# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 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_11091705 #TrackingRef 'web_deposit_cif_file_0_YanYan_1355189863.ACVMA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 N5 O7' _chemical_formula_weight 340.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7526(8) _cell_length_b 12.8631(11) _cell_length_c 14.0334(14) _cell_angle_alpha 67.419(9) _cell_angle_beta 86.643(8) _cell_angle_gamma 74.314(8) _cell_volume 1402.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3018 _cell_measurement_theta_min 3.4125 _cell_measurement_theta_max 66.9010 _exptl_crystal_description bluk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 1.164 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9441 _exptl_absorpt_correction_T_max 0.9771 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9501 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 67.01 _reflns_number_total 4810 _reflns_number_gt 3724 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0726P)^2^+0.0000P] 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 4810 _refine_ls_number_parameters 474 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1367 _refine_ls_wR_factor_gt 0.1236 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.004 _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 O9 O 0.4751(2) 0.05954(15) 0.60336(14) 0.0277(4) Uani 1 1 d D . . O7 O 0.0396(2) 0.30236(15) 0.43828(13) 0.0265(4) Uani 1 1 d . . . O8 O 0.2830(2) 0.24382(15) 0.50797(14) 0.0286(4) Uani 1 1 d . . . O10 O 0.4880(2) -0.12884(15) 0.66077(14) 0.0294(4) Uani 1 1 d . . . C2 C 0.4150(3) -0.0246(2) 0.61626(17) 0.0208(5) Uani 1 1 d . . . C5 C 0.2476(3) -0.0003(2) 0.57741(18) 0.0234(5) Uani 1 1 d . . . H5 H 0.2109 -0.0662 0.5936 0.028 Uiso 1 1 calc R . . C6 C 0.1553(3) 0.2230(2) 0.48688(17) 0.0204(5) Uani 1 1 d . . . C9 C 0.1430(3) 0.1007(2) 0.52333(18) 0.0229(5) Uani 1 1 d . . . H9A H 0.0468 0.0935 0.5055 0.028 Uiso 1 1 calc R . . O2 O 0.4203(2) 0.64373(15) 0.48440(12) 0.0248(4) Uani 1 1 d . . . O1 O -0.2500(2) 0.60387(15) 0.30457(14) 0.0291(4) Uani 1 1 d . . . N3 N 0.0413(2) 0.81753(17) 0.28451(14) 0.0194(4) Uani 1 1 d . . . O3 O 0.4831(2) 0.63595(18) 0.68302(14) 0.0362(5) Uani 1 1 d . . . H3 H 0.5092 0.6956 0.6737 0.054 Uiso 1 1 calc R . . N1 N -0.2031(2) 0.78421(17) 0.25195(15) 0.0197(4) Uani 1 1 d . . . N4 N 0.2417(2) 0.63202(17) 0.37094(14) 0.0201(4) Uani 1 1 d . . . N5 N 0.1007(2) 0.51007(18) 0.38663(15) 0.0221(4) Uani 1 1 d . . . N2 N -0.1736(3) 0.97043(19) 0.19729(16) 0.0242(5) Uani 1 1 d . . . C13 C 0.2423(3) 0.5178(2) 0.40593(18) 0.0226(5) Uani 1 1 d . . . H13 H 0.3289 0.4548 0.4385 0.027 Uiso 1 1 calc R . . C14 C -0.1582(3) 0.6619(2) 0.29947(17) 0.0201(5) Uani 1 1 d . . . C15 C -0.1084(3) 0.8559(2) 0.24574(17) 0.0189(5) Uani 1 1 d . . . C16 C 0.0910(3) 0.6992(2) 0.32812(16) 0.0182(5) Uani 1 1 d . . . C17 C 0.3838(3) 0.6691(2) 0.38117(18) 0.0241(5) Uani 1 1 d . . . H17A H 0.4734 0.6293 0.3527 0.029 Uiso 1 1 calc R . . H17B H 0.3644 0.7525 0.3421 0.029 Uiso 1 1 calc R . . C18 C 0.0039(3) 0.6218(2) 0.33742(17) 0.0191(5) Uani 1 1 d . . . C19 C 0.3271(3) 0.6664(2) 0.64020(19) 0.0273(6) Uani 1 1 d . . . H19A H 0.2565 0.7189 0.6681 0.033 Uiso 1 1 calc R . . H19B H 0.2907 0.5964 0.6603 0.033 Uiso 1 1 calc R . . C20 C 0.3184(3) 0.7241(2) 0.52459(19) 0.0250(5) Uani 1 1 d . . . H20A H 0.2099 0.7447 0.4980 0.030 Uiso 1 1 calc R . . H20B H 0.3527 0.7951 0.5034 0.030 Uiso 1 1 calc R . . H1N H -0.306(4) 0.818(3) 0.231(2) 0.030(8) Uiso 1 1 d . . . H2B H -0.266(4) 0.993(3) 0.173(2) 0.035(8) Uiso 1 1 d . . . H2A H -0.118(4) 1.020(3) 0.196(2) 0.041(9) Uiso 1 1 d . . . H5N H 0.073(4) 0.436(3) 0.402(2) 0.046(9) Uiso 1 1 d . . . H9 H 0.410(4) 0.127(2) 0.571(3) 0.055 Uiso 1 1 d D . . O11 O -0.5135(2) 1.06167(16) 0.11907(14) 0.0294(4) Uani 1 1 d D . . O14 O -0.9212(2) 1.32732(15) -0.06366(13) 0.0280(4) Uani 1 1 d . . . O12 O -0.5146(2) 0.87719(15) 0.16387(14) 0.0299(4) Uani 1 1 d . . . O13 O -0.6907(2) 1.25390(15) 0.02767(14) 0.0279(4) Uani 1 1 d . . . C21 C -0.7313(3) 1.0178(2) 0.05910(19) 0.0249(5) Uani 1 1 d . . . H21 H -0.7662 0.9558 0.0585 0.030 Uiso 1 1 calc R . . C22 C -0.8279(3) 1.1237(2) 0.00705(18) 0.0231(5) Uani 1 1 d . . . H22 H -0.9198 1.1234 -0.0227 0.028 Uiso 1 1 calc R . . C23 C -0.8122(3) 1.2422(2) -0.01093(17) 0.0211(5) Uani 1 1 d . . . C24 C -0.5773(3) 0.9827(2) 0.11776(18) 0.0216(5) Uani 1 1 d . . . H11 H -0.575(5) 1.128(2) 0.085(3) 0.073(13) Uiso 1 1 d D . . O5 O 1.2769(2) -0.21717(15) 0.98620(13) 0.0296(4) Uani 1 1 d . . . O4 O 0.7728(2) -0.37998(16) 0.77908(14) 0.0310(4) Uani 1 1 d . . . N10 N 1.1007(2) -0.45954(18) 0.89728(16) 0.0241(5) Uani 1 1 d . . . O6 O 1.4528(3) -0.48080(17) 1.11194(14) 0.0376(5) Uani 1 1 d . . . H6A H 1.4475 -0.5374 1.1641 0.056 Uiso 1 1 calc R . . N8 N 1.0193(2) -0.15042(17) 0.78925(14) 0.0203(4) Uani 1 1 d . . . N6 N 0.7986(3) -0.19531(18) 0.73823(15) 0.0217(4) Uani 1 1 d . . . N9 N 1.2131(2) -0.32621(17) 0.89741(15) 0.0233(5) Uani 1 1 d . . . N7 N 0.8057(3) -0.00427(19) 0.69253(16) 0.0243(5) Uani 1 1 d . . . C1 C 1.0738(3) -0.2678(2) 0.83650(17) 0.0190(5) Uani 1 1 d . . . C3 C 0.8780(3) -0.1183(2) 0.74162(16) 0.0188(5) Uani 1 1 d . . . C4 C 0.8526(3) -0.3178(2) 0.78505(18) 0.0217(5) Uani 1 1 d . . . C7 C 1.2235(3) -0.4420(2) 0.93353(19) 0.0262(5) Uani 1 1 d . . . H7C H 1.3053 -0.5007 0.9775 0.031 Uiso 1 1 calc R . . C8 C 1.4305(4) -0.3808(3) 1.1376(2) 0.0345(6) Uani 1 1 d . . . H8A H 1.5167 -0.3449 1.1116 0.041 Uiso 1 1 calc R . . H8B H 1.4339 -0.4052 1.2122 0.041 Uiso 1 1 calc R . . C10 C 1.2753(3) -0.2928(2) 1.0930(2) 0.0325(6) Uani 1 1 d . . . H10B H 1.1950 -0.3339 1.0994 0.039 Uiso 1 1 calc R . . H10A H 1.2445 -0.2448 1.1337 0.039 Uiso 1 1 calc R . . C11 C 1.0039(3) -0.3512(2) 0.83628(17) 0.0211(5) Uani 1 1 d . . . C12 C 1.3298(3) -0.2727(2) 0.91808(19) 0.0272(6) Uani 1 1 d . . . H12A H 1.4280 -0.3328 0.9467 0.033 Uiso 1 1 calc R . . H12 H 1.3524 -0.2162 0.8534 0.033 Uiso 1 1 calc R . . H7A H 0.709(4) 0.017(2) 0.668(2) 0.018(6) Uiso 1 1 d . . . H6N H 0.702(4) -0.167(3) 0.708(2) 0.028(7) Uiso 1 1 d . . . H7B H 0.856(4) 0.049(3) 0.694(2) 0.043(9) Uiso 1 1 d . . . H10N H 1.092(4) -0.539(3) 0.908(2) 0.035(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O9 0.0216(9) 0.0201(9) 0.0361(10) -0.0037(7) -0.0060(7) -0.0060(7) O7 0.0214(9) 0.0178(9) 0.0345(9) -0.0052(7) -0.0030(7) -0.0021(7) O8 0.0245(9) 0.0178(9) 0.0396(10) -0.0048(7) -0.0066(7) -0.0068(7) O10 0.0265(9) 0.0190(9) 0.0377(10) -0.0073(8) -0.0111(8) -0.0007(7) C2 0.0217(12) 0.0184(12) 0.0201(11) -0.0054(9) 0.0008(9) -0.0048(10) C5 0.0237(13) 0.0182(12) 0.0294(12) -0.0076(10) 0.0005(10) -0.0091(10) C6 0.0197(12) 0.0187(12) 0.0209(11) -0.0061(9) 0.0009(9) -0.0042(10) C9 0.0183(12) 0.0205(12) 0.0293(12) -0.0090(10) -0.0022(10) -0.0044(10) O2 0.0198(9) 0.0268(9) 0.0281(9) -0.0134(7) -0.0039(7) -0.0012(7) O1 0.0194(9) 0.0192(9) 0.0458(10) -0.0074(8) -0.0055(7) -0.0067(7) N3 0.0191(10) 0.0164(10) 0.0207(9) -0.0048(8) -0.0021(8) -0.0043(8) O3 0.0415(11) 0.0354(11) 0.0310(10) -0.0064(9) -0.0083(8) -0.0165(9) N1 0.0152(10) 0.0169(10) 0.0248(10) -0.0065(8) -0.0025(8) -0.0023(8) N4 0.0172(10) 0.0193(10) 0.0229(10) -0.0072(8) -0.0016(8) -0.0041(8) N5 0.0202(10) 0.0169(10) 0.0260(10) -0.0061(8) -0.0019(8) -0.0024(9) N2 0.0227(12) 0.0156(10) 0.0319(11) -0.0061(9) -0.0086(9) -0.0036(9) C13 0.0206(12) 0.0202(12) 0.0262(12) -0.0087(10) -0.0006(9) -0.0039(10) C14 0.0202(12) 0.0161(12) 0.0221(11) -0.0064(9) -0.0008(9) -0.0031(10) C15 0.0217(12) 0.0178(11) 0.0180(10) -0.0069(9) 0.0001(9) -0.0064(10) C16 0.0162(11) 0.0212(12) 0.0160(10) -0.0060(9) 0.0002(9) -0.0048(9) C17 0.0198(12) 0.0274(13) 0.0256(12) -0.0091(10) -0.0017(10) -0.0077(10) C18 0.0183(11) 0.0143(11) 0.0205(11) -0.0043(9) -0.0016(9) -0.0008(9) C19 0.0310(14) 0.0259(13) 0.0286(13) -0.0125(11) 0.0028(11) -0.0104(11) C20 0.0202(12) 0.0241(13) 0.0339(13) -0.0152(11) 0.0018(10) -0.0048(10) O11 0.0235(9) 0.0209(10) 0.0393(10) -0.0055(8) -0.0070(8) -0.0060(8) O14 0.0265(9) 0.0181(9) 0.0342(9) -0.0055(7) -0.0034(8) -0.0032(8) O12 0.0249(9) 0.0195(9) 0.0385(10) -0.0058(8) -0.0073(8) -0.0015(8) O13 0.0259(9) 0.0202(9) 0.0376(10) -0.0088(7) -0.0023(8) -0.0084(7) C21 0.0249(13) 0.0186(12) 0.0319(13) -0.0096(10) -0.0035(10) -0.0059(10) C22 0.0208(12) 0.0212(13) 0.0271(12) -0.0092(10) -0.0035(10) -0.0045(10) C23 0.0232(12) 0.0165(12) 0.0210(11) -0.0054(9) 0.0039(10) -0.0047(10) C24 0.0190(12) 0.0188(12) 0.0232(11) -0.0055(10) 0.0022(9) -0.0032(10) O5 0.0340(10) 0.0233(9) 0.0339(9) -0.0124(8) -0.0019(8) -0.0087(8) O4 0.0296(10) 0.0221(9) 0.0431(10) -0.0111(8) -0.0082(8) -0.0097(8) N10 0.0220(11) 0.0157(10) 0.0313(11) -0.0050(8) -0.0029(9) -0.0049(8) O6 0.0456(12) 0.0294(10) 0.0292(9) -0.0064(8) 0.0067(9) -0.0047(9) N8 0.0211(10) 0.0179(10) 0.0208(9) -0.0054(8) -0.0019(8) -0.0058(8) N6 0.0193(11) 0.0192(11) 0.0246(10) -0.0063(8) -0.0041(9) -0.0041(9) N9 0.0197(10) 0.0185(10) 0.0277(10) -0.0040(8) -0.0055(8) -0.0047(8) N7 0.0213(11) 0.0191(11) 0.0293(11) -0.0053(9) -0.0062(9) -0.0046(9) C1 0.0172(11) 0.0197(12) 0.0190(11) -0.0055(9) 0.0000(9) -0.0059(10) C3 0.0204(12) 0.0191(12) 0.0173(10) -0.0067(9) 0.0021(9) -0.0065(10) C4 0.0246(13) 0.0188(12) 0.0221(11) -0.0081(9) 0.0020(9) -0.0063(10) C7 0.0235(12) 0.0184(12) 0.0321(13) -0.0043(10) -0.0008(10) -0.0056(10) C8 0.0371(15) 0.0341(15) 0.0301(13) -0.0066(12) 0.0011(12) -0.0145(13) C10 0.0327(15) 0.0321(15) 0.0383(14) -0.0170(12) 0.0070(12) -0.0133(12) C11 0.0198(12) 0.0209(12) 0.0213(11) -0.0068(9) -0.0004(9) -0.0048(10) C12 0.0246(13) 0.0243(13) 0.0310(13) -0.0062(10) -0.0037(10) -0.0094(11) _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 O9 C2 1.275(3) . ? O9 H9 0.857(19) . ? O7 C6 1.233(3) . ? O8 C6 1.293(3) . ? O10 C2 1.239(3) . ? C2 C5 1.503(3) . ? C5 C9 1.335(4) . ? C5 H5 0.9300 . ? C6 C9 1.488(3) . ? C9 H9A 0.9300 . ? O2 C17 1.393(3) . ? O2 C20 1.440(3) . ? O1 C14 1.219(3) . ? N3 C15 1.336(3) . ? N3 C16 1.356(3) . ? O3 C19 1.416(3) . ? O3 H3 0.8200 . ? N1 C15 1.374(3) . ? N1 C14 1.401(3) . ? N1 H1N 0.90(3) . ? N4 C13 1.357(3) . ? N4 C16 1.387(3) . ? N4 C17 1.480(3) . ? N5 C13 1.322(3) . ? N5 C18 1.382(3) . ? N5 H5N 0.99(4) . ? N2 C15 1.334(3) . ? N2 H2B 0.82(4) . ? N2 H2A 0.89(4) . ? C13 H13 0.9300 . ? C14 C18 1.430(3) . ? C16 C18 1.374(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C19 C20 1.499(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? O11 C24 1.291(3) . ? O11 H11 0.848(19) . ? O14 C23 1.246(3) . ? O12 C24 1.235(3) . ? O13 C23 1.290(3) . ? C21 C22 1.338(3) . ? C21 C24 1.488(3) . ? C21 H21 0.9300 . ? C22 C23 1.489(3) . ? C22 H22 0.9300 . ? O5 C12 1.390(3) . ? O5 C10 1.441(3) . ? O4 C4 1.222(3) . ? N10 C7 1.322(4) . ? N10 C11 1.386(3) . ? N10 H10N 1.00(3) . ? O6 C8 1.426(4) . ? O6 H6A 0.8200 . ? N8 C3 1.325(3) . ? N8 C1 1.351(3) . ? N6 C3 1.371(3) . ? N6 C4 1.406(3) . ? N6 H6N 0.89(3) . ? N9 C7 1.355(3) . ? N9 C1 1.384(3) . ? N9 C12 1.473(3) . ? N7 C3 1.341(3) . ? N7 H7A 0.86(3) . ? N7 H7B 0.91(4) . ? C1 C11 1.373(3) . ? C4 C11 1.422(3) . ? C7 H7C 0.9300 . ? C8 C10 1.498(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 H10B 0.9700 . ? C10 H10A 0.9700 . ? C12 H12A 0.9700 . ? C12 H12 0.9700 . ? 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 C2 O9 H9 113(3) . . ? O10 C2 O9 123.3(2) . . ? O10 C2 C5 116.4(2) . . ? O9 C2 C5 120.3(2) . . ? C9 C5 C2 130.4(2) . . ? C9 C5 H5 114.8 . . ? C2 C5 H5 114.8 . . ? O7 C6 O8 121.9(2) . . ? O7 C6 C9 117.9(2) . . ? O8 C6 C9 120.2(2) . . ? C5 C9 C6 130.5(2) . . ? C5 C9 H9A 114.7 . . ? C6 C9 H9A 114.7 . . ? C17 O2 C20 113.56(19) . . ? C15 N3 C16 112.2(2) . . ? C19 O3 H3 109.5 . . ? C15 N1 C14 125.5(2) . . ? C15 N1 H1N 118(2) . . ? C14 N1 H1N 116(2) . . ? C13 N4 C16 108.0(2) . . ? C13 N4 C17 122.3(2) . . ? C16 N4 C17 129.7(2) . . ? C13 N5 C18 108.4(2) . . ? C13 N5 H5N 125(2) . . ? C18 N5 H5N 127(2) . . ? C15 N2 H2B 119(2) . . ? C15 N2 H2A 119(2) . . ? H2B N2 H2A 122(3) . . ? N5 C13 N4 109.5(2) . . ? N5 C13 H13 125.3 . . ? N4 C13 H13 125.3 . . ? O1 C14 N1 122.0(2) . . ? O1 C14 C18 128.2(2) . . ? N1 C14 C18 109.8(2) . . ? N2 C15 N3 119.6(2) . . ? N2 C15 N1 116.3(2) . . ? N3 C15 N1 124.0(2) . . ? N3 C16 C18 127.2(2) . . ? N3 C16 N4 126.5(2) . . ? C18 C16 N4 106.3(2) . . ? O2 C17 N4 110.91(19) . . ? O2 C17 H17A 109.5 . . ? N4 C17 H17A 109.5 . . ? O2 C17 H17B 109.5 . . ? N4 C17 H17B 109.5 . . ? H17A C17 H17B 108.0 . . ? C16 C18 N5 107.9(2) . . ? C16 C18 C14 121.2(2) . . ? N5 C18 C14 131.0(2) . . ? O3 C19 C20 112.2(2) . . ? O3 C19 H19A 109.2 . . ? C20 C19 H19A 109.2 . . ? O3 C19 H19B 109.2 . . ? C20 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? O2 C20 C19 108.4(2) . . ? O2 C20 H20A 110.0 . . ? C19 C20 H20A 110.0 . . ? O2 C20 H20B 110.0 . . ? C19 C20 H20B 110.0 . . ? H20A C20 H20B 108.4 . . ? C24 O11 H11 109(3) . . ? C22 C21 C24 130.6(2) . . ? C22 C21 H21 114.7 . . ? C24 C21 H21 114.7 . . ? C21 C22 C23 130.5(2) . . ? C21 C22 H22 114.7 . . ? C23 C22 H22 114.7 . . ? O14 C23 O13 122.6(2) . . ? O14 C23 C22 116.9(2) . . ? O13 C23 C22 120.5(2) . . ? O12 C24 O11 122.2(2) . . ? O12 C24 C21 117.9(2) . . ? O11 C24 C21 119.9(2) . . ? C12 O5 C10 116.0(2) . . ? C7 N10 C11 107.8(2) . . ? C7 N10 H10N 123.1(19) . . ? C11 N10 H10N 128.8(19) . . ? C8 O6 H6A 109.5 . . ? C3 N8 C1 112.1(2) . . ? C3 N6 C4 125.6(2) . . ? C3 N6 H6N 119(2) . . ? C4 N6 H6N 116(2) . . ? C7 N9 C1 107.4(2) . . ? C7 N9 C12 126.2(2) . . ? C1 N9 C12 126.4(2) . . ? C3 N7 H7A 120.0(18) . . ? C3 N7 H7B 119(2) . . ? H7A N7 H7B 121(3) . . ? N8 C1 C11 128.0(2) . . ? N8 C1 N9 125.0(2) . . ? C11 C1 N9 106.9(2) . . ? N8 C3 N7 119.6(2) . . ? N8 C3 N6 123.9(2) . . ? N7 C3 N6 116.5(2) . . ? O4 C4 N6 121.2(2) . . ? O4 C4 C11 128.8(2) . . ? N6 C4 C11 110.0(2) . . ? N10 C7 N9 110.3(2) . . ? N10 C7 H7C 124.9 . . ? N9 C7 H7C 124.9 . . ? O6 C8 C10 111.7(2) . . ? O6 C8 H8A 109.3 . . ? C10 C8 H8A 109.3 . . ? O6 C8 H8B 109.3 . . ? C10 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? O5 C10 C8 114.7(2) . . ? O5 C10 H10B 108.6 . . ? C8 C10 H10B 108.6 . . ? O5 C10 H10A 108.6 . . ? C8 C10 H10A 108.6 . . ? H10B C10 H10A 107.6 . . ? C1 C11 N10 107.7(2) . . ? C1 C11 C4 120.3(2) . . ? N10 C11 C4 131.8(2) . . ? O5 C12 N9 112.7(2) . . ? O5 C12 H12A 109.1 . . ? N9 C12 H12A 109.1 . . ? O5 C12 H12 109.1 . . ? N9 C12 H12 109.1 . . ? H12A C12 H12 107.8 . . ? 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 O10 C2 C5 C9 -176.6(2) . . . . ? O9 C2 C5 C9 3.7(4) . . . . ? C2 C5 C9 C6 -2.5(4) . . . . ? O7 C6 C9 C5 -179.4(2) . . . . ? O8 C6 C9 C5 -0.7(4) . . . . ? C18 N5 C13 N4 0.1(3) . . . . ? C16 N4 C13 N5 0.4(3) . . . . ? C17 N4 C13 N5 -179.9(2) . . . . ? C15 N1 C14 O1 177.9(2) . . . . ? C15 N1 C14 C18 -2.3(3) . . . . ? C16 N3 C15 N2 -177.97(19) . . . . ? C16 N3 C15 N1 1.8(3) . . . . ? C14 N1 C15 N2 -179.9(2) . . . . ? C14 N1 C15 N3 0.3(3) . . . . ? C15 N3 C16 C18 -2.0(3) . . . . ? C15 N3 C16 N4 176.9(2) . . . . ? C13 N4 C16 N3 -179.9(2) . . . . ? C17 N4 C16 N3 0.4(4) . . . . ? C13 N4 C16 C18 -0.8(2) . . . . ? C17 N4 C16 C18 179.5(2) . . . . ? C20 O2 C17 N4 -77.0(2) . . . . ? C13 N4 C17 O2 -68.1(3) . . . . ? C16 N4 C17 O2 111.5(2) . . . . ? N3 C16 C18 N5 -180.0(2) . . . . ? N4 C16 C18 N5 0.9(2) . . . . ? N3 C16 C18 C14 -0.1(4) . . . . ? N4 C16 C18 C14 -179.2(2) . . . . ? C13 N5 C18 C16 -0.7(3) . . . . ? C13 N5 C18 C14 179.4(2) . . . . ? O1 C14 C18 C16 -178.1(2) . . . . ? N1 C14 C18 C16 2.1(3) . . . . ? O1 C14 C18 N5 1.7(4) . . . . ? N1 C14 C18 N5 -178.0(2) . . . . ? C17 O2 C20 C19 159.6(2) . . . . ? O3 C19 C20 O2 60.5(3) . . . . ? C24 C21 C22 C23 1.1(4) . . . . ? C21 C22 C23 O14 179.6(2) . . . . ? C21 C22 C23 O13 -0.9(4) . . . . ? C22 C21 C24 O12 176.4(2) . . . . ? C22 C21 C24 O11 -3.7(4) . . . . ? C3 N8 C1 C11 2.7(3) . . . . ? C3 N8 C1 N9 -175.8(2) . . . . ? C7 N9 C1 N8 177.9(2) . . . . ? C12 N9 C1 N8 -2.9(4) . . . . ? C7 N9 C1 C11 -0.9(3) . . . . ? C12 N9 C1 C11 178.4(2) . . . . ? C1 N8 C3 N7 178.70(19) . . . . ? C1 N8 C3 N6 -1.8(3) . . . . ? C4 N6 C3 N8 1.0(3) . . . . ? C4 N6 C3 N7 -179.5(2) . . . . ? C3 N6 C4 O4 179.1(2) . . . . ? C3 N6 C4 C11 -0.6(3) . . . . ? C11 N10 C7 N9 -1.0(3) . . . . ? C1 N9 C7 N10 1.2(3) . . . . ? C12 N9 C7 N10 -178.0(2) . . . . ? C12 O5 C10 C8 54.0(3) . . . . ? O6 C8 C10 O5 -81.9(3) . . . . ? N8 C1 C11 N10 -178.5(2) . . . . ? N9 C1 C11 N10 0.2(2) . . . . ? N8 C1 C11 C4 -2.6(4) . . . . ? N9 C1 C11 C4 176.1(2) . . . . ? C7 N10 C11 C1 0.5(3) . . . . ? C7 N10 C11 C4 -174.7(2) . . . . ? O4 C4 C11 C1 -178.4(2) . . . . ? N6 C4 C11 C1 1.3(3) . . . . ? O4 C4 C11 N10 -3.7(4) . . . . ? N6 C4 C11 N10 176.0(2) . . . . ? C10 O5 C12 N9 73.5(3) . . . . ? C7 N9 C12 O5 -106.8(3) . . . . ? C1 N9 C12 O5 74.1(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 O3 H3 O10 0.82 2.15 2.932(3) 159.0 1_565 N2 H2A N8 0.89(4) 2.17(4) 3.046(3) 169(3) 2_666 O6 H6A O3 0.82 2.06 2.784(3) 147.7 2_757 O6 H6A O4 0.82 2.40 2.983(3) 128.8 2_747 N7 H7B N3 0.91(4) 2.26(4) 3.170(3) 172(3) 2_666 N10 H10N O14 1.00(3) 1.64(3) 2.641(3) 175(3) 1_736 _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 67.01 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.607 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 915143' ####################################################################### # # 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_exp_1034 #TrackingRef 'web_deposit_cif_file_1_YanYan_1355189863.ACVGA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H19 N5 O7' _chemical_formula_weight 357.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1849(10) _cell_length_b 8.8476(9) _cell_length_c 11.6567(12) _cell_angle_alpha 70.210(9) _cell_angle_beta 86.985(9) _cell_angle_gamma 80.948(9) _cell_volume 784.39(15) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2285 _cell_measurement_theta_min 4.0271 _cell_measurement_theta_max 66.7638 _exptl_crystal_description sheep _exptl_crystal_colour colorless _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 1.064 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9688 _exptl_absorpt_correction_T_max 0.9894 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4671 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.03 _diffrn_reflns_theta_max 66.87 _reflns_number_total 2711 _reflns_number_gt 2318 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0579P)^2^+0.1282P] 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 2711 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.1011 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 O2 O 0.22387(15) 0.84145(15) 0.84944(11) 0.0335(3) Uani 1 1 d . . . O3 O 0.05616(15) 0.70797(15) 0.45269(11) 0.0330(3) Uani 1 1 d . . . O1 O 0.47574(15) 0.71931(16) 0.91984(11) 0.0328(3) Uani 1 1 d . . . O4 O 0.25613(18) 0.54245(19) 0.40034(14) 0.0468(4) Uani 1 1 d . . . C4 C 0.3508(2) 0.7521(2) 0.84398(15) 0.0251(4) Uani 1 1 d . . . C5 C 0.3130(2) 0.6170(2) 0.56581(16) 0.0276(4) Uani 1 1 d . . . C6 C 0.2510(2) 0.7010(2) 0.65676(15) 0.0279(4) Uani 1 1 d . . . C10 C 0.1936(2) 0.6284(2) 0.46841(15) 0.0266(4) Uani 1 1 d . . . C11 C 0.3847(2) 0.6655(2) 0.75230(16) 0.0282(4) Uani 1 1 d . . . H6B H 0.148(3) 0.660(3) 0.695(2) 0.038(5) Uiso 1 1 d . . . H5A H 0.412(3) 0.656(3) 0.525(2) 0.045(6) Uiso 1 1 d . . . H11A H 0.486(3) 0.691(2) 0.7135(19) 0.034(5) Uiso 1 1 d . . . H5B H 0.351(3) 0.500(3) 0.607(2) 0.041(6) Uiso 1 1 d . . . H6A H 0.227(3) 0.822(3) 0.613(2) 0.044(6) Uiso 1 1 d . . . H11B H 0.402(3) 0.549(3) 0.800(2) 0.040(6) Uiso 1 1 d . . . H1O H 0.453(3) 0.769(3) 0.978(2) 0.054(7) Uiso 1 1 d . . . H4O H 0.185(4) 0.552(4) 0.336(3) 0.073(9) Uiso 1 1 d . . . O6 O 0.17378(14) 1.22188(14) 1.25470(10) 0.0287(3) Uani 1 1 d . . . O7 O 0.78692(16) 0.71979(16) 1.14770(11) 0.0359(3) Uani 1 1 d . . . N1 N 0.74302(18) 0.79878(17) 1.31607(12) 0.0256(3) Uani 1 1 d . . . N3 N 0.49153(17) 0.94121(16) 1.36345(12) 0.0248(3) Uani 1 1 d . . . C1 C 0.5214(2) 0.8501(2) 1.18497(14) 0.0258(4) Uani 1 1 d . . . N5 N 0.41748(18) 0.85544(18) 1.09258(13) 0.0297(3) Uani 1 1 d . . . O5 O 0.08353(17) 1.55827(17) 1.22058(12) 0.0393(3) Uani 1 1 d . . . C2 C 0.4370(2) 0.92469(19) 1.26133(15) 0.0239(3) Uani 1 1 d . . . N2 N 0.7176(2) 0.87069(19) 1.49020(13) 0.0300(3) Uani 1 1 d . . . N4 N 0.27915(17) 0.97837(17) 1.21516(13) 0.0267(3) Uani 1 1 d . . . C3 C 0.6475(2) 0.87146(19) 1.38938(14) 0.0238(3) Uani 1 1 d . . . C7 C 0.1751(2) 1.4991(2) 1.13311(17) 0.0314(4) Uani 1 1 d . . . C8 C 0.1343(2) 1.3383(2) 1.13577(15) 0.0286(4) Uani 1 1 d . . . C9 C 0.6903(2) 0.7847(2) 1.20884(15) 0.0261(4) Uani 1 1 d . . . C12 C 0.1436(2) 1.0653(2) 1.26664(17) 0.0298(4) Uani 1 1 d . . . C13 C 0.2756(2) 0.9326(2) 1.11402(16) 0.0295(4) Uani 1 1 d . . . H12C H 0.138(2) 1.005(2) 1.3576(18) 0.026(5) Uiso 1 1 d . . . H12D H 0.040(3) 1.066(2) 1.2246(17) 0.027(5) Uiso 1 1 d . . . H8B H 0.202(3) 1.307(2) 1.0695(19) 0.034(5) Uiso 1 1 d . . . H8A H 0.010(3) 1.347(2) 1.1190(19) 0.036(5) Uiso 1 1 d . . . H13A H 0.174(3) 0.956(2) 1.0638(19) 0.033(5) Uiso 1 1 d . . . H7B H 0.293(3) 1.486(2) 1.1523(19) 0.034(5) Uiso 1 1 d . . . H2N H 0.813(3) 0.813(3) 1.514(2) 0.038(6) Uiso 1 1 d . . . H7A H 0.154(3) 1.582(3) 1.047(2) 0.040(6) Uiso 1 1 d . . . H1N H 0.852(3) 0.762(2) 1.3374(19) 0.033(5) Uiso 1 1 d . . . H3N H 0.654(3) 0.914(3) 1.538(2) 0.035(5) Uiso 1 1 d . . . H5O H -0.013(4) 1.616(3) 1.195(3) 0.065(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0229(6) 0.0439(7) 0.0377(7) -0.0212(6) -0.0073(5) 0.0029(5) O3 0.0257(6) 0.0424(7) 0.0339(6) -0.0199(5) -0.0082(5) 0.0052(5) O1 0.0251(6) 0.0465(7) 0.0325(7) -0.0234(6) -0.0088(5) 0.0034(5) O4 0.0378(8) 0.0663(9) 0.0464(8) -0.0405(7) -0.0194(7) 0.0176(7) C4 0.0216(8) 0.0299(8) 0.0248(8) -0.0094(7) -0.0042(6) -0.0046(7) C5 0.0251(9) 0.0320(9) 0.0273(8) -0.0126(7) -0.0050(7) -0.0012(7) C6 0.0244(9) 0.0351(10) 0.0269(8) -0.0145(7) -0.0056(7) -0.0016(7) C10 0.0259(9) 0.0292(8) 0.0258(8) -0.0114(7) -0.0034(7) -0.0017(7) C11 0.0248(9) 0.0334(10) 0.0286(9) -0.0136(8) -0.0055(7) -0.0014(7) O6 0.0281(6) 0.0339(6) 0.0240(6) -0.0124(5) -0.0069(5) 0.0040(5) O7 0.0292(7) 0.0502(8) 0.0310(6) -0.0233(6) -0.0061(5) 0.0104(6) N1 0.0210(7) 0.0323(7) 0.0249(7) -0.0134(6) -0.0046(6) 0.0025(6) N3 0.0231(7) 0.0290(7) 0.0235(7) -0.0122(6) -0.0039(5) 0.0014(6) C1 0.0245(8) 0.0315(8) 0.0229(8) -0.0119(7) -0.0051(7) -0.0006(7) N5 0.0278(8) 0.0363(8) 0.0282(7) -0.0163(6) -0.0080(6) 0.0009(6) O5 0.0345(7) 0.0494(8) 0.0391(7) -0.0281(6) -0.0146(6) 0.0139(6) C2 0.0210(8) 0.0264(8) 0.0236(8) -0.0085(6) -0.0034(6) -0.0004(6) N2 0.0261(8) 0.0402(8) 0.0258(7) -0.0181(7) -0.0079(6) 0.0075(7) N4 0.0200(7) 0.0325(7) 0.0289(7) -0.0136(6) -0.0060(6) 0.0017(6) C3 0.0254(8) 0.0242(8) 0.0220(8) -0.0088(6) -0.0013(6) -0.0014(6) C7 0.0244(9) 0.0400(10) 0.0305(9) -0.0154(8) -0.0066(7) 0.0030(7) C8 0.0242(9) 0.0388(10) 0.0229(8) -0.0128(7) -0.0062(7) 0.0029(7) C9 0.0258(9) 0.0292(8) 0.0242(8) -0.0122(7) -0.0024(7) 0.0014(7) C12 0.0214(9) 0.0350(9) 0.0337(9) -0.0146(8) -0.0039(7) 0.0020(7) C13 0.0258(9) 0.0355(9) 0.0296(8) -0.0144(7) -0.0085(7) -0.0005(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 O2 C4 1.215(2) . ? O3 C10 1.217(2) . ? O1 C4 1.319(2) . ? O1 H1O 0.92(3) . ? O4 C10 1.309(2) . ? O4 H4O 0.95(3) . ? C4 C11 1.504(2) . ? C5 C10 1.504(2) . ? C5 C6 1.514(2) . ? C5 H5A 0.97(2) . ? C5 H5B 0.99(2) . ? C6 C11 1.523(2) . ? C6 H6B 0.99(2) . ? C6 H6A 1.01(2) . ? C11 H11A 0.95(2) . ? C11 H11B 0.98(2) . ? O6 C12 1.404(2) . ? O6 C8 1.436(2) . ? O7 C9 1.240(2) . ? N1 C3 1.378(2) . ? N1 C9 1.394(2) . ? N1 H1N 0.92(2) . ? N3 C3 1.330(2) . ? N3 C2 1.353(2) . ? C1 C2 1.376(2) . ? C1 N5 1.391(2) . ? C1 C9 1.415(2) . ? N5 C13 1.309(2) . ? O5 C7 1.426(2) . ? O5 H5O 0.88(3) . ? C2 N4 1.375(2) . ? N2 C3 1.332(2) . ? N2 H2N 0.86(2) . ? N2 H3N 0.88(2) . ? N4 C13 1.373(2) . ? N4 C12 1.468(2) . ? C7 C8 1.501(3) . ? C7 H7B 0.98(2) . ? C7 H7A 1.02(2) . ? C8 H8B 1.02(2) . ? C8 H8A 1.03(2) . ? C12 H12C 1.02(2) . ? C12 H12D 1.00(2) . ? C13 H13A 1.00(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 C4 O1 H1O 112.0(16) . . ? C10 O4 H4O 113.2(18) . . ? O2 C4 O1 123.10(16) . . ? O2 C4 C11 124.88(15) . . ? O1 C4 C11 112.03(14) . . ? C10 C5 C6 116.85(15) . . ? C10 C5 H5A 106.9(14) . . ? C6 C5 H5A 111.3(14) . . ? C10 C5 H5B 106.0(13) . . ? C6 C5 H5B 111.7(13) . . ? H5A C5 H5B 103.0(18) . . ? C5 C6 C11 108.80(14) . . ? C5 C6 H6B 109.2(13) . . ? C11 C6 H6B 110.6(12) . . ? C5 C6 H6A 109.2(13) . . ? C11 C6 H6A 109.6(13) . . ? H6B C6 H6A 109.5(18) . . ? O3 C10 O4 123.28(15) . . ? O3 C10 C5 125.10(15) . . ? O4 C10 C5 111.61(14) . . ? C4 C11 C6 116.22(15) . . ? C4 C11 H11A 107.9(13) . . ? C6 C11 H11A 109.8(13) . . ? C4 C11 H11B 105.6(13) . . ? C6 C11 H11B 109.7(13) . . ? H11A C11 H11B 107.1(18) . . ? C12 O6 C8 113.23(13) . . ? C3 N1 C9 125.48(14) . . ? C3 N1 H1N 117.0(13) . . ? C9 N1 H1N 117.4(13) . . ? C3 N3 C2 112.16(14) . . ? C2 C1 N5 110.19(15) . . ? C2 C1 C9 118.84(15) . . ? N5 C1 C9 130.96(15) . . ? C13 N5 C1 104.63(14) . . ? C7 O5 H5O 114.4(19) . . ? N3 C2 N4 125.20(15) . . ? N3 C2 C1 128.75(15) . . ? N4 C2 C1 106.03(14) . . ? C3 N2 H2N 120.8(15) . . ? C3 N2 H3N 116.4(14) . . ? H2N N2 H3N 122(2) . . ? C13 N4 C2 106.14(14) . . ? C13 N4 C12 128.00(14) . . ? C2 N4 C12 125.86(14) . . ? N3 C3 N2 119.66(15) . . ? N3 C3 N1 123.06(14) . . ? N2 C3 N1 117.29(15) . . ? O5 C7 C8 112.73(15) . . ? O5 C7 H7B 107.4(12) . . ? C8 C7 H7B 108.8(12) . . ? O5 C7 H7A 110.3(13) . . ? C8 C7 H7A 109.2(13) . . ? H7B C7 H7A 108.3(17) . . ? O6 C8 C7 108.38(13) . . ? O6 C8 H8B 111.7(11) . . ? C7 C8 H8B 107.7(12) . . ? O6 C8 H8A 109.0(11) . . ? C7 C8 H8A 110.7(11) . . ? H8B C8 H8A 109.3(17) . . ? O7 C9 N1 120.65(15) . . ? O7 C9 C1 127.79(15) . . ? N1 C9 C1 111.56(14) . . ? O6 C12 N4 111.56(14) . . ? O6 C12 H12C 106.2(11) . . ? N4 C12 H12C 108.3(11) . . ? O6 C12 H12D 112.7(10) . . ? N4 C12 H12D 106.9(11) . . ? H12C C12 H12D 111.1(16) . . ? N5 C13 N4 113.00(15) . . ? N5 C13 H13A 124.7(12) . . ? N4 C13 H13A 122.3(12) . . ? 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 C10 C5 C6 C11 176.05(15) . . . . ? C6 C5 C10 O3 5.0(3) . . . . ? C6 C5 C10 O4 -175.58(16) . . . . ? O2 C4 C11 C6 3.0(3) . . . . ? O1 C4 C11 C6 -177.41(15) . . . . ? C5 C6 C11 C4 174.55(16) . . . . ? C2 C1 N5 C13 0.4(2) . . . . ? C9 C1 N5 C13 -178.84(18) . . . . ? C3 N3 C2 N4 177.16(15) . . . . ? C3 N3 C2 C1 -1.1(2) . . . . ? N5 C1 C2 N3 177.93(16) . . . . ? C9 C1 C2 N3 -2.7(3) . . . . ? N5 C1 C2 N4 -0.55(19) . . . . ? C9 C1 C2 N4 178.83(15) . . . . ? N3 C2 N4 C13 -178.12(16) . . . . ? C1 C2 N4 C13 0.43(18) . . . . ? N3 C2 N4 C12 1.3(3) . . . . ? C1 C2 N4 C12 179.83(15) . . . . ? C2 N3 C3 N2 -177.08(15) . . . . ? C2 N3 C3 N1 3.1(2) . . . . ? C9 N1 C3 N3 -1.6(3) . . . . ? C9 N1 C3 N2 178.57(16) . . . . ? C12 O6 C8 C7 -178.70(14) . . . . ? O5 C7 C8 O6 -60.52(18) . . . . ? C3 N1 C9 O7 178.55(16) . . . . ? C3 N1 C9 C1 -2.1(2) . . . . ? C2 C1 C9 O7 -176.79(17) . . . . ? N5 C1 C9 O7 2.4(3) . . . . ? C2 C1 C9 N1 3.9(2) . . . . ? N5 C1 C9 N1 -176.85(17) . . . . ? C8 O6 C12 N4 80.85(17) . . . . ? C13 N4 C12 O6 -112.39(18) . . . . ? C2 N4 C12 O6 68.3(2) . . . . ? C1 N5 C13 N4 -0.2(2) . . . . ? C2 N4 C13 N5 -0.2(2) . . . . ? C12 N4 C13 N5 -179.55(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 O1 H1O N5 0.92(3) 1.74(3) 2.6633(19) 177(2) . O4 H4O O5 0.95(3) 1.59(3) 2.5410(18) 173(3) 1_544 N2 H2N O3 0.86(2) 2.25(2) 2.998(2) 145(2) 1_656 N1 H1N O3 0.92(2) 2.09(2) 2.9437(19) 154.0(18) 1_656 N2 H3N N3 0.88(2) 2.18(2) 3.054(2) 170.5(19) 2_678 O5 H5O O7 0.88(3) 1.76(3) 2.6383(18) 176(3) 1_465 _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 66.87 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.163 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 915144' ####################################################################### # # 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_11110311 #TrackingRef 'web_deposit_cif_file_2_YanYan_1355189863.ACVFA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H21 N5 O11' _chemical_formula_weight 435.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.3178(15) _cell_length_b 6.4895(5) _cell_length_c 29.435(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.906(8) _cell_angle_gamma 90.00 _cell_volume 3952.7(5) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2001 _cell_measurement_theta_min 3.0908 _cell_measurement_theta_max 65.4387 _exptl_crystal_description bluk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.033 _exptl_crystal_size_mid 0.021 _exptl_crystal_size_min 0.020 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1824 _exptl_absorpt_coefficient_mu 1.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7110 _exptl_absorpt_correction_T_max 0.8086 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6647 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 65.54 _reflns_number_total 3312 _reflns_number_gt 2489 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0747P)^2^+5.1284P] 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 3312 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1408 _refine_ls_wR_factor_gt 0.1230 _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_restrained_S_all 0.981 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.002 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 O1W O 0.04652(13) 0.8359(4) 0.47378(9) 0.0660(8) Uani 1 1 d . . . H1B H 0.0287 0.7915 0.4948 0.099 Uiso 1 1 d R . . H1C H 0.0233 0.9289 0.4576 0.099 Uiso 1 1 d R . . O2W O 0.05509(9) 0.5100(3) 0.41941(7) 0.0351(5) Uani 1 1 d . . . H2C H 0.0945 0.4847 0.4322 0.053 Uiso 1 1 d R . . H2D H 0.0426 0.6143 0.4323 0.053 Uiso 1 1 d R . . C3 C 0.14983(11) 0.5562(4) 0.24519(8) 0.0185(5) Uani 1 1 d . . . C4 C 0.09529(11) 0.5456(4) 0.30108(8) 0.0195(5) Uani 1 1 d . . . C5 C 0.20944(11) 0.5297(4) 0.27548(8) 0.0191(5) Uani 1 1 d . . . C6 C 0.22718(11) 0.5561(4) 0.20700(8) 0.0202(5) Uani 1 1 d . . . H6 H 0.2482 0.5621 0.1820 0.024 Uiso 1 1 calc R . . C7 C 0.24003(13) 0.4972(4) 0.46072(9) 0.0250(6) Uani 1 1 d . . . C8 C 0.21366(11) 0.5099(4) 0.32377(8) 0.0189(5) Uani 1 1 d . . . C9 C 0.25161(13) 0.4999(4) 0.51215(9) 0.0263(6) Uani 1 1 d . . . H9 H 0.2150 0.5021 0.5253 0.032 Uiso 1 1 calc R . . C10 C 0.30945(13) 0.4995(4) 0.54121(9) 0.0260(6) Uani 1 1 d . . . C11 C 0.11452(12) 0.6205(4) 0.15753(8) 0.0240(6) Uani 1 1 d . . . H11A H 0.0853 0.7309 0.1632 0.029 Uiso 1 1 calc R . . H11B H 0.1374 0.6721 0.1343 0.029 Uiso 1 1 calc R . . C12 C 0.31576(13) 0.4953(4) 0.59269(9) 0.0262(6) Uani 1 1 d . . . C13 C 0.06761(14) 0.1300(5) 0.09897(10) 0.0350(7) Uani 1 1 d . . . H13A H 0.0923 0.0168 0.0889 0.042 Uiso 1 1 calc R . . H13B H 0.0477 0.0754 0.1236 0.042 Uiso 1 1 calc R . . C14 C 0.11294(13) 0.3005(4) 0.11896(9) 0.0301(6) Uani 1 1 d . . . H14A H 0.1498 0.2459 0.1432 0.036 Uiso 1 1 calc R . . H14B H 0.1301 0.3658 0.0940 0.036 Uiso 1 1 calc R . . N1 N 0.15342(9) 0.5230(3) 0.33373(7) 0.0195(5) Uani 1 1 d . . . H1 H 0.1521 0.5163 0.3634 0.023 Uiso 1 1 calc R . . N2 N 0.04188(10) 0.5481(3) 0.31701(7) 0.0245(5) Uani 1 1 d . . . H2A H 0.0038 0.5613 0.2973 0.029 Uiso 1 1 calc R . . H2B H 0.0446 0.5365 0.3472 0.029 Uiso 1 1 calc R . . N3 N 0.09118(9) 0.5632(3) 0.25538(7) 0.0192(4) Uani 1 1 d . . . N4 N 0.16188(9) 0.5747(3) 0.20139(7) 0.0194(5) Uani 1 1 d . . . N5 N 0.25745(9) 0.5289(3) 0.25088(7) 0.0193(5) Uani 1 1 d . . . O3 O 0.37657(9) 0.4750(4) 0.61652(6) 0.0365(5) Uani 1 1 d . . . H3 H 0.3780 0.4675 0.6452 0.055 Uiso 1 1 calc R . . O4 O 0.27050(9) 0.5069(4) 0.61036(7) 0.0424(6) Uani 1 1 d . . . O5 O 0.18534(9) 0.4926(3) 0.43547(6) 0.0300(5) Uani 1 1 d . . . O6 O 0.29173(9) 0.4984(3) 0.44439(6) 0.0347(5) Uani 1 1 d . . . H6A H 0.2810 0.4968 0.4150 0.052 Uiso 1 1 calc R . . O7 O 0.26389(8) 0.4808(3) 0.35487(6) 0.0247(4) Uani 1 1 d . . . O8 O 0.07779(8) 0.4481(3) 0.13915(6) 0.0253(4) Uani 1 1 d . . . O9 O 0.01795(9) 0.1951(3) 0.06020(6) 0.0341(5) Uani 1 1 d . . . H9A H -0.0024 0.2938 0.0684 0.051 Uiso 1 1 calc R . . C1 C 0.40932(12) 0.5524(4) 0.24853(8) 0.0196(5) Uani 1 1 d . . . C2 C 0.48084(12) 0.5562(4) 0.26455(9) 0.0225(5) Uani 1 1 d . . . H2 H 0.4998 0.5587 0.2972 0.027 Uiso 1 1 calc R . . O1 O 0.38056(8) 0.5402(3) 0.28272(6) 0.0235(4) Uani 1 1 d . . . H1A H 0.3403 0.5402 0.2719 0.035 Uiso 1 1 calc R . . O2 O 0.38014(8) 0.5597(3) 0.20711(6) 0.0254(4) Uani 1 1 d . . . H10 H 0.3481(16) 0.500(5) 0.5300(11) 0.039(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 O1W 0.0661(17) 0.0709(18) 0.0647(17) 0.0186(14) 0.0228(14) 0.0152(14) O2W 0.0213(10) 0.0513(13) 0.0323(11) -0.0006(9) 0.0057(8) -0.0005(9) C3 0.0175(12) 0.0217(13) 0.0165(12) 0.0002(10) 0.0046(9) 0.0001(10) C4 0.0174(12) 0.0224(13) 0.0192(12) -0.0021(10) 0.0051(10) 0.0007(10) C5 0.0147(12) 0.0243(13) 0.0187(12) 0.0006(10) 0.0051(10) -0.0002(10) C6 0.0172(12) 0.0270(13) 0.0178(12) -0.0005(10) 0.0073(10) -0.0001(10) C7 0.0242(14) 0.0290(14) 0.0219(13) -0.0002(11) 0.0056(11) 0.0001(11) C8 0.0156(12) 0.0217(12) 0.0203(12) -0.0018(10) 0.0059(10) -0.0014(10) C9 0.0278(14) 0.0320(15) 0.0207(14) -0.0001(11) 0.0088(11) -0.0014(11) C10 0.0252(14) 0.0342(15) 0.0201(14) -0.0022(11) 0.0080(11) -0.0028(11) C11 0.0218(13) 0.0324(14) 0.0169(12) 0.0019(11) 0.0028(10) 0.0028(11) C12 0.0278(14) 0.0320(14) 0.0197(13) 0.0001(11) 0.0076(11) -0.0014(11) C13 0.0355(16) 0.0378(16) 0.0293(15) 0.0005(13) 0.0031(12) 0.0033(13) C14 0.0256(14) 0.0359(15) 0.0292(15) -0.0053(12) 0.0073(11) 0.0066(12) N1 0.0157(10) 0.0300(11) 0.0138(10) -0.0013(8) 0.0051(8) -0.0014(8) N2 0.0145(10) 0.0429(13) 0.0169(10) -0.0001(9) 0.0053(8) 0.0009(9) N3 0.0142(10) 0.0259(11) 0.0188(11) 0.0003(9) 0.0065(8) 0.0001(9) N4 0.0142(10) 0.0288(11) 0.0158(10) 0.0003(9) 0.0044(8) -0.0004(9) N5 0.0156(10) 0.0244(11) 0.0198(10) -0.0004(8) 0.0077(8) -0.0012(8) O3 0.0246(10) 0.0688(15) 0.0160(9) 0.0003(10) 0.0044(8) -0.0009(10) O4 0.0278(11) 0.0806(17) 0.0200(10) 0.0022(10) 0.0081(8) 0.0050(10) O5 0.0204(10) 0.0484(12) 0.0205(10) 0.0020(8) 0.0036(8) -0.0007(8) O6 0.0220(10) 0.0656(14) 0.0168(9) 0.0006(9) 0.0052(8) -0.0018(9) O7 0.0147(9) 0.0416(11) 0.0169(9) -0.0006(7) 0.0024(7) 0.0009(8) O8 0.0189(9) 0.0350(10) 0.0217(9) -0.0053(8) 0.0044(7) -0.0002(8) O9 0.0348(11) 0.0378(12) 0.0276(10) -0.0067(8) 0.0032(8) 0.0041(9) C1 0.0179(12) 0.0221(12) 0.0196(13) -0.0008(10) 0.0064(10) -0.0004(10) C2 0.0166(12) 0.0327(14) 0.0179(12) 0.0017(11) 0.0037(9) 0.0007(11) O1 0.0132(8) 0.0402(11) 0.0180(9) -0.0003(8) 0.0057(7) 0.0004(8) O2 0.0179(9) 0.0417(11) 0.0165(9) 0.0005(8) 0.0038(7) 0.0006(8) _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 O1W H1B 0.8502 . ? O1W H1C 0.8502 . ? O2W H2C 0.8499 . ? O2W H2D 0.8503 . ? C3 N3 1.355(3) . ? C3 C5 1.376(3) . ? C3 N4 1.379(3) . ? C4 N3 1.332(3) . ? C4 N2 1.332(3) . ? C4 N1 1.382(3) . ? C5 N5 1.389(3) . ? C5 C8 1.408(3) . ? C6 N5 1.310(3) . ? C6 N4 1.367(3) . ? C6 H6 0.9500 . ? C7 O5 1.223(3) . ? C7 O6 1.304(3) . ? C7 C9 1.474(4) . ? C8 O7 1.245(3) . ? C8 N1 1.387(3) . ? C9 C10 1.321(4) . ? C9 H9 0.9500 . ? C10 C12 1.489(4) . ? C10 H10 0.96(3) . ? C11 O8 1.397(3) . ? C11 N4 1.465(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O4 1.203(3) . ? C12 O3 1.324(3) . ? C13 O9 1.421(3) . ? C13 C14 1.494(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 O8 1.431(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? N1 H1 0.8800 . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? O3 H3 0.8400 . ? O6 H6A 0.8400 . ? O9 H9A 0.8400 . ? C1 O2 1.229(3) . ? C1 O1 1.300(3) . ? C1 C2 1.484(3) . ? C2 C2 1.318(5) 2_655 ? C2 H2 0.9500 . ? O1 H1A 0.8400 . ? 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 H1B O1W H1C 110.2 . . ? H2C O2W H2D 109.8 . . ? N3 C3 C5 128.2(2) . . ? N3 C3 N4 126.4(2) . . ? C5 C3 N4 105.4(2) . . ? N3 C4 N2 120.0(2) . . ? N3 C4 N1 122.8(2) . . ? N2 C4 N1 117.1(2) . . ? C3 C5 N5 110.1(2) . . ? C3 C5 C8 119.4(2) . . ? N5 C5 C8 130.5(2) . . ? N5 C6 N4 112.2(2) . . ? N5 C6 H6 123.9 . . ? N4 C6 H6 123.9 . . ? O5 C7 O6 122.9(2) . . ? O5 C7 C9 121.6(2) . . ? O6 C7 C9 115.5(2) . . ? O7 C8 N1 122.0(2) . . ? O7 C8 C5 126.2(2) . . ? N1 C8 C5 111.7(2) . . ? C10 C9 C7 124.4(2) . . ? C10 C9 H9 117.8 . . ? C7 C9 H9 117.8 . . ? C9 C10 C12 120.1(2) . . ? C9 C10 H10 121.5(19) . . ? C12 C10 H10 118.4(19) . . ? O8 C11 N4 112.5(2) . . ? O8 C11 H11A 109.1 . . ? N4 C11 H11A 109.1 . . ? O8 C11 H11B 109.1 . . ? N4 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? O4 C12 O3 124.2(2) . . ? O4 C12 C10 123.6(3) . . ? O3 C12 C10 112.2(2) . . ? O9 C13 C14 112.5(2) . . ? O9 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? O9 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? O8 C14 C13 107.8(2) . . ? O8 C14 H14A 110.1 . . ? C13 C14 H14A 110.1 . . ? O8 C14 H14B 110.1 . . ? C13 C14 H14B 110.1 . . ? H14A C14 H14B 108.5 . . ? C4 N1 C8 125.5(2) . . ? C4 N1 H1 117.3 . . ? C8 N1 H1 117.3 . . ? C4 N2 H2A 120.0 . . ? C4 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C4 N3 C3 112.4(2) . . ? C6 N4 C3 106.99(19) . . ? C6 N4 C11 126.19(19) . . ? C3 N4 C11 126.69(19) . . ? C6 N5 C5 105.3(2) . . ? C12 O3 H3 109.5 . . ? C7 O6 H6A 109.5 . . ? C11 O8 C14 113.33(19) . . ? C13 O9 H9A 109.5 . . ? O2 C1 O1 123.3(2) . . ? O2 C1 C2 123.4(2) . . ? O1 C1 C2 113.2(2) . . ? C2 C2 C1 122.9(3) 2_655 . ? C2 C2 H2 118.5 2_655 . ? C1 C2 H2 118.5 . . ? C1 O1 H1A 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 N3 C3 C5 N5 179.2(2) . . . . ? N4 C3 C5 N5 -0.8(3) . . . . ? N3 C3 C5 C8 -1.2(4) . . . . ? N4 C3 C5 C8 178.8(2) . . . . ? C3 C5 C8 O7 178.3(2) . . . . ? N5 C5 C8 O7 -2.2(4) . . . . ? C3 C5 C8 N1 -0.6(3) . . . . ? N5 C5 C8 N1 178.9(2) . . . . ? O5 C7 C9 C10 178.2(3) . . . . ? O6 C7 C9 C10 -1.3(4) . . . . ? C7 C9 C10 C12 -177.9(2) . . . . ? C9 C10 C12 O4 -5.5(4) . . . . ? C9 C10 C12 O3 173.8(3) . . . . ? O9 C13 C14 O8 66.8(3) . . . . ? N3 C4 N1 C8 -1.9(4) . . . . ? N2 C4 N1 C8 177.7(2) . . . . ? O7 C8 N1 C4 -176.9(2) . . . . ? C5 C8 N1 C4 2.1(3) . . . . ? N2 C4 N3 C3 -179.5(2) . . . . ? N1 C4 N3 C3 0.0(3) . . . . ? C5 C3 N3 C4 1.5(4) . . . . ? N4 C3 N3 C4 -178.5(2) . . . . ? N5 C6 N4 C3 -0.5(3) . . . . ? N5 C6 N4 C11 175.5(2) . . . . ? N3 C3 N4 C6 -179.2(2) . . . . ? C5 C3 N4 C6 0.8(3) . . . . ? N3 C3 N4 C11 4.8(4) . . . . ? C5 C3 N4 C11 -175.2(2) . . . . ? O8 C11 N4 C6 106.3(3) . . . . ? O8 C11 N4 C3 -78.4(3) . . . . ? N4 C6 N5 C5 0.0(3) . . . . ? C3 C5 N5 C6 0.5(3) . . . . ? C8 C5 N5 C6 -179.0(3) . . . . ? N4 C11 O8 C14 -73.6(2) . . . . ? C13 C14 O8 C11 -177.6(2) . . . . ? O2 C1 C2 C2 -3.9(3) . . . 2_655 ? O1 C1 C2 C2 176.02(13) . . . 2_655 ? 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 O1W H1B O9 0.85 1.99 2.762(3) 149.6 6_566 O1W H1C O9 0.85 1.95 2.768(3) 160.6 2_565 O2W H2C O5 0.85 1.92 2.705(3) 153.6 . O2W H2D O1W 0.85 1.87 2.685(3) 158.7 . N1 H1 O5 0.88 2.08 2.914(3) 158.8 . N2 H2A N3 0.88 2.24 3.113(3) 174.2 2 N2 H2B O2W 0.88 2.09 2.969(3) 177.7 . O3 H3 O2 0.84 1.82 2.659(2) 177.7 6_566 O6 H6A O7 0.84 1.72 2.561(2) 175.5 . O9 H9A O2W 0.84 1.89 2.722(3) 173.7 2 O1 H1A N5 0.84 1.73 2.567(3) 177.2 . _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 65.54 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.800 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 915145'