# 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_xray3382_0m _database_code_depnum_ccdc_archive 'CCDC 889476' #TrackingRef '15746_web_deposit_cif_file_0_JohnR.G.Sander_1354054985.tetrahydrate-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H9 O2 N1, 1.5(C12 H10 N2), 4(O1 H2)' _chemical_formula_sum 'C26 H32 N4 O6' _chemical_formula_weight 496.56 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4243(14) _cell_length_b 12.227(2) _cell_length_c 13.193(2) _cell_angle_alpha 96.960(2) _cell_angle_beta 93.427(2) _cell_angle_gamma 101.280(2) _cell_volume 1318.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8081 _cell_measurement_theta_min 2.4705 _cell_measurement_theta_max 27.5345 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9735 _exptl_absorpt_correction_T_max 0.9911 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 CCD _diffrn_measurement_method 'omega scan' _diffrn_reflns_number 15528 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 27.55 _reflns_number_total 5980 _reflns_number_gt 5020 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Apex2 v2.1-4 (Bruker, 2007)' _computing_cell_refinement 'Apex2 v2.1-4 (Bruker, 2007)' _computing_data_reduction 'Apex2 v2.1-4 (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows v2.01' _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. The oxygen-hydrogen and hydrogen-hydrogen distances for the Water molecules were geometrically constrained. The minor configuration of the bipyridylethene was refined with constrained bond distances, restrained co-planiarity and with ADP fixed to those of the nearest atoms of the major configuration. ; _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^)+(0.1000P)^2^+0.1682P] 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_number_reflns 5980 _refine_ls_number_parameters 402 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.1250 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 0.878 _refine_ls_restrained_S_all 0.879 _refine_ls_shift/su_max 0.005 _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 -0.09119(9) 0.10934(6) -0.06001(6) 0.02268(18) Uani 1 1 d . . . H1O H -0.100(2) 0.1395(14) -0.1203(13) 0.045(4) Uiso 1 1 d . . . O2 O 0.17097(10) 0.59789(6) 0.22113(6) 0.02577(19) Uani 1 1 d . . . N1 N 0.13407(11) 0.42955(7) 0.28282(7) 0.0216(2) Uani 1 1 d . . . H1 H 0.1413 0.3992 0.3380 0.026 Uiso 1 1 calc R A 1 C1 C -0.03240(12) 0.19243(8) 0.01973(8) 0.0182(2) Uani 1 1 d . . . C2 C -0.04334(12) 0.30455(8) 0.01762(8) 0.0194(2) Uani 1 1 d . . . H2 H -0.0886 0.3257 -0.0411 0.023 Uiso 1 1 calc R . . C3 C 0.01288(13) 0.38522(8) 0.10269(8) 0.0200(2) Uani 1 1 d . . . H3 H 0.0047 0.4597 0.1005 0.024 Uiso 1 1 calc R A . C4 C 0.08137(12) 0.35443(8) 0.19097(8) 0.0180(2) Uani 1 1 d . . . C5 C 0.09491(12) 0.24228(8) 0.19199(8) 0.0194(2) Uani 1 1 d . . . H5 H 0.1423 0.2213 0.2501 0.023 Uiso 1 1 calc R A . C6 C 0.03861(12) 0.16220(8) 0.10738(8) 0.0198(2) Uani 1 1 d . . . H6 H 0.0483 0.0880 0.1091 0.024 Uiso 1 1 calc R . . C7 C 0.17408(13) 0.54262(9) 0.29364(8) 0.0223(2) Uani 1 1 d . . . C8 C 0.22451(18) 0.59913(10) 0.40196(9) 0.0347(3) Uani 1 1 d . . . H8A H 0.2026 0.6737 0.4091 0.052 Uiso 1 1 calc R A . H8B H 0.3386 0.6033 0.4171 0.052 Uiso 1 1 calc R . . H8C H 0.1644 0.5563 0.4487 0.052 Uiso 1 1 calc R . . N2 N 0.34125(12) 0.84873(8) 0.58998(7) 0.0271(2) Uani 1 1 d . . . N3 N 0.68653(12) 0.86471(8) 1.28515(7) 0.0260(2) Uani 1 1 d . . . C9 C 0.26380(14) 0.79099(10) 0.65884(9) 0.0268(2) Uani 1 1 d . . . H9 H 0.1629 0.7447 0.6379 0.032 Uiso 1 1 calc R . . C10 C 0.32521(13) 0.79631(10) 0.75932(8) 0.0253(2) Uani 1 1 d . . . H10 H 0.2666 0.7541 0.8039 0.030 Uiso 1 1 calc R . . C11 C 0.47604(13) 0.86569(9) 0.79328(8) 0.0215(2) Uani 1 1 d . . . C12 C 0.55762(13) 0.92479(10) 0.72138(9) 0.0270(2) Uani 1 1 d . . . H12 H 0.6590 0.9714 0.7398 0.032 Uiso 1 1 calc R . . C13 C 0.48666(14) 0.91355(11) 0.62239(9) 0.0301(3) Uani 1 1 d . . . H13 H 0.5435 0.9535 0.5756 0.036 Uiso 1 1 calc R . . C14 C 0.54893(13) 0.88092(9) 0.89926(8) 0.0226(2) Uani 1 1 d . . . H14 H 0.6436 0.9354 0.9164 0.027 Uiso 1 1 calc R . . C15 C 0.76594(14) 0.92118(10) 1.21615(9) 0.0258(2) Uani 1 1 d . . . H15 H 0.8649 0.9695 1.2381 0.031 Uiso 1 1 calc R . . C16 C 0.70958(13) 0.91184(9) 1.11439(8) 0.0242(2) Uani 1 1 d . . . H16 H 0.7692 0.9535 1.0698 0.029 Uiso 1 1 calc R . . C17 C 0.56160(13) 0.83887(9) 1.07906(8) 0.0218(2) Uani 1 1 d . . . C18 C 0.47969(14) 0.77896(10) 1.15058(9) 0.0264(2) Uani 1 1 d . . . H18 H 0.3818 0.7286 1.1307 0.032 Uiso 1 1 calc R . . C19 C 0.54518(14) 0.79507(10) 1.25117(9) 0.0286(3) Uani 1 1 d . . . H19 H 0.4878 0.7553 1.2978 0.034 Uiso 1 1 calc R . . C20 C 0.49041(13) 0.82294(9) 0.97282(8) 0.0232(2) Uani 1 1 d . . . H20 H 0.3966 0.7678 0.9553 0.028 Uiso 1 1 calc R . . N4 N 0.3054(6) 0.4608(5) 0.6526(5) 0.0277(6) Uani 0.766(2) 1 d P A 1 C21 C 0.4362(5) 0.5334(4) 0.7002(3) 0.0293(5) Uani 0.766(2) 1 d P A 1 H21 H 0.5008 0.5793 0.6609 0.035 Uiso 0.766(2) 1 calc PR A 1 C22 C 0.4811(3) 0.5444(2) 0.80425(18) 0.0265(5) Uani 0.766(2) 1 d P A 1 H22 H 0.5735 0.5961 0.8331 0.032 Uiso 0.766(2) 1 calc PR A 1 C23 C 0.3859(2) 0.47672(16) 0.86542(16) 0.0223(4) Uani 0.766(2) 1 d P A 1 C24 C 0.2465(2) 0.40345(19) 0.81691(16) 0.0259(4) Uani 0.766(2) 1 d P A 1 H24 H 0.1764 0.3590 0.8545 0.031 Uiso 0.766(2) 1 calc PR A 1 C25 C 0.2140(5) 0.3979(4) 0.71117(15) 0.0259(5) Uani 0.766(2) 1 d P A 1 H25 H 0.1225 0.3469 0.6798 0.031 Uiso 0.766(2) 1 calc PR A 1 C26 C 0.42761(18) 0.47731(13) 0.97497(11) 0.0257(3) Uani 0.766(2) 1 d P . 1 H26 H 0.3467 0.4433 1.0127 0.031 Uiso 0.766(2) 1 calc PR A 1 N4' N 0.281(2) 0.4574(18) 0.6572(16) 0.0277(6) Uani 0.234(2) 1 d PD A 2 C21' C 0.4153(19) 0.5437(14) 0.6839(10) 0.0293(5) Uani 0.234(2) 1 d PD A 2 H21' H 0.4579 0.5861 0.6342 0.035 Uiso 0.234(2) 1 calc PR A 2 C22' C 0.4861(14) 0.5676(9) 0.7814(7) 0.0265(5) Uani 0.234(2) 1 d PD A 2 H22' H 0.5749 0.6272 0.7970 0.032 Uiso 0.234(2) 1 calc PR A 2 C23' C 0.4309(9) 0.5069(6) 0.8571(7) 0.0223(4) Uani 0.234(2) 1 d PD A 2 C24' C 0.2955(9) 0.4222(8) 0.8322(7) 0.0259(4) Uani 0.234(2) 1 d PD A 2 H24' H 0.2549 0.3789 0.8818 0.031 Uiso 0.234(2) 1 calc PR A 2 C25' C 0.2205(19) 0.4012(15) 0.7355(8) 0.0259(5) Uani 0.234(2) 1 d PD A 2 H25' H 0.1250 0.3469 0.7219 0.031 Uiso 0.234(2) 1 calc PR A 2 C26' C 0.5182(6) 0.5301(4) 0.9618(4) 0.0257(3) Uani 0.234(2) 1 d P . 2 H26' H 0.6048 0.5915 0.9748 0.031 Uiso 0.234(2) 1 calc PR A 2 O3 O 0.178(3) 0.3370(4) 0.4610(7) 0.052(3) Uani 0.48(4) 1 d PD A 1 H3OA H 0.187(4) 0.2680(10) 0.469(2) 0.024(9) Uiso 0.48(4) 1 d PD A 1 H3OB H 0.245(3) 0.3831(16) 0.5090(17) 0.015(8) Uiso 0.48(4) 1 d PD A 1 O3' O 0.252(2) 0.3387(4) 0.4524(3) 0.0388(18) Uani 0.52(4) 1 d PD A 2 H3OC H 0.246(9) 0.269(2) 0.465(5) 0.13(3) Uiso 0.52(4) 1 d PD A 2 H3OD H 0.243(16) 0.380(5) 0.510(4) 0.27(6) Uiso 0.52(4) 1 d PD A 2 O4 O 0.16753(10) 0.12878(7) 0.52212(6) 0.02613(19) Uani 1 1 d D . . H4OA H 0.170(2) 0.0626(10) 0.4867(11) 0.065(6) Uiso 1 1 d D . . H4OB H 0.217(2) 0.1300(14) 0.5831(8) 0.060(5) Uiso 1 1 d D . . O5 O 0.11627(11) 0.80982(7) 0.23395(6) 0.0290(2) Uani 1 1 d D . . H5OA H 0.132(2) 0.8429(11) 0.2987(8) 0.051(5) Uiso 1 1 d D . . H5OB H 0.1378(19) 0.7425(8) 0.2340(11) 0.045(4) Uiso 1 1 d D . . O6 O 0.15196(10) 0.90688(7) 0.43392(6) 0.02685(19) Uani 1 1 d D . . H6OA H 0.2135(14) 0.8829(12) 0.4808(10) 0.040(4) Uiso 1 1 d D . . H6OB H 0.0507(11) 0.8861(15) 0.4506(13) 0.065(6) Uiso 1 1 d 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 0.0319(4) 0.0157(4) 0.0183(4) 0.0008(3) -0.0027(3) 0.0023(3) O2 0.0376(4) 0.0163(4) 0.0221(4) 0.0043(3) -0.0005(3) 0.0024(3) N1 0.0313(5) 0.0170(4) 0.0155(4) 0.0035(3) -0.0010(3) 0.0024(3) C1 0.0185(5) 0.0169(5) 0.0181(5) 0.0013(4) 0.0018(4) 0.0014(4) C2 0.0218(5) 0.0185(5) 0.0178(5) 0.0048(4) -0.0004(4) 0.0030(4) C3 0.0249(5) 0.0146(5) 0.0210(5) 0.0041(4) 0.0014(4) 0.0043(4) C4 0.0199(5) 0.0162(5) 0.0166(5) 0.0020(4) 0.0015(4) 0.0009(4) C5 0.0217(5) 0.0186(5) 0.0184(5) 0.0061(4) -0.0002(4) 0.0034(4) C6 0.0225(5) 0.0154(5) 0.0225(5) 0.0044(4) 0.0016(4) 0.0048(4) C7 0.0275(5) 0.0185(5) 0.0201(5) 0.0020(4) 0.0004(4) 0.0034(4) C8 0.0584(8) 0.0208(6) 0.0214(6) 0.0006(4) -0.0043(5) 0.0031(5) N2 0.0278(5) 0.0319(5) 0.0223(5) 0.0043(4) 0.0003(4) 0.0081(4) N3 0.0272(5) 0.0284(5) 0.0229(5) 0.0023(4) -0.0016(4) 0.0085(4) C9 0.0240(5) 0.0300(6) 0.0239(6) 0.0016(4) -0.0014(4) 0.0020(4) C10 0.0233(5) 0.0297(6) 0.0217(5) 0.0044(4) 0.0023(4) 0.0018(4) C11 0.0205(5) 0.0231(5) 0.0220(5) 0.0025(4) 0.0011(4) 0.0075(4) C12 0.0200(5) 0.0307(6) 0.0301(6) 0.0091(5) -0.0006(4) 0.0025(4) C13 0.0269(6) 0.0383(7) 0.0274(6) 0.0133(5) 0.0033(4) 0.0064(5) C14 0.0177(5) 0.0243(5) 0.0245(5) 0.0009(4) -0.0014(4) 0.0036(4) C15 0.0234(5) 0.0264(6) 0.0258(6) 0.0010(4) -0.0032(4) 0.0040(4) C16 0.0226(5) 0.0261(5) 0.0232(5) 0.0039(4) 0.0002(4) 0.0035(4) C17 0.0208(5) 0.0235(5) 0.0215(5) 0.0017(4) 0.0002(4) 0.0067(4) C18 0.0216(5) 0.0297(6) 0.0261(6) 0.0038(5) -0.0004(4) 0.0020(4) C19 0.0278(6) 0.0343(6) 0.0241(6) 0.0075(5) 0.0024(4) 0.0051(5) C20 0.0191(5) 0.0256(5) 0.0231(5) 0.0003(4) -0.0015(4) 0.0028(4) N4 0.0303(18) 0.0290(7) 0.0233(8) 0.0014(5) -0.0011(10) 0.0074(11) C21 0.0344(13) 0.0283(11) 0.0249(14) 0.0045(9) 0.0023(9) 0.0052(8) C22 0.0268(6) 0.0288(13) 0.0224(13) 0.0009(7) -0.0014(9) 0.0045(9) C23 0.0226(11) 0.0249(11) 0.0197(7) 0.0009(8) 0.0015(8) 0.0068(8) C24 0.0211(11) 0.0317(10) 0.0227(10) 0.0010(7) 0.0004(8) 0.0025(9) C25 0.0266(7) 0.0316(7) 0.0173(14) -0.0016(13) -0.0017(12) 0.0045(5) C26 0.0248(8) 0.0304(8) 0.0210(7) 0.0016(6) 0.0022(6) 0.0046(6) N4' 0.0303(18) 0.0290(7) 0.0233(8) 0.0014(5) -0.0011(10) 0.0074(11) C21' 0.0344(13) 0.0283(11) 0.0249(14) 0.0045(9) 0.0023(9) 0.0052(8) C22' 0.0268(6) 0.0288(13) 0.0224(13) 0.0009(7) -0.0014(9) 0.0045(9) C23' 0.0226(11) 0.0249(11) 0.0197(7) 0.0009(8) 0.0015(8) 0.0068(8) C24' 0.0211(11) 0.0317(10) 0.0227(10) 0.0010(7) 0.0004(8) 0.0025(9) C25' 0.0266(7) 0.0316(7) 0.0173(14) -0.0016(13) -0.0017(12) 0.0045(5) C26' 0.0248(8) 0.0304(8) 0.0210(7) 0.0016(6) 0.0022(6) 0.0046(6) O3 0.104(9) 0.0230(12) 0.0244(17) 0.0036(10) -0.021(3) 0.006(2) O3' 0.072(5) 0.0248(11) 0.0180(11) 0.0063(8) -0.0050(16) 0.0059(16) O4 0.0331(4) 0.0230(4) 0.0214(4) 0.0029(3) -0.0039(3) 0.0055(3) O5 0.0476(5) 0.0227(4) 0.0184(4) 0.0024(3) -0.0009(3) 0.0126(4) O6 0.0318(4) 0.0300(4) 0.0198(4) 0.0026(3) -0.0010(3) 0.0102(3) _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 C1 1.3660(12) . ? O1 H1O 0.922(18) . ? O2 C7 1.2382(13) . ? N1 C7 1.3452(14) . ? N1 C4 1.4197(13) . ? N1 H1 0.8600 . ? C1 C6 1.3924(14) . ? C1 C2 1.3954(14) . ? C2 C3 1.3936(14) . ? C2 H2 0.9300 . ? C3 C4 1.3935(14) . ? C3 H3 0.9300 . ? C4 C5 1.3997(14) . ? C5 C6 1.3857(14) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.5079(15) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? N2 C13 1.3368(16) . ? N2 C9 1.3400(15) . ? N3 C19 1.3383(15) . ? N3 C15 1.3406(15) . ? C9 C10 1.3831(16) . ? C9 H9 0.9300 . ? C10 C11 1.3976(15) . ? C10 H10 0.9300 . ? C11 C12 1.3943(15) . ? C11 C14 1.4684(15) . ? C12 C13 1.3829(16) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C20 1.3322(16) . ? C14 H14 0.9300 . ? C15 C16 1.3808(15) . ? C15 H15 0.9300 . ? C16 C17 1.4007(15) . ? C16 H16 0.9300 . ? C17 C18 1.3967(16) . ? C17 C20 1.4662(15) . ? C18 C19 1.3823(16) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? N4 C25 1.329(3) . ? N4 C21 1.340(4) . ? C21 C22 1.386(3) . ? C21 H21 0.9300 . ? C22 C23 1.399(2) . ? C22 H22 0.9300 . ? C23 C24 1.397(2) . ? C23 C26 1.466(3) . ? C24 C25 1.396(2) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C26 1.335(3) 2_667 ? C26 H26 0.9300 . ? N4' C25' 1.378(10) . ? N4' C21' 1.384(10) . ? C21' C22' 1.358(9) . ? C21' H21' 0.9300 . ? C22' C23' 1.367(7) . ? C22' H22' 0.9300 . ? C23' C24' 1.376(7) . ? C23' C26' 1.493(10) . ? C24' C25' 1.361(8) . ? C24' H24' 0.9300 . ? C25' H25' 0.9300 . ? C26' C26' 1.334(10) 2_667 ? C26' H26' 0.9300 . ? O3 H3OA 0.880(10) . ? O3 H3OB 0.884(10) . ? O3' H3OC 0.880(10) . ? O3' H3OD 0.881(10) . ? O4 H4OA 0.887(9) . ? O4 H4OB 0.880(9) . ? O5 H5OA 0.890(9) . ? O5 H5OB 0.877(8) . ? O6 H6OA 0.896(8) . ? O6 H6OB 0.890(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1O 110.5(10) . . ? C7 N1 C4 127.58(9) . . ? C7 N1 H1 116.2 . . ? C4 N1 H1 116.2 . . ? O1 C1 C6 117.80(9) . . ? O1 C1 C2 123.02(9) . . ? C6 C1 C2 119.17(9) . . ? C3 C2 C1 120.68(9) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C3 C2 120.06(9) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 119.04(9) . . ? C3 C4 N1 123.91(9) . . ? C5 C4 N1 117.01(9) . . ? C6 C5 C4 120.77(9) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 120.27(9) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O2 C7 N1 123.51(10) . . ? O2 C7 C8 121.46(10) . . ? N1 C7 C8 115.03(9) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C13 N2 C9 116.55(10) . . ? C19 N3 C15 116.75(10) . . ? N2 C9 C10 123.78(10) . . ? N2 C9 H9 118.1 . . ? C10 C9 H9 118.1 . . ? C9 C10 C11 119.44(10) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C12 C11 C10 116.83(10) . . ? C12 C11 C14 119.41(10) . . ? C10 C11 C14 123.75(10) . . ? C13 C12 C11 119.51(10) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? N2 C13 C12 123.88(11) . . ? N2 C13 H13 118.1 . . ? C12 C13 H13 118.1 . . ? C20 C14 C11 125.25(10) . . ? C20 C14 H14 117.4 . . ? C11 C14 H14 117.4 . . ? N3 C15 C16 123.90(10) . . ? N3 C15 H15 118.1 . . ? C16 C15 H15 118.1 . . ? C15 C16 C17 119.21(10) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C18 C17 C16 116.95(10) . . ? C18 C17 C20 119.37(10) . . ? C16 C17 C20 123.68(10) . . ? C19 C18 C17 119.54(10) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? N3 C19 C18 123.64(11) . . ? N3 C19 H19 118.2 . . ? C18 C19 H19 118.2 . . ? C14 C20 C17 125.43(10) . . ? C14 C20 H20 117.3 . . ? C17 C20 H20 117.3 . . ? C25 N4 C21 116.4(5) . . ? N4 C21 C22 124.1(4) . . ? N4 C21 H21 117.9 . . ? C22 C21 H21 117.9 . . ? C21 C22 C23 119.3(3) . . ? C21 C22 H22 120.4 . . ? C23 C22 H22 120.4 . . ? C24 C23 C22 116.9(2) . . ? C24 C23 C26 119.51(18) . . ? C22 C23 C26 123.5(2) . . ? C25 C24 C23 119.0(3) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? N4 C25 C24 124.2(4) . . ? N4 C25 H25 117.9 . . ? C24 C25 H25 117.9 . . ? C26 C26 C23 125.28(19) 2_667 . ? C26 C26 H26 117.4 2_667 . ? C23 C26 H26 117.4 . . ? C25' N4' C21' 116.2(19) . . ? C22' C21' N4' 121.2(17) . . ? C22' C21' H21' 119.4 . . ? N4' C21' H21' 119.4 . . ? C21' C22' C23' 122.1(12) . . ? C21' C22' H22' 119.0 . . ? C23' C22' H22' 119.0 . . ? C22' C23' C24' 117.4(10) . . ? C22' C23' C26' 120.8(7) . . ? C24' C23' C26' 121.8(7) . . ? C25' C24' C23' 120.6(11) . . ? C25' C24' H24' 119.7 . . ? C23' C24' H24' 119.7 . . ? C24' C25' N4' 122.4(16) . . ? C24' C25' H25' 118.8 . . ? N4' C25' H25' 118.8 . . ? C26' C26' C23' 125.2(7) 2_667 . ? C26' C26' H26' 117.4 2_667 . ? C23' C26' H26' 117.4 . . ? H3OA O3 H3OB 107.3(15) . . ? H3OC O3' H3OD 107.8(17) . . ? H4OA O4 H4OB 106.7(12) . . ? H5OA O5 H5OB 106.7(11) . . ? H6OA O6 H6OB 104.8(11) . . ? 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 O1 C1 C2 C3 177.42(9) . . . . ? C6 C1 C2 C3 -1.29(15) . . . . ? C1 C2 C3 C4 0.21(15) . . . . ? C2 C3 C4 C5 1.01(15) . . . . ? C2 C3 C4 N1 -176.63(9) . . . . ? C7 N1 C4 C3 -21.68(17) . . . . ? C7 N1 C4 C5 160.63(10) . . . . ? C3 C4 C5 C6 -1.16(15) . . . . ? N1 C4 C5 C6 176.65(9) . . . . ? C4 C5 C6 C1 0.07(15) . . . . ? O1 C1 C6 C5 -177.63(9) . . . . ? C2 C1 C6 C5 1.15(15) . . . . ? C4 N1 C7 O2 -0.61(18) . . . . ? C4 N1 C7 C8 179.54(10) . . . . ? C13 N2 C9 C10 0.69(18) . . . . ? N2 C9 C10 C11 0.38(18) . . . . ? C9 C10 C11 C12 -1.09(16) . . . . ? C9 C10 C11 C14 177.40(10) . . . . ? C10 C11 C12 C13 0.77(16) . . . . ? C14 C11 C12 C13 -177.79(10) . . . . ? C9 N2 C13 C12 -1.04(18) . . . . ? C11 C12 C13 N2 0.31(19) . . . . ? C12 C11 C14 C20 -174.19(11) . . . . ? C10 C11 C14 C20 7.36(18) . . . . ? C19 N3 C15 C16 0.53(17) . . . . ? N3 C15 C16 C17 -0.55(17) . . . . ? C15 C16 C17 C18 -0.22(16) . . . . ? C15 C16 C17 C20 179.74(10) . . . . ? C16 C17 C18 C19 0.97(16) . . . . ? C20 C17 C18 C19 -179.00(10) . . . . ? C15 N3 C19 C18 0.29(17) . . . . ? C17 C18 C19 N3 -1.06(19) . . . . ? C11 C14 C20 C17 -179.16(10) . . . . ? C18 C17 C20 C14 174.41(11) . . . . ? C16 C17 C20 C14 -5.55(18) . . . . ? C25 N4 C21 C22 1.1(6) . . . . ? N4 C21 C22 C23 -0.2(4) . . . . ? C21 C22 C23 C24 -1.8(3) . . . . ? C21 C22 C23 C26 176.5(2) . . . . ? C22 C23 C24 C25 2.8(4) . . . . ? C26 C23 C24 C25 -175.6(3) . . . . ? C21 N4 C25 C24 0.0(7) . . . . ? C23 C24 C25 N4 -2.0(6) . . . . ? C24 C23 C26 C26 163.9(2) . . . 2_667 ? C22 C23 C26 C26 -14.4(3) . . . 2_667 ? C25' N4' C21' C22' 2.5(18) . . . . ? N4' C21' C22' C23' 1.3(14) . . . . ? C21' C22' C23' C24' -2.4(14) . . . . ? C21' C22' C23' C26' 175.7(9) . . . . ? C22' C23' C24' C25' -0.3(15) . . . . ? C26' C23' C24' C25' -178.5(10) . . . . ? C23' C24' C25' N4' 4(2) . . . . ? C21' N4' C25' C24' -5(2) . . . . ? C22' C23' C26' C26' -174.3(8) . . . 2_667 ? C24' C23' C26' C26' 3.8(12) . . . 2_667 ? 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 N1 H1 O3' 0.86 2.02 2.827(7) 156.7 . N1 H1 O3 0.86 1.91 2.765(6) 174.8 . O1 H1O O5 0.922(18) 1.698(18) 2.6195(11) 177.8(15) 2_565 O5 H5OB O2 0.877(8) 1.833(8) 2.7066(12) 174.1(14) . O5 H5OA O6 0.890(9) 1.844(9) 2.7323(12) 176.3(17) . O6 H6OA N2 0.896(8) 1.882(9) 2.7737(13) 173.0(14) . O4 H4OA O6 0.887(9) 1.921(10) 2.7947(12) 167.9(18) 1_545 O4 H4OB N3 0.880(9) 1.863(9) 2.7426(13) 177.3(17) 2_667 O6 H6OB O4 0.890(9) 1.872(9) 2.7495(13) 168.1(17) 2_566 O3' H3OC O4 0.880(10) 1.97(3) 2.807(5) 159(7) . O3' H3OD N4' 0.881(10) 2.03(4) 2.88(2) 162(11) . O3' H3OD N4 0.881(10) 2.00(5) 2.837(8) 158(12) . O3 H3OA O4 0.880(10) 1.902(15) 2.750(5) 161(3) . O3 H3OB N4' 0.884(10) 2.03(3) 2.82(2) 147(3) . O3 H3OB N4 0.884(10) 2.003(18) 2.819(8) 153(3) . _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.307 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.059 data_xray3817_0m _database_code_depnum_ccdc_archive 'CCDC 889477' #TrackingRef '15747_web_deposit_cif_file_1_JohnR.G.Sander_1354054985.dihydrate_2-Final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H9 O2 N1, 1.5(C12 H10 N2), 2(O1 H2)' _chemical_formula_sum 'C26 H28 N4 O4' _chemical_formula_weight 460.52 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2028(9) _cell_length_b 11.5290(12) _cell_length_c 11.7206(12) _cell_angle_alpha 93.3410(10) _cell_angle_beta 99.5260(10) _cell_angle_gamma 102.8040(10) _cell_volume 1190.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8109 _cell_measurement_theta_min 2.3085 _cell_measurement_theta_max 27.5645 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9740 _exptl_absorpt_correction_T_max 0.9956 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 CCD _diffrn_measurement_method 'omega scan' _diffrn_reflns_number 13902 _diffrn_reflns_av_R_equivalents 0.0154 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.57 _reflns_number_total 5375 _reflns_number_gt 4708 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Apex2 v2.1-4 (Bruker, 2007)' _computing_cell_refinement 'Apex2 v2.1-4 (Bruker, 2007)' _computing_data_reduction 'Apex2 v2.1-4 (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows v2.01' _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^)+(0.1000P)^2^+0.0043P] 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_number_reflns 5375 _refine_ls_number_parameters 324 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.1398 _refine_ls_wR_factor_gt 0.1322 _refine_ls_goodness_of_fit_ref 1.181 _refine_ls_restrained_S_all 1.181 _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 O1 O 0.98934(8) 0.70730(6) 1.75529(6) 0.02195(18) Uani 1 1 d . . . H1O H 1.0244 0.7740 1.7902 0.033 Uiso 1 1 calc R . . O2 O 0.88998(9) 0.90361(6) 1.24352(6) 0.02330(19) Uani 1 1 d . . . N1 N 0.90685(9) 0.71371(7) 1.27329(7) 0.01798(19) Uani 1 1 d . . . H1 H 0.9073 0.6460 1.2385 0.022 Uiso 1 1 calc R . . C1 C 0.96772(11) 0.71621(9) 1.63820(8) 0.0183(2) Uani 1 1 d . . . C2 C 1.00127(12) 0.82400(9) 1.58958(9) 0.0205(2) Uani 1 1 d . . . H2 H 1.0375 0.8951 1.6378 0.025 Uiso 1 1 calc R . . C3 C 0.98108(12) 0.82640(8) 1.46962(8) 0.0204(2) Uani 1 1 d . . . H3 H 1.0048 0.8989 1.4380 0.024 Uiso 1 1 calc R . . C4 C 0.92520(11) 0.72028(9) 1.39645(8) 0.0173(2) Uani 1 1 d . . . C5 C 0.88909(11) 0.61257(9) 1.44554(9) 0.0192(2) Uani 1 1 d . . . H5 H 0.8503 0.5415 1.3976 0.023 Uiso 1 1 calc R . . C6 C 0.91058(11) 0.61072(9) 1.56532(9) 0.0202(2) Uani 1 1 d . . . H6 H 0.8866 0.5384 1.5971 0.024 Uiso 1 1 calc R . . C7 C 0.88887(11) 0.80107(9) 1.20474(8) 0.0184(2) Uani 1 1 d . . . C8 C 0.86523(12) 0.76639(9) 1.07610(9) 0.0232(2) Uani 1 1 d . . . H8A H 0.9462 0.8135 1.0446 0.035 Uiso 1 1 calc R . . H8B H 0.7703 0.7803 1.0391 0.035 Uiso 1 1 calc R . . H8C H 0.8641 0.6832 1.0626 0.035 Uiso 1 1 calc R . . N2 N 0.68700(11) 0.40095(8) 0.94802(8) 0.0244(2) Uani 1 1 d . . . N3 N 0.44661(10) 0.25978(8) 0.13008(8) 0.0242(2) Uani 1 1 d . . . C9 C 0.78232(13) 0.38689(10) 0.87584(9) 0.0262(2) Uani 1 1 d . . . H9 H 0.8824 0.3893 0.9083 0.031 Uiso 1 1 calc R . . C10 C 0.74049(12) 0.36903(10) 0.75632(9) 0.0227(2) Uani 1 1 d . . . H10 H 0.8106 0.3578 0.7105 0.027 Uiso 1 1 calc R . . C11 C 0.59199(12) 0.36797(9) 0.70480(9) 0.0195(2) Uani 1 1 d . . . C12 C 0.49333(12) 0.38350(9) 0.77980(9) 0.0224(2) Uani 1 1 d . . . H12 H 0.3936 0.3847 0.7499 0.027 Uiso 1 1 calc R . . C13 C 0.54409(12) 0.39716(9) 0.89875(9) 0.0237(2) Uani 1 1 d . . . H13 H 0.4751 0.4041 0.9470 0.028 Uiso 1 1 calc R . . C14 C 0.53652(11) 0.35166(9) 0.57891(9) 0.0208(2) Uani 1 1 d . . . H14 H 0.4413 0.3655 0.5530 0.025 Uiso 1 1 calc R . . C15 C 0.36968(12) 0.30530(10) 0.20211(9) 0.0249(2) Uani 1 1 d . . . H15 H 0.2789 0.3232 0.1697 0.030 Uiso 1 1 calc R . . C16 C 0.41635(12) 0.32728(9) 0.32119(9) 0.0231(2) Uani 1 1 d . . . H16 H 0.3582 0.3594 0.3666 0.028 Uiso 1 1 calc R . . C17 C 0.55191(11) 0.30075(8) 0.37272(8) 0.0184(2) Uani 1 1 d . . . C18 C 0.63240(12) 0.25377(10) 0.29843(9) 0.0225(2) Uani 1 1 d . . . H18 H 0.7234 0.2347 0.3282 0.027 Uiso 1 1 calc R . . C19 C 0.57645(12) 0.23545(10) 0.17972(9) 0.0243(2) Uani 1 1 d . . . H19 H 0.6327 0.2044 0.1319 0.029 Uiso 1 1 calc R . . C20 C 0.60976(11) 0.31888(9) 0.49831(9) 0.0199(2) Uani 1 1 d . . . H20 H 0.7058 0.3064 0.5238 0.024 Uiso 1 1 calc R . . N4 N 0.67956(11) 1.06092(8) 0.90535(8) 0.0245(2) Uani 1 1 d . . . C21 C 0.74675(12) 1.01959(10) 0.82339(9) 0.0243(2) Uani 1 1 d . . . H21 H 0.8388 0.9995 0.8471 0.029 Uiso 1 1 calc R . . C22 C 0.68703(12) 1.00525(10) 0.70587(9) 0.0230(2) Uani 1 1 d . . . H22 H 0.7391 0.9774 0.6527 0.028 Uiso 1 1 calc R . . C23 C 0.54777(12) 1.03285(9) 0.66758(9) 0.0197(2) Uani 1 1 d . . . C24 C 0.47683(12) 1.07389(9) 0.75310(9) 0.0223(2) Uani 1 1 d . . . H24 H 0.3832 1.0924 0.7323 0.027 Uiso 1 1 calc R . . C25 C 0.54624(13) 1.08694(9) 0.86902(9) 0.0241(2) Uani 1 1 d . . . H25 H 0.4974 1.1153 0.9243 0.029 Uiso 1 1 calc R . . C26 C 0.47343(12) 1.01943(9) 0.54529(9) 0.0215(2) Uani 1 1 d . . . H26 H 0.3805 1.0399 0.5293 0.026 Uiso 1 1 calc R . . O3 O 0.88479(10) 1.09274(7) 1.11562(7) 0.0276(2) Uani 1 1 d D . . H3A H 0.8122(15) 1.0862(13) 1.0558(10) 0.048(4) Uiso 1 1 d D . . H3B H 0.8771(17) 1.0248(10) 1.1476(12) 0.046(4) Uiso 1 1 d D . . O4 O 0.86629(9) 0.47978(6) 1.16804(7) 0.0263(2) Uani 1 1 d D . . H4A H 0.8004(15) 0.4505(13) 1.1034(10) 0.052(5) Uiso 1 1 d D . . H4B H 0.9083(16) 0.4211(11) 1.1906(12) 0.045(4) Uiso 1 1 d 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 0.0306(4) 0.0201(4) 0.0143(4) 0.0019(3) 0.0017(3) 0.0059(3) O2 0.0323(4) 0.0196(4) 0.0182(4) 0.0015(3) 0.0006(3) 0.0094(3) N1 0.0214(4) 0.0168(4) 0.0148(4) -0.0008(3) 0.0003(3) 0.0055(3) C1 0.0184(5) 0.0222(5) 0.0149(5) 0.0023(4) 0.0013(4) 0.0070(4) C2 0.0249(5) 0.0172(5) 0.0172(5) -0.0004(4) -0.0008(4) 0.0047(4) C3 0.0250(5) 0.0165(5) 0.0174(5) 0.0021(4) -0.0008(4) 0.0034(4) C4 0.0163(4) 0.0200(5) 0.0155(5) 0.0011(4) 0.0002(3) 0.0060(4) C5 0.0204(5) 0.0164(5) 0.0194(5) -0.0012(4) 0.0014(4) 0.0038(4) C6 0.0224(5) 0.0178(5) 0.0198(5) 0.0036(4) 0.0031(4) 0.0037(4) C7 0.0163(5) 0.0207(5) 0.0169(5) 0.0015(4) 0.0002(4) 0.0036(4) C8 0.0276(5) 0.0241(5) 0.0161(5) 0.0010(4) 0.0003(4) 0.0056(4) N2 0.0295(5) 0.0251(5) 0.0164(4) 0.0016(3) 0.0027(4) 0.0028(4) N3 0.0262(5) 0.0276(5) 0.0171(4) 0.0018(4) 0.0028(4) 0.0038(4) C9 0.0226(5) 0.0334(6) 0.0205(5) 0.0045(4) 0.0003(4) 0.0040(4) C10 0.0221(5) 0.0274(5) 0.0184(5) 0.0038(4) 0.0048(4) 0.0045(4) C11 0.0233(5) 0.0182(5) 0.0158(5) 0.0016(4) 0.0033(4) 0.0031(4) C12 0.0206(5) 0.0255(5) 0.0205(5) 0.0011(4) 0.0031(4) 0.0050(4) C13 0.0287(6) 0.0237(5) 0.0185(5) -0.0006(4) 0.0071(4) 0.0042(4) C14 0.0193(5) 0.0242(5) 0.0175(5) 0.0021(4) 0.0007(4) 0.0039(4) C15 0.0251(5) 0.0298(6) 0.0200(5) 0.0021(4) 0.0009(4) 0.0092(4) C16 0.0253(5) 0.0259(5) 0.0193(5) 0.0006(4) 0.0036(4) 0.0096(4) C17 0.0209(5) 0.0166(4) 0.0158(5) 0.0016(4) 0.0028(4) 0.0007(4) C18 0.0190(5) 0.0284(5) 0.0201(5) 0.0020(4) 0.0033(4) 0.0055(4) C19 0.0256(5) 0.0290(5) 0.0190(5) 0.0007(4) 0.0084(4) 0.0050(4) C20 0.0199(5) 0.0200(5) 0.0179(5) 0.0015(4) 0.0003(4) 0.0031(4) N4 0.0312(5) 0.0224(4) 0.0166(4) 0.0012(3) 0.0005(4) 0.0026(4) C21 0.0230(5) 0.0261(5) 0.0216(5) 0.0024(4) -0.0001(4) 0.0040(4) C22 0.0234(5) 0.0251(5) 0.0193(5) 0.0008(4) 0.0043(4) 0.0036(4) C23 0.0239(5) 0.0160(5) 0.0168(5) 0.0015(4) 0.0020(4) 0.0009(4) C24 0.0260(5) 0.0212(5) 0.0194(5) 0.0011(4) 0.0024(4) 0.0064(4) C25 0.0324(6) 0.0213(5) 0.0182(5) 0.0000(4) 0.0057(4) 0.0053(4) C26 0.0217(5) 0.0231(5) 0.0183(5) 0.0012(4) 0.0007(4) 0.0047(4) O3 0.0401(5) 0.0216(4) 0.0171(4) 0.0030(3) -0.0044(3) 0.0054(3) O4 0.0356(4) 0.0193(4) 0.0202(4) -0.0017(3) -0.0046(3) 0.0067(3) _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 C1 1.3670(11) . ? O1 H1O 0.8200 . ? O2 C7 1.2388(12) . ? N1 C7 1.3459(13) . ? N1 C4 1.4208(12) . ? N1 H1 0.8600 . ? C1 C2 1.3911(14) . ? C1 C6 1.3899(14) . ? C2 C3 1.3902(13) . ? C2 H2 0.9300 . ? C3 C4 1.3963(13) . ? C3 H3 0.9300 . ? C4 C5 1.3955(14) . ? C5 C6 1.3871(13) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.5044(13) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? N2 C13 1.3361(15) . ? N2 C9 1.3432(15) . ? N3 C19 1.3351(14) . ? N3 C15 1.3417(14) . ? C9 C10 1.3804(14) . ? C9 H9 0.9300 . ? C10 C11 1.3969(14) . ? C10 H10 0.9300 . ? C11 C12 1.3954(14) . ? C11 C14 1.4658(13) . ? C12 C13 1.3832(14) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C20 1.3310(15) . ? C14 H14 0.9300 . ? C15 C16 1.3816(14) . ? C15 H15 0.9300 . ? C16 C17 1.3985(14) . ? C16 H16 0.9300 . ? C17 C18 1.3916(14) . ? C17 C20 1.4661(13) . ? C18 C19 1.3878(14) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? N4 C25 1.3348(15) . ? N4 C21 1.3439(14) . ? C21 C22 1.3817(14) . ? C21 H21 0.9300 . ? C22 C23 1.3972(15) . ? C22 H22 0.9300 . ? C23 C24 1.3975(14) . ? C23 C26 1.4660(14) . ? C24 C25 1.3866(14) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C26 1.334(2) 2_676 ? C26 H26 0.9300 . ? O3 H3A 0.872(8) . ? O3 H3B 0.882(8) . ? O4 H4A 0.884(8) . ? O4 H4B 0.883(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1O 109.5 . . ? C7 N1 C4 127.55(8) . . ? C7 N1 H1 116.2 . . ? C4 N1 H1 116.2 . . ? O1 C1 C2 123.52(9) . . ? O1 C1 C6 117.27(9) . . ? C2 C1 C6 119.21(9) . . ? C1 C2 C3 120.60(9) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C2 C3 C4 120.17(9) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 119.04(9) . . ? C5 C4 N1 116.92(8) . . ? C3 C4 N1 124.01(9) . . ? C6 C5 C4 120.49(9) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 120.48(9) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? O2 C7 N1 122.97(9) . . ? O2 C7 C8 121.32(9) . . ? N1 C7 C8 115.70(9) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C13 N2 C9 116.64(9) . . ? C19 N3 C15 116.09(9) . . ? N2 C9 C10 123.86(10) . . ? N2 C9 H9 118.1 . . ? C10 C9 H9 118.1 . . ? C9 C10 C11 119.43(10) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C10 C11 C12 116.66(9) . . ? C10 C11 C14 123.84(9) . . ? C12 C11 C14 119.50(9) . . ? C13 C12 C11 119.89(10) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? N2 C13 C12 123.46(10) . . ? N2 C13 H13 118.3 . . ? C12 C13 H13 118.3 . . ? C20 C14 C11 126.05(9) . . ? C20 C14 H14 117.0 . . ? C11 C14 H14 117.0 . . ? N3 C15 C16 124.33(10) . . ? N3 C15 H15 117.8 . . ? C16 C15 H15 117.8 . . ? C15 C16 C17 119.28(9) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C16 C17 C18 116.66(9) . . ? C16 C17 C20 123.42(9) . . ? C18 C17 C20 119.92(9) . . ? C19 C18 C17 119.77(9) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? N3 C19 C18 123.86(10) . . ? N3 C19 H19 118.1 . . ? C18 C19 H19 118.1 . . ? C14 C20 C17 125.55(9) . . ? C14 C20 H20 117.2 . . ? C17 C20 H20 117.2 . . ? C25 N4 C21 116.83(9) . . ? N4 C21 C22 123.79(10) . . ? N4 C21 H21 118.1 . . ? C22 C21 H21 118.1 . . ? C21 C22 C23 119.48(10) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C22 C23 C24 116.64(9) . . ? C22 C23 C26 123.91(9) . . ? C24 C23 C26 119.44(9) . . ? C25 C24 C23 119.88(10) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? N4 C25 C24 123.36(10) . . ? N4 C25 H25 118.3 . . ? C24 C25 H25 118.3 . . ? C26 C26 C23 126.16(12) 2_676 . ? C26 C26 H26 116.9 2_676 . ? C23 C26 H26 116.9 . . ? H3A O3 H3B 110.6(11) . . ? H4A O4 H4B 106.2(11) . . ? 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 O1 C1 C2 C3 177.94(9) . . . . ? C6 C1 C2 C3 -1.33(15) . . . . ? C1 C2 C3 C4 0.66(16) . . . . ? C2 C3 C4 C5 0.50(15) . . . . ? C2 C3 C4 N1 -177.31(9) . . . . ? C7 N1 C4 C5 158.06(9) . . . . ? C7 N1 C4 C3 -24.09(15) . . . . ? C3 C4 C5 C6 -0.99(15) . . . . ? N1 C4 C5 C6 176.98(8) . . . . ? C4 C5 C6 C1 0.32(15) . . . . ? O1 C1 C6 C5 -178.47(9) . . . . ? C2 C1 C6 C5 0.84(15) . . . . ? C4 N1 C7 O2 1.89(16) . . . . ? C4 N1 C7 C8 -177.45(9) . . . . ? C13 N2 C9 C10 -0.08(16) . . . . ? N2 C9 C10 C11 1.62(17) . . . . ? C9 C10 C11 C12 -1.03(15) . . . . ? C9 C10 C11 C14 179.00(9) . . . . ? C10 C11 C12 C13 -0.94(15) . . . . ? C14 C11 C12 C13 179.03(9) . . . . ? C9 N2 C13 C12 -2.06(16) . . . . ? C11 C12 C13 N2 2.61(16) . . . . ? C10 C11 C14 C20 10.37(17) . . . . ? C12 C11 C14 C20 -169.60(10) . . . . ? C19 N3 C15 C16 -0.16(16) . . . . ? N3 C15 C16 C17 -0.31(17) . . . . ? C15 C16 C17 C18 0.43(15) . . . . ? C15 C16 C17 C20 -178.93(9) . . . . ? C16 C17 C18 C19 -0.12(15) . . . . ? C20 C17 C18 C19 179.27(9) . . . . ? C15 N3 C19 C18 0.50(16) . . . . ? C17 C18 C19 N3 -0.37(16) . . . . ? C11 C14 C20 C17 178.82(9) . . . . ? C16 C17 C20 C14 6.41(16) . . . . ? C18 C17 C20 C14 -172.93(10) . . . . ? C25 N4 C21 C22 1.24(16) . . . . ? N4 C21 C22 C23 -1.03(16) . . . . ? C21 C22 C23 C24 -0.10(15) . . . . ? C21 C22 C23 C26 -179.16(9) . . . . ? C22 C23 C24 C25 0.92(14) . . . . ? C26 C23 C24 C25 -179.97(9) . . . . ? C21 N4 C25 C24 -0.34(16) . . . . ? C23 C24 C25 N4 -0.73(16) . . . . ? C22 C23 C26 C26 -0.4(2) . . . 2_676 ? C24 C23 C26 C26 -179.44(13) . . . 2_676 ? 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 O3 0.82 1.79 2.6030(11) 170.7 2_778 N1 H1 O4 0.86 1.97 2.8193(11) 168.0 . O3 H3A N4 0.872(8) 1.937(9) 2.7969(12) 168.3(16) . O3 H3B O2 0.882(8) 1.855(8) 2.7216(10) 167.0(14) . O4 H4A N2 0.884(8) 1.929(9) 2.8022(12) 169.2(16) . O4 H4B O1 0.883(8) 2.003(8) 2.8854(10) 177.8(14) 2_768 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.393 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.042 data_js5_0m _database_code_depnum_ccdc_archive 'CCDC 889478' #TrackingRef '15748_web_deposit_cif_file_2_JohnR.G.Sander_1354054985.other_dihydrate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H9 O2 N1, C12 H10 N2, 2(O1 H2)' _chemical_formula_sum 'C20 H23 N3 O4' _chemical_formula_weight 369.41 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 P21/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 6.5584(5) _cell_length_b 40.426(3) _cell_length_c 7.1631(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.5890(10) _cell_angle_gamma 90.00 _cell_volume 1882.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9490 _cell_measurement_theta_min 3.0235 _cell_measurement_theta_max 27.4725 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9641 _exptl_absorpt_correction_T_max 0.9818 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 CCD _diffrn_measurement_method 'omega scan' _diffrn_reflns_number 21710 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0158 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -52 _diffrn_reflns_limit_k_max 52 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4326 _reflns_number_gt 3838 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Bruker SMART (Bruker 2001)' _computing_cell_refinement 'Bruker saintplus (Bruker 1999)' _computing_data_reduction 'Bruker saintplus (Bruker 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows v2.01' _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^)+(0.1000P)^2^+0.8889P] 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_number_reflns 4326 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1330 _refine_ls_wR_factor_gt 0.1265 _refine_ls_goodness_of_fit_ref 0.878 _refine_ls_restrained_S_all 0.878 _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 0.67189(15) 0.22499(2) 0.35042(14) 0.0251(2) Uani 1 1 d . . . H1O H 0.551(4) 0.2374(5) 0.345(3) 0.054(6) Uiso 1 1 d . . . O2 O 0.18280(14) 0.08550(2) 0.30664(15) 0.0254(2) Uani 1 1 d . . . N1 N 0.53186(16) 0.08905(2) 0.36509(15) 0.0174(2) Uani 1 1 d . . . H1 H 0.6425 0.0775 0.3855 0.021 Uiso 1 1 calc R . . C1 C 0.63074(19) 0.19218(3) 0.36204(17) 0.0189(3) Uani 1 1 d . . . C2 C 0.44230(19) 0.18004(3) 0.40287(18) 0.0197(3) Uani 1 1 d . . . H2 H 0.3409 0.1947 0.4297 0.024 Uiso 1 1 calc R . . C3 C 0.40474(19) 0.14611(3) 0.40379(18) 0.0184(3) Uani 1 1 d . . . H3 H 0.2778 0.1383 0.4287 0.022 Uiso 1 1 calc R . . C4 C 0.55764(18) 0.12388(3) 0.36738(17) 0.0166(2) Uani 1 1 d . . . C5 C 0.74943(19) 0.13613(3) 0.33526(17) 0.0180(3) Uani 1 1 d . . . H5 H 0.8539 0.1215 0.3161 0.022 Uiso 1 1 calc R . . C6 C 0.78518(19) 0.16982(3) 0.33170(18) 0.0195(3) Uani 1 1 d . . . H6 H 0.9130 0.1776 0.3089 0.023 Uiso 1 1 calc R . . C7 C 0.35477(19) 0.07212(3) 0.33471(17) 0.0181(3) Uani 1 1 d . . . C8 C 0.3753(2) 0.03500(3) 0.3397(2) 0.0226(3) Uani 1 1 d . . . H8A H 0.3498 0.0270 0.4606 0.034 Uiso 1 1 calc R . . H8B H 0.5118 0.0289 0.3185 0.034 Uiso 1 1 calc R . . H8C H 0.2773 0.0255 0.2433 0.034 Uiso 1 1 calc R . . N2 N 0.33940(18) 0.26534(3) 0.33468(16) 0.0230(2) Uani 1 1 d . . . N3 N -0.54467(19) 0.44871(3) 0.36212(16) 0.0251(3) Uani 1 1 d . . . C9 C 0.3859(2) 0.29430(3) 0.42219(18) 0.0233(3) Uani 1 1 d . . . H9 H 0.5193 0.2974 0.4817 0.028 Uiso 1 1 calc R . . C10 C 0.2458(2) 0.31974(3) 0.42841(18) 0.0227(3) Uani 1 1 d . . . H10 H 0.2849 0.3392 0.4930 0.027 Uiso 1 1 calc R . . C11 C 0.0447(2) 0.31606(3) 0.33685(17) 0.0206(3) Uani 1 1 d . . . C12 C -0.0042(2) 0.28570(3) 0.24827(19) 0.0229(3) Uani 1 1 d . . . H12 H -0.1363 0.2818 0.1877 0.027 Uiso 1 1 calc R . . C13 C 0.1456(2) 0.26147(3) 0.25150(19) 0.0237(3) Uani 1 1 d . . . H13 H 0.1097 0.2414 0.1926 0.028 Uiso 1 1 calc R . . C14 C -0.1126(2) 0.34208(3) 0.32763(18) 0.0220(3) Uani 1 1 d . . . H14 H -0.2397 0.3375 0.2586 0.026 Uiso 1 1 calc R . . C15 C -0.5952(2) 0.41727(3) 0.31523(19) 0.0252(3) Uani 1 1 d . . . H15 H -0.7318 0.4126 0.2707 0.030 Uiso 1 1 calc R . . C16 C -0.4557(2) 0.39145(3) 0.32944(19) 0.0232(3) Uani 1 1 d . . . H16 H -0.4992 0.3701 0.2957 0.028 Uiso 1 1 calc R . . C17 C -0.2485(2) 0.39762(3) 0.39502(17) 0.0206(3) Uani 1 1 d . . . C18 C -0.1961(2) 0.43013(3) 0.44588(19) 0.0234(3) Uani 1 1 d . . . H18 H -0.0610 0.4355 0.4926 0.028 Uiso 1 1 calc R . . C19 C -0.3463(2) 0.45443(3) 0.42636(19) 0.0251(3) Uani 1 1 d . . . H19 H -0.3074 0.4760 0.4598 0.030 Uiso 1 1 calc R . . C20 C -0.0892(2) 0.37181(3) 0.40966(18) 0.0220(3) Uani 1 1 d . . . H20 H 0.0365 0.3765 0.4809 0.026 Uiso 1 1 calc R . . O3 O 0.88780(14) 0.04710(2) 0.43280(16) 0.0247(2) Uani 1 1 d . . . H3A H 0.986(3) 0.0586(5) 0.392(3) 0.046(6) Uiso 1 1 d . . . H3B H 0.949(6) 0.0377(10) 0.558(6) 0.134(14) Uiso 1 1 d . . . O4 O 0.90806(17) -0.01427(3) 0.25047(16) 0.0303(2) Uani 1 1 d . . . H4A H 0.793(4) -0.0237(6) 0.210(3) 0.053(6) Uiso 1 1 d . . . H4B H 0.890(5) 0.0075(10) 0.304(5) 0.122(13) 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 0.0255(5) 0.0128(4) 0.0354(5) 0.0012(4) -0.0016(4) -0.0014(4) O2 0.0153(4) 0.0190(5) 0.0411(6) 0.0011(4) 0.0005(4) 0.0011(3) N1 0.0149(5) 0.0130(5) 0.0245(5) 0.0001(4) 0.0026(4) 0.0025(4) C1 0.0224(6) 0.0140(6) 0.0189(6) 0.0008(4) -0.0026(5) -0.0006(4) C2 0.0191(6) 0.0162(6) 0.0232(6) -0.0004(5) 0.0005(5) 0.0039(4) C3 0.0166(6) 0.0159(6) 0.0227(6) 0.0011(5) 0.0026(4) 0.0009(4) C4 0.0174(6) 0.0143(6) 0.0178(6) -0.0001(4) 0.0010(4) 0.0001(4) C5 0.0172(6) 0.0175(6) 0.0192(6) -0.0007(4) 0.0028(4) 0.0017(4) C6 0.0175(6) 0.0193(6) 0.0215(6) 0.0005(5) 0.0018(4) -0.0015(5) C7 0.0172(6) 0.0158(6) 0.0213(6) 0.0003(4) 0.0029(4) -0.0003(4) C8 0.0191(6) 0.0151(6) 0.0343(7) -0.0009(5) 0.0064(5) 0.0000(4) N2 0.0294(6) 0.0170(5) 0.0219(6) 0.0020(4) 0.0006(4) 0.0020(4) N3 0.0300(6) 0.0228(6) 0.0222(6) 0.0022(4) 0.0019(5) 0.0034(5) C9 0.0272(7) 0.0200(6) 0.0217(6) 0.0012(5) -0.0007(5) -0.0012(5) C10 0.0305(7) 0.0171(6) 0.0199(6) -0.0017(5) 0.0013(5) -0.0018(5) C11 0.0276(7) 0.0173(6) 0.0172(6) 0.0017(5) 0.0033(5) 0.0005(5) C12 0.0265(7) 0.0189(6) 0.0219(6) 0.0010(5) -0.0015(5) -0.0019(5) C13 0.0316(7) 0.0152(6) 0.0232(6) -0.0008(5) -0.0008(5) -0.0008(5) C14 0.0268(7) 0.0196(6) 0.0192(6) 0.0009(5) 0.0017(5) 0.0011(5) C15 0.0254(7) 0.0259(7) 0.0240(6) 0.0000(5) 0.0026(5) -0.0004(5) C16 0.0291(7) 0.0189(6) 0.0222(6) -0.0015(5) 0.0052(5) -0.0026(5) C17 0.0281(7) 0.0184(6) 0.0157(5) 0.0020(4) 0.0045(5) 0.0014(5) C18 0.0268(7) 0.0200(6) 0.0226(6) 0.0016(5) 0.0002(5) -0.0008(5) C19 0.0337(7) 0.0166(6) 0.0242(6) 0.0008(5) 0.0006(5) 0.0003(5) C20 0.0254(7) 0.0202(6) 0.0206(6) 0.0021(5) 0.0033(5) -0.0003(5) O3 0.0164(4) 0.0204(5) 0.0374(6) 0.0020(4) 0.0035(4) 0.0010(3) O4 0.0278(6) 0.0269(5) 0.0358(6) -0.0002(4) 0.0028(4) -0.0052(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3584(15) . ? O1 H1O 0.93(2) . ? O2 C7 1.2430(15) . ? N1 C7 1.3408(16) . ? N1 C4 1.4182(15) . ? N1 H1 0.8600 . ? C1 C6 1.3956(18) . ? C1 C2 1.3961(18) . ? C2 C3 1.3935(17) . ? C2 H2 0.9300 . ? C3 C4 1.3966(17) . ? C3 H3 0.9300 . ? C4 C5 1.3988(17) . ? C5 C6 1.3830(17) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.5064(17) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? N2 C13 1.3396(18) . ? N2 C9 1.3439(17) . ? N3 C19 1.3414(19) . ? N3 C15 1.3449(18) . ? C9 C10 1.3837(19) . ? C9 H9 0.9300 . ? C10 C11 1.4015(19) . ? C10 H10 0.9300 . ? C11 C12 1.3994(18) . ? C11 C14 1.4686(18) . ? C12 C13 1.3853(19) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C20 1.3375(19) . ? C14 H14 0.9300 . ? C15 C16 1.3826(19) . ? C15 H15 0.9300 . ? C16 C17 1.401(2) . ? C16 H16 0.9300 . ? C17 C18 1.3946(18) . ? C17 C20 1.4704(18) . ? C18 C19 1.3852(19) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? O3 H3A 0.88(2) . ? O3 H3B 1.00(4) . ? O4 H4A 0.86(2) . ? O4 H4B 0.97(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1O 110.5(14) . . ? C7 N1 C4 127.45(10) . . ? C7 N1 H1 116.3 . . ? C4 N1 H1 116.3 . . ? O1 C1 C6 117.94(11) . . ? O1 C1 C2 123.00(11) . . ? C6 C1 C2 119.06(11) . . ? C3 C2 C1 120.59(11) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 120.04(11) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 119.11(11) . . ? C3 C4 N1 123.62(11) . . ? C5 C4 N1 117.26(11) . . ? C6 C5 C4 120.66(11) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 120.43(12) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? O2 C7 N1 123.52(11) . . ? O2 C7 C8 120.89(11) . . ? N1 C7 C8 115.58(11) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C13 N2 C9 116.90(12) . . ? C13 N2 C1 113.82(8) . . ? C9 N2 C1 128.27(9) . . ? C19 N3 C15 116.38(12) . . ? N2 C9 C10 123.51(12) . . ? N2 C9 H9 118.2 . . ? C10 C9 H9 118.2 . . ? C9 C10 C11 119.59(12) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C12 C11 C10 116.77(12) . . ? C12 C11 C14 119.37(12) . . ? C10 C11 C14 123.86(12) . . ? C13 C12 C11 119.54(13) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? N2 C13 C12 123.65(12) . . ? N2 C13 H13 118.2 . . ? C12 C13 H13 118.2 . . ? C20 C14 C11 125.78(13) . . ? C20 C14 H14 117.1 . . ? C11 C14 H14 117.1 . . ? N3 C15 C16 123.80(13) . . ? N3 C15 H15 118.1 . . ? C16 C15 H15 118.1 . . ? C15 C16 C17 119.56(12) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C18 C17 C16 116.76(12) . . ? C18 C17 C20 120.13(12) . . ? C16 C17 C20 123.10(12) . . ? C19 C18 C17 119.62(13) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? N3 C19 C18 123.86(12) . . ? N3 C19 H19 118.1 . . ? C18 C19 H19 118.1 . . ? C14 C20 C17 124.55(13) . . ? C14 C20 H20 117.7 . . ? C17 C20 H20 117.7 . . ? H3A O3 H3B 106(3) . . ? H4A O4 H4B 113(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 O1 C1 C2 C3 176.77(12) . . . . ? C6 C1 C2 C3 -3.30(18) . . . . ? C1 C2 C3 C4 1.28(19) . . . . ? C2 C3 C4 C5 1.69(18) . . . . ? C2 C3 C4 N1 -179.81(11) . . . . ? C7 N1 C4 C3 23.6(2) . . . . ? C7 N1 C4 C5 -157.90(12) . . . . ? C3 C4 C5 C6 -2.66(18) . . . . ? N1 C4 C5 C6 178.75(11) . . . . ? C4 C5 C6 C1 0.64(19) . . . . ? O1 C1 C6 C5 -177.73(11) . . . . ? C2 C1 C6 C5 2.33(18) . . . . ? C4 N1 C7 O2 -1.3(2) . . . . ? C4 N1 C7 C8 179.68(11) . . . . ? C13 N2 C9 C10 -0.5(2) . . . . ? N2 C9 C10 C11 -1.2(2) . . . . ? C9 C10 C11 C12 2.10(19) . . . . ? C9 C10 C11 C14 -177.09(12) . . . . ? C10 C11 C12 C13 -1.29(19) . . . . ? C14 C11 C12 C13 177.94(12) . . . . ? C9 N2 C13 C12 1.4(2) . . . . ? C1 N2 C13 C12 170.84(11) . . . . ? C11 C12 C13 N2 -0.5(2) . . . . ? C12 C11 C14 C20 178.06(13) . . . . ? C10 C11 C14 C20 -2.8(2) . . . . ? C19 N3 C15 C16 -0.2(2) . . . . ? N3 C15 C16 C17 -0.4(2) . . . . ? C15 C16 C17 C18 1.08(19) . . . . ? C15 C16 C17 C20 -178.31(12) . . . . ? C16 C17 C18 C19 -1.27(19) . . . . ? C20 C17 C18 C19 178.14(12) . . . . ? C15 N3 C19 C18 0.0(2) . . . . ? C17 C18 C19 N3 0.8(2) . . . . ? C11 C14 C20 C17 178.81(12) . . . . ? C18 C17 C20 C14 -164.58(13) . . . . ? C16 C17 C20 C14 14.8(2) . . . . ? 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 O4 H4B O3 0.97(4) 1.85(4) 2.8148(15) 171(3) . O4 H4A N3 0.86(2) 1.99(2) 2.8395(16) 172(2) 2_545 O3 H3B O4 1.00(4) 1.83(4) 2.8104(15) 166(4) 3_756 O3 H3A O2 0.88(2) 1.85(2) 2.7261(14) 176(2) 1_655 N1 H1 O3 0.86 2.02 2.8743(14) 175.5 . O1 H1O N2 0.93(2) 1.78(2) 2.7135(15) 173(2) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.356 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.042 data_x540t _database_code_depnum_ccdc_archive 'CCDC 889479' #TrackingRef '15749_web_deposit_cif_file_3_JohnR.G.Sander_1354054985.ethanolate-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C8 H9 N1 O2), C12 H10 N2, C2 H5 O1' _chemical_formula_sum 'C30 H34 N4 O5' _chemical_formula_weight 530.61 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.835(3) _cell_length_b 10.724(3) _cell_length_c 15.174(4) _cell_angle_alpha 91.638(4) _cell_angle_beta 100.515(4) _cell_angle_gamma 106.191(4) _cell_volume 1352.6(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1002 _cell_measurement_theta_min 2.670 _cell_measurement_theta_max 27.2805 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 CCD _diffrn_measurement_method 'omega scan' _diffrn_reflns_number 15926 _diffrn_reflns_av_R_equivalents 0.1800 _diffrn_reflns_av_sigmaI/netI 0.1267 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6122 _reflns_number_gt 4978 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Bruker SMART (Bruker 2001)' _computing_cell_refinement 'Bruker saintplus (Bruker 1999)' _computing_data_reduction 'Bruker saintplus (Bruker 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows v2.01' _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^)+(0.0849P)^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_number_reflns 6122 _refine_ls_number_parameters 367 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1757 _refine_ls_wR_factor_gt 0.1653 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 0.51639(13) 1.07005(11) 0.29987(8) 0.0263(3) Uani 1 1 d . . . H1O H 0.431(2) 1.026(2) 0.3286(15) 0.043(6) Uiso 1 1 d . . . O2 O 0.54468(13) 0.52705(11) 0.12423(8) 0.0328(3) Uani 1 1 d . . . N1 N 0.75197(14) 0.71195(12) 0.13611(9) 0.0227(3) Uani 1 1 d . . . H1 H 0.8464 0.7437 0.1247 0.027 Uiso 1 1 calc R . . C1 C 0.57069(16) 0.97923(14) 0.26215(10) 0.0217(3) Uani 1 1 d . . . C2 C 0.51492(16) 0.84669(14) 0.27255(10) 0.0227(3) Uani 1 1 d . . . H2 H 0.4368 0.8176 0.3068 0.027 Uiso 1 1 calc R . . C3 C 0.57419(16) 0.75758(14) 0.23255(10) 0.0219(3) Uani 1 1 d . . . H3 H 0.5375 0.6697 0.2415 0.026 Uiso 1 1 calc R . . C4 C 0.68830(16) 0.79865(14) 0.17906(9) 0.0204(3) Uani 1 1 d . . . C5 C 0.74586(16) 0.93142(14) 0.16952(10) 0.0218(3) Uani 1 1 d . . . H5 H 0.8238 0.9604 0.1351 0.026 Uiso 1 1 calc R . . C6 C 0.68862(16) 1.02049(14) 0.21060(10) 0.0224(3) Uani 1 1 d . . . H6 H 0.7290 1.1088 0.2039 0.027 Uiso 1 1 calc R . . C7 C 0.67946(17) 0.58442(15) 0.11123(10) 0.0241(3) Uani 1 1 d . . . C8 C 0.77160(18) 0.51459(15) 0.06409(11) 0.0277(3) Uani 1 1 d . . . H8A H 0.7986 0.4491 0.1005 0.042 Uiso 1 1 calc R . . H8B H 0.8684 0.5759 0.0545 0.042 Uiso 1 1 calc R . . H8C H 0.7067 0.4741 0.0072 0.042 Uiso 1 1 calc R . . O3 O -0.09364(14) 0.57885(11) 0.32847(9) 0.0313(3) Uani 1 1 d . . . H3O H -0.170(3) 0.517(2) 0.3582(17) 0.060(7) Uiso 1 1 d . . . O4 O 0.14968(12) 0.11514(10) 0.15660(8) 0.0263(3) Uani 1 1 d . . . N2 N 0.26035(14) 0.33384(12) 0.15265(8) 0.0222(3) Uani 1 1 d . . . H2N H 0.3362 0.3898 0.1343 0.027 Uiso 1 1 calc R . . C9 C -0.01438(17) 0.51344(15) 0.28535(10) 0.0229(3) Uani 1 1 d . . . C10 C -0.04833(17) 0.37817(14) 0.27989(10) 0.0238(3) Uani 1 1 d . . . H10 H -0.1301 0.3292 0.3063 0.029 Uiso 1 1 calc R . . C11 C 0.03775(16) 0.31516(14) 0.23573(10) 0.0232(3) Uani 1 1 d . . . H11 H 0.0135 0.2248 0.2329 0.028 Uiso 1 1 calc R . . C12 C 0.16022(16) 0.38724(14) 0.19570(10) 0.0209(3) Uani 1 1 d . . . C13 C 0.19075(16) 0.52226(14) 0.19910(10) 0.0232(3) Uani 1 1 d . . . H13 H 0.2698 0.5712 0.1708 0.028 Uiso 1 1 calc R . . C14 C 0.10608(17) 0.58465(15) 0.24349(11) 0.0253(3) Uani 1 1 d . . . H14 H 0.1295 0.6749 0.2455 0.030 Uiso 1 1 calc R . . C15 C 0.25378(16) 0.20797(14) 0.13629(10) 0.0218(3) Uani 1 1 d . . . C16 C 0.38302(18) 0.18735(15) 0.09070(11) 0.0270(3) Uani 1 1 d . . . H16A H 0.4428 0.1386 0.1271 0.040 Uiso 1 1 calc R . . H16B H 0.4540 0.2703 0.0827 0.040 Uiso 1 1 calc R . . H16C H 0.3349 0.1400 0.0331 0.040 Uiso 1 1 calc R . . N3 N 0.27579(15) 0.95454(13) 0.39135(10) 0.0278(3) Uani 1 1 d . . . N4 N -0.68460(15) 0.57309(12) 0.58864(9) 0.0259(3) Uani 1 1 d . . . C17 C 0.12517(18) 0.94734(15) 0.35000(11) 0.0268(3) Uani 1 1 d . . . H17 H 0.1103 0.9791 0.2937 0.032 Uiso 1 1 calc R . . C18 C -0.00851(17) 0.89551(15) 0.38644(10) 0.0245(3) Uani 1 1 d . . . H18 H -0.1103 0.8922 0.3547 0.029 Uiso 1 1 calc R . . C19 C 0.00980(17) 0.84807(14) 0.47120(10) 0.0210(3) Uani 1 1 d . . . C20 C 0.16591(17) 0.85772(15) 0.51505(11) 0.0255(3) Uani 1 1 d . . . H20 H 0.1849 0.8298 0.5724 0.031 Uiso 1 1 calc R . . C21 C 0.29293(18) 0.90933(15) 0.47231(12) 0.0278(3) Uani 1 1 d . . . H21 H 0.3960 0.9125 0.5019 0.033 Uiso 1 1 calc R . . C22 C -0.12518(17) 0.79101(14) 0.51505(10) 0.0223(3) Uani 1 1 d . . . H22 H -0.1018 0.7797 0.5760 0.027 Uiso 1 1 calc R . . C23 C -0.54214(18) 0.63427(15) 0.64109(11) 0.0270(3) Uani 1 1 d . . . H23 H -0.5333 0.6347 0.7031 0.032 Uiso 1 1 calc R . . C24 C -0.40733(17) 0.69690(15) 0.60798(10) 0.0252(3) Uani 1 1 d . . . H24 H -0.3115 0.7398 0.6472 0.030 Uiso 1 1 calc R . . C25 C -0.41671(16) 0.69504(14) 0.51523(10) 0.0219(3) Uani 1 1 d . . . C26 C -0.56619(17) 0.63268(14) 0.46076(10) 0.0235(3) Uani 1 1 d . . . H26 H -0.5791 0.6307 0.3985 0.028 Uiso 1 1 calc R . . C27 C -0.69465(17) 0.57405(15) 0.49994(11) 0.0251(3) Uani 1 1 d . . . H27 H -0.7932 0.5331 0.4625 0.030 Uiso 1 1 calc R . . C28 C -0.27922(17) 0.75421(14) 0.47367(10) 0.0232(3) Uani 1 1 d . . . H28 H -0.3015 0.7673 0.4129 0.028 Uiso 1 1 calc R . . O5 O 0.06785(14) -0.14974(12) 0.10352(9) 0.0364(3) Uani 1 1 d . . . H5O H 0.108(3) -0.068(3) 0.1241(19) 0.073(8) Uiso 1 1 d . . . C29 C 0.11678(19) -0.16755(17) 0.02081(11) 0.0325(4) Uani 1 1 d . . . H29A H 0.1080 -0.0953 -0.0148 0.039 Uiso 1 1 calc R . . H29B H 0.0444 -0.2467 -0.0125 0.039 Uiso 1 1 calc R . . C30 C 0.2855(2) -0.17626(17) 0.03357(13) 0.0353(4) Uani 1 1 d . . . H30A H 0.3580 -0.0980 0.0663 0.053 Uiso 1 1 calc R . . H30B H 0.3127 -0.1867 -0.0241 0.053 Uiso 1 1 calc R . . H30C H 0.2941 -0.2497 0.0667 0.053 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 0.0305(5) 0.0228(5) 0.0272(6) 0.0022(5) 0.0128(4) 0.0060(4) O2 0.0310(6) 0.0246(6) 0.0380(7) -0.0052(5) 0.0151(5) -0.0039(4) N1 0.0234(6) 0.0211(6) 0.0222(6) 0.0017(5) 0.0089(5) 0.0013(5) C1 0.0234(7) 0.0234(7) 0.0174(7) 0.0006(6) 0.0040(5) 0.0053(5) C2 0.0250(7) 0.0234(7) 0.0182(7) 0.0040(6) 0.0082(5) 0.0019(6) C3 0.0252(7) 0.0196(7) 0.0185(7) 0.0038(6) 0.0059(5) 0.0014(5) C4 0.0232(6) 0.0207(7) 0.0149(7) 0.0010(6) 0.0040(5) 0.0024(5) C5 0.0229(6) 0.0226(7) 0.0177(7) 0.0043(6) 0.0073(5) 0.0007(5) C6 0.0251(7) 0.0195(7) 0.0207(7) 0.0047(6) 0.0066(5) 0.0016(5) C7 0.0288(7) 0.0221(7) 0.0193(7) 0.0015(6) 0.0061(6) 0.0032(6) C8 0.0327(8) 0.0223(7) 0.0270(8) -0.0006(6) 0.0086(6) 0.0049(6) O3 0.0376(6) 0.0220(5) 0.0374(7) 0.0025(5) 0.0212(5) 0.0049(5) O4 0.0296(5) 0.0201(5) 0.0279(6) 0.0035(5) 0.0103(4) 0.0023(4) N2 0.0233(6) 0.0195(6) 0.0224(7) 0.0035(5) 0.0090(5) 0.0009(5) C9 0.0257(7) 0.0229(7) 0.0193(7) 0.0015(6) 0.0065(5) 0.0046(6) C10 0.0253(7) 0.0229(7) 0.0225(8) 0.0053(6) 0.0086(6) 0.0034(6) C11 0.0255(7) 0.0191(7) 0.0234(8) 0.0043(6) 0.0067(6) 0.0026(5) C12 0.0220(6) 0.0215(7) 0.0175(7) 0.0031(6) 0.0043(5) 0.0035(5) C13 0.0244(7) 0.0206(7) 0.0222(7) 0.0049(6) 0.0072(6) 0.0003(5) C14 0.0283(7) 0.0180(7) 0.0276(8) 0.0034(6) 0.0081(6) 0.0018(6) C15 0.0240(7) 0.0211(7) 0.0176(7) 0.0024(6) 0.0033(5) 0.0028(5) C16 0.0307(8) 0.0233(7) 0.0281(8) 0.0030(6) 0.0113(6) 0.0061(6) N3 0.0314(7) 0.0212(6) 0.0328(7) 0.0005(6) 0.0159(5) 0.0049(5) N4 0.0278(6) 0.0225(6) 0.0280(7) 0.0016(6) 0.0117(5) 0.0047(5) C17 0.0361(8) 0.0231(7) 0.0201(7) 0.0010(6) 0.0098(6) 0.0042(6) C18 0.0259(7) 0.0250(7) 0.0209(7) 0.0015(6) 0.0063(6) 0.0034(6) C19 0.0261(7) 0.0169(6) 0.0195(7) 0.0006(5) 0.0088(5) 0.0027(5) C20 0.0284(7) 0.0230(7) 0.0256(8) 0.0068(6) 0.0078(6) 0.0061(6) C21 0.0262(7) 0.0246(7) 0.0344(9) 0.0054(7) 0.0102(6) 0.0072(6) C22 0.0276(7) 0.0204(7) 0.0194(7) 0.0035(6) 0.0079(6) 0.0053(6) C23 0.0298(7) 0.0289(8) 0.0220(8) 0.0000(7) 0.0095(6) 0.0054(6) C24 0.0262(7) 0.0259(7) 0.0213(8) 0.0003(6) 0.0065(6) 0.0032(6) C25 0.0249(7) 0.0178(6) 0.0248(8) 0.0047(6) 0.0088(6) 0.0061(5) C26 0.0296(7) 0.0209(7) 0.0199(7) 0.0040(6) 0.0059(6) 0.0061(6) C27 0.0247(7) 0.0218(7) 0.0283(8) 0.0026(6) 0.0062(6) 0.0051(6) C28 0.0281(7) 0.0229(7) 0.0188(7) 0.0046(6) 0.0081(6) 0.0050(6) O5 0.0419(7) 0.0227(6) 0.0459(8) -0.0014(6) 0.0275(6) -0.0003(5) C29 0.0345(8) 0.0352(9) 0.0241(8) 0.0047(7) 0.0071(6) 0.0029(7) C30 0.0401(9) 0.0294(8) 0.0375(10) -0.0007(8) 0.0128(7) 0.0089(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 C1 1.3547(18) . ? O1 H1O 0.96(2) . ? O2 C7 1.2328(18) . ? O2 O4 4.9077(18) . ? O2 N3 7.184(2) . ? N1 C7 1.3479(19) . ? N1 C4 1.4130(19) . ? N1 H1 0.8600 . ? C1 C2 1.392(2) . ? C1 C6 1.398(2) . ? C2 C3 1.385(2) . ? C2 H2 0.9300 . ? C3 C4 1.393(2) . ? C3 H3 0.9300 . ? C4 C5 1.393(2) . ? C5 C6 1.381(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.502(2) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? O3 C9 1.3510(19) . ? O3 H3O 0.99(3) . ? O4 C15 1.2419(17) . ? O4 O5 2.7841(18) . ? N2 C15 1.3486(19) . ? N2 C12 1.4175(19) . ? N2 H2N 0.8600 . ? C9 C14 1.393(2) . ? C9 C10 1.394(2) . ? C10 C11 1.390(2) . ? C10 H10 0.9300 . ? C11 C12 1.392(2) . ? C11 H11 0.9300 . ? C12 C13 1.394(2) . ? C13 C14 1.378(2) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.501(2) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? N3 C21 1.332(2) . ? N3 C17 1.344(2) . ? N4 C27 1.333(2) . ? N4 C23 1.339(2) . ? C17 C18 1.378(2) . ? C17 H17 0.9300 . ? C18 C19 1.395(2) . ? C18 H18 0.9300 . ? C19 C20 1.392(2) . ? C19 C22 1.465(2) . ? C20 C21 1.388(2) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C28 1.333(2) . ? C22 H22 0.9300 . ? C23 C24 1.383(2) . ? C23 H23 0.9300 . ? C24 C25 1.394(2) . ? C24 H24 0.9300 . ? C25 C26 1.397(2) . ? C25 C28 1.466(2) . ? C26 C27 1.381(2) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? O5 C29 1.424(2) . ? O5 H5O 0.87(3) . ? C29 C30 1.497(2) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1O 108.5(13) . . ? C7 O2 O4 148.73(9) . . ? C7 O2 N3 109.36(9) . . ? O4 O2 N3 98.47(3) . . ? C7 N1 C4 126.49(13) . . ? C7 N1 H1 116.8 . . ? C4 N1 H1 116.8 . . ? O1 C1 C2 123.09(14) . . ? O1 C1 C6 118.49(13) . . ? C2 C1 C6 118.42(14) . . ? C3 C2 C1 120.92(14) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 120.49(13) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C3 C4 C5 118.67(14) . . ? C3 C4 N1 122.89(13) . . ? C5 C4 N1 118.41(13) . . ? C6 C5 C4 120.80(14) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 120.66(13) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? O2 C7 N1 123.12(14) . . ? O2 C7 C8 120.93(13) . . ? N1 C7 C8 115.94(13) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C9 O3 H3O 109.8(14) . . ? C15 O4 O5 130.01(10) . . ? C15 O4 O2 10.72(8) . . ? O5 O4 O2 140.28(4) . . ? C15 N2 C12 129.32(12) . . ? C15 N2 H2N 115.3 . . ? C12 N2 H2N 115.3 . . ? O3 C9 C14 118.37(13) . . ? O3 C9 C10 123.25(14) . . ? C14 C9 C10 118.38(14) . . ? C11 C10 C9 121.23(14) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C12 120.01(13) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C13 118.57(14) . . ? C11 C12 N2 124.76(13) . . ? C13 C12 N2 116.65(13) . . ? C14 C13 C12 121.31(14) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C9 120.44(14) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.8 . . ? O4 C15 N2 123.51(14) . . ? O4 C15 C16 121.77(14) . . ? N2 C15 C16 114.72(13) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C21 N3 C17 116.62(13) . . ? C21 N3 O2 103.28(9) . . ? C17 N3 O2 106.35(9) . . ? C27 N4 C23 117.23(13) . . ? N3 C17 C18 123.65(15) . . ? N3 C17 H17 118.2 . . ? C18 C17 H17 118.2 . . ? C17 C18 C19 119.60(13) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C20 C19 C18 116.94(14) . . ? C20 C19 C22 119.66(14) . . ? C18 C19 C22 123.40(13) . . ? C21 C20 C19 119.35(15) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? N3 C21 C20 123.82(14) . . ? N3 C21 H21 118.1 . . ? C20 C21 H21 118.1 . . ? C28 C22 C19 124.60(14) . . ? C28 C22 H22 117.7 . . ? C19 C22 H22 117.7 . . ? N4 C23 C24 123.53(15) . . ? N4 C23 H23 118.2 . . ? C24 C23 H23 118.2 . . ? C23 C24 C25 119.25(14) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? C24 C25 C26 116.99(13) . . ? C24 C25 C28 123.35(13) . . ? C26 C25 C28 119.65(14) . . ? C27 C26 C25 119.63(15) . . ? C27 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? N4 C27 C26 123.34(14) . . ? N4 C27 H27 118.3 . . ? C26 C27 H27 118.3 . . ? C22 C28 C25 125.92(14) . . ? C22 C28 H28 117.0 . . ? C25 C28 H28 117.0 . . ? C29 O5 O4 109.70(10) . . ? C29 O5 H5O 109.0(18) . . ? O4 O5 H5O 8.8(17) . . ? O5 C29 C30 113.01(14) . . ? O5 C29 H29A 109.0 . . ? C30 C29 H29A 109.0 . . ? O5 C29 H29B 109.0 . . ? C30 C29 H29B 109.0 . . ? H29A C29 H29B 107.8 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 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 O1 C1 C2 C3 179.95(12) . . . . ? C6 C1 C2 C3 -0.3(2) . . . . ? C1 C2 C3 C4 -1.6(2) . . . . ? C2 C3 C4 C5 2.4(2) . . . . ? C2 C3 C4 N1 -179.52(12) . . . . ? C7 N1 C4 C3 26.2(2) . . . . ? C7 N1 C4 C5 -155.74(14) . . . . ? C3 C4 C5 C6 -1.4(2) . . . . ? N1 C4 C5 C6 -179.53(12) . . . . ? C4 C5 C6 C1 -0.5(2) . . . . ? O1 C1 C6 C5 -178.90(12) . . . . ? C2 C1 C6 C5 1.3(2) . . . . ? O4 O2 C7 N1 -158.22(12) . . . . ? N3 O2 C7 N1 -6.70(17) . . . . ? O4 O2 C7 C8 23.1(3) . . . . ? N3 O2 C7 C8 174.59(11) . . . . ? C4 N1 C7 O2 -0.5(2) . . . . ? C4 N1 C7 C8 178.31(13) . . . . ? C7 O2 O4 C15 -44.4(4) . . . . ? N3 O2 O4 C15 162.7(4) . . . . ? C7 O2 O4 O5 -26.2(2) . . . . ? N3 O2 O4 O5 -179.17(7) . . . . ? O3 C9 C10 C11 -179.20(13) . . . . ? C14 C9 C10 C11 1.5(2) . . . . ? C9 C10 C11 C12 -0.2(2) . . . . ? C10 C11 C12 C13 -1.6(2) . . . . ? C10 C11 C12 N2 176.95(13) . . . . ? C15 N2 C12 C11 4.6(2) . . . . ? C15 N2 C12 C13 -176.79(13) . . . . ? C11 C12 C13 C14 2.2(2) . . . . ? N2 C12 C13 C14 -176.56(13) . . . . ? C12 C13 C14 C9 -0.8(2) . . . . ? O3 C9 C14 C13 179.66(13) . . . . ? C10 C9 C14 C13 -1.0(2) . . . . ? O5 O4 C15 N2 166.60(10) . . . . ? O2 O4 C15 N2 -28.5(3) . . . . ? O5 O4 C15 C16 -13.2(2) . . . . ? O2 O4 C15 C16 151.8(5) . . . . ? C12 N2 C15 O4 1.6(2) . . . . ? C12 N2 C15 C16 -178.60(13) . . . . ? C7 O2 N3 C21 -104.84(13) . . . . ? O4 O2 N3 C21 60.67(9) . . . . ? C7 O2 N3 C17 131.86(14) . . . . ? O4 O2 N3 C17 -62.63(10) . . . . ? C21 N3 C17 C18 -0.6(2) . . . . ? O2 N3 C17 C18 113.88(14) . . . . ? N3 C17 C18 C19 0.6(2) . . . . ? C17 C18 C19 C20 0.7(2) . . . . ? C17 C18 C19 C22 -179.80(14) . . . . ? C18 C19 C20 C21 -1.9(2) . . . . ? C22 C19 C20 C21 178.63(14) . . . . ? C17 N3 C21 C20 -0.6(2) . . . . ? O2 N3 C21 C20 -116.85(15) . . . . ? C19 C20 C21 N3 1.9(2) . . . . ? C20 C19 C22 C28 -166.56(15) . . . . ? C18 C19 C22 C28 14.0(2) . . . . ? C27 N4 C23 C24 -0.2(2) . . . . ? N4 C23 C24 C25 -1.4(2) . . . . ? C23 C24 C25 C26 2.2(2) . . . . ? C23 C24 C25 C28 -177.64(13) . . . . ? C24 C25 C26 C27 -1.5(2) . . . . ? C28 C25 C26 C27 178.34(13) . . . . ? C23 N4 C27 C26 1.0(2) . . . . ? C25 C26 C27 N4 -0.1(2) . . . . ? C19 C22 C28 C25 178.99(13) . . . . ? C24 C25 C28 C22 15.4(2) . . . . ? C26 C25 C28 C22 -164.47(15) . . . . ? C15 O4 O5 C29 -22.86(17) . . . . ? O2 O4 O5 C29 -27.19(13) . . . . ? O4 O5 C29 C30 88.45(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 H5O O4 0.87(3) 1.93(3) 2.7841(18) 167(2) . O3 H3O N4 0.99(3) 1.72(3) 2.7040(18) 172(2) 2_466 O1 H1O N3 0.96(2) 1.82(2) 2.7726(18) 175(2) . N2 H2N O2 0.86 2.05 2.8867(17) 165.4 . N1 H1 O5 0.86 2.06 2.9104(18) 170.2 1_665 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.496 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.079