# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # 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_gx072 _database_code_depnum_ccdc_archive 'CCDC 872230' _audit_author_name 'Joerg Stierstorfer' _audit_block_code ? _audit_creation_method SHELXL-97 _audit_creation_date ; 'Fri Feb 04 13:32:21 2011' ; _audit_update_record 31.05.2011 _chemical_name_systematic 'Bishydroxylammonium 5,5-1N-oxidotetrazolate' _chemical_compound_source ? _chemical_name_common 'TKX50, Thomas Klapoetke 50 Year Explosive' _chemical_formula_moiety ? _chemical_formula_sum 'C2 H8 N10 O4' _chemical_formula_weight 236.18 _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 2267 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.71 _diffrn_reflns_theta_max 27.10 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 901 _reflns_number_gt 681 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0852335229 _diffrn_orient_matrix_UB_12 -0.0453875875 _diffrn_orient_matrix_UB_13 0.0236661505 _diffrn_orient_matrix_UB_21 -0.0877202534 _diffrn_orient_matrix_UB_22 -0.0276081755 _diffrn_orient_matrix_UB_23 0.0577245972 _diffrn_orient_matrix_UB_31 -0.0484751169 _diffrn_orient_matrix_UB_32 -0.0296744428 _diffrn_orient_matrix_UB_33 -0.0901024448 _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 5.4260(5) _cell_length_b 11.6597(12) _cell_length_c 6.5013(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.256(9) _cell_angle_gamma 90.00 _cell_volume 409.58(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1010 _cell_measurement_theta_min 4.6714 _cell_measurement_theta_max 33.5758 _cell_special_details ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.915 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.173 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96476 _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 0.230 _refine_diff_density_min -0.186 _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 901 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0856 _refine_ls_wR_factor_gt 0.0825 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _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 O2 O 1.1089(2) 0.28881(10) 1.10799(17) 0.0216(3) Uani 1 1 d . . . O1 O 0.7317(2) 0.08647(10) 0.68294(17) 0.0216(3) Uani 1 1 d . . . N5 N 1.2641(3) 0.35222(13) 0.9882(2) 0.0155(3) Uani 1 1 d . . . N1 N 0.7378(2) 0.08596(11) 0.8859(2) 0.0155(3) Uani 1 1 d . . . N4 N 0.8289(3) 0.05686(12) 1.2133(2) 0.0182(3) Uani 1 1 d . . . N2 N 0.5669(2) 0.14111(12) 0.9857(2) 0.0189(3) Uani 1 1 d . . . N3 N 0.6243(3) 0.12291(12) 1.1824(2) 0.0209(3) Uani 1 1 d . . . C1 C 0.8961(3) 0.03419(12) 1.0256(2) 0.0141(4) Uani 1 1 d . . . H5A H 1.198(4) 0.417(2) 0.940(3) 0.029(5) Uiso 1 1 d . . . H5B H 1.306(4) 0.310(2) 0.886(3) 0.035(6) Uiso 1 1 d . . . H5C H 1.408(4) 0.3664(18) 1.067(3) 0.036(6) Uiso 1 1 d . . . H2 H 0.986(5) 0.338(2) 1.130(3) 0.058(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0196(7) 0.0213(7) 0.0256(7) 0.0052(5) 0.0111(5) -0.0001(5) O1 0.0228(7) 0.0272(7) 0.0149(6) 0.0012(5) 0.0017(4) 0.0018(5) N5 0.0159(8) 0.0154(8) 0.0156(8) 0.0015(6) 0.0037(6) 0.0006(6) N1 0.0147(7) 0.0152(7) 0.0166(7) -0.0001(5) 0.0013(5) -0.0008(5) N4 0.0164(7) 0.0170(7) 0.0217(8) -0.0019(5) 0.0041(5) -0.0001(6) N2 0.0151(8) 0.0173(7) 0.0249(8) -0.0011(6) 0.0055(6) 0.0005(6) N3 0.0202(8) 0.0194(7) 0.0236(8) -0.0012(6) 0.0052(5) 0.0014(6) C1 0.0136(8) 0.0141(8) 0.0143(8) -0.0007(6) 0.0001(6) -0.0030(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 O2 N5 1.4081(17) . ? O2 H2 0.90(3) . ? O1 N1 1.3166(16) . ? N5 H5A 0.88(2) . ? N5 H5B 0.87(2) . ? N5 H5C 0.91(2) . ? N1 C1 1.3360(19) . ? N1 N2 1.3430(19) . ? N4 C1 1.332(2) . ? N4 N3 1.3509(19) . ? N2 N3 1.306(2) . ? C1 C1 1.444(3) 3_757 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 O2 H2 104.1(15) . . ? O2 N5 H5A 113.5(13) . . ? O2 N5 H5B 109.8(14) . . ? H5A N5 H5B 109.5(19) . . ? O2 N5 H5C 108.1(13) . . ? H5A N5 H5C 110.4(18) . . ? H5B N5 H5C 105.2(19) . . ? O1 N1 C1 129.70(13) . . ? O1 N1 N2 121.80(13) . . ? C1 N1 N2 108.50(13) . . ? C1 N4 N3 105.49(12) . . ? N3 N2 N1 106.40(13) . . ? N2 N3 N4 110.94(13) . . ? N4 C1 N1 108.67(14) . . ? N4 C1 C1 127.28(17) . 3_757 ? N1 C1 C1 124.05(18) . 3_757 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 N1 N2 N3 179.43(13) . . . . ? C1 N1 N2 N3 0.41(16) . . . . ? N1 N2 N3 N4 -0.08(17) . . . . ? C1 N4 N3 N2 -0.27(17) . . . . ? N3 N4 C1 N1 0.53(16) . . . . ? N3 N4 C1 C1 -179.57(19) . . . 3_757 ? O1 N1 C1 N4 -179.51(14) . . . . ? N2 N1 C1 N4 -0.59(16) . . . . ? O1 N1 C1 C1 0.6(3) . . . 3_757 ? N2 N1 C1 C1 179.50(18) . . . 3_757 ? 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 N5 H5A O1 0.88(2) 2.18(2) 2.9499(19) 145.7(17) 2_756 N5 H5A N4 0.88(2) 2.39(2) 3.020(2) 128.4(16) 4_565 N5 H5B O2 0.87(2) 2.32(2) 3.023(2) 137.8(19) 4_565 N5 H5B N3 0.87(2) 2.40(2) 2.927(2) 119.3(18) 4_665 N5 H5B N2 0.87(2) 2.48(2) 2.960(2) 115.2(16) 1_655 N5 H5C O1 0.91(2) 1.93(2) 2.8219(19) 167.9(19) 4_666 N5 H5C N1 0.91(2) 2.67(2) 3.549(2) 162.7(17) 4_666 O2 H2 O1 0.90(3) 1.70(3) 2.5933(17) 172(2) 4_566 O2 H2 N1 0.90(3) 2.41(2) 3.1810(18) 144.5(19) 4_566 _geom_special_details ? _iucr_refine_instructions_details ; TITL gx072 in P2(1)/c CELL 0.71073 5.4260 11.6597 6.5013 90.000 95.256 90.000 ZERR 2.00 0.0005 0.0012 0.0007 0.000 0.009 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 4 16 20 8 MERG 2 OMIT -2.00 54.20 FMAP 2 PLAN 15 HTAB EQIV $1 -x+2, y+1/2, -z+3/2 EQIV $2 x, -y+1/2, z-1/2 EQIV $3 x+1, -y+1/2, z-1/2 EQIV $4 x+1, y, z EQIV $5 x+1, -y+1/2, z+1/2 EQIV $6 x, -y+1/2, z+1/2 HTAB N5 O1_$1 HTAB N5 N4_$2 HTAB N5 O2_$2 HTAB N5 N3_$3 HTAB N5 N2_$4 HTAB N5 O1_$5 HTAB N5 N1_$5 HTAB O2 O1_$6 HTAB O2 N1_$6 ACTA BOND $H CONF L.S. 4 TEMP -100.00 WGHT 0.049200 FVAR 12.01817 O2 4 1.108948 0.288811 1.107987 11.00000 0.01963 0.02126 = 0.02559 0.00522 0.01108 -0.00011 O1 4 0.731699 0.086467 0.682945 11.00000 0.02280 0.02720 = 0.01489 0.00122 0.00175 0.00181 N5 3 1.264112 0.352225 0.988151 11.00000 0.01589 0.01543 = 0.01561 0.00152 0.00370 0.00058 N1 3 0.737758 0.085958 0.885856 11.00000 0.01472 0.01523 = 0.01661 -0.00014 0.00131 -0.00075 N4 3 0.828878 0.056862 1.213309 11.00000 0.01637 0.01701 = 0.02168 -0.00192 0.00411 -0.00010 N2 3 0.566941 0.141110 0.985659 11.00000 0.01511 0.01732 = 0.02488 -0.00113 0.00548 0.00051 N3 3 0.624290 0.122906 1.182366 11.00000 0.02020 0.01940 = 0.02363 -0.00120 0.00524 0.00145 C1 1 0.896126 0.034186 1.025574 11.00000 0.01364 0.01414 = 0.01428 -0.00067 0.00014 -0.00303 H5A 2 1.197526 0.416759 0.940096 11.00000 0.02881 H5B 2 1.305661 0.310410 0.885612 11.00000 0.03517 H5C 2 1.408240 0.366355 1.066809 11.00000 0.03613 H2 2 0.986200 0.337609 1.129684 11.00000 0.05759 HKLF 4 REM gx072 in P2(1)/c REM R1 = 0.0334 for 681 Fo > 4sig(Fo) and 0.0471 for all 901 data REM 89 parameters refined using 0 restraints END WGHT 0.0492 0.0000 REM Highest difference peak 0.230, deepest hole -0.186, 1-sigma level 0.050 Q1 1 0.3993 0.1758 0.8795 11.00000 0.05 0.23 Q2 1 0.7930 0.0269 0.9527 11.00000 0.05 0.21 Q3 1 0.8929 0.0767 0.9643 11.00000 0.05 0.20 Q4 1 0.8460 0.0420 1.3559 11.00000 0.05 0.20 Q5 1 0.7665 0.0944 1.2123 11.00000 0.05 0.17 Q6 1 0.6309 0.1143 0.9311 11.00000 0.05 0.16 Q7 1 1.0237 0.0157 1.0113 11.00000 0.05 0.16 Q8 1 0.6015 0.0364 0.5831 11.00000 0.05 0.15 Q9 1 0.9938 0.2701 1.0246 11.00000 0.05 0.15 Q10 1 0.5421 0.1414 0.8199 11.00000 0.05 0.14 Q11 1 1.0488 0.3011 1.1320 11.00000 0.05 0.14 Q12 1 1.1650 0.2932 1.2799 11.00000 0.05 0.14 Q13 1 0.9480 0.0863 1.2444 11.00000 0.05 0.13 Q14 1 0.7086 0.1653 0.7094 11.00000 0.05 0.12 Q15 1 0.7210 -0.0185 0.6919 11.00000 0.05 0.12 ; data_hx089 _database_code_depnum_ccdc_archive 'CCDC 872231' _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 ; 'Thu Feb 16 15:32:13 2012' ; _audit_update_record 17.02.2012 _chemical_name_systematic 'bishydroxylammonium 5,5-bis(1-oxidotetrazolate' _chemical_compound_source ? _chemical_name_common TKX-50 _chemical_formula_moiety 'C2 N8 O2, 2(H4 N O) ' _chemical_formula_sum 'C2 H8 N10 O4' _chemical_formula_weight 236.18 _cell_length_a 5.4872(8) _cell_length_b 11.5472(15) _cell_length_c 6.4833(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.402(12) _cell_angle_gamma 90.00 _cell_volume 408.97(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 748 _cell_measurement_theta_min 4.6465 _cell_measurement_theta_max 32.1327 _cell_special_details ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.918 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.173 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9340 _exptl_absorpt_correction_T_max 0.9580 _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 100 # 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 1773 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.74 _diffrn_reflns_theta_max 27.24 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.24 _diffrn_measured_fraction_theta_full 0.990 _reflns_number_total 910 _reflns_number_gt 769 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0800914000 _diffrn_orient_matrix_UB_12 0.0479521000 _diffrn_orient_matrix_UB_13 0.0164764000 _diffrn_orient_matrix_UB_21 -0.1011442000 _diffrn_orient_matrix_UB_22 0.0383986000 _diffrn_orient_matrix_UB_23 -0.0154267000 _diffrn_orient_matrix_UB_31 -0.0141838000 _diffrn_orient_matrix_UB_32 -0.0019025000 _diffrn_orient_matrix_UB_33 0.1075368000 _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 -P2ybc 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 0.241 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.058 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0461P)^2^+0.0918P] 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 910 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0895 _refine_ls_wR_factor_gt 0.0818 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 0.26487(18) 0.08833(9) 0.32005(15) 0.0121(3) Uani 1 1 d . . . N1 N 0.2619(2) 0.08656(11) 0.11501(18) 0.0096(3) Uani 1 1 d . . . N2 N 0.4330(2) 0.14060(11) 0.01537(18) 0.0121(3) Uani 1 1 d . . . N3 N 0.3762(2) 0.12097(11) -0.18278(18) 0.0129(3) Uani 1 1 d . . . N4 N 0.1725(2) 0.05509(11) -0.21436(18) 0.0123(3) Uani 1 1 d . . . C1 C 0.1037(3) 0.03379(12) -0.0258(2) 0.0101(3) Uani 1 1 d . . . O2 O 0.8853(2) 0.21165(10) 0.39123(15) 0.0131(3) Uani 1 1 d . . . N5 N 0.7326(2) 0.14768(12) 0.51361(19) 0.0102(3) Uani 1 1 d . . . H5B H 0.802(4) 0.0786(19) 0.550(3) 0.021(5) Uiso 1 1 d . . . H5A H 0.582(4) 0.1345(18) 0.440(3) 0.026(5) Uiso 1 1 d . . . H5C H 0.709(4) 0.1885(18) 0.627(3) 0.018(5) Uiso 1 1 d . . . H2 H 1.004(5) 0.163(2) 0.376(4) 0.057(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0116(5) 0.0162(6) 0.0086(5) -0.0008(4) 0.0006(4) -0.0006(4) N1 0.0082(6) 0.0102(6) 0.0104(6) -0.0006(4) 0.0006(4) 0.0001(5) N2 0.0093(6) 0.0110(6) 0.0163(6) 0.0014(5) 0.0036(5) -0.0006(5) N3 0.0119(6) 0.0124(6) 0.0146(6) 0.0001(5) 0.0021(4) -0.0011(5) N4 0.0103(6) 0.0119(6) 0.0151(6) 0.0012(5) 0.0032(4) 0.0005(5) C1 0.0084(7) 0.0093(7) 0.0123(7) 0.0001(5) 0.0002(5) 0.0016(6) O2 0.0118(5) 0.0127(6) 0.0157(5) 0.0034(4) 0.0058(4) 0.0002(4) N5 0.0101(6) 0.0109(7) 0.0100(6) 0.0012(5) 0.0028(4) -0.0001(5) 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 N1 1.3280(15) . ? N1 N2 1.3424(17) . ? N1 C1 1.3451(18) . ? N2 N3 1.3128(17) . ? N3 N4 1.3513(18) . ? N4 C1 1.3358(19) . ? C1 C1 1.445(3) 3 ? O2 N5 1.4152(15) . ? O2 H2 0.87(3) . ? N5 H5B 0.91(2) . ? N5 H5A 0.93(2) . ? N5 H5C 0.89(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 N1 N2 122.09(11) . . ? O1 N1 C1 129.25(12) . . ? N2 N1 C1 108.65(12) . . ? N3 N2 N1 106.16(12) . . ? N2 N3 N4 111.24(11) . . ? C1 N4 N3 105.43(11) . . ? N4 C1 N1 108.52(13) . . ? N4 C1 C1 127.46(16) . 3 ? N1 C1 C1 124.02(16) . 3 ? N5 O2 H2 102.6(17) . . ? O2 N5 H5B 110.5(12) . . ? O2 N5 H5A 110.0(12) . . ? H5B N5 H5A 108.8(18) . . ? O2 N5 H5C 108.9(12) . . ? H5B N5 H5C 109.9(17) . . ? H5A N5 H5C 108.6(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 O1 N1 N2 N3 179.67(12) . . . . ? C1 N1 N2 N3 0.47(15) . . . . ? N1 N2 N3 N4 -0.20(15) . . . . ? N2 N3 N4 C1 -0.14(16) . . . . ? N3 N4 C1 N1 0.43(15) . . . . ? N3 N4 C1 C1 -179.57(18) . . . 3 ? O1 N1 C1 N4 -179.70(12) . . . . ? N2 N1 C1 N4 -0.57(16) . . . . ? O1 N1 C1 C1 0.3(3) . . . 3 ? N2 N1 C1 C1 179.43(17) . . . 3 ? 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 N5 H5B O1 0.91(2) 2.15(2) 2.9305(17) 144.1(16) 3_656 N5 H5B N4 0.91(2) 2.44(2) 3.0464(18) 124.5(16) 1_656 N5 H5A O1 0.93(2) 1.91(2) 2.8327(17) 170.8(18) . N5 H5A N1 0.93(2) 2.67(2) 3.5481(18) 158.1(15) . N5 H5C O2 0.89(2) 2.21(2) 2.9913(18) 145.9(17) 4_566 N5 H5C N3 0.89(2) 2.429(19) 2.9187(17) 115.0(15) 1_556 O2 H2 O1 0.87(3) 1.74(3) 2.6000(16) 169(3) 1_655 O2 H2 N1 0.87(3) 2.47(3) 3.2032(16) 142(2) 1_655 _geom_special_details ? _iucr_refine_instructions_details ; TITL v1 in P2(1)/c CELL 0.71073 5.4872 11.5472 6.4833 90.000 95.402 90.000 ZERR 2.00 0.0008 0.0015 0.0009 0.000 0.012 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C N O H UNIT 4 20 8 16 MERG 2 OMIT -2.00 54.50 OMIT 0 1 3 OMIT -3 6 1 OMIT -1 0 8 OMIT 2 1 7 OMIT 2 3 0 EQIV $1 -x+1, -y, -z+1 EQIV $2 x+1, y, z+1 EQIV $3 x, -y+1/2, z+1/2 EQIV $4 x, y, z+1 EQIV $5 x+1, y, z HTAB N5 O1_$1 HTAB N5 N4_$2 HTAB N5 O1 HTAB N5 N1 HTAB N5 O2_$3 HTAB N5 N3_$4 HTAB O2 O1_$5 HTAB O2 N1_$5 FMAP 2 PLAN 20 SIZE 0.25 0.30 0.40 ACTA BOND $H CONF L.S. 5 TEMP -173.00 WGHT 0.046100 0.091800 FVAR 0.37701 O1 3 0.264875 0.088329 0.320048 11.00000 0.01155 0.01621 = 0.00856 -0.00082 0.00060 -0.00058 N1 2 0.261911 0.086561 0.115012 11.00000 0.00817 0.01023 = 0.01036 -0.00063 0.00063 0.00009 N2 2 0.432979 0.140604 0.015373 11.00000 0.00933 0.01098 = 0.01631 0.00141 0.00361 -0.00060 N3 2 0.376172 0.120973 -0.182780 11.00000 0.01190 0.01243 = 0.01458 0.00010 0.00205 -0.00112 N4 2 0.172543 0.055091 -0.214356 11.00000 0.01029 0.01187 = 0.01506 0.00120 0.00319 0.00047 C1 1 0.103691 0.033794 -0.025820 11.00000 0.00844 0.00929 = 0.01228 0.00012 0.00020 0.00157 O2 3 0.885307 0.211655 0.391229 11.00000 0.01176 0.01273 = 0.01568 0.00335 0.00585 0.00022 N5 2 0.732560 0.147685 0.513608 11.00000 0.01010 0.01091 = 0.00997 0.00124 0.00279 -0.00007 H5B 4 0.801778 0.078585 0.550148 11.00000 0.02113 H5A 4 0.581561 0.134526 0.439769 11.00000 0.02602 H5C 4 0.709208 0.188485 0.626515 11.00000 0.01793 H2 4 1.003613 0.163421 0.375676 11.00000 0.05666 HKLF 4 REM v1 in P2(1)/c REM R1 = 0.0342 for 769 Fo > 4sig(Fo) and 0.0427 for all 910 data REM 89 parameters refined using 0 restraints END WGHT 0.0463 0.0912 REM Highest difference peak 0.241, deepest hole -0.311, 1-sigma level 0.058 Q1 1 0.1915 0.0400 0.0533 11.00000 0.05 0.24 Q2 1 0.0000 0.0000 0.0000 10.50000 0.05 0.23 Q3 1 0.5216 0.1231 -0.2233 11.00000 0.05 0.21 Q4 1 0.3837 0.1186 0.0629 11.00000 0.05 0.20 Q5 1 0.9526 0.0171 0.5587 11.00000 0.05 0.19 Q6 1 0.4072 0.1260 -0.0911 11.00000 0.05 0.18 Q7 1 0.4200 0.2026 0.0214 11.00000 0.05 0.18 Q8 1 0.3610 0.1346 0.4409 11.00000 0.05 0.17 Q9 1 0.2801 0.1749 0.2884 11.00000 0.05 0.17 Q10 1 0.1976 0.0042 -0.3492 11.00000 0.05 0.17 Q11 1 0.8204 0.2178 0.2841 11.00000 0.05 0.17 Q12 1 0.5746 0.1815 0.0841 11.00000 0.05 0.16 Q13 1 0.7873 -0.0177 0.5548 11.00000 0.05 0.16 Q14 1 0.4284 0.1408 0.1984 11.00000 0.05 0.16 Q15 1 0.2316 0.1756 0.4265 11.00000 0.05 0.16 Q16 1 0.9589 0.2543 0.5013 11.00000 0.05 0.15 Q17 1 0.3973 0.1766 -0.2541 11.00000 0.05 0.15 Q18 1 0.1351 -0.0162 -0.3011 11.00000 0.05 0.15 Q19 1 0.5179 0.2262 0.1453 11.00000 0.05 0.15 Q20 1 0.2448 0.0071 0.3298 11.00000 0.05 0.14 ; data_hx089_2 _database_code_depnum_ccdc_archive 'CCDC 872232' _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 ; 'Thu Feb 16 13:31:57 2012' ; _audit_update_record 16.02.2012 _chemical_name_systematic 'bishydroxylammonium bis-1N-oxidotetrazolate' _chemical_compound_source ? _chemical_name_common ' bishydroxylammonium bis-1N-oxidotetrazolate' _chemical_formula_moiety ? _chemical_formula_sum 'C2 H8 N10 O4' _chemical_formula_weight 236.18 _cell_length_a 5.4408(6) _cell_length_b 11.7514(13) _cell_length_c 6.5612(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.071(11) _cell_angle_gamma 90.00 _cell_volume 417.86(9) _cell_formula_units_Z 2 _cell_measurement_temperature 298 _cell_measurement_reflns_used 591 _cell_measurement_theta_min 4.1325 _cell_measurement_theta_max 32.2092 _cell_special_details ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.877 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.169 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9353 _exptl_absorpt_correction_T_max 0.9833 _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 298 _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 1798 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.66 _diffrn_reflns_theta_max 26.99 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.993 _reflns_number_total 911 _reflns_number_gt 729 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0856469000 _diffrn_orient_matrix_UB_12 -0.0426779000 _diffrn_orient_matrix_UB_13 -0.0228091000 _diffrn_orient_matrix_UB_21 0.0969899000 _diffrn_orient_matrix_UB_22 0.0404453000 _diffrn_orient_matrix_UB_23 0.0120308000 _diffrn_orient_matrix_UB_31 0.0193773000 _diffrn_orient_matrix_UB_32 -0.0136924000 _diffrn_orient_matrix_UB_33 0.1054354000 _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 -P2ybc 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 0.233 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.049 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0516P)^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 911 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0915 _refine_ls_wR_factor_gt 0.0835 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.73270(19) 0.41409(9) 0.18469(15) 0.0261(3) Uani 1 1 d . . . N1 N 0.7377(2) 0.41412(10) 0.38692(19) 0.0199(3) Uani 1 1 d . . . N2 N 0.5682(2) 0.35888(11) 0.4862(2) 0.0258(3) Uani 1 1 d . . . N3 N 0.6258(3) 0.37644(11) 0.6816(2) 0.0280(3) Uani 1 1 d . . . N4 N 0.8301(2) 0.44280(11) 0.7121(2) 0.0247(3) Uani 1 1 d . . . C1 C 0.8965(3) 0.46551(12) 0.5252(2) 0.0190(3) Uani 1 1 d . . . O2 O 0.1096(2) 0.28904(10) 0.10684(18) 0.0309(3) Uani 1 1 d . . . N5 N 0.2648(3) 0.35214(13) -0.0117(2) 0.0219(3) Uani 1 1 d . . . H5A H 0.193(4) 0.4188(19) -0.058(3) 0.042(6) Uiso 1 1 d . . . H2 H -0.016(5) 0.3383(19) 0.121(3) 0.059(7) Uiso 1 1 d . . . H5C H 0.305(5) 0.310(2) -0.111(4) 0.060(7) Uiso 1 1 d . . . H5B H 0.405(4) 0.3701(19) 0.062(3) 0.055(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0267(6) 0.0332(6) 0.0183(6) -0.0027(5) 0.0011(4) -0.0034(5) N1 0.0183(6) 0.0197(6) 0.0219(7) -0.0004(5) 0.0026(5) -0.0008(5) N2 0.0211(7) 0.0246(7) 0.0325(8) 0.0003(6) 0.0074(5) -0.0049(5) N3 0.0286(8) 0.0283(7) 0.0279(7) 0.0009(6) 0.0070(6) -0.0051(6) N4 0.0246(7) 0.0263(6) 0.0236(7) 0.0034(6) 0.0053(5) -0.0024(6) C1 0.0178(7) 0.0199(7) 0.0194(7) 0.0009(6) 0.0020(5) 0.0009(6) O2 0.0269(6) 0.0295(6) 0.0384(7) 0.0071(5) 0.0150(5) 0.0023(5) N5 0.0213(7) 0.0233(7) 0.0215(7) 0.0019(6) 0.0038(5) -0.0003(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 N1 1.3247(16) . ? N1 C1 1.3400(18) . ? N1 N2 1.3428(18) . ? N2 N3 1.309(2) . ? N3 N4 1.3579(19) . ? N4 C1 1.336(2) . ? C1 C1 1.449(3) 3_766 ? O2 N5 1.4087(17) . ? O2 H2 0.91(2) . ? N5 H5A 0.92(2) . ? N5 H5C 0.86(3) . ? N5 H5B 0.89(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 N1 C1 129.28(13) . . ? O1 N1 N2 122.10(12) . . ? C1 N1 N2 108.61(13) . . ? N3 N2 N1 106.45(12) . . ? N2 N3 N4 110.93(13) . . ? C1 N4 N3 105.30(12) . . ? N4 C1 N1 108.71(13) . . ? N4 C1 C1 126.86(16) . 3_766 ? N1 C1 C1 124.42(17) . 3_766 ? N5 O2 H2 102.5(14) . . ? O2 N5 H5A 112.1(12) . . ? O2 N5 H5C 108.6(16) . . ? H5A N5 H5C 112(2) . . ? O2 N5 H5B 110.5(14) . . ? H5A N5 H5B 107.3(19) . . ? H5C N5 H5B 107(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 O1 N1 N2 N3 -179.75(12) . . . . ? C1 N1 N2 N3 -0.40(16) . . . . ? N1 N2 N3 N4 0.27(17) . . . . ? N2 N3 N4 C1 -0.04(17) . . . . ? N3 N4 C1 N1 -0.21(16) . . . . ? N3 N4 C1 C1 179.38(17) . . . 3_766 ? O1 N1 C1 N4 179.67(13) . . . . ? N2 N1 C1 N4 0.38(16) . . . . ? O1 N1 C1 C1 0.1(3) . . . 3_766 ? N2 N1 C1 C1 -179.22(17) . . . 3_766 ? 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 N5 H5A O1 0.92(2) 2.18(2) 2.9729(18) 144.0(16) 3_665 N5 H5A N4 0.92(2) 2.39(2) 3.0423(19) 127.9(16) 1_454 O2 H2 O1 0.91(2) 1.71(3) 2.6097(16) 169(2) 1_455 O2 H2 N1 0.91(2) 2.46(2) 3.2075(18) 140.1(18) 1_455 N5 H5C O2 0.86(3) 2.36(3) 3.059(2) 139(2) 4_565 N5 H5C N3 0.86(3) 2.44(2) 2.9477(19) 119(2) 1_554 N5 H5C N2 0.86(3) 2.50(3) 2.979(2) 116.2(19) 4_565 N5 H5B O1 0.89(2) 1.96(3) 2.8445(18) 171(2) . _geom_special_details ? _iucr_refine_instructions_details ; TITL v1 in P2(1)/c CELL 0.71073 5.4408 11.7514 6.5612 90.000 95.071 90.000 ZERR 2.00 0.0006 0.0013 0.0009 0.000 0.011 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C N O H UNIT 4 20 8 16 MERG 2 OMIT -2.00 54.00 OMIT 1 2 7 OMIT 0 1 3 OMIT 1 1 0 EQIV $1 -x+1, -y+1, -z EQIV $2 x-1, y, z-1 EQIV $3 x-1, y, z EQIV $4 x, -y+1/2, z-1/2 EQIV $5 x, y, z-1 HTAB N5 O1_$1 HTAB N5 N4_$2 HTAB O2 O1_$3 HTAB O2 N1_$3 HTAB N5 O2_$4 HTAB N5 N3_$5 HTAB N5 N2_$4 HTAB N5 O1 FMAP 2 PLAN 20 SIZE 0.10 0.25 0.40 ACTA BOND $H CONF L.S. 10 TEMP 298.00 WGHT 0.051600 FVAR 1.23651 O1 3 0.732698 0.414089 0.184693 11.00000 0.02673 0.03316 = 0.01826 -0.00268 0.00111 -0.00343 N1 2 0.737737 0.414115 0.386916 11.00000 0.01831 0.01974 = 0.02190 -0.00045 0.00264 -0.00082 N2 2 0.568153 0.358881 0.486187 11.00000 0.02107 0.02463 = 0.03247 0.00027 0.00743 -0.00493 N3 2 0.625845 0.376445 0.681566 11.00000 0.02862 0.02830 = 0.02788 0.00089 0.00700 -0.00509 N4 2 0.830121 0.442795 0.712060 11.00000 0.02463 0.02632 = 0.02362 0.00344 0.00533 -0.00241 C1 1 0.896545 0.465512 0.525172 11.00000 0.01777 0.01992 = 0.01937 0.00089 0.00202 0.00089 O2 3 0.109589 0.289038 0.106840 11.00000 0.02686 0.02949 = 0.03840 0.00709 0.01502 0.00227 N5 2 0.264818 0.352138 -0.011716 11.00000 0.02127 0.02329 = 0.02150 0.00193 0.00376 -0.00029 H5A 4 0.193081 0.418837 -0.058400 11.00000 0.04190 H2 4 -0.016493 0.338311 0.121011 11.00000 0.05894 H5C 4 0.304951 0.309897 -0.111023 11.00000 0.06001 H5B 4 0.404870 0.370058 0.062035 11.00000 0.05533 HKLF 4 REM v1 in P2(1)/c REM R1 = 0.0344 for 729 Fo > 4sig(Fo) and 0.0469 for all 911 data REM 89 parameters refined using 0 restraints END WGHT 0.0516 0.0000 REM Highest difference peak 0.233, deepest hole -0.224, 1-sigma level 0.049 Q1 1 1.0000 0.5000 0.5000 10.50000 0.05 0.23 Q2 1 0.8601 0.4460 0.8484 11.00000 0.05 0.20 Q3 1 0.8158 0.4662 0.4416 11.00000 0.05 0.19 Q4 1 0.2141 0.3424 -0.2099 11.00000 0.05 0.15 Q5 1 -0.2419 0.2574 0.1010 11.00000 0.05 0.14 Q6 1 0.2237 0.1411 0.1215 11.00000 0.05 0.14 Q7 1 0.4362 0.4084 0.7251 11.00000 0.05 0.14 Q8 1 0.7218 0.3353 0.2178 11.00000 0.05 0.14 Q9 1 0.8457 0.4758 0.5747 11.00000 0.05 0.14 Q10 1 0.4421 0.3136 0.3878 11.00000 0.05 0.14 Q11 1 0.5425 0.2854 0.4727 11.00000 0.05 0.14 Q12 1 0.7619 0.4137 0.7020 11.00000 0.05 0.14 Q13 1 0.5543 0.3555 0.3380 11.00000 0.05 0.13 Q14 1 0.3930 0.4193 0.3746 11.00000 0.05 0.13 Q15 1 0.7933 0.5846 0.7441 11.00000 0.05 0.13 Q16 1 1.1246 0.4001 0.6340 11.00000 0.05 0.13 Q17 1 0.6330 0.3796 0.4377 11.00000 0.05 0.13 Q18 1 0.0151 0.3152 0.1365 11.00000 0.05 0.12 Q19 1 0.2644 0.2527 -0.2626 11.00000 0.05 0.12 Q20 1 0.0806 0.2766 0.2768 11.00000 0.05 0.12 ; data_gx320 _database_code_depnum_ccdc_archive 'CCDC 884559' #TrackingRef 'gx320_1BTO_2MeOH.cif' _vrf_PLAT780_gx320 ; RESPONSE: The atoms are placed correctly. Alert must be caused by the long hydrogen bond. ; _vrf_PLAT042_gx320 ; RESPONSE: The reported moiety formula is the correct one ; _vrf_PLAT045_gx320 ; RESPONSE: The reported Z is the correct one ; _vrf_PLAT303_gx320 ; RESPONSE: Alert is caused by the elongated OH distance due to the strong hydrogen bond. This short distance is found in most BTO structures. ; _audit_author_name 'Joerg Stierstorfer' _audit_block_code ? _audit_creation_method SHELXL-97 _audit_creation_date ; 'Thu May 26 23:52:59 2011' ; _audit_update_record 30.05.2011 _chemical_name_systematic '5,5-bis(1-hydroxy-tetrazole) dimethanolate' _chemical_compound_source ? _chemical_name_common '5,5-bis(1-hydroxy-tetrazole) dimethanolate' _chemical_formula_moiety 'C2 H2 N8 O2, 2(C H4 O)' _chemical_formula_sum 'C4 H10 N8 O4' _chemical_formula_weight 234.20 _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 4803 _diffrn_reflns_av_R_equivalents 0.0678 _diffrn_reflns_av_sigmaI/netI 0.0705 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.16 _diffrn_reflns_theta_max 25.99 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 968 _reflns_number_gt 555 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.0720624875 _diffrn_orient_matrix_UB_12 0.0604957715 _diffrn_orient_matrix_UB_13 0.0119501115 _diffrn_orient_matrix_UB_21 0.0243713148 _diffrn_orient_matrix_UB_22 -0.0200182066 _diffrn_orient_matrix_UB_23 0.0356519630 _diffrn_orient_matrix_UB_31 0.0725655716 _diffrn_orient_matrix_UB_32 0.0669855519 _diffrn_orient_matrix_UB_33 -0.0000773298 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P bca' _symmetry_Int_Tables_number 61 _symmetry_space_group_name_Hall ' -P 2ac 2ab' 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+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 7.6818(10) _cell_length_b 6.7692(12) _cell_length_c 18.884(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 982.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 851 _cell_measurement_theta_min 4.1362 _cell_measurement_theta_max 35.1422 _cell_special_details ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.88533 _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 0.293 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.056 _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 968 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0767 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.0891 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 0.841 _refine_ls_restrained_S_all 0.841 _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 1.3201(2) -0.0535(3) 0.54328(8) 0.0238(4) Uani 1 1 d . . . O2 O 0.9524(3) -0.3800(2) 0.60968(9) 0.0224(4) Uani 1 1 d . . . N4 N 0.8981(3) 0.0838(3) 0.58394(10) 0.0210(5) Uani 1 1 d . . . N1 N 1.1664(2) 0.0056(3) 0.57053(10) 0.0201(5) Uani 1 1 d . . . N3 N 0.9835(2) 0.1017(3) 0.64603(10) 0.0251(5) Uani 1 1 d . . . N2 N 1.1475(2) 0.0536(3) 0.63859(10) 0.0247(5) Uani 1 1 d . . . C1 C 1.0142(3) 0.0211(3) 0.53687(11) 0.0187(6) Uani 1 1 d . . . C2 C 0.9440(4) -0.3964(5) 0.68620(13) 0.0268(6) Uani 1 1 d . . . H1 H 1.421(4) 0.018(4) 0.5729(13) 0.043(8) Uiso 1 1 d . . . H2B H 0.903(4) -0.525(5) 0.7004(14) 0.046(9) Uiso 1 1 d . . . H20 H 0.855(5) -0.377(5) 0.5898(16) 0.059(11) Uiso 1 1 d . . . H2C H 0.863(4) -0.297(4) 0.7062(14) 0.048(9) Uiso 1 1 d . . . H2A H 1.059(5) -0.368(5) 0.7079(16) 0.067(10) 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 0.0122(9) 0.0346(10) 0.0245(10) -0.0055(8) 0.0010(7) 0.0043(8) O2 0.0159(10) 0.0294(10) 0.0217(9) -0.0004(8) -0.0002(8) 0.0012(8) N4 0.0179(11) 0.0263(11) 0.0190(10) -0.0010(10) 0.0012(8) 0.0001(9) N1 0.0148(11) 0.0242(11) 0.0214(11) -0.0011(9) 0.0011(9) -0.0009(8) N3 0.0153(11) 0.0343(13) 0.0258(11) -0.0045(10) -0.0003(9) -0.0012(9) N2 0.0188(11) 0.0337(13) 0.0215(11) -0.0023(10) 0.0011(10) -0.0007(9) C1 0.0163(13) 0.0181(13) 0.0218(12) 0.0014(11) -0.0003(11) -0.0014(10) C2 0.0257(16) 0.0349(18) 0.0198(13) -0.0046(14) -0.0009(12) 0.0004(14) 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 N1 1.349(2) . ? O1 H1 1.07(3) . ? O2 C2 1.451(3) . ? O2 H20 0.84(4) . ? N4 C1 1.329(3) . ? N4 N3 1.349(3) . ? N1 N2 1.334(2) . ? N1 C1 1.334(3) . ? N3 N2 1.309(3) . ? C1 C1 1.438(4) 5_756 ? C2 H2B 0.96(3) . ? C2 H2C 0.99(3) . ? C2 H2A 0.99(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 N1 O1 H1 107.5(14) . . ? C2 O2 H20 114(2) . . ? C1 N4 N3 106.46(19) . . ? N2 N1 C1 110.15(19) . . ? N2 N1 O1 122.35(17) . . ? C1 N1 O1 127.48(18) . . ? N2 N3 N4 110.64(18) . . ? N3 N2 N1 105.60(17) . . ? N4 C1 N1 107.14(19) . . ? N4 C1 C1 127.5(3) . 5_756 ? N1 C1 C1 125.4(3) . 5_756 ? O2 C2 H2B 111.2(16) . . ? O2 C2 H2C 110.8(15) . . ? H2B C2 H2C 108(2) . . ? O2 C2 H2A 110.8(18) . . ? H2B C2 H2A 110(2) . . ? H2C C2 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 N4 N3 N2 0.4(3) . . . . ? N4 N3 N2 N1 0.4(3) . . . . ? C1 N1 N2 N3 -1.0(2) . . . . ? O1 N1 N2 N3 -179.63(19) . . . . ? N3 N4 C1 N1 -1.0(2) . . . . ? N3 N4 C1 C1 179.7(3) . . . 5_756 ? N2 N1 C1 N4 1.3(2) . . . . ? O1 N1 C1 N4 179.8(2) . . . . ? N2 N1 C1 C1 -179.4(3) . . . 5_756 ? O1 N1 C1 C1 -0.8(4) . . . 5_756 ? 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 O1 H1 O2 1.07(3) 1.38(3) 2.451(2) 177(2) 7_865 O2 H20 N4 0.84(4) 1.97(4) 2.747(3) 155(3) 7_755 O2 H20 O1 0.84(4) 2.57(3) 3.095(2) 122(3) 3_446 _geom_special_details ? _iucr_refine_instructions_details ; TITL gx320 in Pbca CELL 0.71073 7.6818 6.7692 18.8838 90.000 90.000 90.000 ZERR 4.00 0.0010 0.0012 0.0027 0.000 0.000 0.000 LATT 1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 16 40 32 16 MERG 2 OMIT -2.00 52.00 FMAP 2 PLAN 25 ACTA BOND $H CONF HTAB EQIV $1 -x+5/2, y+1/2, z EQIV $2 -x+3/2, y-1/2, z EQIV $3 x-1/2, -y-1/2, -z+1 HTAB O1 O2_$1 HTAB O2 N4_$2 HTAB O2 O1_$3 L.S. 4 TEMP -100.00 WGHT 0.041800 FVAR 4.87887 O1 4 1.320098 -0.053520 0.543282 11.00000 0.01224 0.03462 = 0.02447 -0.00553 0.00101 0.00432 O2 4 0.952389 -0.379994 0.609678 11.00000 0.01592 0.02943 = 0.02171 -0.00043 -0.00015 0.00122 N4 3 0.898060 0.083798 0.583938 11.00000 0.01786 0.02626 = 0.01901 -0.00102 0.00120 0.00013 N1 3 1.166360 0.005555 0.570529 11.00000 0.01481 0.02424 = 0.02137 -0.00114 0.00105 -0.00094 N3 3 0.983487 0.101698 0.646034 11.00000 0.01534 0.03432 = 0.02575 -0.00449 -0.00030 -0.00119 N2 3 1.147474 0.053568 0.638590 11.00000 0.01880 0.03369 = 0.02152 -0.00234 0.00107 -0.00074 C1 1 1.014228 0.021079 0.536873 11.00000 0.01629 0.01810 = 0.02183 0.00142 -0.00031 -0.00136 C2 1 0.943987 -0.396353 0.686198 11.00000 0.02571 0.03491 = 0.01976 -0.00456 -0.00090 0.00037 H1 2 1.421250 0.018179 0.572868 11.00000 0.04336 H2B 2 0.903159 -0.524938 0.700419 11.00000 0.04631 H20 2 0.855339 -0.376924 0.589779 11.00000 0.05913 H2C 2 0.863488 -0.296862 0.706168 11.00000 0.04828 H2A 2 1.059317 -0.368330 0.707869 11.00000 0.06741 HKLF 4 REM gx320 in Pbca REM R1 = 0.0404 for 555 Fo > 4sig(Fo) and 0.0767 for all 968 data REM 93 parameters refined using 0 restraints END WGHT 0.0418 0.0000 REM Highest difference peak 0.293, deepest hole -0.219, 1-sigma level 0.056 Q1 1 1.1694 -0.2233 0.5518 11.00000 0.05 0.29 Q2 1 0.9443 0.1756 0.6843 11.00000 0.05 0.25 Q3 1 0.9413 0.1904 0.6109 11.00000 0.05 0.25 Q4 1 1.1627 -0.2553 0.6359 11.00000 0.05 0.22 Q5 1 0.9256 -0.2834 0.5838 11.00000 0.05 0.20 Q6 1 0.8197 -0.4117 0.7113 11.00000 0.05 0.19 Q7 1 0.9625 -0.3124 0.6446 11.00000 0.05 0.19 Q8 1 1.3171 -0.2097 0.5531 11.00000 0.05 0.19 Q9 1 1.1679 0.1984 0.5707 11.00000 0.05 0.18 Q10 1 1.4713 0.2526 0.5313 11.00000 0.05 0.17 Q11 1 1.0373 -0.2234 0.5985 11.00000 0.05 0.17 Q12 1 0.9554 0.3110 0.6111 11.00000 0.05 0.16 Q13 1 0.8992 0.0372 0.6119 11.00000 0.05 0.15 Q14 1 0.9630 -0.2697 0.7064 11.00000 0.05 0.15 Q15 1 0.9937 0.1965 0.5402 11.00000 0.05 0.15 Q16 1 0.8920 -0.6981 0.6995 11.00000 0.05 0.15 Q17 1 0.7846 0.1163 0.6001 11.00000 0.05 0.14 Q18 1 1.2419 -0.1581 0.5794 11.00000 0.05 0.14 Q19 1 1.0507 -0.4735 0.7040 11.00000 0.05 0.14 Q20 1 1.1248 0.1854 0.6305 11.00000 0.05 0.14 Q21 1 0.9756 0.0532 0.7099 11.00000 0.05 0.12 Q22 1 1.2323 0.0600 0.6638 11.00000 0.05 0.12 Q23 1 1.0537 -0.3076 0.6952 11.00000 0.05 0.12 Q24 1 1.1117 -0.1898 0.6685 11.00000 0.05 0.12 Q25 1 0.9217 -0.0920 0.7212 11.00000 0.05 0.11 ; data_gx563_Me2NH2_1BTO _database_code_depnum_ccdc_archive 'CCDC 884560' #TrackingRef 'gx563_Me2NH2_1BTO.cif' _vrf_PLAT303_gx320 ; RESPONSE: Alert is caused by the elongated OH distance due to the strong hydrogen bond. This short distance is found in most BTO structures. ; _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 Oct 05 14:09:39 2011' ; _audit_update_record ? _chemical_name_systematic 'dimethylammonium 5-(1-hydroxytetrazolyl)-5-(1-oxidotetrazolate' _chemical_compound_source ? _chemical_name_common 'dimethylammonium 5-(1-hydroxytetrazolyl)-5-(1-oxidotetrazolate' _chemical_formula_moiety 'C2 H N8 O2, C2 H8 N ' _chemical_formula_sum 'C4 H9 N9 O2' _chemical_formula_weight 215.20 _cell_length_a 11.660(2) _cell_length_b 8.7050(17) _cell_length_c 18.028(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1829.8(6) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1508 _cell_measurement_theta_min 4.1131 _cell_measurement_theta_max 33.5921 _cell_special_details ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.84718 _exptl_absorpt_correction_T_max 0.99999 _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 8586 _diffrn_reflns_av_R_equivalents 0.0625 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.16 _diffrn_reflns_theta_max 25.75 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.75 _diffrn_measured_fraction_theta_full 0.993 _reflns_number_total 1741 _reflns_number_gt 1244 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0060932000 _diffrn_orient_matrix_UB_12 -0.0477377000 _diffrn_orient_matrix_UB_13 0.0316979000 _diffrn_orient_matrix_UB_21 0.0085199000 _diffrn_orient_matrix_UB_22 0.0657278000 _diffrn_orient_matrix_UB_23 0.0224875000 _diffrn_orient_matrix_UB_31 -0.0599423000 _diffrn_orient_matrix_UB_32 0.0042120000 _diffrn_orient_matrix_UB_33 0.0065216000 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P bca' _symmetry_Int_Tables_number 61 _symmetry_space_group_name_Hall '-P 2ac 2ab ' 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+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, 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 0.241 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.054 _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 SHELXL _refine_ls_extinction_coef 0.0049(11) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1741 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0706 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1201 _refine_ls_wR_factor_gt 0.0993 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 O2 O 0.65519(12) 0.49528(18) 0.50166(8) 0.0309(4) Uani 1 1 d . . . O1 O 1.07081(12) 0.26035(17) 0.50745(8) 0.0278(4) Uani 1 1 d . . . N9 N 1.10595(17) 0.2716(2) 0.66289(10) 0.0270(5) Uani 1 1 d . . . N7 N 0.83722(16) 0.5055(2) 0.64838(10) 0.0313(5) Uani 1 1 d . . . N2 N 0.98990(16) 0.2174(2) 0.39085(10) 0.0298(5) Uani 1 1 d . . . N1 N 0.98385(14) 0.2732(2) 0.45986(9) 0.0221(4) Uani 1 1 d . . . N3 N 0.89137(16) 0.2499(2) 0.35966(10) 0.0335(5) Uani 1 1 d . . . N8 N 0.90615(15) 0.4275(2) 0.60047(9) 0.0266(5) Uani 1 1 d . . . N5 N 0.74374(14) 0.47896(19) 0.54894(10) 0.0246(4) Uani 1 1 d . . . N4 N 0.82233(16) 0.3263(2) 0.40713(10) 0.0306(5) Uani 1 1 d . . . N6 N 0.73900(16) 0.5370(2) 0.61785(11) 0.0328(5) Uani 1 1 d . . . C2 C 0.84638(17) 0.4134(2) 0.53796(11) 0.0220(5) Uani 1 1 d . . . C4 C 1.0365(2) 0.1379(3) 0.68490(16) 0.0368(6) Uani 1 1 d . . . C1 C 0.88179(17) 0.3394(2) 0.46997(11) 0.0220(5) Uani 1 1 d . . . C3 C 1.1530(2) 0.3573(3) 0.72695(15) 0.0373(6) Uani 1 1 d . . . H1 H 0.615(3) 0.384(4) 0.5024(16) 0.092(11) Uiso 1 1 d . . . H3B H 1.092(2) 0.388(3) 0.7569(14) 0.056(8) Uiso 1 1 d . . . H3A H 1.208(3) 0.286(3) 0.7542(15) 0.062(9) Uiso 1 1 d . . . H9B H 1.166(2) 0.239(3) 0.6332(14) 0.050(8) Uiso 1 1 d . . . H9A H 1.056(2) 0.330(3) 0.6342(13) 0.045(7) Uiso 1 1 d . . . H4B H 1.082(2) 0.071(3) 0.7118(15) 0.060(9) Uiso 1 1 d . . . H4A H 0.968(2) 0.184(3) 0.7142(15) 0.056(8) Uiso 1 1 d . . . H3C H 1.198(2) 0.443(3) 0.7085(15) 0.053(8) Uiso 1 1 d . . . H4C H 1.004(2) 0.085(3) 0.6411(15) 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 O2 0.0217(8) 0.0290(9) 0.0420(10) 0.0048(7) -0.0062(7) 0.0022(7) O1 0.0221(8) 0.0330(9) 0.0282(9) -0.0047(7) -0.0063(7) 0.0028(7) N9 0.0261(11) 0.0334(11) 0.0214(11) 0.0030(8) -0.0020(9) 0.0007(9) N7 0.0291(11) 0.0342(11) 0.0307(11) -0.0065(8) 0.0038(9) -0.0005(9) N2 0.0308(11) 0.0347(12) 0.0240(10) -0.0042(8) 0.0035(9) -0.0022(8) N1 0.0204(9) 0.0228(10) 0.0231(10) 0.0005(7) -0.0013(8) -0.0009(7) N3 0.0327(11) 0.0432(12) 0.0246(10) -0.0056(9) -0.0025(9) 0.0021(9) N8 0.0285(10) 0.0272(10) 0.0240(10) -0.0014(8) 0.0001(8) -0.0012(8) N5 0.0192(9) 0.0241(10) 0.0306(10) -0.0005(8) -0.0031(8) -0.0011(7) N4 0.0310(11) 0.0352(11) 0.0258(10) -0.0023(8) -0.0013(8) 0.0015(9) N6 0.0303(11) 0.0330(11) 0.0351(12) -0.0068(8) 0.0034(9) -0.0015(9) C2 0.0204(11) 0.0191(11) 0.0266(12) 0.0018(9) -0.0006(9) -0.0021(9) C4 0.0368(15) 0.0328(15) 0.0409(16) 0.0025(12) -0.0024(13) -0.0069(12) C1 0.0202(11) 0.0219(11) 0.0238(12) 0.0029(9) -0.0018(9) -0.0008(9) C3 0.0388(15) 0.0413(16) 0.0320(14) -0.0067(12) -0.0009(13) -0.0029(13) 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 O2 N5 1.346(2) . ? O2 H1 1.07(4) . ? O1 N1 1.333(2) . ? N9 C4 1.472(3) . ? N9 C3 1.480(3) . ? N9 H9B 0.92(3) . ? N9 H9A 0.93(3) . ? N7 N6 1.300(3) . ? N7 N8 1.361(2) . ? N2 N3 1.310(2) . ? N2 N1 1.337(2) . ? N1 C1 1.335(3) . ? N3 N4 1.350(2) . ? N8 C2 1.331(3) . ? N5 C2 1.340(3) . ? N5 N6 1.342(3) . ? N4 C1 1.333(3) . ? C2 C1 1.445(3) . ? C4 H4B 0.92(3) . ? C4 H4A 1.04(3) . ? C4 H4C 0.99(3) . ? C3 H3B 0.93(3) . ? C3 H3A 1.02(3) . ? C3 H3C 0.97(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 N5 O2 H1 103.5(16) . . ? C4 N9 C3 113.1(2) . . ? C4 N9 H9B 109.2(16) . . ? C3 N9 H9B 109.1(16) . . ? C4 N9 H9A 104.1(15) . . ? C3 N9 H9A 112.8(15) . . ? H9B N9 H9A 108(2) . . ? N6 N7 N8 110.90(17) . . ? N3 N2 N1 105.94(17) . . ? O1 N1 C1 128.80(17) . . ? O1 N1 N2 121.88(16) . . ? C1 N1 N2 109.32(17) . . ? N2 N3 N4 110.93(17) . . ? C2 N8 N7 105.91(17) . . ? C2 N5 N6 109.49(17) . . ? C2 N5 O2 129.49(18) . . ? N6 N5 O2 120.98(17) . . ? C1 N4 N3 105.71(17) . . ? N7 N6 N5 106.03(17) . . ? N8 C2 N5 107.65(18) . . ? N8 C2 C1 127.59(19) . . ? N5 C2 C1 124.76(19) . . ? N9 C4 H4B 109.1(18) . . ? N9 C4 H4A 104.6(14) . . ? H4B C4 H4A 114(2) . . ? N9 C4 H4C 111.2(14) . . ? H4B C4 H4C 110(2) . . ? H4A C4 H4C 107(2) . . ? N4 C1 N1 108.10(18) . . ? N4 C1 C2 127.63(19) . . ? N1 C1 C2 124.27(18) . . ? N9 C3 H3B 108.5(16) . . ? N9 C3 H3A 107.6(16) . . ? H3B C3 H3A 112(2) . . ? N9 C3 H3C 108.6(15) . . ? H3B C3 H3C 113(2) . . ? H3A C3 H3C 107(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 N3 N2 N1 O1 -179.78(17) . . . . ? N3 N2 N1 C1 -0.2(2) . . . . ? N1 N2 N3 N4 0.4(2) . . . . ? N6 N7 N8 C2 0.7(2) . . . . ? N2 N3 N4 C1 -0.5(2) . . . . ? N8 N7 N6 N5 -0.1(2) . . . . ? C2 N5 N6 N7 -0.6(2) . . . . ? O2 N5 N6 N7 -178.58(17) . . . . ? N7 N8 C2 N5 -1.1(2) . . . . ? N7 N8 C2 C1 179.94(19) . . . . ? N6 N5 C2 N8 1.1(2) . . . . ? O2 N5 C2 N8 178.80(18) . . . . ? N6 N5 C2 C1 -179.89(18) . . . . ? O2 N5 C2 C1 -2.2(3) . . . . ? N3 N4 C1 N1 0.4(2) . . . . ? N3 N4 C1 C2 179.4(2) . . . . ? O1 N1 C1 N4 179.45(18) . . . . ? N2 N1 C1 N4 -0.1(2) . . . . ? O1 N1 C1 C2 0.4(3) . . . . ? N2 N1 C1 C2 -179.23(19) . . . . ? N8 C2 C1 N4 -179.4(2) . . . . ? N5 C2 C1 N4 1.8(3) . . . . ? N8 C2 C1 N1 -0.5(3) . . . . ? N5 C2 C1 N1 -179.34(19) . . . . ? 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 H1 O1 1.07(4) 1.37(4) 2.439(2) 171(3) 3_456 O2 H1 N1 1.07(4) 2.16(3) 3.152(2) 152(2) 3_456 O2 H1 N2 1.07(4) 2.57(3) 3.301(2) 125(2) 3_456 N9 H9B N4 0.92(3) 2.04(3) 2.947(3) 165(2) 3_556 N9 H9B N3 0.92(3) 2.63(3) 3.358(3) 136(2) 3_556 N9 H9A N8 0.93(3) 2.04(3) 2.922(3) 158(2) . N9 H9A O1 0.93(3) 2.37(2) 2.834(2) 110.6(18) . _geom_special_details ? _iucr_refine_instructions_details ; TITL v1 in Pbca CELL 0.71073 11.6598 8.7050 18.0278 90.000 90.000 90.000 ZERR 8.00 0.0021 0.0017 0.0032 0.000 0.000 0.000 LATT 1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 32 72 72 16 MERG 2 OMIT -2.00 51.50 OMIT 4 4 18 OMIT 4 1 5 OMIT 1 2 14 OMIT 12 3 7 OMIT 4 2 16 OMIT 8 1 11 OMIT 8 1 15 OMIT 8 7 8 EQIV $1 x-1/2, -y+1/2, -z+1 EQIV $2 x+1/2, -y+1/2, -z+1 HTAB O2 O1_$1 HTAB O2 N1_$1 HTAB O2 N2_$1 HTAB N9 N4_$2 HTAB N9 N3_$2 HTAB N9 N8 HTAB N9 O1 FMAP 2 PLAN 25 ACTA BOND $H CONF L.S. 4 TEMP -100.00 WGHT 0.045400 EXTI 0.004875 FVAR 4.40367 O2 4 0.655195 0.495278 0.501656 11.00000 0.02173 0.02896 = 0.04204 0.00482 -0.00623 0.00221 O1 4 1.070812 0.260351 0.507450 11.00000 0.02211 0.03302 = 0.02823 -0.00465 -0.00634 0.00277 N9 3 1.105949 0.271579 0.662894 11.00000 0.02612 0.03340 = 0.02144 0.00295 -0.00204 0.00073 N7 3 0.837217 0.505523 0.648378 11.00000 0.02915 0.03417 = 0.03071 -0.00645 0.00377 -0.00052 N2 3 0.989903 0.217419 0.390849 11.00000 0.03075 0.03472 = 0.02396 -0.00415 0.00354 -0.00221 N1 3 0.983854 0.273202 0.459860 11.00000 0.02036 0.02283 = 0.02307 0.00046 -0.00132 -0.00089 N3 3 0.891369 0.249882 0.359665 11.00000 0.03273 0.04319 = 0.02461 -0.00557 -0.00246 0.00214 N8 3 0.906149 0.427547 0.600472 11.00000 0.02851 0.02718 = 0.02401 -0.00137 0.00010 -0.00119 N5 3 0.743740 0.478960 0.548939 11.00000 0.01915 0.02411 = 0.03056 -0.00054 -0.00311 -0.00110 N4 3 0.822334 0.326327 0.407125 11.00000 0.03097 0.03518 = 0.02580 -0.00232 -0.00132 0.00153 N6 3 0.739003 0.537023 0.617850 11.00000 0.03027 0.03301 = 0.03510 -0.00676 0.00344 -0.00150 C2 1 0.846375 0.413406 0.537960 11.00000 0.02041 0.01914 = 0.02657 0.00182 -0.00064 -0.00208 C4 1 1.036510 0.137867 0.684896 11.00000 0.03678 0.03277 = 0.04093 0.00247 -0.00240 -0.00694 C1 1 0.881786 0.339430 0.469968 11.00000 0.02022 0.02194 = 0.02378 0.00293 -0.00179 -0.00079 C3 1 1.152978 0.357297 0.726946 11.00000 0.03878 0.04127 = 0.03195 -0.00674 -0.00088 -0.00286 H1 2 0.614721 0.384424 0.502428 11.00000 0.09174 H3B 2 1.092400 0.387884 0.756939 11.00000 0.05594 H3A 2 1.207705 0.286183 0.754185 11.00000 0.06184 H9B 2 1.165826 0.239032 0.633174 11.00000 0.04971 H9A 2 1.056491 0.330212 0.634217 11.00000 0.04461 H4B 2 1.081578 0.071023 0.711783 11.00000 0.05982 H4A 2 0.968359 0.184157 0.714206 11.00000 0.05646 H3C 2 1.197918 0.442565 0.708529 11.00000 0.05346 H4C 2 1.003624 0.085498 0.641053 11.00000 0.04492 HKLF 4 REM v1 in Pbca REM R1 = 0.0437 for 1244 Fo > 4sig(Fo) and 0.0706 for all 1741 data REM 173 parameters refined using 0 restraints END WGHT 0.0457 0.0000 REM Highest difference peak 0.241, deepest hole -0.200, 1-sigma level 0.054 Q1 1 1.0055 0.2551 0.5424 11.00000 0.05 0.24 Q2 1 0.7395 0.3415 0.4036 11.00000 0.05 0.19 Q3 1 1.0981 0.3628 0.5611 11.00000 0.05 0.18 Q4 1 0.7587 0.2844 0.4092 11.00000 0.05 0.18 Q5 1 0.6746 0.4693 0.6536 11.00000 0.05 0.18 Q6 1 1.0707 0.1679 0.3853 11.00000 0.05 0.17 Q7 1 0.8380 0.1413 0.4051 11.00000 0.05 0.17 Q8 1 0.9472 0.1607 0.5451 11.00000 0.05 0.17 Q9 1 0.9124 0.2581 0.4883 11.00000 0.05 0.17 Q10 1 1.1303 0.3295 0.7828 11.00000 0.05 0.16 Q11 1 0.7184 0.4747 0.3794 11.00000 0.05 0.16 Q12 1 0.6789 0.6247 0.5578 11.00000 0.05 0.16 Q13 1 0.6347 0.6103 0.4690 11.00000 0.05 0.15 Q14 1 0.9874 0.4388 0.6035 11.00000 0.05 0.15 Q15 1 0.8330 0.3005 0.3876 11.00000 0.05 0.15 Q16 1 1.0827 0.2579 0.5769 11.00000 0.05 0.15 Q17 1 0.6646 0.2705 0.5492 11.00000 0.05 0.15 Q18 1 0.6403 0.5591 0.6451 11.00000 0.05 0.15 Q19 1 0.8784 0.4758 0.6286 11.00000 0.05 0.15 Q20 1 0.8892 0.4070 0.5869 11.00000 0.05 0.15 Q21 1 0.9765 0.1401 0.6639 11.00000 0.05 0.15 Q22 1 1.1135 0.0124 0.6406 11.00000 0.05 0.15 Q23 1 0.9044 0.0872 0.5946 11.00000 0.05 0.15 Q24 1 1.3214 0.4322 0.6518 11.00000 0.05 0.15 Q25 1 1.0489 -0.0189 0.5893 11.00000 0.05 0.15 ; data_on281 _database_code_depnum_ccdc_archive 'CCDC 884561' _audit_author_name 'Peter Mayer' _audit_block_code ? _audit_creation_method SHELXL-97 _audit_creation_date 05-Nov-10 _audit_update_record ? _chemical_name_systematic '5,5-bis(1-hydroxy-tetrazole) dihydrate' _chemical_compound_source ? _chemical_name_common '5,5-bis(1-hydroxy-tetrazole) dihydrate' _chemical_formula_moiety 'C2 H2 N8 O2, 2(H2 O)' _chemical_formula_sum 'C2 H6 N8 O4' _chemical_formula_weight 206.15 _diffrn_ambient_temperature 173(2) _diffrn_source_type ? _diffrn_source_power 3.025 _diffrn_source_voltage 55.00 _diffrn_source_current 55.00 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation 0.5 _diffrn_measurement_device '95mm 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 9 _diffrn_reflns_number 1625 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.39 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _reflns_number_total 472 _reflns_number_gt 460 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.0272645 _diffrn_orient_matrix_UB_12 0.0176734 _diffrn_orient_matrix_UB_13 -0.1227987 _diffrn_orient_matrix_UB_21 0.0904896 _diffrn_orient_matrix_UB_22 0.1242680 _diffrn_orient_matrix_UB_23 0.0313995 _diffrn_orient_matrix_UB_31 0.1082897 _diffrn_orient_matrix_UB_32 -0.0993918 _diffrn_orient_matrix_UB_33 0.0174228 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M ' C 2/m' _symmetry_Int_Tables_number 12 _symmetry_space_group_name_Hall '-C 2y' 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, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 7.7443(3) _cell_length_b 6.2459(3) _cell_length_c 8.7000(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.052(2) _cell_angle_gamma 90.00 _cell_volume 378.06(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 839 _cell_measurement_theta_min 3.134 _cell_measurement_theta_max 27.485 _cell_special_details ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.811 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 0.166 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 6 1 0.027000 0 -5 -1 0.033000 6 -6 -1 0.083000 -5 -4 -1 0.105000 2 0 -3 0.068000 -3 0 4 0.101000 1 0 16 0.058000 0 0 -1 0.039000 _diffrn_special_details ? _refine_diff_density_max 0.465 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.071 _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.14(4) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 472 _refine_ls_number_parameters 53 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1431 _refine_ls_wR_factor_gt 0.1422 _refine_ls_goodness_of_fit_ref 1.217 _refine_ls_restrained_S_all 1.215 _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 0.2030(2) 0.5000 0.0683(2) 0.0280(6) Uani 1 2 d SD . . N1 N 0.3952(3) 0.5000 0.1539(2) 0.0207(6) Uani 1 2 d S . . N2 N 0.4845(3) 0.5000 0.3242(3) 0.0296(7) Uani 1 2 d S . . N3 N 0.6675(3) 0.5000 0.3633(3) 0.0299(7) Uani 1 2 d S . . N4 N 0.6977(3) 0.5000 0.2215(2) 0.0230(6) Uani 1 2 d S . . C1 C 0.5234(3) 0.5000 0.0894(3) 0.0176(6) Uani 1 2 d S . . O2 O 0.0799(3) 0.5000 0.2816(2) 0.0438(8) Uani 1 2 d SD . . H1 H 0.162(11) 0.5000 0.143(7) 0.16(3) Uiso 1 2 d SD . . H2 H -0.034(3) 0.5000 0.268(6) 0.059(13) Uiso 1 2 d SD . . H3 H 0.148(5) 0.5000 0.3866(15) 0.047(10) Uiso 1 2 d SD . . 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 0.0106(9) 0.0564(12) 0.0165(9) 0.000 0.0055(7) 0.000 N1 0.0133(10) 0.0364(11) 0.0131(10) 0.000 0.0064(8) 0.000 N2 0.0173(10) 0.0569(14) 0.0143(11) 0.000 0.0066(8) 0.000 N3 0.0162(10) 0.0601(15) 0.0138(10) 0.000 0.0069(7) 0.000 N4 0.0153(10) 0.0398(11) 0.0132(10) 0.000 0.0055(8) 0.000 C1 0.0127(10) 0.0252(11) 0.0143(12) 0.000 0.0055(8) 0.000 O2 0.0147(9) 0.103(2) 0.0150(10) 0.000 0.0075(7) 0.000 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 N1 1.340(2) . ? O1 H1 0.84(7) . ? N1 N2 1.332(3) . ? N1 C1 1.338(3) . ? N2 N3 1.304(3) . ? N3 N4 1.353(3) . ? N4 C1 1.334(3) . ? C1 C1 1.434(4) 5_665 ? O2 H2 0.84(3) . ? O2 H3 0.830(14) . ? 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 N1 O1 H1 106(5) . . ? N2 N1 C1 110.36(19) . . ? N2 N1 O1 121.73(18) . . ? C1 N1 O1 127.92(19) . . ? N3 N2 N1 105.34(18) . . ? N2 N3 N4 111.43(19) . . ? C1 N4 N3 105.72(19) . . ? N4 C1 N1 107.16(19) . . ? N4 C1 C1 127.8(2) . 5_665 ? N1 C1 C1 125.0(2) . 5_665 ? H2 O2 H3 106(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 N3 0.0 . . . . ? O1 N1 N2 N3 180.0 . . . . ? N1 N2 N3 N4 0.0 . . . . ? N2 N3 N4 C1 0.0 . . . . ? N3 N4 C1 N1 0.0 . . . . ? N3 N4 C1 C1 180.0 . . . 5_665 ? N2 N1 C1 N4 0.0 . . . . ? O1 N1 C1 N4 180.0 . . . . ? N2 N1 C1 C1 180.0 . . . 5_665 ? O1 N1 C1 C1 0.0 . . . 5_665 ? 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 O1 H1 O2 0.84(7) 1.59(8) 2.430(2) 179(8) . O2 H2 N4 0.84(3) 1.94(3) 2.771(3) 176(5) 1_455 O2 H3 N3 0.830(14 2.012(11) 2.839(3) 175(4) 5_666 _geom_special_details ?