# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_section_title ;Dimerization of aromatic ureido pyrimidinedione derivatives: Observation of an unexpected tautomer in the solid state ; loop_ _publ_author_name A.Kaifer 'Lu Cui.' 'Suresh Gadde' 'Joel Mague' 'Atindra D. Shukla' 'Hao Sun.' _publ_contact_author_name 'Angel Kaifer' _publ_contact_author_email AKAIFER@MIAMI.EDU # Attachment 'Compound_2.cif' data_aek004_0m _database_code_depnum_ccdc_archive 'CCDC 670607' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(5,5-Diaalyl-4,6-dioxo-1,4,5,6-tetrahydropyrimidin- 2-yl)-3-phenylurea ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H18 N4 O3' _chemical_formula_sum 'C17 H18 N4 O3' _chemical_formula_weight 326.35 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.8599(5) _cell_length_b 16.4465(8) _cell_length_c 10.6945(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.003(1) _cell_angle_gamma 90.00 _cell_volume 1649.32(14) _cell_formula_units_Z 4 _cell_measurement_temperature 102(2) _cell_measurement_reflns_used 9940 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 28.32 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9399 _exptl_absorpt_correction_T_max 0.9882 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5 deg. in omega, colllected at phi = 0.00, 90.00 and 180.00 deg. and 2 sets of 800 frames, each of width 0.45 deg in phi, collected at omega = -30.00 and 210.00 deg. ; _diffrn_ambient_temperature 102(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-AXS Smart APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28739 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 28.35 _reflns_number_total 4112 _reflns_number_gt 3275 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2 (Bruker-AXS, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker-AXS, 2006)' _computing_data_reduction 'Bruker SAINT+ (Bruker-AXS, 2006a)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker APEX2 (Bruker-AXS, 2006)' _computing_publication_material 'Bruker APEX2 (Bruker-AXS, 2006)' _publ_section_references ; Bruker-AXS (2006). APEX2, Version 2.1-0, Madison, WI. Bruker-AXS (2006a). SAINT+, Version 7.34A, Madison, WI Sheldrick, G. M. (1997). SHELXS-97 and SHELXL-97. University of G\"ottingen, Germany. Sheldrick, G, M. (2007). SADABS, Version 2007/2. University of G\"ottingen, Germany. ; _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. H-atoms attached to carbon were placed in calculated positions (C---H = 0.95 - 0.98 \%A) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms. H-atoms attached to nitrogen were refined with isotropic displacement parameters ; _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^)+(0.0448P)^2^+0.5796P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4112 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1057 _refine_ls_wR_factor_gt 0.0968 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.80221(10) 1.01593(6) 0.27948(9) 0.0260(2) Uani 1 1 d . . . O2 O 0.51288(10) 0.85507(6) 0.02785(9) 0.0304(2) Uani 1 1 d . . . O3 O 0.22639(10) 0.87281(6) 0.30807(9) 0.0294(2) Uani 1 1 d . . . N1 N 0.85479(11) 1.08134(7) 0.47741(10) 0.0195(2) Uani 1 1 d . . . N2 N 0.65050(11) 1.00495(7) 0.40596(10) 0.0186(2) Uani 1 1 d . . . N3 N 0.57360(12) 0.92999(7) 0.21298(10) 0.0216(2) Uani 1 1 d . . . N4 N 0.43572(11) 0.93966(6) 0.35986(10) 0.0192(2) Uani 1 1 d . . . C1 C 0.98450(12) 1.12001(8) 0.48207(12) 0.0199(3) Uani 1 1 d . . . C2 C 1.04742(14) 1.11554(9) 0.38213(13) 0.0284(3) Uani 1 1 d . . . H2 H 1.0033 1.0852 0.3046 0.034 Uiso 1 1 calc R . . C3 C 1.17549(15) 1.15589(10) 0.39708(15) 0.0335(3) Uani 1 1 d . . . H3 H 1.2186 1.1524 0.3291 0.040 Uiso 1 1 calc R . . C4 C 1.24162(14) 1.20093(9) 0.50846(15) 0.0311(3) Uani 1 1 d . . . H4 H 1.3282 1.2290 0.5167 0.037 Uiso 1 1 calc R . . C5 C 1.17901(14) 1.20430(9) 0.60776(15) 0.0303(3) Uani 1 1 d . . . H5 H 1.2240 1.2343 0.6854 0.036 Uiso 1 1 calc R . . C6 C 1.05163(14) 1.16445(8) 0.59542(14) 0.0264(3) Uani 1 1 d . . . H6 H 1.0099 1.1674 0.6644 0.032 Uiso 1 1 calc R . . C7 C 0.77448(13) 1.03382(7) 0.38034(12) 0.0192(2) Uani 1 1 d . . . C8 C 0.54925(13) 0.95703(7) 0.32414(11) 0.0178(2) Uani 1 1 d . . . C9 C 0.33173(13) 0.89242(8) 0.27687(12) 0.0205(3) Uani 1 1 d . . . C10 C 0.33806(13) 0.86456(8) 0.14253(12) 0.0198(3) Uani 1 1 d . . . C11 C 0.48065(13) 0.88061(8) 0.12118(12) 0.0213(3) Uani 1 1 d . . . C12 C 0.30152(13) 0.77311(8) 0.12243(12) 0.0214(3) Uani 1 1 d . . . H12A H 0.2027 0.7644 0.1240 0.026 Uiso 1 1 calc R . . H12B H 0.3058 0.7564 0.0348 0.026 Uiso 1 1 calc R . . C13 C 0.40075(14) 0.72067(8) 0.22543(13) 0.0252(3) Uani 1 1 d . . . H13 H 0.3941 0.7231 0.3121 0.030 Uiso 1 1 calc R . . C14 C 0.49652(15) 0.67141(9) 0.20385(15) 0.0318(3) Uani 1 1 d . . . H14A H 0.5060 0.6675 0.1183 0.038 Uiso 1 1 calc R . . H14B H 0.5561 0.6398 0.2738 0.038 Uiso 1 1 calc R . . C15 C 0.22293(14) 0.91369(8) 0.03617(13) 0.0247(3) Uani 1 1 d . . . H15A H 0.2212 0.8942 -0.0519 0.030 Uiso 1 1 calc R . . H15B H 0.1282 0.9023 0.0462 0.030 Uiso 1 1 calc R . . C16 C 0.24661(16) 1.00380(9) 0.04276(14) 0.0313(3) Uani 1 1 d . . . H16 H 0.3245 1.0246 0.0180 0.038 Uiso 1 1 calc R . . C17 C 0.16624(18) 1.05566(10) 0.08074(17) 0.0436(4) Uani 1 1 d . . . H17A H 0.0876 1.0367 0.1061 0.052 Uiso 1 1 calc R . . H17B H 0.1867 1.1122 0.0829 0.052 Uiso 1 1 calc R . . H3N H 0.6564(18) 0.9441(10) 0.2045(16) 0.031(4) Uiso 1 1 d . . . H2N H 0.6288(16) 1.0206(10) 0.4751(16) 0.026(4) Uiso 1 1 d . . . H1N H 0.8240(17) 1.0914(10) 0.5443(16) 0.028(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0261(5) 0.0330(5) 0.0221(5) -0.0070(4) 0.0121(4) -0.0082(4) O2 0.0330(5) 0.0384(6) 0.0239(5) -0.0119(4) 0.0151(4) -0.0101(4) O3 0.0256(5) 0.0398(6) 0.0263(5) -0.0115(4) 0.0132(4) -0.0129(4) N1 0.0199(5) 0.0226(5) 0.0171(5) -0.0020(4) 0.0072(4) -0.0036(4) N2 0.0203(5) 0.0219(5) 0.0152(5) -0.0022(4) 0.0075(4) -0.0033(4) N3 0.0209(5) 0.0271(6) 0.0187(5) -0.0055(4) 0.0088(4) -0.0068(4) N4 0.0198(5) 0.0215(5) 0.0164(5) -0.0020(4) 0.0058(4) -0.0027(4) C1 0.0175(5) 0.0188(6) 0.0225(6) 0.0028(5) 0.0047(5) -0.0005(4) C2 0.0250(6) 0.0377(8) 0.0226(6) -0.0005(6) 0.0075(5) -0.0067(6) C3 0.0282(7) 0.0439(9) 0.0301(7) 0.0035(6) 0.0117(6) -0.0085(6) C4 0.0222(6) 0.0296(8) 0.0416(8) 0.0013(6) 0.0098(6) -0.0071(5) C5 0.0253(7) 0.0265(7) 0.0377(8) -0.0085(6) 0.0076(6) -0.0068(5) C6 0.0232(6) 0.0273(7) 0.0298(7) -0.0057(6) 0.0098(5) -0.0035(5) C7 0.0198(6) 0.0198(6) 0.0182(6) 0.0010(5) 0.0059(4) -0.0005(4) C8 0.0202(6) 0.0175(6) 0.0152(5) 0.0004(4) 0.0047(4) 0.0005(4) C9 0.0221(6) 0.0209(6) 0.0183(6) -0.0018(5) 0.0061(5) -0.0016(5) C10 0.0208(6) 0.0217(6) 0.0165(6) -0.0021(5) 0.0054(4) -0.0031(4) C11 0.0242(6) 0.0227(6) 0.0171(6) -0.0027(5) 0.0065(5) -0.0031(5) C12 0.0230(6) 0.0211(6) 0.0193(6) -0.0032(5) 0.0056(5) -0.0047(5) C13 0.0295(7) 0.0229(7) 0.0210(6) 0.0000(5) 0.0048(5) -0.0046(5) C14 0.0281(7) 0.0272(7) 0.0366(8) 0.0021(6) 0.0049(6) -0.0020(5) C15 0.0262(6) 0.0248(7) 0.0197(6) -0.0006(5) 0.0021(5) -0.0005(5) C16 0.0361(8) 0.0273(7) 0.0250(7) 0.0028(6) 0.0014(6) -0.0033(6) C17 0.0426(9) 0.0313(8) 0.0438(9) -0.0077(7) -0.0059(7) 0.0034(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.2277(15) . ? O2 C11 1.2123(15) . ? O3 C9 1.2282(15) . ? N1 C7 1.3445(16) . ? N1 C1 1.4153(15) . ? N1 H1N 0.875(17) . ? N2 C8 1.3577(15) . ? N2 C7 1.4149(15) . ? N2 H2N 0.870(16) . ? N3 C8 1.3584(16) . ? N3 C11 1.3811(16) . ? N3 H3N 0.879(17) . ? N4 C8 1.3210(16) . ? N4 C9 1.3711(15) . ? C1 C2 1.3937(18) . ? C1 C6 1.3949(18) . ? C2 C3 1.3913(19) . ? C2 H2 0.9500 . ? C3 C4 1.383(2) . ? C3 H3 0.9500 . ? C4 C5 1.385(2) . ? C4 H4 0.9500 . ? C5 C6 1.3863(18) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C9 C10 1.5275(17) . ? C10 C11 1.5156(17) . ? C10 C12 1.5460(17) . ? C10 C15 1.5611(17) . ? C12 C13 1.4995(18) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.318(2) . ? C13 H13 0.9500 . ? C14 H14A 0.9500 . ? C14 H14B 0.9500 . ? C15 C16 1.4986(19) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.311(2) . ? C16 H16 0.9500 . ? C17 H17A 0.9500 . ? C17 H17B 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 C7 N1 C1 126.77(11) . . ? C7 N1 H1N 118.1(11) . . ? C1 N1 H1N 115.1(11) . . ? C8 N2 C7 125.25(11) . . ? C8 N2 H2N 113.2(10) . . ? C7 N2 H2N 121.3(10) . . ? C8 N3 C11 123.83(11) . . ? C8 N3 H3N 115.1(11) . . ? C11 N3 H3N 121.0(11) . . ? C8 N4 C9 117.79(10) . . ? C2 C1 C6 119.34(12) . . ? C2 C1 N1 124.12(12) . . ? C6 C1 N1 116.55(11) . . ? C3 C2 C1 119.34(13) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C4 C3 C2 121.60(14) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 118.61(13) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C4 C5 C6 120.91(13) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 120.20(13) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O1 C7 N1 125.44(11) . . ? O1 C7 N2 122.01(11) . . ? N1 C7 N2 112.55(10) . . ? N4 C8 N2 117.34(11) . . ? N4 C8 N3 125.25(11) . . ? N2 C8 N3 117.41(11) . . ? O3 C9 N4 119.92(11) . . ? O3 C9 C10 117.42(11) . . ? N4 C9 C10 122.62(11) . . ? C11 C10 C9 113.51(10) . . ? C11 C10 C12 109.61(10) . . ? C9 C10 C12 110.32(10) . . ? C11 C10 C15 107.43(10) . . ? C9 C10 C15 107.35(10) . . ? C12 C10 C15 108.45(10) . . ? O2 C11 N3 120.25(12) . . ? O2 C11 C10 123.72(11) . . ? N3 C11 C10 115.98(10) . . ? C13 C12 C10 112.73(10) . . ? C13 C12 H12A 109.0 . . ? C10 C12 H12A 109.0 . . ? C13 C12 H12B 109.0 . . ? C10 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 124.42(13) . . ? C14 C13 H13 117.8 . . ? C12 C13 H13 117.8 . . ? C13 C14 H14A 120.0 . . ? C13 C14 H14B 120.0 . . ? H14A C14 H14B 120.0 . . ? C16 C15 C10 114.20(11) . . ? C16 C15 H15A 108.7 . . ? C10 C15 H15A 108.7 . . ? C16 C15 H15B 108.7 . . ? C10 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C17 C16 C15 123.89(16) . . ? C17 C16 H16 118.1 . . ? C15 C16 H16 118.1 . . ? C16 C17 H17A 120.0 . . ? C16 C17 H17B 120.0 . . ? H17A C17 H17B 120.0 . . ? 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 N3 H3N O1 0.879(17) 1.842(17) 2.5676(14) 138.4(15) . N2 H2N N4 0.870(16) 2.154(16) 3.0233(15) 177.1(14) 3_676 N1 H1N O3 0.875(17) 1.889(17) 2.7582(14) 171.6(15) 3_676 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.324 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.046 # Attachment 'Compound_3.cif' data_aek002 _database_code_depnum_ccdc_archive 'CCDC 670608' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(5,5-Diallyl-4,6-dioxotetrahydropyrimidin-ylidene)- 3-naphthalen-2-ylurea ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H20 N4 O3' _chemical_formula_weight 376.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.798(2) _cell_length_b 6.866(1) _cell_length_c 19.102(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.998(2) _cell_angle_gamma 90.00 _cell_volume 1807.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8857 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 28.41 _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9793 _exptl_absorpt_correction_T_max 0.9885 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5 deg. in omega, colllected at phi = 0.00, 90.00 and 180.00 deg. and 2 sets of 800 frames, each of width 0.45 deg in phi, collected at omega = -30.00 and 210.00 deg. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-AXS Smart APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30103 _diffrn_reflns_av_R_equivalents 0.0637 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 28.42 _reflns_number_total 4516 _reflns_number_gt 3354 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART (Bruker-AXS, 2000)' _computing_cell_refinement 'Bruker SMART (Bruker-AXS, 2000)' _computing_data_reduction 'Bruker SAINT+ (Bruker-AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker-AXS, 2000a)' _computing_publication_material 'Bruker SHELXTL (Bruker-AXS, 2000a)' _publ_section_references ; Bruker-AXS (2000). SMART, Version 5.625, Madison, WI. Bruker-AXS (2000a). SHELXTL, Version 6.10, Madison, WI. Bruker-AXS (2004). SAINT+, Version 7.03, Madison, WI Sheldrick, G. M. (1997). SHELXS-97 and SHELXL-97. University of G\"ottingen, Germany. Sheldrick, G, M. (2002). SADABS, Version 2.05. University of G\"ottingen, Germany. ; _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. H-atoms attached to nitrogen were located in difference maps and refined with isotropic displacement parameters. Those attached to carbon were were placed in calculated positions (C---H = 0.95 - 0.98 \%A) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms. ; _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^)+(0.0648P)^2^+1.1824P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4516 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0908 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.1557 _refine_ls_wR_factor_gt 0.1442 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 O1 O 0.47518(11) -0.0385(2) 0.11056(8) 0.0312(4) Uani 1 1 d . . . O2 O 0.20576(10) 0.1810(2) 0.15765(8) 0.0285(4) Uani 1 1 d . . . O3 O 0.27944(10) 0.7545(2) 0.03569(8) 0.0280(4) Uani 1 1 d . . . N1 N 0.62130(12) 0.0420(3) 0.07080(9) 0.0213(4) Uani 1 1 d . . . H1N H 0.6476(15) 0.122(3) 0.0439(11) 0.012(5) Uiso 1 1 d . . . N2 N 0.49623(12) 0.2592(2) 0.05262(9) 0.0212(4) Uani 1 1 d . . . N3 N 0.34433(13) 0.2192(3) 0.10317(9) 0.0240(4) Uani 1 1 d . . . H3N H 0.3693(19) 0.098(4) 0.1153(14) 0.041(7) Uiso 1 1 d . . . N4 N 0.38358(12) 0.5045(3) 0.04568(9) 0.0216(4) Uani 1 1 d . . . H4N H 0.4192(18) 0.574(4) 0.0182(14) 0.036(7) Uiso 1 1 d . . . C1 C 0.77312(14) -0.0746(3) 0.12731(10) 0.0203(4) Uani 1 1 d . . . C2 C 0.81904(15) 0.1076(3) 0.12018(11) 0.0244(4) Uani 1 1 d . . . H2 H 0.7837 0.2124 0.0987 0.029 Uiso 1 1 calc R . . C3 C 0.91342(15) 0.1366(3) 0.14350(11) 0.0268(5) Uani 1 1 d . . . H3 H 0.9423 0.2611 0.1386 0.032 Uiso 1 1 calc R . . C4 C 0.96789(16) -0.0162(3) 0.17460(11) 0.0291(5) Uani 1 1 d . . . H4 H 1.0342 0.0032 0.1888 0.035 Uiso 1 1 calc R . . C5 C 0.92526(16) -0.1919(3) 0.18425(11) 0.0275(5) Uani 1 1 d . . . H5 H 0.9621 -0.2936 0.2064 0.033 Uiso 1 1 calc R . . C6 C 0.82697(15) -0.2271(3) 0.16198(10) 0.0235(4) Uani 1 1 d . . . C7 C 0.78159(16) -0.4072(3) 0.17315(11) 0.0271(5) Uani 1 1 d . . . H7 H 0.8166 -0.5080 0.1974 0.033 Uiso 1 1 calc R . . C8 C 0.68797(16) -0.4385(3) 0.14962(11) 0.0264(5) Uani 1 1 d . . . H8 H 0.6585 -0.5611 0.1575 0.032 Uiso 1 1 calc R . . C9 C 0.63435(15) -0.2916(3) 0.11378(11) 0.0241(4) Uani 1 1 d . . . H9 H 0.5696 -0.3168 0.0968 0.029 Uiso 1 1 calc R . . C10 C 0.67495(14) -0.1123(3) 0.10324(10) 0.0207(4) Uani 1 1 d . . . C11 C 0.52688(15) 0.0771(3) 0.08004(10) 0.0217(4) Uani 1 1 d . . . C12 C 0.41050(14) 0.3218(3) 0.06749(10) 0.0202(4) Uani 1 1 d . . . C13 C 0.25740(14) 0.2873(3) 0.12610(10) 0.0233(4) Uani 1 1 d . . . C14 C 0.23364(14) 0.5004(3) 0.11222(10) 0.0220(4) Uani 1 1 d . . . C15 C 0.29919(14) 0.5973(3) 0.06124(10) 0.0215(4) Uani 1 1 d . . . C16 C 0.12802(15) 0.5134(3) 0.08249(11) 0.0261(5) Uani 1 1 d . . . H16A H 0.0845 0.4571 0.1168 0.031 Uiso 1 1 calc R . . H16B H 0.1102 0.6520 0.0757 0.031 Uiso 1 1 calc R . . C17 C 0.11320(15) 0.4076(4) 0.01391(11) 0.0293(5) Uani 1 1 d . . . H17 H 0.1282 0.4750 -0.0276 0.035 Uiso 1 1 calc R . . C18 C 0.08079(16) 0.2278(4) 0.00743(12) 0.0339(5) Uani 1 1 d . . . H18A H 0.0651 0.1562 0.0478 0.041 Uiso 1 1 calc R . . H18B H 0.0731 0.1698 -0.0377 0.041 Uiso 1 1 calc R . . C19 C 0.24615(16) 0.6088(3) 0.18385(11) 0.0289(5) Uani 1 1 d . . . H19A H 0.2425 0.7510 0.1754 0.035 Uiso 1 1 calc R . . H19B H 0.1918 0.5729 0.2131 0.035 Uiso 1 1 calc R . . C20 C 0.34215(19) 0.5618(4) 0.22414(12) 0.0387(6) Uani 1 1 d . . . H20 H 0.3498 0.4346 0.2432 0.046 Uiso 1 1 calc R . . C21 C 0.4128(2) 0.6808(5) 0.23407(13) 0.0527(8) Uani 1 1 d . . . H21A H 0.4079 0.8093 0.2158 0.063 Uiso 1 1 calc R . . H21B H 0.4702 0.6406 0.2597 0.063 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0246(8) 0.0276(8) 0.0422(9) 0.0124(7) 0.0095(6) 0.0027(7) O2 0.0259(8) 0.0319(9) 0.0283(8) 0.0058(7) 0.0094(6) -0.0026(7) O3 0.0253(8) 0.0263(8) 0.0333(8) 0.0062(7) 0.0093(6) 0.0045(6) N1 0.0211(9) 0.0182(9) 0.0249(9) 0.0041(7) 0.0044(7) -0.0007(7) N2 0.0201(9) 0.0206(9) 0.0231(8) 0.0019(7) 0.0041(6) 0.0016(7) N3 0.0221(9) 0.0235(9) 0.0271(9) 0.0060(7) 0.0072(7) 0.0035(7) N4 0.0200(9) 0.0230(9) 0.0224(8) 0.0022(7) 0.0069(6) -0.0017(7) C1 0.0230(10) 0.0214(10) 0.0169(9) -0.0014(7) 0.0036(7) 0.0030(8) C2 0.0247(11) 0.0224(10) 0.0263(10) -0.0022(8) 0.0054(8) 0.0017(9) C3 0.0253(11) 0.0267(11) 0.0286(11) -0.0062(9) 0.0048(8) -0.0033(9) C4 0.0232(11) 0.0373(13) 0.0265(11) -0.0083(9) -0.0007(8) 0.0007(9) C5 0.0279(11) 0.0328(12) 0.0218(10) -0.0010(9) -0.0006(8) 0.0096(9) C6 0.0282(11) 0.0235(11) 0.0188(9) -0.0024(8) 0.0031(8) 0.0037(9) C7 0.0351(12) 0.0219(11) 0.0242(10) 0.0015(8) 0.0007(8) 0.0067(9) C8 0.0331(12) 0.0179(10) 0.0288(11) 0.0002(8) 0.0060(9) -0.0008(9) C9 0.0249(11) 0.0213(10) 0.0260(10) -0.0030(8) 0.0019(8) -0.0007(8) C10 0.0229(10) 0.0190(10) 0.0203(9) -0.0008(8) 0.0030(7) 0.0023(8) C11 0.0226(10) 0.0212(10) 0.0215(9) 0.0008(8) 0.0028(7) 0.0002(8) C12 0.0196(10) 0.0231(10) 0.0180(9) 0.0001(8) 0.0020(7) -0.0025(8) C13 0.0210(10) 0.0283(11) 0.0209(9) 0.0014(8) 0.0028(7) -0.0015(8) C14 0.0202(10) 0.0261(11) 0.0203(9) -0.0006(8) 0.0060(7) 0.0005(8) C15 0.0210(10) 0.0239(11) 0.0199(9) 0.0001(8) 0.0024(7) -0.0012(8) C16 0.0207(10) 0.0262(11) 0.0320(11) -0.0002(9) 0.0062(8) 0.0017(9) C17 0.0242(11) 0.0386(13) 0.0248(10) 0.0042(9) 0.0003(8) 0.0002(10) C18 0.0301(12) 0.0424(14) 0.0296(11) -0.0048(10) 0.0057(9) -0.0004(11) C19 0.0322(12) 0.0312(12) 0.0240(10) -0.0052(9) 0.0084(8) -0.0030(10) C20 0.0438(15) 0.0471(15) 0.0259(11) -0.0056(11) 0.0088(10) -0.0034(12) C21 0.0551(18) 0.072(2) 0.0314(13) 0.0030(13) 0.0026(12) -0.0145(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 O1 C11 1.234(2) . ? O2 C13 1.204(2) . ? O3 C15 1.210(2) . ? N1 C11 1.346(3) . ? N1 C10 1.416(3) . ? N1 H1N 0.84(2) . ? N2 C12 1.304(2) . ? N2 C11 1.412(3) . ? N3 C12 1.364(2) . ? N3 C13 1.380(3) . ? N3 H3N 0.93(3) . ? N4 C12 1.367(3) . ? N4 C15 1.373(3) . ? N4 H4N 0.88(3) . ? C1 C2 1.412(3) . ? C1 C6 1.427(3) . ? C1 C10 1.431(3) . ? C2 C3 1.369(3) . ? C2 H2 0.9500 . ? C3 C4 1.404(3) . ? C3 H3 0.9500 . ? C4 C5 1.359(3) . ? C4 H4 0.9500 . ? C5 C6 1.421(3) . ? C5 H5 0.9500 . ? C6 C7 1.407(3) . ? C7 C8 1.363(3) . ? C7 H7 0.9500 . ? C8 C9 1.407(3) . ? C8 H8 0.9500 . ? C9 C10 1.372(3) . ? C9 H9 0.9500 . ? C13 C14 1.520(3) . ? C14 C15 1.517(3) . ? C14 C16 1.539(3) . ? C14 C19 1.559(3) . ? C16 C17 1.502(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.316(3) . ? C17 H17 0.9500 . ? C18 H18A 0.9500 . ? C18 H18B 0.9500 . ? C19 C20 1.531(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.279(4) . ? C20 H20 0.9500 . ? C21 H21A 0.9500 . ? C21 H21B 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 C11 N1 C10 124.33(17) . . ? C11 N1 H1N 114.4(14) . . ? C10 N1 H1N 121.2(14) . . ? C12 N2 C11 117.97(17) . . ? C12 N3 C13 126.81(19) . . ? C12 N3 H3N 109.9(17) . . ? C13 N3 H3N 122.9(17) . . ? C12 N4 C15 125.41(17) . . ? C12 N4 H4N 122.1(17) . . ? C15 N4 H4N 112.5(17) . . ? C2 C1 C6 118.00(18) . . ? C2 C1 C10 123.45(18) . . ? C6 C1 C10 118.53(18) . . ? C3 C2 C1 121.4(2) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 120.5(2) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 119.7(2) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 121.6(2) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C7 C6 C5 121.97(19) . . ? C7 C6 C1 119.35(19) . . ? C5 C6 C1 118.69(19) . . ? C8 C7 C6 120.7(2) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 120.8(2) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C10 C9 C8 120.4(2) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 N1 121.84(18) . . ? C9 C10 C1 120.14(18) . . ? N1 C10 C1 117.99(18) . . ? O1 C11 N1 122.30(19) . . ? O1 C11 N2 125.14(18) . . ? N1 C11 N2 112.54(17) . . ? N2 C12 N3 125.24(19) . . ? N2 C12 N4 118.13(17) . . ? N3 C12 N4 116.64(17) . . ? O2 C13 N3 120.0(2) . . ? O2 C13 C14 122.91(19) . . ? N3 C13 C14 117.00(18) . . ? C15 C14 C13 113.81(16) . . ? C15 C14 C16 108.83(16) . . ? C13 C14 C16 108.15(17) . . ? C15 C14 C19 108.17(17) . . ? C13 C14 C19 107.07(17) . . ? C16 C14 C19 110.82(16) . . ? O3 C15 N4 120.14(18) . . ? O3 C15 C14 121.39(18) . . ? N4 C15 C14 118.46(18) . . ? C17 C16 C14 112.14(17) . . ? C17 C16 H16A 109.2 . . ? C14 C16 H16A 109.2 . . ? C17 C16 H16B 109.2 . . ? C14 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C18 C17 C16 124.4(2) . . ? C18 C17 H17 117.8 . . ? C16 C17 H17 117.8 . . ? C17 C18 H18A 120.0 . . ? C17 C18 H18B 120.0 . . ? H18A C18 H18B 120.0 . . ? C20 C19 C14 113.18(18) . . ? C20 C19 H19A 108.9 . . ? C14 C19 H19A 108.9 . . ? C20 C19 H19B 108.9 . . ? C14 C19 H19B 108.9 . . ? H19A C19 H19B 107.8 . . ? C21 C20 C19 125.0(3) . . ? C21 C20 H20 117.5 . . ? C19 C20 H20 117.5 . . ? C20 C21 H21A 120.0 . . ? C20 C21 H21B 120.0 . . ? H21A C21 H21B 120.0 . . ? 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 C6 C1 C2 C3 2.2(3) . . . . ? C10 C1 C2 C3 -179.46(19) . . . . ? C1 C2 C3 C4 0.8(3) . . . . ? C2 C3 C4 C5 -2.8(3) . . . . ? C3 C4 C5 C6 1.6(3) . . . . ? C4 C5 C6 C7 -178.5(2) . . . . ? C4 C5 C6 C1 1.4(3) . . . . ? C2 C1 C6 C7 176.70(18) . . . . ? C10 C1 C6 C7 -1.7(3) . . . . ? C2 C1 C6 C5 -3.3(3) . . . . ? C10 C1 C6 C5 178.31(18) . . . . ? C5 C6 C7 C8 -178.29(19) . . . . ? C1 C6 C7 C8 1.7(3) . . . . ? C6 C7 C8 C9 -0.2(3) . . . . ? C7 C8 C9 C10 -1.4(3) . . . . ? C8 C9 C10 N1 -176.48(18) . . . . ? C8 C9 C10 C1 1.4(3) . . . . ? C11 N1 C10 C9 36.8(3) . . . . ? C11 N1 C10 C1 -141.1(2) . . . . ? C2 C1 C10 C9 -178.15(19) . . . . ? C6 C1 C10 C9 0.2(3) . . . . ? C2 C1 C10 N1 -0.2(3) . . . . ? C6 C1 C10 N1 178.12(17) . . . . ? C10 N1 C11 O1 -9.9(3) . . . . ? C10 N1 C11 N2 168.76(17) . . . . ? C12 N2 C11 O1 8.6(3) . . . . ? C12 N2 C11 N1 -170.07(18) . . . . ? C11 N2 C12 N3 -5.3(3) . . . . ? C11 N2 C12 N4 174.97(17) . . . . ? C13 N3 C12 N2 172.81(19) . . . . ? C13 N3 C12 N4 -7.4(3) . . . . ? C15 N4 C12 N2 -175.08(18) . . . . ? C15 N4 C12 N3 5.2(3) . . . . ? C12 N3 C13 O2 -179.45(19) . . . . ? C12 N3 C13 C14 -1.9(3) . . . . ? O2 C13 C14 C15 -170.06(19) . . . . ? N3 C13 C14 C15 12.5(3) . . . . ? O2 C13 C14 C16 -49.0(3) . . . . ? N3 C13 C14 C16 133.54(18) . . . . ? O2 C13 C14 C19 70.5(2) . . . . ? N3 C13 C14 C19 -107.0(2) . . . . ? C12 N4 C15 O3 -175.39(19) . . . . ? C12 N4 C15 C14 6.1(3) . . . . ? C13 C14 C15 O3 167.03(18) . . . . ? C16 C14 C15 O3 46.4(3) . . . . ? C19 C14 C15 O3 -74.1(2) . . . . ? C13 C14 C15 N4 -14.5(3) . . . . ? C16 C14 C15 N4 -135.21(19) . . . . ? C19 C14 C15 N4 104.3(2) . . . . ? C15 C14 C16 C17 62.1(2) . . . . ? C13 C14 C16 C17 -62.1(2) . . . . ? C19 C14 C16 C17 -179.12(18) . . . . ? C14 C16 C17 C18 95.9(3) . . . . ? C15 C14 C19 C20 -74.3(2) . . . . ? C13 C14 C19 C20 48.8(2) . . . . ? C16 C14 C19 C20 166.51(19) . . . . ? C14 C19 C20 C21 110.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4N N2 0.88(3) 2.16(3) 3.039(2) 178(2) 3_665 N3 H3N O1 0.93(3) 1.74(3) 2.527(2) 141(2) . N1 H1N O3 0.84(2) 2.05(2) 2.874(2) 164(2) 3_665 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.42 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.670 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.074 # Attachment 'Compound_4.cif' data_aek006 _database_code_depnum_ccdc_archive 'CCDC 670609' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(5,5-Diallyl-4,6-dioxo-1,4,5,6-tetrahydropyrimidin- 2-yl)-3-(2-naphthyl)urea ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H20 N4 O3' _chemical_formula_sum 'C21 H20 N4 O3' _chemical_formula_weight 376.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall 'P -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.318(1) _cell_length_b 15.813(2) _cell_length_c 10.762(1) _cell_angle_alpha 90.00 _cell_angle_beta 112.778(1) _cell_angle_gamma 90.00 _cell_volume 1932.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 7690 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 28.32 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9303 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; The diffraction data were collected in three sets of 606 frames (0.3 deg. width in omega) at phi = 0, 120 and 240 deg. A scan time of 60 sec/frame was used. ; _diffrn_ambient_temperature 200(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-AXS Smart APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16918 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 28.32 _reflns_number_total 4622 _reflns_number_gt 3472 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2 (Bruker-AXS, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker-AXS, 2006)' _computing_data_reduction 'Bruker SAINT+ (Bruker-AXS, 2006a)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker APEX2 (Bruker-AXS, 2006)' _computing_publication_material 'Bruker APEX2 (Bruker-AXS, 2006)' _publ_section_references ; Bruker-AXS (2006). APEX2, Version 2.1-0, Madison, WI. Bruker-AXS (2006a). SAINT+, Version 7.34A, Madison, WI Sheldrick, G. M. (1997). SHELXS-97 and SHELXL-97. University of G\"ottingen, Germany. Sheldrick, G, M. (2007). SADABS, Version 2007/2. University of G\"ottingen, Germany. ; _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. H-atoms attached to carbon were placed in calculated positions (C---H = 0.95 - 0.98 \%A) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms. Those attached to nitrogen were located in a difference map and refined with isotropic displacement paramters. ; _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^)+(0.0589P)^2^+0.5078P] 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 SHELXL _refine_ls_extinction_coef 0.0176(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4622 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1301 _refine_ls_wR_factor_gt 0.1174 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.27031(10) -0.01708(8) 0.71731(10) 0.0469(3) Uani 1 1 d . . . O2 O 0.53929(12) 0.11910(9) 1.00682(12) 0.0642(4) Uani 1 1 d . . . O3 O 0.75115(10) 0.10973(9) 0.72344(12) 0.0596(4) Uani 1 1 d . . . N1 N 0.20952(11) -0.07519(8) 0.50790(12) 0.0354(3) Uani 1 1 d . . . N2 N 0.38929(10) -0.00925(8) 0.59657(12) 0.0337(3) Uani 1 1 d . . . N3 N 0.57195(10) 0.05007(8) 0.65653(11) 0.0355(3) Uani 1 1 d . . . N4 N 0.47190(12) 0.05472(9) 0.80586(12) 0.0418(3) Uani 1 1 d . . . C1 C 0.09678(12) -0.10514(9) 0.49339(14) 0.0355(3) Uani 1 1 d . . . C2 C 0.03376(14) -0.14814(11) 0.37158(17) 0.0495(4) Uani 1 1 d . . . H2 H 0.0685 -0.1561 0.3075 0.059 Uiso 1 1 calc R . . C3 C -0.07646(16) -0.17829(13) 0.34546(19) 0.0571(5) Uani 1 1 d . . . H3 H -0.1178 -0.2068 0.2629 0.068 Uiso 1 1 calc R . . C4 C -0.13067(14) -0.16801(10) 0.43864(18) 0.0452(4) Uani 1 1 d . . . C5 C -0.24572(15) -0.19806(12) 0.4146(2) 0.0565(5) Uani 1 1 d . . . H5 H -0.2888 -0.2270 0.3329 0.068 Uiso 1 1 calc R . . C6 C -0.29541(15) -0.18618(12) 0.5060(2) 0.0548(5) Uani 1 1 d . . . H6 H -0.3720 -0.2076 0.4887 0.066 Uiso 1 1 calc R . . C7 C -0.23363(15) -0.14232(12) 0.6262(2) 0.0543(5) Uani 1 1 d . . . H7 H -0.2692 -0.1333 0.6893 0.065 Uiso 1 1 calc R . . C8 C -0.12261(15) -0.11245(12) 0.65303(17) 0.0498(4) Uani 1 1 d . . . H8 H -0.0818 -0.0829 0.7348 0.060 Uiso 1 1 calc R . . C9 C -0.06755(13) -0.12497(10) 0.56070(16) 0.0398(3) Uani 1 1 d . . . C10 C 0.04724(13) -0.09379(10) 0.58648(15) 0.0393(3) Uani 1 1 d . . . H10 H 0.0899 -0.0650 0.6684 0.047 Uiso 1 1 calc R . . C11 C 0.28563(13) -0.03333(9) 0.61410(14) 0.0343(3) Uani 1 1 d . . . C12 C 0.48105(12) 0.03294(9) 0.68822(13) 0.0330(3) Uani 1 1 d . . . C13 C 0.55649(15) 0.09925(11) 0.90729(15) 0.0436(4) Uani 1 1 d . . . C14 C 0.66809(13) 0.11994(10) 0.88685(14) 0.0400(4) Uani 1 1 d . . . C15 C 0.66524(14) 0.09244(10) 0.74920(15) 0.0407(4) Uani 1 1 d . . . C16 C 0.68825(15) 0.21704(10) 0.90162(16) 0.0449(4) Uani 1 1 d . . . H16A H 0.6859 0.2353 0.9885 0.054 Uiso 1 1 calc R . . H16B H 0.7677 0.2300 0.9040 0.054 Uiso 1 1 calc R . . C17 C 0.59934(17) 0.26649(11) 0.79039(17) 0.0520(4) Uani 1 1 d . . . H17 H 0.6069 0.2669 0.7058 0.062 Uiso 1 1 calc R . . C18 C 0.51254(18) 0.30894(13) 0.7996(2) 0.0650(5) Uani 1 1 d . . . H18A H 0.5018 0.3102 0.8824 0.078 Uiso 1 1 calc R . . H18B H 0.4598 0.3388 0.7236 0.078 Uiso 1 1 calc R . . C19 C 0.77157(16) 0.07450(12) 0.99935(16) 0.0513(4) Uani 1 1 d . . . H19A H 0.8462 0.0915 0.9919 0.062 Uiso 1 1 calc R . . H19B H 0.7746 0.0943 1.0879 0.062 Uiso 1 1 calc R . . C20 C 0.7641(2) -0.02044(14) 0.9958(2) 0.0676(6) Uani 1 1 d . . . H20 H 0.6952 -0.0452 0.9996 0.081 Uiso 1 1 calc R . . C21 C 0.8422(3) -0.07026(19) 0.9882(3) 0.1000(9) Uani 1 1 d . . . H21A H 0.9125 -0.0481 0.9842 0.120 Uiso 1 1 calc R . . H21B H 0.8304 -0.1297 0.9865 0.120 Uiso 1 1 calc R . . H1N H 0.2297(14) -0.0836(10) 0.4374(17) 0.041(4) Uiso 1 1 d . . . H2N H 0.3980(14) -0.0209(10) 0.5224(18) 0.040(4) Uiso 1 1 d . . . H4N H 0.4023(18) 0.0367(12) 0.811(2) 0.061(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0469(6) 0.0652(7) 0.0348(6) -0.0105(5) 0.0227(5) -0.0148(5) O2 0.0698(9) 0.0933(10) 0.0407(6) -0.0276(6) 0.0337(6) -0.0326(7) O3 0.0484(7) 0.0936(10) 0.0450(7) -0.0279(6) 0.0270(6) -0.0296(7) N1 0.0339(6) 0.0424(7) 0.0311(6) -0.0033(5) 0.0139(5) -0.0042(5) N2 0.0367(7) 0.0396(7) 0.0271(6) -0.0045(5) 0.0148(5) -0.0057(5) N3 0.0364(6) 0.0429(7) 0.0283(6) -0.0063(5) 0.0138(5) -0.0067(5) N4 0.0446(8) 0.0545(8) 0.0314(6) -0.0101(5) 0.0201(6) -0.0163(6) C1 0.0332(7) 0.0365(8) 0.0360(7) 0.0011(6) 0.0127(6) -0.0004(6) C2 0.0425(9) 0.0600(10) 0.0490(9) -0.0162(8) 0.0211(7) -0.0102(8) C3 0.0447(10) 0.0689(12) 0.0582(11) -0.0241(9) 0.0205(8) -0.0155(8) C4 0.0365(8) 0.0419(9) 0.0570(10) -0.0022(7) 0.0180(7) -0.0024(6) C5 0.0404(9) 0.0565(11) 0.0721(12) -0.0094(9) 0.0213(9) -0.0080(8) C6 0.0371(9) 0.0551(10) 0.0749(13) 0.0084(9) 0.0247(9) -0.0012(7) C7 0.0451(10) 0.0626(11) 0.0622(11) 0.0145(9) 0.0287(9) 0.0046(8) C8 0.0434(9) 0.0631(11) 0.0461(9) 0.0076(8) 0.0207(7) -0.0002(8) C9 0.0363(8) 0.0405(8) 0.0425(8) 0.0094(6) 0.0153(6) 0.0033(6) C10 0.0361(8) 0.0463(8) 0.0341(7) 0.0022(6) 0.0120(6) -0.0023(6) C11 0.0358(7) 0.0367(7) 0.0315(7) 0.0006(6) 0.0143(6) -0.0023(6) C12 0.0392(8) 0.0336(7) 0.0272(6) -0.0011(5) 0.0138(6) -0.0028(6) C13 0.0512(9) 0.0519(9) 0.0311(7) -0.0085(6) 0.0196(7) -0.0129(7) C14 0.0417(8) 0.0499(9) 0.0285(7) -0.0089(6) 0.0138(6) -0.0107(7) C15 0.0410(8) 0.0511(9) 0.0325(7) -0.0084(6) 0.0171(6) -0.0088(7) C16 0.0491(9) 0.0509(9) 0.0354(8) -0.0101(7) 0.0170(7) -0.0139(7) C17 0.0626(11) 0.0513(10) 0.0439(9) -0.0061(7) 0.0225(8) -0.0131(8) C18 0.0560(12) 0.0589(12) 0.0764(14) -0.0027(10) 0.0216(10) -0.0107(9) C19 0.0528(10) 0.0616(11) 0.0342(8) -0.0063(7) 0.0112(7) -0.0035(8) C20 0.0779(14) 0.0683(13) 0.0513(11) -0.0011(9) 0.0192(10) -0.0010(11) C21 0.107(2) 0.0783(17) 0.107(2) -0.0133(15) 0.0327(18) 0.0076(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 O1 C11 1.2238(17) . ? O2 C13 1.2110(18) . ? O3 C15 1.2242(18) . ? N1 C11 1.3392(18) . ? N1 C1 1.4175(18) . ? N1 H1N 0.895(17) . ? N2 C12 1.3536(18) . ? N2 C11 1.4133(18) . ? N2 H2N 0.865(17) . ? N3 C12 1.3188(18) . ? N3 C15 1.3699(18) . ? N4 C12 1.3581(18) . ? N4 C13 1.3756(19) . ? N4 H4N 0.93(2) . ? C1 C10 1.372(2) . ? C1 C2 1.413(2) . ? C2 C3 1.362(2) . ? C2 H2 0.9500 . ? C3 C4 1.413(2) . ? C3 H3 0.9500 . ? C4 C9 1.415(2) . ? C4 C5 1.420(2) . ? C5 C6 1.358(3) . ? C5 H5 0.9500 . ? C6 C7 1.404(3) . ? C6 H6 0.9500 . ? C7 C8 1.368(2) . ? C7 H7 0.9500 . ? C8 C9 1.417(2) . ? C8 H8 0.9500 . ? C9 C10 1.420(2) . ? C10 H10 0.9500 . ? C13 C14 1.510(2) . ? C14 C15 1.5311(19) . ? C14 C19 1.553(2) . ? C14 C16 1.554(2) . ? C16 C17 1.493(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.299(3) . ? C17 H17 0.9500 . ? C18 H18A 0.9500 . ? C18 H18B 0.9500 . ? C19 C20 1.504(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.270(3) . ? C20 H20 0.9500 . ? C21 H21A 0.9500 . ? C21 H21B 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 C11 N1 C1 126.26(12) . . ? C11 N1 H1N 117.7(11) . . ? C1 N1 H1N 116.0(11) . . ? C12 N2 C11 125.33(12) . . ? C12 N2 H2N 114.2(11) . . ? C11 N2 H2N 120.5(11) . . ? C12 N3 C15 117.97(12) . . ? C12 N4 C13 123.97(13) . . ? C12 N4 H4N 113.0(12) . . ? C13 N4 H4N 123.1(12) . . ? C10 C1 C2 120.05(14) . . ? C10 C1 N1 124.73(13) . . ? C2 C1 N1 115.22(13) . . ? C3 C2 C1 120.39(15) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 121.38(16) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C3 C4 C9 118.25(14) . . ? C3 C4 C5 123.00(16) . . ? C9 C4 C5 118.75(16) . . ? C6 C5 C4 121.29(18) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 120.01(16) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 120.42(17) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 120.96(17) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C4 C9 C8 118.56(14) . . ? C4 C9 C10 119.74(14) . . ? C8 C9 C10 121.68(15) . . ? C1 C10 C9 120.19(14) . . ? C1 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? O1 C11 N1 125.12(13) . . ? O1 C11 N2 121.96(13) . . ? N1 C11 N2 112.92(12) . . ? N3 C12 N2 117.77(12) . . ? N3 C12 N4 125.04(13) . . ? N2 C12 N4 117.19(13) . . ? O2 C13 N4 119.77(15) . . ? O2 C13 C14 123.61(14) . . ? N4 C13 C14 116.62(12) . . ? C13 C14 C15 113.47(12) . . ? C13 C14 C19 107.76(13) . . ? C15 C14 C19 109.11(13) . . ? C13 C14 C16 108.53(13) . . ? C15 C14 C16 108.81(12) . . ? C19 C14 C16 109.09(13) . . ? O3 C15 N3 119.95(13) . . ? O3 C15 C14 117.24(13) . . ? N3 C15 C14 122.81(13) . . ? C17 C16 C14 113.40(13) . . ? C17 C16 H16A 108.9 . . ? C14 C16 H16A 108.9 . . ? C17 C16 H16B 108.9 . . ? C14 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C18 C17 C16 125.42(18) . . ? C18 C17 H17 117.3 . . ? C16 C17 H17 117.3 . . ? C17 C18 H18A 120.0 . . ? C17 C18 H18B 120.0 . . ? H18A C18 H18B 120.0 . . ? C20 C19 C14 114.74(15) . . ? C20 C19 H19A 108.6 . . ? C14 C19 H19A 108.6 . . ? C20 C19 H19B 108.6 . . ? C14 C19 H19B 108.6 . . ? H19A C19 H19B 107.6 . . ? C21 C20 C19 125.5(2) . . ? C21 C20 H20 117.3 . . ? C19 C20 H20 117.3 . . ? C20 C21 H21A 120.0 . . ? C20 C21 H21B 120.0 . . ? H21A C21 H21B 120.0 . . ? 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 H1N O3 0.895(17) 1.881(18) 2.7686(17) 171.0(15) 3_656 N2 H2N N3 0.865(17) 2.147(18) 3.0118(17) 177.5(15) 3_656 N4 H4N O1 0.93(2) 1.76(2) 2.5556(17) 141.7(18) . _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.380 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.043