# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cnu1040 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Hydrazinium_nitroformate _chemical_melting_point ? _chemical_formula_moiety 'C N3 O6, H5 N2' _chemical_formula_sum 'C H5 N5 O6' _chemical_formula_weight 183.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.0012(5) _cell_length_b 11.8726(7) _cell_length_c 14.0979(9) _cell_angle_alpha 90.00 _cell_angle_beta 104.4410(10) _cell_angle_gamma 90.00 _cell_volume 1296.92(14) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5087 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 27.30 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_min 0.19 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_max 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.875 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.190 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19211 _diffrn_reflns_av_R_equivalents 0.0626 _diffrn_reflns_av_sigmaI/netI 0.0391 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 28.24 _reflns_number_total 3207 _reflns_number_gt 2367 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0565P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3207 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.1000 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.25138(17) 0.81708(11) 0.79602(10) 0.0227(3) Uani 1 1 d . . . N2 N 0.08720(14) 0.77001(9) 0.74862(8) 0.0234(3) Uani 1 1 d . . . O3 O -0.02212(13) 0.75977(9) 0.79550(8) 0.0356(3) Uani 1 1 d . . . O4 O 0.06103(14) 0.74023(10) 0.66303(8) 0.0384(3) Uani 1 1 d . . . N5 N 0.39881(14) 0.76790(9) 0.77749(8) 0.0230(3) Uani 1 1 d . . . O6 O 0.38017(13) 0.68077(8) 0.72810(8) 0.0327(3) Uani 1 1 d . . . O7 O 0.54268(13) 0.81056(9) 0.81059(8) 0.0338(3) Uani 1 1 d . . . N8 N 0.25557(15) 0.90724(9) 0.85887(8) 0.0241(3) Uani 1 1 d . . . O9 O 0.39479(14) 0.94226(9) 0.91087(8) 0.0389(3) Uani 1 1 d . . . O10 O 0.11780(13) 0.95308(8) 0.86150(8) 0.0349(3) Uani 1 1 d . . . N11 N 0.23619(16) 0.65989(13) 0.51269(11) 0.0291(3) Uani 1 1 d . . . H11A H 0.148(3) 0.6703(17) 0.4563(18) 0.070(7) Uiso 1 1 d . . . H11B H 0.214(3) 0.599(2) 0.5392(17) 0.068(7) Uiso 1 1 d . . . H11C H 0.228(3) 0.709(2) 0.5550(16) 0.062(7) Uiso 1 1 d . . . N12 N 0.40756(17) 0.66180(14) 0.49943(11) 0.0326(3) Uani 1 1 d . . . H12A H 0.419(3) 0.722(2) 0.4822(16) 0.072(8) Uiso 1 1 d . . . H12B H 0.402(3) 0.6201(18) 0.4491(16) 0.061(7) Uiso 1 1 d . . . C13 C 0.2583(2) 1.03137(12) 0.50474(10) 0.0288(3) Uani 1 1 d . . . N14 N 0.24579(17) 0.98810(11) 0.41369(9) 0.0316(3) Uani 1 1 d . . . O15 O 0.16705(17) 1.04611(10) 0.34300(8) 0.0498(3) Uani 1 1 d . . . O16 O 0.30909(18) 0.89600(10) 0.40194(9) 0.0487(3) Uani 1 1 d . . . N17 N 0.32512(17) 0.97857(10) 0.59254(9) 0.0308(3) Uani 1 1 d . . . O18 O 0.38034(18) 0.88121(9) 0.59478(8) 0.0485(3) Uani 1 1 d . . . O19 O 0.32818(17) 1.03336(10) 0.66784(8) 0.0478(3) Uani 1 1 d . . . N20 N 0.18336(16) 1.14209(10) 0.50941(8) 0.0274(3) Uani 1 1 d . . . O21 O 0.26241(15) 1.22329(9) 0.49209(9) 0.0429(3) Uani 1 1 d . . . O22 O 0.04617(16) 1.14730(10) 0.53182(9) 0.0449(3) Uani 1 1 d . . . N23 N 0.81596(18) 1.11639(13) 0.82101(11) 0.0325(3) Uani 1 1 d . . . H23A H 0.903(3) 1.1446(16) 0.8751(15) 0.053(6) Uiso 1 1 d . . . H23B H 0.744(3) 1.177(2) 0.7876(18) 0.086(8) Uiso 1 1 d . . . H23C H 0.856(4) 1.086(2) 0.776(2) 0.093(9) Uiso 1 1 d . . . N24 N 0.7104(2) 1.03695(14) 0.85479(14) 0.0455(4) Uani 1 1 d . . . H24A H 0.638(5) 1.087(3) 0.880(3) 0.143(13) Uiso 1 1 d . . . H24B H 0.655(3) 1.001(2) 0.8064(19) 0.084(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0206(7) 0.0241(7) 0.0233(7) -0.0052(5) 0.0050(5) -0.0008(5) N2 0.0217(6) 0.0232(6) 0.0241(6) -0.0015(5) 0.0035(5) 0.0005(4) O3 0.0286(6) 0.0441(6) 0.0373(6) -0.0027(5) 0.0142(5) -0.0094(5) O4 0.0306(6) 0.0574(7) 0.0241(6) -0.0134(5) 0.0014(5) 0.0002(5) N5 0.0220(6) 0.0271(6) 0.0199(6) 0.0010(5) 0.0051(5) 0.0015(5) O6 0.0319(6) 0.0308(5) 0.0357(6) -0.0106(5) 0.0090(5) 0.0044(4) O7 0.0188(5) 0.0479(6) 0.0336(6) -0.0052(5) 0.0043(4) -0.0048(4) N8 0.0263(6) 0.0231(6) 0.0232(6) -0.0016(5) 0.0067(5) -0.0016(5) O9 0.0296(6) 0.0431(6) 0.0403(7) -0.0188(5) 0.0016(5) -0.0078(5) O10 0.0308(6) 0.0294(5) 0.0453(7) -0.0077(5) 0.0112(5) 0.0064(4) N11 0.0251(7) 0.0341(7) 0.0263(7) -0.0004(6) 0.0029(5) 0.0020(5) N12 0.0282(7) 0.0375(8) 0.0338(8) 0.0046(7) 0.0109(6) 0.0026(6) C13 0.0383(8) 0.0241(7) 0.0231(7) -0.0018(5) 0.0062(6) 0.0041(6) N14 0.0371(7) 0.0333(7) 0.0237(6) -0.0018(5) 0.0060(5) 0.0070(5) O15 0.0704(9) 0.0497(7) 0.0230(6) 0.0010(5) -0.0002(6) 0.0244(6) O16 0.0718(9) 0.0402(6) 0.0339(7) -0.0055(5) 0.0125(6) 0.0250(6) N17 0.0401(7) 0.0257(6) 0.0260(7) 0.0009(5) 0.0072(5) -0.0016(5) O18 0.0771(10) 0.0311(6) 0.0346(7) 0.0067(5) 0.0088(6) 0.0142(6) O19 0.0787(10) 0.0401(7) 0.0222(6) -0.0032(5) 0.0082(6) 0.0060(6) N20 0.0310(7) 0.0264(6) 0.0233(6) -0.0026(5) 0.0040(5) 0.0009(5) O21 0.0456(7) 0.0285(6) 0.0525(8) 0.0004(5) 0.0083(6) -0.0087(5) O22 0.0409(7) 0.0458(7) 0.0539(8) -0.0002(6) 0.0227(6) 0.0077(5) N23 0.0273(7) 0.0405(8) 0.0298(7) 0.0058(6) 0.0072(6) -0.0037(6) N24 0.0338(8) 0.0425(9) 0.0555(11) 0.0177(8) 0.0025(7) -0.0109(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N8 1.3847(17) . ? C1 N5 1.3980(17) . ? C1 N2 1.4307(17) . ? N2 O4 1.2242(15) . ? N2 O3 1.2267(14) . ? N5 O6 1.2350(14) . ? N5 O7 1.2376(15) . ? N8 O10 1.2381(15) . ? N8 O9 1.2425(15) . ? N11 N12 1.4294(18) . ? N11 H11A 0.93(2) . ? N11 H11B 0.86(2) . ? N11 H11C 0.85(2) . ? N12 H12A 0.77(3) . ? N12 H12B 0.86(2) . ? C13 N14 1.3628(18) . ? C13 N17 1.3715(18) . ? C13 N20 1.4533(18) . ? N14 O16 1.2335(16) . ? N14 O15 1.2455(16) . ? N17 O18 1.2351(15) . ? N17 O19 1.2401(15) . ? N20 O21 1.2108(16) . ? N20 O22 1.2171(16) . ? N23 N24 1.4247(19) . ? N23 H23A 0.96(2) . ? N23 H23B 0.97(3) . ? N23 H23C 0.86(3) . ? N24 H24A 0.96(4) . ? N24 H24B 0.83(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N8 C1 N5 123.75(12) . . ? N8 C1 N2 118.27(11) . . ? N5 C1 N2 117.96(11) . . ? O4 N2 O3 122.19(12) . . ? O4 N2 C1 118.98(12) . . ? O3 N2 C1 118.82(11) . . ? O6 N5 O7 121.71(12) . . ? O6 N5 C1 117.80(11) . . ? O7 N5 C1 120.49(11) . . ? O10 N8 O9 120.61(11) . . ? O10 N8 C1 118.64(11) . . ? O9 N8 C1 120.75(11) . . ? N12 N11 H11A 115.6(14) . . ? N12 N11 H11B 112.4(15) . . ? H11A N11 H11B 107(2) . . ? N12 N11 H11C 109.0(14) . . ? H11A N11 H11C 109(2) . . ? H11B N11 H11C 102(2) . . ? N11 N12 H12A 104.3(18) . . ? N11 N12 H12B 104.1(15) . . ? H12A N12 H12B 105(2) . . ? N14 C13 N17 126.76(13) . . ? N14 C13 N20 116.71(12) . . ? N17 C13 N20 116.41(12) . . ? O16 N14 O15 121.69(12) . . ? O16 N14 C13 121.63(13) . . ? O15 N14 C13 116.68(12) . . ? O18 N17 O19 122.59(12) . . ? O18 N17 C13 120.48(12) . . ? O19 N17 C13 116.93(12) . . ? O21 N20 O22 124.20(13) . . ? O21 N20 C13 117.95(13) . . ? O22 N20 C13 117.83(12) . . ? N24 N23 H23A 109.9(11) . . ? N24 N23 H23B 108.8(15) . . ? H23A N23 H23B 110.8(18) . . ? N24 N23 H23C 109.1(18) . . ? H23A N23 H23C 114(2) . . ? H23B N23 H23C 104(2) . . ? N23 N24 H24A 101(2) . . ? N23 N24 H24B 107.4(18) . . ? H24A N24 H24B 112(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 N8 C1 N2 O4 140.60(13) . . . . ? N5 C1 N2 O4 -40.55(18) . . . . ? N8 C1 N2 O3 -40.14(17) . . . . ? N5 C1 N2 O3 138.71(13) . . . . ? N8 C1 N5 O6 172.64(12) . . . . ? N2 C1 N5 O6 -6.15(18) . . . . ? N8 C1 N5 O7 -6.8(2) . . . . ? N2 C1 N5 O7 174.44(11) . . . . ? N5 C1 N8 O10 171.60(12) . . . . ? N2 C1 N8 O10 -9.62(18) . . . . ? N5 C1 N8 O9 -7.7(2) . . . . ? N2 C1 N8 O9 171.11(12) . . . . ? N17 C13 N14 O16 -6.0(2) . . . . ? N20 C13 N14 O16 178.18(14) . . . . ? N17 C13 N14 O15 173.85(15) . . . . ? N20 C13 N14 O15 -1.9(2) . . . . ? N14 C13 N17 O18 -0.8(2) . . . . ? N20 C13 N17 O18 174.97(14) . . . . ? N14 C13 N17 O19 178.57(15) . . . . ? N20 C13 N17 O19 -5.6(2) . . . . ? N14 C13 N20 O21 -76.73(17) . . . . ? N17 C13 N20 O21 107.04(15) . . . . ? N14 C13 N20 O22 104.25(16) . . . . ? N17 C13 N20 O22 -71.98(17) . . . . ? 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 N11 H11A O7 0.93(2) 2.03(2) 2.9048(18) 156.3(19) 4_575 N11 H11A O9 0.93(2) 2.38(2) 3.0062(18) 124.6(17) 4_575 N11 H11B O9 0.86(2) 2.24(3) 3.0821(19) 169(2) 2_546 N11 H11B O10 0.86(2) 2.41(2) 3.0832(18) 136(2) 2_546 N11 H11B N8 0.86(2) 2.67(3) 3.4958(19) 163(2) 2_546 N11 H11C O4 0.85(2) 2.29(2) 2.9746(18) 137.5(19) . N11 H11C O18 0.85(2) 2.37(2) 2.9847(19) 129.3(18) . N11 H11C O6 0.85(2) 2.46(2) 2.9776(18) 119.7(18) . N12 H12A O16 0.77(3) 2.41(3) 3.1147(19) 153(2) . N12 H12A O18 0.77(3) 2.53(2) 2.964(2) 117(2) . N12 H12A O21 0.77(3) 2.57(2) 2.9481(18) 112(2) 3_676 N12 H12B O10 0.86(2) 2.52(2) 3.1784(18) 134.8(19) 4_675 N12 H12B N24 0.86(2) 2.56(2) 3.257(2) 138.7(19) 4_575 N23 H23A N12 0.96(2) 2.03(2) 2.966(2) 165.1(16) 2_656 N23 H23B O3 0.97(3) 2.11(3) 3.0327(18) 159(2) 2_556 N23 H23C O15 0.86(3) 2.27(3) 3.040(2) 149(2) 3_676 N23 H23C O16 0.86(3) 2.54(3) 3.0551(19) 120(2) 3_676 N24 H24A O4 0.96(4) 2.40(4) 3.215(2) 143(3) 2_556 N24 H24B O7 0.83(3) 2.44(3) 2.999(2) 125(2) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.269 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.080 _database_code_depnum_ccdc_archive 'CCDC 955657' ####################################################################### # # 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_cnu1090 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Hydrazinium_dinitromethanide _chemical_melting_point ? _chemical_formula_moiety 'C H N2 O4, H5 N2' _chemical_formula_sum 'C H6 N4 O4' _chemical_formula_weight 138.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 3.701(3) _cell_length_b 13.875(11) _cell_length_c 10.753(9) _cell_angle_alpha 90.00 _cell_angle_beta 98.833(9) _cell_angle_gamma 90.00 _cell_volume 545.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1061 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 21.30 _exptl_crystal_description blcok _exptl_crystal_colour yellow _exptl_crystal_size_min 0.22 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_max 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.681 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9535 _diffrn_reflns_av_R_equivalents 0.1425 _diffrn_reflns_av_sigmaI/netI 0.1058 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 28.54 _reflns_number_total 1360 _reflns_number_gt 569 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0420P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1360 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1428 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1064 _refine_ls_wR_factor_gt 0.0843 _refine_ls_goodness_of_fit_ref 0.856 _refine_ls_restrained_S_all 0.856 _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 -0.1088(5) 0.09939(17) 0.62929(19) 0.0415(6) Uani 1 1 d . . . C2 C -0.1384(6) 0.00549(19) 0.6581(2) 0.0396(7) Uani 1 1 d . . . H2 H -0.2899 -0.0325 0.6009 0.048 Uiso 1 1 calc R . . N3 N 0.0350(5) -0.03851(17) 0.76404(18) 0.0415(6) Uani 1 1 d . . . O4 O -0.2864(5) 0.12679(13) 0.52519(16) 0.0566(6) Uani 1 1 d . . . O5 O 0.0799(5) 0.16000(13) 0.69736(16) 0.0533(6) Uani 1 1 d . . . O6 O 0.2486(5) 0.00543(13) 0.84829(15) 0.0525(6) Uani 1 1 d . . . O7 O -0.0216(5) -0.12725(15) 0.77397(17) 0.0538(6) Uani 1 1 d . . . N8 N 0.4112(6) 0.1714(2) 1.0215(2) 0.0413(6) Uani 1 1 d . . . H8A H 0.470(7) 0.226(2) 1.089(3) 0.080(10) Uiso 1 1 d . . . H8B H 0.478(8) 0.102(2) 1.052(3) 0.089(11) Uiso 1 1 d . . . H8C H 0.184(9) 0.174(2) 0.994(3) 0.069(9) Uiso 1 1 d . . . N9 N 0.6351(6) 0.1969(2) 0.9273(2) 0.0448(7) Uani 1 1 d . . . H9A H 0.572(7) 0.271(2) 0.912(3) 0.083(11) Uiso 1 1 d . . . H9B H 0.577(8) 0.163(2) 0.872(3) 0.071(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0348(11) 0.0541(17) 0.0330(12) -0.0020(11) -0.0035(9) -0.0015(10) C2 0.0358(13) 0.0472(18) 0.0316(14) -0.0008(12) -0.0085(11) -0.0046(12) N3 0.0347(11) 0.0566(18) 0.0320(12) -0.0020(11) 0.0009(9) -0.0001(11) O4 0.0604(11) 0.0625(13) 0.0382(10) 0.0089(9) -0.0200(9) -0.0062(10) O5 0.0587(12) 0.0537(13) 0.0405(11) -0.0040(9) -0.0154(9) -0.0088(9) O6 0.0544(11) 0.0592(13) 0.0366(10) -0.0010(9) -0.0164(9) -0.0006(10) O7 0.0600(12) 0.0493(13) 0.0479(12) 0.0082(10) -0.0048(9) -0.0038(11) N8 0.0281(12) 0.0570(17) 0.0372(13) -0.0007(12) 0.0003(10) 0.0015(12) N9 0.0362(12) 0.0636(19) 0.0332(13) -0.0033(13) 0.0013(10) -0.0026(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 O5 1.254(2) . ? N1 O4 1.266(2) . ? N1 C2 1.348(3) . ? C2 N3 1.363(3) . ? C2 H2 0.9300 . ? N3 O7 1.256(3) . ? N3 O6 1.264(2) . ? N8 N9 1.448(3) . ? N8 H8A 1.05(3) . ? N8 H8B 1.04(3) . ? N8 H8C 0.85(3) . ? N9 H9A 1.06(3) . ? N9 H9B 0.76(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 N1 O4 118.8(2) . . ? O5 N1 C2 124.9(2) . . ? O4 N1 C2 116.4(2) . . ? N1 C2 N3 125.5(2) . . ? N1 C2 H2 117.2 . . ? N3 C2 H2 117.2 . . ? O7 N3 O6 120.4(2) . . ? O7 N3 C2 116.5(2) . . ? O6 N3 C2 123.0(2) . . ? N9 N8 H8A 103.1(15) . . ? N9 N8 H8B 108.4(17) . . ? H8A N8 H8B 116(2) . . ? N9 N8 H8C 113.0(19) . . ? H8A N8 H8C 108(2) . . ? H8B N8 H8C 109(3) . . ? N8 N9 H9A 101.9(15) . . ? N8 N9 H9B 106(3) . . ? H9A N9 H9B 116(3) . . ? 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 N8 H8A O5 1.05(3) 1.97(3) 3.012(4) 173(2) 4_666 N8 H8A O4 1.05(3) 2.31(3) 2.895(4) 114(2) 4_666 N8 H8A N1 1.05(3) 2.49(3) 3.389(4) 144(2) 4_666 N8 H8B O6 1.04(3) 2.01(3) 3.004(3) 159(2) 3_657 N8 H8B N3 1.04(3) 2.61(3) 3.386(4) 131(2) 3_657 N9 H9A O4 1.06(3) 2.39(3) 3.167(4) 129(2) 4_666 N9 H9A O7 1.06(3) 2.43(3) 3.245(4) 132(2) 2_556 N9 H9B O5 0.76(3) 2.42(3) 3.006(3) 135(3) . N9 H9B O6 0.76(3) 2.50(3) 3.075(4) 134(3) . _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.54 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.177 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 955658'