# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'James Wuest ' _publ_contact_author_email james.d.wuest@umontreal.ca _publ_author_name 'James Wuest' data_adam17 _database_code_depnum_ccdc_archive 'CCDC 822591' #TrackingRef '- ADAM17.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C9 H18 O2), C3 H4 N4' _chemical_formula_sum 'C21 H40 N4 O4' _chemical_formula_weight 412.57 _chemical_compound_source 'Synthesized by the authors. See text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2387(8) _cell_length_b 7.0211(11) _cell_length_c 33.169(6) _cell_angle_alpha 90.775(17) _cell_angle_beta 92.741(12) _cell_angle_gamma 101.073(8) _cell_volume 1195.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used 2224 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 66.76 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.146 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.639 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.8932 _exptl_absorpt_correction_T_max 0.9810 _exptl_absorpt_process_details 'Sadabs (Sheldrick, 2008)' _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker microstar diffractometer equiped with a Platinum 135 CCD Detector, a Helios optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 10.0 degree scan in 33 frames over three different parts of the reciprocal space (99 frames total). ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Helios optics' _diffrn_measurement_device_type 'Bruker Microstar' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 14716 _diffrn_reflns_av_R_equivalents 0.064 _diffrn_reflns_av_sigmaI/netI 0.0688 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 67.36 _reflns_number_total 4206 _reflns_number_gt 2529 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker AXS, 2009)' _computing_cell_refinement 'SAINT V7.60A(Bruker AXS, 2008)' _computing_data_reduction 'SAINT V7.60A(Bruker AXS, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'UdMX (Maris, 2004)' _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^)+(0.1500P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4206 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1229 _refine_ls_R_factor_gt 0.0817 _refine_ls_wR_factor_ref 0.2417 _refine_ls_wR_factor_gt 0.2076 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 0.9128(6) -0.0579(5) 0.27239(10) 0.0581(8) Uani 1 1 d . . . H1 H 1.0471 -0.1048 0.2871 0.070 Uiso 1 1 calc R . . N1 N 0.7323(5) -0.1908(4) 0.25210(8) 0.0625(7) Uani 1 1 d . . . C2 C 0.5472(6) -0.1142(5) 0.23322(10) 0.0589(8) Uani 1 1 d . . . H2 H 0.4100 -0.2027 0.2194 0.071 Uiso 1 1 calc R . . N2 N 0.5340(4) 0.0700(4) 0.23168(8) 0.0552(7) Uani 1 1 d . . . C3 C 0.7319(5) 0.1953(4) 0.25231(9) 0.0511(7) Uani 1 1 d . . . N3 N 0.9228(4) 0.1314(4) 0.27399(8) 0.0540(6) Uani 1 1 d . . . N4 N 0.7360(4) 0.3806(4) 0.25042(8) 0.0589(7) Uani 1 1 d . . . H4A H 0.8624 0.4634 0.2632 0.071 Uiso 1 1 calc . . . H4B H 0.6125 0.4232 0.2364 0.071 Uiso 1 1 calc . . . O1 O 1.3184(4) 0.3353(3) 0.32163(7) 0.0665(7) Uani 1 1 d . . . H1A H 1.1893 0.2802 0.3070 0.100 Uiso 1 1 calc . . . O2 O 1.1648(4) 0.5999(3) 0.30556(7) 0.0671(7) Uani 1 1 d . . . C4 C 1.3238(5) 0.5228(5) 0.32307(9) 0.0529(8) Uani 1 1 d . . . C5 C 1.5528(5) 0.6326(5) 0.34904(10) 0.0568(8) Uani 1 1 d . . . H5A H 1.5598 0.5664 0.3751 0.068 Uiso 1 1 calc R . . H5B H 1.7152 0.6258 0.3355 0.068 Uiso 1 1 calc R . . C6 C 1.5454(5) 0.8424(5) 0.35744(10) 0.0577(8) Uani 1 1 d . . . H6A H 1.3868 0.8510 0.3719 0.069 Uiso 1 1 calc R . . H6B H 1.5363 0.9100 0.3316 0.069 Uiso 1 1 calc R . . C7 C 1.7863(6) 0.9435(5) 0.38295(10) 0.0606(8) Uani 1 1 d . . . H7A H 1.7953 0.8735 0.4085 0.073 Uiso 1 1 calc R . . H7B H 1.9436 0.9338 0.3683 0.073 Uiso 1 1 calc R . . C8 C 1.7908(5) 1.1542(5) 0.39280(11) 0.0609(9) Uani 1 1 d . . . H8A H 1.6326 1.1649 0.4071 0.073 Uiso 1 1 calc R . . H8B H 1.7860 1.2255 0.3673 0.073 Uiso 1 1 calc R . . C9 C 2.0310(6) 1.2497(5) 0.41889(10) 0.0605(8) Uani 1 1 d . . . H9A H 2.0355 1.1771 0.4442 0.073 Uiso 1 1 calc R . . H9B H 2.1885 1.2380 0.4044 0.073 Uiso 1 1 calc R . . C10 C 2.0427(5) 1.4609(5) 0.42952(10) 0.0592(8) Uani 1 1 d . . . H10A H 1.8778 1.4748 0.4416 0.071 Uiso 1 1 calc R . . H10B H 2.0572 1.5362 0.4044 0.071 Uiso 1 1 calc R . . C11 C 2.2702(6) 1.5472(5) 0.45898(11) 0.0654(9) Uani 1 1 d . . . H11A H 2.2565 1.4708 0.4839 0.078 Uiso 1 1 calc R . . H11B H 2.4350 1.5340 0.4468 0.078 Uiso 1 1 calc R . . C12 C 2.2832(7) 1.7585(5) 0.47023(12) 0.0758(11) Uani 1 1 d . . . H12A H 2.3003 1.8361 0.4458 0.114 Uiso 1 1 calc R . . H12B H 2.4341 1.8035 0.4889 0.114 Uiso 1 1 calc R . . H12C H 2.1237 1.7728 0.4832 0.114 Uiso 1 1 calc R . . O3 O 0.1398(4) 0.1573(3) 0.18296(7) 0.0655(6) Uani 1 1 d . . . H3 H 0.2603 0.1406 0.1994 0.098 Uiso 1 1 calc . . . O4 O 0.3030(4) 0.4679(3) 0.19793(7) 0.0659(7) Uani 1 1 d . . . C13 C 0.1423(5) 0.3453(5) 0.17983(9) 0.0546(8) Uani 1 1 d . . . C14 C -0.0681(6) 0.3873(5) 0.15087(10) 0.0605(8) Uani 1 1 d . . . H14A H -0.2365 0.3089 0.1583 0.073 Uiso 1 1 calc R . . H14B H -0.0338 0.3439 0.1235 0.073 Uiso 1 1 calc R . . C15 C -0.0949(6) 0.5974(5) 0.14925(10) 0.0577(8) Uani 1 1 d . . . H15A H 0.0771 0.6792 0.1448 0.069 Uiso 1 1 calc R . . H15B H -0.1529 0.6375 0.1755 0.069 Uiso 1 1 calc R . . C16 C -0.2896(6) 0.6309(5) 0.11563(10) 0.0594(8) Uani 1 1 d . . . H16A H -0.2270 0.5938 0.0895 0.071 Uiso 1 1 calc R . . H16B H -0.4583 0.5434 0.1196 0.071 Uiso 1 1 calc R . . C17 C -0.3351(6) 0.8362(5) 0.11305(10) 0.0597(8) Uani 1 1 d . . . H17A H -0.1664 0.9249 0.1099 0.072 Uiso 1 1 calc R . . H17B H -0.4048 0.8723 0.1387 0.072 Uiso 1 1 calc R . . C18 C -0.5246(6) 0.8642(5) 0.07801(10) 0.0584(8) Uani 1 1 d . . . H18A H -0.4589 0.8217 0.0526 0.070 Uiso 1 1 calc R . . H18B H -0.6954 0.7795 0.0819 0.070 Uiso 1 1 calc R . . C19 C -0.5641(6) 1.0711(5) 0.07363(10) 0.0611(9) Uani 1 1 d . . . H19A H -0.3948 1.1555 0.0686 0.073 Uiso 1 1 calc R . . H19B H -0.6246 1.1156 0.0993 0.073 Uiso 1 1 calc R . . C20 C -0.7605(6) 1.0938(5) 0.03943(10) 0.0638(9) Uani 1 1 d . . . H20A H -0.7073 1.0386 0.0143 0.077 Uiso 1 1 calc R . . H20B H -0.9327 1.0171 0.0456 0.077 Uiso 1 1 calc R . . C21 C -0.7882(7) 1.3010(6) 0.03218(12) 0.0767(10) Uani 1 1 d . . . H21A H -0.8477 1.3556 0.0566 0.115 Uiso 1 1 calc R . . H21B H -0.9155 1.3037 0.0097 0.115 Uiso 1 1 calc R . . H21C H -0.6194 1.3780 0.0256 0.115 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 C1 0.0528(16) 0.050(2) 0.069(2) 0.0003(15) -0.0057(14) 0.0037(13) N1 0.0595(15) 0.0455(17) 0.0779(18) -0.0049(13) -0.0093(13) 0.0020(12) C2 0.0550(16) 0.043(2) 0.073(2) -0.0066(14) -0.0090(14) -0.0011(13) N2 0.0480(13) 0.0438(16) 0.0692(16) -0.0051(12) -0.0065(11) 0.0000(11) C3 0.0462(15) 0.0436(19) 0.0612(18) -0.0005(13) -0.0005(13) 0.0032(12) N3 0.0474(12) 0.0446(16) 0.0669(16) -0.0007(11) -0.0059(11) 0.0032(10) N4 0.0515(13) 0.0426(17) 0.0764(18) -0.0047(12) -0.0156(12) -0.0018(11) O1 0.0552(12) 0.0503(15) 0.0874(16) -0.0053(11) -0.0210(10) 0.0004(10) O2 0.0570(12) 0.0496(14) 0.0891(16) -0.0079(11) -0.0240(11) 0.0033(10) C4 0.0448(14) 0.047(2) 0.0628(18) -0.0052(14) -0.0034(13) -0.0001(13) C5 0.0427(14) 0.055(2) 0.0688(19) -0.0026(15) -0.0080(13) 0.0027(13) C6 0.0428(14) 0.056(2) 0.069(2) -0.0087(15) -0.0085(13) 0.0008(13) C7 0.0460(15) 0.058(2) 0.074(2) -0.0103(16) -0.0106(14) 0.0036(13) C8 0.0413(14) 0.060(2) 0.077(2) -0.0122(16) -0.0093(14) 0.0026(13) C9 0.0454(15) 0.061(2) 0.072(2) -0.0109(16) -0.0084(14) 0.0050(13) C10 0.0461(15) 0.059(2) 0.068(2) -0.0103(15) -0.0074(14) 0.0024(13) C11 0.0510(16) 0.065(2) 0.074(2) -0.0102(17) -0.0110(15) -0.0002(15) C12 0.072(2) 0.060(3) 0.084(2) -0.0125(18) -0.0126(18) -0.0080(17) O3 0.0607(12) 0.0465(14) 0.0832(16) -0.0039(11) -0.0214(10) 0.0019(10) O4 0.0544(11) 0.0500(14) 0.0860(16) -0.0067(11) -0.0203(10) -0.0014(9) C13 0.0501(15) 0.047(2) 0.0628(18) -0.0041(14) -0.0019(13) 0.0009(13) C14 0.0532(16) 0.054(2) 0.069(2) -0.0023(15) -0.0113(14) 0.0001(14) C15 0.0509(15) 0.051(2) 0.0663(19) -0.0007(14) -0.0076(14) 0.0006(13) C16 0.0510(16) 0.056(2) 0.0652(19) -0.0011(15) -0.0073(14) -0.0021(14) C17 0.0532(16) 0.053(2) 0.068(2) -0.0019(15) -0.0096(14) 0.0020(14) C18 0.0515(16) 0.053(2) 0.0650(19) -0.0004(15) -0.0088(13) -0.0001(13) C19 0.0534(16) 0.055(2) 0.070(2) 0.0002(15) -0.0072(14) 0.0004(14) C20 0.0570(17) 0.061(2) 0.070(2) 0.0004(16) -0.0089(15) 0.0059(15) C21 0.083(2) 0.064(3) 0.080(2) 0.0025(18) -0.0134(19) 0.0124(18) _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_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 N3 . . 1.320(4) Y C1 N1 . . 1.342(4) Y C1 H1 . . 0.95 ? N1 C2 . . 1.332(4) Y C2 N2 . . 1.310(4) Y C2 H2 . . 0.95 ? N2 C3 . . 1.372(4) Y C3 N4 . . 1.299(4) Y C3 N3 . . 1.353(4) Y N4 H4a . . 0.88 ? N4 H4b . . 0.88 ? O1 C4 . . 1.311(4) Y O1 H1a . . 0.84 ? O2 C4 . . 1.208(3) Y C4 C5 . . 1.518(4) Y C5 C6 . . 1.503(4) Y C5 H5a . . 0.99 ? C5 H5b . . 0.99 ? C6 C7 . . 1.533(4) Y C6 H6a . . 0.99 ? C6 H6b . . 0.99 ? C7 C8 . . 1.506(4) Y C7 H7a . . 0.99 ? C7 H7b . . 0.99 ? C8 C9 . . 1.529(4) Y C8 H8a . . 0.99 ? C8 H8b . . 0.99 ? C9 C10 . . 1.509(4) Y C9 H9a . . 0.99 ? C9 H9b . . 0.99 ? C10 C11 . . 1.529(4) Y C10 H10a . . 0.99 ? C10 H10b . . 0.99 ? C11 C12 . . 1.513(5) Y C11 H11a . . 0.99 ? C11 H11b . . 0.99 ? C12 H12a . . 0.98 ? C12 H12b . . 0.98 ? C12 H12c . . 0.98 ? O3 C13 . . 1.322(4) Y O3 H3 . . 0.84 ? O4 C13 . . 1.212(4) Y C13 C14 . . 1.502(4) Y C14 C15 . . 1.510(4) Y C14 H14a . . 0.99 ? C14 H14b . . 0.99 ? C15 C16 . . 1.526(4) Y C15 H15a . . 0.99 ? C15 H15b . . 0.99 ? C16 C17 . . 1.509(4) Y C16 H16a . . 0.99 ? C16 H16b . . 0.99 ? C17 C18 . . 1.532(4) Y C17 H17a . . 0.99 ? C17 H17b . . 0.99 ? C18 C19 . . 1.514(4) Y C18 H18a . . 0.99 ? C18 H18b . . 0.99 ? C19 C20 . . 1.525(4) Y C19 H19a . . 0.99 ? C19 H19b . . 0.99 ? C20 C21 . . 1.511(5) Y C20 H20a . . 0.99 ? C20 H20b . . 0.99 ? C21 H21a . . 0.98 ? C21 H21b . . 0.98 ? C21 H21c . . 0.98 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N3 C1 N1 . . . 126.7(3) Y N3 C1 H1 . . . 116.7 ? N1 C1 H1 . . . 116.7 ? C2 N1 C1 . . . 113.0(3) Y N2 C2 N1 . . . 127.0(3) Y N2 C2 H2 . . . 116.5 ? N1 C2 H2 . . . 116.5 ? C2 N2 C3 . . . 115.7(3) Y N4 C3 N3 . . . 119.5(3) Y N4 C3 N2 . . . 118.6(3) Y N3 C3 N2 . . . 121.9(3) Y C1 N3 C3 . . . 115.7(3) Y C3 N4 H4A . . . 120 ? C3 N4 H4B . . . 120 ? H4A N4 H4B . . . 120 ? C4 O1 H1A . . . 109.5 ? O2 C4 O1 . . . 123.8(3) Y O2 C4 C5 . . . 123.6(3) Y O1 C4 C5 . . . 112.5(3) Y C6 C5 C4 . . . 114.9(3) Y C6 C5 H5A . . . 108.5 ? C4 C5 H5A . . . 108.5 ? C6 C5 H5B . . . 108.5 ? C4 C5 H5B . . . 108.5 ? H5A C5 H5B . . . 107.5 ? C5 C6 C7 . . . 111.5(3) Y C5 C6 H6A . . . 109.3 ? C7 C6 H6A . . . 109.3 ? C5 C6 H6B . . . 109.3 ? C7 C6 H6B . . . 109.3 ? H6A C6 H6B . . . 108 ? C8 C7 C6 . . . 114.4(3) Y C8 C7 H7A . . . 108.7 ? C6 C7 H7A . . . 108.7 ? C8 C7 H7B . . . 108.7 ? C6 C7 H7B . . . 108.7 ? H7A C7 H7B . . . 107.6 ? C7 C8 C9 . . . 113.1(3) Y C7 C8 H8A . . . 109 ? C9 C8 H8A . . . 109 ? C7 C8 H8B . . . 109 ? C9 C8 H8B . . . 109 ? H8A C8 H8B . . . 107.8 ? C10 C9 C8 . . . 114.8(3) Y C10 C9 H9A . . . 108.6 ? C8 C9 H9A . . . 108.6 ? C10 C9 H9B . . . 108.6 ? C8 C9 H9B . . . 108.6 ? H9A C9 H9B . . . 107.6 ? C9 C10 C11 . . . 113.6(3) Y C9 C10 H10A . . . 108.8 ? C11 C10 H10A . . . 108.8 ? C9 C10 H10B . . . 108.8 ? C11 C10 H10B . . . 108.8 ? H10A C10 H10B . . . 107.7 ? C12 C11 C10 . . . 114.2(3) Y C12 C11 H11A . . . 108.7 ? C10 C11 H11A . . . 108.7 ? C12 C11 H11B . . . 108.7 ? C10 C11 H11B . . . 108.7 ? H11A C11 H11B . . . 107.6 ? C11 C12 H12A . . . 109.5 ? C11 C12 H12B . . . 109.5 ? H12A C12 H12B . . . 109.5 ? C11 C12 H12C . . . 109.5 ? H12A C12 H12C . . . 109.5 ? H12B C12 H12C . . . 109.5 ? C13 O3 H3 . . . 109.5 ? O4 C13 O3 . . . 122.6(3) Y O4 C13 C14 . . . 124.7(3) Y O3 C13 C14 . . . 112.7(2) Y C13 C14 C15 . . . 115.4(3) Y C13 C14 H14A . . . 108.4 ? C15 C14 H14A . . . 108.4 ? C13 C14 H14B . . . 108.4 ? C15 C14 H14B . . . 108.4 ? H14A C14 H14B . . . 107.5 ? C14 C15 C16 . . . 111.8(3) Y C14 C15 H15A . . . 109.2 ? C16 C15 H15A . . . 109.2 ? C14 C15 H15B . . . 109.2 ? C16 C15 H15B . . . 109.2 ? H15A C15 H15B . . . 107.9 ? C17 C16 C15 . . . 115.1(3) Y C17 C16 H16A . . . 108.5 ? C15 C16 H16A . . . 108.5 ? C17 C16 H16B . . . 108.5 ? C15 C16 H16B . . . 108.5 ? H16A C16 H16B . . . 107.5 ? C16 C17 C18 . . . 113.2(3) Y C16 C17 H17A . . . 108.9 ? C18 C17 H17A . . . 108.9 ? C16 C17 H17B . . . 108.9 ? C18 C17 H17B . . . 108.9 ? H17A C17 H17B . . . 107.8 ? C19 C18 C17 . . . 114.2(3) Y C19 C18 H18A . . . 108.7 ? C17 C18 H18A . . . 108.7 ? C19 C18 H18B . . . 108.7 ? C17 C18 H18B . . . 108.7 ? H18A C18 H18B . . . 107.6 ? C18 C19 C20 . . . 113.1(3) Y C18 C19 H19A . . . 109 ? C20 C19 H19A . . . 109 ? C18 C19 H19B . . . 109 ? C20 C19 H19B . . . 109 ? H19A C19 H19B . . . 107.8 ? C21 C20 C19 . . . 114.3(3) Y C21 C20 H20A . . . 108.7 ? C19 C20 H20A . . . 108.7 ? C21 C20 H20B . . . 108.7 ? C19 C20 H20B . . . 108.7 ? H20A C20 H20B . . . 107.6 ? C20 C21 H21A . . . 109.5 ? C20 C21 H21B . . . 109.5 ? H21A C21 H21B . . . 109.5 ? C20 C21 H21C . . . 109.5 ? H21A C21 H21C . . . 109.5 ? H21B C21 H21C . . . 109.5 ? 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 N4 H4A O2 0.88 2.14 2.994(3) 164.1 . N4 H4B O4 0.88 2.09 2.956(3) 168.4 . O1 H1A N3 0.84 1.87 2.707(3) 172.9 . O3 H3 N2 0.84 1.89 2.729(3) 171.6 . _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 67.36 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.306 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.067 #=== END OF THE CIF FILE # Attachment '- ADAM19.cif' data_adam19 _database_code_depnum_ccdc_archive 'CCDC 822592' #TrackingRef '- ADAM19.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C7 H14 O2), C3 H5 N5' _chemical_formula_sum 'C17 H33 N5 O4' _chemical_formula_weight 371.48 _chemical_compound_source 'Synthesized by the authors. See text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pmn21 _symmetry_space_group_name_hall 'P 2ac -2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 51.630(4) _cell_length_b 4.7775(3) _cell_length_c 4.1290(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1018.47(12) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used 4546 _cell_measurement_theta_min 3.42 _cell_measurement_theta_max 63.28 _exptl_crystal_description platelet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.211 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.713 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.9257 _exptl_absorpt_correction_T_max 0.9719 _exptl_absorpt_process_details 'Sadabs (Sheldrick, 2008)' _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker microstar diffractometer equiped with a Platinum 135 CCD Detector, a Helios optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 10.0 degree scan in 33 frames over three different parts of the reciprocal space (99 frames total). ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Helios optics' _diffrn_measurement_device_type 'Bruker Microstar' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 13035 _diffrn_reflns_av_R_equivalents 0.071 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -61 _diffrn_reflns_limit_h_max 61 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 3 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 67.49 _reflns_number_total 1060 _reflns_number_gt 962 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker AXS, 2009)' _computing_cell_refinement 'SAINT V7.60A(Bruker AXS, 2008)' _computing_data_reduction 'SAINT V7.60A(Bruker AXS, 2008)' _computing_structure_solution 'SIR2004 (Burla et al., 2004)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'UdMX (Maris, 2004)' _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^)+(0.1072P)^2^+2.8115P] 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_abs_structure_details 'Friedel Pairs merged' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1060 _refine_ls_number_parameters 122 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0831 _refine_ls_R_factor_gt 0.0793 _refine_ls_wR_factor_ref 0.2424 _refine_ls_wR_factor_gt 0.2398 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 0.43664(9) 0.3685(10) 0.3526(15) 0.0613(15) Uani 1 1 d . . . H1 H 0.4481 0.2679 0.2680 0.092 Uiso 1 1 calc . . . O2 O 0.41088(9) 0.0585(10) 0.1135(14) 0.0560(13) Uani 1 1 d . . . C1 C 0.41368(13) 0.2606(14) 0.2913(19) 0.0498(16) Uani 1 1 d . . . C2 C 0.39186(13) 0.4230(16) 0.4370(19) 0.0559(18) Uani 1 1 d . . . H2A H 0.3876 0.5824 0.2932 0.067 Uiso 1 1 calc R . . H2B H 0.3975 0.5004 0.6478 0.067 Uiso 1 1 calc R . . C3 C 0.36745(13) 0.2465(14) 0.489(2) 0.0516(17) Uani 1 1 d . . . H3A H 0.3712 0.0959 0.6467 0.062 Uiso 1 1 calc R . . H3B H 0.3624 0.1575 0.2817 0.062 Uiso 1 1 calc R . . C4 C 0.34477(13) 0.4236(18) 0.614(2) 0.0617(19) Uani 1 1 d . . . H4A H 0.3502 0.5220 0.8142 0.074 Uiso 1 1 calc R . . H4B H 0.3403 0.5670 0.4505 0.074 Uiso 1 1 calc R . . C5 C 0.32083(13) 0.2486(15) 0.687(2) 0.0558(19) Uani 1 1 d . . . H5A H 0.3253 0.1074 0.8532 0.067 Uiso 1 1 calc R . . H5B H 0.3158 0.1469 0.4878 0.067 Uiso 1 1 calc R . . C6 C 0.29775(13) 0.4181(18) 0.806(2) 0.067(2) Uani 1 1 d . . . H6A H 0.2929 0.5561 0.6371 0.080 Uiso 1 1 calc R . . H6B H 0.3029 0.5232 1.0021 0.080 Uiso 1 1 calc R . . C7 C 0.27424(14) 0.238(2) 0.884(3) 0.076(3) Uani 1 1 d . . . H7A H 0.2672 0.1593 0.6830 0.114 Uiso 1 1 calc R . . H7B H 0.2610 0.3530 0.9896 0.114 Uiso 1 1 calc R . . H7C H 0.2794 0.0856 1.0290 0.114 Uiso 1 1 calc R . . C8 C 0.47815(13) -0.0918(17) -0.1215(18) 0.056(2) Uani 1 1 d . . . C9 C 0.5000 0.233(2) 0.174(3) 0.051(2) Uani 1 2 d S . . H9 H 0.5000 0.3891 0.3167 0.061 Uiso 1 2 calc SR . . N1 N 0.47715(10) 0.1351(12) 0.0843(15) 0.0504(15) Uani 1 1 d . . . N2 N 0.5000 -0.2052(14) -0.228(2) 0.0463(19) Uani 1 2 d S . . N3 N 0.45551(10) -0.1939(10) -0.2075(16) 0.0498(14) Uani 1 1 d . . . H3C H 0.4547 -0.3394 -0.3378 0.060 Uiso 1 1 calc . . . H3D H 0.4412 -0.1166 -0.1348 0.060 Uiso 1 1 calc . . . 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 0.062(3) 0.065(3) 0.057(3) -0.021(3) 0.004(3) -0.003(2) O2 0.073(3) 0.045(2) 0.050(3) -0.016(3) 0.002(3) -0.003(2) C1 0.064(4) 0.050(4) 0.035(4) 0.004(4) 0.003(3) 0.001(3) C2 0.066(4) 0.063(4) 0.039(4) -0.011(4) 0.000(3) -0.001(3) C3 0.073(4) 0.037(3) 0.045(4) 0.001(3) 0.002(4) 0.000(3) C4 0.061(4) 0.083(5) 0.041(4) 0.000(5) 0.002(4) 0.000(4) C5 0.075(4) 0.048(4) 0.045(4) 0.000(3) -0.001(4) 0.001(3) C6 0.065(4) 0.088(5) 0.049(5) -0.001(5) 0.007(4) 0.002(4) C7 0.066(4) 0.092(6) 0.070(7) -0.006(6) 0.005(4) 0.002(4) C8 0.058(4) 0.071(5) 0.039(4) 0.030(4) -0.001(3) -0.003(4) C9 0.065(6) 0.048(5) 0.040(6) 0.016(5) 0.000 0.000 N1 0.063(3) 0.057(3) 0.032(3) 0.001(3) -0.002(3) 0.004(3) N2 0.067(5) 0.033(3) 0.039(5) 0.003(4) 0.000 0.000 N3 0.073(3) 0.033(2) 0.043(4) -0.009(3) 0.001(3) -0.002(2) _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_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . . 1.317(8) Y O1 H1 . . 0.84 ? O2 C1 . . 1.222(8) Y C1 C2 . . 1.494(9) Y C2 C3 . . 1.532(9) Y C2 H2a . . 0.99 ? C2 H2b . . 0.99 ? C3 C4 . . 1.534(10) Y C3 H3a . . 0.99 ? C3 H3b . . 0.99 ? C4 C5 . . 1.522(10) Y C4 H4a . . 0.99 ? C4 H4b . . 0.99 ? C5 C6 . . 1.522(10) Y C5 H5a . . 0.99 ? C5 H5b . . 0.99 ? C6 C7 . . 1.523(11) Y C6 H6a . . 0.99 ? C6 H6b . . 0.99 ? C7 H7a . . 0.98 ? C7 H7b . . 0.98 ? C7 H7c . . 0.98 ? C8 N3 . . 1.315(9) Y C8 N2 . . 1.327(8) Y C8 N1 . . 1.378(10) Y C9 N1 . . 1.322(7) Y C9 N1 . 3_655 1.322(7) Y C9 H9 . . 0.95 ? N2 C8 . 3_655 1.327(8) Y N3 H3c . . 0.88 ? N3 H3d . . 0.88 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 O1 H1 . . . 109.5 ? O2 C1 O1 . . . 122.1(6) Y O2 C1 C2 . . . 124.3(6) Y O1 C1 C2 . . . 113.5(6) Y C1 C2 C3 . . . 113.0(6) Y C1 C2 H2A . . . 109 ? C3 C2 H2A . . . 109 ? C1 C2 H2B . . . 109 ? C3 C2 H2B . . . 109 ? H2A C2 H2B . . . 107.8 ? C2 C3 C4 . . . 111.8(6) Y C2 C3 H3A . . . 109.3 ? C4 C3 H3A . . . 109.3 ? C2 C3 H3B . . . 109.3 ? C4 C3 H3B . . . 109.3 ? H3A C3 H3B . . . 107.9 ? C5 C4 C3 . . . 112.5(7) Y C5 C4 H4A . . . 109.1 ? C3 C4 H4A . . . 109.1 ? C5 C4 H4B . . . 109.1 ? C3 C4 H4B . . . 109.1 ? H4A C4 H4B . . . 107.8 ? C4 C5 C6 . . . 114.0(6) Y C4 C5 H5A . . . 108.7 ? C6 C5 H5A . . . 108.7 ? C4 C5 H5B . . . 108.7 ? C6 C5 H5B . . . 108.7 ? H5A C5 H5B . . . 107.6 ? C5 C6 C7 . . . 113.1(7) Y C5 C6 H6A . . . 109 ? C7 C6 H6A . . . 109 ? C5 C6 H6B . . . 109 ? C7 C6 H6B . . . 109 ? H6A C6 H6B . . . 107.8 ? C6 C7 H7A . . . 109.5 ? C6 C7 H7B . . . 109.5 ? H7A C7 H7B . . . 109.5 ? C6 C7 H7C . . . 109.5 ? H7A C7 H7C . . . 109.5 ? H7B C7 H7C . . . 109.5 ? N3 C8 N2 . . . 121.0(8) Y N3 C8 N1 . . . 115.1(6) Y N2 C8 N1 . . . 123.9(7) Y N1 C9 N1 . . 3_655 126.3(1) Y N1 C9 H9 . . . 116.9 ? N1 C9 H9 3_655 . . 116.9 ? C9 N1 C8 . . . 114.7(7) Y C8 N2 C8 . . 3_655 116.5(9) Y C8 N3 H3C . . . 120 ? C8 N3 H3D . . . 120 ? H3C N3 H3D . . . 120 ? 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 H1 N1 0.84 1.79 2.616(7) 165.5 . N3 H3C O1 0.88 2.11 2.936(7) 156 1_544 N3 H3D O2 0.88 2.05 2.919(7) 169.8 . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 67.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.342 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.063 #=== END OF THE CIF FILE # Attachment '- ADAM30.cif' data_adam30 _database_code_depnum_ccdc_archive 'CCDC 822593' #TrackingRef '- ADAM30.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H41 N3 O4' _chemical_formula_weight 411.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 5.4040(7) _cell_length_b 5.4119(8) _cell_length_c 40.042(7) _cell_angle_alpha 90.00 _cell_angle_beta 96.158(9) _cell_angle_gamma 90.00 _cell_volume 1164.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.174 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.642 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8306 _exptl_absorpt_correction_T_max 0.9098 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12526 _diffrn_reflns_av_R_equivalents 0.0811 _diffrn_reflns_av_sigmaI/netI 0.1028 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -48 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 73.23 _reflns_number_total 4236 _reflns_number_gt 2454 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1447P)^2^+2.4824P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(8) _refine_ls_number_reflns 4236 _refine_ls_number_parameters 264 _refine_ls_number_restraints 57 _refine_ls_R_factor_all 0.1601 _refine_ls_R_factor_gt 0.1129 _refine_ls_wR_factor_ref 0.3339 _refine_ls_wR_factor_gt 0.3017 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.049 _refine_ls_shift/su_mean 0.011 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.2033(13) 0.2693(13) 0.6853(2) 0.0538(18) Uani 1 1 d U . . H1D H 0.2063 0.1544 0.7009 0.065 Uiso 1 1 d R . . H1E H 0.0797 0.2732 0.6690 0.065 Uiso 1 1 d R . . N2 N 0.3491(11) 0.6171(12) 0.66112(18) 0.0451(14) Uani 1 1 d U . . C22 C 0.7240(14) 0.7951(14) 0.6853(2) 0.0498(19) Uani 1 1 d U . . H22 H 0.8440 0.9185 0.6856 0.060 Uiso 1 1 calc R . . N4 N 0.5664(12) 0.4344(11) 0.70968(18) 0.0450(14) Uani 1 1 d U . . C19 C 0.5215(14) 0.7878(13) 0.6618(2) 0.0458(16) Uani 1 1 d U . . H19 H 0.5052 0.9103 0.6454 0.055 Uiso 1 1 calc R . . C20 C 0.7381(15) 0.6028(14) 0.7091(2) 0.0505(18) Uani 1 1 d U . . H20 H 0.8762 0.5954 0.7250 0.061 Uiso 1 1 calc R . . C21 C 0.3769(13) 0.4409(13) 0.6856(2) 0.0416(15) Uani 1 1 d U . . O1 O -0.1905(10) 0.2818(10) 0.63157(16) 0.0548(14) Uani 1 1 d U . . O2 O -0.0348(10) 0.6243(10) 0.61121(16) 0.0516(14) Uani 1 1 d U . . H2C H 0.0805 0.5992 0.6268 0.062 Uiso 1 1 d R . . C1 C -1.6473(16) -0.3212(14) 0.4651(2) 0.053(2) Uani 1 1 d U . . H1A H -1.5608 -0.4738 0.4625 0.079 Uiso 1 1 calc R . . H1B H -1.7591 -0.2899 0.4453 0.079 Uiso 1 1 calc R . . H1C H -1.7402 -0.3324 0.4842 0.079 Uiso 1 1 calc R . . C2 C -1.4610(17) -0.1122(16) 0.4704(2) 0.055(2) Uani 1 1 d U . . H2A H -1.3622 -0.1084 0.4515 0.066 Uiso 1 1 calc R . . H2B H -1.5509 0.0429 0.4705 0.066 Uiso 1 1 calc R . . C3 C -1.2899(14) -0.1313(14) 0.5020(2) 0.0488(18) Uani 1 1 d U . . H3A H -1.1947 -0.2828 0.5014 0.059 Uiso 1 1 calc R . . H3B H -1.3896 -0.1442 0.5207 0.059 Uiso 1 1 calc R . . C4 C -1.1095(15) 0.0826(15) 0.5088(2) 0.0497(18) Uani 1 1 d U . . H4A H -1.0086 0.0956 0.4902 0.060 Uiso 1 1 calc R . . H4B H -1.2040 0.2346 0.5096 0.060 Uiso 1 1 calc R . . C5 C -0.9403(16) 0.0582(15) 0.5409(2) 0.0497(17) Uani 1 1 d U . . H5A H -0.8474 -0.0948 0.5404 0.060 Uiso 1 1 calc R . . H5B H -1.0405 0.0489 0.5596 0.060 Uiso 1 1 calc R . . C6 C -0.7579(14) 0.2727(16) 0.5468(2) 0.0485(18) Uani 1 1 d U . . H6A H -0.6651 0.2863 0.5275 0.058 Uiso 1 1 calc R . . H6B H -0.8525 0.4241 0.5481 0.058 Uiso 1 1 calc R . . C7 C -0.5744(14) 0.2529(15) 0.5781(2) 0.0484(18) Uani 1 1 d U . . H7A H -0.6659 0.2393 0.5975 0.058 Uiso 1 1 calc R . . H7B H -0.4773 0.1031 0.5768 0.058 Uiso 1 1 calc R . . C8 C -0.4017(14) 0.4684(15) 0.5827(2) 0.0490(17) Uani 1 1 d U . . H8A H -0.3276 0.4941 0.5620 0.059 Uiso 1 1 calc R . . H8B H -0.4986 0.6145 0.5866 0.059 Uiso 1 1 calc R . . C9 C -0.1990(15) 0.4458(16) 0.6105(2) 0.0507(17) Uani 1 1 d U . . O3 O 0.2612(10) -0.0796(12) 0.73930(16) 0.0581(16) Uani 1 1 d U . . O4 O 0.6203(10) 0.0938(10) 0.75974(15) 0.0536(14) Uani 1 1 d U . . H4C H 0.5930 0.1823 0.7425 0.064 Uiso 1 1 d R . . C10 C -0.1963(17) -1.3819(19) 0.9092(2) 0.061(2) Uani 1 1 d U . . H10A H -0.3457 -1.2882 0.9106 0.091 Uiso 1 1 calc R . . H10B H -0.1514 -1.4659 0.9301 0.091 Uiso 1 1 calc R . . H10C H -0.2242 -1.5009 0.8914 0.091 Uiso 1 1 calc R . . C11 C 0.0106(15) -1.2107(16) 0.9021(2) 0.0529(19) Uani 1 1 d U . . H11A H 0.1614 -1.3066 0.9012 0.063 Uiso 1 1 calc R . . H11B H 0.0404 -1.0943 0.9205 0.063 Uiso 1 1 calc R . . C12 C -0.0413(14) -1.0690(17) 0.8698(2) 0.0502(18) Uani 1 1 d U . . H12A H -0.1901 -0.9704 0.8709 0.060 Uiso 1 1 calc R . . H12B H -0.0750 -1.1855 0.8515 0.060 Uiso 1 1 calc R . . C13 C 0.1682(14) -0.9008(16) 0.8621(2) 0.0489(18) Uani 1 1 d U . . H13A H 0.3145 -1.0009 0.8600 0.059 Uiso 1 1 calc R . . H13B H 0.2076 -0.7905 0.8811 0.059 Uiso 1 1 calc R . . C14 C 0.1144(15) -0.7455(15) 0.8304(2) 0.0507(18) Uani 1 1 d U . . H14A H 0.0795 -0.8550 0.8113 0.061 Uiso 1 1 calc R . . H14B H -0.0334 -0.6469 0.8323 0.061 Uiso 1 1 calc R . . C15 C 0.3224(14) -0.5789(16) 0.8241(2) 0.0496(18) Uani 1 1 d U . . H15A H 0.4688 -0.6787 0.8219 0.059 Uiso 1 1 calc R . . H15B H 0.3596 -0.4732 0.8436 0.059 Uiso 1 1 calc R . . C16 C 0.2741(15) -0.4177(16) 0.7933(2) 0.0511(18) Uani 1 1 d U . . H16A H 0.2406 -0.5225 0.7737 0.061 Uiso 1 1 calc R . . H16B H 0.1265 -0.3189 0.7953 0.061 Uiso 1 1 calc R . . C17 C 0.4868(15) -0.2487(15) 0.7881(2) 0.0489(17) Uani 1 1 d U . . H17A H 0.5304 -0.1566 0.8087 0.059 Uiso 1 1 calc R . . H17B H 0.6296 -0.3490 0.7842 0.059 Uiso 1 1 calc R . . C18 C 0.4399(14) -0.0702(14) 0.7600(2) 0.0447(15) Uani 1 1 d U . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.045(3) 0.039(3) 0.075(5) 0.010(3) -0.007(3) -0.015(3) N2 0.033(3) 0.039(3) 0.063(4) 0.003(2) 0.005(2) -0.009(2) C22 0.031(3) 0.025(3) 0.094(6) -0.001(3) 0.009(3) -0.009(3) N4 0.040(3) 0.025(3) 0.068(4) 0.000(2) 0.000(2) -0.008(2) C19 0.037(3) 0.019(3) 0.082(5) -0.005(3) 0.010(3) -0.001(2) C20 0.041(4) 0.035(4) 0.075(5) -0.004(3) 0.004(3) -0.013(3) C21 0.031(3) 0.023(3) 0.070(4) -0.002(2) 0.004(2) 0.000(2) O1 0.045(3) 0.036(3) 0.082(4) 0.006(2) 0.002(3) -0.005(2) O2 0.038(3) 0.040(3) 0.077(4) 0.003(3) 0.006(2) -0.006(2) C1 0.048(4) 0.029(4) 0.081(6) 0.000(4) 0.006(3) -0.007(3) C2 0.057(5) 0.036(4) 0.071(5) 0.004(4) 0.005(3) -0.015(3) C3 0.036(4) 0.026(3) 0.085(5) 0.000(3) 0.003(3) 0.006(2) C4 0.044(4) 0.030(4) 0.074(5) 0.003(3) 0.003(3) -0.001(3) C5 0.042(4) 0.036(4) 0.071(5) 0.004(3) 0.005(3) -0.001(3) C6 0.037(4) 0.036(4) 0.073(5) 0.001(3) 0.007(3) 0.001(3) C7 0.035(4) 0.035(4) 0.075(5) 0.010(3) 0.007(2) -0.004(3) C8 0.033(3) 0.036(4) 0.078(5) 0.004(3) 0.009(2) -0.003(3) C9 0.040(4) 0.038(4) 0.074(5) 0.002(3) 0.008(2) -0.005(3) O3 0.040(3) 0.062(4) 0.070(4) 0.012(3) -0.002(2) -0.012(3) O4 0.048(3) 0.043(3) 0.068(4) 0.002(2) -0.005(3) -0.009(2) C10 0.053(5) 0.058(5) 0.073(6) 0.001(4) 0.013(4) -0.007(4) C11 0.036(4) 0.050(5) 0.072(5) 0.005(3) 0.006(3) 0.005(3) C12 0.033(3) 0.050(5) 0.067(4) 0.001(3) 0.004(3) 0.001(3) C13 0.034(4) 0.042(4) 0.070(5) 0.000(3) 0.003(3) 0.002(3) C14 0.045(4) 0.031(4) 0.075(5) -0.001(3) -0.001(3) 0.000(3) C15 0.034(3) 0.037(4) 0.077(5) 0.004(3) 0.003(3) 0.007(3) C16 0.042(4) 0.042(4) 0.068(4) 0.000(3) 0.001(3) -0.002(3) C17 0.044(4) 0.031(4) 0.070(5) -0.002(3) -0.002(3) 0.000(3) C18 0.039(3) 0.031(3) 0.062(4) -0.007(2) 0.002(2) 0.002(2) _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 N1 C21 1.319(9) . ? N1 H1D 0.8796 . ? N1 H1E 0.8832 . ? N2 C19 1.310(10) . ? N2 C21 1.364(10) . ? C22 C19 1.365(12) . ? C22 C20 1.407(12) . ? C22 H22 0.9300 . ? N4 C20 1.303(10) . ? N4 C21 1.330(10) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? O1 C9 1.222(10) . ? O2 C9 1.310(9) . ? O2 H2C 0.8430 . ? C1 C2 1.514(11) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.491(12) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.519(11) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.502(12) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.525(11) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.515(11) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.493(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.480(12) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? O3 C18 1.205(9) . ? O4 C18 1.319(10) . ? O4 H4C 0.8392 . ? C10 C11 1.503(12) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.502(12) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.510(11) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.525(11) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.483(11) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.510(12) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.500(11) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.484(11) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 N1 H1D 122.2 . . ? C21 N1 H1E 118.1 . . ? H1D N1 H1E 119.8 . . ? C19 N2 C21 117.1(7) . . ? C19 C22 C20 115.2(7) . . ? C19 C22 H22 122.4 . . ? C20 C22 H22 122.4 . . ? C20 N4 C21 117.6(7) . . ? N2 C19 C22 123.4(8) . . ? N2 C19 H19 118.3 . . ? C22 C19 H19 118.3 . . ? N4 C20 C22 122.9(8) . . ? N4 C20 H20 118.6 . . ? C22 C20 H20 118.5 . . ? N1 C21 N4 118.6(7) . . ? N1 C21 N2 117.6(7) . . ? N4 C21 N2 123.8(7) . . ? C9 O2 H2C 110.1 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C1 114.1(7) . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? C2 C3 C4 115.2(7) . . ? C2 C3 H3A 108.5 . . ? C4 C3 H3A 108.5 . . ? C2 C3 H3B 108.5 . . ? C4 C3 H3B 108.5 . . ? H3A C3 H3B 107.5 . . ? C5 C4 C3 113.9(7) . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C4 C5 C6 112.9(7) . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C7 C6 C5 115.4(7) . . ? C7 C6 H6A 108.4 . . ? C5 C6 H6A 108.4 . . ? C7 C6 H6B 108.4 . . ? C5 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? C8 C7 C6 113.1(7) . . ? C8 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C7 115.5(7) . . ? C9 C8 H8A 108.4 . . ? C7 C8 H8A 108.4 . . ? C9 C8 H8B 108.4 . . ? C7 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? O1 C9 O2 123.0(8) . . ? O1 C9 C8 123.3(8) . . ? O2 C9 C8 113.6(8) . . ? C18 O4 H4C 109.1 . . ? C11 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C11 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C10 C11 C12 113.8(7) . . ? C10 C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? C10 C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C11 C12 C13 114.1(7) . . ? C11 C12 H12A 108.7 . . ? C13 C12 H12A 108.7 . . ? C11 C12 H12B 108.7 . . ? C13 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C12 C13 C14 115.0(6) . . ? C12 C13 H13A 108.5 . . ? C14 C13 H13A 108.5 . . ? C12 C13 H13B 108.5 . . ? C14 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? C15 C14 C13 113.3(7) . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? C13 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C14 C15 C16 115.0(7) . . ? C14 C15 H15A 108.5 . . ? C16 C15 H15A 108.5 . . ? C14 C15 H15B 108.5 . . ? C16 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? C17 C16 C15 113.4(7) . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16B 108.9 . . ? C15 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C18 C17 C16 115.5(7) . . ? C18 C17 H17A 108.4 . . ? C16 C17 H17A 108.4 . . ? C18 C17 H17B 108.4 . . ? C16 C17 H17B 108.4 . . ? H17A C17 H17B 107.5 . . ? O3 C18 O4 124.1(8) . . ? O3 C18 C17 123.6(8) . . ? O4 C18 C17 112.3(7) . . ? 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 C21 N2 C19 C22 0.5(12) . . . . ? C20 C22 C19 N2 0.7(12) . . . . ? C21 N4 C20 C22 3.4(12) . . . . ? C19 C22 C20 N4 -2.7(13) . . . . ? C20 N4 C21 N1 178.6(8) . . . . ? C20 N4 C21 N2 -2.1(12) . . . . ? C19 N2 C21 N1 179.5(7) . . . . ? C19 N2 C21 N4 0.2(12) . . . . ? C1 C2 C3 C4 -177.1(8) . . . . ? C2 C3 C4 C5 179.9(8) . . . . ? C3 C4 C5 C6 178.9(7) . . . . ? C4 C5 C6 C7 -177.4(7) . . . . ? C5 C6 C7 C8 -179.6(7) . . . . ? C6 C7 C8 C9 -173.0(7) . . . . ? C7 C8 C9 O1 -10.5(13) . . . . ? C7 C8 C9 O2 172.2(7) . . . . ? C10 C11 C12 C13 -178.7(8) . . . . ? C11 C12 C13 C14 -177.1(7) . . . . ? C12 C13 C14 C15 178.7(7) . . . . ? C13 C14 C15 C16 -178.7(7) . . . . ? C14 C15 C16 C17 179.0(8) . . . . ? C15 C16 C17 C18 -174.6(7) . . . . ? C16 C17 C18 O3 -10.8(12) . . . . ? C16 C17 C18 O4 171.4(7) . . . . ? 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 H1E O1 0.88 1.98 2.860(10) 178.5 . N1 H1D O3 0.88 1.99 2.863(10) 171.0 . O2 H2C N2 0.84 1.89 2.722(9) 167.7 . O4 H4C N4 0.84 1.89 2.716(9) 167.7 . _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 73.23 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.432 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.085