# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address J.Stierstorfer ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; T.M.Klapotke ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; D.Piercey ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; loop_ _publ_contact_author_address ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_contact_author_email tmk@cup.uni-muenchen.de _publ_contact_author_fax '+49 89 2180 77492' _publ_contact_author_phone '+49 89 2180 77491' loop_ _publ_contact_author_name 'Thomas M. Klapotke' _publ_section_title ;Amination of Energetic Anions: High Performing Energetic Materials ; data_fx519 _database_code_depnum_ccdc_archive 'CCDC 871734' _publ_section_abstract ? _publ_section_comment ? _audit_author_name 'Thomas M. Klapo\"tke' _audit_block_code ? _audit_creation_method SHELXL-97 _audit_creation_date ; 'Thu Nov 04 10:56:05 2010' ; _audit_update_record 26.11.2010 _chemical_name_systematic '5-Nitriminotetrazole 2-amino-5H-tetrazole' _chemical_compound_source ? _chemical_name_common '5-Nitriminotetrazole 2-amino-5H-tetrazole' _chemical_formula_moiety ' C H2 N6 O2, C H3 N5' _chemical_formula_sum 'C2 H5 N11 O2' _chemical_formula_weight 215.17 _diffrn_ambient_temperature 173 _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 4024 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.60 _diffrn_reflns_theta_max 26.00 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _reflns_number_total 1565 _reflns_number_gt 1133 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.1012383340 _diffrn_orient_matrix_UB_12 0.0031230566 _diffrn_orient_matrix_UB_13 -0.0085669962 _diffrn_orient_matrix_UB_21 -0.0012773347 _diffrn_orient_matrix_UB_22 -0.0765514802 _diffrn_orient_matrix_UB_23 -0.0157484070 _diffrn_orient_matrix_UB_31 -0.0179141193 _diffrn_orient_matrix_UB_32 0.0230463256 _diffrn_orient_matrix_UB_33 -0.0512839729 _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 13.0616(9) _cell_length_b 8.8579(6) _cell_length_c 6.9023(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.859(7) _cell_angle_gamma 90.00 _cell_volume 798.49(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1505 _cell_measurement_theta_min 4.3206 _cell_measurement_theta_max 33.6017 _cell_special_details ? _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.790 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.154 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.99030 _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 0.159 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.042 _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 1565 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0656 _refine_ls_wR_factor_gt 0.0625 _refine_ls_goodness_of_fit_ref 0.898 _refine_ls_restrained_S_all 0.898 _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 N4 N 0.78843(10) 0.58325(14) -0.18407(19) 0.0196(3) Uani 1 1 d . . . C2 C 0.97466(13) 0.30788(19) 0.3844(2) 0.0253(4) Uani 1 1 d . . . N8 N 0.84363(9) 0.40043(14) 0.27290(18) 0.0188(3) Uani 1 1 d . . . O1 O 0.50298(8) 0.45313(12) -0.27090(16) 0.0262(3) Uani 1 1 d . . . O2 O 0.55702(8) 0.25830(12) -0.43324(16) 0.0283(3) Uani 1 1 d . . . N3 N 0.79100(10) 0.71207(14) -0.07955(19) 0.0235(3) Uani 1 1 d . . . N2 N 0.69838(10) 0.74799(15) -0.04387(19) 0.0246(3) Uani 1 1 d . . . N5 N 0.67249(9) 0.41354(14) -0.32149(17) 0.0197(3) Uani 1 1 d . . . N7 N 0.87493(10) 0.28608(14) 0.38345(18) 0.0256(3) Uani 1 1 d . . . N11 N 0.74294(11) 0.42791(17) 0.2169(2) 0.0247(4) Uani 1 1 d . . . N9 N 0.91697(9) 0.48677(14) 0.20800(18) 0.0227(3) Uani 1 1 d . . . N10 N 1.00296(9) 0.42877(14) 0.28004(19) 0.0238(3) Uani 1 1 d . . . N6 N 0.57287(10) 0.37720(14) -0.33984(18) 0.0206(3) Uani 1 1 d . . . N1 N 0.63671(10) 0.64206(14) -0.12587(18) 0.0206(3) Uani 1 1 d . . . C1 C 0.69244(11) 0.53819(16) -0.2161(2) 0.0180(3) Uani 1 1 d . . . H4 H 0.8473(12) 0.5483(17) -0.221(2) 0.027(5) Uiso 1 1 d . . . H1 H 0.5679(14) 0.6531(19) -0.123(3) 0.042(5) Uiso 1 1 d . . . H11B H 0.7090(13) 0.4464(19) 0.320(3) 0.037(6) Uiso 1 1 d . . . H11A H 0.7161(14) 0.341(2) 0.169(3) 0.045(6) Uiso 1 1 d . . . H2 H 1.0215(13) 0.2491(19) 0.446(2) 0.035(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N4 0.0151(7) 0.0212(7) 0.0227(7) -0.0013(6) -0.0002(6) 0.0003(6) C2 0.0253(10) 0.0258(10) 0.0247(9) 0.0019(8) -0.0010(8) 0.0050(8) N8 0.0180(7) 0.0182(7) 0.0201(7) 0.0008(6) 0.0023(6) 0.0001(6) O1 0.0165(6) 0.0297(7) 0.0326(7) -0.0058(5) 0.0031(5) 0.0031(5) O2 0.0277(6) 0.0239(6) 0.0333(6) -0.0101(5) 0.0018(5) -0.0062(5) N3 0.0251(8) 0.0202(7) 0.0251(7) -0.0002(6) -0.0029(6) 0.0004(6) N2 0.0235(8) 0.0234(8) 0.0268(7) -0.0023(6) -0.0035(6) -0.0017(6) N5 0.0147(7) 0.0204(7) 0.0238(7) -0.0016(6) 0.0008(6) -0.0010(5) N7 0.0264(8) 0.0247(8) 0.0257(8) 0.0073(6) -0.0004(6) 0.0013(6) N11 0.0176(7) 0.0286(9) 0.0279(9) 0.0008(7) 0.0005(7) -0.0012(7) N9 0.0198(7) 0.0222(7) 0.0260(7) 0.0013(6) 0.0010(6) -0.0008(6) N10 0.0208(7) 0.0243(8) 0.0262(7) -0.0017(6) 0.0009(6) 0.0018(6) N6 0.0194(7) 0.0210(7) 0.0214(7) 0.0017(6) 0.0004(6) -0.0003(6) N1 0.0179(7) 0.0207(7) 0.0233(7) -0.0025(6) -0.0012(6) -0.0001(6) C1 0.0184(8) 0.0184(8) 0.0173(8) 0.0048(7) 0.0012(7) 0.0024(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 N4 C1 1.3311(19) . ? N4 N3 1.3502(17) . ? N4 H4 0.870(16) . ? C2 N7 1.317(2) . ? C2 N10 1.346(2) . ? C2 H2 0.905(18) . ? N8 N9 1.3099(17) . ? N8 N7 1.3289(17) . ? N8 N11 1.3868(18) . ? O1 N6 1.2350(15) . ? O2 N6 1.2505(15) . ? N3 N2 1.2783(17) . ? N2 N1 1.3549(17) . ? N5 N6 1.3444(17) . ? N5 C1 1.3457(18) . ? N11 H11B 0.860(18) . ? N11 H11A 0.91(2) . ? N9 N10 1.3252(17) . ? N1 C1 1.3333(19) . ? N1 H1 0.905(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N4 N3 110.97(13) . . ? C1 N4 H4 132.7(11) . . ? N3 N4 H4 116.2(11) . . ? N7 C2 N10 113.18(15) . . ? N7 C2 H2 125.5(11) . . ? N10 C2 H2 121.3(11) . . ? N9 N8 N7 114.91(12) . . ? N9 N8 N11 119.83(12) . . ? N7 N8 N11 125.18(12) . . ? N2 N3 N4 107.29(12) . . ? N3 N2 N1 107.79(12) . . ? N6 N5 C1 115.26(12) . . ? C2 N7 N8 100.77(12) . . ? N8 N11 H11B 107.5(12) . . ? N8 N11 H11A 108.1(12) . . ? H11B N11 H11A 105.3(16) . . ? N8 N9 N10 105.39(11) . . ? N9 N10 C2 105.74(13) . . ? O1 N6 O2 122.66(12) . . ? O1 N6 N5 123.59(12) . . ? O2 N6 N5 113.75(12) . . ? C1 N1 N2 110.34(13) . . ? C1 N1 H1 129.4(11) . . ? N2 N1 H1 120.1(11) . . ? N4 C1 N1 103.60(13) . . ? N4 C1 N5 120.67(13) . . ? N1 C1 N5 135.73(14) . . ? 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 0.56(17) . . . . ? N4 N3 N2 N1 -0.06(16) . . . . ? N10 C2 N7 N8 -0.09(17) . . . . ? N9 N8 N7 C2 0.45(17) . . . . ? N11 N8 N7 C2 177.16(14) . . . . ? N7 N8 N9 N10 -0.64(16) . . . . ? N11 N8 N9 N10 -177.54(13) . . . . ? N8 N9 N10 C2 0.52(15) . . . . ? N7 C2 N10 N9 -0.28(18) . . . . ? C1 N5 N6 O1 1.94(19) . . . . ? C1 N5 N6 O2 -177.83(12) . . . . ? N3 N2 N1 C1 -0.46(17) . . . . ? N3 N4 C1 N1 -0.81(16) . . . . ? N3 N4 C1 N5 178.52(13) . . . . ? N2 N1 C1 N4 0.77(16) . . . . ? N2 N1 C1 N5 -178.40(16) . . . . ? N6 N5 C1 N4 178.40(13) . . . . ? N6 N5 C1 N1 -2.5(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 N4 H4 N10 0.870(16) 2.015(16) 2.8157(18) 152.6(14) 3_765 N1 H1 O2 0.905(18) 1.923(18) 2.7678(17) 154.5(15) 2_654 N11 H11B N5 0.860(18) 2.544(19) 3.332(2) 152.9(15) 1_556 N11 H11A N5 0.91(2) 2.32(2) 3.1714(19) 154.9(16) 4_566 N11 H11A O2 0.91(2) 2.35(2) 3.1010(18) 139.3(15) 4_566 N11 H11A N6 0.91(2) 2.69(2) 3.517(2) 151.8(15) 4_566 _geom_special_details ? _iucr_refine_instructions_details ; TITL v1 in P2(1)/c CELL 0.71073 13.0616 8.8579 6.9023 90.000 90.859 90.000 ZERR 4.00 0.0009 0.0006 0.0005 0.000 0.007 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 8 20 44 8 MERG 2 OMIT -2.00 52.00 EQIV $1 -x+2, -y+1, -z EQIV $2 -x+1, y+1/2, -z-1/2 EQIV $3 x, y, z+1 EQIV $4 x, -y+1/2, z+1/2 HTAB N4 N10_$1 HTAB N1 O2_$2 HTAB N11 N5_$3 HTAB N11 N5_$4 HTAB N11 O2_$4 HTAB N11 N6_$4 FMAP 2 PLAN 50 ACTA BOND $H CONF L.S. 4 TEMP -100.00 WGHT 0.030100 FVAR 0.24430 N4 3 0.788433 0.583249 -0.184070 11.00000 0.01507 0.02118 = 0.02268 -0.00126 -0.00017 0.00027 C2 1 0.974665 0.307880 0.384425 11.00000 0.02530 0.02580 = 0.02469 0.00194 -0.00095 0.00504 N8 3 0.843634 0.400429 0.272903 11.00000 0.01802 0.01823 = 0.02009 0.00079 0.00230 0.00012 O1 4 0.502985 0.453128 -0.270899 11.00000 0.01648 0.02970 = 0.03259 -0.00579 0.00314 0.00307 O2 4 0.557021 0.258298 -0.433240 11.00000 0.02768 0.02390 = 0.03334 -0.01007 0.00181 -0.00625 N3 3 0.791000 0.712073 -0.079546 11.00000 0.02511 0.02022 = 0.02512 -0.00021 -0.00291 0.00041 N2 3 0.698384 0.747988 -0.043873 11.00000 0.02354 0.02342 = 0.02681 -0.00233 -0.00348 -0.00166 N5 3 0.672487 0.413538 -0.321488 11.00000 0.01471 0.02045 = 0.02383 -0.00162 0.00078 -0.00104 N7 3 0.874931 0.286076 0.383446 11.00000 0.02644 0.02466 = 0.02569 0.00733 -0.00037 0.00132 N11 3 0.742944 0.427914 0.216892 11.00000 0.01760 0.02855 = 0.02795 0.00077 0.00046 -0.00119 N9 3 0.916966 0.486770 0.208002 11.00000 0.01984 0.02218 = 0.02602 0.00134 0.00105 -0.00080 N10 3 1.002963 0.428774 0.280037 11.00000 0.02084 0.02430 = 0.02619 -0.00167 0.00095 0.00177 N6 3 0.572875 0.377201 -0.339843 11.00000 0.01939 0.02095 = 0.02145 0.00174 0.00043 -0.00032 N1 3 0.636714 0.642063 -0.125866 11.00000 0.01785 0.02069 = 0.02332 -0.00247 -0.00123 -0.00010 C1 1 0.692444 0.538190 -0.216057 11.00000 0.01843 0.01835 = 0.01726 0.00478 0.00119 0.00235 H4 2 0.847267 0.548314 -0.220939 11.00000 0.02675 H1 2 0.567856 0.653079 -0.123031 11.00000 0.04212 H11B 2 0.708981 0.446367 0.320003 11.00000 0.03692 H11A 2 0.716146 0.340568 0.168534 11.00000 0.04533 H2 2 1.021542 0.249114 0.445958 11.00000 0.03462 HKLF 4 REM v1 in P2(1)/c REM R1 = 0.0302 for 1133 Fo > 4sig(Fo) and 0.0496 for all 1565 data REM 156 parameters refined using 0 restraints END WGHT 0.0301 0.0000 REM Highest difference peak 0.159, deepest hole -0.190, 1-sigma level 0.042 Q1 1 0.7246 0.4205 -0.3887 11.00000 0.05 0.16 Q2 1 0.6794 0.4605 -0.2581 11.00000 0.05 0.16 Q3 1 0.8613 0.7405 -0.0652 11.00000 0.05 0.16 Q4 1 0.6592 0.5543 -0.1615 11.00000 0.05 0.16 Q5 1 0.6391 0.4205 -0.4046 11.00000 0.05 0.16 Q6 1 1.0577 0.4602 0.2253 11.00000 0.05 0.16 Q7 1 1.0645 0.4768 0.3341 11.00000 0.05 0.15 Q8 1 0.5569 0.5413 -0.2069 11.00000 0.05 0.14 Q9 1 1.0751 0.3934 0.2492 11.00000 0.05 0.14 Q10 1 0.4197 0.3989 -0.2495 11.00000 0.05 0.14 Q11 1 0.8818 0.7237 -0.2429 11.00000 0.05 0.13 Q12 1 0.7014 0.3545 -0.2751 11.00000 0.05 0.13 Q13 1 0.6763 0.5447 0.0030 11.00000 0.05 0.13 Q14 1 0.7390 0.5158 0.1260 11.00000 0.05 0.13 Q15 1 0.4301 0.3822 -0.3310 11.00000 0.05 0.12 Q16 1 0.8600 0.3273 0.3006 11.00000 0.05 0.12 Q17 1 0.4979 0.2647 -0.5710 11.00000 0.05 0.12 Q18 1 0.5168 0.7181 -0.0514 11.00000 0.05 0.12 Q19 1 0.7269 0.4702 0.0925 11.00000 0.05 0.12 Q20 1 1.0005 0.1930 0.6348 11.00000 0.05 0.12 Q21 1 0.6416 0.2546 -0.4326 11.00000 0.05 0.11 Q22 1 1.0048 0.3691 0.2863 11.00000 0.05 0.11 Q23 1 0.8005 0.8758 -0.2143 11.00000 0.05 0.11 Q24 1 0.8146 0.2333 0.3416 11.00000 0.05 0.11 Q25 1 0.5531 0.6068 -0.3955 11.00000 0.05 0.11 Q26 1 0.8776 0.4145 0.5381 11.00000 0.05 0.11 Q27 1 0.8543 0.2337 0.4484 11.00000 0.05 0.11 Q28 1 0.9018 0.3138 0.4390 11.00000 0.05 0.11 Q29 1 1.0460 0.1675 0.6236 11.00000 0.05 0.11 Q30 1 0.7462 0.6655 -0.3319 11.00000 0.05 0.11 Q31 1 0.7978 0.4185 0.2748 11.00000 0.05 0.10 Q32 1 0.8793 0.5758 0.0974 11.00000 0.05 0.10 Q33 1 0.7993 0.3904 0.0923 11.00000 0.05 0.10 Q34 1 1.0415 0.3836 0.5846 11.00000 0.05 0.10 Q35 1 1.0109 0.2714 0.5277 11.00000 0.05 0.10 Q36 1 0.6205 0.7861 -0.0589 11.00000 0.05 0.10 Q37 1 0.8090 0.1909 0.4553 11.00000 0.05 0.10 Q38 1 0.6318 0.3401 0.4109 11.00000 0.05 0.10 Q39 1 0.6941 0.8531 -0.0328 11.00000 0.05 0.10 Q40 1 0.8827 0.3956 0.0298 11.00000 0.05 0.10 Q41 1 0.6709 0.4896 0.1861 11.00000 0.05 0.10 Q42 1 0.5861 0.6178 -0.0920 11.00000 0.05 0.10 Q43 1 1.0156 0.0814 0.5264 11.00000 0.05 0.10 Q44 1 0.5967 0.6456 -0.1174 11.00000 0.05 0.10 Q45 1 0.9133 0.4407 0.5570 11.00000 0.05 0.10 Q46 1 0.7752 0.1834 0.0870 11.00000 0.05 0.09 Q47 1 0.6583 0.4405 -0.4966 11.00000 0.05 0.09 Q48 1 0.9035 0.6362 0.2606 11.00000 0.05 0.09 Q49 1 0.4583 0.2745 -0.4918 11.00000 0.05 0.09 Q50 1 0.6683 0.6818 -0.0444 11.00000 0.05 0.09 ; # Attachment '- gx037_ATTNE2.cif' data_gx037 _database_code_depnum_ccdc_archive 'CCDC 871735' _publ_section_abstract ? _publ_section_comment ? _audit_author_name 'Joerg Stierstorfer' _audit_block_code ? _audit_creation_method SHELXL-97 _audit_creation_date ; 'Fri Jan 21 16:41:00 2011' ; _audit_update_record 1-Trinitroethylamino-tetrazole _chemical_name_systematic ? _chemical_compound_source 1-Trinitroethylamino-tetrazole _chemical_name_common ? _chemical_formula_moiety ' C3 H4 N8 O6' _chemical_formula_sum ' C3 H4 N8 O6' _chemical_formula_weight 248.14 _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 4041 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.36 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _reflns_number_total 1574 _reflns_number_gt 1139 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.0383873458 _diffrn_orient_matrix_UB_12 0.0318112243 _diffrn_orient_matrix_UB_13 0.0430726957 _diffrn_orient_matrix_UB_21 -0.0605582859 _diffrn_orient_matrix_UB_22 -0.0281012254 _diffrn_orient_matrix_UB_23 -0.0321631944 _diffrn_orient_matrix_UB_31 0.0059248270 _diffrn_orient_matrix_UB_32 -0.0808529608 _diffrn_orient_matrix_UB_33 0.0280747051 _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 9.9097(5) _cell_length_b 7.7761(4) _cell_length_c 11.7846(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.124(5) _cell_angle_gamma 90.00 _cell_volume 902.92(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1800 _cell_measurement_theta_min 4.3446 _cell_measurement_theta_max 33.4889 _cell_special_details ? _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.825 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.172 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.91738 _exptl_absorpt_correction_T_max 0.99000 _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 0.337 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.049 _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 1574 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0862 _refine_ls_wR_factor_gt 0.0819 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _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 O5 O 0.22403(16) -0.01453(18) 0.42390(13) 0.0449(4) Uani 1 1 d . . . O6 O 0.11899(14) 0.10501(17) 0.55653(12) 0.0345(4) Uani 1 1 d . . . O4 O 0.43813(15) 0.13097(18) 0.59940(12) 0.0383(4) Uani 1 1 d . . . O3 O 0.42101(14) 0.40742(17) 0.61483(11) 0.0330(4) Uani 1 1 d . . . O2 O 0.46307(14) 0.24836(17) 0.37144(12) 0.0348(4) Uani 1 1 d . . . O1 O 0.26146(16) 0.27963(19) 0.27966(11) 0.0383(4) Uani 1 1 d . . . N8 N 0.19808(16) 0.10375(19) 0.48502(14) 0.0253(4) Uani 1 1 d . . . N7 N 0.38882(16) 0.2696(2) 0.57285(13) 0.0230(4) Uani 1 1 d . . . N6 N 0.34060(17) 0.26491(19) 0.36545(14) 0.0246(4) Uani 1 1 d . . . N5 N 0.24261(16) 0.5816(2) 0.44330(13) 0.0209(4) Uani 1 1 d . . . N1 N 0.19326(14) 0.64026(18) 0.33454(12) 0.0199(4) Uani 1 1 d . . . N2 N 0.06023(15) 0.6610(2) 0.29875(13) 0.0269(4) Uani 1 1 d . . . N3 N 0.05621(18) 0.7259(2) 0.19708(14) 0.0289(4) Uani 1 1 d . . . N4 N 0.18417(17) 0.74863(19) 0.16628(13) 0.0266(4) Uani 1 1 d . . . C3 C 0.27389(18) 0.2716(2) 0.47542(15) 0.0188(4) Uani 1 1 d . . . C2 C 0.17900(19) 0.4235(2) 0.47769(16) 0.0185(4) Uani 1 1 d . . . C1 C 0.2659(2) 0.6947(2) 0.25336(17) 0.0256(5) Uani 1 1 d . . . H2B H 0.1490(15) 0.4288(18) 0.5538(14) 0.000(4) Uiso 1 1 d . . . H1 H 0.358(2) 0.695(2) 0.2595(17) 0.027(5) Uiso 1 1 d . . . H2A H 0.1030(19) 0.396(2) 0.4286(16) 0.021(5) Uiso 1 1 d . . . H5 H 0.236(2) 0.663(3) 0.495(2) 0.035(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 O5 0.0623(11) 0.0258(8) 0.0491(9) -0.0152(7) 0.0170(8) -0.0043(7) O6 0.0398(8) 0.0305(8) 0.0348(9) 0.0039(6) 0.0122(7) -0.0073(6) O4 0.0445(9) 0.0361(9) 0.0327(9) 0.0009(7) -0.0038(7) 0.0193(7) O3 0.0364(8) 0.0327(8) 0.0274(8) 0.0027(6) -0.0080(6) -0.0097(7) O2 0.0260(8) 0.0465(9) 0.0337(8) -0.0007(6) 0.0113(7) 0.0035(7) O1 0.0396(9) 0.0590(10) 0.0160(8) -0.0019(7) 0.0017(7) 0.0116(7) N8 0.0302(9) 0.0219(9) 0.0237(9) -0.0010(7) 0.0022(8) 0.0003(7) N7 0.0219(9) 0.0292(10) 0.0182(9) 0.0033(7) 0.0031(7) 0.0026(7) N6 0.0298(10) 0.0258(9) 0.0191(9) -0.0010(7) 0.0065(8) 0.0037(7) N5 0.0273(9) 0.0211(8) 0.0136(8) 0.0016(7) -0.0009(7) -0.0023(7) N1 0.0220(8) 0.0200(8) 0.0170(8) 0.0002(6) -0.0010(7) -0.0004(7) N2 0.0241(9) 0.0307(9) 0.0249(9) 0.0011(7) -0.0013(7) 0.0062(7) N3 0.0316(10) 0.0328(9) 0.0218(9) 0.0048(7) -0.0002(8) 0.0059(8) N4 0.0327(10) 0.0282(9) 0.0183(9) 0.0036(7) -0.0002(8) -0.0026(7) C3 0.0211(10) 0.0220(10) 0.0132(9) -0.0004(7) 0.0024(8) -0.0028(8) C2 0.0200(10) 0.0212(10) 0.0143(10) -0.0004(8) 0.0020(8) -0.0024(8) C1 0.0246(11) 0.0311(11) 0.0211(11) 0.0016(9) 0.0023(9) -0.0046(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 O5 N8 1.213(2) . ? O6 N8 1.211(2) . ? O4 N7 1.2110(19) . ? O3 N7 1.2087(19) . ? O2 N6 1.215(2) . ? O1 N6 1.217(2) . ? N8 C3 1.516(2) . ? N7 C3 1.529(2) . ? N6 C3 1.517(2) . ? N5 N1 1.399(2) . ? N5 C2 1.459(2) . ? N5 H5 0.89(2) . ? N1 C1 1.327(2) . ? N1 N2 1.350(2) . ? N2 N3 1.297(2) . ? N3 N4 1.367(2) . ? N4 C1 1.307(2) . ? C3 C2 1.512(2) . ? C2 H2B 0.975(16) . ? C2 H2A 0.925(19) . ? C1 H1 0.90(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 N8 O5 127.86(16) . . ? O6 N8 C3 114.06(14) . . ? O5 N8 C3 118.06(16) . . ? O3 N7 O4 127.01(16) . . ? O3 N7 C3 116.21(14) . . ? O4 N7 C3 116.78(15) . . ? O2 N6 O1 127.55(17) . . ? O2 N6 C3 118.52(16) . . ? O1 N6 C3 113.92(15) . . ? N1 N5 C2 114.23(15) . . ? N1 N5 H5 110.4(14) . . ? C2 N5 H5 110.2(14) . . ? C1 N1 N2 108.87(15) . . ? C1 N1 N5 126.97(16) . . ? N2 N1 N5 124.02(14) . . ? N3 N2 N1 105.54(15) . . ? N2 N3 N4 110.96(15) . . ? C1 N4 N3 105.35(15) . . ? C2 C3 N8 110.92(15) . . ? C2 C3 N6 111.73(14) . . ? N8 C3 N6 107.40(14) . . ? C2 C3 N7 114.17(15) . . ? N8 C3 N7 105.72(13) . . ? N6 C3 N7 106.48(14) . . ? N5 C2 C3 111.44(15) . . ? N5 C2 H2B 113.8(9) . . ? C3 C2 H2B 107.5(9) . . ? N5 C2 H2A 111.7(11) . . ? C3 C2 H2A 105.9(11) . . ? H2B C2 H2A 106.1(14) . . ? N4 C1 N1 109.28(18) . . ? N4 C1 H1 126.6(13) . . ? N1 C1 H1 124.1(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N5 N1 C1 -134.05(18) . . . . ? C2 N5 N1 N2 50.7(2) . . . . ? C1 N1 N2 N3 0.48(19) . . . . ? N5 N1 N2 N3 176.46(15) . . . . ? N1 N2 N3 N4 -0.33(19) . . . . ? N2 N3 N4 C1 0.1(2) . . . . ? O6 N8 C3 C2 -43.9(2) . . . . ? O5 N8 C3 C2 137.41(17) . . . . ? O6 N8 C3 N6 -166.27(15) . . . . ? O5 N8 C3 N6 15.1(2) . . . . ? O6 N8 C3 N7 80.34(17) . . . . ? O5 N8 C3 N7 -98.33(18) . . . . ? O2 N6 C3 C2 129.97(16) . . . . ? O1 N6 C3 C2 -49.1(2) . . . . ? O2 N6 C3 N8 -108.18(17) . . . . ? O1 N6 C3 N8 72.74(18) . . . . ? O2 N6 C3 N7 4.7(2) . . . . ? O1 N6 C3 N7 -174.38(14) . . . . ? O3 N7 C3 C2 -24.8(2) . . . . ? O4 N7 C3 C2 155.51(15) . . . . ? O3 N7 C3 N8 -146.98(15) . . . . ? O4 N7 C3 N8 33.31(19) . . . . ? O3 N7 C3 N6 98.99(17) . . . . ? O4 N7 C3 N6 -80.72(17) . . . . ? N1 N5 C2 C3 106.86(17) . . . . ? N8 C3 C2 N5 -167.26(14) . . . . ? N6 C3 C2 N5 -47.5(2) . . . . ? N7 C3 C2 N5 73.43(19) . . . . ? N3 N4 C1 N1 0.2(2) . . . . ? N2 N1 C1 N4 -0.5(2) . . . . ? N5 N1 C1 N4 -176.29(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 ? ? ? ? ? ? ? ? _geom_special_details ? _iucr_refine_instructions_details ; TITL p-1 in P-1 New: P21/c CELL 0.71073 9.9097 7.7761 11.7846 90.000 96.124 90.000 ZERR 1.00 0.0005 0.0004 0.0006 0.000 0.005 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 12 16 32 24 MERG 2 OMIT -2.00 52.00 OMIT 4 0 0 OMIT 0 4 1 OMIT -3 0 8 OMIT 1 1 4 OMIT 4 0 8 OMIT 4 6 0 FMAP 2 PLAN 20 ACTA BOND $H CONF L.S. 5 TEMP -100.00 WGHT 0.050200 FVAR 0.21795 O5 4 0.223967 -0.014588 0.423831 11.00000 0.06257 0.02563 = 0.04916 -0.01534 0.01707 -0.00496 O6 4 0.119003 0.104985 0.556630 11.00000 0.03934 0.03048 = 0.03482 0.00390 0.01224 -0.00721 O4 4 0.438081 0.130890 0.599378 11.00000 0.04453 0.03589 = 0.03240 0.00083 -0.00359 0.01926 O3 4 0.421015 0.407399 0.614769 11.00000 0.03625 0.03268 = 0.02737 0.00255 -0.00783 -0.00988 O2 4 0.463064 0.248207 0.371381 11.00000 0.02606 0.04619 = 0.03293 -0.00048 0.01120 0.00336 O1 4 0.261435 0.279446 0.279686 11.00000 0.03991 0.05915 = 0.01578 -0.00173 0.00240 0.01185 N8 3 0.198022 0.103687 0.485108 11.00000 0.03020 0.02126 = 0.02407 -0.00117 0.00216 0.00008 N7 3 0.388807 0.269731 0.572884 11.00000 0.02183 0.02980 = 0.01694 0.00335 0.00281 0.00252 N6 3 0.340599 0.264798 0.365330 11.00000 0.02968 0.02609 = 0.01822 -0.00093 0.00644 0.00364 N5 3 0.242663 0.581653 0.443358 11.00000 0.02716 0.02047 = 0.01377 0.00181 -0.00073 -0.00212 N1 3 0.193153 0.640396 0.334482 11.00000 0.02210 0.01963 = 0.01737 0.00019 -0.00087 -0.00079 N2 3 0.060313 0.661180 0.298847 11.00000 0.02406 0.03002 = 0.02465 0.00133 -0.00126 0.00648 N3 3 0.056288 0.725736 0.197184 11.00000 0.03120 0.03237 = 0.02194 0.00487 -0.00035 0.00586 N4 3 0.184168 0.748504 0.166291 11.00000 0.03270 0.02809 = 0.01821 0.00366 -0.00036 -0.00234 C3 1 0.273942 0.271466 0.475457 11.00000 0.02119 0.02127 = 0.01334 -0.00014 0.00255 -0.00214 C2 1 0.178887 0.423512 0.477682 11.00000 0.02004 0.02080 = 0.01484 -0.00034 0.00235 -0.00238 C1 1 0.265931 0.694798 0.253398 11.00000 0.02488 0.03028 = 0.02043 0.00182 0.00192 -0.00463 H2B 2 0.149055 0.429517 0.553973 11.00000 0.00176 H1 2 0.358081 0.693950 0.258677 11.00000 0.02659 H2A 2 0.102982 0.395436 0.428506 11.00000 0.02054 H5 2 0.234583 0.664580 0.495810 11.00000 0.03354 HKLF 4 REM p-1 in P-1 New: P21/c REM R1 = 0.0348 for 1225 Fo > 4sig(Fo) and 0.0543 for all 1758 data REM 170 parameters refined using 0 restraints END WGHT 0.0502 0.0000 REM Highest difference peak 0.338, deepest hole -0.191, 1-sigma level 0.050 Q1 1 0.1887 -0.1459 0.3361 11.00000 0.05 0.34 Q2 1 0.0532 0.8398 0.3011 11.00000 0.05 0.29 Q3 1 0.2297 0.3444 0.4816 11.00000 0.05 0.26 Q4 1 0.1160 0.3646 0.5552 11.00000 0.05 0.25 Q5 1 0.2427 -0.1218 0.4522 11.00000 0.05 0.25 Q6 1 0.2514 0.1995 0.4771 11.00000 0.05 0.24 Q7 1 0.2200 0.4815 0.4348 11.00000 0.05 0.23 Q8 1 0.3062 0.2733 0.4263 11.00000 0.05 0.21 Q9 1 0.3215 0.2757 0.5127 11.00000 0.05 0.20 Q10 1 0.2582 0.8264 0.2512 11.00000 0.05 0.19 Q11 1 0.2772 0.1636 0.2599 11.00000 0.05 0.19 Q12 1 0.1945 0.7349 0.1198 11.00000 0.05 0.19 Q13 1 0.2137 0.7545 0.1955 11.00000 0.05 0.18 Q14 1 0.1081 0.7748 0.1802 11.00000 0.05 0.17 Q15 1 0.2067 0.4426 0.5726 11.00000 0.05 0.17 Q16 1 0.3203 0.5289 0.4109 11.00000 0.05 0.16 Q17 1 0.3965 0.0792 0.6771 11.00000 0.05 0.14 Q18 1 0.0294 0.7983 0.1667 11.00000 0.05 0.13 Q19 1 0.3773 0.7787 0.2841 11.00000 0.05 0.12 Q20 1 0.2813 0.3112 0.2412 11.00000 0.05 0.12 ; # Attachment '- gx460_2ANT.cif' data_gx460 _database_code_depnum_ccdc_archive 'CCDC 871736' _publ_section_abstract ? _publ_section_comment ? _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 Aug 04 16:28:26 2011' ; _audit_update_record 30.11.2011 _chemical_name_systematic 2-amino-5-nitrotetrazole _chemical_compound_source ? _chemical_name_common 2-amino-5-nitrotetrazole _chemical_formula_moiety 'C H2 N6 O2' _chemical_formula_sum 'C H2 N6 O2' _chemical_formula_weight 130.09 _cell_length_a 9.855(6) _cell_length_b 8.082(4) _cell_length_c 6.059(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 482.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 342 _cell_measurement_theta_min 4.1272 _cell_measurement_theta_max 33.3664 _cell_special_details ? _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.791 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.162 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9561 _exptl_absorpt_correction_T_max 0.9856 _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 2405 _diffrn_reflns_av_R_equivalents 0.1301 _diffrn_reflns_av_sigmaI/netI 0.0852 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.14 _diffrn_reflns_theta_max 26.50 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.989 _reflns_number_total 543 _reflns_number_gt 398 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.0423471000 _diffrn_orient_matrix_UB_12 0.0498906000 _diffrn_orient_matrix_UB_13 -0.0670848000 _diffrn_orient_matrix_UB_21 -0.0580011000 _diffrn_orient_matrix_UB_22 -0.0307301000 _diffrn_orient_matrix_UB_23 0.0567710000 _diffrn_orient_matrix_UB_31 0.0053054000 _diffrn_orient_matrix_UB_32 0.0652457000 _diffrn_orient_matrix_UB_33 0.0773936000 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_Int_Tables_number 33 _symmetry_space_group_name_Hall ? 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 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+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, 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 0.188 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.056 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0247P)^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 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 543 _refine_ls_number_parameters 90 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0699 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.0984 _refine_ls_wR_factor_gt 0.0861 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.001 _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 0.7984(3) 0.4021(4) 0.3017(7) 0.0399(9) Uani 1 1 d . . . O1 O 0.9733(3) 0.3744(3) 0.0846(6) 0.0381(9) Uani 1 1 d . . . N1 N 0.9477(3) 0.0398(4) 0.1027(7) 0.0291(9) Uani 1 1 d . . . N4 N 0.7664(4) 0.0694(5) 0.3264(8) 0.0345(10) Uani 1 1 d . . . N6 N 0.9506(4) -0.2528(5) 0.0994(8) 0.0318(10) Uani 1 1 d . . . N5 N 0.8792(4) 0.3178(4) 0.1974(7) 0.0308(10) Uani 1 1 d . . . N2 N 0.8937(3) -0.1034(5) 0.1686(7) 0.0283(9) Uani 1 1 d . . . N3 N 0.7870(3) -0.0919(4) 0.3000(8) 0.0328(9) Uani 1 1 d . . . C1 C 0.8638(4) 0.1409(5) 0.2089(9) 0.0285(11) Uani 1 1 d . . . H6A H 0.880(5) -0.317(7) 0.004(11) 0.070(19) Uiso 1 1 d . . . H6B H 0.998(7) -0.297(9) 0.198(14) 0.12(3) 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 0.0460(19) 0.0353(18) 0.039(2) -0.002(2) 0.003(2) 0.0133(17) O1 0.042(2) 0.0365(18) 0.035(2) 0.0045(18) 0.0037(18) -0.0026(17) N1 0.034(2) 0.0278(18) 0.026(2) 0.003(2) -0.002(2) -0.0042(18) N4 0.036(2) 0.034(2) 0.034(3) 0.000(2) 0.003(2) -0.0029(18) N6 0.034(3) 0.029(2) 0.032(2) 0.001(3) -0.003(2) 0.003(2) N5 0.039(2) 0.028(2) 0.026(2) -0.001(2) -0.006(2) -0.0004(18) N2 0.0283(19) 0.030(2) 0.026(2) -0.0049(16) -0.0007(19) -0.0011(17) N3 0.029(2) 0.038(2) 0.032(2) -0.001(2) 0.002(2) -0.0039(18) C1 0.030(2) 0.028(2) 0.028(3) 0.000(2) 0.001(2) -0.002(2) 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 1.224(5) . ? O1 N5 1.239(5) . ? N1 C1 1.328(5) . ? N1 N2 1.334(5) . ? N4 C1 1.328(6) . ? N4 N3 1.329(5) . ? N6 N2 1.396(5) . ? N6 H6A 1.04(6) . ? N6 H6B 0.84(8) . ? N5 C1 1.439(5) . ? N2 N3 1.322(5) . ? 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 98.1(4) . . ? C1 N4 N3 104.6(4) . . ? N2 N6 H6A 109(3) . . ? N2 N6 H6B 112(5) . . ? H6A N6 H6B 124(6) . . ? O2 N5 O1 124.5(4) . . ? O2 N5 C1 117.3(4) . . ? O1 N5 C1 118.1(4) . . ? N3 N2 N1 115.9(4) . . ? N3 N2 N6 124.1(4) . . ? N1 N2 N6 120.0(4) . . ? N2 N3 N4 105.2(4) . . ? N4 C1 N1 116.2(4) . . ? N4 C1 N5 122.3(4) . . ? N1 C1 N5 121.5(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 0.6(5) . . . . ? C1 N1 N2 N6 -179.2(4) . . . . ? N1 N2 N3 N4 -0.1(5) . . . . ? N6 N2 N3 N4 179.6(4) . . . . ? C1 N4 N3 N2 -0.4(5) . . . . ? N3 N4 C1 N1 0.8(6) . . . . ? N3 N4 C1 N5 -178.7(4) . . . . ? N2 N1 C1 N4 -0.8(6) . . . . ? N2 N1 C1 N5 178.7(4) . . . . ? O2 N5 C1 N4 0.2(6) . . . . ? O1 N5 C1 N4 179.7(5) . . . . ? O2 N5 C1 N1 -179.4(5) . . . . ? O1 N5 C1 N1 0.2(6) . . . . ? 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 N6 H6A N4 1.04(6) 2.02(6) 3.062(6) 176(4) 3_644 N6 H6B O1 0.84(8) 2.44(8) 3.189(6) 149(7) 2_755 _geom_special_details ? _iucr_refine_instructions_details ; TITL v1 in Pna2(1) CELL 0.71073 9.8554 8.0819 6.0585 90.000 90.000 90.000 ZERR 4.00 0.0056 0.0044 0.0038 0.000 0.000 0.000 LATT -1 SYMM - X, - Y, 1/2 + Z SYMM 1/2 - X, 1/2 + Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, Z SFAC C H N O UNIT 4 8 24 8 MERG 4 OMIT -2.00 53.00 OMIT 6 1 4 OMIT 3 1 7 OMIT 3 3 4 OMIT 1 7 5 OMIT 10 0 2 EQIV $1 -x+3/2, y-1/2, z-1/2 EQIV $2 -x+2, -y, z+1/2 HTAB N6 N4_$1 HTAB N6 O1_$2 FMAP 2 PLAN 25 SIZE 0.09 0.20 0.28 ACTA BOND $H CONF L.S. 4 TEMP -100.00 WGHT 0.024700 FVAR 0.43036 O2 4 0.798358 0.402052 0.301687 11.00000 0.04595 0.03530 = 0.03858 -0.00215 0.00298 0.01332 O1 4 0.973254 0.374407 0.084574 11.00000 0.04233 0.03651 = 0.03549 0.00449 0.00368 -0.00263 N1 3 0.947650 0.039789 0.102692 11.00000 0.03384 0.02780 = 0.02568 0.00299 -0.00208 -0.00418 N4 3 0.766432 0.069402 0.326443 11.00000 0.03565 0.03419 = 0.03362 0.00024 0.00350 -0.00293 N6 3 0.950626 -0.252801 0.099385 11.00000 0.03435 0.02875 = 0.03226 0.00101 -0.00289 0.00347 N5 3 0.879182 0.317823 0.197393 11.00000 0.03852 0.02822 = 0.02556 -0.00147 -0.00620 -0.00038 N2 3 0.893736 -0.103384 0.168642 11.00000 0.02829 0.03027 = 0.02622 -0.00488 -0.00073 -0.00108 N3 3 0.787006 -0.091903 0.299999 11.00000 0.02888 0.03754 = 0.03201 -0.00059 0.00186 -0.00387 C1 1 0.863842 0.140904 0.208855 11.00000 0.02953 0.02811 = 0.02775 -0.00043 0.00117 -0.00205 H6A 2 0.880112 -0.317033 0.004047 11.00000 0.07024 H6B 2 0.997828 -0.297166 0.197790 11.00000 0.11686 HKLF 4 REM v1 in Pna2(1) REM R1 = 0.0447 for 398 Fo > 4sig(Fo) and 0.0699 for all 543 data REM 90 parameters refined using 1 restraints END WGHT 0.0248 0.0000 REM Highest difference peak 0.188, deepest hole -0.197, 1-sigma level 0.056 Q1 1 1.0723 -0.2156 0.0479 11.00000 0.05 0.19 Q2 1 0.9399 -0.0046 0.1380 11.00000 0.05 0.18 Q3 1 0.8979 0.0928 0.1559 11.00000 0.05 0.18 Q4 1 1.0065 0.0826 0.1573 11.00000 0.05 0.16 Q5 1 0.8572 0.4464 0.5275 11.00000 0.05 0.16 Q6 1 1.0310 -0.1920 -0.0998 11.00000 0.05 0.16 Q7 1 0.6931 -0.0032 0.1604 11.00000 0.05 0.16 Q8 1 0.8382 -0.3514 0.4066 11.00000 0.05 0.16 Q9 1 0.8960 0.0704 -0.1543 11.00000 0.05 0.16 Q10 1 0.8237 -0.4130 -0.0546 11.00000 0.05 0.15 Q11 1 0.9614 0.1701 -0.0862 11.00000 0.05 0.15 Q12 1 1.0414 0.3161 0.2052 11.00000 0.05 0.15 Q13 1 0.9335 0.2200 0.1020 11.00000 0.05 0.15 Q14 1 1.0047 0.0092 -0.0366 11.00000 0.05 0.15 Q15 1 0.8233 -0.2466 0.5355 11.00000 0.05 0.15 Q16 1 0.8598 0.0015 -0.0123 11.00000 0.05 0.15 Q17 1 1.0640 -0.1671 0.2141 11.00000 0.05 0.15 Q18 1 0.9076 0.1078 0.4865 11.00000 0.05 0.15 Q19 1 0.6286 -0.0369 0.3463 11.00000 0.05 0.14 Q20 1 1.0521 0.4777 0.2076 11.00000 0.05 0.14 Q21 1 0.9821 -0.0651 0.3163 11.00000 0.05 0.14 Q22 1 0.9191 -0.1437 0.4284 11.00000 0.05 0.14 Q23 1 1.1014 0.1182 0.1323 11.00000 0.05 0.14 Q24 1 0.7581 0.5545 0.3425 11.00000 0.05 0.14 Q25 1 0.9804 -0.0491 -0.0374 11.00000 0.05 0.14 ; data_gx516 _database_code_depnum_ccdc_archive 'CCDC 871737' _vrf_PLAT089_gx516 ; RESPONSE: Die low data/parameter ratio is caused by the noncentrosymetric space group P1. In addition the positions of the hydrogen atoms were refined. The eight molecules in the noncentrosymmetric triclinic unit cell are connected by numerous N-O contacts in particular nitro-nitro group interactions. ; _vrf_STRVA01_gx516 ; RESPONSE: The meaningless flack value of 0.2(10) is caused by the SHELXL command MERG3 which is recommended for non-centrosymmetric space groups including only atoms with Z < Si. ; _publ_section_abstract ? _publ_section_comment ? _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 ; 'Tue Sep 06 13:04:56 2011' ; _audit_update_record 10.05.2012 _chemical_name_systematic 1-amino-3,5-dinitro-1,2,4-triazole _chemical_compound_source ? _chemical_name_common 1-amino-3,5-dinitro-1,2,4-triazole _chemical_formula_moiety 'C2 H2 N6 O4' _chemical_formula_sum 'C2 H2 N6 O4' _chemical_formula_weight 174.10 _cell_length_a 8.3125(7) _cell_length_b 11.4102(8) _cell_length_c 13.5629(16) _cell_angle_alpha 78.074(8) _cell_angle_beta 77.335(8) _cell_angle_gamma 89.873(6) _cell_volume 1226.8(2) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3066 _cell_measurement_theta_min 4.2424 _cell_measurement_theta_max 32.2309 _cell_special_details ? _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.885 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.177 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9570 _exptl_absorpt_correction_T_max 0.9825 _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 9699 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.25 _diffrn_reflns_theta_max 26.49 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 5066 _reflns_number_gt 4379 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0791337000 _diffrn_orient_matrix_UB_12 0.0229526000 _diffrn_orient_matrix_UB_13 -0.0294427000 _diffrn_orient_matrix_UB_21 0.0204336000 _diffrn_orient_matrix_UB_22 0.0124658000 _diffrn_orient_matrix_UB_23 0.0450052000 _diffrn_orient_matrix_UB_31 0.0313790000 _diffrn_orient_matrix_UB_32 -0.0579892000 _diffrn_orient_matrix_UB_33 0.0107311000 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_Int_Tables_number 1 _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' 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' _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 0.254 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.047 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^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 difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(10) _refine_ls_number_reflns 5066 _refine_ls_number_parameters 913 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0769 _refine_ls_wR_factor_gt 0.0709 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 0.1059(4) 0.6272(2) 0.4123(2) 0.0406(7) Uani 1 1 d . . . O2 O -0.0607(3) 0.7133(2) 0.3197(2) 0.0369(7) Uani 1 1 d . . . O3 O 0.5932(4) 1.0713(2) 0.2259(2) 0.0433(7) Uani 1 1 d . . . O4 O 0.6353(4) 0.9042(3) 0.3241(2) 0.0428(7) Uani 1 1 d . . . N1 N 0.1453(4) 0.9202(2) 0.2609(2) 0.0242(6) Uani 1 1 d . . . N2 N 0.2777(4) 0.9956(2) 0.2384(2) 0.0247(6) Uani 1 1 d . . . N3 N 0.3295(4) 0.8151(2) 0.3316(2) 0.0254(7) Uani 1 1 d . . . N4 N 0.0660(4) 0.7102(3) 0.3524(2) 0.0265(7) Uani 1 1 d . . . N5 N 0.5488(4) 0.9718(3) 0.2771(2) 0.0312(7) Uani 1 1 d . . . N6 N 0.0048(4) 0.9620(3) 0.2251(3) 0.0321(7) Uani 1 1 d . . . H6A H -0.033(6) 0.907(4) 0.201(3) 0.038 Uiso 1 1 d . . . H6B H -0.072(6) 0.983(4) 0.272(4) 0.038 Uiso 1 1 d . . . C1 C 0.1804(4) 0.8139(3) 0.3160(3) 0.0222(7) Uani 1 1 d . . . C2 C 0.3832(4) 0.9261(3) 0.2835(3) 0.0256(8) Uani 1 1 d . . . O27 O 0.1735(3) -0.1039(2) 0.7253(2) 0.0352(6) Uani 1 1 d . . . O26 O 0.7459(4) 0.2199(2) 0.7529(3) 0.0449(8) Uani 1 1 d . . . O25 O 0.6548(4) 0.2241(2) 0.6132(2) 0.0438(7) Uani 1 1 d . . . O28 O 0.2243(3) -0.2373(2) 0.8529(2) 0.0278(6) Uani 1 1 d . . . N37 N 0.6109(4) -0.0150(2) 0.8243(2) 0.0221(6) Uani 1 1 d . . . N38 N 0.4987(4) -0.1082(2) 0.8505(2) 0.0225(6) Uani 1 1 d . . . N39 N 0.4365(4) 0.0363(2) 0.7225(2) 0.0243(6) Uani 1 1 d . . . N40 N 0.6641(4) 0.1797(3) 0.7014(3) 0.0322(8) Uani 1 1 d . . . N41 N 0.2553(4) -0.1428(2) 0.7888(2) 0.0231(6) Uani 1 1 d . . . N42 N 0.7470(4) -0.0256(3) 0.8713(3) 0.0335(8) Uani 1 1 d . . . H42A H 0.828(6) -0.022(4) 0.814(4) 0.040 Uiso 1 1 d . . . H42B H 0.750(6) 0.039(4) 0.891(3) 0.040 Uiso 1 1 d . . . C13 C 0.5694(4) 0.0676(3) 0.7497(3) 0.0236(7) Uani 1 1 d . . . C14 C 0.3995(4) -0.0703(3) 0.7874(3) 0.0208(7) Uani 1 1 d . . . O6 O 0.9911(3) 0.2185(2) 0.3194(2) 0.0364(7) Uani 1 1 d . . . O7 O 0.2816(4) 0.3831(3) 0.3311(2) 0.0448(7) Uani 1 1 d . . . O8 O 0.3764(4) 0.5561(2) 0.2368(2) 0.0397(7) Uani 1 1 d . . . O5 O 0.7621(3) 0.1245(2) 0.4076(2) 0.0402(7) Uani 1 1 d . . . N7 N 0.8141(3) 0.4229(2) 0.2638(2) 0.0218(6) Uani 1 1 d . . . N8 N 0.6905(4) 0.4947(2) 0.2449(2) 0.0238(6) Uani 1 1 d . . . N9 N 0.5872(4) 0.3107(2) 0.3389(2) 0.0228(6) Uani 1 1 d . . . N10 N 0.3942(4) 0.4570(3) 0.2865(2) 0.0301(7) Uani 1 1 d . . . N11 N 0.8429(4) 0.2117(2) 0.3516(2) 0.0245(6) Uani 1 1 d . . . N12 N 0.9778(4) 0.4677(3) 0.2259(3) 0.0298(7) Uani 1 1 d . . . H12A H 1.031(6) 0.458(4) 0.272(4) 0.036 Uiso 1 1 d . . . H12B H 1.017(5) 0.431(4) 0.181(3) 0.036 Uiso 1 1 d . . . C3 C 0.7483(4) 0.3145(3) 0.3195(3) 0.0210(7) Uani 1 1 d . . . C4 C 0.5606(4) 0.4210(3) 0.2917(3) 0.0230(7) Uani 1 1 d . . . O16 O 0.5892(3) 0.3445(2) 0.0995(2) 0.0352(6) Uani 1 1 d . . . O15 O 0.5557(3) 0.2237(3) 0.0005(2) 0.0388(7) Uani 1 1 d . . . O14 O 1.2619(3) 0.0493(2) 0.0011(2) 0.0343(6) Uani 1 1 d . . . O13 O 1.0811(3) -0.0126(2) -0.0724(2) 0.0412(7) Uani 1 1 d . . . N19 N 1.0450(3) 0.2207(2) 0.0643(2) 0.0207(6) Uani 1 1 d . . . N20 N 0.9087(3) 0.2827(2) 0.0862(2) 0.0224(6) Uani 1 1 d . . . N21 N 0.8635(4) 0.1452(2) -0.0057(2) 0.0236(6) Uani 1 1 d . . . N22 N 1.1287(4) 0.0528(2) -0.0227(2) 0.0261(7) Uani 1 1 d . . . N23 N 0.6371(4) 0.2699(3) 0.0481(2) 0.0268(7) Uani 1 1 d . . . N24 N 1.1857(4) 0.2509(3) 0.0971(3) 0.0272(7) Uani 1 1 d . . . H24A H 1.205(5) 0.192(4) 0.141(3) 0.033 Uiso 1 1 d . . . H24B H 1.272(6) 0.263(4) 0.047(3) 0.033 Uiso 1 1 d . . . C8 C 0.8069(4) 0.2319(3) 0.0425(3) 0.0224(7) Uani 1 1 d . . . C7 C 1.0138(4) 0.1399(3) 0.0103(3) 0.0225(7) Uani 1 1 d . . . O19 O 0.4661(3) 0.3977(2) 0.7219(2) 0.0358(6) Uani 1 1 d . . . O20 O 0.3272(3) 0.2647(2) 0.85044(19) 0.0296(6) Uani 1 1 d . . . O18 O -0.1252(4) 0.7234(2) 0.7540(3) 0.0439(7) Uani 1 1 d . . . O17 O 0.0629(4) 0.7273(2) 0.6132(2) 0.0420(7) Uani 1 1 d . . . N25 N -0.0390(3) 0.4878(2) 0.8241(2) 0.0222(6) Uani 1 1 d . . . N26 N 0.0551(3) 0.3949(2) 0.8496(2) 0.0223(6) Uani 1 1 d . . . N28 N -0.0086(4) 0.6828(3) 0.7020(3) 0.0308(7) Uani 1 1 d . . . N29 N 0.3411(4) 0.3592(2) 0.7868(2) 0.0234(6) Uani 1 1 d . . . N30 N -0.2082(4) 0.4786(3) 0.8709(3) 0.0362(8) Uani 1 1 d . . . H30A H -0.230(6) 0.549(4) 0.898(4) 0.043 Uiso 1 1 d . . . H30B H -0.266(6) 0.494(4) 0.817(4) 0.043 Uiso 1 1 d . . . N27 N 0.2064(4) 0.5391(2) 0.7216(2) 0.0240(6) Uani 1 1 d . . . C10 C 0.1978(4) 0.4323(3) 0.7859(3) 0.0201(7) Uani 1 1 d . . . C9 C 0.0536(4) 0.5704(3) 0.7493(3) 0.0232(7) Uani 1 1 d . . . O29 O 0.3034(4) 0.2629(2) 0.5829(3) 0.0457(8) Uani 1 1 d . . . O30 O 0.1132(4) 0.1934(3) 0.7219(2) 0.0463(8) Uani 1 1 d . . . O31 O -0.1401(3) -0.1426(2) 0.47346(19) 0.0288(6) Uani 1 1 d . . . O32 O -0.2837(3) -0.0758(2) 0.6021(2) 0.0358(6) Uani 1 1 d . . . N43 N 0.2222(4) 0.0656(2) 0.5069(2) 0.0224(6) Uani 1 1 d . . . N44 N 0.1295(4) -0.0131(2) 0.4781(2) 0.0228(6) Uani 1 1 d . . . N45 N -0.0255(4) 0.0650(2) 0.6078(2) 0.0245(6) Uani 1 1 d . . . N46 N 0.1861(4) 0.1958(3) 0.6332(3) 0.0335(8) Uani 1 1 d . . . N47 N -0.1558(4) -0.0807(2) 0.5384(2) 0.0232(6) Uani 1 1 d . . . N48 N 0.3913(4) 0.0791(3) 0.4614(3) 0.0328(7) Uani 1 1 d . . . H48B H 0.437(6) 0.068(4) 0.518(4) 0.039 Uiso 1 1 d . . . H48A H 0.407(5) 0.159(4) 0.436(3) 0.039 Uiso 1 1 d . . . C16 C -0.0142(4) -0.0087(3) 0.5410(3) 0.0206(7) Uani 1 1 d . . . C15 C 0.1272(4) 0.1098(3) 0.5821(3) 0.0242(8) Uani 1 1 d . . . O24 O 0.9549(3) 0.3568(2) 0.4763(2) 0.0299(6) Uani 1 1 d . . . O23 O 1.0060(3) 0.4237(2) 0.6054(2) 0.0353(6) Uani 1 1 d . . . O21 O 0.5298(4) 0.6994(3) 0.7192(2) 0.0429(7) Uani 1 1 d . . . O22 O 0.4360(3) 0.7663(2) 0.5802(3) 0.0430(7) Uani 1 1 d . . . N31 N 0.5715(4) 0.5681(2) 0.5063(2) 0.0223(6) Uani 1 1 d . . . N32 N 0.6834(4) 0.4874(2) 0.4798(2) 0.0229(6) Uani 1 1 d . . . N33 N 0.7476(4) 0.5676(2) 0.6076(2) 0.0248(6) Uani 1 1 d . . . N35 N 0.9255(4) 0.4195(2) 0.5411(2) 0.0244(6) Uani 1 1 d . . . N36 N 0.4333(4) 0.5814(3) 0.4614(3) 0.0328(7) Uani 1 1 d . . . H36B H 0.339(6) 0.569(4) 0.515(4) 0.039 Uiso 1 1 d . . . H36A H 0.432(5) 0.668(4) 0.428(3) 0.039 Uiso 1 1 d . . . N34 N 0.5182(4) 0.7000(3) 0.6310(3) 0.0331(8) Uani 1 1 d . . . C11 C 0.6147(4) 0.6130(3) 0.5812(3) 0.0229(7) Uani 1 1 d . . . C12 C 0.7825(4) 0.4932(3) 0.5420(3) 0.0199(7) Uani 1 1 d . . . O9 O 0.4300(3) 0.4999(2) -0.0838(2) 0.0361(7) Uani 1 1 d . . . O10 O 0.1935(3) 0.5418(2) 0.0036(2) 0.0360(6) Uani 1 1 d . . . O12 O 0.7679(4) 0.8507(3) 0.1137(2) 0.0488(8) Uani 1 1 d . . . O11 O 0.8835(4) 0.7267(3) 0.0209(3) 0.0484(8) Uani 1 1 d . . . N14 N 0.4662(4) 0.7859(3) 0.0905(2) 0.0254(7) Uani 1 1 d . . . N15 N 0.5896(3) 0.6482(2) 0.0009(2) 0.0238(6) Uani 1 1 d . . . N17 N 0.7633(4) 0.7744(3) 0.0633(3) 0.0331(8) Uani 1 1 d . . . N16 N 0.3441(4) 0.5550(2) -0.0255(2) 0.0247(6) Uani 1 1 d . . . N13 N 0.3522(3) 0.7229(2) 0.0639(2) 0.0226(6) Uani 1 1 d . . . N18 N 0.1855(4) 0.7459(3) 0.0956(3) 0.0300(7) Uani 1 1 d . . . H18A H 0.131(5) 0.670(4) 0.127(3) 0.036 Uiso 1 1 d . . . H18B H 0.153(6) 0.780(4) 0.046(4) 0.036 Uiso 1 1 d . . . C5 C 0.6037(4) 0.7367(3) 0.0500(3) 0.0259(8) Uani 1 1 d . . . C6 C 0.4287(4) 0.6425(3) 0.0111(3) 0.0229(7) 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 0.0360(17) 0.0284(14) 0.0490(19) 0.0051(13) -0.0041(13) -0.0003(12) O2 0.0350(17) 0.0329(14) 0.0441(18) -0.0092(13) -0.0106(13) -0.0069(12) O3 0.0450(19) 0.0401(16) 0.0376(18) 0.0031(14) -0.0044(14) -0.0177(13) O4 0.0299(16) 0.0519(18) 0.0479(19) -0.0071(15) -0.0148(14) 0.0064(13) N1 0.0293(17) 0.0211(14) 0.0227(16) -0.0047(12) -0.0069(13) 0.0020(12) N2 0.0257(16) 0.0223(14) 0.0250(17) -0.0032(12) -0.0048(13) -0.0024(12) N3 0.0273(18) 0.0250(15) 0.0224(16) -0.0056(13) -0.0016(13) 0.0025(12) N4 0.0259(17) 0.0214(15) 0.0279(17) -0.0037(13) 0.0013(13) -0.0003(12) N5 0.0253(18) 0.0391(19) 0.0275(18) -0.0090(15) -0.0008(14) -0.0033(14) N6 0.0275(19) 0.0338(18) 0.037(2) -0.0037(15) -0.0151(15) 0.0030(14) C1 0.0261(19) 0.0174(16) 0.0232(19) -0.0061(14) -0.0037(15) 0.0006(13) C2 0.025(2) 0.0289(19) 0.0232(19) -0.0083(15) -0.0044(15) -0.0013(15) O27 0.0349(16) 0.0363(15) 0.0377(17) -0.0031(12) -0.0196(13) -0.0026(12) O26 0.0325(17) 0.0279(14) 0.075(2) -0.0143(15) -0.0095(15) -0.0045(12) O25 0.0329(16) 0.0301(14) 0.055(2) 0.0095(14) 0.0008(14) 0.0040(12) O28 0.0293(14) 0.0236(12) 0.0281(14) -0.0031(11) -0.0032(11) -0.0029(10) N37 0.0230(16) 0.0221(14) 0.0217(16) -0.0088(12) -0.0023(12) -0.0004(11) N38 0.0239(16) 0.0216(14) 0.0239(16) -0.0092(12) -0.0050(12) 0.0002(11) N39 0.0221(16) 0.0211(14) 0.0276(17) -0.0042(12) -0.0023(13) 0.0034(11) N40 0.0216(17) 0.0201(15) 0.049(2) -0.0033(15) 0.0007(15) 0.0043(12) N41 0.0235(16) 0.0236(15) 0.0235(16) -0.0092(13) -0.0041(12) 0.0024(12) N42 0.031(2) 0.0366(19) 0.038(2) -0.0097(16) -0.0163(15) -0.0044(15) C13 0.0232(19) 0.0188(16) 0.0261(19) -0.0062(14) 0.0014(15) 0.0020(13) C14 0.0218(18) 0.0182(16) 0.0221(19) -0.0065(14) -0.0022(14) 0.0024(13) O6 0.0267(16) 0.0321(14) 0.0471(18) -0.0074(13) -0.0021(13) 0.0082(11) O7 0.0255(16) 0.0459(17) 0.057(2) 0.0044(15) -0.0114(14) -0.0035(13) O8 0.0402(18) 0.0406(16) 0.0328(16) 0.0048(13) -0.0083(13) 0.0150(13) O5 0.0377(17) 0.0265(14) 0.0517(19) 0.0075(13) -0.0147(14) -0.0016(12) N7 0.0216(16) 0.0231(14) 0.0209(16) -0.0083(12) -0.0017(12) 0.0000(11) N8 0.0276(17) 0.0214(14) 0.0213(16) -0.0021(12) -0.0054(13) 0.0010(12) N9 0.0249(16) 0.0216(14) 0.0239(16) -0.0063(12) -0.0084(13) -0.0004(12) N10 0.0326(19) 0.0339(17) 0.0264(18) -0.0073(14) -0.0111(15) 0.0052(14) N11 0.0246(17) 0.0225(15) 0.0283(17) -0.0082(13) -0.0076(13) 0.0011(12) N12 0.0248(18) 0.0280(17) 0.034(2) -0.0082(15) 0.0003(14) -0.0044(13) C3 0.0250(19) 0.0200(16) 0.0209(18) -0.0070(13) -0.0087(14) 0.0024(13) C4 0.0247(19) 0.0242(17) 0.0201(18) -0.0042(14) -0.0051(14) 0.0035(14) O16 0.0339(16) 0.0402(15) 0.0339(16) -0.0177(13) -0.0037(12) 0.0132(12) O15 0.0290(16) 0.0504(17) 0.0435(18) -0.0200(14) -0.0126(13) 0.0018(12) O14 0.0298(16) 0.0333(14) 0.0436(17) -0.0123(13) -0.0125(13) 0.0114(12) O13 0.0362(17) 0.0410(16) 0.0553(19) -0.0331(15) -0.0077(14) 0.0046(13) N19 0.0224(16) 0.0195(13) 0.0204(15) -0.0037(11) -0.0055(12) 0.0023(11) N20 0.0218(16) 0.0225(14) 0.0231(16) -0.0072(12) -0.0034(12) 0.0012(11) N21 0.0226(16) 0.0229(14) 0.0243(16) -0.0071(12) -0.0014(12) 0.0011(12) N22 0.0292(18) 0.0224(15) 0.0248(17) -0.0066(13) -0.0008(13) 0.0003(12) N23 0.0246(17) 0.0304(16) 0.0247(17) -0.0038(13) -0.0055(13) 0.0008(13) N24 0.0254(18) 0.0307(17) 0.0271(18) -0.0061(14) -0.0093(14) 0.0028(13) C8 0.0231(18) 0.0222(17) 0.0206(18) -0.0034(14) -0.0031(14) 0.0007(14) C7 0.0257(19) 0.0171(15) 0.0228(19) -0.0033(14) -0.0026(14) -0.0005(13) O19 0.0250(15) 0.0366(14) 0.0405(17) -0.0078(13) 0.0034(13) 0.0030(11) O20 0.0316(15) 0.0265(13) 0.0298(15) -0.0024(11) -0.0084(12) 0.0038(11) O18 0.0320(17) 0.0296(14) 0.074(2) -0.0159(15) -0.0166(15) 0.0096(12) O17 0.0462(18) 0.0314(15) 0.047(2) 0.0089(14) -0.0229(15) -0.0053(13) N25 0.0187(15) 0.0240(14) 0.0240(16) -0.0061(12) -0.0038(12) 0.0045(11) N26 0.0232(16) 0.0235(14) 0.0208(16) -0.0060(12) -0.0050(12) 0.0049(12) N28 0.0311(19) 0.0213(15) 0.044(2) -0.0028(15) -0.0212(16) 0.0004(13) N29 0.0249(17) 0.0231(15) 0.0233(16) -0.0078(13) -0.0051(13) 0.0005(12) N30 0.0242(19) 0.0361(19) 0.042(2) -0.0063(16) 0.0027(15) 0.0062(14) N27 0.0224(16) 0.0226(14) 0.0279(17) -0.0046(13) -0.0083(13) -0.0015(12) C10 0.0223(18) 0.0184(16) 0.0217(18) -0.0072(14) -0.0070(14) -0.0004(13) C9 0.028(2) 0.0173(16) 0.0278(19) -0.0058(14) -0.0117(15) -0.0006(13) O29 0.0373(18) 0.0289(14) 0.081(2) -0.0210(15) -0.0250(16) 0.0012(13) O30 0.0465(19) 0.0536(18) 0.057(2) -0.0378(17) -0.0257(16) 0.0208(15) O31 0.0326(15) 0.0283(13) 0.0291(15) -0.0115(12) -0.0094(11) 0.0013(11) O32 0.0261(15) 0.0413(15) 0.0360(17) -0.0108(13) 0.0039(12) -0.0058(12) N43 0.0240(16) 0.0204(14) 0.0227(16) -0.0045(12) -0.0052(12) -0.0020(11) N44 0.0267(16) 0.0186(13) 0.0215(16) -0.0008(12) -0.0050(12) -0.0026(11) N45 0.0274(17) 0.0236(14) 0.0278(17) -0.0098(13) -0.0132(13) 0.0080(12) N46 0.0309(19) 0.0310(18) 0.053(2) -0.0243(17) -0.0247(17) 0.0123(15) N47 0.0222(16) 0.0219(14) 0.0251(16) -0.0015(12) -0.0074(13) 0.0020(12) N48 0.0235(18) 0.0353(18) 0.035(2) -0.0054(16) 0.0013(14) -0.0072(14) C16 0.0255(19) 0.0179(16) 0.0190(18) -0.0033(13) -0.0069(14) 0.0024(13) C15 0.029(2) 0.0191(16) 0.030(2) -0.0096(15) -0.0144(16) 0.0057(14) O24 0.0264(14) 0.0307(13) 0.0342(15) -0.0139(12) -0.0033(11) 0.0044(11) O23 0.0365(16) 0.0387(15) 0.0373(16) -0.0121(13) -0.0185(13) 0.0081(12) O21 0.0356(16) 0.0472(17) 0.0478(19) -0.0304(15) 0.0059(13) -0.0047(13) O22 0.0277(16) 0.0291(14) 0.075(2) -0.0180(15) -0.0111(15) 0.0070(12) N31 0.0225(16) 0.0206(13) 0.0230(16) -0.0029(12) -0.0047(12) 0.0029(11) N32 0.0244(16) 0.0214(14) 0.0208(16) -0.0026(12) -0.0026(12) 0.0030(11) N33 0.0222(16) 0.0232(14) 0.0286(17) -0.0084(13) -0.0019(13) -0.0024(11) N35 0.0261(16) 0.0203(14) 0.0249(16) -0.0020(13) -0.0039(13) -0.0012(11) N36 0.0279(19) 0.0393(19) 0.034(2) -0.0081(15) -0.0129(15) 0.0087(14) N34 0.0221(18) 0.0278(17) 0.050(2) -0.0213(16) 0.0028(15) -0.0031(13) C11 0.0214(18) 0.0184(16) 0.028(2) -0.0070(14) -0.0012(15) -0.0034(13) C12 0.0209(18) 0.0171(16) 0.0200(18) -0.0032(13) -0.0015(14) -0.0005(12) O9 0.0348(16) 0.0400(16) 0.0416(17) -0.0256(14) -0.0096(13) 0.0073(12) O10 0.0268(16) 0.0347(14) 0.0440(18) -0.0106(13) -0.0005(12) -0.0060(11) O12 0.050(2) 0.0560(19) 0.051(2) -0.0224(16) -0.0212(15) -0.0096(15) O11 0.0250(16) 0.0577(19) 0.066(2) -0.0188(17) -0.0118(15) 0.0030(14) N14 0.0284(17) 0.0279(15) 0.0225(16) -0.0080(13) -0.0083(13) 0.0050(12) N15 0.0211(16) 0.0259(15) 0.0254(17) -0.0059(13) -0.0072(13) 0.0042(12) N17 0.0288(19) 0.0366(18) 0.037(2) -0.0065(16) -0.0155(15) -0.0036(14) N16 0.0251(17) 0.0209(15) 0.0281(17) -0.0043(13) -0.0068(13) 0.0005(12) N13 0.0216(16) 0.0251(15) 0.0209(16) -0.0057(12) -0.0040(12) 0.0043(12) N18 0.0222(18) 0.0361(18) 0.0305(19) -0.0078(15) -0.0027(14) 0.0080(14) C5 0.0240(19) 0.0258(18) 0.028(2) -0.0039(15) -0.0075(15) 0.0001(14) C6 0.0265(19) 0.0206(16) 0.0222(19) -0.0042(14) -0.0072(15) 0.0017(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 O1 N4 1.211(4) . ? O2 N4 1.227(4) . ? O3 N5 1.213(4) . ? O4 N5 1.230(4) . ? N1 N2 1.339(4) . ? N1 C1 1.354(4) . ? N1 N6 1.406(4) . ? N2 C2 1.343(5) . ? N3 C1 1.303(5) . ? N3 C2 1.327(5) . ? N4 C1 1.452(4) . ? N5 C2 1.451(5) . ? N6 H6A 0.85(4) . ? N6 H6B 0.87(5) . ? O27 N41 1.224(4) . ? O26 N40 1.226(4) . ? O25 N40 1.218(4) . ? O28 N41 1.225(4) . ? N37 C13 1.337(5) . ? N37 N38 1.353(4) . ? N37 N42 1.409(4) . ? N38 C14 1.325(4) . ? N39 C13 1.311(5) . ? N39 C14 1.338(4) . ? N40 C13 1.455(5) . ? N41 C14 1.453(4) . ? N42 H42A 0.91(5) . ? N42 H42B 0.84(5) . ? O6 N11 1.211(4) . ? O7 N10 1.224(4) . ? O8 N10 1.218(4) . ? O5 N11 1.219(4) . ? N7 N8 1.348(4) . ? N7 C3 1.355(4) . ? N7 N12 1.402(4) . ? N8 C4 1.326(5) . ? N9 C3 1.306(4) . ? N9 C4 1.331(4) . ? N10 C4 1.454(5) . ? N11 C3 1.456(4) . ? N12 H12A 0.83(5) . ? N12 H12B 0.82(4) . ? O16 N23 1.222(4) . ? O15 N23 1.219(4) . ? O14 N22 1.218(4) . ? O13 N22 1.221(4) . ? N19 N20 1.344(4) . ? N19 C7 1.348(4) . ? N19 N24 1.406(4) . ? N20 C8 1.329(4) . ? N21 C7 1.313(5) . ? N21 C8 1.326(4) . ? N22 C7 1.447(4) . ? N23 C8 1.467(4) . ? N24 H24A 0.84(4) . ? N24 H24B 0.86(4) . ? O19 N29 1.220(4) . ? O20 N29 1.222(4) . ? O18 N28 1.219(4) . ? O17 N28 1.224(4) . ? N25 C9 1.332(5) . ? N25 N26 1.348(4) . ? N25 N30 1.405(4) . ? N26 C10 1.317(4) . ? N28 C9 1.458(4) . ? N29 C10 1.453(4) . ? N30 H30A 0.96(5) . ? N30 H30B 0.95(5) . ? N27 C9 1.314(5) . ? N27 C10 1.336(4) . ? O29 N46 1.224(4) . ? O30 N46 1.218(4) . ? O31 N47 1.223(4) . ? O32 N47 1.224(4) . ? N43 C15 1.332(4) . ? N43 N44 1.354(4) . ? N43 N48 1.401(4) . ? N44 C16 1.315(4) . ? N45 C15 1.315(5) . ? N45 C16 1.347(4) . ? N46 C15 1.454(4) . ? N47 C16 1.447(4) . ? N48 H48B 0.91(5) . ? N48 H48A 0.91(4) . ? O24 N35 1.228(4) . ? O23 N35 1.219(4) . ? O21 N34 1.220(4) . ? O22 N34 1.226(4) . ? N31 C11 1.342(4) . ? N31 N32 1.352(4) . ? N31 N36 1.407(4) . ? N32 C12 1.313(4) . ? N33 C11 1.308(5) . ? N33 C12 1.339(4) . ? N35 C12 1.453(4) . ? N36 H36B 0.93(5) . ? N36 H36A 1.00(5) . ? N34 C11 1.456(4) . ? O9 N16 1.220(4) . ? O10 N16 1.227(4) . ? O12 N17 1.218(4) . ? O11 N17 1.225(4) . ? N14 C5 1.331(5) . ? N14 N13 1.343(4) . ? N15 C6 1.314(5) . ? N15 C5 1.337(4) . ? N17 C5 1.455(5) . ? N16 C6 1.448(4) . ? N13 C6 1.353(4) . ? N13 N18 1.399(4) . ? N18 H18A 0.95(4) . ? N18 H18B 0.81(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 N2 N1 C1 108.7(3) . . ? N2 N1 N6 118.0(3) . . ? C1 N1 N6 133.3(3) . . ? N1 N2 C2 101.0(3) . . ? C1 N3 C2 101.1(3) . . ? O1 N4 O2 125.8(3) . . ? O1 N4 C1 116.3(3) . . ? O2 N4 C1 117.9(3) . . ? O3 N5 O4 124.7(3) . . ? O3 N5 C2 118.9(3) . . ? O4 N5 C2 116.3(3) . . ? N1 N6 H6A 108(3) . . ? N1 N6 H6B 114(3) . . ? H6A N6 H6B 110(4) . . ? N3 C1 N1 112.2(3) . . ? N3 C1 N4 123.9(3) . . ? N1 C1 N4 124.0(3) . . ? N4 C1 C2 163.7(3) . . ? N3 C2 N2 117.0(3) . . ? N3 C2 N5 122.6(3) . . ? N2 C2 N5 120.4(3) . . ? N5 C2 C1 161.6(3) . . ? C13 N37 N38 108.4(3) . . ? C13 N37 N42 133.5(3) . . ? N38 N37 N42 118.0(3) . . ? C14 N38 N37 100.8(3) . . ? C13 N39 C14 99.6(3) . . ? O25 N40 O26 126.4(3) . . ? O25 N40 C13 116.5(3) . . ? O26 N40 C13 117.1(3) . . ? O27 N41 O28 125.0(3) . . ? O27 N41 C14 116.9(3) . . ? O28 N41 C14 118.1(3) . . ? N37 N42 H42A 98(3) . . ? N37 N42 H42B 103(3) . . ? H42A N42 H42B 109(4) . . ? N39 C13 N37 113.2(3) . . ? N39 C13 N40 123.1(3) . . ? N37 C13 N40 123.6(3) . . ? N40 C13 C14 163.8(3) . . ? N38 C14 N39 118.0(3) . . ? N38 C14 N41 120.8(3) . . ? N39 C14 N41 121.2(3) . . ? N41 C14 C13 160.9(3) . . ? N8 N7 C3 108.8(3) . . ? N8 N7 N12 119.2(3) . . ? C3 N7 N12 132.0(3) . . ? C4 N8 N7 100.5(3) . . ? C3 N9 C4 100.5(3) . . ? O8 N10 O7 124.6(3) . . ? O8 N10 C4 118.5(3) . . ? O7 N10 C4 116.8(3) . . ? O6 N11 O5 126.1(3) . . ? O6 N11 C3 118.4(3) . . ? O5 N11 C3 115.5(3) . . ? N7 N12 H12A 112(3) . . ? N7 N12 H12B 105(3) . . ? H12A N12 H12B 111(4) . . ? N9 C3 N7 112.0(3) . . ? N9 C3 N11 122.9(3) . . ? N7 C3 N11 125.1(3) . . ? N11 C3 C4 163.0(3) . . ? N8 C4 N9 118.1(3) . . ? N8 C4 N10 121.1(3) . . ? N9 C4 N10 120.7(3) . . ? N10 C4 C3 159.7(3) . . ? N20 N19 C7 108.4(3) . . ? N20 N19 N24 118.3(3) . . ? C7 N19 N24 133.3(3) . . ? C8 N20 N19 101.1(3) . . ? C7 N21 C8 100.3(3) . . ? O14 N22 O13 125.5(3) . . ? O14 N22 C7 118.7(3) . . ? O13 N22 C7 115.9(3) . . ? O15 N23 O16 125.7(3) . . ? O15 N23 C8 116.6(3) . . ? O16 N23 C8 117.7(3) . . ? N19 N24 H24A 108(3) . . ? N19 N24 H24B 112(3) . . ? H24A N24 H24B 106(4) . . ? N21 C8 N20 117.8(3) . . ? N21 C8 N23 121.0(3) . . ? N20 C8 N23 121.1(3) . . ? N23 C8 C7 160.6(3) . . ? N21 C7 N19 112.4(3) . . ? N21 C7 N22 123.1(3) . . ? N19 C7 N22 124.5(3) . . ? N22 C7 C8 163.0(3) . . ? C9 N25 N26 108.7(3) . . ? C9 N25 N30 132.4(3) . . ? N26 N25 N30 118.7(3) . . ? C10 N26 N25 100.9(3) . . ? O18 N28 O17 126.4(3) . . ? O18 N28 C9 117.5(3) . . ? O17 N28 C9 116.1(3) . . ? O19 N29 O20 125.4(3) . . ? O19 N29 C10 116.3(3) . . ? O20 N29 C10 118.3(3) . . ? N25 N30 H30A 106(3) . . ? N25 N30 H30B 107(3) . . ? H30A N30 H30B 100(4) . . ? C9 N27 C10 99.6(3) . . ? N26 C10 N27 118.0(3) . . ? N26 C10 N29 120.6(3) . . ? N27 C10 N29 121.4(3) . . ? N29 C10 C9 161.2(3) . . ? N27 C9 N25 112.8(3) . . ? N27 C9 N28 123.5(3) . . ? N25 C9 N28 123.6(3) . . ? N28 C9 C10 164.1(3) . . ? C15 N43 N44 108.6(3) . . ? C15 N43 N48 133.0(3) . . ? N44 N43 N48 118.2(3) . . ? C16 N44 N43 101.1(3) . . ? C15 N45 C16 99.5(3) . . ? O30 N46 O29 126.7(3) . . ? O30 N46 C15 116.4(3) . . ? O29 N46 C15 116.9(3) . . ? O31 N47 O32 124.3(3) . . ? O31 N47 C16 118.3(3) . . ? O32 N47 C16 117.4(3) . . ? N43 N48 H48B 102(3) . . ? N43 N48 H48A 103(3) . . ? H48B N48 H48A 103(4) . . ? N44 C16 N45 117.8(3) . . ? N44 C16 N47 121.0(3) . . ? N45 C16 N47 121.1(3) . . ? N47 C16 C15 160.8(3) . . ? N45 C15 N43 113.0(3) . . ? N45 C15 N46 123.0(3) . . ? N43 C15 N46 123.9(3) . . ? N46 C15 C16 163.9(3) . . ? C11 N31 N32 107.8(3) . . ? C11 N31 N36 133.1(3) . . ? N32 N31 N36 118.8(3) . . ? C12 N32 N31 101.1(3) . . ? C11 N33 C12 99.2(3) . . ? O23 N35 O24 125.0(3) . . ? O23 N35 C12 117.5(3) . . ? O24 N35 C12 117.5(3) . . ? N31 N36 H36B 108(3) . . ? N31 N36 H36A 107(3) . . ? H36B N36 H36A 104(3) . . ? O21 N34 O22 127.0(3) . . ? O21 N34 C11 115.8(3) . . ? O22 N34 C11 117.1(3) . . ? N33 C11 N31 113.5(3) . . ? N33 C11 N34 123.6(3) . . ? N31 C11 N34 122.9(3) . . ? N34 C11 C12 164.5(3) . . ? N32 C12 N33 118.4(3) . . ? N32 C12 N35 121.0(3) . . ? N33 C12 N35 120.6(3) . . ? N35 C12 C11 160.4(3) . . ? C5 N14 N13 100.8(3) . . ? C6 N15 C5 100.0(3) . . ? O12 N17 O11 125.3(3) . . ? O12 N17 C5 118.5(3) . . ? O11 N17 C5 116.2(3) . . ? O9 N16 O10 125.0(3) . . ? O9 N16 C6 116.5(3) . . ? O10 N16 C6 118.5(3) . . ? N14 N13 C6 108.9(3) . . ? N14 N13 N18 118.9(3) . . ? C6 N13 N18 132.1(3) . . ? N13 N18 H18A 106(2) . . ? N13 N18 H18B 109(3) . . ? H18A N18 H18B 113(4) . . ? N14 C5 N15 118.0(3) . . ? N14 C5 N17 120.7(3) . . ? N15 C5 N17 121.2(3) . . ? N17 C5 C6 160.7(3) . . ? N15 C6 N13 112.3(3) . . ? N15 C6 N16 123.2(3) . . ? N13 C6 N16 124.4(3) . . ? N16 C6 C5 163.5(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 C2 -0.2(3) . . . . ? N6 N1 N2 C2 -179.8(3) . . . . ? C2 N3 C1 N1 -0.2(4) . . . . ? C2 N3 C1 N4 179.1(3) . . . . ? N2 N1 C1 N3 0.2(4) . . . . ? N6 N1 C1 N3 179.7(3) . . . . ? N2 N1 C1 N4 -179.1(3) . . . . ? N6 N1 C1 N4 0.5(6) . . . . ? N2 N1 C1 C2 0.1(2) . . . . ? N6 N1 C1 C2 179.6(4) . . . . ? O1 N4 C1 N3 10.5(5) . . . . ? O2 N4 C1 N3 -168.9(3) . . . . ? O1 N4 C1 N1 -170.3(3) . . . . ? O2 N4 C1 N1 10.3(5) . . . . ? O1 N4 C1 C2 12.5(11) . . . . ? O2 N4 C1 C2 -166.9(8) . . . . ? C1 N3 C2 N2 0.0(4) . . . . ? C1 N3 C2 N5 -178.8(3) . . . . ? N1 N2 C2 N3 0.1(4) . . . . ? N1 N2 C2 N5 178.9(3) . . . . ? N1 N2 C2 C1 0.1(2) . . . . ? O3 N5 C2 N3 174.9(3) . . . . ? O4 N5 C2 N3 -4.1(5) . . . . ? O3 N5 C2 N2 -3.8(5) . . . . ? O4 N5 C2 N2 177.1(3) . . . . ? O3 N5 C2 C1 172.5(7) . . . . ? O4 N5 C2 C1 -6.6(10) . . . . ? N1 C1 C2 N3 179.9(4) . . . . ? N4 C1 C2 N3 -2.6(9) . . . . ? N3 C1 C2 N2 -180.0(4) . . . . ? N1 C1 C2 N2 -0.1(2) . . . . ? N4 C1 C2 N2 177.5(9) . . . . ? N3 C1 C2 N5 3.3(8) . . . . ? N1 C1 C2 N5 -176.9(9) . . . . ? N4 C1 C2 N5 0.7(15) . . . . ? C13 N37 N38 C14 -0.1(3) . . . . ? N42 N37 N38 C14 -175.7(3) . . . . ? C14 N39 C13 N37 1.0(4) . . . . ? C14 N39 C13 N40 179.5(3) . . . . ? N38 N37 C13 N39 -0.6(4) . . . . ? N42 N37 C13 N39 174.0(3) . . . . ? N38 N37 C13 N40 -179.0(3) . . . . ? N42 N37 C13 N40 -4.5(6) . . . . ? N38 N37 C13 C14 0.1(2) . . . . ? N42 N37 C13 C14 174.7(4) . . . . ? O25 N40 C13 N39 -25.5(5) . . . . ? O26 N40 C13 N39 154.9(3) . . . . ? O25 N40 C13 N37 152.8(3) . . . . ? O26 N40 C13 N37 -26.8(5) . . . . ? O25 N40 C13 C14 -24.2(11) . . . . ? O26 N40 C13 C14 156.1(8) . . . . ? N37 N38 C14 N39 0.9(4) . . . . ? N37 N38 C14 N41 -179.4(3) . . . . ? N37 N38 C14 C13 0.1(2) . . . . ? C13 N39 C14 N38 -1.2(4) . . . . ? C13 N39 C14 N41 179.0(3) . . . . ? O27 N41 C14 N38 -177.1(3) . . . . ? O28 N41 C14 N38 3.2(4) . . . . ? O27 N41 C14 N39 2.6(4) . . . . ? O28 N41 C14 N39 -177.0(3) . . . . ? O27 N41 C14 C13 4.5(9) . . . . ? O28 N41 C14 C13 -175.2(7) . . . . ? N39 C13 C14 N38 178.9(4) . . . . ? N37 C13 C14 N38 -0.1(2) . . . . ? N40 C13 C14 N38 177.4(9) . . . . ? N37 C13 C14 N39 -179.0(4) . . . . ? N40 C13 C14 N39 -1.6(9) . . . . ? N39 C13 C14 N41 -2.5(8) . . . . ? N37 C13 C14 N41 178.4(8) . . . . ? N40 C13 C14 N41 -4.1(15) . . . . ? C3 N7 N8 C4 -0.1(3) . . . . ? N12 N7 N8 C4 179.7(3) . . . . ? C4 N9 C3 N7 0.4(4) . . . . ? C4 N9 C3 N11 -177.5(3) . . . . ? N8 N7 C3 N9 -0.2(4) . . . . ? N12 N7 C3 N9 180.0(3) . . . . ? N8 N7 C3 N11 177.6(3) . . . . ? N12 N7 C3 N11 -2.2(5) . . . . ? N8 N7 C3 C4 0.1(2) . . . . ? N12 N7 C3 C4 -179.7(4) . . . . ? O6 N11 C3 N9 170.8(3) . . . . ? O5 N11 C3 N9 -7.4(5) . . . . ? O6 N11 C3 N7 -6.8(5) . . . . ? O5 N11 C3 N7 174.9(3) . . . . ? O6 N11 C3 C4 165.3(8) . . . . ? O5 N11 C3 C4 -13.0(11) . . . . ? N7 N8 C4 N9 0.4(4) . . . . ? N7 N8 C4 N10 -176.0(3) . . . . ? N7 N8 C4 C3 0.1(2) . . . . ? C3 N9 C4 N8 -0.6(4) . . . . ? C3 N9 C4 N10 175.9(3) . . . . ? O8 N10 C4 N8 1.1(5) . . . . ? O7 N10 C4 N8 179.4(3) . . . . ? O8 N10 C4 N9 -175.2(3) . . . . ? O7 N10 C4 N9 3.0(5) . . . . ? O8 N10 C4 C3 -167.6(6) . . . . ? O7 N10 C4 C3 10.6(9) . . . . ? N9 C3 C4 N8 179.5(4) . . . . ? N7 C3 C4 N8 -0.1(2) . . . . ? N11 C3 C4 N8 -173.3(9) . . . . ? N7 C3 C4 N9 -179.6(3) . . . . ? N11 C3 C4 N9 7.3(9) . . . . ? N9 C3 C4 N10 -10.3(7) . . . . ? N7 C3 C4 N10 170.1(8) . . . . ? N11 C3 C4 N10 -3.1(15) . . . . ? C7 N19 N20 C8 0.2(4) . . . . ? N24 N19 N20 C8 178.8(3) . . . . ? C7 N21 C8 N20 0.9(4) . . . . ? C7 N21 C8 N23 -178.7(3) . . . . ? N19 N20 C8 N21 -0.7(4) . . . . ? N19 N20 C8 N23 178.9(3) . . . . ? N19 N20 C8 C7 -0.1(2) . . . . ? O15 N23 C8 N21 -4.8(5) . . . . ? O16 N23 C8 N21 175.2(3) . . . . ? O15 N23 C8 N20 175.6(3) . . . . ? O16 N23 C8 N20 -4.5(5) . . . . ? O15 N23 C8 C7 -7.3(10) . . . . ? O16 N23 C8 C7 172.7(7) . . . . ? C8 N21 C7 N19 -0.7(4) . . . . ? C8 N21 C7 N22 176.6(3) . . . . ? N20 N19 C7 N21 0.4(4) . . . . ? N24 N19 C7 N21 -178.0(3) . . . . ? N20 N19 C7 N22 -176.9(3) . . . . ? N24 N19 C7 N22 4.7(6) . . . . ? N20 N19 C7 C8 -0.1(2) . . . . ? N24 N19 C7 C8 -178.5(4) . . . . ? O14 N22 C7 N21 -175.3(3) . . . . ? O13 N22 C7 N21 4.0(5) . . . . ? O14 N22 C7 N19 1.7(5) . . . . ? O13 N22 C7 N19 -179.0(3) . . . . ? O14 N22 C7 C8 -167.8(8) . . . . ? O13 N22 C7 C8 11.5(11) . . . . ? N20 C8 C7 N21 -179.2(4) . . . . ? N23 C8 C7 N21 3.3(8) . . . . ? N21 C8 C7 N19 179.3(4) . . . . ? N20 C8 C7 N19 0.1(2) . . . . ? N23 C8 C7 N19 -177.4(8) . . . . ? N21 C8 C7 N22 -9.8(9) . . . . ? N20 C8 C7 N22 171.0(10) . . . . ? N23 C8 C7 N22 -6.5(16) . . . . ? C9 N25 N26 C10 0.0(3) . . . . ? N30 N25 N26 C10 175.3(3) . . . . ? N25 N26 C10 N27 -0.2(4) . . . . ? N25 N26 C10 N29 179.3(3) . . . . ? N25 N26 C10 C9 0.0(2) . . . . ? C9 N27 C10 N26 0.3(4) . . . . ? C9 N27 C10 N29 -179.2(3) . . . . ? O19 N29 C10 N26 176.5(3) . . . . ? O20 N29 C10 N26 -2.7(4) . . . . ? O19 N29 C10 N27 -3.9(4) . . . . ? O20 N29 C10 N27 176.8(3) . . . . ? O19 N29 C10 C9 -5.6(9) . . . . ? O20 N29 C10 C9 175.2(7) . . . . ? C10 N27 C9 N25 -0.3(4) . . . . ? C10 N27 C9 N28 -179.5(3) . . . . ? N26 N25 C9 N27 0.2(4) . . . . ? N30 N25 C9 N27 -174.3(3) . . . . ? N26 N25 C9 N28 179.4(3) . . . . ? N30 N25 C9 N28 5.0(6) . . . . ? N26 N25 C9 C10 0.0(2) . . . . ? N30 N25 C9 C10 -174.5(4) . . . . ? O18 N28 C9 N27 -153.8(3) . . . . ? O17 N28 C9 N27 26.1(5) . . . . ? O18 N28 C9 N25 27.0(5) . . . . ? O17 N28 C9 N25 -153.1(3) . . . . ? O18 N28 C9 C10 -155.0(8) . . . . ? O17 N28 C9 C10 24.9(11) . . . . ? N26 C10 C9 N27 -179.7(3) . . . . ? N29 C10 C9 N27 2.1(8) . . . . ? N26 C10 C9 N25 0.0(2) . . . . ? N27 C10 C9 N25 179.7(4) . . . . ? N29 C10 C9 N25 -178.2(8) . . . . ? N26 C10 C9 N28 -178.3(9) . . . . ? N27 C10 C9 N28 1.4(9) . . . . ? N29 C10 C9 N28 3.6(15) . . . . ? C15 N43 N44 C16 -0.6(3) . . . . ? N48 N43 N44 C16 175.2(3) . . . . ? N43 N44 C16 N45 0.2(4) . . . . ? N43 N44 C16 N47 -179.9(3) . . . . ? N43 N44 C16 C15 0.4(2) . . . . ? C15 N45 C16 N44 0.2(4) . . . . ? C15 N45 C16 N47 -179.7(3) . . . . ? O31 N47 C16 N44 -2.7(4) . . . . ? O32 N47 C16 N44 177.0(3) . . . . ? O31 N47 C16 N45 177.2(3) . . . . ? O32 N47 C16 N45 -3.1(4) . . . . ? O31 N47 C16 C15 176.6(7) . . . . ? O32 N47 C16 C15 -3.7(9) . . . . ? C16 N45 C15 N43 -0.6(4) . . . . ? C16 N45 C15 N46 -178.8(3) . . . . ? N44 N43 C15 N45 0.8(4) . . . . ? N48 N43 C15 N45 -174.1(4) . . . . ? N44 N43 C15 N46 179.0(3) . . . . ? N48 N43 C15 N46 4.1(6) . . . . ? N44 N43 C15 C16 0.4(2) . . . . ? N48 N43 C15 C16 -174.5(4) . . . . ? O30 N46 C15 N45 26.1(5) . . . . ? O29 N46 C15 N45 -154.0(3) . . . . ? O30 N46 C15 N43 -152.0(3) . . . . ? O29 N46 C15 N43 27.9(5) . . . . ? O30 N46 C15 C16 23.3(11) . . . . ? O29 N46 C15 C16 -156.8(9) . . . . ? N44 C16 C15 N45 -179.8(3) . . . . ? N47 C16 C15 N45 0.8(8) . . . . ? N44 C16 C15 N43 -0.4(2) . . . . ? N45 C16 C15 N43 179.5(4) . . . . ? N47 C16 C15 N43 -179.7(8) . . . . ? N44 C16 C15 N46 -176.2(10) . . . . ? N45 C16 C15 N46 3.6(9) . . . . ? N47 C16 C15 N46 4.4(15) . . . . ? C11 N31 N32 C12 -0.2(3) . . . . ? N36 N31 N32 C12 -174.8(3) . . . . ? C12 N33 C11 N31 0.8(4) . . . . ? C12 N33 C11 N34 178.2(3) . . . . ? N32 N31 C11 N33 -0.4(4) . . . . ? N36 N31 C11 N33 173.1(4) . . . . ? N32 N31 C11 N34 -177.8(3) . . . . ? N36 N31 C11 N34 -4.3(6) . . . . ? N32 N31 C11 C12 0.1(2) . . . . ? N36 N31 C11 C12 173.6(4) . . . . ? O21 N34 C11 N33 -24.3(5) . . . . ? O22 N34 C11 N33 154.9(3) . . . . ? O21 N34 C11 N31 152.9(3) . . . . ? O22 N34 C11 N31 -27.9(5) . . . . ? O21 N34 C11 C12 -19.8(12) . . . . ? O22 N34 C11 C12 159.4(9) . . . . ? N31 N32 C12 N33 0.7(4) . . . . ? N31 N32 C12 N35 180.0(3) . . . . ? N31 N32 C12 C11 0.1(2) . . . . ? C11 N33 C12 N32 -1.0(4) . . . . ? C11 N33 C12 N35 179.8(3) . . . . ? O23 N35 C12 N32 -175.4(3) . . . . ? O24 N35 C12 N32 3.8(5) . . . . ? O23 N35 C12 N33 3.8(5) . . . . ? O24 N35 C12 N33 -177.0(3) . . . . ? O23 N35 C12 C11 4.1(9) . . . . ? O24 N35 C12 C11 -176.7(7) . . . . ? N33 C11 C12 N32 179.1(4) . . . . ? N31 C11 C12 N32 -0.1(2) . . . . ? N34 C11 C12 N32 173.5(10) . . . . ? N31 C11 C12 N33 -179.3(4) . . . . ? N34 C11 C12 N33 -5.7(10) . . . . ? N33 C11 C12 N35 -0.4(8) . . . . ? N31 C11 C12 N35 -179.7(8) . . . . ? N34 C11 C12 N35 -6.1(16) . . . . ? C5 N14 N13 C6 0.2(4) . . . . ? C5 N14 N13 N18 178.2(3) . . . . ? N13 N14 C5 N15 -0.5(4) . . . . ? N13 N14 C5 N17 -177.6(3) . . . . ? N13 N14 C5 C6 -0.2(2) . . . . ? C6 N15 C5 N14 0.5(4) . . . . ? C6 N15 C5 N17 177.6(3) . . . . ? O12 N17 C5 N14 1.1(5) . . . . ? O11 N17 C5 N14 -178.0(3) . . . . ? O12 N17 C5 N15 -175.8(3) . . . . ? O11 N17 C5 N15 5.0(5) . . . . ? O12 N17 C5 C6 -171.2(7) . . . . ? O11 N17 C5 C6 9.6(11) . . . . ? C5 N15 C6 N13 -0.4(4) . . . . ? C5 N15 C6 N16 -177.2(3) . . . . ? N14 N13 C6 N15 0.1(4) . . . . ? N18 N13 C6 N15 -177.6(3) . . . . ? N14 N13 C6 N16 176.8(3) . . . . ? N18 N13 C6 N16 -0.8(6) . . . . ? N14 N13 C6 C5 -0.2(2) . . . . ? N18 N13 C6 C5 -177.8(4) . . . . ? O9 N16 C6 N15 -13.3(5) . . . . ? O10 N16 C6 N15 166.8(3) . . . . ? O9 N16 C6 N13 170.3(3) . . . . ? O10 N16 C6 N13 -9.6(5) . . . . ? O9 N16 C6 C5 -19.8(11) . . . . ? O10 N16 C6 C5 160.3(9) . . . . ? N14 C5 C6 N15 -179.5(4) . . . . ? N17 C5 C6 N15 -6.2(9) . . . . ? N14 C5 C6 N13 0.2(2) . . . . ? N15 C5 C6 N13 179.7(4) . . . . ? N17 C5 C6 N13 173.5(9) . . . . ? N14 C5 C6 N16 -171.1(10) . . . . ? N15 C5 C6 N16 8.4(10) . . . . ? N17 C5 C6 N16 2.2(17) . . . . ? 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 ? ? ? ? ? ? ? ? _geom_special_details ? _iucr_refine_instructions_details ; TITL v2 in P1 CELL 0.71073 8.3125 11.4102 13.5629 78.074 77.335 89.873 ZERR 8.00 0.0007 0.0008 0.0016 0.008 0.008 0.006 LATT -1 SFAC C H N O UNIT 16 16 48 32 MERG 3 OMIT -2.00 53.00 FMAP 2 SIZE 0.10 0.20 0.25 ACTA HTAB 2.00000 BOND $H CONF L.S. 8 TEMP -100.00 WGHT 0.036800 FVAR 0.18265 O1 4 0.105928 0.627197 0.412305 11.00000 0.03597 0.02844 = 0.04901 0.00507 -0.00415 -0.00032 O2 4 -0.060730 0.713264 0.319706 11.00000 0.03500 0.03291 = 0.04410 -0.00923 -0.01060 -0.00693 O3 4 0.593200 1.071294 0.225928 11.00000 0.04502 0.04010 = 0.03761 0.00311 -0.00438 -0.01775 O4 4 0.635271 0.904164 0.324091 11.00000 0.02993 0.05192 = 0.04788 -0.00711 -0.01475 0.00640 N1 3 0.145320 0.920217 0.260872 11.00000 0.02926 0.02106 = 0.02266 -0.00466 -0.00689 0.00201 N2 3 0.277721 0.995637 0.238415 11.00000 0.02573 0.02228 = 0.02501 -0.00315 -0.00477 -0.00238 N3 3 0.329537 0.815134 0.331555 11.00000 0.02725 0.02501 = 0.02236 -0.00557 -0.00158 0.00250 N4 3 0.065999 0.710164 0.352383 11.00000 0.02594 0.02142 = 0.02790 -0.00372 0.00134 -0.00032 N5 3 0.548816 0.971763 0.277133 11.00000 0.02533 0.03913 = 0.02750 -0.00897 -0.00085 -0.00331 N6 3 0.004814 0.962022 0.225078 11.00000 0.02747 0.03379 = 0.03700 -0.00371 -0.01514 0.00302 H6A 2 -0.032560 0.906697 0.201195 11.00000 -1.20000 H6B 2 -0.071954 0.982919 0.271925 11.00000 -1.20000 C1 1 0.180425 0.813933 0.315970 11.00000 0.02609 0.01736 = 0.02319 -0.00614 -0.00368 0.00057 C2 1 0.383230 0.926112 0.283531 11.00000 0.02547 0.02887 = 0.02317 -0.00832 -0.00438 -0.00132 O27 4 0.173533 -0.103860 0.725313 11.00000 0.03489 0.03632 = 0.03766 -0.00305 -0.01962 -0.00262 O26 4 0.745933 0.219877 0.752921 11.00000 0.03255 0.02794 = 0.07473 -0.01431 -0.00946 -0.00449 O25 4 0.654758 0.224111 0.613208 11.00000 0.03286 0.03005 = 0.05522 0.00954 0.00084 0.00402 O28 4 0.224278 -0.237285 0.852871 11.00000 0.02931 0.02357 = 0.02806 -0.00312 -0.00317 -0.00292 N37 3 0.610878 -0.014996 0.824316 11.00000 0.02303 0.02214 = 0.02174 -0.00876 -0.00227 -0.00036 N38 3 0.498689 -0.108231 0.850543 11.00000 0.02394 0.02160 = 0.02391 -0.00925 -0.00499 0.00023 N39 3 0.436495 0.036322 0.722516 11.00000 0.02210 0.02111 = 0.02764 -0.00417 -0.00226 0.00339 N40 3 0.664106 0.179710 0.701427 11.00000 0.02159 0.02010 = 0.04895 -0.00330 0.00069 0.00433 N41 3 0.255341 -0.142833 0.788766 11.00000 0.02352 0.02360 = 0.02351 -0.00921 -0.00413 0.00240 N42 3 0.747025 -0.025578 0.871284 11.00000 0.03099 0.03659 = 0.03784 -0.00969 -0.01629 -0.00445 H42A 2 0.827987 -0.022128 0.813561 11.00000 -1.20000 H42B 2 0.749923 0.038825 0.891407 11.00000 -1.20000 C13 1 0.569389 0.067631 0.749728 11.00000 0.02321 0.01882 = 0.02608 -0.00624 0.00137 0.00197 C14 1 0.399514 -0.070271 0.787437 11.00000 0.02180 0.01819 = 0.02205 -0.00647 -0.00225 0.00241 O6 4 0.991131 0.218530 0.319372 11.00000 0.02665 0.03213 = 0.04706 -0.00737 -0.00214 0.00822 O7 4 0.281559 0.383064 0.331124 11.00000 0.02548 0.04586 = 0.05730 0.00443 -0.01140 -0.00345 O8 4 0.376362 0.556067 0.236814 11.00000 0.04019 0.04062 = 0.03278 0.00477 -0.00832 0.01500 O5 4 0.762056 0.124475 0.407592 11.00000 0.03767 0.02654 = 0.05175 0.00753 -0.01470 -0.00163 N7 3 0.814086 0.422926 0.263812 11.00000 0.02162 0.02307 = 0.02089 -0.00835 -0.00166 -0.00001 N8 3 0.690520 0.494743 0.244883 11.00000 0.02761 0.02143 = 0.02127 -0.00208 -0.00537 0.00102 N9 3 0.587166 0.310654 0.338870 11.00000 0.02489 0.02160 = 0.02385 -0.00634 -0.00838 -0.00039 N10 3 0.394204 0.456980 0.286533 11.00000 0.03257 0.03387 = 0.02637 -0.00732 -0.01106 0.00523 N11 3 0.842902 0.211677 0.351625 11.00000 0.02462 0.02253 = 0.02832 -0.00822 -0.00755 0.00108 N12 3 0.977808 0.467653 0.225936 11.00000 0.02483 0.02804 = 0.03392 -0.00823 0.00030 -0.00435 H12A 2 1.030750 0.458010 0.272451 11.00000 -1.20000 H12B 2 1.016585 0.430533 0.181455 11.00000 -1.20000 C3 1 0.748324 0.314515 0.319477 11.00000 0.02496 0.01998 = 0.02088 -0.00703 -0.00866 0.00237 C4 1 0.560580 0.421035 0.291668 11.00000 0.02469 0.02421 = 0.02006 -0.00425 -0.00514 0.00348 O16 4 0.589234 0.344496 0.099522 11.00000 0.03388 0.04022 = 0.03387 -0.01769 -0.00370 0.01320 O15 4 0.555659 0.223657 0.000474 11.00000 0.02898 0.05040 = 0.04347 -0.02004 -0.01259 0.00183 O14 4 1.261853 0.049294 0.001114 11.00000 0.02985 0.03331 = 0.04362 -0.01229 -0.01248 0.01140 O13 4 1.081078 -0.012614 -0.072353 11.00000 0.03616 0.04099 = 0.05534 -0.03313 -0.00766 0.00456 N19 3 1.044956 0.220728 0.064328 11.00000 0.02242 0.01949 = 0.02042 -0.00370 -0.00554 0.00228 N20 3 0.908665 0.282715 0.086174 11.00000 0.02185 0.02249 = 0.02313 -0.00724 -0.00340 0.00123 N21 3 0.863519 0.145223 -0.005652 11.00000 0.02255 0.02293 = 0.02433 -0.00712 -0.00143 0.00107 N22 3 1.128659 0.052793 -0.022739 11.00000 0.02919 0.02241 = 0.02480 -0.00656 -0.00078 0.00026 N23 3 0.637056 0.269894 0.048060 11.00000 0.02457 0.03035 = 0.02467 -0.00375 -0.00552 0.00080 N24 3 1.185669 0.250893 0.097119 11.00000 0.02544 0.03074 = 0.02705 -0.00607 -0.00930 0.00282 H24A 2 1.205373 0.191737 0.140741 11.00000 -1.20000 H24B 2 1.272246 0.262886 0.047067 11.00000 -1.20000 C8 1 0.806892 0.231900 0.042547 11.00000 0.02310 0.02222 = 0.02059 -0.00345 -0.00309 0.00074 C7 1 1.013769 0.139937 0.010330 11.00000 0.02569 0.01714 = 0.02280 -0.00329 -0.00259 -0.00052 O19 4 0.466127 0.397720 0.721928 11.00000 0.02505 0.03664 = 0.04052 -0.00775 0.00344 0.00297 O20 4 0.327184 0.264726 0.850441 11.00000 0.03160 0.02649 = 0.02975 -0.00237 -0.00835 0.00381 O18 4 -0.125225 0.723381 0.754026 11.00000 0.03199 0.02963 = 0.07442 -0.01590 -0.01658 0.00959 O17 4 0.062948 0.727349 0.613179 11.00000 0.04621 0.03144 = 0.04670 0.00889 -0.02290 -0.00530 N25 3 -0.038979 0.487771 0.824074 11.00000 0.01875 0.02395 = 0.02399 -0.00612 -0.00378 0.00445 N26 3 0.055067 0.394904 0.849578 11.00000 0.02319 0.02353 = 0.02075 -0.00601 -0.00496 0.00492 N28 3 -0.008558 0.682808 0.702030 11.00000 0.03109 0.02134 = 0.04415 -0.00284 -0.02116 0.00044 N29 3 0.341064 0.359174 0.786761 11.00000 0.02490 0.02308 = 0.02332 -0.00775 -0.00513 0.00053 N30 3 -0.208192 0.478580 0.870942 11.00000 0.02419 0.03608 = 0.04246 -0.00625 0.00273 0.00617 H30A 2 -0.229776 0.549266 0.898241 11.00000 -1.20000 H30B 2 -0.265661 0.494370 0.816524 11.00000 -1.20000 N27 3 0.206377 0.539068 0.721631 11.00000 0.02238 0.02263 = 0.02786 -0.00458 -0.00829 -0.00155 C10 1 0.197789 0.432252 0.785906 11.00000 0.02230 0.01842 = 0.02175 -0.00723 -0.00698 -0.00040 C9 1 0.053556 0.570359 0.749259 11.00000 0.02775 0.01727 = 0.02778 -0.00580 -0.01175 -0.00058 O29 4 0.303397 0.262853 0.582918 11.00000 0.03733 0.02890 = 0.08053 -0.02103 -0.02500 0.00125 O30 4 0.113239 0.193398 0.721874 11.00000 0.04647 0.05358 = 0.05701 -0.03780 -0.02571 0.02075 O31 4 -0.140090 -0.142568 0.473462 11.00000 0.03264 0.02828 = 0.02911 -0.01152 -0.00943 0.00131 O32 4 -0.283677 -0.075761 0.602060 11.00000 0.02609 0.04129 = 0.03600 -0.01076 0.00387 -0.00577 N43 3 0.222221 0.065641 0.506924 11.00000 0.02400 0.02041 = 0.02271 -0.00451 -0.00524 -0.00202 N44 3 0.129549 -0.013058 0.478127 11.00000 0.02667 0.01857 = 0.02152 -0.00081 -0.00499 -0.00263 N45 3 -0.025501 0.065014 0.607817 11.00000 0.02738 0.02362 = 0.02777 -0.00979 -0.01315 0.00800 N46 3 0.186076 0.195769 0.633154 11.00000 0.03090 0.03099 = 0.05265 -0.02434 -0.02465 0.01233 N47 3 -0.155761 -0.080698 0.538373 11.00000 0.02217 0.02186 = 0.02510 -0.00153 -0.00736 0.00201 N48 3 0.391319 0.079119 0.461368 11.00000 0.02350 0.03531 = 0.03507 -0.00543 0.00128 -0.00717 H48B 2 0.437168 0.067688 0.517751 11.00000 -1.20000 H48A 2 0.407238 0.159481 0.435744 11.00000 -1.20000 C16 1 -0.014229 -0.008733 0.541022 11.00000 0.02551 0.01786 = 0.01902 -0.00330 -0.00689 0.00236 C15 1 0.127171 0.109754 0.582105 11.00000 0.02948 0.01909 = 0.02968 -0.00961 -0.01441 0.00568 O24 4 0.954888 0.356850 0.476296 11.00000 0.02635 0.03069 = 0.03423 -0.01394 -0.00327 0.00438 O23 4 1.005988 0.423703 0.605418 11.00000 0.03651 0.03871 = 0.03732 -0.01212 -0.01852 0.00808 O21 4 0.529801 0.699426 0.719223 11.00000 0.03561 0.04722 = 0.04780 -0.03038 0.00593 -0.00466 O22 4 0.435997 0.766310 0.580177 11.00000 0.02772 0.02908 = 0.07513 -0.01797 -0.01107 0.00703 N31 3 0.571482 0.568135 0.506258 11.00000 0.02250 0.02056 = 0.02302 -0.00287 -0.00473 0.00285 N32 3 0.683412 0.487432 0.479771 11.00000 0.02443 0.02139 = 0.02081 -0.00260 -0.00259 0.00302 N33 3 0.747607 0.567622 0.607569 11.00000 0.02218 0.02319 = 0.02857 -0.00838 -0.00192 -0.00239 N35 3 0.925456 0.419545 0.541095 11.00000 0.02609 0.02032 = 0.02488 -0.00204 -0.00391 -0.00120 N36 3 0.433284 0.581411 0.461421 11.00000 0.02789 0.03925 = 0.03429 -0.00810 -0.01293 0.00874 H36B 2 0.338779 0.568882 0.514953 11.00000 -1.20000 H36A 2 0.431650 0.667905 0.427877 11.00000 -1.20000 N34 3 0.518171 0.699953 0.631040 11.00000 0.02208 0.02782 = 0.05022 -0.02133 0.00280 -0.00313 C11 1 0.614718 0.613049 0.581223 11.00000 0.02141 0.01839 = 0.02779 -0.00701 -0.00117 -0.00336 C12 1 0.782531 0.493156 0.542043 11.00000 0.02090 0.01708 = 0.02004 -0.00317 -0.00150 -0.00053 O9 4 0.430030 0.499914 -0.083809 11.00000 0.03476 0.03996 = 0.04163 -0.02564 -0.00960 0.00725 O10 4 0.193484 0.541819 0.003631 11.00000 0.02681 0.03465 = 0.04397 -0.01061 -0.00046 -0.00597 O12 4 0.767946 0.850714 0.113738 11.00000 0.04959 0.05598 = 0.05064 -0.02240 -0.02119 -0.00956 O11 4 0.883481 0.726710 0.020907 11.00000 0.02502 0.05765 = 0.06582 -0.01881 -0.01181 0.00302 N14 3 0.466239 0.785857 0.090527 11.00000 0.02837 0.02786 = 0.02246 -0.00802 -0.00831 0.00496 N15 3 0.589578 0.648213 0.000944 11.00000 0.02111 0.02589 = 0.02543 -0.00594 -0.00716 0.00424 N17 3 0.763317 0.774445 0.063305 11.00000 0.02879 0.03658 = 0.03724 -0.00648 -0.01549 -0.00359 N16 3 0.344059 0.555040 -0.025484 11.00000 0.02512 0.02089 = 0.02813 -0.00432 -0.00680 0.00053 N13 3 0.352173 0.722919 0.063944 11.00000 0.02160 0.02515 = 0.02092 -0.00567 -0.00395 0.00429 N18 3 0.185518 0.745898 0.095565 11.00000 0.02216 0.03608 = 0.03052 -0.00784 -0.00270 0.00800 H18A 2 0.131171 0.670082 0.127057 11.00000 -1.20000 H18B 2 0.152970 0.779721 0.045571 11.00000 -1.20000 C5 1 0.603732 0.736680 0.050002 11.00000 0.02401 0.02578 = 0.02780 -0.00390 -0.00748 0.00012 C6 1 0.428683 0.642487 0.011120 11.00000 0.02649 0.02058 = 0.02218 -0.00422 -0.00715 0.00172 HKLF 4 REM v2 in P1 REM R1 = 0.0344 for 4379 Fo > 4sig(Fo) and 0.0442 for all 5066 data REM 913 parameters refined using 3 restraints END WGHT 0.0369 0.0000 REM Highest difference peak 0.254, deepest hole -0.256, 1-sigma level 0.047 Q1 1 0.5169 0.7943 0.3649 11.00000 0.05 0.25 Q2 1 -0.2249 0.3926 0.8351 11.00000 0.05 0.23 Q3 1 -0.1083 0.2185 0.6003 11.00000 0.05 0.22 Q4 1 0.2449 0.7643 0.3795 11.00000 0.05 0.21 Q5 1 0.7080 0.5775 0.2216 11.00000 0.05 0.20 Q6 1 0.2821 0.7202 0.3704 11.00000 0.05 0.20 Q7 1 0.1161 0.5273 0.7233 11.00000 0.05 0.20 Q8 1 1.3194 0.1215 0.0235 11.00000 0.05 0.19 Q9 1 1.1912 -0.0881 -0.0436 11.00000 0.05 0.19 Q10 1 0.3370 -0.1052 0.9315 11.00000 0.05 0.19 Q11 1 0.7086 0.6530 0.7188 11.00000 0.05 0.18 Q12 1 0.9375 0.3423 0.1590 11.00000 0.05 0.18 Q13 1 0.4299 1.0679 0.2080 11.00000 0.05 0.18 Q14 1 0.3751 0.0637 0.6928 11.00000 0.05 0.18 Q15 1 0.2572 0.1302 0.7010 11.00000 0.05 0.18 Q16 1 -0.0944 0.7863 0.2567 11.00000 0.05 0.18 Q17 1 0.6495 0.3124 0.6980 11.00000 0.05 0.17 Q18 1 0.5114 0.6758 -0.0385 11.00000 0.05 0.17 Q19 1 0.9980 0.2860 0.2447 11.00000 0.05 0.17 Q20 1 0.2013 0.4349 0.2793 11.00000 0.05 0.17 ; # Attachment '- gx626_DABT.cif' data_gx626 _database_code_depnum_ccdc_archive 'CCDC 871738' _publ_section_abstract ? _publ_section_comment ? _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 ; 'Sat Nov 05 19:09:56 2011' ; _audit_update_record 07.11.2011 _chemical_name_systematic 5,5-bis(1-aminotetrazole) _chemical_compound_source ? _chemical_name_common 5,5-bis(1-aminotetrazole) _chemical_formula_moiety 'C2 H4 N10' _chemical_formula_sum 'C2 H4 N10' _chemical_formula_weight 168.15 _cell_length_a 6.2087(6) _cell_length_b 9.9845(10) _cell_length_c 10.6782(14) _cell_angle_alpha 90.106(9) _cell_angle_beta 90.874(9) _cell_angle_gamma 106.336(9) _cell_volume 635.14(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1094 _cell_measurement_theta_min 4.2455 _cell_measurement_theta_max 33.5639 _cell_special_details ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.759 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.139 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9646 _exptl_absorpt_correction_T_max 0.9862 _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 3443 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.25 _diffrn_reflns_theta_max 26.50 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.982 _reflns_number_total 2592 _reflns_number_gt 2034 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.1081085000 _diffrn_orient_matrix_UB_12 -0.0482162000 _diffrn_orient_matrix_UB_13 -0.0059342000 _diffrn_orient_matrix_UB_21 0.0469850000 _diffrn_orient_matrix_UB_22 -0.0557781000 _diffrn_orient_matrix_UB_23 0.0123383000 _diffrn_orient_matrix_UB_31 -0.0167887000 _diffrn_orient_matrix_UB_32 0.0066680000 _diffrn_orient_matrix_UB_33 0.0650091000 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1 ' 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' 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 0.410 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.059 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.1524P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2592 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1370 _refine_ls_wR_factor_gt 0.1260 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _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 N1 N 0.0050(3) 0.6276(2) 0.38334(18) 0.0198(4) Uani 1 1 d . . . N5 N -0.1940(4) 0.6673(3) 0.3708(2) 0.0258(5) Uani 1 1 d . . . N6 N 0.0890(3) 0.3982(2) 0.12708(19) 0.0223(5) Uani 1 1 d . . . N7 N -0.0593(4) 0.3349(2) 0.0387(2) 0.0263(5) Uani 1 1 d . . . N4 N 0.2866(3) 0.5409(2) 0.36912(19) 0.0242(5) Uani 1 1 d . . . N3 N 0.3167(3) 0.6313(2) 0.4687(2) 0.0257(5) Uani 1 1 d . . . N2 N 0.1473(3) 0.6832(2) 0.47812(19) 0.0226(5) Uani 1 1 d . . . N8 N -0.2469(4) 0.3600(2) 0.0648(2) 0.0303(5) Uani 1 1 d . . . N10 N 0.3073(4) 0.3859(3) 0.1242(2) 0.0302(6) Uani 1 1 d . . . N9 N -0.2250(3) 0.4396(2) 0.1716(2) 0.0284(5) Uani 1 1 d . . . C2 C -0.0144(4) 0.4616(2) 0.2081(2) 0.0193(5) Uani 1 1 d . . . C1 C 0.0927(4) 0.5410(2) 0.3181(2) 0.0185(5) Uani 1 1 d . . . N11 N 0.4951(3) 0.8627(2) 0.11776(18) 0.0225(5) Uani 1 1 d . . . N15 N 0.6726(4) 0.8026(3) 0.1077(2) 0.0279(5) Uani 1 1 d . . . N14 N 0.2558(4) 0.9837(2) 0.1017(2) 0.0279(5) Uani 1 1 d . . . N12 N 0.3453(4) 0.8191(2) 0.2088(2) 0.0278(5) Uani 1 1 d . . . N13 N 0.2021(4) 0.8912(2) 0.1988(2) 0.0296(5) Uani 1 1 d . . . C3 C 0.4394(4) 0.9636(2) 0.0527(2) 0.0215(5) Uani 1 1 d . . . N18 N 0.7165(4) 0.0709(2) 0.3160(2) 0.0294(5) Uani 1 1 d . . . N20 N 1.2883(4) 0.1953(3) 0.3561(2) 0.0275(5) Uani 1 1 d . . . N17 N 0.9114(4) 0.1481(2) 0.2841(2) 0.0280(5) Uani 1 1 d . . . N16 N 1.0609(3) 0.1230(2) 0.36587(19) 0.0236(5) Uani 1 1 d . . . N19 N 0.7332(4) -0.0072(2) 0.4183(2) 0.0295(5) Uani 1 1 d . . . C4 C 0.9491(4) 0.0271(3) 0.4481(2) 0.0246(6) Uani 1 1 d . . . H15B H 0.800(6) 0.867(4) 0.105(3) 0.045(10) Uiso 1 1 d . . . H5B H -0.305(6) 0.594(4) 0.367(3) 0.047(10) Uiso 1 1 d . . . H20B H 1.326(5) 0.242(3) 0.426(3) 0.033(8) Uiso 1 1 d . . . H10A H 0.410(6) 0.477(4) 0.132(3) 0.061(11) Uiso 1 1 d . . . H15A H 0.661(6) 0.756(4) 0.025(4) 0.063(11) Uiso 1 1 d . . . H20A H 1.371(6) 0.133(4) 0.355(3) 0.048(10) Uiso 1 1 d . . . H5A H -0.180(6) 0.716(4) 0.295(3) 0.050(10) Uiso 1 1 d . . . H10B H 0.324(6) 0.342(4) 0.192(3) 0.052(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0179(10) 0.0192(10) 0.0226(10) -0.0012(8) 0.0005(8) 0.0057(8) N5 0.0226(12) 0.0310(13) 0.0273(12) -0.0019(10) -0.0014(10) 0.0136(10) N6 0.0206(10) 0.0258(11) 0.0222(11) -0.0031(9) -0.0005(9) 0.0093(9) N7 0.0282(12) 0.0282(12) 0.0246(11) -0.0065(9) -0.0049(9) 0.0116(9) N4 0.0229(11) 0.0241(11) 0.0251(11) -0.0017(9) -0.0018(9) 0.0060(9) N3 0.0252(11) 0.0293(12) 0.0233(11) -0.0031(9) -0.0010(9) 0.0086(9) N2 0.0232(11) 0.0236(11) 0.0208(10) -0.0007(9) -0.0010(9) 0.0064(9) N8 0.0260(11) 0.0352(13) 0.0289(12) -0.0119(10) -0.0010(10) 0.0073(10) N10 0.0234(12) 0.0461(16) 0.0273(13) -0.0036(11) -0.0008(10) 0.0197(11) N9 0.0225(11) 0.0347(13) 0.0274(12) -0.0109(10) -0.0023(9) 0.0072(9) C2 0.0192(12) 0.0193(11) 0.0203(12) 0.0009(9) 0.0017(10) 0.0067(9) C1 0.0172(12) 0.0173(11) 0.0205(12) 0.0020(9) 0.0044(10) 0.0037(9) N11 0.0263(11) 0.0220(11) 0.0184(10) 0.0013(8) 0.0012(9) 0.0057(9) N15 0.0312(13) 0.0302(13) 0.0275(12) 0.0032(10) 0.0006(10) 0.0174(11) N14 0.0262(12) 0.0315(12) 0.0270(11) -0.0001(10) 0.0034(9) 0.0095(10) N12 0.0317(12) 0.0267(12) 0.0219(11) 0.0012(9) 0.0033(10) 0.0029(10) N13 0.0302(12) 0.0320(12) 0.0258(12) 0.0020(10) 0.0043(10) 0.0075(10) C3 0.0257(13) 0.0215(12) 0.0171(11) -0.0011(10) -0.0006(10) 0.0062(11) N18 0.0285(12) 0.0274(12) 0.0331(12) -0.0032(10) -0.0094(10) 0.0096(10) N20 0.0231(12) 0.0292(12) 0.0306(13) -0.0027(10) -0.0027(10) 0.0082(10) N17 0.0314(12) 0.0294(12) 0.0248(11) -0.0058(9) -0.0082(10) 0.0118(10) N16 0.0254(11) 0.0232(11) 0.0235(11) -0.0024(9) -0.0030(9) 0.0091(9) N19 0.0263(12) 0.0279(12) 0.0346(13) -0.0044(10) -0.0084(10) 0.0084(10) C4 0.0275(14) 0.0228(13) 0.0254(13) -0.0056(11) -0.0044(11) 0.0106(11) 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 N1 C1 1.343(3) . ? N1 N2 1.345(3) . ? N1 N5 1.404(3) . ? N5 H5B 0.85(3) . ? N5 H5A 0.94(4) . ? N6 N7 1.335(3) . ? N6 C2 1.343(3) . ? N6 N10 1.396(3) . ? N7 N8 1.293(3) . ? N4 C1 1.314(3) . ? N4 N3 1.370(3) . ? N3 N2 1.301(3) . ? N8 N9 1.371(3) . ? N10 H10A 0.95(4) . ? N10 H10B 0.86(4) . ? N9 C2 1.317(3) . ? C2 C1 1.458(3) . ? N11 N12 1.342(3) . ? N11 C3 1.345(3) . ? N11 N15 1.400(3) . ? N15 H15B 0.87(3) . ? N15 H15A 0.99(4) . ? N14 C3 1.326(3) . ? N14 N13 1.371(3) . ? N12 N13 1.295(3) . ? C3 C3 1.443(5) 2_675 ? N18 N17 1.290(3) . ? N18 N19 1.363(3) . ? N20 N16 1.399(3) . ? N20 H20B 0.87(3) . ? N20 H20A 0.91(4) . ? N17 N16 1.340(3) . ? N16 C4 1.349(3) . ? N19 C4 1.320(3) . ? C4 C4 1.447(5) 2_756 ? 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 108.4(2) . . ? C1 N1 N5 133.4(2) . . ? N2 N1 N5 118.23(19) . . ? N1 N5 H5B 109(2) . . ? N1 N5 H5A 105(2) . . ? H5B N5 H5A 110(3) . . ? N7 N6 C2 108.6(2) . . ? N7 N6 N10 119.3(2) . . ? C2 N6 N10 132.1(2) . . ? N8 N7 N6 106.73(19) . . ? C1 N4 N3 105.30(19) . . ? N2 N3 N4 110.82(19) . . ? N3 N2 N1 106.30(19) . . ? N7 N8 N9 110.7(2) . . ? N6 N10 H10A 109(2) . . ? N6 N10 H10B 106(2) . . ? H10A N10 H10B 106(3) . . ? C2 N9 N8 105.17(19) . . ? N9 C2 N6 108.8(2) . . ? N9 C2 C1 126.5(2) . . ? N6 C2 C1 124.7(2) . . ? N4 C1 N1 109.2(2) . . ? N4 C1 C2 126.6(2) . . ? N1 C1 C2 124.2(2) . . ? N12 N11 C3 108.7(2) . . ? N12 N11 N15 118.8(2) . . ? C3 N11 N15 132.5(2) . . ? N11 N15 H15B 111(2) . . ? N11 N15 H15A 109(2) . . ? H15B N15 H15A 104(3) . . ? C3 N14 N13 105.4(2) . . ? N13 N12 N11 106.7(2) . . ? N12 N13 N14 110.8(2) . . ? N14 C3 N11 108.5(2) . . ? N14 C3 C3 126.4(3) . 2_675 ? N11 C3 C3 125.1(3) . 2_675 ? N17 N18 N19 110.9(2) . . ? N16 N20 H20B 106.3(19) . . ? N16 N20 H20A 109(2) . . ? H20B N20 H20A 105(3) . . ? N18 N17 N16 107.0(2) . . ? N17 N16 C4 108.1(2) . . ? N17 N16 N20 119.8(2) . . ? C4 N16 N20 132.1(2) . . ? C4 N19 N18 105.5(2) . . ? N19 C4 N16 108.5(2) . . ? N19 C4 C4 126.4(3) . 2_756 ? N16 C4 C4 125.1(3) . 2_756 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N6 N7 N8 0.5(3) . . . . ? N10 N6 N7 N8 178.5(2) . . . . ? C1 N4 N3 N2 0.5(3) . . . . ? N4 N3 N2 N1 -0.6(3) . . . . ? C1 N1 N2 N3 0.4(3) . . . . ? N5 N1 N2 N3 -179.5(2) . . . . ? N6 N7 N8 N9 -0.4(3) . . . . ? N7 N8 N9 C2 0.2(3) . . . . ? N8 N9 C2 N6 0.1(3) . . . . ? N8 N9 C2 C1 -179.8(2) . . . . ? N7 N6 C2 N9 -0.3(3) . . . . ? N10 N6 C2 N9 -178.0(3) . . . . ? N7 N6 C2 C1 179.6(2) . . . . ? N10 N6 C2 C1 1.9(4) . . . . ? N3 N4 C1 N1 -0.2(3) . . . . ? N3 N4 C1 C2 179.6(2) . . . . ? N2 N1 C1 N4 -0.1(3) . . . . ? N5 N1 C1 N4 179.8(2) . . . . ? N2 N1 C1 C2 -179.9(2) . . . . ? N5 N1 C1 C2 0.0(4) . . . . ? N9 C2 C1 N4 165.5(3) . . . . ? N6 C2 C1 N4 -14.4(4) . . . . ? N9 C2 C1 N1 -14.8(4) . . . . ? N6 C2 C1 N1 165.4(2) . . . . ? C3 N11 N12 N13 0.3(3) . . . . ? N15 N11 N12 N13 179.3(2) . . . . ? N11 N12 N13 N14 -0.3(3) . . . . ? C3 N14 N13 N12 0.3(3) . . . . ? N13 N14 C3 N11 -0.1(3) . . . . ? N13 N14 C3 C3 179.8(3) . . . 2_675 ? N12 N11 C3 N14 -0.1(3) . . . . ? N15 N11 C3 N14 -178.9(2) . . . . ? N12 N11 C3 C3 180.0(3) . . . 2_675 ? N15 N11 C3 C3 1.2(5) . . . 2_675 ? N19 N18 N17 N16 -0.4(3) . . . . ? N18 N17 N16 C4 0.2(3) . . . . ? N18 N17 N16 N20 -178.5(2) . . . . ? N17 N18 N19 C4 0.4(3) . . . . ? N18 N19 C4 N16 -0.3(3) . . . . ? N18 N19 C4 C4 179.2(3) . . . 2_756 ? N17 N16 C4 N19 0.0(3) . . . . ? N20 N16 C4 N19 178.6(2) . . . . ? N17 N16 C4 C4 -179.4(3) . . . 2_756 ? N20 N16 C4 C4 -0.9(5) . . . 2_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 N15 H15B N13 0.87(3) 2.62(3) 3.286(3) 134(3) 1_655 N5 H5B N4 0.85(3) 2.44(3) 3.115(3) 137(3) 1_455 N20 H20B N3 0.87(3) 2.48(3) 3.157(3) 136(2) 2_766 N20 H20B N5 0.87(3) 2.59(3) 3.350(3) 147(2) 2_666 N10 H10A N9 0.95(4) 2.43(4) 2.838(3) 106(3) 1_655 N15 H15A N10 0.99(4) 2.18(4) 3.133(3) 162(3) 2_665 N15 H15A N8 0.99(4) 2.67(4) 3.231(3) 116(3) 2_565 N20 H20A N18 0.91(4) 2.44(4) 3.269(3) 152(3) 1_655 N5 H5A N15 0.94(4) 2.45(4) 3.313(3) 154(3) 1_455 N10 H10B N20 0.86(4) 2.26(4) 3.110(4) 167(3) 1_455 _geom_special_details ? _iucr_refine_instructions_details ; TITL v1 in P-1 CELL 0.71073 6.2087 9.9845 10.6782 90.106 90.874 106.336 ZERR 4.00 0.0006 0.0010 0.0014 0.009 0.009 0.009 LATT 1 SFAC C N H UNIT 8 40 16 MERG 2 OMIT -2.00 53.00 OMIT 1 -3 2 OMIT -1 -2 3 OMIT 1 -5 4 OMIT -1 1 3 OMIT 1 -2 1 OMIT 1 -5 6 OMIT -1 0 5 OMIT 1 -2 2 OMIT 2 -2 4 OMIT -1 -1 1 OMIT 0 -2 4 OMIT 2 -3 2 OMIT 2 -6 6 OMIT 1 -4 4 OMIT 1 -3 3 OMIT 2 -5 4 OMIT 2 -4 4 EQIV $1 x+1, y, z EQIV $2 x-1, y, z EQIV $3 -x+2, -y+1, -z+1 EQIV $4 -x+1, -y+1, -z+1 EQIV $5 -x+1, -y+1, -z EQIV $6 -x, -y+1, -z HTAB N15 N13_$1 HTAB N5 N4_$2 HTAB N20 N3_$3 HTAB N20 N5_$4 HTAB N10 N9_$1 HTAB N15 N10_$5 HTAB N15 N8_$6 HTAB N20 N18_$1 HTAB N5 N15_$2 HTAB N10 N20_$2 FMAP 2 PLAN 20 SIZE 0.10 0.15 0.26 ACTA BOND $H CONF WGHT 0.05470 0.15240 L.S. 5 TEMP -100.00 FVAR 0.21309 N1 2 0.004975 0.627597 0.383344 11.00000 0.01789 0.01920 = 0.02257 -0.00124 0.00046 0.00571 N5 2 -0.193985 0.667281 0.370776 11.00000 0.02259 0.03099 = 0.02734 -0.00192 -0.00136 0.01355 N6 2 0.089037 0.398232 0.127078 11.00000 0.02056 0.02580 = 0.02215 -0.00314 -0.00046 0.00932 N7 2 -0.059251 0.334906 0.038688 11.00000 0.02817 0.02824 = 0.02461 -0.00645 -0.00486 0.01157 N4 2 0.286626 0.540870 0.369116 11.00000 0.02291 0.02409 = 0.02505 -0.00166 -0.00177 0.00600 N3 2 0.316745 0.631344 0.468696 11.00000 0.02519 0.02926 = 0.02331 -0.00310 -0.00095 0.00862 N2 2 0.147350 0.683203 0.478118 11.00000 0.02320 0.02365 = 0.02079 -0.00070 -0.00099 0.00644 N8 2 -0.246926 0.359983 0.064801 11.00000 0.02604 0.03523 = 0.02885 -0.01191 -0.00100 0.00733 N10 2 0.307313 0.385879 0.124188 11.00000 0.02341 0.04607 = 0.02727 -0.00365 -0.00085 0.01975 N9 2 -0.225014 0.439581 0.171556 11.00000 0.02250 0.03467 = 0.02745 -0.01086 -0.00233 0.00720 C2 1 -0.014353 0.461595 0.208138 11.00000 0.01922 0.01935 = 0.02028 0.00092 0.00171 0.00672 C1 1 0.092704 0.541001 0.318130 11.00000 0.01722 0.01733 = 0.02050 0.00199 0.00440 0.00371 N11 2 0.495120 0.862728 0.117761 11.00000 0.02633 0.02203 = 0.01839 0.00134 0.00117 0.00575 N15 2 0.672593 0.802619 0.107699 11.00000 0.03123 0.03023 = 0.02754 0.00324 0.00064 0.01736 N14 2 0.255816 0.983663 0.101739 11.00000 0.02617 0.03150 = 0.02699 -0.00012 0.00336 0.00951 N12 2 0.345343 0.819115 0.208844 11.00000 0.03171 0.02665 = 0.02191 0.00117 0.00326 0.00288 N13 2 0.202073 0.891197 0.198806 11.00000 0.03022 0.03200 = 0.02582 0.00198 0.00426 0.00749 C3 1 0.439364 0.963601 0.052705 11.00000 0.02568 0.02147 = 0.01711 -0.00106 -0.00064 0.00622 N18 2 0.716545 0.070881 0.315954 11.00000 0.02854 0.02738 = 0.03308 -0.00318 -0.00936 0.00961 N20 2 1.288285 0.195271 0.356130 11.00000 0.02308 0.02916 = 0.03059 -0.00273 -0.00270 0.00825 N17 2 0.911411 0.148145 0.284128 11.00000 0.03139 0.02943 = 0.02479 -0.00577 -0.00816 0.01180 N16 2 1.060937 0.122966 0.365871 11.00000 0.02538 0.02322 = 0.02349 -0.00244 -0.00301 0.00913 N19 2 0.733216 -0.007205 0.418298 11.00000 0.02631 0.02785 = 0.03456 -0.00436 -0.00845 0.00841 C4 1 0.949055 0.027056 0.448125 11.00000 0.02754 0.02277 = 0.02542 -0.00556 -0.00442 0.01060 H15B 3 0.799748 0.866721 0.105091 11.00000 0.04467 H5B 3 -0.304602 0.594263 0.366980 11.00000 0.04733 H20B 3 1.325933 0.241805 0.425618 11.00000 0.03260 H10A 3 0.410069 0.476856 0.132256 11.00000 0.06133 H15A 3 0.661263 0.755818 0.025255 11.00000 0.06329 H20A 3 1.370606 0.133225 0.354861 11.00000 0.04808 H5A 3 -0.180305 0.716079 0.295113 11.00000 0.05010 H10B 3 0.323708 0.342128 0.191676 11.00000 0.05171 HKLF 4 END ; # Attachment '- hx093_12DABT.cif' data_hx093 _database_code_depnum_ccdc_archive 'CCDC 871739' _publ_section_abstract ? _publ_section_comment ? _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 ; 'Sat Feb 18 09:36:07 2012' ; _audit_update_record 23.02.2012 _chemical_name_systematic 5,5-bis(1,2-aminotetrazole _chemical_compound_source ? _chemical_name_common 5,5-bis(1,2-aminotetrazole _chemical_formula_moiety 'C2 H4 N10' _chemical_formula_sum 'C2 H4 N10' _chemical_formula_weight 168.15 _cell_length_a 10.2063(3) _cell_length_b 6.2946(2) _cell_length_c 19.7287(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1267.46(7) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3726 _cell_measurement_theta_min 4.1161 _cell_measurement_theta_max 32.3434 _cell_special_details ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.762 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9527 _exptl_absorpt_correction_T_max 0.9807 _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 12017 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0144 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 26.49 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.995 _reflns_number_total 1300 _reflns_number_gt 1103 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.0161562000 _diffrn_orient_matrix_UB_12 0.0168918000 _diffrn_orient_matrix_UB_13 0.0345521000 _diffrn_orient_matrix_UB_21 -0.0664432000 _diffrn_orient_matrix_UB_22 0.0163420000 _diffrn_orient_matrix_UB_23 -0.0091340000 _diffrn_orient_matrix_UB_31 -0.0123331000 _diffrn_orient_matrix_UB_32 -0.1102195000 _diffrn_orient_matrix_UB_33 0.0039460000 _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' N N 0.0061 0.0033 '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+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 0.275 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.046 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0489P)^2^+0.1652P] 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 0.0025(6) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1300 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0813 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 N1 N 0.03650(9) 0.24111(16) 0.07450(5) 0.0209(2) Uani 1 1 d . . . N2 N 0.07161(11) 0.25568(17) 0.00943(5) 0.0291(3) Uani 1 1 d . . . N3 N 0.19632(12) 0.30693(17) 0.00995(5) 0.0321(3) Uani 1 1 d . . . N4 N 0.24217(10) 0.32601(16) 0.07377(5) 0.0279(3) Uani 1 1 d . . . N5 N -0.08813(10) 0.16996(18) 0.09405(5) 0.0249(3) Uani 1 1 d . . . N6 N 0.04049(9) 0.23664(16) 0.22652(5) 0.0207(2) Uani 1 1 d . . . N7 N 0.09368(10) 0.25739(15) 0.28717(5) 0.0190(2) Uani 1 1 d . . . N8 N 0.21909(10) 0.30697(16) 0.28759(5) 0.0238(3) Uani 1 1 d . . . N9 N 0.25302(10) 0.32313(15) 0.22244(5) 0.0238(3) Uani 1 1 d . . . N10 N 0.02374(11) 0.21478(18) 0.34629(5) 0.0252(3) Uani 1 1 d . . . C1 C 0.14096(11) 0.28239(17) 0.11361(6) 0.0198(3) Uani 1 1 d . . . C2 C 0.14414(10) 0.28056(17) 0.18716(6) 0.0189(3) Uani 1 1 d . . . H5A H -0.1416(14) 0.189(2) 0.0571(9) 0.033(4) Uiso 1 1 d . . . H5B H -0.1145(19) 0.257(3) 0.1270(11) 0.044(5) Uiso 1 1 d . . . H10B H 0.057(2) 0.308(3) 0.3772(10) 0.049(5) Uiso 1 1 d . . . H10A H -0.0626(18) 0.254(3) 0.3350(8) 0.042(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0214(5) 0.0253(5) 0.0161(5) 0.0000(4) 0.0026(4) 0.0022(4) N2 0.0359(6) 0.0344(6) 0.0171(5) 0.0003(4) 0.0068(4) 0.0019(5) N3 0.0365(6) 0.0333(6) 0.0265(6) -0.0012(4) 0.0125(5) -0.0028(5) N4 0.0277(6) 0.0273(6) 0.0288(6) -0.0017(4) 0.0090(4) -0.0033(4) N5 0.0177(5) 0.0393(6) 0.0177(5) -0.0018(4) -0.0002(4) 0.0011(4) N6 0.0169(5) 0.0273(5) 0.0177(5) -0.0025(4) -0.0019(4) 0.0017(4) N7 0.0186(5) 0.0213(5) 0.0171(5) -0.0014(4) -0.0022(4) 0.0008(4) N8 0.0209(5) 0.0255(6) 0.0251(6) 0.0004(4) -0.0050(4) -0.0028(4) N9 0.0198(5) 0.0251(5) 0.0265(5) 0.0025(4) -0.0023(4) -0.0025(4) N10 0.0258(6) 0.0335(6) 0.0164(5) -0.0031(4) 0.0012(4) -0.0003(4) C1 0.0189(6) 0.0179(6) 0.0226(6) -0.0006(4) 0.0018(4) 0.0014(4) C2 0.0170(5) 0.0169(5) 0.0228(6) -0.0005(4) -0.0003(4) 0.0016(4) 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 N1 N2 1.3360(15) . ? N1 C1 1.3415(15) . ? N1 N5 1.4025(14) . ? N2 N3 1.3131(16) . ? N3 N4 1.3487(16) . ? N4 C1 1.3267(15) . ? N5 H5A 0.918(17) . ? N5 H5B 0.89(2) . ? N6 N7 1.3204(13) . ? N6 C2 1.3410(15) . ? N7 N8 1.3175(14) . ? N7 N10 1.3936(13) . ? N8 N9 1.3350(14) . ? N9 C2 1.3383(15) . ? N10 H10B 0.91(2) . ? N10 H10A 0.943(18) . ? C1 C2 1.4514(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C1 109.04(10) . . ? N2 N1 N5 121.96(10) . . ? C1 N1 N5 128.64(10) . . ? N3 N2 N1 105.63(10) . . ? N2 N3 N4 111.44(10) . . ? C1 N4 N3 105.34(11) . . ? N1 N5 H5A 106.2(9) . . ? N1 N5 H5B 106.1(12) . . ? H5A N5 H5B 108.6(16) . . ? N7 N6 C2 100.37(9) . . ? N8 N7 N6 115.38(9) . . ? N8 N7 N10 122.54(9) . . ? N6 N7 N10 121.93(9) . . ? N7 N8 N9 105.30(9) . . ? N8 N9 C2 105.67(10) . . ? N7 N10 H10B 104.1(12) . . ? N7 N10 H10A 103.4(10) . . ? H10B N10 H10A 109.7(15) . . ? N4 C1 N1 108.55(11) . . ? N4 C1 C2 125.21(11) . . ? N1 C1 C2 126.24(10) . . ? N9 C2 N6 113.28(11) . . ? N9 C2 C1 122.47(10) . . ? N6 C2 C1 124.25(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 N3 -0.43(13) . . . . ? N5 N1 N2 N3 -174.15(10) . . . . ? N1 N2 N3 N4 -0.10(13) . . . . ? N2 N3 N4 C1 0.60(13) . . . . ? C2 N6 N7 N8 -0.74(12) . . . . ? C2 N6 N7 N10 -176.38(10) . . . . ? N6 N7 N8 N9 0.67(13) . . . . ? N10 N7 N8 N9 176.28(10) . . . . ? N7 N8 N9 C2 -0.27(12) . . . . ? N3 N4 C1 N1 -0.85(12) . . . . ? N3 N4 C1 C2 179.24(10) . . . . ? N2 N1 C1 N4 0.82(13) . . . . ? N5 N1 C1 N4 173.99(10) . . . . ? N2 N1 C1 C2 -179.27(10) . . . . ? N5 N1 C1 C2 -6.10(18) . . . . ? N8 N9 C2 N6 -0.18(13) . . . . ? N8 N9 C2 C1 179.91(9) . . . . ? N7 N6 C2 N9 0.54(12) . . . . ? N7 N6 C2 C1 -179.56(10) . . . . ? N4 C1 C2 N9 -0.32(17) . . . . ? N1 C1 C2 N9 179.79(11) . . . . ? N4 C1 C2 N6 179.78(11) . . . . ? N1 C1 C2 N6 -0.11(17) . . . . ? 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 N3 0.918(17) 2.118(16) 3.0118(15) 164.0(13) 3_455 N5 H5B N8 0.89(2) 2.41(2) 3.1731(14) 143.3(15) 6_556 N5 H5B N6 0.89(2) 2.52(2) 2.9546(15) 110.2(14) . N10 H10B N5 0.91(2) 2.370(18) 3.1665(16) 145.9(16) 4 N10 H10B N2 0.91(2) 2.64(2) 3.2607(15) 125.7(14) 8_566 N10 H10A N9 0.943(18) 2.239(18) 3.1525(16) 163.0(14) 6_556 _geom_special_details ? _iucr_refine_instructions_details ; TITL v1 in Pbca CELL 0.71073 10.2063 6.2946 19.7287 90.000 90.000 90.000 ZERR 8.00 0.0003 0.0002 0.0006 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 N H UNIT 16 80 32 MERG 2 OMIT -2.00 53.00 OMIT 1 0 8 OMIT 5 0 2 OMIT 1 1 19 EQIV $1 x-1/2, -y+1/2, -z EQIV $2 x-1/2, y, -z+1/2 EQIV $3 -x, y+1/2, -z+1/2 EQIV $4 x, -y+1/2, z+1/2 HTAB N5 N3_$1 HTAB N5 N8_$2 HTAB N5 N6 HTAB N10 N5_$3 HTAB N10 N2_$4 HTAB N10 N9_$2 FMAP 2 PLAN 20 SIZE 0.14 0.28 0.35 ACTA BOND $H CONF L.S. 10 TEMP -100.00 WGHT 0.048900 0.165200 EXTI 0.002483 FVAR 0.28216 N1 2 0.036499 0.241112 0.074502 11.00000 0.02145 0.02528 = 0.01612 0.00004 0.00263 0.00222 N2 2 0.071610 0.255681 0.009430 11.00000 0.03593 0.03438 = 0.01707 0.00034 0.00679 0.00186 N3 2 0.196315 0.306929 0.009949 11.00000 0.03651 0.03335 = 0.02648 -0.00117 0.01249 -0.00276 N4 2 0.242167 0.326012 0.073775 11.00000 0.02769 0.02730 = 0.02879 -0.00168 0.00895 -0.00325 N5 2 -0.088125 0.169964 0.094046 11.00000 0.01771 0.03934 = 0.01772 -0.00183 -0.00024 0.00108 N6 2 0.040492 0.236636 0.226516 11.00000 0.01689 0.02734 = 0.01773 -0.00246 -0.00189 0.00174 N7 2 0.093679 0.257389 0.287167 11.00000 0.01858 0.02131 = 0.01714 -0.00138 -0.00217 0.00079 N8 2 0.219087 0.306971 0.287590 11.00000 0.02087 0.02550 = 0.02505 0.00040 -0.00501 -0.00280 N9 2 0.253015 0.323128 0.222439 11.00000 0.01976 0.02508 = 0.02654 0.00245 -0.00232 -0.00253 N10 2 0.023737 0.214775 0.346290 11.00000 0.02576 0.03354 = 0.01643 -0.00311 0.00115 -0.00031 C1 1 0.140965 0.282388 0.113614 11.00000 0.01893 0.01794 = 0.02261 -0.00059 0.00178 0.00140 C2 1 0.144138 0.280563 0.187162 11.00000 0.01695 0.01693 = 0.02285 -0.00053 -0.00031 0.00156 H5A 3 -0.141600 0.189096 0.057103 11.00000 0.03289 H5B 3 -0.114525 0.257108 0.127011 11.00000 0.04422 H10B 3 0.057142 0.307868 0.377163 11.00000 0.04945 H10A 3 -0.062634 0.254333 0.335036 11.00000 0.04184 HKLF 4 REM v1 in Pbca REM R1 = 0.0291 for 1103 Fo > 4sig(Fo) and 0.0363 for all 1300 data REM 126 parameters refined using 0 restraints END WGHT 0.0488 0.1780 REM Highest difference peak 0.275, deepest hole -0.189, 1-sigma level 0.046 Q1 1 0.1432 0.2821 0.1503 11.00000 0.05 0.27 Q2 1 0.0880 0.2531 0.0984 11.00000 0.05 0.20 Q3 1 0.1002 0.2543 0.2020 11.00000 0.05 0.20 Q4 1 0.0208 0.2442 -0.0185 11.00000 0.05 0.17 Q5 1 0.1876 0.3360 0.2019 11.00000 0.05 0.15 Q6 1 -0.0024 0.2573 0.2177 11.00000 0.05 0.14 Q7 1 0.0586 0.2489 0.3149 11.00000 0.05 0.14 Q8 1 -0.0747 0.0037 0.0957 11.00000 0.05 0.14 Q9 1 0.0032 0.0462 0.3448 11.00000 0.05 0.13 Q10 1 -0.1303 0.0454 0.1255 11.00000 0.05 0.12 Q11 1 0.1963 0.2590 0.0999 11.00000 0.05 0.11 Q12 1 0.0498 0.4079 0.0797 11.00000 0.05 0.11 Q13 1 -0.0152 0.2282 0.0812 11.00000 0.05 0.11 Q14 1 0.2562 0.3318 -0.0182 11.00000 0.05 0.11 Q15 1 0.0604 0.0811 0.3765 11.00000 0.05 0.11 Q16 1 0.1634 0.3603 0.0999 11.00000 0.05 0.10 Q17 1 0.0480 0.2705 0.0401 11.00000 0.05 0.10 Q18 1 -0.0547 0.1773 0.2150 11.00000 0.05 0.10 Q19 1 0.1211 0.3628 0.0007 11.00000 0.05 0.10 Q20 1 0.3092 0.4002 0.1980 11.00000 0.05 0.10 ;