83(2) . ? N11 H11A 0.87(2) . ? N12 C3 1.335(2) . ? N12 N13 1.408(2) . ? N12 H12 0.84(2) . ? N13 H13B 0.87(2) . ? N13 H13A 0.92(3) . ? N14 C3 1.326(2) . ? N14 N15 1.409(2) . ? N14 H14 0.84(2) . ? N15 H15B 0.88(3) . ? N15 H15A 0.85(2) . ? N16 C4 1.324(2) . ? N16 H16B 0.87(2) . ? N16 H16A 0.88(2) . ? N17 C4 1.341(2) . ? N17 N18 1.405(2) . ? N17 H17 0.83(2) . ? N18 H18A 0.88(3) . ? N18 H18B 0.87(3) . ? N19 C4 1.324(2) . ? N19 N20 1.415(2) . ? N19 H19 0.86(2) . ? N20 H20A 0.88(2) . ? N20 H20B 0.89(3) . ? O2 H2B 0.85(3) . ? O2 H2A 0.83(3) . ? 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 C1 N1 N2 103.36(14) . . ? N3 N2 N1 108.90(15) . . ? N2 N3 N4 109.90(15) . . ? C1 N4 N3 103.41(15) . . ? N6 N5 O1 128.55(17) . . ? N6 N5 C1 112.43(15) . . ? O1 N5 C1 119.01(15) . . ? N5 N6 C2 118.08(16) . . ? C2 N7 N8 103.45(14) . . ? N9 N8 N7 110.08(14) . . ? N8 N9 N10 109.84(15) . . ? N9 N10 C2 104.42(14) . . ? N4 C1 N1 114.42(16) . . ? N4 C1 N5 124.95(15) . . ? N1 C1 N5 120.62(15) . . ? N7 C2 N10 112.22(16) . . ? N7 C2 N6 133.99(17) . . ? N10 C2 N6 113.79(15) . . ? C3 N11 H11B 118.0(15) . . ? C3 N11 H11A 118.2(15) . . ? H11B N11 H11A 124(2) . . ? C3 N12 N13 118.40(15) . . ? C3 N12 H12 119.1(14) . . ? N13 N12 H12 122.3(14) . . ? N12 N13 H13B 108.5(14) . . ? N12 N13 H13A 105.8(15) . . ? H13B N13 H13A 111(2) . . ? C3 N14 N15 118.54(15) . . ? C3 N14 H14 118.8(14) . . ? N15 N14 H14 122.7(14) . . ? N14 N15 H15B 108.0(15) . . ? N14 N15 H15A 108.6(14) . . ? H15B N15 H15A 108(2) . . ? N11 C3 N14 121.18(16) . . ? N11 C3 N12 119.86(16) . . ? N14 C3 N12 118.95(16) . . ? C4 N16 H16B 120.2(14) . . ? C4 N16 H16A 118.4(14) . . ? H16B N16 H16A 121(2) . . ? C4 N17 N18 118.61(16) . . ? C4 N17 H17 119.5(15) . . ? N18 N17 H17 121.4(15) . . ? N17 N18 H18A 106.7(17) . . ? N17 N18 H18B 106.4(16) . . ? H18A N18 H18B 108(2) . . ? C4 N19 N20 118.52(16) . . ? C4 N19 H19 122.0(15) . . ? N20 N19 H19 119.5(15) . . ? N19 N20 H20A 107.4(14) . . ? N19 N20 H20B 107.8(16) . . ? H20A N20 H20B 109(2) . . ? N19 C4 N16 121.96(16) . . ? N19 C4 N17 118.92(17) . . ? N16 C4 N17 119.12(16) . . ? H2B O2 H2A 106(2) . . ? 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 C1 N1 N2 N3 0.01(19) . . . . ? N1 N2 N3 N4 -0.2(2) . . . . ? N2 N3 N4 C1 0.23(19) . . . . ? O1 N5 N6 C2 -2.2(3) . . . . ? C1 N5 N6 C2 176.72(14) . . . . ? C2 N7 N8 N9 -0.11(19) . . . . ? N7 N8 N9 N10 0.0(2) . . . . ? N8 N9 N10 C2 0.12(19) . . . . ? N3 N4 C1 N1 -0.2(2) . . . . ? N3 N4 C1 N5 -179.02(15) . . . . ? N2 N1 C1 N4 0.2(2) . . . . ? N2 N1 C1 N5 178.99(15) . . . . ? N6 N5 C1 N4 -9.9(2) . . . . ? O1 N5 C1 N4 169.16(16) . . . . ? N6 N5 C1 N1 171.39(15) . . . . ? O1 N5 C1 N1 -9.5(2) . . . . ? N8 N7 C2 N10 0.19(19) . . . . ? N8 N7 C2 N6 -179.32(19) . . . . ? N9 N10 C2 N7 -0.2(2) . . . . ? N9 N10 C2 N6 179.42(15) . . . . ? N5 N6 C2 N7 5.0(3) . . . . ? N5 N6 C2 N10 -174.47(15) . . . . ? N15 N14 C3 N11 0.9(2) . . . . ? N15 N14 C3 N12 -178.20(15) . . . . ? N13 N12 C3 N11 179.12(16) . . . . ? N13 N12 C3 N14 -1.7(2) . . . . ? N20 N19 C4 N16 -3.1(3) . . . . ? N20 N19 C4 N17 176.62(15) . . . . ? N18 N17 C4 N19 3.2(2) . . . . ? N18 N17 C4 N16 -177.05(16) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2B N8 0.85(3) 2.00(3) 2.852(2) 175(2) . O2 H2A N9 0.83(3) 2.08(3) 2.909(2) 174(3) 2_656 N13 H13B N7 0.87(2) 2.56(2) 3.036(2) 115.0(17) 1_655 N13 H13B N15 0.87(2) 2.58(2) 3.320(3) 142.5(18) 2_765 N15 H15B N4 0.88(3) 2.33(3) 3.188(2) 166(2) 1_565 N14 H14 O1 0.84(2) 2.32(2) 2.990(2) 136.4(18) 2_765 N15 H15A N10 0.85(2) 2.43(2) 3.233(2) 156.9(19) 1_565 N11 H11B N7 0.83(2) 2.18(2) 2.965(2) 159(2) . N18 H18A O2 0.88(3) 2.38(3) 3.219(2) 160(2) 2_666 N12 H12 N7 0.84(2) 2.46(2) 3.188(2) 144.4(18) . N12 H12 N3 0.84(2) 2.50(2) 3.116(2) 131.0(18) 2_755 N12 H12 N4 0.84(2) 2.60(2) 3.174(2) 126.6(17) 2_755 N16 H16B O2 0.87(2) 2.15(2) 2.984(2) 160.7(19) 1_655 N11 H11A O1 0.87(2) 2.24(2) 3.079(2) 161(2) 2_665 N20 H20B N2 0.89(3) 2.37(3) 3.147(2) 146(2) 1_556 N17 H17 N10 0.83(2) 2.52(2) 3.077(2) 125.6(19) 1_565 N16 H16A N1 0.88(2) 2.14(2) 2.998(2) 164.9(19) 2_765 N19 H19 O2 0.86(2) 2.06(2) 2.854(2) 153(2) . N18 H18B N1 0.87(3) 2.52(3) 3.251(2) 141(2) 2_665 N13 H13A N20 0.92(3) 2.58(3) 3.319(3) 137.2(19) . N13 H13A N8 0.92(3) 2.65(2) 3.227(2) 121.4(19) 1_655 _geom_special_details ? _iucr_refine_instructions_details ; TITL v1 in P-1 CELL 0.71073 6.6702 10.0880 12.7314 68.218 84.845 76.760 ZERR 2.00 0.0005 0.0008 0.0011 0.008 0.007 0.007 LATT 1 SFAC C N O H UNIT 8 40 4 36 MERG 2 OMIT -2.00 52.50 FMAP 2 PLAN 20 SIZE 0.10 0.35 0.40 ACTA BOND $H CONF HTAB EQIV $1 -x+1, -y, -z+1 EQIV $2 x+1, y, z EQIV $3 -x+2, -y+1, -z EQIV $4 x, y+1, z EQIV $5 -x+1, -y+1, -z+1 EQIV $6 -x+2, -y, -z EQIV $7 -x+1, -y+1, -z EQIV $8 x, y, z+1 HTAB O2 N8 HTAB O2 N9_$1 HTAB N13 N7_$2 HTAB N13 N15_$3 HTAB N15 N4_$4 HTAB N14 O1_$3 HTAB N15 N10_$4 HTAB N11 N7 HTAB N18 O2_$5 HTAB N12 N7 HTAB N12 N3_$6 HTAB N12 N4_$6 HTAB N16 O2_$2 HTAB N11 O1_$7 HTAB N20 N2_$8 HTAB N17 N10_$4 HTAB N16 N1_$3 HTAB N19 O2 HTAB N18 N1_$7 HTAB N13 N20 HTAB N13 N8_$2 L.S. 5 TEMP -100.00 WGHT 0.043700 0.505400 FVAR 6.19398 O1 3 0.731819 0.270764 -0.042200 11.00000 0.02921 0.01163 = 0.03499 -0.00787 0.00033 -0.00636 N1 2 0.824190 0.216185 -0.240167 11.00000 0.02512 0.02005 = 0.02699 -0.00538 0.00031 -0.00559 N2 2 0.887972 0.144443 -0.312511 11.00000 0.02839 0.03380 = 0.02237 -0.00620 0.00085 -0.00559 N3 2 0.904733 0.002669 -0.256340 11.00000 0.02595 0.02833 = 0.03885 -0.01686 -0.00375 -0.00124 N4 2 0.853599 -0.022021 -0.147102 11.00000 0.02543 0.02040 = 0.03172 -0.00493 -0.00272 -0.00525 N5 2 0.742481 0.142486 -0.039932 11.00000 0.01945 0.01632 = 0.03841 -0.00602 -0.00583 -0.00380 N6 2 0.707454 0.032458 0.041687 11.00000 0.02906 0.01943 = 0.03146 -0.00629 -0.00169 -0.00626 N7 2 0.619863 0.159967 0.181965 11.00000 0.02189 0.01865 = 0.02593 -0.00780 0.00207 -0.00478 N8 2 0.580249 0.098844 0.292906 11.00000 0.02756 0.02511 = 0.02580 -0.01069 0.00360 -0.00602 N9 2 0.591801 -0.042084 0.320765 11.00000 0.02896 0.02282 = 0.02893 -0.00598 0.00230 -0.00638 N10 2 0.638885 -0.078654 0.230290 11.00000 0.02861 0.01858 = 0.03504 -0.00962 -0.00222 -0.00430 C1 1 0.806306 0.109928 -0.142541 11.00000 0.01528 0.02192 = 0.02129 -0.00516 -0.00153 -0.00491 C2 1 0.655682 0.047112 0.146276 11.00000 0.01724 0.02432 = 0.02501 -0.01214 -0.00074 -0.00170 N11 2 0.640344 0.470907 0.116584 11.00000 0.02362 0.01426 = 0.03695 -0.00684 -0.00238 -0.00522 N12 2 0.971250 0.337207 0.157552 11.00000 0.02144 0.01447 = 0.03133 -0.00758 -0.00219 -0.00362 N13 2 1.180980 0.335723 0.165573 11.00000 0.02124 0.02566 = 0.02773 -0.01127 -0.00084 -0.00237 N14 2 0.906572 0.586056 0.107015 11.00000 0.02104 0.01440 = 0.02579 -0.00647 -0.00185 -0.00341 N15 2 0.763709 0.720625 0.077272 11.00000 0.03065 0.01269 = 0.02706 -0.00554 -0.00232 -0.00383 C3 1 0.837758 0.465666 0.126333 11.00000 0.02311 0.01715 = 0.01512 -0.00608 0.00146 -0.00447 N16 2 1.145566 0.473117 0.370628 11.00000 0.02406 0.01665 = 0.02832 -0.00439 -0.00151 -0.00560 N17 2 0.806316 0.593501 0.357512 11.00000 0.02538 0.01696 = 0.02706 -0.00556 0.00224 -0.00621 N18 2 0.597368 0.586626 0.374520 11.00000 0.02567 0.02517 = 0.03129 -0.00959 0.00510 -0.00467 N19 2 0.885288 0.343392 0.415263 11.00000 0.02226 0.01714 = 0.02725 -0.00541 0.00144 -0.00477 N20 2 1.035098 0.212504 0.434562 11.00000 0.03046 0.01671 = 0.02748 -0.00653 0.00025 -0.00406 C4 1 0.947788 0.468255 0.381595 11.00000 0.02594 0.01919 = 0.01287 -0.00512 0.00024 -0.00530 O2 3 0.515567 0.234448 0.457332 11.00000 0.03167 0.02202 = 0.02626 -0.00956 0.00341 -0.01026 H2B 4 0.529961 0.190611 0.410678 11.00000 0.04602 H2A 4 0.486032 0.175064 0.518651 11.00000 0.05159 H13B 4 1.251256 0.296008 0.119423 11.00000 0.02979 H15B 4 0.812129 0.783156 0.018141 11.00000 0.03798 H14 4 1.033564 0.578842 0.114231 11.00000 0.02328 H15A 4 0.755138 0.752100 0.131267 11.00000 0.02831 H11B 4 0.604925 0.394001 0.126067 11.00000 0.02580 H18A 4 0.554226 0.615715 0.431660 11.00000 0.04762 H12 4 0.929041 0.261009 0.166356 11.00000 0.02705 H16B 4 1.239310 0.392525 0.388708 11.00000 0.02683 H20A 4 1.000081 0.166615 0.394198 11.00000 0.03055 H11A 4 0.555949 0.555794 0.097212 11.00000 0.03514 H20B 4 1.031045 0.158246 0.507595 11.00000 0.04357 H17 4 0.844032 0.671320 0.341560 11.00000 0.03062 H16A 4 1.179347 0.558761 0.334995 11.00000 0.02899 H19 4 0.757631 0.339635 0.426767 11.00000 0.03626 H18B 4 0.533075 0.650747 0.313619 11.00000 0.03858 H13A 4 1.216893 0.279913 0.239726 11.00000 0.04470 HKLF 4 REM v1 in P-1 REM R1 = 0.0427 for 2649 Fo > 4sig(Fo) and 0.0512 for all 3123 data REM 307 parameters refined using 0 restraints END WGHT 0.0437 0.5054 REM Highest difference peak 0.993, deepest hole -0.326, 1-sigma level 0.053 Q1 1 0.7573 0.0388 -0.0390 11.00000 0.05 0.99 Q2 1 0.7009 0.1343 0.0310 11.00000 0.05 0.69 Q3 1 0.6842 -0.0373 0.1744 11.00000 0.05 0.21 Q4 1 0.6822 0.2364 0.1449 11.00000 0.05 0.19 Q5 1 0.8100 0.0362 -0.1495 11.00000 0.05 0.18 Q6 1 1.1299 0.2411 0.3730 11.00000 0.05 0.18 Q7 1 0.6578 0.6699 0.0867 11.00000 0.05 0.18 Q8 1 0.6647 0.1060 0.1568 11.00000 0.05 0.17 Q9 1 0.8708 0.5178 0.1528 11.00000 0.05 0.16 Q10 1 1.2200 0.4199 0.1330 11.00000 0.05 0.15 Q11 1 0.6378 0.0516 0.1128 11.00000 0.05 0.15 Q12 1 0.9071 0.4027 0.1638 11.00000 0.05 0.14 Q13 1 0.7520 0.6821 0.4575 11.00000 0.05 0.14 Q14 1 0.8461 0.5678 0.2869 11.00000 0.05 0.14 Q15 1 0.8448 -0.1274 -0.0843 11.00000 0.05 0.14 Q16 1 0.9133 0.4073 0.1165 11.00000 0.05 0.14 Q17 1 0.8456 0.1571 -0.1849 11.00000 0.05 0.14 Q18 1 0.4820 -0.0583 0.3634 11.00000 0.05 0.14 Q19 1 0.9087 0.2786 -0.2543 11.00000 0.05 0.13 Q20 1 0.9267 0.4023 0.4161 11.00000 0.05 0.13 ; # start Validation Reply Form _vrf_DIFMX01_gx428 ; PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00 RESPONSE: Remaining electron density is caused by disordered azoxy-tetrazolate dianion ; _vrf_PLAT097_gx428 ; PROBLEM: Large Reported Max. (Positive) Residual Density 0.99 eA-3 RESPONSE: Remaining electron density is caused by disordered azoxy-tetrazolate dianion ; data_gx514 _database_code_depnum_ccdc_archive 'CCDC 881233' _audit_author_name 'Joerg Stierstorfer' _audit_block_code ? _audit_creation_method ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _audit_creation_date ; 'Mon Sep 05 17:24:33 2011' ; _audit_update_record 07.09.2011 _chemical_name_systematic 'diaminouronium 5,5-azoxytetrazolete tetrahydrate' _chemical_compound_source ? _chemical_name_common 'diaminouronium 5,5-azoxytetrazolete tetrahydrate' _chemical_formula_moiety ? _chemical_formula_sum 'C5 H18 N24 O7' _chemical_formula_weight 526.43 _cell_length_a 13.0674(10) _cell_length_b 6.8891(7) _cell_length_c 24.3334(18) _cell_angle_alpha 90.00 _cell_angle_beta 104.661(7) _cell_angle_gamma 90.00 _cell_volume 2119.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2064 _cell_measurement_theta_min 4.1647 _cell_measurement_theta_max 33.6913 _cell_special_details ? _exptl_crystal_description platelet _exptl_crystal_colour yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.650 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.145 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9730 _exptl_absorpt_correction_T_max 0.9971 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 173 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power ? # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 10384 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0583 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 25.75 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.75 _diffrn_measured_fraction_theta_full 0.995 _reflns_number_total 4026 _reflns_number_gt 2898 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0057605000 _diffrn_orient_matrix_UB_12 0.0985352000 _diffrn_orient_matrix_UB_13 -0.0071363000 _diffrn_orient_matrix_UB_21 -0.0526583000 _diffrn_orient_matrix_UB_22 0.0186242000 _diffrn_orient_matrix_UB_23 0.0013618000 _diffrn_orient_matrix_UB_31 0.0184913000 _diffrn_orient_matrix_UB_32 0.0233378000 _diffrn_orient_matrix_UB_33 0.0292414000 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 0.225 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.050 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 4026 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0659 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0816 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 O1 O 0.18133(12) 0.7602(2) -0.00051(7) 0.0362(4) Uani 1 1 d . . . N1 N 0.01756(13) 0.6535(2) -0.08600(7) 0.0235(4) Uani 1 1 d . . . N2 N -0.08198(14) 0.6188(3) -0.11656(7) 0.0248(4) Uani 1 1 d . . . N3 N -0.14928(14) 0.6540(3) -0.08510(7) 0.0240(4) Uani 1 1 d . . . N4 N -0.09673(13) 0.7134(2) -0.03292(7) 0.0231(4) Uani 1 1 d . . . N5 N 0.09183(13) 0.7653(2) 0.00917(7) 0.0217(4) Uani 1 1 d . . . N6 N 0.06972(13) 0.8137(3) 0.05577(7) 0.0226(4) Uani 1 1 d . . . N7 N 0.13840(14) 0.9247(3) 0.14882(7) 0.0258(4) Uani 1 1 d . . . N8 N 0.23420(14) 0.9766(3) 0.18172(8) 0.0279(5) Uani 1 1 d . . . N9 N 0.30706(14) 0.9563(3) 0.15406(8) 0.0277(5) Uani 1 1 d . . . N10 N 0.25846(14) 0.8885(3) 0.10229(8) 0.0227(4) Uani 1 1 d . . . C2 C 0.15457(16) 0.8706(3) 0.09933(9) 0.0210(5) Uani 1 1 d . . . C1 C 0.00332(16) 0.7102(3) -0.03641(9) 0.0182(5) Uani 1 1 d . . . O2 O 0.34513(11) 0.2757(2) 0.04649(6) 0.0289(4) Uani 1 1 d . . . N19 N 0.35316(15) 0.4988(3) 0.19484(8) 0.0301(5) Uani 1 1 d . . . N18 N 0.44783(15) 0.5629(3) 0.21901(8) 0.0307(5) Uani 1 1 d . . . N17 N 0.51379(14) 0.5391(3) 0.18503(7) 0.0268(4) Uani 1 1 d . . . N16 N 0.50166(13) 0.4063(2) 0.09454(7) 0.0214(4) Uani 1 1 d . . . N15 N 0.44047(13) 0.3177(2) 0.05238(7) 0.0196(4) Uani 1 1 d . . . N11 N 0.42965(14) 0.1845(2) -0.04000(7) 0.0223(4) Uani 1 1 d . . . N12 N 0.50152(13) 0.1500(2) -0.06978(7) 0.0231(4) Uani 1 1 d . . . N13 N 0.59682(14) 0.2055(2) -0.04006(7) 0.0227(4) Uani 1 1 d . . . N14 N 0.59039(13) 0.2791(2) 0.01024(7) 0.0199(4) Uani 1 1 d . . . N20 N 0.35700(15) 0.4311(3) 0.14354(8) 0.0228(4) Uani 1 1 d . . . C4 C 0.45590(16) 0.4558(3) 0.13809(9) 0.0203(5) Uani 1 1 d . . . C3 C 0.48786(16) 0.2620(3) 0.00753(9) 0.0177(5) Uani 1 1 d . . . O3 O 0.08217(12) 0.7762(2) 0.30087(6) 0.0290(4) Uani 1 1 d . . . N21 N 0.18860(14) 0.5635(3) 0.27037(8) 0.0226(4) Uani 1 1 d . . . N22 N 0.09700(15) 0.4846(3) 0.23256(9) 0.0235(4) Uani 1 1 d . . . N23 N 0.24708(15) 0.7153(3) 0.35638(8) 0.0219(4) Uani 1 1 d . . . N24 N 0.23496(16) 0.8822(3) 0.38913(8) 0.0228(4) Uani 1 1 d . . . C5 C 0.16650(16) 0.6913(3) 0.30878(9) 0.0193(5) Uani 1 1 d . . . O7 O 0.19039(15) 0.2515(2) 0.42724(8) 0.0317(4) Uani 1 1 d . . . O5 O 0.26714(15) 0.1438(2) 0.29927(8) 0.0299(4) Uani 1 1 d . . . O4 O 0.58006(14) 0.0588(3) 0.16906(8) 0.0358(5) Uani 1 1 d . . . O6 O 0.04466(14) 0.2868(2) 0.32202(7) 0.0273(4) Uani 1 1 d . . . H24B H 0.290(2) 0.876(3) 0.4234(10) 0.038(7) Uiso 1 1 d . . . H21 H 0.2382(19) 0.479(3) 0.2816(9) 0.032(7) Uiso 1 1 d . . . H22B H 0.1121(18) 0.440(3) 0.1977(11) 0.041(7) Uiso 1 1 d . . . H10 H 0.2953(19) 0.855(3) 0.0760(11) 0.046(8) Uiso 1 1 d . . . H24A H 0.165(2) 0.884(3) 0.3963(10) 0.044(7) Uiso 1 1 d . . . H6B H -0.001(2) 0.344(4) 0.3322(11) 0.048(9) Uiso 1 1 d . . . H24C H 0.241(2) 0.999(4) 0.3666(11) 0.055(8) Uiso 1 1 d . . . H7A H 0.254(2) 0.295(4) 0.4385(12) 0.058(9) Uiso 1 1 d . . . H20 H 0.295(2) 0.392(4) 0.1186(11) 0.057(9) Uiso 1 1 d . . . H5A H 0.335(2) 0.128(4) 0.3048(12) 0.062(10) Uiso 1 1 d . . . H22A H 0.070(2) 0.403(4) 0.2545(12) 0.057(9) Uiso 1 1 d . . . H22C H 0.047(2) 0.585(4) 0.2212(12) 0.062(9) Uiso 1 1 d . . . H5B H 0.248(2) 0.087(4) 0.2680(14) 0.069(11) Uiso 1 1 d . . . H23 H 0.312(2) 0.690(3) 0.3536(11) 0.043(8) Uiso 1 1 d . . . H6A H 0.095(3) 0.284(5) 0.3566(16) 0.092(12) Uiso 1 1 d . . . H4B H 0.547(2) -0.014(4) 0.1436(12) 0.050(9) Uiso 1 1 d . . . H4A H 0.559(2) 0.070(4) 0.1990(14) 0.077(11) Uiso 1 1 d . . . H7B H 0.173(3) 0.251(5) 0.4579(15) 0.078(12) 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 0.0162(9) 0.0653(12) 0.0289(9) -0.0131(8) 0.0092(8) -0.0051(7) N1 0.0187(10) 0.0306(11) 0.0216(10) -0.0028(8) 0.0056(8) -0.0001(8) N2 0.0180(10) 0.0328(11) 0.0235(10) -0.0035(8) 0.0050(8) 0.0002(8) N3 0.0206(10) 0.0313(11) 0.0210(10) -0.0029(8) 0.0070(8) -0.0006(8) N4 0.0171(10) 0.0326(11) 0.0200(10) -0.0013(8) 0.0056(8) -0.0015(8) N5 0.0163(10) 0.0283(11) 0.0223(10) -0.0008(8) 0.0084(8) 0.0001(7) N6 0.0208(10) 0.0301(11) 0.0181(9) -0.0029(8) 0.0074(8) -0.0040(8) N7 0.0245(11) 0.0342(11) 0.0198(10) -0.0046(8) 0.0077(9) -0.0037(8) N8 0.0255(11) 0.0355(12) 0.0235(10) -0.0047(8) 0.0079(9) -0.0059(8) N9 0.0259(11) 0.0358(12) 0.0220(10) -0.0033(8) 0.0072(9) -0.0033(8) N10 0.0192(10) 0.0290(11) 0.0205(10) -0.0033(8) 0.0059(9) -0.0030(8) C2 0.0205(12) 0.0219(12) 0.0221(12) 0.0000(9) 0.0083(10) -0.0034(9) C1 0.0160(11) 0.0226(12) 0.0160(11) -0.0013(9) 0.0039(9) -0.0007(8) O2 0.0133(8) 0.0474(10) 0.0274(9) -0.0084(7) 0.0080(7) -0.0075(7) N19 0.0272(11) 0.0405(12) 0.0245(10) -0.0061(9) 0.0101(9) -0.0017(9) N18 0.0279(12) 0.0420(12) 0.0239(10) -0.0054(9) 0.0098(9) -0.0019(9) N17 0.0232(11) 0.0377(12) 0.0204(10) -0.0062(8) 0.0070(9) -0.0027(8) N16 0.0191(10) 0.0274(10) 0.0177(9) -0.0034(8) 0.0047(8) -0.0029(7) N15 0.0177(10) 0.0245(10) 0.0175(9) 0.0004(8) 0.0059(8) -0.0005(7) N11 0.0213(10) 0.0270(10) 0.0200(10) -0.0035(8) 0.0077(8) -0.0026(7) N12 0.0186(10) 0.0302(11) 0.0215(10) -0.0025(8) 0.0070(8) -0.0006(8) N13 0.0202(10) 0.0284(10) 0.0201(9) -0.0027(8) 0.0063(8) -0.0010(8) N14 0.0183(10) 0.0236(10) 0.0189(9) -0.0008(7) 0.0071(8) 0.0010(7) N20 0.0205(11) 0.0313(11) 0.0177(10) -0.0035(8) 0.0070(9) -0.0008(8) C4 0.0186(12) 0.0242(12) 0.0186(11) 0.0011(9) 0.0060(9) 0.0004(9) C3 0.0183(11) 0.0189(11) 0.0176(11) -0.0006(9) 0.0075(9) 0.0000(8) O3 0.0208(9) 0.0369(10) 0.0253(9) -0.0085(7) -0.0014(7) 0.0096(7) N21 0.0156(10) 0.0299(11) 0.0209(10) -0.0074(8) 0.0021(8) 0.0011(8) N22 0.0218(11) 0.0294(12) 0.0199(10) -0.0061(9) 0.0062(9) -0.0034(9) N23 0.0173(10) 0.0273(11) 0.0207(10) -0.0058(8) 0.0039(8) 0.0032(8) N24 0.0180(11) 0.0281(12) 0.0211(10) -0.0053(9) 0.0030(9) 0.0007(8) C5 0.0159(11) 0.0248(12) 0.0177(11) 0.0024(9) 0.0053(9) -0.0002(9) O7 0.0244(10) 0.0452(11) 0.0243(10) -0.0056(8) 0.0040(8) -0.0022(8) O5 0.0226(10) 0.0376(10) 0.0298(10) -0.0032(8) 0.0073(8) 0.0022(7) O4 0.0349(11) 0.0513(12) 0.0240(10) -0.0114(9) 0.0125(9) -0.0210(9) O6 0.0227(9) 0.0372(10) 0.0228(9) -0.0001(7) 0.0075(8) 0.0034(7) 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 N5 1.251(2) . ? N1 C1 1.325(2) . ? N1 N2 1.346(2) . ? N2 N3 1.326(2) . ? N3 N4 1.345(2) . ? N4 C1 1.332(3) . ? N5 N6 1.283(2) . ? N5 C1 1.436(3) . ? N6 C2 1.383(3) . ? N7 C2 1.328(3) . ? N7 N8 1.352(2) . ? N8 N9 1.305(2) . ? N9 N10 1.343(2) . ? N10 C2 1.347(3) . ? N10 H10 0.92(3) . ? O2 N15 1.251(2) . ? N19 N18 1.305(2) . ? N19 N20 1.345(2) . ? N18 N17 1.347(2) . ? N17 C4 1.330(3) . ? N16 N15 1.284(2) . ? N16 C4 1.385(3) . ? N15 C3 1.437(2) . ? N11 C3 1.325(2) . ? N11 N12 1.345(2) . ? N12 N13 1.328(2) . ? N13 N14 1.347(2) . ? N14 C3 1.330(2) . ? N20 C4 1.343(3) . ? N20 H20 0.92(3) . ? O3 C5 1.219(2) . ? N21 C5 1.367(3) . ? N21 N22 1.420(2) . ? N21 H21 0.86(2) . ? N22 H22B 0.97(3) . ? N22 H22A 0.91(3) . ? N22 H22C 0.94(3) . ? N23 C5 1.364(3) . ? N23 N24 1.431(2) . ? N23 H23 0.88(2) . ? N24 H24B 0.96(3) . ? N24 H24A 0.97(3) . ? N24 H24C 0.99(3) . ? O7 H7A 0.86(3) . ? O7 H7B 0.83(3) . ? O5 H5A 0.87(3) . ? O5 H5B 0.84(3) . ? O4 H4B 0.83(3) . ? O4 H4A 0.85(3) . ? O6 H6B 0.80(3) . ? O6 H6A 0.93(4) . ? 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 C1 N1 N2 102.50(16) . . ? N3 N2 N1 109.75(16) . . ? N2 N3 N4 110.23(16) . . ? C1 N4 N3 102.09(17) . . ? O1 N5 N6 127.18(18) . . ? O1 N5 C1 117.10(17) . . ? N6 N5 C1 115.72(16) . . ? N5 N6 C2 115.79(17) . . ? C2 N7 N8 105.98(17) . . ? N9 N8 N7 110.68(17) . . ? N8 N9 N10 106.71(17) . . ? N9 N10 C2 108.25(18) . . ? N9 N10 H10 122.2(15) . . ? C2 N10 H10 129.4(15) . . ? N7 C2 N10 108.38(19) . . ? N7 C2 N6 119.62(18) . . ? N10 C2 N6 132.0(2) . . ? N1 C1 N4 115.43(19) . . ? N1 C1 N5 120.66(18) . . ? N4 C1 N5 123.91(18) . . ? N18 N19 N20 106.37(17) . . ? N19 N18 N17 111.28(17) . . ? C4 N17 N18 105.45(17) . . ? N15 N16 C4 115.23(16) . . ? O2 N15 N16 127.01(17) . . ? O2 N15 C3 117.35(16) . . ? N16 N15 C3 115.64(16) . . ? C3 N11 N12 102.52(16) . . ? N13 N12 N11 110.00(16) . . ? N12 N13 N14 109.73(16) . . ? C3 N14 N13 102.45(17) . . ? C4 N20 N19 108.09(18) . . ? C4 N20 H20 132.9(16) . . ? N19 N20 H20 118.6(16) . . ? N17 C4 N20 108.81(19) . . ? N17 C4 N16 120.10(18) . . ? N20 C4 N16 131.07(19) . . ? N11 C3 N14 115.30(18) . . ? N11 C3 N15 120.53(17) . . ? N14 C3 N15 124.15(18) . . ? C5 N21 N22 113.59(17) . . ? C5 N21 H21 119.4(15) . . ? N22 N21 H21 112.8(16) . . ? N21 N22 H22B 111.3(14) . . ? N21 N22 H22A 104.5(17) . . ? H22B N22 H22A 121(2) . . ? N21 N22 H22C 108.5(17) . . ? H22B N22 H22C 105(2) . . ? H22A N22 H22C 106(2) . . ? C5 N23 N24 113.58(17) . . ? C5 N23 H23 117.4(17) . . ? N24 N23 H23 116.5(16) . . ? N23 N24 H24B 106.5(14) . . ? N23 N24 H24A 110.6(14) . . ? H24B N24 H24A 112(2) . . ? N23 N24 H24C 108.0(15) . . ? H24B N24 H24C 112(2) . . ? H24A N24 H24C 107(2) . . ? O3 C5 N23 123.3(2) . . ? O3 C5 N21 122.69(19) . . ? N23 C5 N21 114.05(18) . . ? H7A O7 H7B 100(3) . . ? H5A O5 H5B 98(3) . . ? H4B O4 H4A 118(3) . . ? H6B O6 H6A 98(3) . . ? 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 C1 N1 N2 N3 -0.3(2) . . . . ? N1 N2 N3 N4 0.2(2) . . . . ? N2 N3 N4 C1 0.0(2) . . . . ? O1 N5 N6 C2 1.6(3) . . . . ? C1 N5 N6 C2 -178.72(17) . . . . ? C2 N7 N8 N9 0.1(2) . . . . ? N7 N8 N9 N10 -0.4(2) . . . . ? N8 N9 N10 C2 0.6(2) . . . . ? N8 N7 C2 N10 0.3(2) . . . . ? N8 N7 C2 N6 -178.28(18) . . . . ? N9 N10 C2 N7 -0.6(2) . . . . ? N9 N10 C2 N6 177.8(2) . . . . ? N5 N6 C2 N7 179.41(18) . . . . ? N5 N6 C2 N10 1.2(3) . . . . ? N2 N1 C1 N4 0.3(2) . . . . ? N2 N1 C1 N5 -179.02(17) . . . . ? N3 N4 C1 N1 -0.2(2) . . . . ? N3 N4 C1 N5 179.10(18) . . . . ? O1 N5 C1 N1 1.2(3) . . . . ? N6 N5 C1 N1 -178.52(18) . . . . ? O1 N5 C1 N4 -178.10(19) . . . . ? N6 N5 C1 N4 2.2(3) . . . . ? N20 N19 N18 N17 -0.1(2) . . . . ? N19 N18 N17 C4 -0.2(2) . . . . ? C4 N16 N15 O2 1.4(3) . . . . ? C4 N16 N15 C3 -178.73(16) . . . . ? C3 N11 N12 N13 0.2(2) . . . . ? N11 N12 N13 N14 -0.2(2) . . . . ? N12 N13 N14 C3 0.2(2) . . . . ? N18 N19 N20 C4 0.3(2) . . . . ? N18 N17 C4 N20 0.4(2) . . . . ? N18 N17 C4 N16 -178.25(18) . . . . ? N19 N20 C4 N17 -0.4(2) . . . . ? N19 N20 C4 N16 178.0(2) . . . . ? N15 N16 C4 N17 176.55(18) . . . . ? N15 N16 C4 N20 -1.7(3) . . . . ? N12 N11 C3 N14 -0.1(2) . . . . ? N12 N11 C3 N15 -178.77(16) . . . . ? N13 N14 C3 N11 -0.1(2) . . . . ? N13 N14 C3 N15 178.59(17) . . . . ? O2 N15 C3 N11 5.6(3) . . . . ? N16 N15 C3 N11 -174.31(18) . . . . ? O2 N15 C3 N14 -172.98(19) . . . . ? N16 N15 C3 N14 7.1(3) . . . . ? N24 N23 C5 O3 -14.9(3) . . . . ? N24 N23 C5 N21 164.84(18) . . . . ? N22 N21 C5 O3 -22.2(3) . . . . ? N22 N21 C5 N23 158.06(18) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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 N21 H21 O5 0.86(2) 2.36(2) 3.090(3) 142(2) . N21 H21 O4 0.86(2) 2.44(2) 3.010(3) 124.1(19) 2_655 N22 H22B N2 0.97(3) 1.96(3) 2.869(3) 156(2) 3_565 N10 H10 N13 0.92(3) 1.88(3) 2.782(3) 164(2) 3_665 N10 H10 N12 0.92(3) 2.70(3) 3.434(3) 137.3(19) 3_665 N24 H24A N1 0.97(3) 2.10(3) 3.061(3) 172(2) 4_576 O6 H6B N7 0.80(3) 2.04(3) 2.826(3) 165(3) 2_545 N24 H24C O5 0.99(3) 2.02(3) 2.944(3) 155(2) 1_565 O7 H7A N11 0.86(3) 2.22(3) 3.057(3) 162(2) 4_566 O7 H7A O2 0.86(3) 2.64(3) 3.094(2) 114(2) 4_566 N20 H20 N3 0.92(3) 1.90(3) 2.789(3) 162(2) 3_565 O5 H5A N17 0.87(3) 2.03(3) 2.882(3) 170(3) 2_645 N22 H22A O6 0.91(3) 1.93(3) 2.796(3) 159(2) . N22 H22C O6 0.94(3) 1.96(3) 2.878(3) 164(2) 2 O5 H5B N8 0.84(3) 2.20(3) 3.012(3) 164(3) 1_545 N23 H23 O4 0.88(2) 1.88(3) 2.712(3) 158(2) 2_655 O6 H6A O7 0.93(4) 1.86(4) 2.788(2) 174(3) . O4 H4B N12 0.83(3) 1.98(3) 2.782(3) 162(2) 3_655 O4 H4A N18 0.85(3) 2.02(3) 2.838(3) 162(3) 2_645 O4 H4A N19 0.85(3) 2.60(3) 3.231(3) 133(3) 2_645 O7 H7B N4 0.83(3) 2.31(4) 3.126(3) 168(3) 2_545 _geom_special_details ? _iucr_refine_instructions_details ; TITL v1 in P2(1)/c CELL 0.71073 13.0674 6.8891 24.3334 90.000 104.661 90.000 ZERR 4.00 0.0010 0.0007 0.0018 0.000 0.007 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C N O H UNIT 20 96 28 72 MERG 2 OMIT -2.00 51.50 FMAP 2 PLAN 20 SIZE 0.02 0.18 0.19 ACTA BOND $H CONF HTAB EQIV $1 -x+1, y+1/2, -z+1/2 EQIV $2 -x, -y+1, -z EQIV $3 -x+1, -y+1, -z EQIV $4 x, -y+3/2, z+1/2 EQIV $5 -x, y-1/2, -z+1/2 EQIV $6 x, y+1, z EQIV $7 x, -y+1/2, z+1/2 EQIV $8 -x+1, y-1/2, -z+1/2 EQIV $9 -x, y+1/2, -z+1/2 EQIV $10 x, y-1, z EQIV $11 -x+1, -y, -z HTAB N24 N1_$1 HTAB N21 O5 HTAB N21 O4_$1 HTAB N22 N2_$2 HTAB N10 N13_$3 HTAB N10 N12_$3 HTAB N24 N1_$4 HTAB O6 N7_$5 HTAB N24 O5_$6 HTAB O7 N11_$7 HTAB O7 O2_$7 HTAB N20 N3_$2 HTAB O5 N17_$8 HTAB N22 O6 HTAB N22 O6_$9 HTAB O5 N8_$10 HTAB N23 O4_$1 HTAB O6 O7 HTAB O4 N12_$11 HTAB O4 N18_$8 HTAB O4 N19_$8 HTAB O7 N4_$5 L.S. 5 TEMP -100.00 WGHT 0.031900 FVAR 0.30665 O1 3 0.181326 0.760170 -0.000514 11.00000 0.01621 0.06532 = 0.02893 -0.01309 0.00919 -0.00514 N1 2 0.017560 0.653467 -0.086001 11.00000 0.01867 0.03057 = 0.02156 -0.00279 0.00559 -0.00006 N2 2 -0.081983 0.618807 -0.116558 11.00000 0.01796 0.03276 = 0.02351 -0.00350 0.00504 0.00022 N3 2 -0.149277 0.653973 -0.085104 11.00000 0.02059 0.03128 = 0.02102 -0.00292 0.00695 -0.00061 N4 2 -0.096727 0.713449 -0.032922 11.00000 0.01710 0.03264 = 0.02005 -0.00129 0.00559 -0.00149 N5 2 0.091826 0.765260 0.009175 11.00000 0.01631 0.02830 = 0.02233 -0.00085 0.00840 0.00012 N6 2 0.069724 0.813685 0.055768 11.00000 0.02078 0.03010 = 0.01814 -0.00285 0.00738 -0.00397 N7 2 0.138399 0.924663 0.148822 11.00000 0.02448 0.03423 = 0.01977 -0.00457 0.00769 -0.00369 N8 2 0.234202 0.976636 0.181720 11.00000 0.02554 0.03549 = 0.02351 -0.00466 0.00786 -0.00588 N9 2 0.307064 0.956261 0.154063 11.00000 0.02593 0.03580 = 0.02198 -0.00329 0.00716 -0.00328 N10 2 0.258461 0.888534 0.102295 11.00000 0.01919 0.02896 = 0.02054 -0.00330 0.00592 -0.00301 C2 1 0.154567 0.870598 0.099332 11.00000 0.02054 0.02185 = 0.02213 -0.00001 0.00834 -0.00340 C1 1 0.003324 0.710152 -0.036414 11.00000 0.01602 0.02262 = 0.01599 -0.00126 0.00387 -0.00075 O2 3 0.345127 0.275696 0.046486 11.00000 0.01331 0.04741 = 0.02742 -0.00844 0.00797 -0.00748 N19 2 0.353159 0.498750 0.194839 11.00000 0.02719 0.04050 = 0.02446 -0.00614 0.01010 -0.00175 N18 2 0.447835 0.562929 0.219013 11.00000 0.02794 0.04203 = 0.02387 -0.00539 0.00976 -0.00191 N17 2 0.513793 0.539140 0.185029 11.00000 0.02325 0.03766 = 0.02040 -0.00621 0.00697 -0.00270 N16 2 0.501660 0.406313 0.094539 11.00000 0.01910 0.02741 = 0.01770 -0.00344 0.00466 -0.00285 N15 2 0.440474 0.317661 0.052384 11.00000 0.01773 0.02452 = 0.01746 0.00038 0.00594 -0.00048 N11 2 0.429649 0.184510 -0.039997 11.00000 0.02126 0.02701 = 0.01999 -0.00348 0.00771 -0.00255 N12 2 0.501516 0.149984 -0.069783 11.00000 0.01863 0.03017 = 0.02149 -0.00248 0.00697 -0.00055 N13 2 0.596821 0.205518 -0.040061 11.00000 0.02016 0.02839 = 0.02006 -0.00273 0.00626 -0.00100 N14 2 0.590388 0.279076 0.010240 11.00000 0.01834 0.02362 = 0.01893 -0.00081 0.00709 0.00103 N20 2 0.357002 0.431098 0.143543 11.00000 0.02051 0.03125 = 0.01773 -0.00346 0.00704 -0.00083 C4 1 0.455899 0.455818 0.138095 11.00000 0.01864 0.02423 = 0.01860 0.00112 0.00602 0.00035 C3 1 0.487863 0.262025 0.007533 11.00000 0.01828 0.01888 = 0.01756 -0.00056 0.00749 0.00002 O3 3 0.082175 0.776243 0.300875 11.00000 0.02084 0.03691 = 0.02534 -0.00845 -0.00144 0.00961 N21 2 0.188596 0.563540 0.270366 11.00000 0.01563 0.02990 = 0.02091 -0.00745 0.00207 0.00106 N22 2 0.096995 0.484598 0.232562 11.00000 0.02179 0.02935 = 0.01991 -0.00606 0.00620 -0.00337 N23 2 0.247078 0.715283 0.356375 11.00000 0.01730 0.02730 = 0.02067 -0.00579 0.00389 0.00321 N24 2 0.234963 0.882245 0.389134 11.00000 0.01805 0.02814 = 0.02108 -0.00529 0.00297 0.00071 C5 1 0.166501 0.691262 0.308782 11.00000 0.01588 0.02484 = 0.01771 0.00236 0.00529 -0.00024 O7 3 0.190392 0.251486 0.427237 11.00000 0.02442 0.04515 = 0.02430 -0.00556 0.00400 -0.00218 O5 3 0.267135 0.143756 0.299272 11.00000 0.02263 0.03763 = 0.02981 -0.00316 0.00729 0.00223 O4 3 0.580057 0.058847 0.169062 11.00000 0.03488 0.05133 = 0.02404 -0.01139 0.01251 -0.02098 O6 3 0.044659 0.286835 0.322017 11.00000 0.02274 0.03717 = 0.02279 -0.00009 0.00753 0.00342 H24B 4 0.290237 0.876028 0.423357 11.00000 0.03821 H21 4 0.238162 0.478593 0.281622 11.00000 0.03194 H22B 4 0.112134 0.440307 0.197696 11.00000 0.04131 H10 4 0.295265 0.854513 0.076006 11.00000 0.04606 H24A 4 0.165187 0.884035 0.396337 11.00000 0.04443 H6B 4 -0.000769 0.343944 0.332153 11.00000 0.04797 H24C 4 0.240963 0.999003 0.366588 11.00000 0.05535 H7A 4 0.254369 0.295060 0.438460 11.00000 0.05758 H20 4 0.294799 0.391531 0.118592 11.00000 0.05703 H5A 4 0.334734 0.127824 0.304825 11.00000 0.06240 H22A 4 0.069505 0.402750 0.254486 11.00000 0.05731 H22C 4 0.046876 0.584995 0.221227 11.00000 0.06190 H5B 4 0.247592 0.086987 0.268035 11.00000 0.06933 H23 4 0.311552 0.689844 0.353643 11.00000 0.04255 H6A 4 0.095451 0.283562 0.356617 11.00000 0.09235 H4B 4 0.546669 -0.013988 0.143616 11.00000 0.05032 H4A 4 0.558542 0.070445 0.199014 11.00000 0.07710 H7B 4 0.173333 0.250874 0.457888 11.00000 0.07840 HKLF 4 REM v1 in P2(1)/c REM R1 = 0.0409 for 2898 Fo > 4sig(Fo) and 0.0659 for all 4026 data REM 397 parameters refined using 0 restraints END WGHT 0.0320 0.0000 REM Highest difference peak 0.225, deepest hole -0.251, 1-sigma level 0.050 Q1 1 0.4701 0.2782 0.0283 11.00000 0.05 0.22 Q2 1 0.0441 0.8350 0.2622 11.00000 0.05 0.22 Q3 1 0.5444 0.1959 0.0180 11.00000 0.05 0.22 Q4 1 0.4686 0.1350 -0.0030 11.00000 0.05 0.20 Q5 1 0.0694 0.0751 0.3219 11.00000 0.05 0.20 Q6 1 0.6665 0.1575 -0.0407 11.00000 0.05 0.20 Q7 1 0.1933 0.5919 -0.0174 11.00000 0.05 0.19 Q8 1 0.2691 0.7736 0.3208 11.00000 0.05 0.19 Q9 1 0.4045 0.4935 0.1367 11.00000 0.05 0.19 Q10 1 0.4606 0.6478 0.2540 11.00000 0.05 0.19 Q11 1 0.3087 0.5627 0.2161 11.00000 0.05 0.19 Q12 1 0.0471 1.0080 0.1442 11.00000 0.05 0.19 Q13 1 -0.1242 0.5209 -0.1527 11.00000 0.05 0.18 Q14 1 0.1665 0.8104 -0.0536 11.00000 0.05 0.18 Q15 1 0.5646 0.4502 0.0999 11.00000 0.05 0.18 Q16 1 0.1459 0.4616 0.3075 11.00000 0.05 0.18 Q17 1 0.0842 0.6821 -0.0892 11.00000 0.05 0.18 Q18 1 0.0000 0.5000 0.0000 10.50000 0.05 0.17 Q19 1 0.0704 0.3895 0.1599 11.00000 0.05 0.17 Q20 1 0.0931 0.9148 0.3287 11.00000 0.05 0.17 ;