# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_ap19 _database_code_depnum_ccdc_archive 'CCDC 874203' #TrackingRef 'web_deposit_cif_file_0_AnnePetitjean_1333204486.ap19.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 N6 O5' _chemical_formula_weight 386.37 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 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 7.5319(8) _cell_length_b 15.1775(19) _cell_length_c 15.610(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.919(3) _cell_angle_gamma 90.00 _cell_volume 1762.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 1743 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 25.67 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9782 _exptl_absorpt_correction_T_max 0.9869 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9428 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3451 _reflns_number_gt 2336 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0476P)^2^+0.1340P] 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 0.0046(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3451 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1084 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.32916(18) 0.69985(8) 0.01567(9) 0.0493(4) Uani 1 1 d . . . O2 O 0.04457(18) 0.64735(7) 0.26149(8) 0.0444(4) Uani 1 1 d . . . O3 O -0.06905(18) 0.35079(7) 0.25815(8) 0.0439(3) Uani 1 1 d . . . O4 O 0.12956(19) 0.24809(8) 0.00301(9) 0.0499(4) Uani 1 1 d . . . O5 O 0.17160(18) 0.48094(8) 0.22428(9) 0.0401(3) Uani 1 1 d . . . H5H H 0.086(4) 0.4881(16) 0.2582(17) 0.084(9) Uiso 1 1 d . . . N1 N 0.21338(18) 0.47588(9) 0.04082(9) 0.0352(4) Uani 1 1 d . . . N2 N 0.20234(19) 0.63491(9) 0.12285(9) 0.0369(4) Uani 1 1 d . . . H2B H 0.1747 0.5852 0.1465 0.044 Uiso 1 1 calc R . . N3 N 0.1023(2) 0.72806(9) 0.22910(11) 0.0430(4) Uani 1 1 d . . . N4 N -0.07577(19) 0.50543(9) 0.34115(10) 0.0361(4) Uani 1 1 d . . . N5 N -0.0745(2) 0.26441(9) 0.22256(11) 0.0441(4) Uani 1 1 d . . . N6 N 0.08071(19) 0.33219(9) 0.11743(10) 0.0368(4) Uani 1 1 d . . . H6A H 0.0942 0.3838 0.1433 0.044 Uiso 1 1 calc R . . C1 C 0.2082(2) 0.39898(12) -0.00192(12) 0.0365(4) Uani 1 1 d . . . C2 C 0.2544(2) 0.39086(13) -0.08404(13) 0.0442(5) Uani 1 1 d . . . H2A H 0.2488 0.3352 -0.1121 0.053 Uiso 1 1 calc R . . C3 C 0.3085(3) 0.46440(14) -0.12449(13) 0.0472(5) Uani 1 1 d . . . H3A H 0.3395 0.4605 -0.1811 0.057 Uiso 1 1 calc R . . C4 C 0.3169(2) 0.54425(13) -0.08109(13) 0.0431(5) Uani 1 1 d . . . H4A H 0.3546 0.5962 -0.1071 0.052 Uiso 1 1 calc R . . C5 C 0.2693(2) 0.54676(11) 0.00089(12) 0.0360(4) Uani 1 1 d . . . C6 C 0.2718(2) 0.63360(12) 0.04727(12) 0.0371(4) Uani 1 1 d . . . C7 C 0.1753(2) 0.71413(11) 0.16229(13) 0.0413(5) Uani 1 1 d . . . H7A H 0.2168 0.7650 0.1360 0.050 Uiso 1 1 calc R . . C8 C 0.0050(3) 0.66252(12) 0.34553(12) 0.0452(5) Uani 1 1 d . . . H8A H -0.0707 0.7159 0.3451 0.054 Uiso 1 1 calc R . . H8B H 0.1181 0.6731 0.3858 0.054 Uiso 1 1 calc R . . C9 C -0.0918(2) 0.58536(11) 0.37711(11) 0.0360(4) Uani 1 1 d . . . C10 C -0.1893(3) 0.59916(12) 0.44338(12) 0.0425(5) Uani 1 1 d . . . H10A H -0.1970 0.6564 0.4672 0.051 Uiso 1 1 calc R . . C11 C -0.2759(3) 0.52883(13) 0.47484(13) 0.0476(5) Uani 1 1 d . . . H11A H -0.3427 0.5367 0.5211 0.057 Uiso 1 1 calc R . . C12 C -0.2637(3) 0.44701(12) 0.43784(12) 0.0436(5) Uani 1 1 d . . . H12A H -0.3237 0.3977 0.4576 0.052 Uiso 1 1 calc R . . C13 C -0.1635(2) 0.43776(11) 0.37191(11) 0.0356(4) Uani 1 1 d . . . C14 C -0.1488(3) 0.34696(12) 0.33454(13) 0.0430(5) Uani 1 1 d . . . H14A H -0.0753 0.3090 0.3779 0.052 Uiso 1 1 calc R . . H14B H -0.2700 0.3205 0.3210 0.052 Uiso 1 1 calc R . . C15 C 0.0014(3) 0.26384(11) 0.15525(13) 0.0415(5) Uani 1 1 d . . . H15A H 0.0037 0.2084 0.1272 0.050 Uiso 1 1 calc R . . C16 C 0.1385(2) 0.31982(11) 0.03962(12) 0.0378(4) Uani 1 1 d . . . C17 C 0.3408(3) 0.46954(14) 0.27629(14) 0.0547(6) Uani 1 1 d . . . H17A H 0.3788 0.5252 0.3053 0.082 Uiso 1 1 calc R . . H17B H 0.4291 0.4515 0.2398 0.082 Uiso 1 1 calc R . . H17C H 0.3319 0.4240 0.3199 0.082 Uiso 1 1 calc R . . 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 0.0539(9) 0.0380(8) 0.0577(9) 0.0123(6) 0.0139(7) -0.0037(6) O2 0.0639(9) 0.0257(7) 0.0468(8) -0.0020(5) 0.0186(7) -0.0090(6) O3 0.0602(9) 0.0243(6) 0.0495(8) -0.0024(5) 0.0154(7) -0.0050(6) O4 0.0623(9) 0.0326(7) 0.0535(9) -0.0098(6) 0.0051(7) 0.0052(6) O5 0.0462(8) 0.0323(7) 0.0429(8) -0.0018(5) 0.0102(7) -0.0032(6) N1 0.0322(8) 0.0341(8) 0.0381(9) 0.0020(6) 0.0017(7) 0.0040(6) N2 0.0392(9) 0.0277(8) 0.0434(10) 0.0055(6) 0.0053(7) -0.0021(6) N3 0.0497(10) 0.0259(8) 0.0536(11) 0.0019(7) 0.0084(8) -0.0070(7) N4 0.0377(8) 0.0305(8) 0.0395(9) 0.0001(6) 0.0038(7) -0.0002(6) N5 0.0505(10) 0.0251(8) 0.0566(11) -0.0043(7) 0.0079(8) -0.0038(7) N6 0.0413(9) 0.0256(7) 0.0424(9) -0.0045(6) 0.0030(7) -0.0002(6) C1 0.0311(9) 0.0376(10) 0.0388(11) -0.0029(8) -0.0010(8) 0.0068(8) C2 0.0402(11) 0.0463(11) 0.0441(12) -0.0085(9) 0.0006(9) 0.0061(9) C3 0.0421(11) 0.0603(13) 0.0389(12) 0.0015(9) 0.0049(9) 0.0057(9) C4 0.0367(10) 0.0478(12) 0.0444(12) 0.0098(9) 0.0047(9) 0.0043(9) C5 0.0295(9) 0.0367(10) 0.0408(11) 0.0078(8) 0.0019(8) 0.0052(8) C6 0.0319(9) 0.0348(10) 0.0432(11) 0.0088(8) 0.0013(8) 0.0012(8) C7 0.0433(11) 0.0274(9) 0.0529(13) 0.0036(8) 0.0062(10) -0.0050(8) C8 0.0553(12) 0.0355(10) 0.0457(12) -0.0069(8) 0.0110(10) -0.0069(9) C9 0.0378(10) 0.0329(9) 0.0355(10) -0.0023(7) 0.0003(8) 0.0012(8) C10 0.0478(11) 0.0380(10) 0.0408(11) -0.0041(8) 0.0041(9) 0.0042(9) C11 0.0540(13) 0.0490(12) 0.0421(12) 0.0006(9) 0.0148(10) 0.0033(10) C12 0.0479(11) 0.0406(11) 0.0439(12) 0.0073(8) 0.0117(10) -0.0011(9) C13 0.0345(10) 0.0327(9) 0.0383(11) 0.0056(8) 0.0017(8) 0.0014(8) C14 0.0489(12) 0.0324(10) 0.0499(12) 0.0038(8) 0.0148(10) -0.0025(8) C15 0.0456(11) 0.0268(9) 0.0512(13) -0.0044(8) 0.0042(10) -0.0019(8) C16 0.0336(10) 0.0336(10) 0.0434(11) -0.0042(8) -0.0028(8) 0.0077(8) C17 0.0494(13) 0.0611(14) 0.0531(14) 0.0080(10) 0.0065(11) 0.0026(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.227(2) . ? O2 C8 1.409(2) . ? O2 N3 1.4189(18) . ? O3 C14 1.417(2) . ? O3 N5 1.4221(18) . ? O4 C16 1.227(2) . ? O5 C17 1.411(2) . ? O5 H5H 0.90(3) . ? N1 C1 1.342(2) . ? N1 C5 1.344(2) . ? N2 C6 1.363(2) . ? N2 C7 1.380(2) . ? N2 H2B 0.8800 . ? N3 C7 1.270(2) . ? N4 C13 1.349(2) . ? N4 C9 1.350(2) . ? N5 C15 1.272(2) . ? N6 C16 1.365(2) . ? N6 C15 1.375(2) . ? N6 H6A 0.8800 . ? C1 C2 1.385(3) . ? C1 C16 1.498(3) . ? C2 C3 1.375(3) . ? C2 H2A 0.9500 . ? C3 C4 1.385(3) . ? C3 H3A 0.9500 . ? C4 C5 1.382(3) . ? C4 H4A 0.9500 . ? C5 C6 1.502(2) . ? C7 H7A 0.9500 . ? C8 C9 1.503(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.374(2) . ? C10 C11 1.380(3) . ? C10 H10A 0.9500 . ? C11 C12 1.379(3) . ? C11 H11A 0.9500 . ? C12 C13 1.375(2) . ? C12 H12A 0.9500 . ? C13 C14 1.507(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? 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 C8 O2 N3 108.15(12) . . ? C14 O3 N5 107.49(12) . . ? C17 O5 H5H 109.9(16) . . ? C1 N1 C5 116.93(16) . . ? C6 N2 C7 120.12(15) . . ? C6 N2 H2B 119.9 . . ? C7 N2 H2B 119.9 . . ? C7 N3 O2 110.15(14) . . ? C13 N4 C9 117.11(16) . . ? C15 N5 O3 109.86(14) . . ? C16 N6 C15 119.85(15) . . ? C16 N6 H6A 120.1 . . ? C15 N6 H6A 120.1 . . ? N1 C1 C2 123.05(17) . . ? N1 C1 C16 117.87(16) . . ? C2 C1 C16 118.97(16) . . ? C3 C2 C1 119.19(18) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 118.69(19) . . ? C2 C3 H3A 120.7 . . ? C4 C3 H3A 120.7 . . ? C5 C4 C3 118.57(18) . . ? C5 C4 H4A 120.7 . . ? C3 C4 H4A 120.7 . . ? N1 C5 C4 123.54(17) . . ? N1 C5 C6 117.41(16) . . ? C4 C5 C6 119.00(16) . . ? O1 C6 N2 122.83(17) . . ? O1 C6 C5 120.25(17) . . ? N2 C6 C5 116.88(15) . . ? N3 C7 N2 128.60(17) . . ? N3 C7 H7A 115.7 . . ? N2 C7 H7A 115.7 . . ? O2 C8 C9 111.20(14) . . ? O2 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? O2 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? N4 C9 C10 122.88(16) . . ? N4 C9 C8 118.99(16) . . ? C10 C9 C8 118.11(16) . . ? C9 C10 C11 119.15(18) . . ? C9 C10 H10A 120.4 . . ? C11 C10 H10A 120.4 . . ? C12 C11 C10 118.78(19) . . ? C12 C11 H11A 120.6 . . ? C10 C11 H11A 120.6 . . ? C13 C12 C11 119.06(17) . . ? C13 C12 H12A 120.5 . . ? C11 C12 H12A 120.5 . . ? N4 C13 C12 123.01(17) . . ? N4 C13 C14 119.28(16) . . ? C12 C13 C14 117.70(16) . . ? O3 C14 C13 110.74(14) . . ? O3 C14 H14A 109.5 . . ? C13 C14 H14A 109.5 . . ? O3 C14 H14B 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? N5 C15 N6 129.08(17) . . ? N5 C15 H15A 115.5 . . ? N6 C15 H15A 115.5 . . ? O4 C16 N6 122.33(17) . . ? O4 C16 C1 120.50(17) . . ? N6 C16 C1 117.14(15) . . ? O5 C17 H17A 109.5 . . ? O5 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O5 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? 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 C8 O2 N3 C7 166.09(16) . . . . ? C14 O3 N5 C15 -177.77(15) . . . . ? C5 N1 C1 C2 -1.1(2) . . . . ? C5 N1 C1 C16 -177.33(15) . . . . ? N1 C1 C2 C3 0.0(3) . . . . ? C16 C1 C2 C3 176.25(16) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C1 N1 C5 C4 1.4(3) . . . . ? C1 N1 C5 C6 178.68(15) . . . . ? C3 C4 C5 N1 -0.6(3) . . . . ? C3 C4 C5 C6 -177.90(16) . . . . ? C7 N2 C6 O1 7.3(3) . . . . ? C7 N2 C6 C5 -170.31(15) . . . . ? N1 C5 C6 O1 176.77(16) . . . . ? C4 C5 C6 O1 -5.8(3) . . . . ? N1 C5 C6 N2 -5.5(2) . . . . ? C4 C5 C6 N2 171.88(16) . . . . ? O2 N3 C7 N2 -0.7(3) . . . . ? C6 N2 C7 N3 175.14(18) . . . . ? N3 O2 C8 C9 168.52(14) . . . . ? C13 N4 C9 C10 1.2(3) . . . . ? C13 N4 C9 C8 179.40(16) . . . . ? O2 C8 C9 N4 22.2(2) . . . . ? O2 C8 C9 C10 -159.54(16) . . . . ? N4 C9 C10 C11 -0.3(3) . . . . ? C8 C9 C10 C11 -178.50(18) . . . . ? C9 C10 C11 C12 -0.9(3) . . . . ? C10 C11 C12 C13 1.1(3) . . . . ? C9 N4 C13 C12 -1.0(2) . . . . ? C9 N4 C13 C14 -179.49(16) . . . . ? C11 C12 C13 N4 -0.1(3) . . . . ? C11 C12 C13 C14 178.38(18) . . . . ? N5 O3 C14 C13 -174.88(14) . . . . ? N4 C13 C14 O3 -11.7(2) . . . . ? C12 C13 C14 O3 169.74(15) . . . . ? O3 N5 C15 N6 0.1(3) . . . . ? C16 N6 C15 N5 -173.08(18) . . . . ? C15 N6 C16 O4 -3.2(3) . . . . ? C15 N6 C16 C1 174.56(15) . . . . ? N1 C1 C16 O4 179.44(16) . . . . ? C2 C1 C16 O4 3.0(3) . . . . ? N1 C1 C16 N6 1.6(2) . . . . ? C2 C1 C16 N6 -174.80(15) . . . . ? 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 O5 H5H N4 0.90(3) 1.93(3) 2.827(2) 174(2) . O5 H5H O2 0.90(3) 2.44(2) 2.7935(17) 103.7(18) . O5 H5H O3 0.90(3) 2.39(2) 2.7864(17) 106.8(18) . N2 H2B O5 0.88 2.00 2.8523(19) 164.0 . N6 H6A O5 0.88 1.97 2.8273(18) 164.2 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.157 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.038 data_ap33b _database_code_depnum_ccdc_archive 'CCDC 874204' #TrackingRef 'web_deposit_cif_file_1_AnnePetitjean_1333204486.ap33b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17.50 H15 N6 O7.25' _chemical_formula_weight 425.36 _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 C2/m _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 17.5387(3) _cell_length_b 13.3386(2) _cell_length_c 7.87380(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.1200(10) _cell_angle_gamma 90.00 _cell_volume 1818.72(5) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 2597 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 26.93 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9697 _exptl_absorpt_correction_T_max 0.9816 _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4940 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1864 _reflns_number_gt 1608 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 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^)+(0.1054P)^2^+0.7778P] 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 0.0035(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1864 _refine_ls_number_parameters 197 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1617 _refine_ls_wR_factor_gt 0.1498 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _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 0.18729(8) 0.26343(9) -0.37725(17) 0.0484(4) Uani 1 1 d . A . O3 O 0.48602(8) 0.26298(10) 0.23200(19) 0.0546(4) Uani 1 1 d . A . O5 O 0.0000 0.0000 0.0000 0.124(4) Uani 0.50 4 d SP . . N1 N 0.21211(10) 0.0000 -0.3304(2) 0.0305(4) Uani 1 2 d SD . . N4 N 0.46355(10) 0.0000 0.1830(2) 0.0314(5) Uani 1 2 d SD . . C1 C 0.0807(2) 0.0000 -0.5787(5) 0.0815(12) Uani 1 2 d S . . H1A H 0.0351 0.0000 -0.6619 0.098 Uiso 1 2 calc SR . . C2 C 0.11391(13) 0.08935(16) -0.5180(3) 0.0619(6) Uani 1 1 d . . . H2A H 0.0926 0.1517 -0.5600 0.074 Uiso 1 1 calc R . . C3 C 0.17968(10) 0.08552(13) -0.3931(2) 0.0372(4) Uani 1 1 d . A . C4 C 0.21437(9) 0.18325(12) -0.3277(2) 0.0352(4) Uani 1 1 d . . . O2 O 0.2804(6) 0.1771(8) -0.2099(17) 0.0284(14) Uani 0.661(12) 1 d P A 1 N2 N 0.3093(11) 0.2674(11) -0.1480(18) 0.048(3) Uani 0.661(12) 1 d P A 1 C5 C 0.3672(9) 0.2541(10) -0.033(2) 0.0417(19) Uani 0.661(12) 1 d P A 1 H5A H 0.3942 0.3140 0.0033 0.050 Uiso 0.661(12) 1 calc PR A 1 N3 N 0.3971(13) 0.1733(11) 0.0463(17) 0.031(2) Uani 0.661(12) 1 d P A 1 H3A H 0.3774 0.1139 0.0173 0.037 Uiso 0.661(12) 1 calc PR A 1 O2A O 0.405(2) 0.1718(18) 0.049(3) 0.038(5) Uani 0.339(12) 1 d P A 2 N2A N 0.3725(15) 0.2737(16) -0.014(3) 0.037(3) Uani 0.339(12) 1 d P A 2 C5A C 0.318(2) 0.262(2) -0.152(5) 0.049(6) Uani 0.339(12) 1 d P A 2 H5AA H 0.3041 0.3186 -0.2236 0.059 Uiso 0.339(12) 1 calc PR A 2 N3A N 0.2743(18) 0.158(2) -0.201(5) 0.037(4) Uani 0.339(12) 1 d P A 2 H3AA H 0.2861 0.0984 -0.1572 0.044 Uiso 0.339(12) 1 calc PR A 2 C6 C 0.46099(9) 0.18260(13) 0.1778(2) 0.0370(4) Uani 1 1 d . . . C7 C 0.49695(9) 0.08552(13) 0.24338(19) 0.0339(4) Uani 1 1 d . A . C8 C 0.56497(10) 0.08941(15) 0.3630(2) 0.0433(5) Uani 1 1 d . . . H8A H 0.5871 0.1518 0.4028 0.052 Uiso 1 1 calc R A . C9 C 0.59908(13) 0.0000 0.4215(3) 0.0469(7) Uani 1 2 d S . . H9A H 0.6457 0.0000 0.5015 0.056 Uiso 1 2 calc SR . . C10 C 0.26084(16) 0.0000 0.1290(3) 0.0467(6) Uani 1 2 d S . . C11 C 0.0575(5) 0.0000 -0.0717(14) 0.104(3) Uani 0.50 2 d SP . . O4 O 0.30836(9) 0.0000 -0.0021(2) 0.0379(4) Uani 1 2 d SD . . H4H H 0.284(3) 0.0000 -0.112(6) 0.045 Uiso 0.661(12) 2 d SPD . . H4HA H 0.361(3) 0.0000 0.034(8) 0.045 Uiso 0.339(12) 2 d SPD . . _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 0.0496(8) 0.0390(7) 0.0532(8) 0.0110(5) -0.0024(6) 0.0142(5) O3 0.0494(8) 0.0482(8) 0.0616(9) -0.0181(6) -0.0055(6) -0.0149(6) O5 0.203(14) 0.115(8) 0.051(4) 0.000 0.015(6) 0.000 N1 0.0283(9) 0.0338(10) 0.0276(9) 0.000 -0.0014(7) 0.000 N4 0.0261(9) 0.0437(11) 0.0233(8) 0.000 0.0004(7) 0.000 C1 0.072(2) 0.074(2) 0.078(2) 0.000 -0.0523(19) 0.000 C2 0.0572(12) 0.0553(12) 0.0613(13) 0.0077(9) -0.0275(10) 0.0077(9) C3 0.0343(8) 0.0431(9) 0.0313(8) 0.0046(6) -0.0036(6) 0.0057(7) C4 0.0340(8) 0.0364(8) 0.0344(8) 0.0071(6) 0.0033(6) 0.0079(7) O2 0.030(2) 0.013(3) 0.0402(15) 0.006(2) -0.0017(15) 0.000(2) N2 0.041(4) 0.038(5) 0.064(4) -0.005(3) 0.004(3) 0.000(2) C5 0.043(3) 0.019(5) 0.062(3) -0.011(3) 0.005(3) -0.005(3) N3 0.030(3) 0.030(4) 0.031(4) -0.008(3) 0.000(2) -0.005(2) O2A 0.036(8) 0.030(6) 0.047(8) 0.000(5) 0.000(4) -0.004(4) N2A 0.045(5) 0.009(7) 0.054(6) -0.005(4) -0.002(4) -0.005(4) C5A 0.041(9) 0.017(6) 0.087(13) -0.015(6) 0.003(7) -0.001(5) N3A 0.042(5) 0.016(8) 0.051(6) 0.003(5) 0.000(3) -0.009(5) C6 0.0321(9) 0.0454(9) 0.0333(8) -0.0088(7) 0.0046(7) -0.0106(7) C7 0.0277(8) 0.0498(10) 0.0239(7) -0.0047(6) 0.0030(6) -0.0067(6) C8 0.0296(8) 0.0698(12) 0.0294(8) -0.0067(7) 0.0015(6) -0.0114(8) C9 0.0242(11) 0.087(2) 0.0272(11) 0.000 -0.0045(9) 0.000 C10 0.0499(14) 0.0364(12) 0.0527(15) 0.000 0.0053(12) 0.000 C11 0.071(5) 0.113(7) 0.108(8) 0.000 -0.049(5) 0.000 O4 0.0357(9) 0.0339(8) 0.0386(9) 0.000 -0.0105(7) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; _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 C4 1.2096(19) . ? O3 C6 1.210(2) . ? O5 C11 1.232(13) . ? O5 C11 1.232(13) 5 ? N1 C3 1.3339(19) 6 ? N1 C3 1.3339(19) . ? N4 C7 1.3348(18) . ? N4 C7 1.3348(18) 6 ? C1 C2 1.379(3) . ? C1 C2 1.379(3) 6 ? C1 H1A 0.9500 . ? C2 C3 1.393(2) . ? C2 H2A 0.9500 . ? C3 C4 1.495(2) . ? C4 O2 1.366(12) . ? C4 N3A 1.37(3) . ? O2 N2 1.367(19) . ? N2 C5 1.26(2) . ? C5 N3 1.31(3) . ? C5 H5A 0.9500 . ? N3 C6 1.405(19) . ? N3 H3A 0.8800 . ? O2A C6 1.31(3) . ? O2A N2A 1.52(4) . ? N2A C5A 1.33(4) . ? C5A N3A 1.60(5) . ? C5A H5AA 0.9500 . ? N3A H3AA 0.8800 . ? C6 C7 1.496(2) . ? C7 C8 1.399(2) . ? C8 C9 1.380(2) . ? C8 H8A 0.9500 . ? C9 C8 1.380(2) 6 ? C9 H9A 0.9500 . ? C10 O4 1.426(3) . ? O4 H4H 0.90(4) . ? O4 H4HA 0.91(5) . ? _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 C11 O5 C11 180.0(11) . 5 ? C3 N1 C3 117.55(19) 6 . ? C7 N4 C7 117.42(18) . 6 ? C2 C1 C2 119.6(2) . 6 ? C2 C1 H1A 120.2 . . ? C2 C1 H1A 120.2 6 . ? C1 C2 C3 118.07(18) . . ? C1 C2 H2A 121.0 . . ? C3 C2 H2A 121.0 . . ? N1 C3 C2 123.33(16) . . ? N1 C3 C4 119.45(14) . . ? C2 C3 C4 117.22(15) . . ? O1 C4 O2 121.3(5) . . ? O1 C4 N3A 131.9(12) . . ? O2 C4 N3A 12.1(14) . . ? O1 C4 C3 122.83(15) . . ? O2 C4 C3 115.8(4) . . ? N3A C4 C3 105.1(12) . . ? C4 O2 N2 114.5(8) . . ? C5 N2 O2 110.0(12) . . ? N2 C5 N3 132.3(14) . . ? N2 C5 H5A 113.8 . . ? N3 C5 H5A 113.8 . . ? C5 N3 C6 119.4(12) . . ? C5 N3 H3A 120.3 . . ? C6 N3 H3A 120.3 . . ? C6 O2A N2A 110.6(17) . . ? C5A N2A O2A 110(2) . . ? N2A C5A N3A 123(3) . . ? N2A C5A H5AA 118.3 . . ? N3A C5A H5AA 118.3 . . ? C4 N3A C5A 104.3(19) . . ? C4 N3A H3AA 127.9 . . ? C5A N3A H3AA 127.9 . . ? O3 C6 O2A 123.9(11) . . ? O3 C6 N3 122.7(6) . . ? O2A C6 N3 4(2) . . ? O3 C6 C7 122.38(15) . . ? O2A C6 C7 113.5(11) . . ? N3 C6 C7 114.9(6) . . ? N4 C7 C8 123.41(16) . . ? N4 C7 C6 118.66(14) . . ? C8 C7 C6 117.91(15) . . ? C9 C8 C7 118.10(17) . . ? C9 C8 H8A 121.0 . . ? C7 C8 H8A 121.0 . . ? C8 C9 C8 119.5(2) 6 . ? C8 C9 H9A 120.2 6 . ? C8 C9 H9A 120.2 . . ? C10 O4 H4H 117(3) . . ? C10 O4 H4HA 117(4) . . ? H4H O4 H4HA 126(6) . . ? _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 C1 C2 C3 -1.4(6) 6 . . . ? C3 N1 C3 C2 0.7(3) 6 . . . ? C3 N1 C3 C4 -179.54(11) 6 . . . ? C1 C2 C3 N1 0.3(4) . . . . ? C1 C2 C3 C4 -179.4(3) . . . . ? N1 C3 C4 O1 -178.96(16) . . . . ? C2 C3 C4 O1 0.8(3) . . . . ? N1 C3 C4 O2 2.5(6) . . . . ? C2 C3 C4 O2 -177.7(6) . . . . ? N1 C3 C4 N3A -3.3(14) . . . . ? C2 C3 C4 N3A 176.5(14) . . . . ? O1 C4 O2 N2 3.6(14) . . . . ? N3A C4 O2 N2 -150(10) . . . . ? C3 C4 O2 N2 -177.9(9) . . . . ? C4 O2 N2 C5 176.0(12) . . . . ? O2 N2 C5 N3 -9(3) . . . . ? N2 C5 N3 C6 -176.8(17) . . . . ? C6 O2A N2A C5A 177(3) . . . . ? O2A N2A C5A N3A 18(5) . . . . ? O1 C4 N3A C5A -13(3) . . . . ? O2 C4 N3A C5A 18(8) . . . . ? C3 C4 N3A C5A 172(2) . . . . ? N2A C5A N3A C4 169(3) . . . . ? N2A O2A C6 O3 -3(3) . . . . ? N2A O2A C6 N3 68(26) . . . . ? N2A O2A C6 C7 -178.3(15) . . . . ? C5 N3 C6 O3 6.4(18) . . . . ? C5 N3 C6 O2A -104(26) . . . . ? C5 N3 C6 C7 -172.3(12) . . . . ? C7 N4 C7 C8 1.1(3) 6 . . . ? C7 N4 C7 C6 179.83(11) 6 . . . ? O3 C6 C7 N4 176.69(16) . . . . ? O2A C6 C7 N4 -8.4(14) . . . . ? N3 C6 C7 N4 -4.6(8) . . . . ? O3 C6 C7 C8 -4.5(2) . . . . ? O2A C6 C7 C8 170.4(14) . . . . ? N3 C6 C7 C8 174.2(8) . . . . ? N4 C7 C8 C9 -0.1(3) . . . . ? C6 C7 C8 C9 -178.88(15) . . . . ? C7 C8 C9 C8 -0.9(3) . . . 6 ? _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4H O2 0.90(4) 2.481(17) 2.871(10) 106.5(11) . O4 H4H N1 0.90(4) 1.97(4) 2.855(2) 168(4) . N3 H3A O4 0.88 1.93 2.780(16) 160.6 . O4 H4HA O2A 0.91(5) 2.42(3) 2.84(3) 108.2(14) . N3A H3AA O4 0.88 1.79 2.64(3) 160.5 . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.568 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.063 data_ap32 _database_code_depnum_ccdc_archive 'CCDC 876656' #TrackingRef 'web_deposit_cif_file_0_AnnePetitjean_1334672714.ap32.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H11 N5 O5' _chemical_formula_weight 269.23 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 9.48230(10) _cell_length_b 7.17710(10) _cell_length_c 35.7292(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.9590(10) _cell_angle_gamma 90.00 _cell_volume 2431.22(6) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3602 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 26.53 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9643 _exptl_absorpt_correction_T_max 0.9927 _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17514 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4754 _reflns_number_gt 3426 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 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^)+(0.0435P)^2^+0.4373P] 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 4754 _refine_ls_number_parameters 375 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0856 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 0.55843(13) 0.79792(19) 0.23529(4) 0.0360(3) Uani 1 1 d . . . O2 O 0.94797(15) 0.7594(2) 0.15533(4) 0.0374(4) Uani 1 1 d . . . H2H H 1.038(3) 0.731(3) 0.1500(7) 0.064(8) Uiso 1 1 d . . . O3 O 0.38601(13) 1.18360(19) 0.05970(4) 0.0359(3) Uani 1 1 d . . . O4 O 0.86345(14) 1.0092(2) 0.06675(4) 0.0357(3) Uani 1 1 d . . . H4H H 0.954(3) 1.004(3) 0.0593(8) 0.079(9) Uiso 1 1 d . . . O5 O 0.40833(14) 0.7086(2) 0.03404(4) 0.0435(4) Uani 1 1 d . . . O6 O 0.32203(14) 0.56530(19) 0.15983(4) 0.0343(3) Uani 1 1 d . . . H6H H 0.271(3) 0.553(3) 0.1833(7) 0.068(8) Uiso 1 1 d . . . O7 O 0.99631(13) 0.31482(19) 0.12638(4) 0.0358(3) Uani 1 1 d . . . O8 O 0.60301(14) 0.3555(2) 0.20406(4) 0.0359(3) Uani 1 1 d . . . H8H H 0.551(3) 0.340(4) 0.2255(8) 0.073(8) Uiso 1 1 d . . . N1 N 0.51770(14) 0.98706(19) 0.14421(4) 0.0233(3) Uani 1 1 d . . . N2 N 0.70809(15) 0.8070(2) 0.18665(4) 0.0266(4) Uani 1 1 d . . . H2B H 0.7172 0.8316 0.1627 0.032 Uiso 1 1 calc R . . N3 N 0.94245(16) 0.7040(2) 0.19298(4) 0.0327(4) Uani 1 1 d . . . N4 N 0.60261(14) 1.0704(2) 0.07525(4) 0.0258(3) Uani 1 1 d . . . H4B H 0.6552 1.0216 0.0932 0.031 Uiso 1 1 calc R . . N5 N 0.79189(16) 1.0678(2) 0.03419(4) 0.0309(4) Uani 1 1 d . . . N6 N 0.67985(15) 0.51123(19) 0.09036(4) 0.0241(3) Uani 1 1 d . . . N7 N 0.41094(15) 0.6154(2) 0.09459(4) 0.0264(4) Uani 1 1 d . . . H7B H 0.4620 0.5613 0.1123 0.032 Uiso 1 1 calc R . . N8 N 0.22296(15) 0.6476(2) 0.13535(4) 0.0300(4) Uani 1 1 d . . . N9 N 0.77998(15) 0.3468(2) 0.15196(4) 0.0265(4) Uani 1 1 d . . . H9B H 0.6935 0.3877 0.1481 0.032 Uiso 1 1 calc R . . N10 N 0.72842(16) 0.2604(2) 0.21325(5) 0.0339(4) Uani 1 1 d . . . C1 C 0.47934(18) 0.9491(2) 0.17921(5) 0.0237(4) Uani 1 1 d . . . C2 C 0.35075(19) 1.0040(3) 0.19386(6) 0.0305(4) Uani 1 1 d . . . H2A H 0.3270 0.9739 0.2189 0.037 Uiso 1 1 calc R . . C3 C 0.25907(19) 1.1028(3) 0.17125(6) 0.0335(5) Uani 1 1 d . . . H3A H 0.1711 1.1439 0.1806 0.040 Uiso 1 1 calc R . . C4 C 0.29586(18) 1.1420(3) 0.13481(6) 0.0304(4) Uani 1 1 d . . . H4A H 0.2337 1.2093 0.1186 0.036 Uiso 1 1 calc R . . C5 C 0.42555(18) 1.0809(2) 0.12243(5) 0.0248(4) Uani 1 1 d . . . C6 C 0.58302(18) 0.8449(2) 0.20324(5) 0.0259(4) Uani 1 1 d . . . C7 C 0.82060(19) 0.7315(3) 0.20619(5) 0.0291(4) Uani 1 1 d . . . H7A H 0.8060 0.6973 0.2315 0.035 Uiso 1 1 calc R . . C8 C 0.46769(18) 1.1167(2) 0.08304(5) 0.0259(4) Uani 1 1 d . . . C9 C 0.66205(19) 1.0957(3) 0.04060(5) 0.0279(4) Uani 1 1 d . . . H9A H 0.6028 1.1361 0.0205 0.034 Uiso 1 1 calc R . . C10 C 0.62385(18) 0.5884(2) 0.05936(5) 0.0248(4) Uani 1 1 d . . . C11 C 0.7000(2) 0.6224(3) 0.02742(5) 0.0316(4) Uani 1 1 d . . . H11A H 0.6560 0.6748 0.0058 0.038 Uiso 1 1 calc R . . C12 C 0.8419(2) 0.5781(3) 0.02778(6) 0.0365(5) Uani 1 1 d . . . H12A H 0.8979 0.6040 0.0066 0.044 Uiso 1 1 calc R . . C13 C 0.9016(2) 0.4957(3) 0.05928(5) 0.0323(5) Uani 1 1 d . . . H13A H 0.9985 0.4623 0.0600 0.039 Uiso 1 1 calc R . . C14 C 0.81654(18) 0.4632(2) 0.08969(5) 0.0252(4) Uani 1 1 d . . . C15 C 0.47123(19) 0.6427(2) 0.06073(5) 0.0272(4) Uani 1 1 d . . . C16 C 0.27506(18) 0.6671(3) 0.10300(5) 0.0282(4) Uani 1 1 d . . . H16A H 0.2176 0.7198 0.0837 0.034 Uiso 1 1 calc R . . C17 C 0.87528(18) 0.3688(2) 0.12385(5) 0.0258(4) Uani 1 1 d . . . C18 C 0.8111(2) 0.2652(3) 0.18564(5) 0.0312(4) Uani 1 1 d . . . H18A H 0.9010 0.2080 0.1886 0.037 Uiso 1 1 calc R . . O1W O 1.12376(16) 1.0016(3) 0.04138(5) 0.0547(5) Uani 1 1 d . . . H1WA H 1.147(3) 0.966(4) 0.0180(9) 0.091(10) Uiso 1 1 d . . . H1WB H 1.198(3) 1.058(4) 0.0499(8) 0.079(10) Uiso 1 1 d . . . O2W O 0.18410(16) 0.5302(2) 0.22305(4) 0.0371(4) Uani 1 1 d . . . H2WA H 0.220(3) 0.601(4) 0.2421(9) 0.090(10) Uiso 1 1 d . . . H2WB H 0.099(3) 0.588(4) 0.2162(8) 0.078(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 O1 0.0340(7) 0.0497(9) 0.0246(8) 0.0046(6) 0.0082(6) 0.0078(6) O2 0.0280(8) 0.0533(9) 0.0312(8) 0.0072(7) 0.0070(6) 0.0080(7) O3 0.0284(7) 0.0454(9) 0.0338(8) 0.0072(7) -0.0032(6) 0.0075(6) O4 0.0258(7) 0.0539(9) 0.0272(8) 0.0050(7) -0.0010(6) 0.0062(7) O5 0.0366(8) 0.0626(10) 0.0312(8) 0.0134(7) -0.0016(6) 0.0130(7) O6 0.0306(7) 0.0421(8) 0.0304(8) 0.0040(7) 0.0026(6) 0.0056(6) O7 0.0225(7) 0.0469(9) 0.0379(8) 0.0047(7) 0.0022(6) 0.0090(6) O8 0.0309(7) 0.0466(9) 0.0304(8) 0.0034(7) 0.0079(6) 0.0032(6) N1 0.0217(7) 0.0223(8) 0.0260(9) -0.0020(7) 0.0004(6) -0.0008(6) N2 0.0246(8) 0.0327(9) 0.0227(8) 0.0016(7) 0.0046(6) 0.0063(7) N3 0.0282(9) 0.0426(10) 0.0272(9) 0.0001(8) 0.0016(7) 0.0054(7) N4 0.0221(8) 0.0325(9) 0.0227(8) 0.0035(7) 0.0001(6) 0.0044(6) N5 0.0281(8) 0.0397(9) 0.0249(9) 0.0032(7) -0.0002(7) 0.0029(7) N6 0.0246(8) 0.0248(8) 0.0229(8) -0.0009(6) 0.0013(6) 0.0016(6) N7 0.0215(8) 0.0322(9) 0.0256(9) 0.0026(7) -0.0003(6) 0.0041(7) N8 0.0246(8) 0.0310(9) 0.0343(10) 0.0008(7) 0.0010(7) 0.0012(7) N9 0.0204(7) 0.0362(9) 0.0230(8) 0.0045(7) 0.0009(6) 0.0023(7) N10 0.0307(9) 0.0412(10) 0.0297(10) 0.0057(8) 0.0001(7) -0.0025(7) C1 0.0232(9) 0.0231(9) 0.0248(10) -0.0034(8) 0.0034(7) -0.0012(7) C2 0.0275(10) 0.0338(11) 0.0304(11) -0.0023(9) 0.0074(8) 0.0022(8) C3 0.0225(9) 0.0387(11) 0.0396(12) -0.0049(9) 0.0077(9) 0.0084(8) C4 0.0238(9) 0.0306(10) 0.0368(12) 0.0017(9) 0.0004(8) 0.0059(8) C5 0.0214(9) 0.0213(9) 0.0316(11) -0.0015(8) 0.0001(8) -0.0008(7) C6 0.0255(9) 0.0252(10) 0.0271(11) -0.0029(8) 0.0041(8) -0.0004(8) C7 0.0268(10) 0.0350(11) 0.0257(10) 0.0006(8) 0.0005(8) 0.0042(8) C8 0.0222(9) 0.0251(10) 0.0304(10) -0.0007(8) -0.0015(8) 0.0007(7) C9 0.0291(10) 0.0327(10) 0.0219(10) 0.0028(8) -0.0006(8) 0.0016(8) C10 0.0277(9) 0.0240(9) 0.0226(10) -0.0019(8) 0.0010(8) 0.0026(7) C11 0.0393(11) 0.0319(11) 0.0237(10) 0.0040(8) 0.0040(8) 0.0060(9) C12 0.0395(12) 0.0422(12) 0.0284(11) 0.0071(9) 0.0146(9) 0.0079(9) C13 0.0267(10) 0.0412(12) 0.0293(11) -0.0001(9) 0.0070(8) 0.0061(9) C14 0.0229(9) 0.0264(9) 0.0263(10) -0.0023(8) 0.0035(7) 0.0020(7) C15 0.0297(10) 0.0260(10) 0.0260(10) -0.0004(8) -0.0012(8) 0.0014(8) C16 0.0219(9) 0.0307(10) 0.0320(11) 0.0011(9) -0.0004(8) 0.0024(8) C17 0.0231(9) 0.0284(10) 0.0260(10) -0.0028(8) 0.0007(8) 0.0005(8) C18 0.0261(10) 0.0377(11) 0.0298(11) 0.0064(9) -0.0012(8) 0.0015(8) O1W 0.0252(8) 0.1029(15) 0.0362(10) -0.0104(10) 0.0043(7) 0.0001(9) O2W 0.0362(8) 0.0473(9) 0.0276(8) 0.0024(7) -0.0010(6) 0.0097(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 O1 C6 1.220(2) . ? O2 N3 1.404(2) . ? O2 H2H 0.90(2) . ? O3 C8 1.227(2) . ? O4 N5 1.4014(19) . ? O4 H4H 0.91(3) . ? O5 C15 1.213(2) . ? O6 N8 1.4032(19) . ? O6 H6H 0.98(3) . ? O7 C17 1.213(2) . ? O8 N10 1.405(2) . ? O8 H8H 0.93(3) . ? N1 C1 1.336(2) . ? N1 C5 1.342(2) . ? N2 C6 1.362(2) . ? N2 C7 1.376(2) . ? N2 H2B 0.8800 . ? N3 C7 1.271(2) . ? N4 C8 1.355(2) . ? N4 C9 1.381(2) . ? N4 H4B 0.8800 . ? N5 C9 1.272(2) . ? N6 C10 1.340(2) . ? N6 C14 1.342(2) . ? N7 C15 1.361(2) . ? N7 C16 1.379(2) . ? N7 H7B 0.8800 . ? N8 C16 1.272(2) . ? N9 C18 1.366(2) . ? N9 C17 1.371(2) . ? N9 H9B 0.8800 . ? N10 C18 1.271(2) . ? C1 C2 1.392(2) . ? C1 C6 1.495(2) . ? C2 C3 1.374(3) . ? C2 H2A 0.9500 . ? C3 C4 1.382(3) . ? C3 H3A 0.9500 . ? C4 C5 1.385(2) . ? C4 H4A 0.9500 . ? C5 C8 1.492(3) . ? C7 H7A 0.9500 . ? C9 H9A 0.9500 . ? C10 C11 1.382(3) . ? C10 C15 1.500(2) . ? C11 C12 1.382(3) . ? C11 H11A 0.9500 . ? C12 C13 1.384(3) . ? C12 H12A 0.9500 . ? C13 C14 1.384(3) . ? C13 H13A 0.9500 . ? C14 C17 1.495(2) . ? C16 H16A 0.9500 . ? C18 H18A 0.9500 . ? O1W H1WA 0.90(3) . ? O1W H1WB 0.86(3) . ? O2W H2WA 0.91(3) . ? O2W H2WB 0.93(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 N3 O2 H2H 100.9(16) . . ? N5 O4 H4H 102.6(17) . . ? N8 O6 H6H 103.6(14) . . ? N10 O8 H8H 102.2(16) . . ? C1 N1 C5 117.41(15) . . ? C6 N2 C7 122.08(16) . . ? C6 N2 H2B 119.0 . . ? C7 N2 H2B 119.0 . . ? C7 N3 O2 111.14(15) . . ? C8 N4 C9 123.57(15) . . ? C8 N4 H4B 118.2 . . ? C9 N4 H4B 118.2 . . ? C9 N5 O4 110.75(15) . . ? C10 N6 C14 117.46(15) . . ? C15 N7 C16 124.28(16) . . ? C15 N7 H7B 117.9 . . ? C16 N7 H7B 117.9 . . ? C16 N8 O6 110.27(15) . . ? C18 N9 C17 123.99(15) . . ? C18 N9 H9B 118.0 . . ? C17 N9 H9B 118.0 . . ? C18 N10 O8 109.64(15) . . ? N1 C1 C2 123.25(17) . . ? N1 C1 C6 116.92(15) . . ? C2 C1 C6 119.82(17) . . ? C3 C2 C1 118.32(18) . . ? C3 C2 H2A 120.8 . . ? C1 C2 H2A 120.8 . . ? C2 C3 C4 119.46(17) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C3 C4 C5 118.40(17) . . ? C3 C4 H4A 120.8 . . ? C5 C4 H4A 120.8 . . ? N1 C5 C4 123.15(18) . . ? N1 C5 C8 116.85(15) . . ? C4 C5 C8 120.00(16) . . ? O1 C6 N2 122.32(17) . . ? O1 C6 C1 122.91(16) . . ? N2 C6 C1 114.77(16) . . ? N3 C7 N2 125.07(18) . . ? N3 C7 H7A 117.5 . . ? N2 C7 H7A 117.5 . . ? O3 C8 N4 122.94(18) . . ? O3 C8 C5 122.20(16) . . ? N4 C8 C5 114.86(15) . . ? N5 C9 N4 123.48(17) . . ? N5 C9 H9A 118.3 . . ? N4 C9 H9A 118.3 . . ? N6 C10 C11 123.37(17) . . ? N6 C10 C15 116.71(16) . . ? C11 C10 C15 119.91(16) . . ? C10 C11 C12 118.27(17) . . ? C10 C11 H11A 120.9 . . ? C12 C11 H11A 120.9 . . ? C11 C12 C13 119.38(18) . . ? C11 C12 H12A 120.3 . . ? C13 C12 H12A 120.3 . . ? C14 C13 C12 118.36(17) . . ? C14 C13 H13A 120.8 . . ? C12 C13 H13A 120.8 . . ? N6 C14 C13 123.11(17) . . ? N6 C14 C17 116.65(15) . . ? C13 C14 C17 120.23(16) . . ? O5 C15 N7 123.14(17) . . ? O5 C15 C10 122.53(17) . . ? N7 C15 C10 114.31(15) . . ? N8 C16 N7 123.16(17) . . ? N8 C16 H16A 118.4 . . ? N7 C16 H16A 118.4 . . ? O7 C17 N9 122.88(17) . . ? O7 C17 C14 122.97(16) . . ? N9 C17 C14 114.15(15) . . ? N10 C18 N9 124.61(17) . . ? N10 C18 H18A 117.7 . . ? N9 C18 H18A 117.7 . . ? H1WA O1W H1WB 105(2) . . ? H2WA O2W H2WB 105(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 -0.8(3) . . . . ? C5 N1 C1 C6 -179.85(15) . . . . ? N1 C1 C2 C3 -0.3(3) . . . . ? C6 C1 C2 C3 178.70(17) . . . . ? C1 C2 C3 C4 1.0(3) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C1 N1 C5 C4 1.3(3) . . . . ? C1 N1 C5 C8 -177.98(15) . . . . ? C3 C4 C5 N1 -0.7(3) . . . . ? C3 C4 C5 C8 178.61(17) . . . . ? C7 N2 C6 O1 -7.3(3) . . . . ? C7 N2 C6 C1 172.36(16) . . . . ? N1 C1 C6 O1 -177.93(16) . . . . ? C2 C1 C6 O1 3.0(3) . . . . ? N1 C1 C6 N2 2.4(2) . . . . ? C2 C1 C6 N2 -176.68(16) . . . . ? O2 N3 C7 N2 -0.6(3) . . . . ? C6 N2 C7 N3 -175.27(18) . . . . ? C9 N4 C8 O3 0.8(3) . . . . ? C9 N4 C8 C5 -178.92(16) . . . . ? N1 C5 C8 O3 172.23(16) . . . . ? C4 C5 C8 O3 -7.1(3) . . . . ? N1 C5 C8 N4 -8.1(2) . . . . ? C4 C5 C8 N4 172.63(16) . . . . ? O4 N5 C9 N4 0.0(3) . . . . ? C8 N4 C9 N5 173.52(17) . . . . ? C14 N6 C10 C11 -0.9(3) . . . . ? C14 N6 C10 C15 -179.52(15) . . . . ? N6 C10 C11 C12 -1.5(3) . . . . ? C15 C10 C11 C12 177.16(17) . . . . ? C10 C11 C12 C13 2.3(3) . . . . ? C11 C12 C13 C14 -1.0(3) . . . . ? C10 N6 C14 C13 2.4(3) . . . . ? C10 N6 C14 C17 -177.12(15) . . . . ? C12 C13 C14 N6 -1.4(3) . . . . ? C12 C13 C14 C17 178.01(17) . . . . ? C16 N7 C15 O5 -3.2(3) . . . . ? C16 N7 C15 C10 175.36(16) . . . . ? N6 C10 C15 O5 -177.82(17) . . . . ? C11 C10 C15 O5 3.5(3) . . . . ? N6 C10 C15 N7 3.6(2) . . . . ? C11 C10 C15 N7 -175.11(16) . . . . ? O6 N8 C16 N7 -1.0(2) . . . . ? C15 N7 C16 N8 -176.82(18) . . . . ? C18 N9 C17 O7 1.0(3) . . . . ? C18 N9 C17 C14 -179.67(16) . . . . ? N6 C14 C17 O7 178.28(17) . . . . ? C13 C14 C17 O7 -1.2(3) . . . . ? N6 C14 C17 N9 -1.0(2) . . . . ? C13 C14 C17 N9 179.47(16) . . . . ? O8 N10 C18 N9 -1.6(3) . . . . ? C17 N9 C18 N10 172.64(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2H N8 0.90(2) 1.93(3) 2.831(2) 174(2) 1_655 O4 H4H O1W 0.91(3) 1.74(3) 2.644(2) 175(3) . O6 H6H O2W 0.98(3) 1.66(3) 2.641(2) 179(2) . O8 H8H O1 0.93(3) 1.78(3) 2.7060(19) 176(2) 2_645 O1W H1WA N5 0.90(3) 1.98(3) 2.873(2) 170(3) 3_775 O1W H1WB O3 0.86(3) 2.03(3) 2.875(2) 169(3) 1_655 O2W H2WA N10 0.91(3) 2.01(3) 2.921(2) 172(3) 2_655 O2W H2WB N3 0.93(3) 1.88(3) 2.807(2) 169(3) 1_455 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.196 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.048