# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Geer, Michael' 'Smith, Mark' 'Shimizu, Linda' _publ_contact_author_name 'Shimizu, Linda' _publ_contact_author_email shimizul@chem.sc.edu _publ_section_title ; A bis-Urea Macrocycle Displaying Two Crystal Morphologies ; # Attachment '- mg01199_Naphcycle crystalstr.cif' data_mg01199m _database_code_depnum_ccdc_archive 'CCDC 813391' #TrackingRef '- mg01199_Naphcycle crystalstr.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H46 N6 O2' _chemical_formula_sum 'C38 H46 N6 O2' _chemical_formula_weight 618.81 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.8432(11) _cell_length_b 18.133(2) _cell_length_c 10.7628(13) _cell_angle_alpha 90.00 _cell_angle_beta 111.470(3) _cell_angle_gamma 90.00 _cell_volume 1606.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 939 _cell_measurement_theta_min 2.323 _cell_measurement_theta_max 20.210 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12794 _diffrn_reflns_av_R_equivalents 0.0976 _diffrn_reflns_av_sigmaI/netI 0.0926 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 23.26 _reflns_number_total 2304 _reflns_number_gt 1370 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART Version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT-Plus Version 6.45 (Bruker, 2001)' _computing_data_reduction 'SAINT-Plus Version 6.45 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics various _computing_publication_material 'SHELXTL Version 6.14 (Bruker, 2000)' _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^)+(0.0101P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2304 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0867 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.0696 _refine_ls_wR_factor_gt 0.0588 _refine_ls_goodness_of_fit_ref 0.806 _refine_ls_restrained_S_all 0.806 _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 C1 C 0.7229(3) 0.32959(13) 0.4405(3) 0.0240(6) Uani 1 1 d . . . C2 C 0.9665(3) 0.39412(14) 0.5924(2) 0.0306(7) Uani 1 1 d . . . H2A H 0.9229 0.4418 0.6091 0.037 Uiso 1 1 calc R . . H2B H 1.0589 0.3805 0.6745 0.037 Uiso 1 1 calc R . . C3 C 0.8856(3) 0.42073(14) 0.3671(2) 0.0288(7) Uani 1 1 d . . . H3A H 0.9188 0.4207 0.2887 0.035 Uiso 1 1 calc R . . H3B H 0.8484 0.4711 0.3768 0.035 Uiso 1 1 calc R . . C4 C 0.6350(3) 0.36155(13) 0.2061(2) 0.0269(7) Uani 1 1 d . . . H4A H 0.5822 0.3127 0.1970 0.032 Uiso 1 1 calc R . . H4B H 0.6967 0.3622 0.1457 0.032 Uiso 1 1 calc R . . C5 C 0.5036(3) 0.41991(13) 0.1598(2) 0.0235(7) Uani 1 1 d . . . C6 C 0.4830(3) 0.47368(13) 0.2409(2) 0.0235(7) Uani 1 1 d . . . H6 H 0.5547 0.4754 0.3316 0.028 Uiso 1 1 calc R . . C7 C 0.3577(3) 0.52702(13) 0.1939(2) 0.0231(7) Uani 1 1 d . . . C8 C 0.3342(3) 0.58315(13) 0.2759(2) 0.0238(7) Uani 1 1 d . . . H8 H 0.4051 0.5855 0.3668 0.029 Uiso 1 1 calc R . . C9 C 0.2127(3) 0.63429(13) 0.2289(2) 0.0222(6) Uani 1 1 d . . . C10 C 0.1060(3) 0.63019(14) 0.0946(2) 0.0269(7) Uani 1 1 d . . . H10 H 0.0208 0.6652 0.0606 0.032 Uiso 1 1 calc R . . C11 C 0.1247(3) 0.57604(14) 0.0132(2) 0.0282(7) Uani 1 1 d . . . H11 H 0.0506 0.5737 -0.0766 0.034 Uiso 1 1 calc R . . C12 C 0.2504(3) 0.52368(13) 0.0586(2) 0.0229(6) Uani 1 1 d . . . C13 C 0.2736(3) 0.46691(14) -0.0226(2) 0.0279(7) Uani 1 1 d . . . H13 H 0.2015 0.4636 -0.1130 0.033 Uiso 1 1 calc R . . C14 C 0.3950(3) 0.41726(14) 0.0244(2) 0.0288(7) Uani 1 1 d . . . H14 H 0.4080 0.3803 -0.0334 0.035 Uiso 1 1 calc R . . C15 C 0.1872(3) 0.69355(13) 0.3191(2) 0.0271(7) Uani 1 1 d . . . H15A H 0.2836 0.7262 0.3502 0.032 Uiso 1 1 calc R . . H15B H 0.0920 0.7240 0.2672 0.032 Uiso 1 1 calc R . . C16 C 1.1412(3) 0.34704(14) 0.4680(2) 0.0266(7) Uani 1 1 d . . . C17 C 1.0617(3) 0.27739(13) 0.3952(3) 0.0396(8) Uani 1 1 d . . . H17A H 0.9883 0.2899 0.3046 0.059 Uiso 1 1 calc R . . H17B H 0.9997 0.2538 0.4434 0.059 Uiso 1 1 calc R . . H17C H 1.1456 0.2434 0.3906 0.059 Uiso 1 1 calc R . . C18 C 1.2650(3) 0.32724(14) 0.6046(2) 0.0405(8) Uani 1 1 d . . . H18A H 1.3072 0.3725 0.6553 0.061 Uiso 1 1 calc R . . H18B H 1.3546 0.2996 0.5938 0.061 Uiso 1 1 calc R . . H18C H 1.2129 0.2969 0.6529 0.061 Uiso 1 1 calc R . . C19 C 1.2336(3) 0.38557(14) 0.3899(2) 0.0417(8) Uani 1 1 d . . . H19A H 1.1573 0.3986 0.3006 0.063 Uiso 1 1 calc R . . H19B H 1.3170 0.3523 0.3822 0.063 Uiso 1 1 calc R . . H19C H 1.2853 0.4304 0.4373 0.063 Uiso 1 1 calc R . . N1 N 0.8391(2) 0.33746(10) 0.56514(19) 0.0246(5) Uani 1 1 d . . . N2 N 0.7489(2) 0.36926(10) 0.34195(19) 0.0229(5) Uani 1 1 d . . . N3 N 1.0250(2) 0.40308(11) 0.48461(19) 0.0238(5) Uani 1 1 d . . . O1 O 0.6068(2) 0.28760(9) 0.41740(16) 0.0322(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0228(17) 0.0209(15) 0.0282(17) -0.0011(14) 0.0092(14) 0.0040(14) C2 0.0266(17) 0.0337(17) 0.0341(17) -0.0068(14) 0.0142(14) -0.0059(14) C3 0.0244(17) 0.0291(16) 0.0328(17) 0.0011(14) 0.0105(14) -0.0004(13) C4 0.0281(17) 0.0276(16) 0.0262(16) -0.0029(13) 0.0114(14) 0.0004(14) C5 0.0234(17) 0.0242(16) 0.0247(16) 0.0004(13) 0.0108(14) -0.0025(13) C6 0.0225(16) 0.0287(16) 0.0188(15) 0.0014(13) 0.0068(13) -0.0005(13) C7 0.0204(16) 0.0250(15) 0.0237(16) 0.0037(13) 0.0077(13) -0.0005(13) C8 0.0224(17) 0.0281(16) 0.0226(15) -0.0002(13) 0.0100(13) -0.0007(13) C9 0.0206(16) 0.0247(15) 0.0240(16) 0.0045(13) 0.0114(13) 0.0002(13) C10 0.0247(17) 0.0287(16) 0.0280(16) 0.0083(14) 0.0103(14) 0.0040(13) C11 0.0261(17) 0.0365(17) 0.0204(15) 0.0032(14) 0.0066(13) -0.0015(14) C12 0.0197(16) 0.0249(16) 0.0242(16) 0.0030(13) 0.0082(13) 0.0010(13) C13 0.0230(17) 0.0364(17) 0.0211(16) -0.0025(14) 0.0041(13) -0.0009(14) C14 0.0288(18) 0.0325(17) 0.0248(17) -0.0051(14) 0.0094(14) -0.0018(14) C15 0.0295(17) 0.0278(16) 0.0254(16) 0.0053(13) 0.0117(14) 0.0031(13) C16 0.0208(16) 0.0299(16) 0.0297(16) 0.0015(14) 0.0099(14) 0.0021(13) C17 0.0328(19) 0.0336(18) 0.053(2) -0.0096(16) 0.0163(16) 0.0066(15) C18 0.0268(18) 0.0418(19) 0.0492(19) 0.0119(16) 0.0095(15) 0.0010(15) C19 0.0294(18) 0.055(2) 0.0454(19) 0.0095(16) 0.0191(16) 0.0076(15) N1 0.0229(13) 0.0281(13) 0.0240(13) -0.0024(11) 0.0099(11) -0.0054(11) N2 0.0202(13) 0.0237(12) 0.0236(13) 0.0010(11) 0.0063(11) -0.0045(10) N3 0.0209(13) 0.0277(13) 0.0252(13) -0.0006(11) 0.0115(11) -0.0001(11) O1 0.0269(12) 0.0322(11) 0.0355(12) 0.0003(9) 0.0093(9) -0.0122(9) _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 C1 O1 1.229(3) . ? C1 N1 1.366(3) . ? C1 N2 1.369(3) . ? C2 N3 1.442(3) . ? C2 N1 1.473(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N3 1.442(3) . ? C3 N2 1.472(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.447(3) . ? C4 C5 1.515(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.365(3) . ? C5 C14 1.422(3) . ? C6 C7 1.417(3) . ? C6 H6 0.9500 . ? C7 C8 1.411(3) . ? C7 C12 1.419(3) . ? C8 C9 1.369(3) . ? C8 H8 0.9500 . ? C9 C10 1.410(3) . ? C9 C15 1.519(3) . ? C10 C11 1.365(3) . ? C10 H10 0.9500 . ? C11 C12 1.407(3) . ? C11 H11 0.9500 . ? C12 C13 1.413(3) . ? C13 C14 1.350(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 N1 1.461(3) 3_666 ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N3 1.502(3) . ? C16 C17 1.517(3) . ? C16 C18 1.520(3) . ? C16 C19 1.538(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N1 C15 1.461(3) 3_666 ? 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 O1 C1 N1 122.4(2) . . ? O1 C1 N2 122.3(2) . . ? N1 C1 N2 115.3(2) . . ? N3 C2 N1 113.0(2) . . ? N3 C2 H2A 109.0 . . ? N1 C2 H2A 109.0 . . ? N3 C2 H2B 109.0 . . ? N1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? N3 C3 N2 113.7(2) . . ? N3 C3 H3A 108.8 . . ? N2 C3 H3A 108.8 . . ? N3 C3 H3B 108.8 . . ? N2 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? N2 C4 C5 115.6(2) . . ? N2 C4 H4A 108.4 . . ? C5 C4 H4A 108.4 . . ? N2 C4 H4B 108.4 . . ? C5 C4 H4B 108.4 . . ? H4A C4 H4B 107.5 . . ? C6 C5 C14 118.8(2) . . ? C6 C5 C4 123.7(2) . . ? C14 C5 C4 117.6(2) . . ? C5 C6 C7 122.0(2) . . ? C5 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? C8 C7 C6 123.0(2) . . ? C8 C7 C12 118.4(2) . . ? C6 C7 C12 118.6(2) . . ? C9 C8 C7 122.2(2) . . ? C9 C8 H8 118.9 . . ? C7 C8 H8 118.9 . . ? C8 C9 C10 118.9(2) . . ? C8 C9 C15 121.5(2) . . ? C10 C9 C15 119.5(2) . . ? C11 C10 C9 120.2(2) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 121.9(2) . . ? C10 C11 H11 119.0 . . ? C12 C11 H11 119.0 . . ? C11 C12 C13 123.5(2) . . ? C11 C12 C7 118.3(2) . . ? C13 C12 C7 118.2(2) . . ? C14 C13 C12 122.0(2) . . ? C14 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? C13 C14 C5 120.5(2) . . ? C13 C14 H14 119.7 . . ? C5 C14 H14 119.7 . . ? N1 C15 C9 112.33(19) 3_666 . ? N1 C15 H15A 109.1 3_666 . ? C9 C15 H15A 109.1 . . ? N1 C15 H15B 109.1 3_666 . ? C9 C15 H15B 109.1 . . ? H15A C15 H15B 107.9 . . ? N3 C16 C17 114.6(2) . . ? N3 C16 C18 109.1(2) . . ? C17 C16 C18 109.7(2) . . ? N3 C16 C19 106.3(2) . . ? C17 C16 C19 109.6(2) . . ? C18 C16 C19 107.3(2) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C1 N1 C15 120.0(2) . 3_666 ? C1 N1 C2 120.9(2) . . ? C15 N1 C2 116.56(19) 3_666 . ? C1 N2 C4 118.7(2) . . ? C1 N2 C3 123.4(2) . . ? C4 N2 C3 117.9(2) . . ? C2 N3 C3 106.75(19) . . ? C2 N3 C16 118.8(2) . . ? C3 N3 C16 116.61(19) . . ? 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 N2 C4 C5 C6 -4.8(4) . . . . ? N2 C4 C5 C14 176.2(2) . . . . ? C14 C5 C6 C7 -0.5(4) . . . . ? C4 C5 C6 C7 -179.5(2) . . . . ? C5 C6 C7 C8 -179.9(2) . . . . ? C5 C6 C7 C12 0.5(4) . . . . ? C6 C7 C8 C9 179.9(2) . . . . ? C12 C7 C8 C9 -0.4(4) . . . . ? C7 C8 C9 C10 0.9(4) . . . . ? C7 C8 C9 C15 178.9(2) . . . . ? C8 C9 C10 C11 -0.2(4) . . . . ? C15 C9 C10 C11 -178.2(2) . . . . ? C9 C10 C11 C12 -1.0(4) . . . . ? C10 C11 C12 C13 -180.0(2) . . . . ? C10 C11 C12 C7 1.4(4) . . . . ? C8 C7 C12 C11 -0.7(4) . . . . ? C6 C7 C12 C11 178.9(2) . . . . ? C8 C7 C12 C13 -179.4(2) . . . . ? C6 C7 C12 C13 0.3(3) . . . . ? C11 C12 C13 C14 -179.6(3) . . . . ? C7 C12 C13 C14 -1.0(4) . . . . ? C12 C13 C14 C5 0.9(4) . . . . ? C6 C5 C14 C13 -0.2(4) . . . . ? C4 C5 C14 C13 178.9(2) . . . . ? C8 C9 C15 N1 -57.3(3) . . . 3_666 ? C10 C9 C15 N1 120.7(2) . . . 3_666 ? O1 C1 N1 C15 -11.7(4) . . . 3_666 ? N2 C1 N1 C15 171.2(2) . . . 3_666 ? O1 C1 N1 C2 -173.2(2) . . . . ? N2 C1 N1 C2 9.7(3) . . . . ? N3 C2 N1 C1 -38.5(3) . . . . ? N3 C2 N1 C15 159.4(2) . . . 3_666 ? O1 C1 N2 C4 0.3(4) . . . . ? N1 C1 N2 C4 177.4(2) . . . . ? O1 C1 N2 C3 179.1(2) . . . . ? N1 C1 N2 C3 -3.7(3) . . . . ? C5 C4 N2 C1 96.5(3) . . . . ? C5 C4 N2 C3 -82.4(3) . . . . ? N3 C3 N2 C1 26.4(3) . . . . ? N3 C3 N2 C4 -154.8(2) . . . . ? N1 C2 N3 C3 57.1(3) . . . . ? N1 C2 N3 C16 -77.3(3) . . . . ? N2 C3 N3 C2 -51.1(3) . . . . ? N2 C3 N3 C16 84.5(3) . . . . ? C17 C16 N3 C2 81.8(3) . . . . ? C18 C16 N3 C2 -41.6(3) . . . . ? C19 C16 N3 C2 -157.0(2) . . . . ? C17 C16 N3 C3 -48.3(3) . . . . ? C18 C16 N3 C3 -171.7(2) . . . . ? C19 C16 N3 C3 72.9(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.139 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.036 # Attachment '- mg2045.cif' data_mg2045m _database_code_depnum_ccdc_archive 'CCDC 813392' #TrackingRef '- mg2045.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H24 N4 O2, C2 H6 O S, 2(H2 O)' _chemical_formula_sum 'C28 H34 N4 O5 S' _chemical_formula_weight 538.65 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 7.1366(4) _cell_length_b 10.9517(6) _cell_length_c 33.5506(18) _cell_angle_alpha 90.00 _cell_angle_beta 94.2780(10) _cell_angle_gamma 90.00 _cell_volume 2614.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2100 _cell_measurement_theta_min 2.435 _cell_measurement_theta_max 23.572 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.171 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26330 _diffrn_reflns_av_R_equivalents 0.1011 _diffrn_reflns_av_sigmaI/netI 0.0885 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 24.36 _reflns_number_total 4293 _reflns_number_gt 2605 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART Version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT-Plus Version 6.45 (Bruker, 2001)' _computing_data_reduction 'SAINT-Plus Version 6.45 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics various _computing_publication_material 'SHELXTL Version 6.14 (Bruker, 2000)' _refine_special_details ; N-H and O-H distances restrained to be similar to those of the same type 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^)+(0.0166P)^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 4293 _refine_ls_number_parameters 375 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0823 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.0748 _refine_ls_wR_factor_gt 0.0655 _refine_ls_goodness_of_fit_ref 0.826 _refine_ls_restrained_S_all 0.826 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3490(4) 0.5424(2) 0.35526(8) 0.0224(6) Uani 1 1 d . . . C2 C 0.3750(4) 0.5825(2) 0.42672(7) 0.0233(7) Uani 1 1 d . . . H2A H 0.2579 0.6298 0.4210 0.028 Uiso 1 1 calc R . . H2B H 0.4619 0.6336 0.4440 0.028 Uiso 1 1 calc R . . C3 C 0.3291(3) 0.4693(2) 0.44968(7) 0.0203(6) Uani 1 1 d . . . C4 C 0.2527(3) 0.4863(2) 0.48688(7) 0.0256(7) Uani 1 1 d . . . H4C H 0.2318 0.5669 0.4961 0.031 Uiso 1 1 calc R . . C5 C 0.2084(3) 0.3892(2) 0.50994(7) 0.0240(7) Uani 1 1 d . . . H5 H 0.1571 0.4029 0.5349 0.029 Uiso 1 1 calc R . . C6 C 0.2383(3) 0.2679(2) 0.49694(7) 0.0203(6) Uani 1 1 d . . . C7 C 0.1958(3) 0.1644(2) 0.51982(7) 0.0251(7) Uani 1 1 d . . . H7 H 0.1473 0.1753 0.5452 0.030 Uiso 1 1 calc R . . C8 C 0.2235(3) 0.0493(2) 0.50605(7) 0.0258(7) Uani 1 1 d . . . H8 H 0.1946 -0.0188 0.5220 0.031 Uiso 1 1 calc R . . C9 C 0.2947(3) 0.0296(2) 0.46819(7) 0.0231(7) Uani 1 1 d . . . C10 C 0.3406(3) 0.1288(2) 0.44588(7) 0.0218(7) Uani 1 1 d . . . H10 H 0.3908 0.1163 0.4208 0.026 Uiso 1 1 calc R . . C11 C 0.3144(3) 0.2498(2) 0.45956(7) 0.0208(6) Uani 1 1 d . . . C12 C 0.3580(3) 0.3537(2) 0.43655(7) 0.0210(6) Uani 1 1 d . . . H12 H 0.4086 0.3421 0.4114 0.025 Uiso 1 1 calc R . . C13 C 0.3172(4) -0.1007(2) 0.45448(7) 0.0259(7) Uani 1 1 d . . . H13B H 0.3940 -0.1455 0.4755 0.031 Uiso 1 1 calc R . . H13A H 0.1916 -0.1395 0.4518 0.031 Uiso 1 1 calc R . . C14 C 0.3013(4) -0.1330(2) 0.38180(8) 0.0242(7) Uani 1 1 d . . . C15 C 0.3208(4) -0.1583(2) 0.30951(7) 0.0280(7) Uani 1 1 d . . . H15B H 0.2001 -0.2019 0.3110 0.034 Uiso 1 1 calc R . . H15A H 0.4045 -0.2114 0.2949 0.034 Uiso 1 1 calc R . . C16 C 0.2848(3) -0.0430(2) 0.28574(7) 0.0231(6) Uani 1 1 d . . . C17 C 0.2002(3) -0.0543(2) 0.24605(7) 0.0261(7) Uani 1 1 d . . . H17 H 0.1679 -0.1332 0.2360 0.031 Uiso 1 1 calc R . . C18 C 0.1646(3) 0.0446(2) 0.22231(7) 0.0246(7) Uani 1 1 d . . . H18 H 0.1070 0.0338 0.1961 0.030 Uiso 1 1 calc R . . C19 C 0.2122(3) 0.1644(2) 0.23611(7) 0.0220(7) Uani 1 1 d . . . C20 C 0.1823(3) 0.2703(2) 0.21251(7) 0.0255(7) Uani 1 1 d . . . H20 H 0.1301 0.2630 0.1857 0.031 Uiso 1 1 calc R . . C21 C 0.2272(3) 0.3825(2) 0.22755(7) 0.0261(7) Uani 1 1 d . . . H21 H 0.2043 0.4526 0.2112 0.031 Uiso 1 1 calc R . . C22 C 0.3076(3) 0.3971(2) 0.26713(7) 0.0204(6) Uani 1 1 d . . . C23 C 0.3434(3) 0.2963(2) 0.29009(7) 0.0213(6) Uani 1 1 d . . . H23 H 0.4012 0.3056 0.3164 0.026 Uiso 1 1 calc R . . C24 C 0.2967(3) 0.1774(2) 0.27577(7) 0.0198(6) Uani 1 1 d . . . C25 C 0.3315(3) 0.0711(2) 0.29969(7) 0.0222(7) Uani 1 1 d . . . H25 H 0.3886 0.0798 0.3260 0.027 Uiso 1 1 calc R . . C26 C 0.3434(4) 0.5254(2) 0.28197(7) 0.0249(7) Uani 1 1 d . . . H26A H 0.4176 0.5685 0.2625 0.030 Uiso 1 1 calc R . . H26B H 0.2211 0.5678 0.2823 0.030 Uiso 1 1 calc R . . N1 N 0.4408(3) 0.5368(2) 0.32121(6) 0.0237(6) Uani 1 1 d D . . H1 H 0.562(2) 0.544(2) 0.3241(7) 0.020(8) Uiso 1 1 d D . . N2 N 0.4593(3) 0.5611(2) 0.38934(6) 0.0226(5) Uani 1 1 d D . . H2 H 0.580(2) 0.578(2) 0.3867(7) 0.031(8) Uiso 1 1 d D . . N3 N 0.4034(3) -0.1142(2) 0.41709(6) 0.0241(6) Uani 1 1 d D . . H3 H 0.526(2) -0.103(2) 0.4155(7) 0.031(8) Uiso 1 1 d D . . N4 N 0.4043(3) -0.1412(2) 0.34963(6) 0.0249(6) Uani 1 1 d D . . H4 H 0.526(2) -0.122(2) 0.3534(7) 0.025(8) Uiso 1 1 d D . . O1 O 0.1760(2) 0.52926(16) 0.35476(5) 0.0269(5) Uani 1 1 d . . . O2 O 0.1276(2) -0.14610(16) 0.37952(5) 0.0317(5) Uani 1 1 d . . . C27 C 0.8596(4) 0.3257(3) 0.42067(8) 0.0454(9) Uani 1 1 d . . . H27A H 0.7538 0.3537 0.4353 0.068 Uiso 1 1 calc R . . H27C H 0.9559 0.3896 0.4212 0.068 Uiso 1 1 calc R . . H27B H 0.9131 0.2515 0.4333 0.068 Uiso 1 1 calc R . . C28 C 0.9962(4) 0.2416(3) 0.35426(8) 0.0414(8) Uani 1 1 d . . . H28C H 1.0471 0.1774 0.3723 0.062 Uiso 1 1 calc R . . H28B H 1.0852 0.3098 0.3544 0.062 Uiso 1 1 calc R . . H28A H 0.9760 0.2088 0.3271 0.062 Uiso 1 1 calc R . . O3 O 0.6552(2) 0.18355(17) 0.37164(5) 0.0356(5) Uani 1 1 d . . . S1 S 0.77995(10) 0.29363(7) 0.37046(2) 0.0326(2) Uani 1 1 d . . . O4 O 0.8663(3) 0.63540(19) 0.38640(6) 0.0339(5) Uani 1 1 d D . . H4A H 0.899(5) 0.7114(18) 0.3880(10) 0.089(10) Uiso 1 1 d D . . H4B H 0.969(3) 0.603(3) 0.3780(9) 0.089(10) Uiso 1 1 d D . . O5 O 0.7710(3) -0.05453(19) 0.38369(6) 0.0391(6) Uani 1 1 d D . . H5A H 0.750(4) 0.0259(17) 0.3825(9) 0.075(8) Uiso 1 1 d D . . H5B H 0.894(3) -0.072(3) 0.3827(9) 0.075(8) 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 C1 0.0322(18) 0.0094(16) 0.0256(17) 0.0007(12) 0.0023(14) -0.0003(13) C2 0.0254(16) 0.0224(17) 0.0215(15) -0.0019(13) -0.0027(13) 0.0022(13) C3 0.0177(15) 0.0214(17) 0.0210(15) 0.0001(13) -0.0039(12) -0.0001(13) C4 0.0307(18) 0.0228(18) 0.0229(16) -0.0074(13) 0.0001(14) 0.0039(14) C5 0.0191(15) 0.0337(19) 0.0193(15) -0.0021(13) 0.0020(12) 0.0038(14) C6 0.0172(15) 0.0233(18) 0.0201(15) -0.0005(13) -0.0017(12) 0.0023(13) C7 0.0210(16) 0.0334(19) 0.0213(16) 0.0000(14) 0.0033(12) 0.0016(14) C8 0.0242(17) 0.0255(18) 0.0279(17) 0.0056(14) 0.0033(13) -0.0020(14) C9 0.0188(16) 0.0263(17) 0.0239(16) -0.0007(13) -0.0007(12) -0.0029(13) C10 0.0199(15) 0.0301(18) 0.0153(15) -0.0021(13) 0.0005(12) 0.0016(14) C11 0.0195(16) 0.0231(17) 0.0191(15) -0.0003(12) -0.0031(12) 0.0015(12) C12 0.0170(15) 0.0288(18) 0.0171(15) -0.0001(13) -0.0002(12) 0.0008(13) C13 0.0289(17) 0.0219(17) 0.0270(16) -0.0014(13) 0.0028(13) -0.0014(14) C14 0.0307(18) 0.0129(16) 0.0284(18) 0.0005(13) -0.0011(15) -0.0009(14) C15 0.0325(18) 0.0266(18) 0.0247(16) -0.0025(13) 0.0005(13) -0.0033(14) C16 0.0218(16) 0.0245(17) 0.0228(16) -0.0009(13) 0.0002(12) -0.0010(13) C17 0.0277(17) 0.0254(18) 0.0253(17) -0.0065(14) 0.0031(13) -0.0027(14) C18 0.0195(16) 0.0361(19) 0.0180(15) -0.0033(14) -0.0001(12) -0.0012(14) C19 0.0161(15) 0.0288(18) 0.0215(16) -0.0052(13) 0.0041(12) -0.0004(13) C20 0.0270(17) 0.0317(19) 0.0176(15) 0.0013(14) -0.0006(12) 0.0041(14) C21 0.0282(17) 0.0275(18) 0.0227(16) 0.0038(13) 0.0037(13) 0.0039(14) C22 0.0188(15) 0.0219(17) 0.0210(16) 0.0038(12) 0.0047(12) 0.0025(12) C23 0.0189(15) 0.0272(17) 0.0180(15) -0.0035(13) 0.0023(12) -0.0007(13) C24 0.0173(15) 0.0240(17) 0.0181(15) -0.0035(12) 0.0018(12) 0.0006(12) C25 0.0215(16) 0.0275(18) 0.0176(15) -0.0026(13) 0.0009(12) -0.0009(13) C26 0.0266(17) 0.0277(17) 0.0206(16) 0.0037(13) 0.0025(13) 0.0009(13) N1 0.0196(15) 0.0268(15) 0.0246(14) -0.0009(11) 0.0002(12) -0.0008(12) N2 0.0220(15) 0.0230(14) 0.0226(13) 0.0001(10) 0.0007(12) -0.0006(12) N3 0.0232(15) 0.0255(15) 0.0239(14) -0.0010(11) 0.0027(12) -0.0031(12) N4 0.0283(16) 0.0249(15) 0.0213(14) 0.0008(11) -0.0004(12) -0.0028(12) O1 0.0220(11) 0.0334(12) 0.0254(11) -0.0018(9) 0.0026(9) -0.0027(9) O2 0.0238(12) 0.0314(12) 0.0395(12) -0.0028(10) 0.0000(9) -0.0038(10) C27 0.0267(18) 0.070(3) 0.0385(19) -0.0185(17) -0.0018(14) -0.0009(17) C28 0.0350(19) 0.048(2) 0.043(2) -0.0050(16) 0.0154(16) -0.0077(16) O3 0.0298(11) 0.0379(13) 0.0392(12) -0.0044(10) 0.0029(9) -0.0091(10) S1 0.0309(4) 0.0347(5) 0.0318(4) -0.0018(4) 0.0004(3) 0.0013(4) O4 0.0363(13) 0.0326(13) 0.0340(13) -0.0024(11) 0.0099(10) -0.0020(11) O5 0.0328(13) 0.0401(14) 0.0447(14) 0.0016(12) 0.0045(11) -0.0056(13) _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 C1 O1 1.242(3) . ? C1 N2 1.354(3) . ? C1 N1 1.360(3) . ? C2 N2 1.450(3) . ? C2 C3 1.509(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C12 1.361(3) . ? C3 C4 1.411(3) . ? C4 C5 1.367(3) . ? C4 H4C 0.9500 . ? C5 C6 1.419(3) . ? C5 H5 0.9500 . ? C6 C7 1.414(3) . ? C6 C11 1.417(3) . ? C7 C8 1.362(3) . ? C7 H7 0.9500 . ? C8 C9 1.420(3) . ? C8 H8 0.9500 . ? C9 C10 1.373(3) . ? C9 C13 1.511(3) . ? C10 C11 1.419(3) . ? C10 H10 0.9500 . ? C11 C12 1.422(3) . ? C12 H12 0.9500 . ? C13 N3 1.446(3) . ? C13 H13B 0.9900 . ? C13 H13A 0.9900 . ? C14 O2 1.244(3) . ? C14 N4 1.354(3) . ? C14 N3 1.359(3) . ? C15 N4 1.443(3) . ? C15 C16 1.505(3) . ? C15 H15B 0.9900 . ? C15 H15A 0.9900 . ? C16 C25 1.367(3) . ? C16 C17 1.426(3) . ? C17 C18 1.357(3) . ? C17 H17 0.9500 . ? C18 C19 1.424(3) . ? C18 H18 0.9500 . ? C19 C20 1.411(3) . ? C19 C24 1.426(3) . ? C20 C21 1.358(3) . ? C20 H20 0.9500 . ? C21 C22 1.416(3) . ? C21 H21 0.9500 . ? C22 C23 1.359(3) . ? C22 C26 1.506(3) . ? C23 C24 1.419(3) . ? C23 H23 0.9500 . ? C24 C25 1.425(3) . ? C25 H25 0.9500 . ? C26 N1 1.447(3) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? N1 H1 0.867(15) . ? N2 H2 0.889(16) . ? N3 H3 0.887(16) . ? N4 H4 0.890(16) . ? C27 S1 1.772(3) . ? C27 H27A 0.9800 . ? C27 H27C 0.9800 . ? C27 H27B 0.9800 . ? C28 S1 1.768(3) . ? C28 H28C 0.9800 . ? C28 H28B 0.9800 . ? C28 H28A 0.9800 . ? O3 S1 1.5010(18) . ? O4 H4A 0.866(18) . ? O4 H4B 0.879(18) . ? O5 H5A 0.894(18) . ? O5 H5B 0.901(17) . ? 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 O1 C1 N2 122.9(2) . . ? O1 C1 N1 121.6(2) . . ? N2 C1 N1 115.5(2) . . ? N2 C2 C3 115.4(2) . . ? N2 C2 H2A 108.4 . . ? C3 C2 H2A 108.4 . . ? N2 C2 H2B 108.4 . . ? C3 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? C12 C3 C4 119.2(2) . . ? C12 C3 C2 123.7(2) . . ? C4 C3 C2 117.1(2) . . ? C5 C4 C3 121.3(2) . . ? C5 C4 H4C 119.4 . . ? C3 C4 H4C 119.4 . . ? C4 C5 C6 120.5(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C11 118.7(2) . . ? C7 C6 C5 122.7(2) . . ? C11 C6 C5 118.6(2) . . ? C8 C7 C6 121.0(2) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 121.0(3) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C10 C9 C8 118.9(2) . . ? C10 C9 C13 123.1(2) . . ? C8 C9 C13 118.0(2) . . ? C9 C10 C11 121.4(2) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C6 C11 C10 119.0(2) . . ? C6 C11 C12 118.9(2) . . ? C10 C11 C12 122.1(2) . . ? C3 C12 C11 121.6(2) . . ? C3 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? N3 C13 C9 115.0(2) . . ? N3 C13 H13B 108.5 . . ? C9 C13 H13B 108.5 . . ? N3 C13 H13A 108.5 . . ? C9 C13 H13A 108.5 . . ? H13B C13 H13A 107.5 . . ? O2 C14 N4 122.7(3) . . ? O2 C14 N3 122.5(3) . . ? N4 C14 N3 114.7(2) . . ? N4 C15 C16 115.3(2) . . ? N4 C15 H15B 108.4 . . ? C16 C15 H15B 108.4 . . ? N4 C15 H15A 108.4 . . ? C16 C15 H15A 108.4 . . ? H15B C15 H15A 107.5 . . ? C25 C16 C17 118.4(3) . . ? C25 C16 C15 123.9(2) . . ? C17 C16 C15 117.7(2) . . ? C18 C17 C16 121.7(3) . . ? C18 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? C17 C18 C19 121.0(2) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C20 C19 C18 123.5(2) . . ? C20 C19 C24 118.5(2) . . ? C18 C19 C24 118.0(2) . . ? C21 C20 C19 120.9(2) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 121.2(3) . . ? C20 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? C23 C22 C21 119.1(2) . . ? C23 C22 C26 123.4(2) . . ? C21 C22 C26 117.5(2) . . ? C22 C23 C24 121.6(2) . . ? C22 C23 H23 119.2 . . ? C24 C23 H23 119.2 . . ? C23 C24 C25 122.1(2) . . ? C23 C24 C19 118.7(2) . . ? C25 C24 C19 119.2(2) . . ? C16 C25 C24 121.7(2) . . ? C16 C25 H25 119.1 . . ? C24 C25 H25 119.1 . . ? N1 C26 C22 116.0(2) . . ? N1 C26 H26A 108.3 . . ? C22 C26 H26A 108.3 . . ? N1 C26 H26B 108.3 . . ? C22 C26 H26B 108.3 . . ? H26A C26 H26B 107.4 . . ? C1 N1 C26 122.6(2) . . ? C1 N1 H1 116.1(15) . . ? C26 N1 H1 121.2(15) . . ? C1 N2 C2 120.2(2) . . ? C1 N2 H2 116.8(16) . . ? C2 N2 H2 121.4(16) . . ? C14 N3 C13 122.4(2) . . ? C14 N3 H3 115.7(16) . . ? C13 N3 H3 121.5(16) . . ? C14 N4 C15 122.8(2) . . ? C14 N4 H4 116.7(15) . . ? C15 N4 H4 119.6(15) . . ? S1 C27 H27A 109.5 . . ? S1 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? S1 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? H27C C27 H27B 109.5 . . ? S1 C28 H28C 109.5 . . ? S1 C28 H28B 109.5 . . ? H28C C28 H28B 109.5 . . ? S1 C28 H28A 109.5 . . ? H28C C28 H28A 109.5 . . ? H28B C28 H28A 109.5 . . ? O3 S1 C28 106.39(12) . . ? O3 S1 C27 106.42(13) . . ? C28 S1 C27 97.51(13) . . ? H4A O4 H4B 100(3) . . ? H5A O5 H5B 112(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C2 C3 C12 -1.8(4) . . . . ? N2 C2 C3 C4 177.9(2) . . . . ? C12 C3 C4 C5 0.3(4) . . . . ? C2 C3 C4 C5 -179.4(2) . . . . ? C3 C4 C5 C6 0.0(4) . . . . ? C4 C5 C6 C7 179.6(2) . . . . ? C4 C5 C6 C11 -0.2(4) . . . . ? C11 C6 C7 C8 -1.4(4) . . . . ? C5 C6 C7 C8 178.9(2) . . . . ? C6 C7 C8 C9 -0.4(4) . . . . ? C7 C8 C9 C10 1.7(4) . . . . ? C7 C8 C9 C13 -178.5(2) . . . . ? C8 C9 C10 C11 -1.3(4) . . . . ? C13 C9 C10 C11 178.9(2) . . . . ? C7 C6 C11 C10 1.7(4) . . . . ? C5 C6 C11 C10 -178.5(2) . . . . ? C7 C6 C11 C12 -179.7(2) . . . . ? C5 C6 C11 C12 0.0(4) . . . . ? C9 C10 C11 C6 -0.4(4) . . . . ? C9 C10 C11 C12 -178.9(2) . . . . ? C4 C3 C12 C11 -0.4(4) . . . . ? C2 C3 C12 C11 179.2(2) . . . . ? C6 C11 C12 C3 0.3(4) . . . . ? C10 C11 C12 C3 178.8(2) . . . . ? C10 C9 C13 N3 4.2(4) . . . . ? C8 C9 C13 N3 -175.6(2) . . . . ? N4 C15 C16 C25 2.1(4) . . . . ? N4 C15 C16 C17 -179.2(2) . . . . ? C25 C16 C17 C18 -0.4(4) . . . . ? C15 C16 C17 C18 -179.2(2) . . . . ? C16 C17 C18 C19 0.6(4) . . . . ? C17 C18 C19 C20 178.6(2) . . . . ? C17 C18 C19 C24 -0.6(4) . . . . ? C18 C19 C20 C21 178.7(2) . . . . ? C24 C19 C20 C21 -2.1(4) . . . . ? C19 C20 C21 C22 0.8(4) . . . . ? C20 C21 C22 C23 1.3(4) . . . . ? C20 C21 C22 C26 -176.9(2) . . . . ? C21 C22 C23 C24 -2.1(4) . . . . ? C26 C22 C23 C24 176.0(2) . . . . ? C22 C23 C24 C25 -179.2(2) . . . . ? C22 C23 C24 C19 0.8(3) . . . . ? C20 C19 C24 C23 1.3(3) . . . . ? C18 C19 C24 C23 -179.4(2) . . . . ? C20 C19 C24 C25 -178.7(2) . . . . ? C18 C19 C24 C25 0.6(3) . . . . ? C17 C16 C25 C24 0.4(4) . . . . ? C15 C16 C25 C24 179.1(2) . . . . ? C23 C24 C25 C16 179.5(2) . . . . ? C19 C24 C25 C16 -0.5(4) . . . . ? C23 C22 C26 N1 7.2(4) . . . . ? C21 C22 C26 N1 -174.7(2) . . . . ? O1 C1 N1 C26 5.2(4) . . . . ? N2 C1 N1 C26 -175.8(2) . . . . ? C22 C26 N1 C1 -90.2(3) . . . . ? O1 C1 N2 C2 -8.1(4) . . . . ? N1 C1 N2 C2 173.0(2) . . . . ? C3 C2 N2 C1 86.8(3) . . . . ? O2 C14 N3 C13 -3.9(4) . . . . ? N4 C14 N3 C13 178.7(2) . . . . ? C9 C13 N3 C14 -98.9(3) . . . . ? O2 C14 N4 C15 4.0(4) . . . . ? N3 C14 N4 C15 -178.6(2) . . . . ? C16 C15 N4 C14 94.0(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 N1 H1 O4 0.867(15) 3.066(19) 3.766(3) 139.3(18) . N2 H2 O4 0.889(16) 2.142(17) 3.025(3) 172(2) . N3 H3 O5 0.887(16) 2.182(18) 3.000(3) 153(2) . N4 H4 O5 0.890(16) 2.093(18) 2.934(3) 157(2) . O4 H4A O2 0.866(18) 2.29(2) 3.053(3) 147(3) 1_665 O4 H4B O1 0.879(18) 1.902(19) 2.777(3) 174(3) 1_655 O5 H5A O3 0.894(18) 1.880(19) 2.756(3) 166(3) . O5 H5B O2 0.901(17) 1.865(19) 2.749(3) 167(3) 1_655 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.36 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.331 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.046 # Attachment '- mg2048.cif' data_mg2048m _database_code_depnum_ccdc_archive 'CCDC 813393' #TrackingRef '- mg2048.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H24 N4 O2, 2(C H4 O)' _chemical_formula_sum 'C28 H32 N4 O4' _chemical_formula_weight 488.58 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9772(4) _cell_length_b 10.5977(6) _cell_length_c 17.1780(9) _cell_angle_alpha 93.9040(10) _cell_angle_beta 90.3930(10) _cell_angle_gamma 104.4030(10) _cell_volume 1227.03(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3418 _cell_measurement_theta_min 2.242 _cell_measurement_theta_max 24.222 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystals desolvate and lose crystallinity within minutes in air ; _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 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12870 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0554 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 24.26 _reflns_number_total 3966 _reflns_number_gt 2696 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART Version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT-Plus Version 6.45 (Bruker, 2001)' _computing_data_reduction 'SAINT-Plus Version 6.45 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics various _computing_publication_material 'SHELXTL Version 6.14 (Bruker, 2000)' _refine_special_details ; Disordered methanol molecules refined with d(C-O) = 1.45(2) angstrom distance restraints. N-H distances restrained to be similar. 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^)+(0.0504P)^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 3966 _refine_ls_number_parameters 343 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1005 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 0.911 _refine_ls_restrained_S_all 0.913 _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 C1 C 0.9341(3) 0.57295(17) 0.22644(11) 0.0275(5) Uani 1 1 d . . . C2 C 0.9252(3) 0.59442(17) 0.08481(10) 0.0268(5) Uani 1 1 d . . . H2A H 0.8762 0.4982 0.0830 0.032 Uiso 1 1 calc R . . H2B H 1.0410 0.6146 0.0507 0.032 Uiso 1 1 calc R . . C3 C 0.7648(3) 0.64990(16) 0.05171(10) 0.0240(4) Uani 1 1 d . . . C4 C 0.7031(3) 0.61353(17) -0.02703(10) 0.0268(5) Uani 1 1 d . . . H4A H 0.7668 0.5585 -0.0576 0.032 Uiso 1 1 calc R . . C5 C 0.5547(3) 0.65558(17) -0.05989(10) 0.0276(5) Uani 1 1 d . . . H5 H 0.5138 0.6277 -0.1125 0.033 Uiso 1 1 calc R . . C6 C 0.4602(3) 0.74035(17) -0.01672(10) 0.0251(4) Uani 1 1 d . . . C7 C 0.3079(3) 0.78846(18) -0.04897(11) 0.0297(5) Uani 1 1 d . . . H7 H 0.2611 0.7601 -0.1009 0.036 Uiso 1 1 calc R . . C8 C 0.2277(3) 0.87448(18) -0.00685(11) 0.0303(5) Uani 1 1 d . . . H8 H 0.1258 0.9057 -0.0299 0.036 Uiso 1 1 calc R . . C9 C 0.2922(3) 0.91883(16) 0.07072(10) 0.0265(5) Uani 1 1 d . . . C10 C 0.4361(3) 0.87060(16) 0.10398(10) 0.0246(4) Uani 1 1 d . . . H10 H 0.4777 0.8979 0.1566 0.030 Uiso 1 1 calc R . . C11 C 0.5240(3) 0.78115(16) 0.06182(10) 0.0239(4) Uani 1 1 d . . . C12 C 0.6764(3) 0.73287(16) 0.09439(10) 0.0246(4) Uani 1 1 d . . . H12 H 0.7183 0.7586 0.1471 0.029 Uiso 1 1 calc R . . C13 C 0.1984(3) 1.01770(17) 0.11258(11) 0.0298(5) Uani 1 1 d D . . H13B H 0.2132 1.0931 0.0802 0.036 Uiso 1 1 calc R . . H13A H 0.0549 0.9776 0.1164 0.036 Uiso 1 1 calc R . . C14 C 0.2057(3) 1.00141(17) 0.25255(11) 0.0271(5) Uani 1 1 d D . . C15 C 0.1982(3) 0.99961(19) 0.39406(11) 0.0391(5) Uani 1 1 d D . . H15A H 0.0572 0.9538 0.3844 0.047 Uiso 1 1 calc R . . H15B H 0.2032 1.0709 0.4350 0.047 Uiso 1 1 calc R . . C16 C 0.3030(3) 0.90469(18) 0.42540(11) 0.0357(5) Uani 1 1 d . . . C17 C 0.2512(3) 0.8605(2) 0.50041(11) 0.0423(6) Uani 1 1 d . . . H17 H 0.1492 0.8884 0.5276 0.051 Uiso 1 1 calc R . . C18 C 0.3447(3) 0.7792(2) 0.53416(12) 0.0420(6) Uani 1 1 d . . . H18 H 0.3076 0.7514 0.5845 0.050 Uiso 1 1 calc R . . C19 C 0.4964(3) 0.73557(19) 0.49519(11) 0.0368(6) Uani 1 1 d . . . C20 C 0.6057(3) 0.6568(2) 0.52997(12) 0.0421(6) Uani 1 1 d . . . H20 H 0.5778 0.6325 0.5817 0.051 Uiso 1 1 calc R . . C21 C 0.7495(3) 0.61571(19) 0.49038(11) 0.0406(6) Uani 1 1 d . . . H21 H 0.8229 0.5650 0.5155 0.049 Uiso 1 1 calc R . . C22 C 0.7922(3) 0.64692(18) 0.41245(11) 0.0340(5) Uani 1 1 d . . . C23 C 0.6928(3) 0.72658(17) 0.37885(11) 0.0335(5) Uani 1 1 d . . . H23 H 0.7240 0.7506 0.3273 0.040 Uiso 1 1 calc R . . C24 C 0.5452(3) 0.77403(18) 0.41856(11) 0.0329(5) Uani 1 1 d . . . C25 C 0.4446(3) 0.85963(18) 0.38591(11) 0.0348(5) Uani 1 1 d . . . H25 H 0.4768 0.8865 0.3349 0.042 Uiso 1 1 calc R . . C26 C 0.9441(3) 0.58928(18) 0.37053(11) 0.0376(6) Uani 1 1 d . . . H26B H 1.0649 0.6067 0.4042 0.045 Uiso 1 1 calc R . . H26A H 0.8914 0.4934 0.3634 0.045 Uiso 1 1 calc R . . N1 N 0.9988(3) 0.63832(16) 0.29545(9) 0.0339(4) Uani 1 1 d . . . H1 H 1.050(3) 0.7212(18) 0.2930(10) 0.034(6) Uiso 1 1 d . . . N2 N 0.9899(2) 0.64160(15) 0.16358(8) 0.0250(4) Uani 1 1 d . . . H2 H 1.042(3) 0.7251(18) 0.1706(10) 0.032(6) Uiso 1 1 d . . . N3 N 0.2772(2) 1.06588(16) 0.19002(9) 0.0309(4) Uani 1 1 d . . . H3 H 0.343(3) 1.1425(19) 0.1949(8) 0.054(7) Uiso 1 1 d D . . N4 N 0.2751(3) 1.05737(16) 0.32323(9) 0.0369(5) Uani 1 1 d . . . H4 H 0.358(3) 1.1288(19) 0.3284(8) 0.073(9) Uiso 1 1 d D . . O1 O 0.83628(19) 0.45657(11) 0.22023(7) 0.0332(4) Uani 1 1 d . . . O2 O 0.08123(18) 0.89459(11) 0.24562(7) 0.0297(3) Uani 1 1 d . . . C1S C 0.3374(7) 0.4353(5) 0.2676(3) 0.0392(13) Uiso 0.542(6) 1 d PD A 1 H1S1 H 0.3700 0.4935 0.3152 0.059 Uiso 0.542(6) 1 calc PR A 1 H1S2 H 0.1961 0.3911 0.2663 0.059 Uiso 0.542(6) 1 calc PR A 1 H1S3 H 0.3682 0.4865 0.2218 0.059 Uiso 0.542(6) 1 calc PR A 1 O1S O 0.4522(6) 0.3393(2) 0.26670(13) 0.0293(9) Uiso 0.542(6) 1 d PD A 1 H1S H 0.5641 0.3825 0.2521 0.044 Uiso 0.542(6) 1 d PR A 1 C2S C 0.3659(8) 0.4804(5) 0.2555(3) 0.0376(15) Uiso 0.458(6) 1 d PD A 2 H2S1 H 0.3324 0.5228 0.3042 0.056 Uiso 0.458(6) 1 calc PR A 2 H2S2 H 0.2764 0.4899 0.2133 0.056 Uiso 0.458(6) 1 calc PR A 2 H2S3 H 0.5028 0.5214 0.2425 0.056 Uiso 0.458(6) 1 calc PR A 2 O2S O 0.3460(8) 0.3462(3) 0.26491(17) 0.0388(12) Uiso 0.458(6) 1 d PD A 2 H2S H 0.2313 0.3089 0.2799 0.058 Uiso 0.458(6) 1 d PR A 2 C3S C 0.8320(9) 0.1516(6) 0.2698(4) 0.0286(18) Uiso 0.485(3) 1 d PD B 3 H3S1 H 0.9243 0.1820 0.2283 0.043 Uiso 0.485(3) 1 calc PR B 3 H3S2 H 0.7795 0.0567 0.2619 0.043 Uiso 0.485(3) 1 calc PR B 3 H3S3 H 0.9015 0.1733 0.3206 0.043 Uiso 0.485(3) 1 calc PR B 3 O3S O 0.6700(4) 0.2149(2) 0.26768(14) 0.0315(9) Uiso 0.485(3) 1 d PD B 3 H3S H 0.7062 0.2944 0.2571 0.047 Uiso 0.485(3) 1 d PR B 3 C4S C 0.8214(10) 0.1397(6) 0.2541(4) 0.041(2) Uiso 0.515(3) 1 d PD B 4 H4S1 H 0.8268 0.0684 0.2868 0.061 Uiso 0.515(3) 1 calc PR B 4 H4S2 H 0.8776 0.1245 0.2032 0.061 Uiso 0.515(3) 1 calc PR B 4 H4S3 H 0.6835 0.1432 0.2468 0.061 Uiso 0.515(3) 1 calc PR B 4 O4S O 0.9345(4) 0.2625(3) 0.29173(15) 0.0423(9) Uiso 0.515(3) 1 d PD B 4 H4S H 0.9047 0.3203 0.2655 0.063 Uiso 0.515(3) 1 d PR B 4 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0258(11) 0.0224(10) 0.0337(11) 0.0031(9) -0.0028(9) 0.0050(9) C2 0.0285(11) 0.0237(10) 0.0272(10) 0.0006(8) 0.0009(9) 0.0047(9) C3 0.0253(11) 0.0187(9) 0.0259(10) 0.0025(8) 0.0015(8) 0.0014(8) C4 0.0316(11) 0.0223(10) 0.0256(10) 0.0016(8) 0.0058(9) 0.0048(9) C5 0.0322(11) 0.0255(10) 0.0215(10) 0.0023(8) -0.0002(9) 0.0003(9) C6 0.0257(11) 0.0224(10) 0.0242(10) 0.0063(8) 0.0014(9) -0.0006(8) C7 0.0323(12) 0.0293(11) 0.0249(10) 0.0066(9) -0.0048(9) 0.0015(9) C8 0.0268(11) 0.0300(11) 0.0343(11) 0.0111(9) -0.0031(9) 0.0054(9) C9 0.0233(11) 0.0219(10) 0.0322(11) 0.0084(8) 0.0012(9) 0.0003(8) C10 0.0255(11) 0.0229(10) 0.0228(10) 0.0021(8) 0.0000(8) 0.0011(8) C11 0.0224(10) 0.0209(10) 0.0260(10) 0.0045(8) 0.0019(8) 0.0000(8) C12 0.0259(11) 0.0233(10) 0.0218(10) 0.0018(8) -0.0008(8) 0.0009(8) C13 0.0270(11) 0.0249(10) 0.0381(12) 0.0066(9) 0.0007(9) 0.0063(9) C14 0.0218(11) 0.0215(10) 0.0390(12) 0.0008(9) 0.0017(9) 0.0078(9) C15 0.0399(13) 0.0345(12) 0.0343(12) -0.0067(10) 0.0024(10) -0.0044(10) C16 0.0368(13) 0.0315(11) 0.0278(11) -0.0048(9) 0.0001(10) -0.0103(10) C17 0.0433(14) 0.0427(13) 0.0287(12) -0.0069(10) 0.0041(10) -0.0095(11) C18 0.0458(14) 0.0424(13) 0.0239(11) -0.0015(10) 0.0025(10) -0.0141(11) C19 0.0435(14) 0.0325(11) 0.0217(11) -0.0003(9) -0.0037(10) -0.0135(10) C20 0.0553(15) 0.0371(13) 0.0220(11) 0.0034(10) -0.0025(11) -0.0111(11) C21 0.0547(15) 0.0304(12) 0.0277(12) 0.0057(9) -0.0133(11) -0.0068(11) C22 0.0430(13) 0.0245(10) 0.0259(11) 0.0018(9) -0.0081(10) -0.0077(10) C23 0.0403(13) 0.0292(11) 0.0222(10) 0.0045(9) -0.0031(10) -0.0085(10) C24 0.0367(12) 0.0291(11) 0.0224(10) -0.0021(9) -0.0030(9) -0.0100(9) C25 0.0363(13) 0.0341(12) 0.0249(11) 0.0011(9) -0.0024(10) -0.0078(10) C26 0.0537(14) 0.0264(11) 0.0285(11) 0.0062(9) -0.0088(10) 0.0011(10) N1 0.0497(11) 0.0191(9) 0.0268(9) 0.0038(7) -0.0046(8) -0.0036(8) N2 0.0289(9) 0.0168(8) 0.0273(9) 0.0030(7) -0.0026(7) 0.0016(7) N3 0.0284(10) 0.0220(9) 0.0391(10) 0.0017(8) 0.0027(8) 0.0003(8) N4 0.0355(11) 0.0289(10) 0.0377(10) -0.0033(8) -0.0002(8) -0.0067(8) O1 0.0402(8) 0.0194(7) 0.0344(8) 0.0026(6) -0.0028(6) -0.0029(6) O2 0.0320(8) 0.0173(7) 0.0369(8) -0.0001(6) -0.0012(6) 0.0014(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.249(2) . ? C1 N1 1.347(2) . ? C1 N2 1.349(2) . ? C2 N2 1.439(2) . ? C2 C3 1.512(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C12 1.371(2) . ? C3 C4 1.415(2) . ? C4 C5 1.358(3) . ? C4 H4A 0.9500 . ? C5 C6 1.415(3) . ? C5 H5 0.9500 . ? C6 C7 1.413(3) . ? C6 C11 1.422(2) . ? C7 C8 1.356(3) . ? C7 H7 0.9500 . ? C8 C9 1.414(2) . ? C8 H8 0.9500 . ? C9 C10 1.372(2) . ? C9 C13 1.513(3) . ? C10 C11 1.414(2) . ? C10 H10 0.9500 . ? C11 C12 1.417(2) . ? C12 H12 0.9500 . ? C13 N3 1.446(2) . ? C13 H13B 0.9900 . ? C13 H13A 0.9900 . ? C14 O2 1.241(2) . ? C14 N3 1.344(2) . ? C14 N4 1.346(2) . ? C15 N4 1.446(2) . ? C15 C16 1.507(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C25 1.366(3) . ? C16 C17 1.419(3) . ? C17 C18 1.359(3) . ? C17 H17 0.9500 . ? C18 C19 1.412(3) . ? C18 H18 0.9500 . ? C19 C20 1.418(3) . ? C19 C24 1.423(3) . ? C20 C21 1.359(3) . ? C20 H20 0.9500 . ? C21 C22 1.417(3) . ? C21 H21 0.9500 . ? C22 C23 1.371(3) . ? C22 C26 1.512(3) . ? C23 C24 1.414(3) . ? C23 H23 0.9500 . ? C24 C25 1.418(3) . ? C25 H25 0.9500 . ? C26 N1 1.442(2) . ? C26 H26B 0.9900 . ? C26 H26A 0.9900 . ? N1 H1 0.866(18) . ? N2 H2 0.869(18) . ? N3 H3 0.825(18) . ? N4 H4 0.828(19) . ? C1S O1S 1.442(5) . ? C1S H1S1 0.9800 . ? C1S H1S2 0.9800 . ? C1S H1S3 0.9800 . ? O1S H1S 0.8500 . ? C2S O2S 1.415(6) . ? C2S H2S1 0.9800 . ? C2S H2S2 0.9800 . ? C2S H2S3 0.9800 . ? O2S H2S 0.8500 . ? C3S O3S 1.452(6) . ? C3S H3S1 0.9800 . ? C3S H3S2 0.9800 . ? C3S H3S3 0.9800 . ? O3S H3S 0.8500 . ? C4S O4S 1.450(6) . ? C4S H4S1 0.9800 . ? C4S H4S2 0.9800 . ? C4S H4S3 0.9800 . ? O4S H4S 0.8500 . ? 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 O1 C1 N1 123.24(17) . . ? O1 C1 N2 122.09(17) . . ? N1 C1 N2 114.62(16) . . ? N2 C2 C3 115.31(15) . . ? N2 C2 H2A 108.4 . . ? C3 C2 H2A 108.4 . . ? N2 C2 H2B 108.4 . . ? C3 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? C12 C3 C4 118.75(17) . . ? C12 C3 C2 123.16(16) . . ? C4 C3 C2 118.09(17) . . ? C5 C4 C3 121.38(18) . . ? C5 C4 H4A 119.3 . . ? C3 C4 H4A 119.3 . . ? C4 C5 C6 120.79(17) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C7 C6 C5 122.69(16) . . ? C7 C6 C11 118.58(18) . . ? C5 C6 C11 118.71(17) . . ? C8 C7 C6 120.89(17) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 121.46(18) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C10 C9 C8 118.65(18) . . ? C10 C9 C13 123.48(16) . . ? C8 C9 C13 117.87(16) . . ? C9 C10 C11 121.53(16) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C10 C11 C12 122.41(16) . . ? C10 C11 C6 118.86(17) . . ? C12 C11 C6 118.71(17) . . ? C3 C12 C11 121.61(16) . . ? C3 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? N3 C13 C9 115.89(15) . . ? N3 C13 H13B 108.3 . . ? C9 C13 H13B 108.3 . . ? N3 C13 H13A 108.3 . . ? C9 C13 H13A 108.3 . . ? H13B C13 H13A 107.4 . . ? O2 C14 N3 121.58(17) . . ? O2 C14 N4 121.22(18) . . ? N3 C14 N4 117.20(16) . . ? N4 C15 C16 116.06(19) . . ? N4 C15 H15A 108.3 . . ? C16 C15 H15A 108.3 . . ? N4 C15 H15B 108.3 . . ? C16 C15 H15B 108.3 . . ? H15A C15 H15B 107.4 . . ? C25 C16 C17 118.5(2) . . ? C25 C16 C15 123.74(18) . . ? C17 C16 C15 117.7(2) . . ? C18 C17 C16 121.3(2) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C17 C18 C19 120.7(2) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C18 C19 C20 122.6(2) . . ? C18 C19 C24 119.0(2) . . ? C20 C19 C24 118.4(2) . . ? C21 C20 C19 121.0(2) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 121.3(2) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C23 C22 C21 118.4(2) . . ? C23 C22 C26 123.53(18) . . ? C21 C22 C26 118.06(19) . . ? C22 C23 C24 122.03(19) . . ? C22 C23 H23 119.0 . . ? C24 C23 H23 119.0 . . ? C23 C24 C25 123.03(18) . . ? C23 C24 C19 118.7(2) . . ? C25 C24 C19 118.3(2) . . ? C16 C25 C24 122.09(19) . . ? C16 C25 H25 119.0 . . ? C24 C25 H25 119.0 . . ? N1 C26 C22 114.95(17) . . ? N1 C26 H26B 108.5 . . ? C22 C26 H26B 108.5 . . ? N1 C26 H26A 108.5 . . ? C22 C26 H26A 108.5 . . ? H26B C26 H26A 107.5 . . ? C1 N1 C26 124.54(16) . . ? C1 N1 H1 114.7(12) . . ? C26 N1 H1 118.7(12) . . ? C1 N2 C2 123.88(15) . . ? C1 N2 H2 118.9(12) . . ? C2 N2 H2 115.3(12) . . ? C14 N3 C13 120.54(16) . . ? C14 N3 H3 121.1(10) . . ? C13 N3 H3 116.2(10) . . ? C14 N4 C15 121.24(16) . . ? C14 N4 H4 121.8(10) . . ? C15 N4 H4 116.8(10) . . ? C1S O1S H1S 101.9 . . ? O2S C2S H2S1 109.5 . . ? O2S C2S H2S2 109.5 . . ? H2S1 C2S H2S2 109.5 . . ? O2S C2S H2S3 109.5 . . ? H2S1 C2S H2S3 109.5 . . ? H2S2 C2S H2S3 109.5 . . ? C2S O2S H2S 111.9 . . ? C3S O3S H3S 113.4 . . ? C4S O4S H4S 104.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C2 C3 C12 -4.1(2) . . . . ? N2 C2 C3 C4 176.25(16) . . . . ? C12 C3 C4 C5 -2.2(3) . . . . ? C2 C3 C4 C5 177.50(16) . . . . ? C3 C4 C5 C6 1.7(3) . . . . ? C4 C5 C6 C7 178.76(16) . . . . ? C4 C5 C6 C11 0.2(3) . . . . ? C5 C6 C7 C8 -176.79(17) . . . . ? C11 C6 C7 C8 1.8(3) . . . . ? C6 C7 C8 C9 -0.3(3) . . . . ? C7 C8 C9 C10 -1.5(3) . . . . ? C7 C8 C9 C13 178.33(16) . . . . ? C8 C9 C10 C11 1.8(3) . . . . ? C13 C9 C10 C11 -178.08(16) . . . . ? C9 C10 C11 C12 178.29(16) . . . . ? C9 C10 C11 C6 -0.3(3) . . . . ? C7 C6 C11 C10 -1.5(2) . . . . ? C5 C6 C11 C10 177.12(15) . . . . ? C7 C6 C11 C12 179.87(15) . . . . ? C5 C6 C11 C12 -1.5(2) . . . . ? C4 C3 C12 C11 0.8(3) . . . . ? C2 C3 C12 C11 -178.86(15) . . . . ? C10 C11 C12 C3 -177.58(16) . . . . ? C6 C11 C12 C3 1.0(2) . . . . ? C10 C9 C13 N3 3.4(3) . . . . ? C8 C9 C13 N3 -176.51(16) . . . . ? N4 C15 C16 C25 -8.7(3) . . . . ? N4 C15 C16 C17 171.00(16) . . . . ? C25 C16 C17 C18 2.5(3) . . . . ? C15 C16 C17 C18 -177.22(17) . . . . ? C16 C17 C18 C19 -0.3(3) . . . . ? C17 C18 C19 C20 176.27(17) . . . . ? C17 C18 C19 C24 -2.4(3) . . . . ? C18 C19 C20 C21 179.41(17) . . . . ? C24 C19 C20 C21 -1.9(3) . . . . ? C19 C20 C21 C22 -1.7(3) . . . . ? C20 C21 C22 C23 3.8(3) . . . . ? C20 C21 C22 C26 -175.63(17) . . . . ? C21 C22 C23 C24 -2.3(3) . . . . ? C26 C22 C23 C24 177.09(16) . . . . ? C22 C23 C24 C25 178.05(16) . . . . ? C22 C23 C24 C19 -1.2(3) . . . . ? C18 C19 C24 C23 -177.96(16) . . . . ? C20 C19 C24 C23 3.3(3) . . . . ? C18 C19 C24 C25 2.7(2) . . . . ? C20 C19 C24 C25 -175.98(16) . . . . ? C17 C16 C25 C24 -2.1(3) . . . . ? C15 C16 C25 C24 177.62(16) . . . . ? C23 C24 C25 C16 -179.77(17) . . . . ? C19 C24 C25 C16 -0.5(3) . . . . ? C23 C22 C26 N1 8.3(3) . . . . ? C21 C22 C26 N1 -172.32(15) . . . . ? O1 C1 N1 C26 -8.1(3) . . . . ? N2 C1 N1 C26 174.43(18) . . . . ? C22 C26 N1 C1 -103.2(2) . . . . ? O1 C1 N2 C2 7.3(3) . . . . ? N1 C1 N2 C2 -175.14(17) . . . . ? C3 C2 N2 C1 102.5(2) . . . . ? O2 C14 N3 C13 5.3(3) . . . . ? N4 C14 N3 C13 -174.90(17) . . . . ? C9 C13 N3 C14 -86.9(2) . . . . ? O2 C14 N4 C15 -4.1(3) . . . . ? N3 C14 N4 C15 176.09(18) . . . . ? C16 C15 N4 C14 90.6(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 N1 H1 O2 0.866(18) 2.023(19) 2.826(2) 153.7(17) 1_655 N2 H2 O2 0.869(18) 2.097(18) 2.8642(19) 146.9(16) 1_655 N3 H3 O1S 0.825(18) 2.302(18) 3.053(3) 151.6(14) 1_565 N3 H3 O2S 0.825(18) 2.393(19) 3.077(4) 140.9(18) 1_565 O1S H1S O1 0.85 1.96 2.806(4) 170.8 . O3S H3S O1 0.85 1.89 2.718(3) 165.7 . O4S H4S O1 0.85 1.85 2.692(3) 172.9 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.26 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.179 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.037