Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Judith A. K. Howard' _publ_contact_author_address ; Department of Chemistry Durham University South Rd Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email J.A.K.HOWARD@DUR.AC.UK _publ_section_title ; The Solid-State Behaviour of 4,6-Dioxo-5,5-diethylenepyrimidine-2-isobutylurea ; loop_ _publ_author_name 'Judith A. K. Howard' 'Pranjal K. Baruah' 'G. J. Sanjayan' 'Elinor Spencer' data_alpha_form _database_code_depnum_ccdc_archive 'CCDC 600450' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,6-Dioxo-5,5-diethylenepyrimidine-2-isobutylurea ; _chemical_name_common 4,6-Dioxo-5,5-diethylenepyrimidine-2-isobutylurea _chemical_melting_point 'not measured' _chemical_formula_moiety 'C15 H21 N4 O3' _chemical_formula_sum 'C15 H21 N4 O3' _chemical_formula_weight 305.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.862(2) _cell_length_b 13.2641(11) _cell_length_c 12.2213(10) _cell_angle_alpha 90.00 _cell_angle_beta 116.676(3) _cell_angle_gamma 90.00 _cell_volume 3456.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2429 _cell_measurement_theta_min 2.274 _cell_measurement_theta_max 22.672 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.174 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.860661 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ; SADABS (Sheldrick, G. M. (1998)). Program for Absorption Correction. University of G\"ottingen, Germany. ; _diffrn_ambient_temperature 298(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 CCD 6K area detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9198 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3033 _reflns_number_gt 1832 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART 1998' _computing_cell_refinement 'Bruker SMART 1998' _computing_data_reduction 'Bruker SAINT 1998' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. No realistic model for the hydrogen atoms bound to the disordered C13 atom could be obtained. For this reason, although this atom is sp3 hybridised, it connectivity is only three. It should be noted that both the formula unit and the molecular weight are therefore inaccurate. ; _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^)+(0.1762P)^2^+2.9873P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef 'not refined' _refine_ls_number_reflns 3033 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1386 _refine_ls_R_factor_gt 0.0940 _refine_ls_wR_factor_ref 0.3113 _refine_ls_wR_factor_gt 0.2791 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.002 _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 0.7995(5) -0.1208(8) -0.0324(11) 0.192(4) Uani 1 1 d . . . H1A H 0.7718 -0.1266 -0.1151 0.230 Uiso 1 1 calc R . . H1B H 0.7886 -0.1465 0.0263 0.230 Uiso 1 1 calc R . . C2 C 0.8529(4) -0.0774(6) 0.0008(8) 0.136(2) Uani 1 1 d . . . H2 H 0.8789 -0.0735 0.0846 0.164 Uiso 1 1 calc R . . C3 C 0.8759(3) -0.0349(4) -0.0776(5) 0.1034(19) Uani 1 1 d . . . H3A H 0.8468 -0.0507 -0.1617 0.124 Uiso 1 1 calc R . . H3B H 0.9156 -0.0665 -0.0604 0.124 Uiso 1 1 calc R . . C4 C 0.88549(19) 0.0811(3) -0.0657(4) 0.0734(12) Uani 1 1 d . C . C5 C 0.9155(3) 0.1133(6) -0.1487(6) 0.117(2) Uani 1 1 d . . . H5A H 0.9531 0.0739 -0.1281 0.140 Uiso 1 1 calc R . . H5B H 0.8865 0.0993 -0.2334 0.140 Uiso 1 1 calc R . . C6 C 0.9317(7) 0.2220(11) -0.1353(14) 0.218(7) Uani 1 1 d . . . H6 H 0.9448 0.2423 -0.0547 0.261 Uiso 1 1 calc R . . C7 C 0.9328(9) 0.2786(15) -0.1849(15) 0.296(10) Uani 1 1 d . . . H7A H 0.9209 0.2696 -0.2678 0.356 Uiso 1 1 calc R . . H7B H 0.9458 0.3417 -0.1492 0.356 Uiso 1 1 calc R . . C8 C 0.82237(18) 0.1315(4) -0.1071(4) 0.0728(12) Uani 1 1 d . . . C9 C 0.93034(17) 0.1058(3) 0.0647(4) 0.0710(12) Uani 1 1 d . . . C10 C 0.84820(15) 0.1976(3) 0.0831(3) 0.0531(9) Uani 1 1 d . . . C11 C 0.87218(19) 0.2865(3) 0.2763(4) 0.0682(11) Uani 1 1 d . . . C12 C 0.8785(3) 0.3800(5) 0.4522(5) 0.128(3) Uani 1 1 d . . . H12A H 0.9184 0.3454 0.4935 0.154 Uiso 1 1 calc R A 1 H12B H 0.8547 0.3667 0.4974 0.154 Uiso 1 1 calc R A 1 C13A C 0.8899(6) 0.4911(9) 0.4527(11) 0.096(4) Uiso 0.58(3) 1 d P B 1 C13B C 0.8733(9) 0.4786(12) 0.4790(16) 0.094(6) Uiso 0.42(3) 1 d P B 2 C14A C 0.8314(8) 0.5519(12) 0.3952(16) 0.135(6) Uiso 0.58(3) 1 d P B 1 H14A H 0.8032 0.5311 0.4272 0.202 Uiso 0.58(3) 1 calc PR B 1 H14B H 0.8120 0.5419 0.3081 0.202 Uiso 0.58(3) 1 calc PR B 1 H14C H 0.8414 0.6220 0.4131 0.202 Uiso 0.58(3) 1 calc PR B 1 C14B C 0.8139(9) 0.5321(15) 0.434(2) 0.125(7) Uiso 0.42(3) 1 d P B 2 H14D H 0.7886 0.5156 0.3493 0.188 Uiso 0.42(3) 1 calc PR B 2 H14E H 0.8216 0.6034 0.4418 0.188 Uiso 0.42(3) 1 calc PR B 2 H14F H 0.7924 0.5127 0.4807 0.188 Uiso 0.42(3) 1 calc PR B 2 C15 C 0.9248(4) 0.5237(7) 0.5916(7) 0.174(4) Uani 1 1 d . . . H15A H 0.9647 0.4911 0.6412 0.261 Uiso 1 1 d R B . H15B H 0.9294 0.5948 0.6120 0.261 Uiso 1 1 d R . . H15C H 0.8940 0.4959 0.6147 0.261 Uiso 1 1 d R . . N1 N 0.80510(13) 0.1834(2) -0.0302(3) 0.0602(9) Uani 1 1 d . C . N2 N 0.90735(14) 0.1607(3) 0.1316(3) 0.0667(10) Uani 1 1 d . C . H2N H 0.933(2) 0.171(3) 0.209(4) 0.080 Uiso 1 1 d . . . N3 N 0.83177(14) 0.2523(2) 0.1570(3) 0.0597(9) Uani 1 1 d . C . H3N H 0.7992(19) 0.268(3) 0.124(4) 0.072 Uiso 1 1 d . . . N4 N 0.84412(19) 0.3403(3) 0.3272(3) 0.0917(14) Uani 1 1 d . B . H4N H 0.809(3) 0.341(5) 0.292(5) 0.110 Uiso 1 1 d . . . O1A O 0.7898(3) 0.1405(7) -0.2194(5) 0.061(3) Uiso 0.54(2) 1 d P C 1 O1B O 0.7778(4) 0.1008(10) -0.2098(6) 0.067(3) Uiso 0.46(2) 1 d P C 2 O2A O 0.9870(2) 0.0914(7) 0.1062(5) 0.066(2) Uiso 0.61(3) 1 d P C 1 O2B O 0.9802(4) 0.0539(13) 0.1263(9) 0.073(4) Uiso 0.39(3) 1 d P C 2 O3 O 0.92814(13) 0.2662(3) 0.3247(3) 0.0908(11) Uani 1 1 d . C . 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 0.199(9) 0.164(9) 0.225(11) 0.026(8) 0.108(9) 0.007(8) C2 0.168(7) 0.114(5) 0.127(6) 0.006(4) 0.066(6) -0.005(5) C3 0.100(4) 0.106(4) 0.082(3) -0.017(3) 0.020(3) 0.034(3) C4 0.071(2) 0.085(3) 0.063(2) -0.004(2) 0.029(2) 0.026(2) C5 0.127(5) 0.143(6) 0.110(4) 0.027(4) 0.080(4) 0.061(4) C6 0.298(14) 0.202(13) 0.276(14) 0.107(11) 0.240(13) 0.084(11) C7 0.47(3) 0.252(18) 0.245(17) -0.078(14) 0.229(19) -0.122(18) C8 0.063(2) 0.096(3) 0.048(2) -0.004(2) 0.0147(18) 0.026(2) C9 0.047(2) 0.091(3) 0.073(3) -0.002(2) 0.0247(19) 0.0226(19) C10 0.0489(19) 0.057(2) 0.051(2) 0.0025(15) 0.0197(17) 0.0105(16) C11 0.064(2) 0.068(2) 0.055(2) -0.0019(18) 0.0106(19) 0.0172(19) C12 0.150(5) 0.130(5) 0.060(3) -0.023(3) 0.008(3) 0.061(4) C15 0.178(7) 0.165(7) 0.112(5) -0.057(5) 0.006(5) -0.003(6) N1 0.0563(17) 0.071(2) 0.0492(18) -0.0041(14) 0.0199(15) 0.0196(14) N2 0.0482(17) 0.083(2) 0.061(2) -0.0087(16) 0.0169(15) 0.0183(15) N3 0.0491(17) 0.073(2) 0.0480(18) -0.0037(14) 0.0141(14) 0.0175(15) N4 0.084(2) 0.111(3) 0.057(2) -0.023(2) 0.011(2) 0.037(2) O3 0.0654(19) 0.113(3) 0.0660(19) -0.0192(16) 0.0047(15) 0.0224(16) _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 C2 1.286(11) . ? C1 H1A 0.9300 . ? C1 H1B 0.9300 . ? C2 C3 1.419(9) . ? C2 H2 0.9300 . ? C3 C4 1.552(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C9 1.504(6) . ? C4 C8 1.513(5) . ? C4 C5 1.541(7) . ? C5 C6 1.483(16) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 0.972(17) . ? C6 H6 0.9300 . ? C7 H7A 0.9300 . ? C7 H7B 0.9300 . ? C8 O1A 1.243(6) . ? C8 O1B 1.295(8) . ? C8 N1 1.369(5) . ? C9 O2A 1.227(6) . ? C9 O2B 1.286(11) . ? C9 N2 1.378(5) . ? C10 N1 1.316(4) . ? C10 N3 1.347(5) . ? C10 N2 1.354(4) . ? C11 O3 1.223(5) . ? C11 N4 1.310(5) . ? C11 N3 1.414(5) . ? C12 C13B 1.367(16) . ? C12 N4 1.470(6) . ? C12 C13A 1.498(14) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13A C14A 1.487(17) . ? C13A C15 1.578(13) . ? C13B C14B 1.45(2) . ? C13B C15 1.497(15) . ? C13B H15C 1.5196 . ? C14A H14A 0.9600 . ? C14A H14B 0.9600 . ? C14A H14C 0.9600 . ? C14B H14D 0.9600 . ? C14B H14E 0.9600 . ? C14B H14F 0.9600 . ? C15 H15A 0.9698 . ? C15 H15B 0.9700 . ? C15 H15C 0.9702 . ? N2 H2N 0.88(4) . ? N3 H3N 0.73(4) . ? N4 H4N 0.75(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 120.0 . . ? C2 C1 H1B 120.0 . . ? H1A C1 H1B 120.0 . . ? C1 C2 C3 126.4(9) . . ? C1 C2 H2 116.8 . . ? C3 C2 H2 116.8 . . ? C2 C3 C4 114.6(5) . . ? C2 C3 H3A 108.6 . . ? C4 C3 H3A 108.6 . . ? C2 C3 H3B 108.6 . . ? C4 C3 H3B 108.6 . . ? H3A C3 H3B 107.6 . . ? C9 C4 C8 112.7(3) . . ? C9 C4 C5 108.5(4) . . ? C8 C4 C5 110.1(4) . . ? C9 C4 C3 108.7(4) . . ? C8 C4 C3 108.9(4) . . ? C5 C4 C3 107.8(4) . . ? C6 C5 C4 111.8(6) . . ? C6 C5 H5A 109.3 . . ? C4 C5 H5A 109.3 . . ? C6 C5 H5B 109.3 . . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 139.5(19) . . ? C7 C6 H6 110.2 . . ? C5 C6 H6 110.2 . . ? C6 C7 H7A 120.0 . . ? C6 C7 H7B 120.0 . . ? H7A C7 H7B 120.0 . . ? O1A C8 O1B 28.9(3) . . ? O1A C8 N1 118.6(4) . . ? O1B C8 N1 117.0(4) . . ? O1A C8 C4 116.5(4) . . ? O1B C8 C4 116.5(4) . . ? N1 C8 C4 123.7(3) . . ? O2A C9 O2B 27.9(5) . . ? O2A C9 N2 119.7(4) . . ? O2B C9 N2 116.5(5) . . ? O2A C9 C4 122.1(4) . . ? O2B C9 C4 122.3(5) . . ? N2 C9 C4 117.4(3) . . ? N1 C10 N3 117.2(3) . . ? N1 C10 N2 125.3(3) . . ? N3 C10 N2 117.5(3) . . ? O3 C11 N4 124.8(4) . . ? O3 C11 N3 121.2(4) . . ? N4 C11 N3 114.0(3) . . ? C13B C12 N4 121.6(8) . . ? C13B C12 C13A 25.1(8) . . ? N4 C12 C13A 111.9(6) . . ? C13B C12 H12A 120.2 . . ? N4 C12 H12A 109.2 . . ? C13A C12 H12A 109.2 . . ? C13B C12 H12B 84.2 . . ? N4 C12 H12B 109.2 . . ? C13A C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C14A C13A C12 113.7(10) . . ? C14A C13A C15 106.9(10) . . ? C12 C13A C15 106.3(9) . . ? C12 C13B C14B 123.7(14) . . ? C12 C13B C15 118.4(11) . . ? C14B C13B C15 114.4(13) . . ? C12 C13B H15C 112.7 . . ? C14B C13B H15C 97.2 . . ? C15 C13B H15C 37.5 . . ? C13B C14B H14D 109.5 . . ? C13B C14B H14E 109.5 . . ? H14D C14B H14E 109.5 . . ? C13B C14B H14F 109.5 . . ? H14D C14B H14F 109.5 . . ? H14E C14B H14F 109.5 . . ? C13B C15 C13A 23.6(7) . . ? C13B C15 H15A 124.6 . . ? C13A C15 H15A 116.5 . . ? C13B C15 H15B 125.2 . . ? C13A C15 H15B 119.2 . . ? H15A C15 H15B 107.9 . . ? C13B C15 H15C 72.5 . . ? C13A C15 H15C 96.1 . . ? H15A C15 H15C 107.9 . . ? H15B C15 H15C 107.8 . . ? C10 N1 C8 117.4(3) . . ? C10 N2 C9 123.1(3) . . ? C10 N2 H2N 120(3) . . ? C9 N2 H2N 117(3) . . ? C10 N3 C11 126.5(3) . . ? C10 N3 H3N 110(4) . . ? C11 N3 H3N 123(4) . . ? C11 N4 C12 121.5(4) . . ? C11 N4 H4N 114(5) . . ? C12 N4 H4N 124(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 C4 115.0(9) . . . . ? C2 C3 C4 C9 58.0(6) . . . . ? C2 C3 C4 C8 -65.1(6) . . . . ? C2 C3 C4 C5 175.5(5) . . . . ? C9 C4 C5 C6 -57.5(8) . . . . ? C8 C4 C5 C6 66.3(8) . . . . ? C3 C4 C5 C6 -175.0(7) . . . . ? C4 C5 C6 C7 -145(3) . . . . ? C9 C4 C8 O1A 159.3(7) . . . . ? C5 C4 C8 O1A 38.0(8) . . . . ? C3 C4 C8 O1A -80.0(8) . . . . ? C9 C4 C8 O1B -168.3(8) . . . . ? C5 C4 C8 O1B 70.3(9) . . . . ? C3 C4 C8 O1B -47.6(8) . . . . ? C9 C4 C8 N1 -7.8(7) . . . . ? C5 C4 C8 N1 -129.2(5) . . . . ? C3 C4 C8 N1 112.9(5) . . . . ? C8 C4 C9 O2A -163.4(7) . . . . ? C5 C4 C9 O2A -41.1(8) . . . . ? C3 C4 C9 O2A 75.8(8) . . . . ? C8 C4 C9 O2B 163.6(10) . . . . ? C5 C4 C9 O2B -74.2(11) . . . . ? C3 C4 C9 O2B 42.8(11) . . . . ? C8 C4 C9 N2 6.2(6) . . . . ? C5 C4 C9 N2 128.5(4) . . . . ? C3 C4 C9 N2 -114.6(5) . . . . ? C13B C12 C13A C14A -57.4(19) . . . . ? N4 C12 C13A C14A 60.9(12) . . . . ? C13B C12 C13A C15 59.9(19) . . . . ? N4 C12 C13A C15 178.2(7) . . . . ? N4 C12 C13B C14B 45(2) . . . . ? C13A C12 C13B C14B 118(3) . . . . ? N4 C12 C13B C15 -157.8(13) . . . . ? C13A C12 C13B C15 -84(3) . . . . ? C12 C13B C15 C13A 86(3) . . . . ? C14B C13B C15 C13A -114(3) . . . . ? C14A C13A C15 C13B 65(2) . . . . ? C12 C13A C15 C13B -56.6(19) . . . . ? N3 C10 N1 C8 177.3(4) . . . . ? N2 C10 N1 C8 -3.5(6) . . . . ? O1A C8 N1 C10 -160.4(7) . . . . ? O1B C8 N1 C10 166.9(8) . . . . ? C4 C8 N1 C10 6.5(6) . . . . ? N1 C10 N2 C9 2.5(6) . . . . ? N3 C10 N2 C9 -178.3(4) . . . . ? O2A C9 N2 C10 165.8(7) . . . . ? O2B C9 N2 C10 -162.7(10) . . . . ? C4 C9 N2 C10 -4.1(6) . . . . ? N1 C10 N3 C11 -172.0(4) . . . . ? N2 C10 N3 C11 8.7(6) . . . . ? O3 C11 N3 C10 -1.4(7) . . . . ? N4 C11 N3 C10 178.6(4) . . . . ? O3 C11 N4 C12 -1.5(9) . . . . ? N3 C11 N4 C12 178.5(5) . . . . ? C13B C12 N4 C11 131.5(14) . . . . ? C13A C12 N4 C11 105.5(8) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.471 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.055 data_beta_form _database_code_depnum_ccdc_archive 'CCDC 600451' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,6-Dioxo-5,5-diethylenepyrimidine-2-isobutylurea ; _chemical_name_common 4,6-Dioxo-5,5-diethylenepyrimidine-2-isobutylurea _chemical_melting_point ? _chemical_formula_moiety 'C15 H22 N4 O3' _chemical_formula_sum 'C15 H22 N4 O3' _chemical_formula_weight 306.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 13.6097(5) _cell_length_b 14.2030(5) _cell_length_c 17.5902(6) _cell_angle_alpha 91.320(2) _cell_angle_beta 95.043(2) _cell_angle_gamma 98.854(2) _cell_volume 3344.3(2) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7840 _cell_measurement_theta_min 2.267 _cell_measurement_theta_max 26.319 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.922048 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ; SADABS (Sheldrick, G. M. (1998)). Program for Absorption Correction. University of G\"ottingen, Germany. ; _exptl_special_details ; Data for the \a and \b form were collected on the same crystal. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD 6K area detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 30479 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.0655 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 25.00 _reflns_number_total 11726 _reflns_number_gt 7492 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART 1998' _computing_cell_refinement 'Bruker SMART 1998' _computing_data_reduction 'Bruker SAINT 1998' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0806P)^2^+1.0955P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0016(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 11726 _refine_ls_number_parameters 866 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1063 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1739 _refine_ls_wR_factor_gt 0.1558 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 N1 N 0.65308(16) 0.23335(15) 0.23558(13) 0.0328(6) Uani 1 1 d . . . N2 N 0.56843(17) 0.35152(17) 0.28645(14) 0.0335(6) Uani 1 1 d . . . H2N H 0.574(2) 0.406(2) 0.3117(19) 0.053(10) Uiso 1 1 d . . . N3 N 0.74192(18) 0.36790(16) 0.29490(14) 0.0312(6) Uani 1 1 d . . . H3N H 0.791(2) 0.342(2) 0.2857(18) 0.045(10) Uiso 1 1 d . . . N4 N 0.85482(19) 0.50206(17) 0.33354(15) 0.0356(6) Uani 1 1 d . . . H4N H 0.897(2) 0.472(2) 0.3245(18) 0.044(10) Uiso 1 1 d . . . N5 N 0.91672(15) 0.27148(14) 0.25692(13) 0.0284(5) Uani 1 1 d . . . N6 N 0.99651(16) 0.14736(17) 0.20942(14) 0.0320(6) Uani 1 1 d . . . H6N H 0.982(2) 0.090(2) 0.1884(19) 0.056(10) Uiso 1 1 d . . . N7 N 0.82476(17) 0.12844(16) 0.21536(13) 0.0294(5) Uani 1 1 d . . . H7N H 0.778(2) 0.1578(18) 0.2212(15) 0.024(7) Uiso 1 1 d . . . N8 N 0.71285(19) -0.00828(17) 0.18430(16) 0.0417(7) Uani 1 1 d . . . H8N H 0.673(2) 0.031(2) 0.1757(17) 0.043(9) Uiso 1 1 d . . . N9 N 0.21136(17) 0.79851(15) 0.16228(12) 0.0316(5) Uani 1 1 d . . . N10 N 0.12609(19) 0.92953(17) 0.18281(14) 0.0374(6) Uani 1 1 d . . . H10N H 0.120(2) 0.969(2) 0.2164(17) 0.034(8) Uiso 1 1 d . . . N11 N 0.21799(19) 0.86775(17) 0.28158(13) 0.0355(6) Uani 1 1 d . . . H11N H 0.253(2) 0.825(2) 0.2957(17) 0.043(9) Uiso 1 1 d . . . N12 N 0.2403(2) 0.91997(19) 0.40717(14) 0.0485(7) Uani 1 1 d . . . H12N H 0.283(3) 0.871(3) 0.414(2) 0.071(11) Uiso 1 1 d . . . N13 N 0.40086(18) 0.56627(17) 0.30376(14) 0.0331(6) Uani 1 1 d . C . H13N H 0.409(2) 0.523(2) 0.2696(18) 0.046(9) Uiso 1 1 d . . . N14 N 0.33594(17) 0.71095(15) 0.31991(12) 0.0321(5) Uani 1 1 d . C . N15 N 0.32187(18) 0.63604(16) 0.20240(13) 0.0305(5) Uani 1 1 d . C . H15N H 0.291(2) 0.6822(19) 0.1876(16) 0.032(8) Uiso 1 1 d . . . N16 N 0.31203(18) 0.58706(16) 0.07491(13) 0.0327(6) Uani 1 1 d . C . H16N H 0.275(2) 0.633(2) 0.0682(19) 0.055(10) Uiso 1 1 d . . . O1 O 0.56259(15) 0.10746(14) 0.16885(14) 0.0506(6) Uani 1 1 d . . . O2 O 0.40080(15) 0.34136(15) 0.27837(14) 0.0505(6) Uani 1 1 d . . . O3 O 0.68978(14) 0.50568(13) 0.33689(12) 0.0380(5) Uani 1 1 d . . . O4 O 1.01245(14) 0.40818(13) 0.30247(13) 0.0442(5) Uani 1 1 d . . . O5 O 1.16152(15) 0.16067(14) 0.19798(14) 0.0497(6) Uani 1 1 d . . . O6 O 0.87757(15) -0.01732(13) 0.20054(12) 0.0421(5) Uani 1 1 d . . . O7 O 0.20254(19) 0.73485(15) 0.04322(12) 0.0562(7) Uani 1 1 d . . . O8 O 0.03459(15) 0.99454(13) 0.09184(11) 0.0370(5) Uani 1 1 d . . . O9 O 0.14033(19) 0.99108(16) 0.32406(12) 0.0550(6) Uani 1 1 d . . . O10 O 0.48913(16) 0.50066(15) 0.39656(11) 0.0467(6) Uani 1 1 d . C . O11 O 0.36483(19) 0.78689(15) 0.43555(12) 0.0577(7) Uani 1 1 d . C . O12 O 0.38920(15) 0.50514(13) 0.16346(11) 0.0410(5) Uani 1 1 d . C . C1 C 0.4867(5) 0.0625(6) 0.3833(4) 0.153(3) Uani 1 1 d . . . H1A H 0.4831 0.0010 0.3599 0.184 Uiso 1 1 calc R . . H1B H 0.5152 0.0748 0.4346 0.184 Uiso 1 1 calc R . . C2 C 0.4551(4) 0.1254(3) 0.3479(3) 0.0967(17) Uani 1 1 d . . . H2 H 0.4625 0.1837 0.3770 0.116 Uiso 1 1 calc R . . C3 C 0.4079(2) 0.1320(2) 0.2706(2) 0.0516(9) Uani 1 1 d . . . H3A H 0.3390 0.1450 0.2743 0.062 Uiso 1 1 calc R . . H3B H 0.4030 0.0694 0.2434 0.062 Uiso 1 1 calc R . . C4 C 0.4630(2) 0.20980(19) 0.22195(18) 0.0382(7) Uani 1 1 d . . . C5 C 0.3994(2) 0.2138(2) 0.1449(2) 0.0479(8) Uani 1 1 d . . . H5A H 0.3911 0.1505 0.1183 0.057 Uiso 1 1 calc R . . H5B H 0.3322 0.2261 0.1556 0.057 Uiso 1 1 calc R . . C6 C 0.4414(3) 0.2875(2) 0.0922(2) 0.0568(10) Uani 1 1 d . . . H6 H 0.4478 0.3526 0.1085 0.068 Uiso 1 1 calc R . . C7 C 0.4695(3) 0.2686(3) 0.0258(2) 0.0756(12) Uani 1 1 d . . . H7A H 0.4640 0.2042 0.0078 0.091 Uiso 1 1 calc R . . H7B H 0.4956 0.3190 -0.0048 0.091 Uiso 1 1 calc R . . C8 C 0.5635(2) 0.1810(2) 0.20705(18) 0.0367(7) Uani 1 1 d . . . C9 C 0.4731(2) 0.3059(2) 0.26447(18) 0.0366(7) Uani 1 1 d . . . C10 C 0.65225(19) 0.31592(18) 0.27165(15) 0.0286(6) Uani 1 1 d . . . C11 C 0.7592(2) 0.46445(18) 0.32383(15) 0.0286(6) Uani 1 1 d . . . C12 C 0.8859(2) 0.60171(19) 0.35834(18) 0.0403(7) Uani 1 1 d . . . H12A H 0.9443 0.6061 0.3968 0.048 Uiso 1 1 calc R . . H12B H 0.8311 0.6241 0.3835 0.048 Uiso 1 1 calc R . . C13 C 0.9134(3) 0.6675(2) 0.2939(2) 0.0510(9) Uani 1 1 d . . . H13 H 0.862(2) 0.6567(18) 0.2574(16) 0.029(8) Uiso 1 1 d . . . C14 C 0.9320(3) 0.7714(2) 0.3227(3) 0.0786(13) Uani 1 1 d . . . H14A H 0.8725 0.7866 0.3449 0.118 Uiso 1 1 calc R . . H14B H 0.9466 0.8129 0.2800 0.118 Uiso 1 1 calc R . . H14C H 0.9890 0.7814 0.3617 0.118 Uiso 1 1 calc R . . C15 C 1.0034(3) 0.6425(3) 0.2575(2) 0.0747(12) Uani 1 1 d . . . H15A H 1.0612 0.6505 0.2958 0.112 Uiso 1 1 calc R . . H15B H 1.0179 0.6848 0.2153 0.112 Uiso 1 1 calc R . . H15C H 0.9893 0.5762 0.2380 0.112 Uiso 1 1 calc R . . C16 C 1.0835(3) 0.4496(3) 0.1087(2) 0.0700(11) Uani 1 1 d . . . H16A H 1.0832 0.5034 0.1417 0.084 Uiso 1 1 calc R . . H16B H 1.0555 0.4489 0.0573 0.084 Uiso 1 1 calc R . . C17 C 1.1225(2) 0.3767(2) 0.13411(19) 0.0500(8) Uani 1 1 d . . . H17 H 1.1213 0.3244 0.0992 0.060 Uiso 1 1 calc R . . C18 C 1.1685(2) 0.3685(2) 0.21271(17) 0.0374(7) Uani 1 1 d . . . H18A H 1.1768 0.4314 0.2399 0.045 Uiso 1 1 calc R . . H18B H 1.2358 0.3510 0.2100 0.045 Uiso 1 1 calc R . . C19 C 1.1654(2) 0.2858(2) 0.33840(18) 0.0429(8) Uani 1 1 d . . . H19A H 1.2301 0.2656 0.3298 0.051 Uiso 1 1 calc R . . H19B H 1.1799 0.3499 0.3640 0.051 Uiso 1 1 calc R . . C20 C 1.1130(3) 0.2181(2) 0.3906(2) 0.0546(9) Uani 1 1 d . . . H20 H 1.1013 0.1521 0.3763 0.065 Uiso 1 1 calc R . . C21 C 1.0826(4) 0.2440(3) 0.4543(2) 0.0870(14) Uani 1 1 d . . . H21A H 1.0932 0.3094 0.4702 0.104 Uiso 1 1 calc R . . H21B H 1.0496 0.1975 0.4853 0.104 Uiso 1 1 calc R . . C22 C 1.1064(2) 0.29343(19) 0.25946(16) 0.0324(7) Uani 1 1 d . . . C23 C 1.0082(2) 0.32760(19) 0.27322(16) 0.0324(6) Uani 1 1 d . . . C24 C 1.0928(2) 0.19633(19) 0.21911(17) 0.0336(7) Uani 1 1 d . . . C25 C 0.91506(18) 0.18428(17) 0.22806(15) 0.0254(6) Uani 1 1 d . . . C26 C 0.8084(2) 0.02817(19) 0.19911(16) 0.0314(6) Uani 1 1 d . . . C27 C 0.6824(3) -0.1102(2) 0.1668(2) 0.0525(9) Uani 1 1 d . A . H27A H 0.7429 -0.1409 0.1668 0.063 Uiso 1 1 calc R . . H27B H 0.6475 -0.1188 0.1147 0.063 Uiso 1 1 calc R . . C28 C 0.6152(3) -0.1597(2) 0.2216(2) 0.0534(9) Uani 1 1 d . . . C29A C 0.5304(8) -0.1243(7) 0.2429(9) 0.063(4) Uiso 0.409(15) 1 d P A 1 H29A H 0.5046 -0.1597 0.2860 0.094 Uiso 0.409(15) 1 calc PR A 1 H29B H 0.4790 -0.1320 0.1996 0.094 Uiso 0.409(15) 1 calc PR A 1 H29C H 0.5485 -0.0566 0.2579 0.094 Uiso 0.409(15) 1 calc PR A 1 C29B C 0.5065(5) -0.1326(5) 0.1985(5) 0.054(2) Uiso 0.591(15) 1 d P A 2 H29D H 0.4594 -0.1626 0.2331 0.082 Uiso 0.591(15) 1 calc PR A 2 H29E H 0.4839 -0.1555 0.1459 0.082 Uiso 0.591(15) 1 calc PR A 2 H29F H 0.5099 -0.0632 0.2022 0.082 Uiso 0.591(15) 1 calc PR A 2 C30 C 0.6054(3) -0.2676(2) 0.2098(2) 0.0667(11) Uani 1 1 d . A . H30A H 0.5695 -0.2869 0.1597 0.100 Uiso 1 1 calc R . . H30B H 0.5683 -0.2991 0.2499 0.100 Uiso 1 1 calc R . . H30C H 0.6720 -0.2861 0.2120 0.100 Uiso 1 1 calc R . . C31 C 0.3667(3) 0.9674(3) 0.0266(2) 0.0632(10) Uani 1 1 d . . . H31A H 0.3769 0.9159 -0.0057 0.076 Uiso 1 1 calc R . . H31B H 0.4223 1.0067 0.0535 0.076 Uiso 1 1 calc R . . C32 C 0.2764(2) 0.9842(2) 0.03398(19) 0.0446(8) Uani 1 1 d . . . H32 H 0.2693 1.0364 0.0668 0.053 Uiso 1 1 calc R . . C33 C 0.1831(2) 0.92755(19) -0.00534(16) 0.0341(7) Uani 1 1 d . . . H33A H 0.2015 0.8841 -0.0446 0.041 Uiso 1 1 calc R . . H33B H 0.1428 0.9716 -0.0317 0.041 Uiso 1 1 calc R . . C34 C 0.1182(2) 0.86774(18) 0.05062(15) 0.0311(6) Uani 1 1 d . . . C35 C 0.0230(2) 0.81386(19) 0.00466(16) 0.0346(7) Uani 1 1 d . . . H35A H -0.0151 0.8610 -0.0197 0.042 Uiso 1 1 calc R . . H35B H 0.0430 0.7742 -0.0365 0.042 Uiso 1 1 calc R . . C36 C -0.0431(3) 0.7518(2) 0.05219(18) 0.0481(8) Uani 1 1 d . . . H36 H -0.0185 0.6980 0.0733 0.058 Uiso 1 1 calc R . . C37 C -0.1314(3) 0.7651(3) 0.0671(3) 0.0845(14) Uani 1 1 d . . . H37A H -0.1586 0.8181 0.0471 0.101 Uiso 1 1 calc R . . H37B H -0.1690 0.7220 0.0981 0.101 Uiso 1 1 calc R . . C38 C 0.1802(2) 0.79588(19) 0.08581(16) 0.0354(7) Uani 1 1 d . . . H28 H 0.648(3) -0.140(3) 0.264(3) 0.092(16) Uiso 1 1 d . . . C39 C 0.0880(2) 0.93533(18) 0.10829(16) 0.0310(6) Uani 1 1 d . . . C40 C 0.1849(2) 0.86471(18) 0.20678(15) 0.0308(6) Uani 1 1 d . . . C41 C 0.1953(2) 0.9319(2) 0.33880(16) 0.0396(7) Uani 1 1 d . . . C42 C 0.2282(3) 0.9788(2) 0.47423(18) 0.0573(10) Uani 1 1 d . . . H42A H 0.2030 1.0372 0.4568 0.069 Uiso 1 1 calc R . . H42B H 0.2945 0.9987 0.5027 0.069 Uiso 1 1 calc R . . C43 C 0.1586(3) 0.9296(3) 0.5272(2) 0.0621(10) Uani 1 1 d . . . H43 H 0.092(3) 0.908(3) 0.494(2) 0.083(13) Uiso 1 1 d . . . C44 C 0.1948(4) 0.8422(3) 0.5607(2) 0.0844(14) Uani 1 1 d . . . H44A H 0.2022 0.7972 0.5193 0.127 Uiso 1 1 calc R . . H44B H 0.1461 0.8116 0.5940 0.127 Uiso 1 1 calc R . . H44C H 0.2594 0.8613 0.5906 0.127 Uiso 1 1 calc R . . C45 C 0.1384(4) 0.9982(3) 0.5900(2) 0.0891(15) Uani 1 1 d . . . H45A H 0.2009 1.0224 0.6210 0.134 Uiso 1 1 calc R . . H45B H 0.0906 0.9645 0.6225 0.134 Uiso 1 1 calc R . . H45C H 0.1105 1.0516 0.5669 0.134 Uiso 1 1 calc R . . C46 C 0.1559(3) 0.5542(3) 0.4594(3) 0.0783(12) Uani 1 1 d . . . H46A H 0.1474 0.5995 0.4979 0.094 Uiso 1 1 calc R . . H46B H 0.0992 0.5198 0.4301 0.094 Uiso 1 1 calc R . . C47 C 0.2461(3) 0.5391(2) 0.4468(2) 0.0548(9) Uani 1 1 d . . . H47 H 0.2507 0.4931 0.4077 0.066 Uiso 1 1 calc R . . C48 C 0.3411(2) 0.5867(2) 0.48755(17) 0.0404(7) Uani 1 1 d . . . H48A H 0.3723 0.5388 0.5170 0.048 Uiso 1 1 calc R . . H48B H 0.3261 0.6350 0.5245 0.048 Uiso 1 1 calc R . . C49 C 0.4180(2) 0.63663(19) 0.43443(16) 0.0338(7) Uani 1 1 d . C . C50 C 0.5144(2) 0.6786(2) 0.48442(18) 0.0497(9) Uani 1 1 d . . . H50A H 0.4956 0.7090 0.5311 0.060 Uiso 1 1 calc R B 1 H50B H 0.5500 0.6257 0.5005 0.060 Uiso 1 1 calc R B 1 C51A C 0.5823(5) 0.7480(6) 0.4480(4) 0.043(2) Uiso 0.487(8) 1 d P C 1 H51A H 0.5364 0.7617 0.4075 0.052 Uiso 0.487(8) 1 calc PR C 1 C51B C 0.6054(7) 0.7044(7) 0.4344(5) 0.067(3) Uiso 0.513(8) 1 d P C 2 H51B H 0.5785 0.6882 0.3833 0.081 Uiso 0.513(8) 1 calc PR C 2 C52A C 0.6451(8) 0.7946(8) 0.4333(6) 0.089(4) Uiso 0.487(8) 1 d P C 1 H52A H 0.7070 0.7988 0.4637 0.107 Uiso 0.487(8) 1 calc PR C 1 H52B H 0.6398 0.8324 0.3897 0.107 Uiso 0.487(8) 1 calc PR C 1 C52B C 0.6702(8) 0.7269(7) 0.4312(6) 0.084(3) Uiso 0.513(8) 1 d P C 2 H52C H 0.7126 0.7477 0.4762 0.100 Uiso 0.513(8) 1 calc PR C 2 H52D H 0.6964 0.7299 0.3829 0.100 Uiso 0.513(8) 1 calc PR C 2 C53 C 0.4406(2) 0.56241(19) 0.37844(16) 0.0326(7) Uani 1 1 d . . . C54 C 0.3718(2) 0.7165(2) 0.39543(17) 0.0371(7) Uani 1 1 d . . . C55 C 0.35290(19) 0.63857(18) 0.27765(15) 0.0272(6) Uani 1 1 d . . . C56 C 0.3437(2) 0.57094(18) 0.14613(15) 0.0286(6) Uani 1 1 d . . . C57 C 0.3286(2) 0.5217(2) 0.01335(16) 0.0371(7) Uani 1 1 d . . . H57A H 0.2917 0.4575 0.0214 0.044 Uiso 1 1 calc R C . H57B H 0.4006 0.5167 0.0160 0.044 Uiso 1 1 calc R . . C58 C 0.2957(2) 0.5526(2) -0.06592(16) 0.0370(7) Uani 1 1 d . C . H58 H 0.322(2) 0.620(2) -0.0682(15) 0.031(7) Uiso 1 1 d . . . C59 C 0.3350(3) 0.4899(2) -0.12427(18) 0.0526(9) Uani 1 1 d . . . H59A H 0.3084 0.4228 -0.1173 0.079 Uiso 1 1 calc R C . H59B H 0.4082 0.4990 -0.1169 0.079 Uiso 1 1 calc R . . H59C H 0.3138 0.5075 -0.1760 0.079 Uiso 1 1 calc R . . C60 C 0.1827(2) 0.5457(2) -0.07922(19) 0.0516(9) Uani 1 1 d . . . H60A H 0.1516 0.4788 -0.0779 0.077 Uiso 1 1 calc R C . H60B H 0.1651 0.5707 -0.1292 0.077 Uiso 1 1 calc R . . H60C H 0.1588 0.5830 -0.0392 0.077 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 N1 0.0251(13) 0.0286(12) 0.0443(15) -0.0065(11) 0.0045(11) 0.0038(10) N2 0.0277(13) 0.0299(13) 0.0432(15) -0.0071(11) 0.0056(11) 0.0055(10) N3 0.0259(13) 0.0272(12) 0.0409(15) -0.0051(10) 0.0027(11) 0.0071(10) N4 0.0287(14) 0.0305(13) 0.0472(16) -0.0093(11) 0.0056(12) 0.0042(11) N5 0.0238(12) 0.0266(12) 0.0343(13) -0.0035(10) 0.0036(10) 0.0027(9) N6 0.0236(13) 0.0279(13) 0.0446(15) -0.0081(11) 0.0042(10) 0.0053(10) N7 0.0217(13) 0.0285(12) 0.0389(14) -0.0041(10) 0.0066(10) 0.0058(10) N8 0.0299(15) 0.0281(13) 0.0662(19) -0.0093(12) 0.0103(13) 0.0001(11) N9 0.0440(14) 0.0265(12) 0.0249(13) 0.0000(10) -0.0035(11) 0.0117(10) N10 0.0560(17) 0.0357(14) 0.0253(14) -0.0048(11) -0.0026(12) 0.0265(12) N11 0.0529(16) 0.0338(13) 0.0233(14) 0.0009(10) -0.0030(11) 0.0211(12) N12 0.081(2) 0.0419(15) 0.0255(15) -0.0018(11) -0.0042(13) 0.0255(15) N13 0.0406(15) 0.0321(13) 0.0287(14) 0.0027(11) -0.0012(11) 0.0143(11) N14 0.0432(14) 0.0285(12) 0.0253(13) 0.0008(10) -0.0035(11) 0.0117(10) N15 0.0416(14) 0.0266(12) 0.0246(13) 0.0010(10) -0.0058(10) 0.0144(11) N16 0.0436(15) 0.0295(13) 0.0276(14) -0.0012(10) -0.0006(11) 0.0168(11) O1 0.0362(12) 0.0370(12) 0.0766(16) -0.0238(11) -0.0039(11) 0.0088(9) O2 0.0265(12) 0.0475(13) 0.0783(17) -0.0133(11) 0.0072(11) 0.0091(9) O3 0.0327(11) 0.0336(11) 0.0491(13) -0.0092(9) 0.0090(9) 0.0079(9) O4 0.0332(12) 0.0316(11) 0.0669(15) -0.0156(10) 0.0049(10) 0.0043(9) O5 0.0271(11) 0.0439(12) 0.0789(17) -0.0184(11) 0.0077(11) 0.0090(9) O6 0.0366(12) 0.0283(10) 0.0642(15) -0.0018(10) 0.0125(10) 0.0101(9) O7 0.0931(19) 0.0499(13) 0.0330(12) -0.0104(10) -0.0142(12) 0.0474(13) O8 0.0454(12) 0.0340(11) 0.0346(12) 0.0001(9) -0.0028(9) 0.0199(9) O9 0.0847(18) 0.0543(14) 0.0343(13) -0.0068(10) -0.0020(12) 0.0425(13) O10 0.0555(14) 0.0564(13) 0.0349(12) 0.0077(10) -0.0036(10) 0.0337(11) O11 0.098(2) 0.0437(13) 0.0333(13) -0.0071(10) -0.0122(12) 0.0301(12) O12 0.0546(13) 0.0386(11) 0.0343(12) -0.0004(9) -0.0015(10) 0.0249(10) C1 0.151(6) 0.191(8) 0.098(5) 0.031(5) -0.021(4) -0.018(5) C2 0.130(5) 0.066(3) 0.080(4) 0.018(3) -0.002(3) -0.026(3) C3 0.0393(19) 0.0431(18) 0.072(3) -0.0032(17) 0.0166(17) -0.0002(14) C4 0.0285(16) 0.0332(16) 0.053(2) -0.0040(14) 0.0045(14) 0.0039(12) C5 0.0265(16) 0.0470(19) 0.069(2) -0.0171(17) -0.0005(15) 0.0086(13) C6 0.059(2) 0.0414(19) 0.066(3) -0.0050(18) -0.0162(19) 0.0092(16) C7 0.089(3) 0.069(3) 0.061(3) -0.006(2) -0.003(2) -0.006(2) C8 0.0307(16) 0.0321(16) 0.0482(19) -0.0033(14) 0.0042(14) 0.0076(12) C9 0.0249(16) 0.0359(16) 0.0500(19) -0.0030(14) 0.0064(13) 0.0073(13) C10 0.0267(15) 0.0292(15) 0.0315(16) -0.0002(12) 0.0056(12) 0.0075(11) C11 0.0317(16) 0.0274(14) 0.0280(15) -0.0025(11) 0.0054(12) 0.0076(12) C12 0.0369(17) 0.0340(16) 0.0475(19) -0.0147(14) 0.0046(14) -0.0002(13) C13 0.064(2) 0.0371(18) 0.049(2) -0.0030(15) -0.0054(19) 0.0033(16) C14 0.094(3) 0.037(2) 0.107(4) -0.003(2) 0.031(3) 0.0029(19) C15 0.106(3) 0.053(2) 0.068(3) 0.0078(19) 0.042(2) 0.003(2) C16 0.053(2) 0.109(3) 0.054(2) 0.023(2) 0.0162(19) 0.023(2) C17 0.0403(19) 0.059(2) 0.047(2) -0.0024(17) 0.0085(16) -0.0046(16) C18 0.0270(16) 0.0361(16) 0.0476(19) -0.0058(14) 0.0057(13) -0.0003(12) C19 0.0355(17) 0.0446(18) 0.0479(19) -0.0077(15) -0.0035(14) 0.0094(14) C20 0.064(2) 0.046(2) 0.051(2) -0.0010(17) -0.0087(18) 0.0088(17) C21 0.114(4) 0.089(3) 0.052(3) 0.003(2) 0.009(3) -0.008(3) C22 0.0239(15) 0.0323(15) 0.0407(17) -0.0052(13) 0.0028(12) 0.0049(11) C23 0.0300(16) 0.0301(15) 0.0368(17) -0.0011(13) 0.0033(13) 0.0043(12) C24 0.0247(15) 0.0358(16) 0.0404(17) -0.0022(13) 0.0049(13) 0.0049(12) C25 0.0226(14) 0.0271(14) 0.0265(15) 0.0033(11) 0.0017(11) 0.0037(11) C26 0.0318(16) 0.0281(14) 0.0347(16) -0.0013(12) 0.0112(12) 0.0019(12) C27 0.047(2) 0.0361(17) 0.072(2) -0.0166(16) 0.0188(18) -0.0042(14) C28 0.065(2) 0.0337(18) 0.063(3) 0.0007(17) 0.020(2) 0.0038(16) C30 0.063(2) 0.0387(19) 0.099(3) 0.0016(19) 0.022(2) 0.0026(17) C31 0.045(2) 0.063(2) 0.079(3) -0.017(2) 0.0063(19) 0.0055(17) C32 0.043(2) 0.0413(18) 0.049(2) -0.0027(15) 0.0057(15) 0.0061(14) C33 0.0394(17) 0.0309(15) 0.0336(17) 0.0022(12) 0.0033(13) 0.0110(12) C34 0.0413(17) 0.0257(14) 0.0275(15) -0.0011(11) -0.0029(13) 0.0125(12) C35 0.0422(17) 0.0284(14) 0.0324(16) 0.0014(12) -0.0009(13) 0.0052(12) C36 0.065(2) 0.0327(17) 0.044(2) 0.0003(14) 0.0056(17) -0.0008(15) C37 0.090(3) 0.058(2) 0.112(4) 0.000(2) 0.054(3) 0.008(2) C38 0.0461(18) 0.0304(15) 0.0311(17) -0.0024(13) -0.0031(13) 0.0153(13) C39 0.0358(16) 0.0272(14) 0.0301(16) 0.0009(12) -0.0045(12) 0.0096(12) C40 0.0406(17) 0.0258(14) 0.0270(16) 0.0023(12) 0.0002(13) 0.0094(12) C41 0.061(2) 0.0332(16) 0.0273(17) 0.0007(13) 0.0030(14) 0.0156(15) C42 0.095(3) 0.049(2) 0.0292(18) -0.0081(15) -0.0027(18) 0.0236(19) C43 0.082(3) 0.064(2) 0.045(2) -0.0030(18) 0.016(2) 0.021(2) C44 0.110(4) 0.086(3) 0.069(3) 0.025(2) 0.036(3) 0.033(3) C45 0.124(4) 0.098(3) 0.059(3) -0.006(2) 0.032(3) 0.047(3) C46 0.055(3) 0.089(3) 0.087(3) 0.010(2) -0.006(2) 0.006(2) C47 0.061(2) 0.050(2) 0.052(2) 0.0025(16) 0.0095(18) 0.0030(17) C48 0.0461(19) 0.0445(17) 0.0344(17) 0.0063(14) 0.0067(14) 0.0166(14) C49 0.0418(17) 0.0339(15) 0.0260(15) 0.0054(12) -0.0006(13) 0.0086(13) C50 0.055(2) 0.054(2) 0.0354(19) 0.0035(15) -0.0138(16) 0.0034(16) C53 0.0343(16) 0.0349(16) 0.0291(16) 0.0085(12) 0.0000(13) 0.0074(13) C54 0.0491(19) 0.0292(15) 0.0323(17) 0.0024(13) -0.0013(14) 0.0067(13) C55 0.0279(15) 0.0281(14) 0.0262(15) 0.0051(12) 0.0018(12) 0.0056(11) C56 0.0317(15) 0.0262(14) 0.0286(16) 0.0022(12) 0.0002(12) 0.0075(12) C57 0.0483(19) 0.0344(16) 0.0312(17) -0.0041(13) 0.0036(14) 0.0160(13) C58 0.0445(18) 0.0363(17) 0.0312(17) 0.0003(13) 0.0060(14) 0.0083(14) C59 0.066(2) 0.060(2) 0.0350(19) -0.0048(16) 0.0113(16) 0.0172(17) C60 0.055(2) 0.059(2) 0.042(2) -0.0086(16) -0.0049(16) 0.0176(17) _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 C10 1.322(3) . ? N1 C8 1.373(4) . ? N2 C10 1.360(3) . ? N2 C9 1.376(4) . ? N2 H2N 0.87(3) . ? N3 C10 1.350(3) . ? N3 C11 1.429(3) . ? N3 H3N 0.84(3) . ? N4 C11 1.323(4) . ? N4 C12 1.458(4) . ? N4 H4N 0.79(3) . ? N5 C25 1.324(3) . ? N5 C23 1.374(3) . ? N6 C25 1.359(3) . ? N6 C24 1.380(4) . ? N6 H6N 0.87(3) . ? N7 C25 1.354(3) . ? N7 C26 1.425(3) . ? N7 H7N 0.82(3) . ? N8 C26 1.324(4) . ? N8 C27 1.461(4) . ? N8 H8N 0.84(3) . ? N9 C40 1.322(3) . ? N9 C38 1.372(3) . ? N10 C40 1.361(3) . ? N10 C39 1.376(4) . ? N10 H10N 0.82(3) . ? N11 C40 1.350(3) . ? N11 C41 1.427(4) . ? N11 H11N 0.86(3) . ? N12 C41 1.328(4) . ? N12 C42 1.466(4) . ? N12 H12N 0.97(4) . ? N13 C55 1.366(3) . ? N13 C53 1.382(3) . ? N13 H13N 0.88(3) . ? N14 C55 1.316(3) . ? N14 C54 1.371(4) . ? N15 C55 1.351(3) . ? N15 C56 1.420(3) . ? N15 H15N 0.87(3) . ? N16 C56 1.325(3) . ? N16 C57 1.465(3) . ? N16 H16N 0.88(3) . ? O1 C8 1.227(3) . ? O2 C9 1.213(3) . ? O3 C11 1.221(3) . ? O4 C23 1.235(3) . ? O5 C24 1.212(3) . ? O6 C26 1.220(3) . ? O7 C38 1.223(3) . ? O8 C39 1.217(3) . ? O9 C41 1.226(3) . ? O10 C53 1.209(3) . ? O11 C54 1.231(3) . ? O12 C56 1.228(3) . ? C1 C2 1.211(7) . ? C1 H1A 0.9500 . ? C1 H1B 0.9500 . ? C2 C3 1.464(6) . ? C2 H2 0.9500 . ? C3 C4 1.555(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C9 1.523(4) . ? C4 C8 1.529(4) . ? C4 C5 1.550(4) . ? C5 C6 1.494(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.296(5) . ? C6 H6 0.9500 . ? C7 H7A 0.9500 . ? C7 H7B 0.9500 . ? C12 C13 1.521(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C15 1.516(5) . ? C13 C14 1.524(5) . ? C13 H13 0.90(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.305(5) . ? C16 H16A 0.9500 . ? C16 H16B 0.9500 . ? C17 C18 1.482(4) . ? C17 H17 0.9500 . ? C18 C22 1.553(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.491(5) . ? C19 C22 1.556(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.293(5) . ? C20 H20 0.9500 . ? C21 H21A 0.9500 . ? C21 H21B 0.9500 . ? C22 C24 1.514(4) . ? C22 C23 1.527(4) . ? C27 C28 1.500(5) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29A 1.404(10) . ? C28 C30 1.525(4) . ? C28 C29B 1.606(8) . ? C28 H28 0.85(4) . ? C29A H29A 0.9800 . ? C29A H29B 0.9800 . ? C29A H29C 0.9800 . ? C29B H29D 0.9800 . ? C29B H29E 0.9800 . ? C29B H29F 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C32 1.305(5) . ? C31 H31A 0.9500 . ? C31 H31B 0.9500 . ? C32 C33 1.499(4) . ? C32 H32 0.9500 . ? C33 C34 1.559(4) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C39 1.506(4) . ? C34 C38 1.530(4) . ? C34 C35 1.549(4) . ? C35 C36 1.486(4) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.293(5) . ? C36 H36 0.9500 . ? C37 H37A 0.9500 . ? C37 H37B 0.9500 . ? C42 C43 1.495(5) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.517(5) . ? C43 C45 1.527(5) . ? C43 H43 1.04(4) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 C47 1.314(5) . ? C46 H46A 0.9500 . ? C46 H46B 0.9500 . ? C47 C48 1.480(5) . ? C47 H47 0.9500 . ? C48 C49 1.564(4) . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C49 C53 1.511(4) . ? C49 C54 1.527(4) . ? C49 C50 1.544(4) . ? C50 C51A 1.445(8) . ? C50 C51B 1.584(11) . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C51A C52A 1.052(11) . ? C51A H51A 0.9500 . ? C51B C52B 0.898(11) . ? C51B H51B 0.9500 . ? C52A H52A 0.9500 . ? C52A H52B 0.9500 . ? C52B H52C 0.9500 . ? C52B H52D 0.9500 . ? C57 C58 1.522(4) . ? C57 H57A 0.9900 . ? C57 H57B 0.9900 . ? C58 C60 1.522(4) . ? C58 C59 1.528(4) . ? C58 H58 0.97(3) . ? C59 H59A 0.9800 . ? C59 H59B 0.9800 . ? C59 H59C 0.9800 . ? C60 H60A 0.9800 . ? C60 H60B 0.9800 . ? C60 H60C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 N1 C8 118.5(2) . . ? C10 N2 C9 123.7(2) . . ? C10 N2 H2N 119(2) . . ? C9 N2 H2N 117(2) . . ? C10 N3 C11 126.2(2) . . ? C10 N3 H3N 114(2) . . ? C11 N3 H3N 119(2) . . ? C11 N4 C12 121.1(2) . . ? C11 N4 H4N 121(2) . . ? C12 N4 H4N 118(2) . . ? C25 N5 C23 117.8(2) . . ? C25 N6 C24 124.0(2) . . ? C25 N6 H6N 113(2) . . ? C24 N6 H6N 123(2) . . ? C25 N7 C26 125.6(2) . . ? C25 N7 H7N 112.6(19) . . ? C26 N7 H7N 121.7(19) . . ? C26 N8 C27 120.8(3) . . ? C26 N8 H8N 116(2) . . ? C27 N8 H8N 122(2) . . ? C40 N9 C38 118.3(2) . . ? C40 N10 C39 123.9(2) . . ? C40 N10 H10N 114(2) . . ? C39 N10 H10N 122(2) . . ? C40 N11 C41 125.9(2) . . ? C40 N11 H11N 116(2) . . ? C41 N11 H11N 118(2) . . ? C41 N12 C42 121.9(3) . . ? C41 N12 H12N 120(2) . . ? C42 N12 H12N 118(2) . . ? C55 N13 C53 123.4(2) . . ? C55 N13 H13N 116(2) . . ? C53 N13 H13N 120(2) . . ? C55 N14 C54 117.9(2) . . ? C55 N15 C56 126.0(2) . . ? C55 N15 H15N 115.3(18) . . ? C56 N15 H15N 118.4(18) . . ? C56 N16 C57 119.0(2) . . ? C56 N16 H16N 117(2) . . ? C57 N16 H16N 124(2) . . ? C2 C1 H1A 120.0 . . ? C2 C1 H1B 120.0 . . ? H1A C1 H1B 120.0 . . ? C1 C2 C3 134.6(6) . . ? C1 C2 H2 112.7 . . ? C3 C2 H2 112.7 . . ? C2 C3 C4 115.0(3) . . ? 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 . . ? C9 C4 C8 113.1(2) . . ? C9 C4 C5 108.8(2) . . ? C8 C4 C5 109.4(3) . . ? C9 C4 C3 108.7(3) . . ? C8 C4 C3 107.9(2) . . ? C5 C4 C3 108.8(2) . . ? C6 C5 C4 115.2(3) . . ? 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 . . ? C7 C6 C5 124.4(3) . . ? C7 C6 H6 117.8 . . ? C5 C6 H6 117.8 . . ? C6 C7 H7A 120.0 . . ? C6 C7 H7B 120.0 . . ? H7A C7 H7B 120.0 . . ? O1 C8 N1 119.7(3) . . ? O1 C8 C4 117.7(2) . . ? N1 C8 C4 122.6(2) . . ? O2 C9 N2 121.1(3) . . ? O2 C9 C4 121.9(3) . . ? N2 C9 C4 117.1(2) . . ? N1 C10 N3 116.7(2) . . ? N1 C10 N2 124.8(2) . . ? N3 C10 N2 118.4(2) . . ? O3 C11 N4 125.3(2) . . ? O3 C11 N3 121.0(2) . . ? N4 C11 N3 113.6(2) . . ? N4 C12 C13 113.9(3) . . ? N4 C12 H12A 108.8 . . ? C13 C12 H12A 108.8 . . ? N4 C12 H12B 108.8 . . ? C13 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C15 C13 C12 111.4(3) . . ? C15 C13 C14 110.7(3) . . ? C12 C13 C14 110.6(3) . . ? C15 C13 H13 105.9(18) . . ? C12 C13 H13 106.9(18) . . ? C14 C13 H13 111.3(17) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 H16A 120.0 . . ? C17 C16 H16B 120.0 . . ? H16A C16 H16B 120.0 . . ? C16 C17 C18 125.6(3) . . ? C16 C17 H17 117.2 . . ? C18 C17 H17 117.2 . . ? C17 C18 C22 113.4(2) . . ? C17 C18 H18A 108.9 . . ? C22 C18 H18A 108.9 . . ? C17 C18 H18B 108.9 . . ? C22 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? C20 C19 C22 114.7(2) . . ? C20 C19 H19A 108.6 . . ? C22 C19 H19A 108.6 . . ? C20 C19 H19B 108.6 . . ? C22 C19 H19B 108.6 . . ? H19A C19 H19B 107.6 . . ? C21 C20 C19 123.8(3) . . ? C21 C20 H20 118.1 . . ? C19 C20 H20 118.1 . . ? C20 C21 H21A 120.0 . . ? C20 C21 H21B 120.0 . . ? H21A C21 H21B 120.0 . . ? C24 C22 C23 113.6(2) . . ? C24 C22 C18 109.9(2) . . ? C23 C22 C18 108.9(2) . . ? C24 C22 C19 107.3(2) . . ? C23 C22 C19 108.2(2) . . ? C18 C22 C19 108.8(2) . . ? O4 C23 N5 119.3(2) . . ? O4 C23 C22 117.8(2) . . ? N5 C23 C22 122.8(2) . . ? O5 C24 N6 120.5(3) . . ? O5 C24 C22 123.2(2) . . ? N6 C24 C22 116.2(2) . . ? N5 C25 N7 117.1(2) . . ? N5 C25 N6 125.1(2) . . ? N7 C25 N6 117.9(2) . . ? O6 C26 N8 125.1(3) . . ? O6 C26 N7 121.5(3) . . ? N8 C26 N7 113.4(2) . . ? N8 C27 C28 114.0(3) . . ? N8 C27 H27A 108.8 . . ? C28 C27 H27A 108.8 . . ? N8 C27 H27B 108.8 . . ? C28 C27 H27B 108.8 . . ? H27A C27 H27B 107.7 . . ? C29A C28 C27 122.4(5) . . ? C29A C28 C30 116.6(5) . . ? C27 C28 C30 110.3(3) . . ? C29A C28 C29B 30.6(5) . . ? C27 C28 C29B 105.9(4) . . ? C30 C28 C29B 106.4(4) . . ? C29A C28 H28 91(3) . . ? C27 C28 H28 101(3) . . ? C30 C28 H28 112(3) . . ? C29B C28 H28 121(3) . . ? C28 C29A H29A 109.5 . . ? C28 C29A H29B 109.5 . . ? C28 C29A H29C 109.5 . . ? C28 C29B H29D 109.5 . . ? C28 C29B H29E 109.5 . . ? H29D C29B H29E 109.5 . . ? C28 C29B H29F 109.5 . . ? H29D C29B H29F 109.5 . . ? H29E C29B H29F 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C32 C31 H31A 120.0 . . ? C32 C31 H31B 120.0 . . ? H31A C31 H31B 120.0 . . ? C31 C32 C33 124.9(3) . . ? C31 C32 H32 117.5 . . ? C33 C32 H32 117.5 . . ? C32 C33 C34 112.9(2) . . ? C32 C33 H33A 109.0 . . ? C34 C33 H33A 109.0 . . ? C32 C33 H33B 109.0 . . ? C34 C33 H33B 109.0 . . ? H33A C33 H33B 107.8 . . ? C39 C34 C38 113.8(2) . . ? C39 C34 C35 109.0(2) . . ? C38 C34 C35 109.6(2) . . ? C39 C34 C33 108.2(2) . . ? C38 C34 C33 107.4(2) . . ? C35 C34 C33 108.7(2) . . ? C36 C35 C34 113.3(2) . . ? C36 C35 H35A 108.9 . . ? C34 C35 H35A 108.9 . . ? C36 C35 H35B 108.9 . . ? C34 C35 H35B 108.9 . . ? H35A C35 H35B 107.7 . . ? C37 C36 C35 125.2(3) . . ? C37 C36 H36 117.4 . . ? C35 C36 H36 117.4 . . ? C36 C37 H37A 120.0 . . ? C36 C37 H37B 120.0 . . ? H37A C37 H37B 120.0 . . ? O7 C38 N9 119.9(2) . . ? O7 C38 C34 117.8(2) . . ? N9 C38 C34 122.3(2) . . ? O8 C39 N10 119.7(3) . . ? O8 C39 C34 123.6(2) . . ? N10 C39 C34 116.7(2) . . ? N9 C40 N11 117.6(2) . . ? N9 C40 N10 124.7(2) . . ? N11 C40 N10 117.6(2) . . ? O9 C41 N12 125.4(3) . . ? O9 C41 N11 122.0(3) . . ? N12 C41 N11 112.7(2) . . ? N12 C42 C43 114.0(3) . . ? N12 C42 H42A 108.8 . . ? C43 C42 H42A 108.8 . . ? N12 C42 H42B 108.8 . . ? C43 C42 H42B 108.8 . . ? H42A C42 H42B 107.7 . . ? C42 C43 C44 112.5(3) . . ? C42 C43 C45 111.5(3) . . ? C44 C43 C45 111.1(3) . . ? C42 C43 H43 105(2) . . ? C44 C43 H43 108(2) . . ? C45 C43 H43 108(2) . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C43 C45 H45A 109.5 . . ? C43 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C43 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C47 C46 H46A 120.0 . . ? C47 C46 H46B 120.0 . . ? H46A C46 H46B 120.0 . . ? C46 C47 C48 126.3(4) . . ? C46 C47 H47 116.9 . . ? C48 C47 H47 116.9 . . ? C47 C48 C49 114.4(3) . . ? C47 C48 H48A 108.7 . . ? C49 C48 H48A 108.7 . . ? C47 C48 H48B 108.7 . . ? C49 C48 H48B 108.7 . . ? H48A C48 H48B 107.6 . . ? C53 C49 C54 112.9(2) . . ? C53 C49 C50 109.6(2) . . ? C54 C49 C50 110.0(2) . . ? C53 C49 C48 108.3(2) . . ? C54 C49 C48 107.6(2) . . ? C50 C49 C48 108.4(2) . . ? C51A C50 C49 115.1(4) . . ? C51A C50 C51B 29.4(3) . . ? C49 C50 C51B 111.4(4) . . ? C51A C50 H50A 108.5 . . ? C49 C50 H50A 108.5 . . ? C51B C50 H50A 132.4 . . ? C51A C50 H50B 108.5 . . ? C49 C50 H50B 108.5 . . ? C51B C50 H50B 83.3 . . ? H50A C50 H50B 107.5 . . ? C52A C51A C50 164.9(9) . . ? C52A C51A H51A 97.5 . . ? C50 C51A H51A 97.5 . . ? C52B C51B C50 149.9(12) . . ? C52B C51B H51B 105.1 . . ? C50 C51B H51B 105.1 . . ? C51A C52A H52A 120.0 . . ? C51A C52A H52B 120.0 . . ? H52A C52A H52B 120.0 . . ? C51B C52B H52C 120.0 . . ? C51B C52B H52D 120.0 . . ? H52C C52B H52D 120.0 . . ? O10 C53 N13 120.1(3) . . ? O10 C53 C49 123.2(3) . . ? N13 C53 C49 116.7(2) . . ? O11 C54 N14 120.0(2) . . ? O11 C54 C49 117.0(3) . . ? N14 C54 C49 122.9(2) . . ? N14 C55 N15 117.7(2) . . ? N14 C55 N13 125.0(2) . . ? N15 C55 N13 117.3(2) . . ? O12 C56 N16 123.4(3) . . ? O12 C56 N15 121.4(2) . . ? N16 C56 N15 115.2(2) . . ? N16 C57 C58 113.5(2) . . ? N16 C57 H57A 108.9 . . ? C58 C57 H57A 108.9 . . ? N16 C57 H57B 108.9 . . ? C58 C57 H57B 108.9 . . ? H57A C57 H57B 107.7 . . ? C57 C58 C60 112.1(3) . . ? C57 C58 C59 107.8(2) . . ? C60 C58 C59 111.0(3) . . ? C57 C58 H58 106.8(16) . . ? C60 C58 H58 105.9(16) . . ? C59 C58 H58 113.2(16) . . ? C58 C59 H59A 109.5 . . ? C58 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C58 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? C58 C60 H60A 109.5 . . ? C58 C60 H60B 109.5 . . ? H60A C60 H60B 109.5 . . ? C58 C60 H60C 109.5 . . ? H60A C60 H60C 109.5 . . ? H60B C60 H60C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 C4 -122.3(7) . . . . ? C2 C3 C4 C9 -56.8(4) . . . . ? C2 C3 C4 C8 66.3(4) . . . . ? C2 C3 C4 C5 -175.1(3) . . . . ? C9 C4 C5 C6 60.2(3) . . . . ? C8 C4 C5 C6 -63.9(3) . . . . ? C3 C4 C5 C6 178.4(3) . . . . ? C4 C5 C6 C7 116.3(4) . . . . ? C10 N1 C8 O1 175.0(3) . . . . ? C10 N1 C8 C4 -6.0(4) . . . . ? C9 C4 C8 O1 -175.5(3) . . . . ? C5 C4 C8 O1 -54.0(4) . . . . ? C3 C4 C8 O1 64.2(4) . . . . ? C9 C4 C8 N1 5.5(4) . . . . ? C5 C4 C8 N1 127.0(3) . . . . ? C3 C4 C8 N1 -114.8(3) . . . . ? C10 N2 C9 O2 -179.1(3) . . . . ? C10 N2 C9 C4 0.6(4) . . . . ? C8 C4 C9 O2 177.1(3) . . . . ? C5 C4 C9 O2 55.3(4) . . . . ? C3 C4 C9 O2 -63.0(4) . . . . ? C8 C4 C9 N2 -2.7(4) . . . . ? C5 C4 C9 N2 -124.5(3) . . . . ? C3 C4 C9 N2 117.2(3) . . . . ? C8 N1 C10 N3 -176.2(3) . . . . ? C8 N1 C10 N2 3.6(4) . . . . ? C11 N3 C10 N1 169.6(2) . . . . ? C11 N3 C10 N2 -10.2(4) . . . . ? C9 N2 C10 N1 -0.9(4) . . . . ? C9 N2 C10 N3 178.9(3) . . . . ? C12 N4 C11 O3 -3.1(4) . . . . ? C12 N4 C11 N3 176.3(2) . . . . ? C10 N3 C11 O3 7.4(4) . . . . ? C10 N3 C11 N4 -172.1(3) . . . . ? C11 N4 C12 C13 -100.5(3) . . . . ? N4 C12 C13 C15 -63.7(4) . . . . ? N4 C12 C13 C14 172.8(3) . . . . ? C16 C17 C18 C22 110.6(4) . . . . ? C22 C19 C20 C21 -114.3(4) . . . . ? C17 C18 C22 C24 58.7(3) . . . . ? C17 C18 C22 C23 -66.4(3) . . . . ? C17 C18 C22 C19 175.9(2) . . . . ? C20 C19 C22 C24 -62.9(3) . . . . ? C20 C19 C22 C23 60.1(3) . . . . ? C20 C19 C22 C18 178.2(3) . . . . ? C25 N5 C23 O4 -177.7(3) . . . . ? C25 N5 C23 C22 0.0(4) . . . . ? C24 C22 C23 O4 -176.5(3) . . . . ? C18 C22 C23 O4 -53.6(3) . . . . ? C19 C22 C23 O4 64.4(3) . . . . ? C24 C22 C23 N5 5.8(4) . . . . ? C18 C22 C23 N5 128.7(3) . . . . ? C19 C22 C23 N5 -113.3(3) . . . . ? C25 N6 C24 O5 -176.6(3) . . . . ? C25 N6 C24 C22 5.5(4) . . . . ? C23 C22 C24 O5 174.1(3) . . . . ? C18 C22 C24 O5 51.8(4) . . . . ? C19 C22 C24 O5 -66.4(4) . . . . ? C23 C22 C24 N6 -8.1(4) . . . . ? C18 C22 C24 N6 -130.4(3) . . . . ? C19 C22 C24 N6 111.4(3) . . . . ? C23 N5 C25 N7 177.2(2) . . . . ? C23 N5 C25 N6 -3.7(4) . . . . ? C26 N7 C25 N5 -167.0(2) . . . . ? C26 N7 C25 N6 13.8(4) . . . . ? C24 N6 C25 N5 0.8(4) . . . . ? C24 N6 C25 N7 179.8(3) . . . . ? C27 N8 C26 O6 -0.9(5) . . . . ? C27 N8 C26 N7 -179.7(3) . . . . ? C25 N7 C26 O6 5.1(4) . . . . ? C25 N7 C26 N8 -176.0(3) . . . . ? C26 N8 C27 C28 119.7(4) . . . . ? N8 C27 C28 C29A 49.0(9) . . . . ? N8 C27 C28 C30 -167.9(3) . . . . ? N8 C27 C28 C29B 77.4(5) . . . . ? C31 C32 C33 C34 110.7(4) . . . . ? C32 C33 C34 C39 60.6(3) . . . . ? C32 C33 C34 C38 -62.7(3) . . . . ? C32 C33 C34 C35 178.8(2) . . . . ? C39 C34 C35 C36 -64.1(3) . . . . ? C38 C34 C35 C36 61.0(3) . . . . ? C33 C34 C35 C36 178.1(2) . . . . ? C34 C35 C36 C37 113.1(4) . . . . ? C40 N9 C38 O7 -179.3(3) . . . . ? C40 N9 C38 C34 1.3(4) . . . . ? C39 C34 C38 O7 175.7(3) . . . . ? C35 C34 C38 O7 53.5(4) . . . . ? C33 C34 C38 O7 -64.5(3) . . . . ? C39 C34 C38 N9 -4.8(4) . . . . ? C35 C34 C38 N9 -127.1(3) . . . . ? C33 C34 C38 N9 115.0(3) . . . . ? C40 N10 C39 O8 178.8(3) . . . . ? C40 N10 C39 C34 -2.7(4) . . . . ? C38 C34 C39 O8 -176.4(3) . . . . ? C35 C34 C39 O8 -53.7(3) . . . . ? C33 C34 C39 O8 64.3(3) . . . . ? C38 C34 C39 N10 5.2(4) . . . . ? C35 C34 C39 N10 127.9(3) . . . . ? C33 C34 C39 N10 -114.1(3) . . . . ? C38 N9 C40 N11 -178.6(3) . . . . ? C38 N9 C40 N10 2.0(4) . . . . ? C41 N11 C40 N9 -178.1(3) . . . . ? C41 N11 C40 N10 1.4(4) . . . . ? C39 N10 C40 N9 -1.2(5) . . . . ? C39 N10 C40 N11 179.3(3) . . . . ? C42 N12 C41 O9 0.0(5) . . . . ? C42 N12 C41 N11 179.5(3) . . . . ? C40 N11 C41 O9 1.0(5) . . . . ? C40 N11 C41 N12 -178.4(3) . . . . ? C41 N12 C42 C43 103.0(4) . . . . ? N12 C42 C43 C44 61.9(5) . . . . ? N12 C42 C43 C45 -172.5(3) . . . . ? C46 C47 C48 C49 -124.7(4) . . . . ? C47 C48 C49 C53 -58.6(3) . . . . ? C47 C48 C49 C54 63.7(3) . . . . ? C47 C48 C49 C50 -177.4(3) . . . . ? C53 C49 C50 C51A 77.8(5) . . . . ? C54 C49 C50 C51A -46.9(5) . . . . ? C48 C49 C50 C51A -164.2(4) . . . . ? C53 C49 C50 C51B 46.0(5) . . . . ? C54 C49 C50 C51B -78.6(5) . . . . ? C48 C49 C50 C51B 164.0(4) . . . . ? C49 C50 C51A C52A -163(4) . . . . ? C51B C50 C51A C52A -73(4) . . . . ? C51A C50 C51B C52B 77(2) . . . . ? C49 C50 C51B C52B -179(2) . . . . ? C55 N13 C53 O10 -174.0(3) . . . . ? C55 N13 C53 C49 7.4(4) . . . . ? C54 C49 C53 O10 169.8(3) . . . . ? C50 C49 C53 O10 46.8(4) . . . . ? C48 C49 C53 O10 -71.2(3) . . . . ? C54 C49 C53 N13 -11.7(4) . . . . ? C50 C49 C53 N13 -134.7(3) . . . . ? C48 C49 C53 N13 107.3(3) . . . . ? C55 N14 C54 O11 174.1(3) . . . . ? C55 N14 C54 C49 -8.2(4) . . . . ? C53 C49 C54 O11 -169.4(3) . . . . ? C50 C49 C54 O11 -46.7(4) . . . . ? C48 C49 C54 O11 71.2(3) . . . . ? C53 C49 C54 N14 12.8(4) . . . . ? C50 C49 C54 N14 135.5(3) . . . . ? C48 C49 C54 N14 -106.6(3) . . . . ? C54 N14 C55 N15 -176.7(2) . . . . ? C54 N14 C55 N13 2.3(4) . . . . ? C56 N15 C55 N14 171.9(2) . . . . ? C56 N15 C55 N13 -7.2(4) . . . . ? C53 N13 C55 N14 -2.2(4) . . . . ? C53 N13 C55 N15 176.8(2) . . . . ? C57 N16 C56 O12 2.2(4) . . . . ? C57 N16 C56 N15 -178.2(2) . . . . ? C55 N15 C56 O12 5.0(4) . . . . ? C55 N15 C56 N16 -174.6(3) . . . . ? C56 N16 C57 C58 -175.7(3) . . . . ? N16 C57 C58 C60 -68.3(3) . . . . ? N16 C57 C58 C59 169.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.327 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.047 data_gamma_form _database_code_depnum_ccdc_archive 'CCDC 600452' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,6-Dioxo-5,5-diethylenepyrimidine-2-isobutylurea ; _chemical_name_common 4,6-Dioxo-5,5-diethylenepyrimidine-2-isobutylurea _chemical_melting_point ? _chemical_formula_moiety 'C15 H21 N4 O3, (C15 H22 N4 O3)2' _chemical_formula_sum 'C15 H21.67 N4 O3' _chemical_formula_weight 306.03 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 12.0670(6) _cell_length_b 13.8660(7) _cell_length_c 17.6218(9) _cell_angle_alpha 73.608(2) _cell_angle_beta 71.557(2) _cell_angle_gamma 66.840(2) _cell_volume 2529.2(2) _cell_formula_units_Z 6 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3394 _cell_measurement_theta_min 2.214 _cell_measurement_theta_max 22.609 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 982 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.891717 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ; SADABS (Sheldrick, G. M. (1998)). Program for Absorption Correction. University of G\"ottingen, Germany. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD 1K area detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22398 _diffrn_reflns_av_R_equivalents 0.0778 _diffrn_reflns_av_sigmaI/netI 0.1205 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8896 _reflns_number_gt 4049 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART 1998' _computing_cell_refinement 'Bruker SMART 1998' _computing_data_reduction 'Bruker SAINT 1998' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. No realistic model for the hydrogen atoms bound to the disordered C43 atom could be obtained. For this reason, although this atom is sp3 hybridised, it connectivity is only three. It should be noted that both the formula unit and the molecular weight are therefore inaccurate. ; _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^)+(0.0832P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef 'not refined' _refine_ls_number_reflns 8896 _refine_ls_number_parameters 642 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1709 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.1811 _refine_ls_wR_factor_gt 0.1472 _refine_ls_goodness_of_fit_ref 0.946 _refine_ls_restrained_S_all 0.946 _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 0.2348(6) 0.3562(5) 0.1927(4) 0.0996(18) Uani 1 1 d . . . H1A H 0.1605 0.4157 0.1973 0.120 Uiso 1 1 calc R . . H1B H 0.2615 0.3126 0.2403 0.120 Uiso 1 1 calc R . . C2 C 0.2988(5) 0.3346(4) 0.1228(3) 0.0718(14) Uani 1 1 d . . . H2 H 0.3726 0.2745 0.1207 0.086 Uiso 1 1 calc R . . C3 C 0.2663(4) 0.3971(3) 0.0440(3) 0.0541(11) Uani 1 1 d . . . H3A H 0.3279 0.4332 0.0137 0.065 Uiso 1 1 calc R . . H3B H 0.1844 0.4531 0.0557 0.065 Uiso 1 1 calc R . . C4 C 0.2616(3) 0.3303(3) -0.0112(2) 0.0394(9) Uani 1 1 d . . . C5 C 0.2325(4) 0.4037(3) -0.0924(2) 0.0475(10) Uani 1 1 d . . . H5A H 0.1525 0.4618 -0.0804 0.057 Uiso 1 1 calc R . . H5B H 0.2978 0.4367 -0.1198 0.057 Uiso 1 1 calc R . . C6 C 0.2257(4) 0.3449(3) -0.1482(2) 0.0525(11) Uani 1 1 d . . . H6 H 0.3010 0.2977 -0.1743 0.063 Uiso 1 1 calc R . . C7 C 0.1218(4) 0.3537(4) -0.1640(2) 0.0632(13) Uani 1 1 d . . . H7A H 0.0449 0.4002 -0.1390 0.076 Uiso 1 1 calc R . . H7B H 0.1240 0.3135 -0.2005 0.076 Uiso 1 1 calc R . . C8 C 0.3882(3) 0.2449(3) -0.0288(2) 0.0382(9) Uani 1 1 d . . . C9 C 0.1555(3) 0.2872(3) 0.0301(2) 0.0377(9) Uani 1 1 d . . . C10 C 0.3061(3) 0.1094(3) 0.03009(19) 0.0307(8) Uani 1 1 d . . . C11 C 0.2305(3) -0.0447(3) 0.0853(2) 0.0374(9) Uani 1 1 d . . . C12 C 0.1935(4) -0.2155(3) 0.1306(2) 0.0514(11) Uani 1 1 d . . . H12A H 0.1137 -0.1720 0.1613 0.062 Uiso 1 1 calc R . . H12B H 0.2331 -0.2757 0.1702 0.062 Uiso 1 1 calc R . . C13 C 0.1675(4) -0.2598(4) 0.0709(3) 0.0648(14) Uani 1 1 d . . . H13 H 0.118(4) -0.306(3) 0.103(2) 0.069(13) Uiso 1 1 d . . . C14 C 0.2854(5) -0.3249(4) 0.0188(4) 0.0945(18) Uani 1 1 d . . . H14A H 0.3336 -0.2787 -0.0149 0.142 Uiso 1 1 calc R . . H14B H 0.2639 -0.3552 -0.0162 0.142 Uiso 1 1 calc R . . H14C H 0.3348 -0.3826 0.0541 0.142 Uiso 1 1 calc R . . C15 C 0.0859(5) -0.1721(4) 0.0189(3) 0.0828(15) Uani 1 1 d . . . H15A H 0.0068 -0.1368 0.0538 0.124 Uiso 1 1 calc R . . H15B H 0.0707 -0.2028 -0.0190 0.124 Uiso 1 1 calc R . . H15C H 0.1274 -0.1199 -0.0119 0.124 Uiso 1 1 calc R . . C16 C 0.9010(4) 0.3598(4) 0.6183(3) 0.0693(13) Uani 1 1 d . . . H16A H 0.9172 0.2855 0.6380 0.083 Uiso 1 1 calc R . . H16B H 0.8671 0.4077 0.6556 0.083 Uiso 1 1 calc R . . C17 C 0.9255(4) 0.3960(4) 0.5400(3) 0.0586(12) Uani 1 1 d . . . H17 H 0.9079 0.4708 0.5230 0.070 Uiso 1 1 calc R . . C18 C 0.9790(3) 0.3293(3) 0.4749(2) 0.0510(11) Uani 1 1 d . . . H18A H 0.9940 0.2535 0.5011 0.061 Uiso 1 1 calc R . . H18B H 1.0601 0.3370 0.4437 0.061 Uiso 1 1 calc R . . C19 C 0.8957(3) 0.3587(3) 0.4152(2) 0.0404(9) Uani 1 1 d . . . C20 C 0.9529(4) 0.2787(3) 0.3558(3) 0.0588(12) Uani 1 1 d . . . H20A H 1.0335 0.2852 0.3221 0.071 Uiso 1 1 calc R . . H20B H 0.9687 0.2053 0.3875 0.071 Uiso 1 1 calc R . . C21 C 0.8702(5) 0.2972(4) 0.3009(3) 0.0737(15) Uani 1 1 d . . . H21 H 0.7958 0.2808 0.3251 0.088 Uiso 1 1 calc R . . C22 C 0.8920(6) 0.3332(4) 0.2246(3) 0.1018(19) Uani 1 1 d . . . H22A H 0.9654 0.3506 0.1981 0.122 Uiso 1 1 calc R . . H22B H 0.8349 0.3426 0.1942 0.122 Uiso 1 1 calc R . . C23 C 0.8910(4) 0.4674(3) 0.3657(2) 0.0398(9) Uani 1 1 d . . . C24 C 0.7701(3) 0.3505(3) 0.4633(2) 0.0414(9) Uani 1 1 d . . . C25 C 0.6701(3) 0.5284(3) 0.4198(2) 0.0334(9) Uani 1 1 d . . . C26 C 0.5523(4) 0.7195(3) 0.3820(2) 0.0367(9) Uani 1 1 d . . . C27 C 0.4078(4) 0.9025(3) 0.3695(3) 0.0570(12) Uani 1 1 d . . . H27A H 0.4787 0.9149 0.3258 0.068 Uiso 1 1 calc R . . H27B H 0.3913 0.9441 0.4116 0.068 Uiso 1 1 calc R . . C28 C 0.2953(4) 0.9411(4) 0.3349(3) 0.0653(13) Uani 1 1 d . . . H28 H 0.222(4) 0.932(3) 0.385(2) 0.062(12) Uiso 1 1 d . . . C29 C 0.3130(6) 0.8805(5) 0.2708(3) 0.114(2) Uani 1 1 d . . . H29A H 0.3834 0.8892 0.2261 0.171 Uiso 1 1 calc R . . H29B H 0.2378 0.9082 0.2500 0.171 Uiso 1 1 calc R . . H29C H 0.3292 0.8047 0.2946 0.171 Uiso 1 1 calc R . . C30 C 0.2633(5) 1.0609(4) 0.3020(4) 0.113(2) Uani 1 1 d . . . H30A H 0.3269 1.0735 0.2533 0.169 Uiso 1 1 calc R . . H30B H 0.2599 1.0970 0.3436 0.169 Uiso 1 1 calc R . . H30C H 0.1826 1.0890 0.2881 0.169 Uiso 1 1 calc R . . C31 C 0.8975(9) 1.0082(7) 0.4377(6) 0.159(4) Uani 1 1 d . . . H31A H 0.8309 1.0725 0.4467 0.191 Uiso 1 1 calc R . . H31B H 0.9368 0.9643 0.4804 0.191 Uiso 1 1 calc R . . C33 C 0.8989(5) 1.0241(4) 0.2968(3) 0.0748(15) Uani 1 1 d . . . H33A H 0.9759 0.9968 0.2559 0.090 Uiso 1 1 calc R . . H33B H 0.8728 1.1030 0.2845 0.090 Uiso 1 1 calc R . . C34 C 0.7964(4) 0.9899(3) 0.2870(2) 0.0502(11) Uani 1 1 d . B . C35 C 0.7902(4) 1.0214(3) 0.1961(2) 0.0629(13) Uani 1 1 d . . . H35A H 0.7649 1.1000 0.1802 0.076 Uiso 1 1 calc R . . H35B H 0.8741 0.9911 0.1623 0.076 Uiso 1 1 calc R . . C36 C 0.6998(5) 0.9830(5) 0.1775(3) 0.094(2) Uani 1 1 d . . . H36 H 0.7161 0.9082 0.1887 0.113 Uiso 1 1 calc R . . C37 C 0.6073(6) 1.0400(6) 0.1493(3) 0.130(3) Uani 1 1 d . . . H37A H 0.5869 1.1153 0.1371 0.156 Uiso 1 1 calc R . . H37B H 0.5571 1.0081 0.1401 0.156 Uiso 1 1 calc R . . C38 C 0.8344(3) 0.8708(3) 0.3119(2) 0.0394(9) Uani 1 1 d . . . C39 C 0.6760(4) 1.0464(3) 0.3409(3) 0.0686(14) Uani 1 1 d . . . C40 C 0.6730(3) 0.8946(3) 0.4339(2) 0.0341(9) Uani 1 1 d . . . C41 C 0.6525(4) 0.7345(3) 0.5363(2) 0.0423(10) Uani 1 1 d . . . C42A C 0.6255(8) 0.5954(6) 0.6492(5) 0.049(3) Uiso 0.520(10) 1 d P A 1 H42A H 0.6470 0.5481 0.6101 0.059 Uiso 0.520(10) 1 calc PR A 1 H42B H 0.7044 0.5875 0.6602 0.059 Uiso 0.520(10) 1 calc PR A 1 C42B C 0.5576(10) 0.5970(7) 0.6312(5) 0.050(3) Uiso 0.480(10) 1 d P A 2 H42C H 0.5181 0.5944 0.5908 0.060 Uiso 0.480(10) 1 calc PR A 2 H42D H 0.6414 0.5427 0.6227 0.060 Uiso 0.480(10) 1 calc PR A 2 C43A C 0.5622(10) 0.5562(7) 0.7163(5) 0.056(3) Uiso 0.520(10) 1 d P A 1 C43B C 0.5015(9) 0.5651(7) 0.6960(6) 0.052(3) Uiso 0.480(10) 1 d P A 2 C44 C 0.4744(6) 0.6131(4) 0.7785(3) 0.114(2) Uani 1 1 d . . . H44A H 0.4634 0.6866 0.7775 0.170 Uiso 1 1 d R A . H44B H 0.4701 0.5757 0.8343 0.170 Uiso 1 1 d R . . H44C H 0.4053 0.6129 0.7617 0.170 Uiso 1 1 d R A . C45 C 0.5547(5) 0.4404(4) 0.7289(3) 0.0973(19) Uani 1 1 d . . . H45A H 0.6047 0.3939 0.6897 0.146 Uiso 1 1 d R A . H45B H 0.4758 0.4293 0.7556 0.146 Uiso 1 1 d R . . H45C H 0.5956 0.4298 0.7714 0.146 Uiso 1 1 d R . . N1 N 0.4052(2) 0.1376(2) -0.00656(17) 0.0341(7) Uani 1 1 d . . . N2 N 0.1889(3) 0.1768(3) 0.04822(18) 0.0374(8) Uani 1 1 d . . . H2N H 0.139(3) 0.147(3) 0.070(2) 0.030(11) Uiso 1 1 d . . . N3 N 0.3226(3) 0.0038(3) 0.05047(18) 0.0345(8) Uani 1 1 d . . . H3N H 0.393(3) -0.034(2) 0.0372(17) 0.015(9) Uiso 1 1 d . . . N4 N 0.2735(3) -0.1497(3) 0.09217(18) 0.0408(8) Uani 1 1 d . . . H4N H 0.358(4) -0.187(3) 0.077(2) 0.046(11) Uiso 1 1 d . . . N5 N 0.7753(3) 0.5444(3) 0.36911(19) 0.0392(8) Uani 1 1 d . . . N6 N 0.6629(3) 0.4365(2) 0.46571(17) 0.0370(7) Uani 1 1 d . . . N7 N 0.5635(3) 0.6136(2) 0.42294(18) 0.0362(8) Uani 1 1 d . . . H7N H 0.493(3) 0.608(2) 0.459(2) 0.033(10) Uiso 1 1 d . . . N8 N 0.4406(3) 0.7887(2) 0.4056(2) 0.0469(9) Uani 1 1 d . . . H8N H 0.371(4) 0.768(3) 0.441(2) 0.065(13) Uiso 1 1 d . . . N9 N 0.7772(3) 0.8336(3) 0.38939(19) 0.0371(8) Uani 1 1 d . B . H9N H 0.797(3) 0.767(3) 0.408(2) 0.050(13) Uiso 1 1 d . . . N10 N 0.6199(3) 0.9975(2) 0.41285(18) 0.0475(9) Uani 1 1 d . B . N11 N 0.6180(3) 0.8458(2) 0.50625(18) 0.0369(8) Uani 1 1 d . B . H11N H 0.548(4) 0.888(3) 0.531(2) 0.060(14) Uiso 1 1 d . . . N12 N 0.5779(4) 0.7072(3) 0.6053(2) 0.0694(13) Uani 1 1 d . A . H12N H 0.513(4) 0.751(3) 0.626(2) 0.058(14) Uiso 1 1 d . . . O1 O 0.4782(2) 0.2749(2) -0.06404(17) 0.0569(8) Uani 1 1 d . . . O2 O 0.0482(2) 0.3423(2) 0.04659(16) 0.0528(7) Uani 1 1 d . . . O3 O 0.1206(2) 0.0097(2) 0.10764(15) 0.0488(7) Uani 1 1 d . . . O4 O 0.9822(2) 0.4889(2) 0.32337(16) 0.0547(8) Uani 1 1 d . . . O5 O 0.7657(2) 0.2621(2) 0.50270(17) 0.0586(8) Uani 1 1 d . . . O6 O 0.6403(2) 0.74186(19) 0.33104(15) 0.0470(7) Uani 1 1 d . . . O7 O 0.9147(2) 0.8098(2) 0.26944(15) 0.0491(7) Uani 1 1 d . . . O8A O 0.5990(7) 1.1382(5) 0.3049(4) 0.050(3) Uiso 0.431(12) 1 d P B 1 O8B O 0.6478(5) 1.1459(4) 0.3282(3) 0.045(2) Uiso 0.569(12) 1 d P B 2 O9 O 0.7441(3) 0.6718(2) 0.50016(15) 0.0524(7) Uani 1 1 d . B . H5N H 0.766(3) 0.610(3) 0.344(2) 0.047(12) Uiso 1 1 d . . . C32 C 0.9277(9) 0.9855(8) 0.3806(4) 0.159(5) Uani 1 1 d . . . H32 H 0.9945 0.9198 0.3814 0.191 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 0.101(5) 0.111(5) 0.101(5) -0.018(4) -0.024(4) -0.050(4) C2 0.068(3) 0.080(4) 0.071(4) -0.039(3) -0.008(3) -0.017(3) C3 0.049(3) 0.049(3) 0.065(3) -0.022(2) -0.008(2) -0.013(2) C4 0.037(2) 0.033(2) 0.043(2) -0.0091(18) -0.0061(17) -0.0081(18) C5 0.043(2) 0.037(2) 0.052(3) 0.000(2) -0.0047(19) -0.0125(19) C6 0.053(3) 0.047(3) 0.045(3) 0.000(2) -0.008(2) -0.011(2) C7 0.067(3) 0.073(3) 0.044(3) -0.005(2) -0.006(2) -0.028(3) C8 0.034(2) 0.036(2) 0.043(2) -0.0075(18) -0.0076(17) -0.0104(19) C9 0.034(2) 0.039(2) 0.033(2) -0.0060(18) -0.0046(17) -0.0079(19) C10 0.027(2) 0.033(2) 0.030(2) -0.0075(16) -0.0062(15) -0.0062(18) C11 0.033(2) 0.042(3) 0.037(2) 0.0001(18) -0.0051(17) -0.020(2) C12 0.042(2) 0.046(3) 0.061(3) 0.006(2) -0.006(2) -0.024(2) C13 0.061(3) 0.050(3) 0.091(4) 0.000(3) -0.017(3) -0.035(3) C14 0.086(4) 0.074(4) 0.135(5) -0.053(4) -0.014(4) -0.024(3) C15 0.080(4) 0.086(4) 0.095(4) -0.006(3) -0.039(3) -0.033(3) C16 0.060(3) 0.074(3) 0.065(3) -0.011(3) -0.018(2) -0.010(3) C17 0.055(3) 0.059(3) 0.063(3) -0.008(3) -0.014(2) -0.022(2) C18 0.034(2) 0.047(3) 0.056(3) -0.001(2) -0.0066(19) -0.006(2) C19 0.034(2) 0.032(2) 0.046(2) -0.0040(18) -0.0054(18) -0.0072(18) C20 0.061(3) 0.043(3) 0.059(3) -0.014(2) 0.003(2) -0.015(2) C21 0.105(4) 0.052(3) 0.063(3) -0.022(3) 0.001(3) -0.033(3) C22 0.144(6) 0.104(5) 0.067(4) -0.013(3) -0.007(4) -0.067(4) C23 0.036(2) 0.039(2) 0.042(2) -0.0109(18) -0.0024(18) -0.012(2) C24 0.036(2) 0.035(2) 0.047(2) -0.0032(19) -0.0076(18) -0.011(2) C25 0.033(2) 0.035(2) 0.031(2) -0.0076(17) -0.0075(16) -0.0097(19) C26 0.041(2) 0.029(2) 0.039(2) 0.0008(18) -0.0121(19) -0.013(2) C27 0.051(3) 0.034(2) 0.075(3) 0.001(2) -0.012(2) -0.012(2) C28 0.057(3) 0.054(3) 0.060(3) 0.011(3) -0.015(3) -0.006(2) C29 0.139(6) 0.110(5) 0.075(4) -0.011(4) -0.052(4) -0.006(4) C30 0.083(4) 0.052(3) 0.140(5) 0.027(3) -0.019(4) 0.007(3) C31 0.236(10) 0.184(9) 0.145(8) 0.020(7) -0.070(7) -0.174(8) C33 0.104(4) 0.069(3) 0.059(3) -0.022(3) 0.025(3) -0.062(3) C34 0.062(3) 0.040(2) 0.038(2) -0.0054(19) 0.0084(19) -0.022(2) C35 0.055(3) 0.056(3) 0.044(3) 0.005(2) 0.007(2) -0.009(2) C36 0.058(3) 0.120(5) 0.059(3) 0.038(3) -0.018(3) -0.019(3) C37 0.099(5) 0.176(7) 0.074(4) 0.020(4) -0.014(4) -0.039(5) C38 0.036(2) 0.047(3) 0.035(2) -0.009(2) -0.0014(18) -0.018(2) C39 0.076(3) 0.032(3) 0.056(3) -0.002(2) 0.016(2) -0.005(2) C40 0.036(2) 0.036(2) 0.032(2) -0.0090(18) -0.0041(17) -0.0146(19) C41 0.056(3) 0.032(2) 0.031(2) 0.0002(18) -0.007(2) -0.013(2) C44 0.143(6) 0.083(4) 0.078(4) -0.008(3) 0.005(4) -0.029(4) C45 0.116(5) 0.053(3) 0.102(4) 0.005(3) -0.003(3) -0.036(3) N1 0.0300(17) 0.0307(18) 0.0397(18) -0.0049(14) -0.0065(14) -0.0103(14) N2 0.0295(19) 0.036(2) 0.0390(19) -0.0040(15) 0.0004(15) -0.0119(17) N3 0.0230(18) 0.032(2) 0.0418(19) -0.0058(15) -0.0028(14) -0.0061(16) N4 0.0306(19) 0.034(2) 0.052(2) -0.0001(16) -0.0044(15) -0.0150(17) N5 0.0341(19) 0.030(2) 0.0423(19) -0.0035(16) -0.0006(15) -0.0078(16) N6 0.0358(18) 0.0274(18) 0.0426(18) -0.0012(15) -0.0084(14) -0.0093(15) N7 0.0312(18) 0.0291(19) 0.0405(19) -0.0023(15) -0.0039(15) -0.0084(16) N8 0.034(2) 0.0322(19) 0.063(2) -0.0041(17) -0.0039(17) -0.0087(17) N9 0.0353(19) 0.033(2) 0.039(2) -0.0064(16) 0.0002(15) -0.0140(16) N10 0.053(2) 0.030(2) 0.0395(19) 0.0012(15) 0.0073(15) -0.0128(17) N11 0.0365(19) 0.0319(19) 0.0318(18) -0.0007(15) -0.0015(15) -0.0092(16) N12 0.087(3) 0.035(2) 0.041(2) 0.0039(18) 0.019(2) -0.007(2) O1 0.0354(16) 0.0380(16) 0.088(2) -0.0051(15) -0.0030(15) -0.0156(13) O2 0.0341(16) 0.0432(17) 0.0626(18) -0.0093(14) -0.0004(13) -0.0026(14) O3 0.0276(15) 0.0450(17) 0.0607(18) -0.0026(13) 0.0001(13) -0.0116(13) O4 0.0382(16) 0.0491(17) 0.0664(19) -0.0073(14) 0.0029(14) -0.0177(14) O5 0.0436(17) 0.0302(16) 0.080(2) 0.0067(15) -0.0035(14) -0.0101(13) O6 0.0426(16) 0.0369(16) 0.0494(16) 0.0018(12) -0.0028(13) -0.0136(13) O7 0.0439(16) 0.0495(17) 0.0434(16) -0.0123(14) 0.0030(13) -0.0125(14) O9 0.0591(19) 0.0337(16) 0.0425(16) -0.0033(13) 0.0000(14) -0.0046(14) C32 0.265(10) 0.264(10) 0.054(4) -0.063(5) 0.052(5) -0.243(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 C2 1.276(7) . ? C1 H1A 0.9500 . ? C1 H1B 0.9500 . ? C2 C3 1.494(6) . ? C2 H2 0.9500 . ? C3 C4 1.545(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C9 1.514(5) . ? C4 C8 1.523(5) . ? C4 C5 1.557(5) . ? C5 C6 1.481(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.322(6) . ? C6 H6 0.9500 . ? C7 H7A 0.9500 . ? C7 H7B 0.9500 . ? C8 O1 1.234(4) . ? C8 N1 1.375(4) . ? C9 O2 1.205(4) . ? C9 N2 1.388(5) . ? C10 N1 1.319(4) . ? C10 N2 1.348(4) . ? C10 N3 1.354(4) . ? C11 O3 1.238(4) . ? C11 N4 1.323(4) . ? C11 N3 1.409(4) . ? C12 N4 1.468(4) . ? C12 C13 1.520(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C15 1.513(6) . ? C13 C14 1.520(6) . ? C13 H13 0.99(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.309(6) . ? C16 H16A 0.9500 . ? C16 H16B 0.9500 . ? C17 C18 1.499(6) . ? C17 H17 0.9500 . ? C18 C19 1.547(5) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C23 1.502(5) . ? C19 C24 1.515(5) . ? C19 C20 1.547(5) . ? C20 C21 1.506(7) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.276(6) . ? C21 H21 0.9500 . ? C22 H22A 0.9500 . ? C22 H22B 0.9500 . ? C23 O4 1.212(4) . ? C23 N5 1.380(5) . ? C24 O5 1.239(4) . ? C24 N6 1.370(4) . ? C25 N6 1.322(4) . ? C25 N7 1.360(4) . ? C25 N5 1.360(4) . ? C26 O6 1.237(4) . ? C26 N8 1.328(5) . ? C26 N7 1.416(4) . ? C27 N8 1.467(5) . ? C27 C28 1.507(6) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.506(7) . ? C28 C30 1.529(6) . ? C28 H28 1.05(4) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C32 1.049(9) . ? C31 H31A 0.9500 . ? C31 H31B 0.9500 . ? C33 C32 1.524(10) . ? C33 C34 1.557(6) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C38 1.502(5) . ? C34 C39 1.510(5) . ? C34 C35 1.555(5) . ? C35 C36 1.537(7) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.246(7) . ? C36 H36 0.9500 . ? C37 H37A 0.9500 . ? C37 H37B 0.9500 . ? C38 O7 1.212(4) . ? C38 N9 1.375(4) . ? C39 O8B 1.255(6) . ? C39 N10 1.363(5) . ? C39 O8A 1.368(8) . ? C40 N10 1.310(4) . ? C40 N9 1.352(4) . ? C40 N11 1.361(4) . ? C41 O9 1.222(4) . ? C41 N12 1.321(5) . ? C41 N11 1.417(5) . ? C42A C43A 1.293(10) . ? C42A N12 1.495(8) . ? C42A H42A 0.9900 . ? C42A H42B 0.9900 . ? C42B C43B 1.191(11) . ? C42B N12 1.560(9) . ? C42B H42C 0.9900 . ? C42B H42D 0.9900 . ? C43A C44 1.429(9) . ? C43A C45 1.592(10) . ? C43B C45 1.592(10) . ? C43B C44 1.655(11) . ? C43B H44C 1.4511 . ? C44 H44C 0.9700 . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C44 H44C 0.9700 . ? C45 H45A 0.9696 . ? C45 H45B 0.9700 . ? C45 H45C 0.9701 . ? N2 H2N 0.80(3) . ? N3 H3N 0.80(3) . ? N4 H4N 0.93(4) . ? N5 H5N 0.87(4) . ? N7 H7N 0.90(3) . ? N8 H8N 0.96(4) . ? N9 H9N 0.85(4) . ? N11 H11N 0.88(4) . ? N12 H12N 0.83(4) . ? C32 H32 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 120.0 . . ? C2 C1 H1B 120.0 . . ? H1A C1 H1B 120.0 . . ? C1 C2 C3 124.8(5) . . ? C1 C2 H2 117.6 . . ? C3 C2 H2 117.6 . . ? C2 C3 C4 114.7(3) . . ? C2 C3 H3A 108.6 . . ? C4 C3 H3A 108.6 . . ? C2 C3 H3B 108.6 . . ? C4 C3 H3B 108.6 . . ? H3A C3 H3B 107.6 . . ? C9 C4 C8 114.4(3) . . ? C9 C4 C3 108.8(3) . . ? C8 C4 C3 107.9(3) . . ? C9 C4 C5 106.8(3) . . ? C8 C4 C5 109.5(3) . . ? C3 C4 C5 109.5(3) . . ? C6 C5 C4 112.4(3) . . ? C6 C5 H5A 109.1 . . ? C4 C5 H5A 109.1 . . ? C6 C5 H5B 109.1 . . ? C4 C5 H5B 109.1 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 124.3(4) . . ? C7 C6 H6 117.8 . . ? C5 C6 H6 117.8 . . ? C6 C7 H7A 120.0 . . ? C6 C7 H7B 120.0 . . ? H7A C7 H7B 120.0 . . ? O1 C8 N1 119.7(3) . . ? O1 C8 C4 117.5(3) . . ? N1 C8 C4 122.8(3) . . ? O2 C9 N2 120.5(3) . . ? O2 C9 C4 124.1(3) . . ? N2 C9 C4 115.4(3) . . ? N1 C10 N2 125.6(3) . . ? N1 C10 N3 117.4(3) . . ? N2 C10 N3 117.0(3) . . ? O3 C11 N4 125.4(3) . . ? O3 C11 N3 120.7(3) . . ? N4 C11 N3 113.9(3) . . ? N4 C12 C13 113.9(3) . . ? N4 C12 H12A 108.8 . . ? C13 C12 H12A 108.8 . . ? N4 C12 H12B 108.8 . . ? C13 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C15 C13 C12 111.2(4) . . ? C15 C13 C14 111.3(5) . . ? C12 C13 C14 112.5(4) . . ? C15 C13 H13 105(2) . . ? C12 C13 H13 107(2) . . ? C14 C13 H13 109(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 H16A 120.0 . . ? C17 C16 H16B 120.0 . . ? H16A C16 H16B 120.0 . . ? C16 C17 C18 125.4(4) . . ? C16 C17 H17 117.3 . . ? C18 C17 H17 117.3 . . ? C17 C18 C19 114.0(3) . . ? C17 C18 H18A 108.7 . . ? C19 C18 H18A 108.7 . . ? C17 C18 H18B 108.7 . . ? C19 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C23 C19 C24 114.1(3) . . ? C23 C19 C18 108.3(3) . . ? C24 C19 C18 108.7(3) . . ? C23 C19 C20 107.8(3) . . ? C24 C19 C20 108.0(3) . . ? C18 C19 C20 109.9(3) . . ? C21 C20 C19 112.4(3) . . ? C21 C20 H20A 109.1 . . ? C19 C20 H20A 109.1 . . ? C21 C20 H20B 109.1 . . ? C19 C20 H20B 109.1 . . ? H20A C20 H20B 107.9 . . ? C22 C21 C20 125.2(5) . . ? C22 C21 H21 117.4 . . ? C20 C21 H21 117.4 . . ? C21 C22 H22A 120.0 . . ? C21 C22 H22B 120.0 . . ? H22A C22 H22B 120.0 . . ? O4 C23 N5 119.9(3) . . ? O4 C23 C19 123.4(3) . . ? N5 C23 C19 116.7(3) . . ? O5 C24 N6 119.3(3) . . ? O5 C24 C19 117.9(3) . . ? N6 C24 C19 122.8(3) . . ? N6 C25 N7 117.3(3) . . ? N6 C25 N5 125.3(3) . . ? N7 C25 N5 117.4(3) . . ? O6 C26 N8 125.6(3) . . ? O6 C26 N7 121.6(3) . . ? N8 C26 N7 112.8(3) . . ? N8 C27 C28 111.9(3) . . ? N8 C27 H27A 109.2 . . ? C28 C27 H27A 109.2 . . ? N8 C27 H27B 109.2 . . ? C28 C27 H27B 109.2 . . ? H27A C27 H27B 107.9 . . ? C29 C28 C27 112.3(4) . . ? C29 C28 C30 111.7(4) . . ? C27 C28 C30 108.9(4) . . ? C29 C28 H28 112(2) . . ? C27 C28 H28 105(2) . . ? C30 C28 H28 106(2) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C32 C31 H31A 120.0 . . ? C32 C31 H31B 120.0 . . ? H31A C31 H31B 120.0 . . ? C32 C33 C34 115.0(4) . . ? C32 C33 H33A 108.5 . . ? C34 C33 H33A 108.5 . . ? C32 C33 H33B 108.5 . . ? C34 C33 H33B 108.5 . . ? H33A C33 H33B 107.5 . . ? C38 C34 C39 112.5(3) . . ? C38 C34 C35 109.4(3) . . ? C39 C34 C35 111.7(4) . . ? C38 C34 C33 107.0(3) . . ? C39 C34 C33 107.2(4) . . ? C35 C34 C33 109.0(3) . . ? C36 C35 C34 113.8(3) . . ? C36 C35 H35A 108.8 . . ? C34 C35 H35A 108.8 . . ? C36 C35 H35B 108.8 . . ? C34 C35 H35B 108.8 . . ? H35A C35 H35B 107.7 . . ? C37 C36 C35 126.6(7) . . ? C37 C36 H36 116.7 . . ? C35 C36 H36 116.7 . . ? C36 C37 H37A 120.0 . . ? C36 C37 H37B 120.0 . . ? H37A C37 H37B 120.0 . . ? O7 C38 N9 121.0(4) . . ? O7 C38 C34 123.3(3) . . ? N9 C38 C34 115.6(3) . . ? O8B C39 N10 118.5(4) . . ? O8B C39 O8A 38.4(3) . . ? N10 C39 O8A 115.1(4) . . ? O8B C39 C34 114.6(4) . . ? N10 C39 C34 123.9(4) . . ? O8A C39 C34 117.2(4) . . ? N10 C40 N9 125.1(3) . . ? N10 C40 N11 117.1(3) . . ? N9 C40 N11 117.8(3) . . ? O9 C41 N12 124.8(4) . . ? O9 C41 N11 121.3(3) . . ? N12 C41 N11 114.0(4) . . ? C43A C42A N12 123.1(7) . . ? C43A C42A H42A 106.6 . . ? N12 C42A H42A 106.6 . . ? C43A C42A H42B 106.6 . . ? N12 C42A H42B 106.6 . . ? H42A C42A H42B 106.5 . . ? C43B C42B N12 125.4(8) . . ? C43B C42B H42C 106.0 . . ? N12 C42B H42C 106.0 . . ? C43B C42B H42D 106.0 . . ? N12 C42B H42D 106.0 . . ? H42C C42B H42D 106.3 . . ? C42A C43A C44 126.5(8) . . ? C42A C43A C45 120.7(7) . . ? C44 C43A C45 111.6(6) . . ? C42B C43B C45 115.6(8) . . ? C42B C43B C44 122.9(8) . . ? C45 C43B C44 100.7(6) . . ? C42B C43B H44C 135.9 . . ? C45 C43B H44C 107.5 . . ? C44 C43B H44C 35.6 . . ? H44C C44 C43A 91.8 . . ? H44C C44 C43B 60.6 . . ? C43A C44 C43B 31.5(4) . . ? H44C C44 H44A 107.8 . . ? C43A C44 H44A 121.9 . . ? C43B C44 H44A 123.5 . . ? H44C C44 H44B 107.9 . . ? C43A C44 H44B 117.2 . . ? C43B C44 H44B 128.6 . . ? H44A C44 H44B 107.9 . . ? H44C C44 H44C 0.0 . . ? C43A C44 H44C 91.8 . . ? C43B C44 H44C 60.6 . . ? H44A C44 H44C 107.8 . . ? H44B C44 H44C 107.9 . . ? C43A C45 C43B 31.6(4) . . ? C43A C45 H45A 121.4 . . ? C43B C45 H45A 118.2 . . ? C43A C45 H45B 118.6 . . ? C43B C45 H45B 97.5 . . ? H45A C45 H45B 112.1 . . ? C43A C45 H45C 79.4 . . ? C43B C45 H45C 108.4 . . ? H45A C45 H45C 112.3 . . ? H45B C45 H45C 106.9 . . ? C10 N1 C8 117.5(3) . . ? C10 N2 C9 124.4(3) . . ? C10 N2 H2N 113(2) . . ? C9 N2 H2N 122(2) . . ? C10 N3 C11 127.4(3) . . ? C10 N3 H3N 114(2) . . ? C11 N3 H3N 118(2) . . ? C11 N4 C12 122.4(3) . . ? C11 N4 H4N 121(2) . . ? C12 N4 H4N 116(2) . . ? C25 N5 C23 123.1(3) . . ? C25 N5 H5N 114(2) . . ? C23 N5 H5N 122(2) . . ? C25 N6 C24 117.6(3) . . ? C25 N7 C26 126.2(3) . . ? C25 N7 H7N 120(2) . . ? C26 N7 H7N 113(2) . . ? C26 N8 C27 121.9(3) . . ? C26 N8 H8N 123(2) . . ? C27 N8 H8N 114(2) . . ? C40 N9 C38 123.5(3) . . ? C40 N9 H9N 115(3) . . ? C38 N9 H9N 120(3) . . ? C40 N10 C39 117.0(3) . . ? C40 N11 C41 126.0(3) . . ? C40 N11 H11N 114(3) . . ? C41 N11 H11N 119(3) . . ? C41 N12 C42A 115.8(5) . . ? C41 N12 C42B 123.4(5) . . ? C42A N12 C42B 36.5(4) . . ? C41 N12 H12N 122(3) . . ? C42A N12 H12N 122(3) . . ? C42B N12 H12N 107(3) . . ? C31 C32 C33 140.3(13) . . ? C31 C32 H32 109.8 . . ? C33 C32 H32 109.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 C4 -126.4(5) . . . . ? C2 C3 C4 C9 66.1(4) . . . . ? C2 C3 C4 C8 -58.5(4) . . . . ? C2 C3 C4 C5 -177.6(4) . . . . ? C9 C4 C5 C6 -62.0(4) . . . . ? C8 C4 C5 C6 62.3(4) . . . . ? C3 C4 C5 C6 -179.6(3) . . . . ? C4 C5 C6 C7 107.5(4) . . . . ? C9 C4 C8 O1 178.4(3) . . . . ? C3 C4 C8 O1 -60.4(4) . . . . ? C5 C4 C8 O1 58.7(4) . . . . ? C9 C4 C8 N1 -2.1(5) . . . . ? C3 C4 C8 N1 119.1(4) . . . . ? C5 C4 C8 N1 -121.9(4) . . . . ? C8 C4 C9 O2 -177.5(3) . . . . ? C3 C4 C9 O2 61.8(5) . . . . ? C5 C4 C9 O2 -56.3(5) . . . . ? C8 C4 C9 N2 1.9(4) . . . . ? C3 C4 C9 N2 -118.8(3) . . . . ? C5 C4 C9 N2 123.2(3) . . . . ? N4 C12 C13 C15 -69.1(5) . . . . ? N4 C12 C13 C14 56.5(5) . . . . ? C16 C17 C18 C19 120.5(4) . . . . ? C17 C18 C19 C23 67.9(4) . . . . ? C17 C18 C19 C24 -56.6(4) . . . . ? C17 C18 C19 C20 -174.6(3) . . . . ? C23 C19 C20 C21 -67.3(4) . . . . ? C24 C19 C20 C21 56.4(4) . . . . ? C18 C19 C20 C21 174.8(3) . . . . ? C19 C20 C21 C22 110.2(5) . . . . ? C24 C19 C23 O4 -179.9(3) . . . . ? C18 C19 C23 O4 58.9(5) . . . . ? C20 C19 C23 O4 -60.0(5) . . . . ? C24 C19 C23 N5 -1.0(5) . . . . ? C18 C19 C23 N5 -122.2(3) . . . . ? C20 C19 C23 N5 118.9(4) . . . . ? C23 C19 C24 O5 176.8(3) . . . . ? C18 C19 C24 O5 -62.3(4) . . . . ? C20 C19 C24 O5 57.0(4) . . . . ? C23 C19 C24 N6 -4.1(5) . . . . ? C18 C19 C24 N6 116.9(4) . . . . ? C20 C19 C24 N6 -123.8(4) . . . . ? N8 C27 C28 C29 -58.3(5) . . . . ? N8 C27 C28 C30 177.4(4) . . . . ? C32 C33 C34 C38 -54.1(6) . . . . ? C32 C33 C34 C39 66.7(6) . . . . ? C32 C33 C34 C35 -172.3(5) . . . . ? C38 C34 C35 C36 58.4(5) . . . . ? C39 C34 C35 C36 -66.8(5) . . . . ? C33 C34 C35 C36 175.0(4) . . . . ? C34 C35 C36 C37 119.6(6) . . . . ? C39 C34 C38 O7 166.4(4) . . . . ? C35 C34 C38 O7 41.7(5) . . . . ? C33 C34 C38 O7 -76.2(5) . . . . ? C39 C34 C38 N9 -17.6(5) . . . . ? C35 C34 C38 N9 -142.2(3) . . . . ? C33 C34 C38 N9 99.9(4) . . . . ? C38 C34 C39 O8B 172.2(5) . . . . ? C35 C34 C39 O8B -64.4(6) . . . . ? C33 C34 C39 O8B 54.9(6) . . . . ? C38 C34 C39 N10 11.9(7) . . . . ? C35 C34 C39 N10 135.3(5) . . . . ? C33 C34 C39 N10 -105.4(5) . . . . ? C38 C34 C39 O8A -145.0(5) . . . . ? C35 C34 C39 O8A -21.6(7) . . . . ? C33 C34 C39 O8A 97.7(6) . . . . ? N12 C42A C43A C44 -31.9(15) . . . . ? N12 C42A C43A C45 134.8(9) . . . . ? N12 C42B C43B C45 -144.4(9) . . . . ? N12 C42B C43B C44 -20.6(15) . . . . ? C42A C43A C44 H44C 104.3 . . . . ? C45 C43A C44 H44C -63.4 . . . . ? C42A C43A C44 C43B 95.2(13) . . . . ? C45 C43A C44 C43B -72.5(10) . . . . ? C42B C43B C44 H44C 124.6 . . . . ? C45 C43B C44 H44C -105.2 . . . . ? C42B C43B C44 C43A -65.8(12) . . . . ? C45 C43B C44 C43A 64.4(9) . . . . ? C42A C43A C45 C43B -86.4(12) . . . . ? C44 C43A C45 C43B 82.2(11) . . . . ? C42B C43B C45 C43A 80.7(12) . . . . ? C44 C43B C45 C43A -54.0(9) . . . . ? N2 C10 N1 C8 -0.4(5) . . . . ? N3 C10 N1 C8 178.7(3) . . . . ? O1 C8 N1 C10 -179.2(3) . . . . ? C4 C8 N1 C10 1.4(5) . . . . ? N1 C10 N2 C9 0.4(5) . . . . ? N3 C10 N2 C9 -178.7(3) . . . . ? O2 C9 N2 C10 178.2(3) . . . . ? C4 C9 N2 C10 -1.3(5) . . . . ? N1 C10 N3 C11 -175.9(3) . . . . ? N2 C10 N3 C11 3.3(5) . . . . ? O3 C11 N3 C10 -6.7(6) . . . . ? N4 C11 N3 C10 174.5(3) . . . . ? O3 C11 N4 C12 -1.9(6) . . . . ? N3 C11 N4 C12 176.8(3) . . . . ? C13 C12 N4 C11 106.8(4) . . . . ? N6 C25 N5 C23 -6.6(6) . . . . ? N7 C25 N5 C23 174.0(3) . . . . ? O4 C23 N5 C25 -175.0(3) . . . . ? C19 C23 N5 C25 6.0(5) . . . . ? N7 C25 N6 C24 -179.5(3) . . . . ? N5 C25 N6 C24 1.1(5) . . . . ? O5 C24 N6 C25 -176.7(3) . . . . ? C19 C24 N6 C25 4.2(5) . . . . ? N6 C25 N7 C26 176.6(3) . . . . ? N5 C25 N7 C26 -3.9(5) . . . . ? O6 C26 N7 C25 8.1(5) . . . . ? N8 C26 N7 C25 -170.7(3) . . . . ? O6 C26 N8 C27 2.8(6) . . . . ? N7 C26 N8 C27 -178.5(3) . . . . ? C28 C27 N8 C26 123.8(4) . . . . ? N10 C40 N9 C38 -6.6(6) . . . . ? N11 C40 N9 C38 173.1(3) . . . . ? O7 C38 N9 C40 -167.6(4) . . . . ? C34 C38 N9 C40 16.3(5) . . . . ? N9 C40 N10 C39 -1.0(6) . . . . ? N11 C40 N10 C39 179.3(4) . . . . ? O8B C39 N10 C40 -162.2(5) . . . . ? O8A C39 N10 C40 154.8(5) . . . . ? C34 C39 N10 C40 -2.6(7) . . . . ? N10 C40 N11 C41 173.1(3) . . . . ? N9 C40 N11 C41 -6.6(5) . . . . ? O9 C41 N11 C40 5.3(6) . . . . ? N12 C41 N11 C40 -174.9(4) . . . . ? O9 C41 N12 C42A 13.4(7) . . . . ? N11 C41 N12 C42A -166.3(5) . . . . ? O9 C41 N12 C42B -27.9(8) . . . . ? N11 C41 N12 C42B 152.4(6) . . . . ? C43A C42A N12 C41 -178.3(8) . . . . ? C43A C42A N12 C42B -66.3(10) . . . . ? C43B C42B N12 C41 171.9(9) . . . . ? C43B C42B N12 C42A 82.8(12) . . . . ? C34 C33 C32 C31 -86.9(11) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.453 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.048