# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shrv231 #TrackingRef 'shrv231-final.cif' _audit_creation_date 2013-02-28 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; 3,5-dinitro-N1-(2,2,2-trinitroethyl)-1H-pyrazole-1,4-diamine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H5 N9 O10' _chemical_formula_sum 'C5 H5 N9 O10' _chemical_formula_weight 351.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 11.0318(17) _cell_length_b 10.0035(15) _cell_length_c 22.999(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2538.1(7) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.838 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.177 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.9198 _exptl_absorpt_correction_T_max 0.9894 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21706 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 26.50 _reflns_number_total 2606 _reflns_number_gt 2150 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_structure_refinement 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_molecular_graphics 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0402P)^2^+0.9534P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2606 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0840 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 N1 N 1.02262(11) 0.87182(13) 0.58544(5) 0.0157(3) Uani 1 1 d . . . N2 N 0.93224(11) 0.89438(13) 0.54933(5) 0.0168(3) Uani 1 1 d . . . C3 C 0.88801(13) 0.77365(15) 0.53731(6) 0.0164(3) Uani 1 1 d . . . C4 C 0.94847(14) 0.66744(16) 0.56561(6) 0.0172(3) Uani 1 1 d . . . C5 C 1.03619(13) 0.73714(15) 0.59745(6) 0.0161(3) Uani 1 1 d . . . N6 N 0.78964(12) 0.76109(13) 0.49788(6) 0.0179(3) Uani 1 1 d . . . O7 O 0.73467(10) 0.86181(12) 0.48216(5) 0.0235(3) Uani 1 1 d . . . O8 O 0.76529(11) 0.64708(12) 0.48114(5) 0.0261(3) Uani 1 1 d . . . N9 N 0.92738(13) 0.53614(13) 0.56320(6) 0.0250(3) Uani 1 1 d . . . H9A H 0.9723 0.4807 0.5837 0.030 Uiso 1 1 calc R . . H9B H 0.8686 0.5051 0.5411 0.030 Uiso 1 1 calc R . . N10 N 1.12968(11) 0.68217(13) 0.63085(5) 0.0187(3) Uani 1 1 d . . . O11 O 1.13289(10) 0.55800(11) 0.63410(5) 0.0241(3) Uani 1 1 d . . . O12 O 1.20401(10) 0.75622(12) 0.65475(5) 0.0258(3) Uani 1 1 d . . . N13 N 1.08941(12) 0.98200(13) 0.60364(6) 0.0164(3) Uani 1 1 d . . . H13 H 1.1612(17) 0.9724(18) 0.5937(8) 0.020 Uiso 1 1 d . . . C14 C 1.07689(13) 1.01863(16) 0.66453(6) 0.0165(3) Uani 1 1 d . . . H14A H 1.1519 1.0637 0.6777 0.020 Uiso 1 1 calc R . . H14B H 1.0662 0.9367 0.6881 0.020 Uiso 1 1 calc R . . C15 C 0.96887(14) 1.11147(17) 0.67420(7) 0.0203(4) Uani 1 1 d . . . N16 N 0.99299(13) 1.20701(16) 0.72441(6) 0.0289(4) Uani 1 1 d . . . O17 O 1.02963(12) 1.15278(15) 0.76804(5) 0.0368(3) Uani 1 1 d . . . O18 O 0.97272(17) 1.32475(15) 0.71742(7) 0.0559(5) Uani 1 1 d . . . N19 N 0.94124(14) 1.19646(15) 0.62136(6) 0.0269(3) Uani 1 1 d . . . O20 O 1.02668(12) 1.26075(13) 0.60313(6) 0.0357(3) Uani 1 1 d . . . O21 O 0.83889(12) 1.19240(16) 0.60212(6) 0.0461(4) Uani 1 1 d . . . N22 N 0.85221(12) 1.03831(17) 0.69085(6) 0.0306(4) Uani 1 1 d . . . O23 O 0.78338(12) 1.09817(19) 0.72285(7) 0.0571(5) Uani 1 1 d . . . O24 O 0.83939(11) 0.92756(15) 0.67062(6) 0.0389(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0164(6) 0.0142(7) 0.0166(6) -0.0004(5) 0.0000(5) 0.0002(5) N2 0.0192(6) 0.0161(7) 0.0152(6) 0.0009(5) 0.0002(5) 0.0015(5) C3 0.0178(7) 0.0154(8) 0.0161(7) -0.0003(6) 0.0005(6) 0.0001(6) C4 0.0191(7) 0.0160(8) 0.0166(7) 0.0001(6) 0.0032(6) 0.0021(6) C5 0.0177(7) 0.0132(8) 0.0175(7) 0.0011(6) 0.0009(6) 0.0029(6) N6 0.0199(7) 0.0159(7) 0.0179(7) 0.0010(5) 0.0001(5) -0.0007(5) O7 0.0249(6) 0.0181(6) 0.0274(6) 0.0017(5) -0.0066(5) 0.0034(5) O8 0.0344(7) 0.0152(6) 0.0287(6) -0.0039(5) -0.0099(5) -0.0027(5) N9 0.0304(8) 0.0134(7) 0.0311(8) 0.0019(6) -0.0082(6) 0.0002(6) N10 0.0186(7) 0.0194(8) 0.0181(6) 0.0009(5) 0.0018(5) 0.0033(5) O11 0.0272(6) 0.0147(6) 0.0302(6) 0.0051(5) -0.0020(5) 0.0042(5) O12 0.0218(6) 0.0242(7) 0.0313(6) -0.0023(5) -0.0083(5) 0.0006(5) N13 0.0153(6) 0.0149(7) 0.0190(7) -0.0027(5) 0.0036(5) -0.0033(5) C14 0.0156(7) 0.0171(8) 0.0167(8) 0.0001(6) -0.0012(6) -0.0009(6) C15 0.0204(8) 0.0225(9) 0.0180(8) -0.0016(7) -0.0002(6) 0.0017(7) N16 0.0303(8) 0.0314(9) 0.0250(8) -0.0105(7) 0.0022(6) 0.0047(7) O17 0.0360(7) 0.0543(9) 0.0200(7) -0.0084(6) -0.0030(5) 0.0074(6) O18 0.0943(13) 0.0282(9) 0.0451(9) -0.0163(7) -0.0002(8) 0.0148(8) N19 0.0335(8) 0.0224(8) 0.0249(7) -0.0008(6) -0.0023(6) 0.0120(7) O20 0.0479(8) 0.0233(7) 0.0359(7) 0.0077(6) 0.0077(6) 0.0058(6) O21 0.0390(8) 0.0556(10) 0.0438(8) 0.0022(7) -0.0186(7) 0.0161(7) N22 0.0189(7) 0.0454(11) 0.0276(8) -0.0029(7) 0.0041(6) 0.0004(7) O23 0.0274(8) 0.0826(13) 0.0613(10) -0.0242(9) 0.0200(7) 0.0024(8) O24 0.0306(7) 0.0410(9) 0.0450(8) -0.0044(7) 0.0069(6) -0.0135(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N2 1.3170(17) . ? N1 C5 1.383(2) . ? N1 N13 1.3903(18) . ? N2 C3 1.332(2) . ? C3 C4 1.413(2) . ? C3 N6 1.420(2) . ? C4 N9 1.335(2) . ? C4 C5 1.400(2) . ? C5 N10 1.3986(19) . ? N6 O7 1.2303(17) . ? N6 O8 1.2333(17) . ? N9 H9A 0.8800 . ? N9 H9B 0.8800 . ? N10 O12 1.2342(17) . ? N10 O11 1.2449(17) . ? N13 C14 1.4541(19) . ? N13 H13 0.830(18) . ? C14 C15 1.527(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N19 1.514(2) . ? C15 N16 1.522(2) . ? C15 N22 1.529(2) . ? N16 O18 1.210(2) . ? N16 O17 1.2102(19) . ? N19 O21 1.213(2) . ? N19 O20 1.216(2) . ? N22 O24 1.210(2) . ? N22 O23 1.215(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 N2 N1 C5 112.01(12) . . ? N2 N1 N13 117.08(12) . . ? C5 N1 N13 130.89(12) . . ? N1 N2 C3 104.65(12) . . ? N2 C3 C4 114.41(13) . . ? N2 C3 N6 119.53(13) . . ? C4 C3 N6 126.04(14) . . ? N9 C4 C5 129.23(14) . . ? N9 C4 C3 129.66(14) . . ? C5 C4 C3 101.11(13) . . ? N1 C5 N10 124.92(14) . . ? N1 C5 C4 107.81(13) . . ? N10 C5 C4 126.97(14) . . ? O7 N6 O8 123.94(13) . . ? O7 N6 C3 119.47(13) . . ? O8 N6 C3 116.59(12) . . ? C4 N9 H9A 120.0 . . ? C4 N9 H9B 120.0 . . ? H9A N9 H9B 120.0 . . ? O12 N10 O11 123.59(13) . . ? O12 N10 C5 119.90(13) . . ? O11 N10 C5 116.50(13) . . ? N1 N13 C14 116.06(12) . . ? N1 N13 H13 109.4(13) . . ? C14 N13 H13 112.6(12) . . ? N13 C14 C15 111.57(12) . . ? N13 C14 H14A 109.3 . . ? C15 C14 H14A 109.3 . . ? N13 C14 H14B 109.3 . . ? C15 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? N19 C15 N16 106.95(13) . . ? N19 C15 C14 112.43(12) . . ? N16 C15 C14 110.85(12) . . ? N19 C15 N22 107.48(13) . . ? N16 C15 N22 104.93(12) . . ? C14 C15 N22 113.71(14) . . ? O18 N16 O17 127.48(16) . . ? O18 N16 C15 118.56(15) . . ? O17 N16 C15 113.95(15) . . ? O21 N19 O20 127.84(16) . . ? O21 N19 C15 117.47(15) . . ? O20 N19 C15 114.70(14) . . ? O24 N22 O23 127.67(16) . . ? O24 N22 C15 116.12(13) . . ? O23 N22 C15 116.21(16) . . ? 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 C5 N1 N2 C3 -0.77(16) . . . . ? N13 N1 N2 C3 177.49(12) . . . . ? N1 N2 C3 C4 0.19(17) . . . . ? N1 N2 C3 N6 -178.57(13) . . . . ? N2 C3 C4 N9 179.91(15) . . . . ? N6 C3 C4 N9 -1.4(3) . . . . ? N2 C3 C4 C5 0.42(17) . . . . ? N6 C3 C4 C5 179.09(14) . . . . ? N2 N1 C5 N10 175.06(13) . . . . ? N13 N1 C5 N10 -2.9(2) . . . . ? N2 N1 C5 C4 1.07(17) . . . . ? N13 N1 C5 C4 -176.88(14) . . . . ? N9 C4 C5 N1 179.67(15) . . . . ? C3 C4 C5 N1 -0.85(16) . . . . ? N9 C4 C5 N10 5.8(3) . . . . ? C3 C4 C5 N10 -174.68(14) . . . . ? N2 C3 N6 O7 -11.0(2) . . . . ? C4 C3 N6 O7 170.43(14) . . . . ? N2 C3 N6 O8 168.60(13) . . . . ? C4 C3 N6 O8 -10.0(2) . . . . ? N1 C5 N10 O12 4.1(2) . . . . ? C4 C5 N10 O12 176.90(14) . . . . ? N1 C5 N10 O11 -175.30(14) . . . . ? C4 C5 N10 O11 -2.5(2) . . . . ? N2 N1 N13 C14 111.42(14) . . . . ? C5 N1 N13 C14 -70.7(2) . . . . ? N1 N13 C14 C15 -86.63(16) . . . . ? N13 C14 C15 N19 -28.88(18) . . . . ? N13 C14 C15 N16 -148.52(13) . . . . ? N13 C14 C15 N22 93.55(15) . . . . ? N19 C15 N16 O18 8.9(2) . . . . ? C14 C15 N16 O18 131.78(17) . . . . ? N22 C15 N16 O18 -105.06(18) . . . . ? N19 C15 N16 O17 -172.19(14) . . . . ? C14 C15 N16 O17 -49.30(19) . . . . ? N22 C15 N16 O17 73.85(17) . . . . ? N16 C15 N19 O21 -112.57(16) . . . . ? C14 C15 N19 O21 125.53(16) . . . . ? N22 C15 N19 O21 -0.34(19) . . . . ? N16 C15 N19 O20 67.84(17) . . . . ? C14 C15 N19 O20 -54.06(18) . . . . ? N22 C15 N19 O20 -179.93(14) . . . . ? N19 C15 N22 O24 93.32(17) . . . . ? N16 C15 N22 O24 -153.08(15) . . . . ? C14 C15 N22 O24 -31.8(2) . . . . ? N19 C15 N22 O23 -86.71(18) . . . . ? N16 C15 N22 O23 26.9(2) . . . . ? C14 C15 N22 O23 148.17(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N9 H9A O20 0.88 2.32 3.1036(19) 147.7 1_545 N9 H9B O7 0.88 2.28 3.1163(18) 159.0 6_755 N13 H13 O8 0.830(18) 2.390(18) 3.0388(17) 135.6(15) 2_566 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.315 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 927840' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shrv236 _audit_creation_date 2013-05-16 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; 5-azido-3,4-dinitro-N-(2,2,2-trinitroethyl)-1H-pyrazol-1-amine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H3 N11 O10' _chemical_formula_sum 'C5 H3 N11 O10' _chemical_formula_weight 377.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.9685(7) _cell_length_b 7.7374(3) _cell_length_c 27.7321(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.2480(10) _cell_angle_gamma 90.00 _cell_volume 4069.2(3) _cell_formula_units_Z 12 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.847 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2280 _exptl_absorpt_coefficient_mu 0.177 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.9571 _exptl_absorpt_correction_T_max 0.9965 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 24435 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.07 _diffrn_reflns_theta_max 26.39 _reflns_number_total 8235 _reflns_number_gt 6112 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_structure_refinement 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_molecular_graphics 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+1.1898P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8235 _refine_ls_number_parameters 712 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0919 _refine_ls_wR_factor_gt 0.0822 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1A N 0.15956(7) 0.13422(19) -0.05950(5) 0.0174(3) Uani 1 1 d . . . N2A N 0.20354(7) 0.1916(2) -0.09401(5) 0.0198(3) Uani 1 1 d . . . C3A C 0.25876(9) 0.2448(2) -0.06914(7) 0.0205(4) Uani 1 1 d . . . C4A C 0.25230(9) 0.2248(2) -0.01947(6) 0.0198(4) Uani 1 1 d . . . C5A C 0.18628(9) 0.1493(2) -0.01397(6) 0.0175(4) Uani 1 1 d . . . N6A N 0.32151(8) 0.2933(2) -0.09516(6) 0.0297(4) Uani 1 1 d . . . O7A O 0.31532(8) 0.3951(2) -0.12812(6) 0.0511(5) Uani 1 1 d . . . O8A O 0.37615(7) 0.2203(2) -0.08225(6) 0.0483(4) Uani 1 1 d . . . N9A N 0.29747(8) 0.2904(2) 0.01771(6) 0.0249(4) Uani 1 1 d . . . O10A O 0.34699(8) 0.3821(2) 0.00560(5) 0.0442(4) Uani 1 1 d . . . O11A O 0.28449(7) 0.25604(19) 0.05950(5) 0.0310(3) Uani 1 1 d . . . N12A N 0.14572(8) 0.1021(2) 0.02426(5) 0.0247(4) Uani 1 1 d . . . N13A N 0.17832(8) 0.0235(2) 0.05803(6) 0.0234(4) Uani 1 1 d . . . N14A N 0.19779(9) -0.0506(2) 0.09025(6) 0.0321(4) Uani 1 1 d . . . N15A N 0.09593(7) 0.0551(2) -0.07152(6) 0.0180(3) Uani 1 1 d . . . H15A H 0.0709(10) 0.126(3) -0.0851(7) 0.022 Uiso 1 1 d . . . C16A C 0.10584(9) -0.1006(2) -0.10045(7) 0.0190(4) Uani 1 1 d . . . H16A H 0.1561 -0.1351 -0.0994 0.023 Uiso 1 1 calc R . . H16B H 0.0919 -0.0777 -0.1345 0.023 Uiso 1 1 calc R . . C17A C 0.06068(9) -0.2446(2) -0.08023(7) 0.0194(4) Uani 1 1 d . . . N18A N 0.06378(8) -0.2475(2) -0.02562(6) 0.0257(4) Uani 1 1 d . . . O19A O 0.12342(7) -0.2542(2) -0.00865(5) 0.0362(4) Uani 1 1 d . . . O20A O 0.00921(8) -0.2424(2) -0.00417(5) 0.0428(4) Uani 1 1 d . . . N21A N 0.08378(8) -0.4218(2) -0.09725(6) 0.0277(4) Uani 1 1 d . . . O22A O 0.08098(8) -0.54009(19) -0.06864(6) 0.0421(4) Uani 1 1 d . . . O23A O 0.10166(9) -0.4282(2) -0.13879(6) 0.0452(4) Uani 1 1 d . . . N24A N -0.01650(8) -0.2265(2) -0.09561(6) 0.0217(3) Uani 1 1 d . . . O25A O -0.03753(6) -0.07969(17) -0.09950(5) 0.0275(3) Uani 1 1 d . . . O26A O -0.04995(7) -0.35773(19) -0.10231(6) 0.0395(4) Uani 1 1 d . . . N1B N 0.51777(7) 0.34910(19) 0.09348(5) 0.0189(3) Uani 1 1 d . . . N2B N 0.56224(8) 0.3264(2) 0.05637(5) 0.0228(3) Uani 1 1 d . . . C2B C 0.61659(10) 0.2483(3) 0.07678(7) 0.0250(4) Uani 1 1 d . . . C4B C 0.60900(9) 0.2217(2) 0.12616(6) 0.0211(4) Uani 1 1 d . . . C5B C 0.54280(9) 0.2888(2) 0.13625(6) 0.0180(4) Uani 1 1 d . . . N6B N 0.67678(10) 0.2136(3) 0.04670(7) 0.0413(5) Uani 1 1 d . . . O7B O 0.66609(10) 0.1528(3) 0.00699(6) 0.0550(5) Uani 1 1 d . . . O8B O 0.73406(9) 0.2493(4) 0.06362(7) 0.0917(9) Uani 1 1 d . . . N9B N 0.65856(8) 0.1461(2) 0.15937(6) 0.0258(4) Uani 1 1 d . . . O10B O 0.70384(9) 0.0503(2) 0.14351(6) 0.0538(5) Uani 1 1 d . . . O11B O 0.65408(7) 0.18147(19) 0.20213(5) 0.0290(3) Uani 1 1 d . . . N12B N 0.49961(8) 0.3029(2) 0.17499(6) 0.0235(4) Uani 1 1 d . . . N13B N 0.51755(8) 0.2258(2) 0.21333(6) 0.0258(4) Uani 1 1 d . . . N14B N 0.52352(9) 0.1632(3) 0.24940(7) 0.0445(5) Uani 1 1 d . . . N15B N 0.45448(7) 0.4375(2) 0.08685(6) 0.0199(3) Uani 1 1 d . . . H15B H 0.4267(10) 0.379(3) 0.0698(7) 0.024 Uiso 1 1 d . . . C16B C 0.46318(9) 0.6093(2) 0.06614(6) 0.0196(4) Uani 1 1 d . . . H16C H 0.4331 0.6201 0.0367 0.024 Uiso 1 1 calc R . . H16D H 0.5129 0.6254 0.0569 0.024 Uiso 1 1 calc R . . C17B C 0.44320(9) 0.7479(2) 0.10198(7) 0.0211(4) Uani 1 1 d . . . N18B N 0.49760(8) 0.7753(2) 0.14252(5) 0.0229(3) Uani 1 1 d . . . O19B O 0.50315(9) 0.92129(19) 0.15859(6) 0.0462(4) Uani 1 1 d . . . O20B O 0.53042(6) 0.64995(17) 0.15537(4) 0.0234(3) Uani 1 1 d . . . N21B N 0.43627(10) 0.9228(2) 0.07757(6) 0.0337(4) Uani 1 1 d . . . O22B O 0.38669(10) 1.0128(2) 0.08732(7) 0.0584(5) Uani 1 1 d . . . O23B O 0.48388(9) 0.9579(2) 0.05087(6) 0.0474(4) Uani 1 1 d . . . N24B N 0.37352(8) 0.7067(2) 0.12511(6) 0.0304(4) Uani 1 1 d . . . O25B O 0.32723(7) 0.6641(2) 0.09646(5) 0.0399(4) Uani 1 1 d . . . O26B O 0.36991(8) 0.7188(3) 0.16832(6) 0.0548(5) Uani 1 1 d . . . N1C N 0.15928(7) 1.52079(19) 0.23580(5) 0.0176(3) Uani 1 1 d . . . N2C N 0.10637(7) 1.5436(2) 0.26734(5) 0.0200(3) Uani 1 1 d . . . C3C C 0.05574(9) 1.6097(2) 0.24021(6) 0.0194(4) Uani 1 1 d . . . C4C C 0.07431(9) 1.6318(2) 0.19196(6) 0.0179(4) Uani 1 1 d . . . C5C C 0.14329(9) 1.5709(2) 0.19018(6) 0.0175(4) Uani 1 1 d . . . N6C N -0.01318(8) 1.6337(2) 0.26207(6) 0.0238(4) Uani 1 1 d . . . O7C O -0.06304(7) 1.5613(2) 0.24237(6) 0.0414(4) Uani 1 1 d . . . O8C O -0.01559(8) 1.7196(2) 0.29849(5) 0.0410(4) Uani 1 1 d . . . N9C N 0.03563(8) 1.72052(19) 0.15522(6) 0.0216(3) Uani 1 1 d . . . O10C O -0.01958(7) 1.79251(19) 0.16653(5) 0.0338(3) Uani 1 1 d . . . O11C O 0.05946(7) 1.72254(17) 0.11461(5) 0.0289(3) Uani 1 1 d . . . N12C N 0.19637(8) 1.5613(2) 0.15763(5) 0.0233(3) Uani 1 1 d . . . N13C N 0.18149(7) 1.54741(19) 0.11327(6) 0.0203(3) Uani 1 1 d . . . N14C N 0.18084(8) 1.5325(2) 0.07323(6) 0.0289(4) Uani 1 1 d . . . N15C N 0.22355(7) 1.4496(2) 0.25024(6) 0.0196(3) Uani 1 1 d . . . H15C H 0.2481(10) 1.521(3) 0.2657(7) 0.023 Uiso 1 1 d . . . C16C C 0.21685(9) 1.2812(2) 0.27281(6) 0.0202(4) Uani 1 1 d . . . H16E H 0.1666 1.2468 0.2733 0.024 Uiso 1 1 calc R . . H16F H 0.2350 1.2862 0.3065 0.024 Uiso 1 1 calc R . . C17C C 0.25854(9) 1.1496(2) 0.24454(7) 0.0204(4) Uani 1 1 d . . . N18C N 0.33757(8) 1.1582(2) 0.25508(6) 0.0271(4) Uani 1 1 d . . . O19C O 0.37094(7) 1.0256(2) 0.25112(6) 0.0442(4) Uani 1 1 d . . . O20C O 0.36030(7) 1.29996(19) 0.26527(6) 0.0397(4) Uani 1 1 d . . . N21C N 0.24826(9) 1.1774(2) 0.19063(6) 0.0289(4) Uani 1 1 d . . . O22C O 0.18649(7) 1.1825(2) 0.17737(5) 0.0367(4) Uani 1 1 d . . . O23C O 0.29974(9) 1.1945(3) 0.16653(5) 0.0507(5) Uani 1 1 d . . . N24C N 0.23627(8) 0.9657(2) 0.25535(7) 0.0299(4) Uani 1 1 d . . . O25C O 0.23175(9) 0.8653(2) 0.22199(6) 0.0509(4) Uani 1 1 d . . . O26C O 0.22597(8) 0.9365(2) 0.29746(6) 0.0441(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1A 0.0139(7) 0.0187(8) 0.0193(8) 0.0009(6) -0.0032(6) -0.0015(6) N2A 0.0189(7) 0.0189(8) 0.0214(8) 0.0007(7) -0.0005(6) -0.0023(6) C3A 0.0176(9) 0.0197(10) 0.0243(10) -0.0028(8) -0.0001(7) -0.0039(7) C4A 0.0166(8) 0.0199(9) 0.0226(10) -0.0031(8) -0.0039(7) -0.0007(7) C5A 0.0161(8) 0.0171(9) 0.0190(9) -0.0020(7) -0.0013(7) 0.0030(7) N6A 0.0253(9) 0.0381(10) 0.0256(9) -0.0023(8) 0.0002(7) -0.0120(8) O7A 0.0432(9) 0.0583(12) 0.0522(11) 0.0213(9) 0.0084(8) -0.0119(8) O8A 0.0208(7) 0.0764(13) 0.0479(10) 0.0086(9) 0.0022(7) -0.0033(8) N9A 0.0210(8) 0.0252(9) 0.0283(10) -0.0058(7) -0.0060(7) -0.0008(7) O10A 0.0355(8) 0.0595(11) 0.0374(9) -0.0049(8) -0.0073(7) -0.0263(8) O11A 0.0367(8) 0.0328(8) 0.0232(8) -0.0019(6) -0.0089(6) 0.0015(6) N12A 0.0184(7) 0.0347(10) 0.0211(9) 0.0047(7) -0.0013(6) 0.0024(7) N13A 0.0236(8) 0.0238(9) 0.0230(9) -0.0022(8) 0.0021(7) -0.0008(7) N14A 0.0403(10) 0.0320(10) 0.0240(9) 0.0050(8) -0.0035(8) 0.0006(8) N15A 0.0121(7) 0.0158(8) 0.0260(9) 0.0001(7) -0.0052(6) 0.0003(6) C16A 0.0158(8) 0.0185(9) 0.0225(10) -0.0014(8) -0.0004(7) -0.0005(7) C17A 0.0188(9) 0.0137(9) 0.0255(10) -0.0001(8) -0.0021(7) 0.0014(7) N18A 0.0288(9) 0.0203(9) 0.0278(9) 0.0062(7) -0.0014(7) 0.0024(7) O19A 0.0356(8) 0.0390(9) 0.0334(8) 0.0103(7) -0.0122(7) 0.0021(7) O20A 0.0389(9) 0.0580(11) 0.0321(8) 0.0097(8) 0.0122(7) 0.0081(8) N21A 0.0244(8) 0.0183(9) 0.0403(11) -0.0033(8) -0.0009(7) 0.0013(7) O22A 0.0514(9) 0.0181(8) 0.0568(10) 0.0085(7) 0.0044(8) 0.0068(7) O23A 0.0656(11) 0.0314(9) 0.0389(10) -0.0121(7) 0.0088(8) 0.0068(8) N24A 0.0180(7) 0.0193(8) 0.0280(9) 0.0020(7) 0.0004(6) -0.0022(6) O25A 0.0204(6) 0.0199(7) 0.0420(8) 0.0022(6) -0.0017(6) 0.0021(6) O26A 0.0272(7) 0.0235(8) 0.0675(11) 0.0022(8) -0.0070(7) -0.0113(6) N1B 0.0188(7) 0.0190(8) 0.0188(8) -0.0012(6) -0.0020(6) 0.0040(6) N2B 0.0237(8) 0.0255(9) 0.0191(8) -0.0027(7) -0.0017(6) 0.0073(7) C2B 0.0242(9) 0.0294(11) 0.0213(10) -0.0026(8) -0.0013(8) 0.0078(8) C4B 0.0235(9) 0.0193(10) 0.0202(10) -0.0006(8) -0.0054(7) 0.0050(7) C5B 0.0221(9) 0.0122(9) 0.0197(9) -0.0017(7) -0.0038(7) -0.0018(7) N6B 0.0350(10) 0.0636(14) 0.0255(10) 0.0086(10) 0.0044(8) 0.0270(10) O7B 0.0688(12) 0.0685(13) 0.0282(9) -0.0049(9) 0.0144(8) 0.0243(10) O8B 0.0233(9) 0.201(3) 0.0510(12) -0.0071(14) -0.0001(8) 0.0259(13) N9B 0.0275(8) 0.0234(9) 0.0260(9) -0.0008(7) -0.0066(7) 0.0060(7) O10B 0.0560(10) 0.0648(12) 0.0399(10) -0.0150(9) -0.0144(8) 0.0450(9) O11B 0.0298(7) 0.0366(8) 0.0202(7) 0.0015(6) -0.0062(6) 0.0013(6) N12B 0.0259(8) 0.0209(8) 0.0238(9) 0.0019(7) 0.0027(7) 0.0014(7) N13B 0.0224(8) 0.0335(10) 0.0216(10) -0.0032(8) 0.0018(7) -0.0037(7) N14B 0.0356(10) 0.0750(16) 0.0229(10) 0.0100(10) 0.0026(8) -0.0049(10) N15B 0.0146(7) 0.0173(8) 0.0274(9) -0.0019(7) -0.0075(6) 0.0004(6) C16B 0.0189(8) 0.0203(10) 0.0194(10) -0.0008(8) -0.0037(7) 0.0024(7) C17B 0.0216(9) 0.0184(9) 0.0233(10) 0.0011(8) -0.0022(7) 0.0019(7) N18B 0.0267(8) 0.0207(9) 0.0214(8) -0.0032(7) -0.0004(7) -0.0030(7) O19B 0.0685(11) 0.0200(8) 0.0492(10) -0.0125(7) -0.0182(8) -0.0018(7) O20B 0.0237(6) 0.0240(7) 0.0224(7) -0.0004(6) -0.0037(5) 0.0004(6) N21B 0.0453(11) 0.0207(9) 0.0346(10) 0.0007(8) -0.0081(9) 0.0070(8) O22B 0.0733(12) 0.0379(10) 0.0641(12) 0.0014(9) 0.0011(10) 0.0348(9) O23B 0.0569(10) 0.0340(9) 0.0514(10) 0.0176(8) 0.0021(9) -0.0068(8) N24B 0.0226(8) 0.0371(10) 0.0315(10) -0.0022(8) 0.0029(7) 0.0053(8) O25B 0.0196(7) 0.0574(11) 0.0425(9) -0.0048(8) -0.0026(6) 0.0010(7) O26B 0.0351(9) 0.0992(16) 0.0306(9) -0.0090(9) 0.0097(7) 0.0040(9) N1C 0.0155(7) 0.0169(8) 0.0200(8) 0.0005(6) -0.0032(6) 0.0010(6) N2C 0.0202(7) 0.0190(8) 0.0207(8) -0.0012(7) -0.0005(6) 0.0012(6) C3C 0.0190(9) 0.0166(9) 0.0225(10) -0.0018(8) -0.0009(7) 0.0013(7) C4C 0.0204(9) 0.0139(9) 0.0194(9) -0.0007(7) -0.0041(7) 0.0011(7) C5C 0.0197(8) 0.0140(9) 0.0187(9) -0.0002(7) -0.0026(7) -0.0033(7) N6C 0.0237(8) 0.0236(9) 0.0242(9) 0.0022(7) 0.0015(7) 0.0050(7) O7C 0.0190(7) 0.0587(11) 0.0465(9) -0.0146(8) -0.0017(6) -0.0010(7) O8C 0.0384(8) 0.0482(10) 0.0367(9) -0.0172(8) 0.0102(7) 0.0004(7) N9C 0.0257(8) 0.0151(8) 0.0238(9) 0.0009(7) -0.0068(7) 0.0018(6) O10C 0.0267(7) 0.0371(9) 0.0374(8) 0.0058(7) -0.0020(6) 0.0159(7) O11C 0.0436(8) 0.0240(7) 0.0190(7) 0.0019(6) -0.0022(6) 0.0079(6) N12C 0.0203(7) 0.0314(9) 0.0181(9) 0.0001(7) -0.0016(6) -0.0015(7) N13C 0.0169(7) 0.0177(8) 0.0262(10) 0.0028(7) 0.0014(6) -0.0002(6) N14C 0.0275(9) 0.0360(10) 0.0231(10) 0.0011(8) 0.0013(7) 0.0034(8) N15C 0.0154(7) 0.0177(8) 0.0252(9) -0.0008(7) -0.0081(6) 0.0005(6) C16C 0.0213(9) 0.0204(10) 0.0189(9) 0.0003(8) -0.0023(7) 0.0022(7) C17C 0.0183(9) 0.0182(9) 0.0246(10) -0.0015(8) -0.0038(7) -0.0001(7) N18C 0.0212(8) 0.0222(9) 0.0377(10) 0.0023(8) -0.0029(7) 0.0016(7) O19C 0.0265(7) 0.0273(8) 0.0788(12) -0.0034(8) 0.0005(8) 0.0097(7) O20C 0.0261(7) 0.0242(8) 0.0682(11) -0.0014(8) -0.0144(7) -0.0034(6) N21C 0.0333(9) 0.0291(10) 0.0244(9) -0.0066(7) 0.0004(8) 0.0021(8) O22C 0.0377(8) 0.0384(9) 0.0332(8) -0.0093(7) -0.0152(7) 0.0027(7) O23C 0.0487(10) 0.0740(13) 0.0299(9) -0.0017(8) 0.0143(8) 0.0039(9) N24C 0.0247(8) 0.0216(9) 0.0434(11) -0.0004(8) 0.0007(8) -0.0012(7) O25C 0.0635(11) 0.0256(9) 0.0632(12) -0.0164(8) -0.0074(9) -0.0085(8) O26C 0.0497(10) 0.0316(9) 0.0514(11) 0.0126(8) 0.0149(8) 0.0018(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1A C5A 1.355(2) . ? N1A N2A 1.3578(19) . ? N1A N15A 1.3876(19) . ? N2A C3A 1.308(2) . ? C3A C4A 1.394(3) . ? C3A N6A 1.454(2) . ? C4A C5A 1.393(2) . ? C4A N9A 1.420(2) . ? C5A N12A 1.373(2) . ? N6A O7A 1.210(2) . ? N6A O8A 1.227(2) . ? N9A O11A 1.219(2) . ? N9A O10A 1.230(2) . ? N12A N13A 1.266(2) . ? N13A N14A 1.118(2) . ? N15A C16A 1.461(2) . ? N15A H15A 0.81(2) . ? C16A C17A 1.520(2) . ? C16A H16A 0.9900 . ? C16A H16B 0.9900 . ? C17A N18A 1.514(2) . ? C17A N21A 1.518(2) . ? C17A N24A 1.522(2) . ? N18A O20A 1.206(2) . ? N18A O19A 1.217(2) . ? N21A O23A 1.209(2) . ? N21A O22A 1.213(2) . ? N24A O25A 1.2081(19) . ? N24A O26A 1.209(2) . ? N1B C5B 1.351(2) . ? N1B N2B 1.356(2) . ? N1B N15B 1.390(2) . ? N2B C2B 1.313(2) . ? C2B C4B 1.395(3) . ? C2B N6B 1.454(2) . ? C4B C5B 1.393(2) . ? C4B N9B 1.427(2) . ? C5B N12B 1.369(2) . ? N6B O8B 1.206(3) . ? N6B O7B 1.211(2) . ? N9B O11B 1.222(2) . ? N9B O10B 1.223(2) . ? N12B N13B 1.259(2) . ? N13B N14B 1.115(2) . ? N15B C16B 1.458(2) . ? N15B H15B 0.83(2) . ? C16B C17B 1.516(3) . ? C16B H16C 0.9900 . ? C16B H16D 0.9900 . ? C17B N24B 1.515(2) . ? C17B N21B 1.518(2) . ? C17B N18B 1.524(2) . ? N18B O20B 1.2024(19) . ? N18B O19B 1.218(2) . ? N21B O22B 1.206(2) . ? N21B O23B 1.211(2) . ? N24B O26B 1.206(2) . ? N24B O25B 1.217(2) . ? N1C C5C 1.351(2) . ? N1C N2C 1.3571(19) . ? N1C N15C 1.3889(19) . ? N2C C3C 1.311(2) . ? C3C C4C 1.401(2) . ? C3C N6C 1.465(2) . ? C4C C5C 1.392(2) . ? C4C N9C 1.420(2) . ? C5C N12C 1.369(2) . ? N6C O8C 1.211(2) . ? N6C O7C 1.219(2) . ? N9C O11C 1.2227(19) . ? N9C O10C 1.2326(19) . ? N12C N13C 1.261(2) . ? N13C N14C 1.116(2) . ? N15C C16C 1.452(2) . ? N15C H15C 0.83(2) . ? C16C C17C 1.518(3) . ? C16C H16E 0.9900 . ? C16C H16F 0.9900 . ? C17C N24C 1.516(2) . ? C17C N21C 1.519(2) . ? C17C N18C 1.523(2) . ? N18C O20C 1.210(2) . ? N18C O19C 1.212(2) . ? N21C O23C 1.202(2) . ? N21C O22C 1.221(2) . ? N24C O25C 1.210(2) . ? N24C O26C 1.210(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 C5A N1A N2A 113.92(13) . . ? C5A N1A N15A 124.58(14) . . ? N2A N1A N15A 121.29(14) . . ? C3A N2A N1A 103.21(14) . . ? N2A C3A C4A 113.53(15) . . ? N2A C3A N6A 118.31(16) . . ? C4A C3A N6A 127.54(16) . . ? C5A C4A C3A 104.68(15) . . ? C5A C4A N9A 126.87(16) . . ? C3A C4A N9A 127.80(16) . . ? N1A C5A N12A 119.48(15) . . ? N1A C5A C4A 104.65(15) . . ? N12A C5A C4A 135.74(17) . . ? O7A N6A O8A 125.95(17) . . ? O7A N6A C3A 118.40(17) . . ? O8A N6A C3A 115.60(17) . . ? O11A N9A O10A 123.81(16) . . ? O11A N9A C4A 118.75(15) . . ? O10A N9A C4A 117.42(16) . . ? N13A N12A C5A 115.21(14) . . ? N14A N13A N12A 170.07(18) . . ? N1A N15A C16A 111.97(13) . . ? N1A N15A H15A 108.2(14) . . ? C16A N15A H15A 112.4(14) . . ? N15A C16A C17A 108.75(14) . . ? N15A C16A H16A 109.9 . . ? C17A C16A H16A 109.9 . . ? N15A C16A H16B 109.9 . . ? C17A C16A H16B 109.9 . . ? H16A C16A H16B 108.3 . . ? N18A C17A N21A 107.01(14) . . ? N18A C17A C16A 111.69(15) . . ? N21A C17A C16A 112.26(14) . . ? N18A C17A N24A 107.32(13) . . ? N21A C17A N24A 106.16(14) . . ? C16A C17A N24A 112.04(14) . . ? O20A N18A O19A 127.70(17) . . ? O20A N18A C17A 118.54(15) . . ? O19A N18A C17A 113.76(15) . . ? O23A N21A O22A 127.57(17) . . ? O23A N21A C17A 114.95(16) . . ? O22A N21A C17A 117.46(16) . . ? O25A N24A O26A 127.20(15) . . ? O25A N24A C17A 115.16(14) . . ? O26A N24A C17A 117.64(15) . . ? C5B N1B N2B 114.14(14) . . ? C5B N1B N15B 124.88(14) . . ? N2B N1B N15B 120.86(14) . . ? C2B N2B N1B 103.19(14) . . ? N2B C2B C4B 113.21(16) . . ? N2B C2B N6B 117.18(16) . . ? C4B C2B N6B 129.44(17) . . ? C5B C4B C2B 104.79(16) . . ? C5B C4B N9B 127.39(16) . . ? C2B C4B N9B 127.81(16) . . ? N1B C5B N12B 117.15(15) . . ? N1B C5B C4B 104.67(15) . . ? N12B C5B C4B 138.14(17) . . ? O8B N6B O7B 125.06(19) . . ? O8B N6B C2B 116.53(19) . . ? O7B N6B C2B 118.41(18) . . ? O11B N9B O10B 123.30(16) . . ? O11B N9B C4B 118.39(15) . . ? O10B N9B C4B 118.30(16) . . ? N13B N12B C5B 117.99(15) . . ? N14B N13B N12B 169.55(19) . . ? N1B N15B C16B 113.31(14) . . ? N1B N15B H15B 110.0(14) . . ? C16B N15B H15B 110.2(14) . . ? N15B C16B C17B 110.76(15) . . ? N15B C16B H16C 109.5 . . ? C17B C16B H16C 109.5 . . ? N15B C16B H16D 109.5 . . ? C17B C16B H16D 109.5 . . ? H16C C16B H16D 108.1 . . ? N24B C17B C16B 111.20(15) . . ? N24B C17B N21B 107.95(14) . . ? C16B C17B N21B 111.04(15) . . ? N24B C17B N18B 107.45(14) . . ? C16B C17B N18B 114.03(14) . . ? N21B C17B N18B 104.80(14) . . ? O20B N18B O19B 126.84(17) . . ? O20B N18B C17B 116.37(15) . . ? O19B N18B C17B 116.79(16) . . ? O22B N21B O23B 127.09(19) . . ? O22B N21B C17B 118.39(18) . . ? O23B N21B C17B 114.48(16) . . ? O26B N24B O25B 127.90(17) . . ? O26B N24B C17B 118.25(17) . . ? O25B N24B C17B 113.85(15) . . ? C5C N1C N2C 114.33(13) . . ? C5C N1C N15C 124.17(14) . . ? N2C N1C N15C 121.50(14) . . ? C3C N2C N1C 102.92(13) . . ? N2C C3C C4C 113.53(15) . . ? N2C C3C N6C 117.46(15) . . ? C4C C3C N6C 128.67(16) . . ? C5C C4C C3C 104.39(15) . . ? C5C C4C N9C 127.55(16) . . ? C3C C4C N9C 127.41(15) . . ? N1C C5C N12C 116.64(15) . . ? N1C C5C C4C 104.82(15) . . ? N12C C5C C4C 138.33(17) . . ? O8C N6C O7C 125.69(16) . . ? O8C N6C C3C 117.72(16) . . ? O7C N6C C3C 116.57(15) . . ? O11C N9C O10C 124.18(16) . . ? O11C N9C C4C 118.13(15) . . ? O10C N9C C4C 117.68(15) . . ? N13C N12C C5C 119.73(14) . . ? N14C N13C N12C 167.66(17) . . ? N1C N15C C16C 113.31(14) . . ? N1C N15C H15C 111.2(14) . . ? C16C N15C H15C 115.2(14) . . ? N15C C16C C17C 109.14(15) . . ? N15C C16C H16E 109.9 . . ? C17C C16C H16E 109.9 . . ? N15C C16C H16F 109.9 . . ? C17C C16C H16F 109.9 . . ? H16E C16C H16F 108.3 . . ? N24C C17C C16C 112.15(15) . . ? N24C C17C N21C 107.31(15) . . ? C16C C17C N21C 110.87(15) . . ? N24C C17C N18C 106.28(14) . . ? C16C C17C N18C 113.17(15) . . ? N21C C17C N18C 106.70(14) . . ? O20C N18C O19C 127.21(16) . . ? O20C N18C C17C 115.38(15) . . ? O19C N18C C17C 117.37(16) . . ? O23C N21C O22C 127.92(18) . . ? O23C N21C C17C 118.32(16) . . ? O22C N21C C17C 113.74(15) . . ? O25C N24C O26C 127.46(18) . . ? O25C N24C C17C 117.83(17) . . ? O26C N24C C17C 114.70(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5A N1A N2A C3A -0.5(2) . . . . ? N15A N1A N2A C3A -175.47(15) . . . . ? N1A N2A C3A C4A -0.2(2) . . . . ? N1A N2A C3A N6A 171.44(16) . . . . ? N2A C3A C4A C5A 0.8(2) . . . . ? N6A C3A C4A C5A -169.96(18) . . . . ? N2A C3A C4A N9A -170.37(17) . . . . ? N6A C3A C4A N9A 18.9(3) . . . . ? N2A N1A C5A N12A 177.39(15) . . . . ? N15A N1A C5A N12A -7.8(3) . . . . ? N2A N1A C5A C4A 0.9(2) . . . . ? N15A N1A C5A C4A 175.76(16) . . . . ? C3A C4A C5A N1A -0.98(19) . . . . ? N9A C4A C5A N1A 170.29(17) . . . . ? C3A C4A C5A N12A -176.6(2) . . . . ? N9A C4A C5A N12A -5.3(3) . . . . ? N2A C3A N6A O7A 51.5(3) . . . . ? C4A C3A N6A O7A -138.2(2) . . . . ? N2A C3A N6A O8A -125.9(2) . . . . ? C4A C3A N6A O8A 44.4(3) . . . . ? C5A C4A N9A O11A 12.5(3) . . . . ? C3A C4A N9A O11A -178.16(18) . . . . ? C5A C4A N9A O10A -166.07(18) . . . . ? C3A C4A N9A O10A 3.2(3) . . . . ? N1A C5A N12A N13A 140.14(17) . . . . ? C4A C5A N12A N13A -44.8(3) . . . . ? C5A N12A N13A N14A -169.1(11) . . . . ? C5A N1A N15A C16A -114.77(18) . . . . ? N2A N1A N15A C16A 59.7(2) . . . . ? N1A N15A C16A C17A 133.88(15) . . . . ? N15A C16A C17A N18A -42.08(19) . . . . ? N15A C16A C17A N21A -162.28(14) . . . . ? N15A C16A C17A N24A 78.37(18) . . . . ? N21A C17A N18A O20A -110.93(18) . . . . ? C16A C17A N18A O20A 125.84(17) . . . . ? N24A C17A N18A O20A 2.7(2) . . . . ? N21A C17A N18A O19A 69.36(18) . . . . ? C16A C17A N18A O19A -53.9(2) . . . . ? N24A C17A N18A O19A -177.05(15) . . . . ? N18A C17A N21A O23A -161.73(16) . . . . ? C16A C17A N21A O23A -38.8(2) . . . . ? N24A C17A N21A O23A 83.89(19) . . . . ? N18A C17A N21A O22A 19.8(2) . . . . ? C16A C17A N21A O22A 142.63(17) . . . . ? N24A C17A N21A O22A -94.63(19) . . . . ? N18A C17A N24A O25A 88.80(18) . . . . ? N21A C17A N24A O25A -157.04(15) . . . . ? C16A C17A N24A O25A -34.2(2) . . . . ? N18A C17A N24A O26A -90.81(19) . . . . ? N21A C17A N24A O26A 23.4(2) . . . . ? C16A C17A N24A O26A 146.23(17) . . . . ? C5B N1B N2B C2B 0.4(2) . . . . ? N15B N1B N2B C2B 176.51(16) . . . . ? N1B N2B C2B C4B -0.8(2) . . . . ? N1B N2B C2B N6B -176.52(17) . . . . ? N2B C2B C4B C5B 0.9(2) . . . . ? N6B C2B C4B C5B 176.0(2) . . . . ? N2B C2B C4B N9B -177.88(18) . . . . ? N6B C2B C4B N9B -2.8(3) . . . . ? N2B N1B C5B N12B -178.09(15) . . . . ? N15B N1B C5B N12B 6.0(2) . . . . ? N2B N1B C5B C4B 0.1(2) . . . . ? N15B N1B C5B C4B -175.79(16) . . . . ? C2B C4B C5B N1B -0.58(19) . . . . ? N9B C4B C5B N1B 178.20(17) . . . . ? C2B C4B C5B N12B 177.1(2) . . . . ? N9B C4B C5B N12B -4.2(4) . . . . ? N2B C2B N6B O8B 133.8(2) . . . . ? C4B C2B N6B O8B -41.1(3) . . . . ? N2B C2B N6B O7B -45.9(3) . . . . ? C4B C2B N6B O7B 139.2(2) . . . . ? C5B C4B N9B O11B -21.7(3) . . . . ? C2B C4B N9B O11B 156.83(19) . . . . ? C5B C4B N9B O10B 159.0(2) . . . . ? C2B C4B N9B O10B -22.5(3) . . . . ? N1B C5B N12B N13B 170.03(16) . . . . ? C4B C5B N12B N13B -7.4(3) . . . . ? C5B N12B N13B N14B -168.4(11) . . . . ? C5B N1B N15B C16B 121.49(18) . . . . ? N2B N1B N15B C16B -54.2(2) . . . . ? N1B N15B C16B C17B -113.96(16) . . . . ? N15B C16B C17B N24B -47.10(19) . . . . ? N15B C16B C17B N21B -167.32(14) . . . . ? N15B C16B C17B N18B 74.57(18) . . . . ? N24B C17B N18B O20B 91.51(17) . . . . ? C16B C17B N18B O20B -32.2(2) . . . . ? N21B C17B N18B O20B -153.83(15) . . . . ? N24B C17B N18B O19B -88.25(19) . . . . ? C16B C17B N18B O19B 148.03(17) . . . . ? N21B C17B N18B O19B 26.4(2) . . . . ? N24B C17B N21B O22B 14.0(2) . . . . ? C16B C17B N21B O22B 136.18(19) . . . . ? N18B C17B N21B O22B -100.3(2) . . . . ? N24B C17B N21B O23B -168.04(16) . . . . ? C16B C17B N21B O23B -45.9(2) . . . . ? N18B C17B N21B O23B 77.65(19) . . . . ? C16B C17B N24B O26B 132.62(19) . . . . ? N21B C17B N24B O26B -105.3(2) . . . . ? N18B C17B N24B O26B 7.2(2) . . . . ? C16B C17B N24B O25B -47.3(2) . . . . ? N21B C17B N24B O25B 74.8(2) . . . . ? N18B C17B N24B O25B -172.69(16) . . . . ? C5C N1C N2C C3C 0.23(19) . . . . ? N15C N1C N2C C3C -179.06(15) . . . . ? N1C N2C C3C C4C -0.4(2) . . . . ? N1C N2C C3C N6C 173.52(14) . . . . ? N2C C3C C4C C5C 0.5(2) . . . . ? N6C C3C C4C C5C -172.64(17) . . . . ? N2C C3C C4C N9C -170.75(17) . . . . ? N6C C3C C4C N9C 16.1(3) . . . . ? N2C N1C C5C N12C 175.83(15) . . . . ? N15C N1C C5C N12C -4.9(2) . . . . ? N2C N1C C5C C4C 0.07(19) . . . . ? N15C N1C C5C C4C 179.33(16) . . . . ? C3C C4C C5C N1C -0.31(19) . . . . ? N9C C4C C5C N1C 170.92(16) . . . . ? C3C C4C C5C N12C -174.6(2) . . . . ? N9C C4C C5C N12C -3.4(4) . . . . ? N2C C3C N6C O8C 56.1(2) . . . . ? C4C C3C N6C O8C -131.0(2) . . . . ? N2C C3C N6C O7C -122.27(19) . . . . ? C4C C3C N6C O7C 50.6(3) . . . . ? C5C C4C N9C O11C 12.6(3) . . . . ? C3C C4C N9C O11C -178.11(17) . . . . ? C5C C4C N9C O10C -166.54(17) . . . . ? C3C C4C N9C O10C 2.7(3) . . . . ? N1C C5C N12C N13C 155.71(16) . . . . ? C4C C5C N12C N13C -30.5(3) . . . . ? C5C N12C N13C N14C -175.4(8) . . . . ? C5C N1C N15C C16C -123.45(18) . . . . ? N2C N1C N15C C16C 55.8(2) . . . . ? N1C N15C C16C C17C 121.34(15) . . . . ? N15C C16C C17C N24C -161.77(14) . . . . ? N15C C16C C17C N21C -41.84(19) . . . . ? N15C C16C C17C N18C 78.01(18) . . . . ? N24C C17C N18C O20C -154.70(17) . . . . ? C16C C17C N18C O20C -31.2(2) . . . . ? N21C C17C N18C O20C 91.02(19) . . . . ? N24C C17C N18C O19C 27.3(2) . . . . ? C16C C17C N18C O19C 150.84(18) . . . . ? N21C C17C N18C O19C -87.0(2) . . . . ? N24C C17C N21C O23C -111.29(19) . . . . ? C16C C17C N21C O23C 125.94(19) . . . . ? N18C C17C N21C O23C 2.3(2) . . . . ? N24C C17C N21C O22C 69.95(19) . . . . ? C16C C17C N21C O22C -52.8(2) . . . . ? N18C C17C N21C O22C -176.47(16) . . . . ? C16C C17C N24C O25C 139.28(17) . . . . ? N21C C17C N24C O25C 17.3(2) . . . . ? N18C C17C N24C O25C -96.57(19) . . . . ? C16C C17C N24C O26C -41.7(2) . . . . ? N21C C17C N24C O26C -163.73(16) . . . . ? N18C C17C N24C O26C 82.41(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N15A H15A O10C 0.81(2) 2.52(2) 3.204(2) 142.8(18) 3_575 N15B H15B O10A 0.83(2) 2.31(2) 3.036(2) 145.8(18) . N15C H15C O11B 0.83(2) 2.39(2) 3.197(2) 162.9(18) 2_665 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.271 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 948453' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shrv242 _audit_creation_date 2013-06-11 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; 3,4-dinitro-1H-pyrazole-1,5-diamine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C3 H4 N6 O4' _chemical_formula_sum 'C3 H4 N6 O4' _chemical_formula_weight 188.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 12.7023(12) _cell_length_b 8.0688(8) _cell_length_c 13.0694(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1339.5(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.866 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.170 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.9108 _exptl_absorpt_correction_T_max 0.9367 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11756 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0132 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 26.45 _reflns_number_total 1379 _reflns_number_gt 1296 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_structure_refinement 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_molecular_graphics 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.5097P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.037(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1379 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0703 _refine_ls_wR_factor_gt 0.0689 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 0.16060(7) 0.20926(11) 0.43408(7) 0.0184(2) Uani 1 1 d . . . N2 N 0.08597(7) 0.14763(11) 0.49940(7) 0.0171(2) Uani 1 1 d . . . C3 C 0.14108(8) 0.06909(13) 0.56825(8) 0.0158(2) Uani 1 1 d . . . C4 C 0.25034(8) 0.07427(13) 0.54950(8) 0.0177(2) Uani 1 1 d . . . C5 C 0.26057(8) 0.17021(13) 0.46044(8) 0.0183(2) Uani 1 1 d . . . N6 N 0.13485(8) 0.30263(13) 0.34829(8) 0.0230(2) Uani 1 1 d . . . H6A H 0.1083(12) 0.232(2) 0.3028(12) 0.035 Uiso 1 1 d . . . H6B H 0.0846(12) 0.373(2) 0.3680(12) 0.035 Uiso 1 1 d . . . N7 N 0.08380(7) -0.01968(12) 0.64689(7) 0.0170(2) Uani 1 1 d . . . O8 O 0.00806(6) 0.05018(11) 0.68530(6) 0.0250(2) Uani 1 1 d . . . O9 O 0.11307(7) -0.15985(10) 0.66796(6) 0.0249(2) Uani 1 1 d . . . N10 N 0.33369(7) 0.01401(12) 0.60923(8) 0.0207(2) Uani 1 1 d . . . O11 O 0.31495(7) -0.03739(13) 0.69583(7) 0.0329(3) Uani 1 1 d . . . O12 O 0.42279(6) 0.01671(11) 0.57052(7) 0.0273(2) Uani 1 1 d . . . N13 N 0.34430(8) 0.22354(14) 0.40871(9) 0.0256(2) Uani 1 1 d . . . H13A H 0.4063(14) 0.200(2) 0.4294(13) 0.038 Uiso 1 1 d . . . H13B H 0.3334(13) 0.282(2) 0.3548(14) 0.038 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 0.0169(5) 0.0205(5) 0.0179(4) 0.0023(4) 0.0012(3) -0.0027(4) N2 0.0160(5) 0.0178(5) 0.0176(4) -0.0004(4) 0.0018(3) -0.0021(3) C3 0.0146(5) 0.0157(5) 0.0171(5) -0.0025(4) 0.0002(4) -0.0015(4) C4 0.0136(5) 0.0196(5) 0.0198(5) -0.0028(4) 0.0005(4) -0.0014(4) C5 0.0170(5) 0.0185(5) 0.0195(5) -0.0053(4) 0.0012(4) -0.0031(4) N6 0.0274(5) 0.0220(5) 0.0197(5) 0.0048(4) 0.0004(4) -0.0004(4) N7 0.0146(5) 0.0204(5) 0.0160(4) -0.0013(4) -0.0011(3) -0.0026(3) O8 0.0190(4) 0.0341(5) 0.0217(4) -0.0018(3) 0.0055(3) 0.0019(3) O9 0.0269(4) 0.0201(4) 0.0277(4) 0.0049(3) -0.0007(3) -0.0016(3) N10 0.0155(4) 0.0212(5) 0.0254(5) -0.0022(4) -0.0025(4) -0.0007(4) O11 0.0231(5) 0.0468(6) 0.0288(5) 0.0128(4) -0.0058(4) -0.0031(4) O12 0.0131(4) 0.0336(5) 0.0351(5) -0.0061(4) 0.0008(3) 0.0017(3) N13 0.0188(5) 0.0332(6) 0.0247(5) 0.0011(4) 0.0047(4) -0.0063(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.3529(14) . ? N1 N2 1.3693(12) . ? N1 N6 1.3899(13) . ? N2 C3 1.3043(14) . ? C3 C4 1.4100(15) . ? C3 N7 1.4487(14) . ? C4 N10 1.4024(14) . ? C4 C5 1.4039(16) . ? C5 N13 1.3318(15) . ? N6 H6A 0.892(17) . ? N6 H6B 0.893(17) . ? N7 O9 1.2219(13) . ? N7 O8 1.2229(12) . ? N10 O11 1.2287(13) . ? N10 O12 1.2399(13) . ? N13 H13A 0.854(18) . ? N13 H13B 0.858(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 N2 113.98(9) . . ? C5 N1 N6 123.54(9) . . ? N2 N1 N6 122.47(9) . . ? C3 N2 N1 103.59(8) . . ? N2 C3 C4 113.20(10) . . ? N2 C3 N7 117.40(9) . . ? C4 C3 N7 129.22(10) . . ? N10 C4 C5 125.65(10) . . ? N10 C4 C3 129.50(10) . . ? C5 C4 C3 104.57(9) . . ? N13 C5 N1 123.03(11) . . ? N13 C5 C4 132.30(11) . . ? N1 C5 C4 104.64(9) . . ? N1 N6 H6A 106.1(10) . . ? N1 N6 H6B 106.4(10) . . ? H6A N6 H6B 109.4(14) . . ? O9 N7 O8 125.00(9) . . ? O9 N7 C3 117.69(9) . . ? O8 N7 C3 117.28(9) . . ? O11 N10 O12 123.96(10) . . ? O11 N10 C4 118.91(9) . . ? O12 N10 C4 117.13(10) . . ? C5 N13 H13A 120.3(11) . . ? C5 N13 H13B 117.7(11) . . ? H13A N13 H13B 122.0(16) . . ? 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 C5 N1 N2 C3 0.30(12) . . . . ? N6 N1 N2 C3 179.95(10) . . . . ? N1 N2 C3 C4 -1.07(12) . . . . ? N1 N2 C3 N7 -176.61(9) . . . . ? N2 C3 C4 N10 175.50(10) . . . . ? N7 C3 C4 N10 -9.60(19) . . . . ? N2 C3 C4 C5 1.42(12) . . . . ? N7 C3 C4 C5 176.31(10) . . . . ? N2 N1 C5 N13 -177.51(10) . . . . ? N6 N1 C5 N13 2.84(17) . . . . ? N2 N1 C5 C4 0.55(12) . . . . ? N6 N1 C5 C4 -179.09(10) . . . . ? N10 C4 C5 N13 2.3(2) . . . . ? C3 C4 C5 N13 176.70(12) . . . . ? N10 C4 C5 N1 -175.49(10) . . . . ? C3 C4 C5 N1 -1.11(11) . . . . ? N2 C3 N7 O9 134.87(10) . . . . ? C4 C3 N7 O9 -39.84(16) . . . . ? N2 C3 N7 O8 -43.33(13) . . . . ? C4 C3 N7 O8 141.96(11) . . . . ? C5 C4 N10 O11 164.66(11) . . . . ? C3 C4 N10 O11 -8.29(17) . . . . ? C5 C4 N10 O12 -15.13(16) . . . . ? C3 C4 N10 O12 171.92(11) . . . . ? 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 O11 0.892(17) 2.316(17) 2.9928(14) 132.7(13) 4_554 N6 H6B O12 0.893(17) 2.379(17) 3.2414(14) 162.3(14) 2_456 N13 H13A O12 0.854(18) 2.374(17) 2.8725(16) 117.7(14) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.370 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 948454'