Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Desiraju, Gautam R.' 'Jaskolski, Mariusz' 'Thaimattam, Ram' 'Vishweshwar, Peddy' _publ_contact_author_name 'Prof Gautam R. Desiraju' _publ_contact_author_address ; Prof Gautam R. Desiraju School of Chemistry University of Hyderabad PO Central University Hyderabad 500046 INDIA ; _publ_contact_author_email 'DESIRAJU@UOHYD.ERNET.IN' _publ_section_title ; Supramolecular synthons based on N-H...N and C-H...O hydrogen bonds. Crystal engineering of a helical structure with 5,5-diethylbarbituric acid. ; data_acr _database_code_CSD 186035 _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1:2 molecular complex of 5,5-diethylbarbituric acid and acridine' ; _chemical_name_common '1:2 molecular complex of 5,5-diethylbarbituric acid and acridine' _chemical_melting_point '448 K' _chemical_formula_sum 'C34 H30 N4 O3' _chemical_formula_weight 542.62 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 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 18.249(4) _cell_length_b 16.260(3) _cell_length_c 10.053(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.47(3) _cell_angle_gamma 90.00 _cell_volume 2776.0(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100K _cell_measurement_reflns_used 1250 _exptl_crystal_description needle _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 100K _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KUMA CCD detector [KUMA-1]' _diffrn_measurement_method '/w scans' _diffrn_reflns_number 8781 _diffrn_reflns_av_R_equivalents 0.0457 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3138 _reflns_number_gt 2597 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KUMA-1' _computing_data_reduction 'KM4-RED [KUMA-2]' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTON (Spek, 1992)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0512P)^2^+0.4468P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0032(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3138 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1063 _refine_ls_wR_factor_gt 0.0996 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_restrained_S_all 1.150 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5000 0.15189(8) 0.7500 0.0217(3) Uani 1 2 d S . . O2 O 0.39619(5) 0.38812(6) 0.83857(10) 0.0242(2) Uani 1 1 d . . . N1 N 0.44491(6) 0.27128(6) 0.78402(11) 0.0171(2) Uani 1 1 d . . . H1A H 0.4058(10) 0.2435(11) 0.7986(17) 0.033(4) Uiso 1 1 d . . . N2 N 0.31489(6) 0.18559(6) 0.82960(10) 0.0158(2) Uani 1 1 d . . . C1 C 0.5000 0.22656(11) 0.7500 0.0166(4) Uani 1 2 d S . . C2 C 0.44347(7) 0.35541(8) 0.79599(13) 0.0166(3) Uani 1 1 d . . . C3 C 0.5000 0.40606(10) 0.7500 0.0162(4) Uani 1 2 d S . . C4 C 0.44994(8) 0.46116(8) 0.62343(14) 0.0198(3) Uani 1 1 d . . . H4A H 0.4865(8) 0.5006(9) 0.6025(15) 0.019(4) Uiso 1 1 d . . . H4B H 0.4152(9) 0.4928(9) 0.6572(16) 0.027(4) Uiso 1 1 d . . . C5 C 0.40086(9) 0.41340(10) 0.49046(15) 0.0269(3) Uani 1 1 d . . . H5A H 0.3746(10) 0.4510(11) 0.4110(19) 0.039(5) Uiso 1 1 d . . . H5B H 0.4377(10) 0.3782(11) 0.4586(17) 0.033(4) Uiso 1 1 d . . . H5C H 0.3624(10) 0.3803(11) 0.5061(17) 0.035(4) Uiso 1 1 d . . . C6 C 0.22545(8) 0.28283(8) 0.67341(14) 0.0229(3) Uani 1 1 d . . . H6A H 0.2652(9) 0.2972(9) 0.6340(16) 0.026(4) Uiso 1 1 d . . . C7 C 0.15412(9) 0.32095(9) 0.62559(16) 0.0284(3) Uani 1 1 d . . . H7A H 0.1429(9) 0.3605(11) 0.5511(18) 0.032(4) Uiso 1 1 d . . . C8 C 0.09587(8) 0.30184(9) 0.68389(16) 0.0286(3) Uani 1 1 d . . . H8A H 0.0472(10) 0.3320(11) 0.6512(18) 0.037(5) Uiso 1 1 d . . . C9 C 0.11027(7) 0.24391(9) 0.78713(14) 0.0238(3) Uani 1 1 d . . . H9A H 0.0697(10) 0.2292(10) 0.8296(17) 0.030(4) Uiso 1 1 d . . . C10 C 0.18370(7) 0.20118(8) 0.83925(13) 0.0176(3) Uani 1 1 d . . . C11 C 0.20055(7) 0.14046(8) 0.94326(13) 0.0183(3) Uani 1 1 d . . . H11A H 0.1618(9) 0.1261(9) 0.9835(16) 0.024(4) Uiso 1 1 d . . . C12 C 0.27292(7) 0.10015(8) 0.98891(13) 0.0168(3) Uani 1 1 d . . . C13 C 0.29324(8) 0.03568(8) 1.09227(14) 0.0217(3) Uani 1 1 d . . . H13A H 0.2531(9) 0.0209(10) 1.1316(16) 0.028(4) Uiso 1 1 d . . . C14 C 0.36478(8) -0.00142(8) 1.13314(14) 0.0235(3) Uani 1 1 d . . . H14A H 0.3773(8) -0.0464(10) 1.2008(16) 0.025(4) Uiso 1 1 d . . . C15 C 0.42137(8) 0.02508(8) 1.07577(13) 0.0208(3) Uani 1 1 d . . . H15A H 0.4749(9) -0.0021(9) 1.1079(16) 0.024(4) Uiso 1 1 d . . . C16 C 0.40484(7) 0.08695(8) 0.97811(13) 0.0169(3) Uani 1 1 d . . . H16A H 0.4435(8) 0.1072(9) 0.9401(15) 0.019(4) Uiso 1 1 d . . . C17 C 0.32958(7) 0.12611(8) 0.92946(12) 0.0151(3) Uani 1 1 d . . . C18 C 0.24314(7) 0.22181(8) 0.78261(13) 0.0166(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0246(7) 0.0142(6) 0.0319(7) 0.000 0.0168(6) 0.000 O2 0.0283(5) 0.0194(5) 0.0353(5) -0.0006(4) 0.0238(4) 0.0011(4) N1 0.0183(5) 0.0147(5) 0.0236(6) 0.0009(4) 0.0139(4) -0.0013(4) N2 0.0162(5) 0.0159(5) 0.0161(5) -0.0010(4) 0.0069(4) -0.0008(4) C1 0.0179(8) 0.0164(8) 0.0171(8) 0.000 0.0082(7) 0.000 C2 0.0191(6) 0.0156(6) 0.0183(6) 0.0004(5) 0.0107(5) 0.0001(5) C3 0.0193(8) 0.0140(8) 0.0204(9) 0.000 0.0133(7) 0.000 C4 0.0241(7) 0.0168(6) 0.0228(7) 0.0036(5) 0.0139(6) 0.0039(5) C5 0.0282(7) 0.0267(8) 0.0248(7) 0.0034(6) 0.0086(6) 0.0000(6) C6 0.0248(7) 0.0213(7) 0.0218(7) 0.0015(5) 0.0075(6) -0.0001(6) C7 0.0312(8) 0.0219(7) 0.0257(7) 0.0048(6) 0.0026(6) 0.0057(6) C8 0.0202(7) 0.0283(8) 0.0308(8) -0.0048(6) 0.0017(6) 0.0083(6) C9 0.0160(6) 0.0282(7) 0.0257(7) -0.0079(6) 0.0056(5) 0.0014(6) C10 0.0140(6) 0.0203(6) 0.0176(6) -0.0054(5) 0.0047(5) -0.0010(5) C11 0.0162(6) 0.0235(7) 0.0179(6) -0.0055(5) 0.0095(5) -0.0049(5) C12 0.0181(6) 0.0176(6) 0.0158(6) -0.0032(5) 0.0074(5) -0.0036(5) C13 0.0260(7) 0.0227(7) 0.0191(6) 0.0007(5) 0.0117(6) -0.0037(6) C14 0.0326(7) 0.0197(7) 0.0185(6) 0.0036(5) 0.0097(5) 0.0017(6) C15 0.0216(6) 0.0210(7) 0.0179(6) -0.0020(5) 0.0050(5) 0.0049(5) C16 0.0162(6) 0.0191(6) 0.0162(6) -0.0030(5) 0.0071(5) -0.0005(5) C17 0.0162(6) 0.0160(6) 0.0140(6) -0.0033(5) 0.0066(5) -0.0020(5) C18 0.0161(6) 0.0164(6) 0.0166(6) -0.0027(5) 0.0052(5) -0.0005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.214(2) . ? O2 C2 1.2170(14) . ? N1 C2 1.3743(16) . ? N1 C1 1.3813(14) . ? N1 H1A 0.901(17) . ? N2 C17 1.3483(16) . ? N2 C18 1.3535(16) . ? C1 N1 1.3814(14) 2_656 ? C2 C3 1.5183(15) . ? C3 C2 1.5184(15) 2_656 ? C3 C4 1.5509(17) 2_656 ? C3 C4 1.5509(17) . ? C4 C5 1.522(2) . ? C4 H4A 1.002(14) . ? C4 H4B 0.968(15) . ? C5 H5A 0.981(18) . ? C5 H5B 1.020(17) . ? C5 H5C 0.942(17) . ? C6 C7 1.361(2) . ? C6 C18 1.4263(18) . ? C6 H6A 0.974(15) . ? C7 C8 1.423(2) . ? C7 H7A 0.950(17) . ? C8 C9 1.354(2) . ? C8 H8A 0.961(18) . ? C9 C10 1.4279(18) . ? C9 H9A 1.009(16) . ? C10 C11 1.3883(18) . ? C10 C18 1.4371(17) . ? C11 C12 1.3931(18) . ? C11 H11A 0.964(15) . ? C12 C13 1.4262(18) . ? C12 C17 1.4342(17) . ? C13 C14 1.358(2) . ? C13 H13A 0.981(16) . ? C14 C15 1.4216(19) . ? C14 H14A 0.967(16) . ? C15 C16 1.3602(18) . ? C15 H15A 1.011(15) . ? C16 C17 1.4279(17) . ? C16 H16A 0.975(14) . ? 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 N1 C1 125.77(11) . . ? C2 N1 H1A 116.3(11) . . ? C1 N1 H1A 118.0(11) . . ? C17 N2 C18 118.38(10) . . ? O1 C1 N1 121.76(8) . . ? O1 C1 N1 121.76(8) . 2_656 ? N1 C1 N1 116.48(15) . 2_656 ? O2 C2 N1 120.30(11) . . ? O2 C2 C3 121.21(12) . . ? N1 C2 C3 118.45(11) . . ? C2 C3 C2 114.30(14) . 2_656 ? C2 C3 C4 108.99(7) . 2_656 ? C2 C3 C4 107.53(7) 2_656 2_656 ? C2 C3 C4 107.54(7) . . ? C2 C3 C4 108.99(7) 2_656 . ? C4 C3 C4 109.42(15) 2_656 . ? C5 C4 C3 113.98(12) . . ? C5 C4 H4A 111.4(8) . . ? C3 C4 H4A 107.7(8) . . ? C5 C4 H4B 109.2(9) . . ? C3 C4 H4B 106.5(9) . . ? H4A C4 H4B 107.7(12) . . ? C4 C5 H5A 110.6(10) . . ? C4 C5 H5B 108.6(9) . . ? H5A C5 H5B 106.0(13) . . ? C4 C5 H5C 112.3(10) . . ? H5A C5 H5C 108.7(14) . . ? H5B C5 H5C 110.4(14) . . ? C7 C6 C18 120.44(13) . . ? C7 C6 H6A 120.4(9) . . ? C18 C6 H6A 119.1(9) . . ? C6 C7 C8 121.13(14) . . ? C6 C7 H7A 119.2(10) . . ? C8 C7 H7A 119.6(9) . . ? C9 C8 C7 120.19(13) . . ? C9 C8 H8A 120.9(10) . . ? C7 C8 H8A 118.9(10) . . ? C8 C9 C10 120.82(13) . . ? C8 C9 H9A 121.5(9) . . ? C10 C9 H9A 117.7(9) . . ? C11 C10 C9 122.81(12) . . ? C11 C10 C18 118.24(11) . . ? C9 C10 C18 118.96(12) . . ? C10 C11 C12 120.31(11) . . ? C10 C11 H11A 119.6(9) . . ? C12 C11 H11A 120.1(9) . . ? C11 C12 C13 123.24(11) . . ? C11 C12 C17 117.73(11) . . ? C13 C12 C17 119.02(11) . . ? C14 C13 C12 120.78(12) . . ? C14 C13 H13A 123.1(9) . . ? C12 C13 H13A 116.1(9) . . ? C13 C14 C15 120.22(12) . . ? C13 C14 H14A 120.2(9) . . ? C15 C14 H14A 119.6(9) . . ? C16 C15 C14 120.99(12) . . ? C16 C15 H15A 119.2(8) . . ? C14 C15 H15A 119.8(8) . . ? C15 C16 C17 120.56(12) . . ? C15 C16 H16A 122.1(8) . . ? C17 C16 H16A 117.3(8) . . ? N2 C17 C16 118.62(10) . . ? N2 C17 C12 122.97(11) . . ? C16 C17 C12 118.41(11) . . ? N2 C18 C6 119.27(11) . . ? N2 C18 C10 122.29(11) . . ? C6 C18 C10 118.44(12) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.266 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.046 data_ph _database_code_CSD 186036 _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1:1 molecular complex of 5,5-diethylbarbituric acid and 1,10-phenanthroline' ; _chemical_name_common '1:1 molecular complex of 5,5-diethylbarbituric acid and 1,10-phenanthroline' _chemical_melting_point '434 K' _chemical_formula_sum 'C20 H20 N4 O3' _chemical_formula_weight 364.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.656(3) _cell_length_b 7.0140(14) _cell_length_c 20.665(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.31(3) _cell_angle_gamma 90.00 _cell_volume 1815.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100K _cell_measurement_reflns_used 1300 _exptl_crystal_description needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 100K _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KUMA CCD detector [KUMA-1]' _diffrn_measurement_method '/w scans' _diffrn_reflns_number 10474 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4096 _reflns_number_gt 3539 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KUMA-1' _computing_data_reduction 'KM4-RED [KUMA-2]' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTON (Spek, 1992)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0505P)^2^+0.5730P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.018(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4096 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0778 _refine_ls_R_factor_gt 0.0599 _refine_ls_wR_factor_ref 0.1241 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 1.197 _refine_ls_restrained_S_all 1.197 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.37522(9) 0.90763(18) 0.00995(6) 0.0201(3) Uani 1 1 d . . . O2 O 0.22939(10) 0.48650(18) -0.14276(6) 0.0213(3) Uani 1 1 d . . . O3 O 0.55548(10) 0.80115(18) -0.15956(6) 0.0220(3) Uani 1 1 d . . . N1 N 0.29798(12) 0.7062(2) -0.06872(7) 0.0165(3) Uani 1 1 d . . . H1A H 0.2396(19) 0.705(3) -0.0473(12) 0.036(6) Uiso 1 1 d . . . N2 N 0.46578(11) 0.8437(2) -0.07419(7) 0.0160(3) Uani 1 1 d . . . H2A H 0.5173(18) 0.920(3) -0.0554(11) 0.029(6) Uiso 1 1 d . . . N3 N 0.05139(12) 0.7923(2) -0.12208(7) 0.0212(3) Uani 1 1 d . . . N4 N 0.12903(11) 0.7218(2) 0.00733(7) 0.0171(3) Uani 1 1 d . . . C1 C 0.37847(13) 0.8238(2) -0.04164(8) 0.0149(3) Uani 1 1 d . . . C2 C 0.29867(13) 0.6027(2) -0.12527(8) 0.0150(3) Uani 1 1 d . . . C3 C 0.38660(13) 0.6417(2) -0.16658(8) 0.0139(3) Uani 1 1 d . . . C4 C 0.47676(13) 0.7670(2) -0.13400(8) 0.0150(3) Uani 1 1 d . . . C5 C 0.33411(15) 0.7459(3) -0.22935(9) 0.0213(4) Uani 1 1 d . . . H5A H 0.3877(17) 0.750(3) -0.2614(10) 0.024(5) Uiso 1 1 d . . . H5B H 0.2713(17) 0.667(3) -0.2482(10) 0.025(5) Uiso 1 1 d . . . C6 C 0.29625(18) 0.9469(3) -0.21738(12) 0.0320(5) Uani 1 1 d . . . H6A H 0.257(2) 1.001(4) -0.2597(13) 0.051(7) Uiso 1 1 d . . . H6B H 0.3558(19) 1.026(3) -0.2016(11) 0.033(6) Uiso 1 1 d . . . H6C H 0.2405(19) 0.946(3) -0.1860(11) 0.036(6) Uiso 1 1 d . . . C7 C 0.43503(15) 0.4511(2) -0.18472(9) 0.0196(4) Uani 1 1 d . . . H7A H 0.3743(16) 0.376(3) -0.2090(9) 0.018(5) Uiso 1 1 d . . . H7B H 0.4861(16) 0.483(3) -0.2149(10) 0.025(5) Uiso 1 1 d . . . C8 C 0.48838(17) 0.3404(3) -0.12585(11) 0.0279(4) Uani 1 1 d . . . H8A H 0.5221(19) 0.222(3) -0.1397(11) 0.038(6) Uiso 1 1 d . . . H8B H 0.4374(18) 0.306(3) -0.0942(11) 0.034(6) Uiso 1 1 d . . . H8C H 0.5476(19) 0.420(3) -0.1016(12) 0.040(6) Uiso 1 1 d . . . C9 C 0.01067(16) 0.8185(3) -0.18413(9) 0.0265(4) Uani 1 1 d . . . H9A H 0.0636(17) 0.823(3) -0.2160(11) 0.029(6) Uiso 1 1 d . . . C10 C -0.09817(16) 0.8419(3) -0.20745(10) 0.0261(4) Uani 1 1 d . . . H10A H -0.1231(17) 0.859(3) -0.2544(11) 0.027(5) Uiso 1 1 d . . . C11 C -0.16857(15) 0.8379(3) -0.16293(9) 0.0214(4) Uani 1 1 d . . . H11A H -0.2420(16) 0.853(3) -0.1751(9) 0.017(5) Uiso 1 1 d . . . C12 C -0.12982(13) 0.8095(2) -0.09625(9) 0.0170(4) Uani 1 1 d . . . C13 C -0.19990(14) 0.8046(2) -0.04761(9) 0.0200(4) Uani 1 1 d . . . H13A H -0.2744(17) 0.824(3) -0.0617(10) 0.024(5) Uiso 1 1 d . . . C14 C -0.16124(14) 0.7757(2) 0.01616(9) 0.0200(4) Uani 1 1 d . . . H14A H -0.2084(16) 0.770(3) 0.0494(10) 0.023(5) Uiso 1 1 d . . . C15 C -0.04939(13) 0.7466(2) 0.03653(8) 0.0159(4) Uani 1 1 d . . . C16 C -0.00729(15) 0.7118(2) 0.10253(9) 0.0197(4) Uani 1 1 d . . . H16A H -0.0584(17) 0.708(3) 0.1366(11) 0.029(6) Uiso 1 1 d . . . C17 C 0.10033(15) 0.6854(3) 0.11918(9) 0.0208(4) Uani 1 1 d . . . H17A H 0.1323(17) 0.657(3) 0.1657(11) 0.032(6) Uiso 1 1 d . . . C18 C 0.16544(14) 0.6917(3) 0.06983(9) 0.0198(4) Uani 1 1 d . . . H18A H 0.2452(17) 0.671(3) 0.0806(10) 0.024(5) Uiso 1 1 d . . . C19 C 0.02253(13) 0.7512(2) -0.00989(8) 0.0141(3) Uani 1 1 d . . . C20 C -0.01858(13) 0.7857(2) -0.07811(8) 0.0156(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0167(6) 0.0247(7) 0.0192(6) -0.0093(5) 0.0031(5) -0.0020(5) O2 0.0204(6) 0.0223(7) 0.0213(7) -0.0053(5) 0.0029(5) -0.0082(5) O3 0.0182(6) 0.0294(7) 0.0194(7) -0.0020(5) 0.0056(5) -0.0048(5) N1 0.0134(7) 0.0204(8) 0.0163(7) -0.0040(6) 0.0047(5) -0.0028(6) N2 0.0131(7) 0.0180(7) 0.0167(7) -0.0047(6) 0.0011(5) -0.0033(6) N3 0.0182(7) 0.0262(8) 0.0193(8) -0.0037(6) 0.0035(6) -0.0004(6) N4 0.0160(7) 0.0156(7) 0.0194(7) -0.0017(6) 0.0016(6) -0.0022(6) C1 0.0140(8) 0.0143(8) 0.0161(8) -0.0006(6) 0.0013(6) 0.0014(6) C2 0.0143(8) 0.0154(8) 0.0150(8) -0.0009(6) 0.0012(6) 0.0009(6) C3 0.0143(8) 0.0142(8) 0.0135(8) -0.0011(6) 0.0025(6) -0.0008(6) C4 0.0150(8) 0.0143(8) 0.0155(8) 0.0014(6) 0.0015(6) 0.0003(6) C5 0.0225(9) 0.0211(9) 0.0181(9) 0.0039(7) -0.0043(7) -0.0074(7) C6 0.0302(11) 0.0196(10) 0.0413(13) 0.0071(9) -0.0121(10) -0.0027(8) C7 0.0222(9) 0.0162(9) 0.0214(9) -0.0026(7) 0.0070(7) 0.0000(7) C8 0.0285(11) 0.0206(10) 0.0340(11) 0.0024(8) 0.0027(9) 0.0060(8) C9 0.0234(10) 0.0381(11) 0.0186(9) -0.0039(8) 0.0052(7) -0.0009(8) C10 0.0272(10) 0.0318(11) 0.0180(10) -0.0032(8) -0.0011(7) 0.0011(8) C11 0.0176(9) 0.0205(9) 0.0242(10) -0.0025(7) -0.0034(7) 0.0020(7) C12 0.0167(8) 0.0116(8) 0.0225(9) -0.0023(7) 0.0024(7) 0.0006(6) C13 0.0130(8) 0.0176(9) 0.0295(10) -0.0005(7) 0.0033(7) 0.0023(7) C14 0.0175(9) 0.0186(9) 0.0254(9) 0.0002(7) 0.0085(7) 0.0006(7) C15 0.0183(9) 0.0103(8) 0.0199(9) -0.0004(6) 0.0058(7) -0.0007(6) C16 0.0240(9) 0.0167(9) 0.0197(9) 0.0019(7) 0.0077(7) -0.0020(7) C17 0.0249(9) 0.0191(9) 0.0179(9) 0.0025(7) 0.0011(7) -0.0022(7) C18 0.0161(8) 0.0202(9) 0.0225(9) -0.0005(7) 0.0005(7) -0.0008(7) C19 0.0148(8) 0.0086(7) 0.0192(9) -0.0013(6) 0.0030(6) -0.0018(6) C20 0.0175(8) 0.0117(8) 0.0176(8) -0.0032(6) 0.0027(6) -0.0015(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.223(2) . ? O2 C2 1.213(2) . ? O3 C4 1.217(2) . ? N1 C1 1.367(2) . ? N1 C2 1.377(2) . ? N1 H1A 0.91(2) . ? N2 C4 1.373(2) . ? N2 C1 1.381(2) . ? N2 H2A 0.89(2) . ? N3 C9 1.324(2) . ? N3 C20 1.358(2) . ? N4 C18 1.324(2) . ? N4 C19 1.359(2) . ? C2 C3 1.522(2) . ? C3 C4 1.519(2) . ? C3 C7 1.539(2) . ? C3 C5 1.552(2) . ? C5 C6 1.521(3) . ? C5 H5A 1.01(2) . ? C5 H5B 1.00(2) . ? C6 H6A 1.01(3) . ? C6 H6B 0.95(2) . ? C6 H6C 1.02(2) . ? C7 C8 1.517(3) . ? C7 H7A 1.00(2) . ? C7 H7B 0.99(2) . ? C8 H8A 1.00(2) . ? C8 H8B 1.01(2) . ? C8 H8C 1.01(2) . ? C9 C10 1.402(3) . ? C9 H9A 1.01(2) . ? C10 C11 1.370(3) . ? C10 H10A 0.98(2) . ? C11 C12 1.409(3) . ? C11 H11A 0.93(2) . ? C12 C20 1.413(2) . ? C12 C13 1.434(2) . ? C13 C14 1.353(3) . ? C13 H13A 0.96(2) . ? C14 C15 1.432(2) . ? C14 H14A 0.97(2) . ? C15 C16 1.412(2) . ? C15 C19 1.415(2) . ? C16 C17 1.368(3) . ? C16 H16A 1.02(2) . ? C17 C18 1.402(3) . ? C17 H17A 1.01(2) . ? C18 H18A 1.01(2) . ? C19 C20 1.451(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 124.76(15) . . ? C1 N1 H1A 114.4(15) . . ? C2 N1 H1A 120.7(15) . . ? C4 N2 C1 126.23(15) . . ? C4 N2 H2A 117.7(14) . . ? C1 N2 H2A 115.9(14) . . ? C9 N3 C20 116.91(16) . . ? C18 N4 C19 118.15(15) . . ? O1 C1 N1 122.01(15) . . ? O1 C1 N2 120.41(15) . . ? N1 C1 N2 117.58(15) . . ? O2 C2 N1 120.93(15) . . ? O2 C2 C3 120.60(15) . . ? N1 C2 C3 118.45(14) . . ? C4 C3 C2 114.75(14) . . ? C4 C3 C7 108.10(14) . . ? C2 C3 C7 109.26(14) . . ? C4 C3 C5 107.53(13) . . ? C2 C3 C5 107.09(14) . . ? C7 C3 C5 110.06(14) . . ? O3 C4 N2 120.61(16) . . ? O3 C4 C3 122.09(15) . . ? N2 C4 C3 117.29(14) . . ? C6 C5 C3 114.06(16) . . ? C6 C5 H5A 109.8(12) . . ? C3 C5 H5A 108.1(12) . . ? C6 C5 H5B 109.0(12) . . ? C3 C5 H5B 106.6(12) . . ? H5A C5 H5B 109.2(17) . . ? C5 C6 H6A 109.2(15) . . ? C5 C6 H6B 110.1(13) . . ? H6A C6 H6B 109.9(19) . . ? C5 C6 H6C 110.9(13) . . ? H6A C6 H6C 104.8(19) . . ? H6B C6 H6C 111.8(19) . . ? C8 C7 C3 113.32(15) . . ? C8 C7 H7A 110.6(11) . . ? C3 C7 H7A 106.0(11) . . ? C8 C7 H7B 111.5(12) . . ? C3 C7 H7B 106.0(12) . . ? H7A C7 H7B 109.2(16) . . ? C7 C8 H8A 110.9(14) . . ? C7 C8 H8B 112.9(13) . . ? H8A C8 H8B 109.0(19) . . ? C7 C8 H8C 109.3(14) . . ? H8A C8 H8C 106.6(19) . . ? H8B C8 H8C 107.9(18) . . ? N3 C9 C10 125.09(18) . . ? N3 C9 H9A 115.8(12) . . ? C10 C9 H9A 119.1(12) . . ? C11 C10 C9 117.96(17) . . ? C11 C10 H10A 121.2(12) . . ? C9 C10 H10A 120.9(12) . . ? C10 C11 C12 119.43(16) . . ? C10 C11 H11A 122.4(12) . . ? C12 C11 H11A 118.2(12) . . ? C11 C12 C20 117.96(16) . . ? C11 C12 C13 121.73(16) . . ? C20 C12 C13 120.31(16) . . ? C14 C13 C12 120.87(16) . . ? C14 C13 H13A 121.3(12) . . ? C12 C13 H13A 117.8(12) . . ? C13 C14 C15 120.70(17) . . ? C13 C14 H14A 121.4(12) . . ? C15 C14 H14A 117.9(12) . . ? C16 C15 C19 117.96(15) . . ? C16 C15 C14 121.83(16) . . ? C19 C15 C14 120.20(16) . . ? C17 C16 C15 119.29(17) . . ? C17 C16 H16A 122.0(12) . . ? C15 C16 H16A 118.8(12) . . ? C16 C17 C18 118.77(17) . . ? C16 C17 H17A 121.0(13) . . ? C18 C17 H17A 120.2(13) . . ? N4 C18 C17 123.81(16) . . ? N4 C18 H18A 115.6(12) . . ? C17 C18 H18A 120.5(12) . . ? N4 C19 C15 121.99(15) . . ? N4 C19 C20 118.85(15) . . ? C15 C19 C20 119.15(15) . . ? N3 C20 C12 122.64(16) . . ? N3 C20 C19 118.61(15) . . ? C12 C20 C19 118.75(16) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.323 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.049 data_uro _database_code_CSD 186037 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1:1 molecular complex of 5,5-diethylbarbituric acid and 1,3,5,7- hexamethylenetetramine ; _chemical_name_common ; 1:1 molecular complex of 5,5-diethylbarbituric acid and 1,3,5,7- hexamethylenetetramine ; _chemical_melting_point '443 K' _chemical_formula_sum 'C14 H24 N6 O3' _chemical_formula_weight 324.39 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.866(2) _cell_length_b 13.263(3) _cell_length_c 22.634(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3262.0(11) _cell_formula_units_Z 8 _cell_measurement_temperature 100K _cell_measurement_reflns_used 1200 _exptl_crystal_description Cubic _exptl_crystal_colour 'Colorless' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 100K _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KUMA CCD detector [KUMA-1]' _diffrn_measurement_method '\w scans' _diffrn_reflns_number 19108 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3736 _reflns_number_gt 3127 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KUMA-1' _computing_data_reduction 'KM4-RED [KUMA-2]' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTON (Spek, 1992)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0471P)^2^+0.1173P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0037(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3736 _refine_ls_number_parameters 305 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0861 _refine_ls_R_factor_gt 0.0649 _refine_ls_wR_factor_ref 0.1194 _refine_ls_wR_factor_gt 0.1120 _refine_ls_goodness_of_fit_ref 1.257 _refine_ls_restrained_S_all 1.257 _refine_ls_shift/su_max 0.003 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.51702(12) 0.04518(10) 0.71135(5) 0.0226(3) Uani 1 1 d . . . O2 O 0.35437(12) 0.15929(10) 0.54040(5) 0.0243(3) Uani 1 1 d . . . O3 O 0.16928(12) -0.10690(10) 0.64920(5) 0.0249(3) Uani 1 1 d . . . N1 N 0.43599(14) 0.09905(12) 0.62468(6) 0.0180(3) Uani 1 1 d . . . H1A H 0.502(2) 0.1473(16) 0.6218(9) 0.033(6) Uiso 1 1 d . . . N2 N 0.34344(13) -0.03107(11) 0.67857(7) 0.0177(3) Uani 1 1 d . . . H2A H 0.345(2) -0.0704(18) 0.7113(11) 0.044(7) Uiso 1 1 d . . . N3 N 0.84074(14) 0.30317(14) 0.64821(7) 0.0283(4) Uani 1 1 d . . . N4 N 0.62905(14) 0.24740(11) 0.63191(6) 0.0201(4) Uani 1 1 d . . . N5 N 0.68695(15) 0.42167(12) 0.61104(6) 0.0233(4) Uani 1 1 d . . . N6 N 0.67687(14) 0.36227(11) 0.71341(6) 0.0172(3) Uani 1 1 d . . . C1 C 0.43663(16) 0.03849(13) 0.67400(7) 0.0170(4) Uani 1 1 d . . . C2 C 0.34679(16) 0.10015(13) 0.58134(7) 0.0176(4) Uani 1 1 d . . . C3 C 0.24029(16) 0.02642(13) 0.58678(7) 0.0180(4) Uani 1 1 d . . . C4 C 0.24712(16) -0.04285(14) 0.64014(7) 0.0173(4) Uani 1 1 d . . . C5 C 0.23866(19) -0.04100(16) 0.53103(8) 0.0250(4) Uani 1 1 d . . . H5A H 0.1653(19) -0.0868(16) 0.5356(9) 0.027(5) Uiso 1 1 d . . . H5B H 0.2244(19) 0.0053(16) 0.4963(9) 0.033(6) Uiso 1 1 d . . . C6 C 0.3555(2) -0.10294(17) 0.52350(10) 0.0317(5) Uani 1 1 d . . . H6A H 0.352(2) -0.1424(19) 0.4876(12) 0.061(8) Uiso 1 1 d . . . H6B H 0.367(2) -0.1487(18) 0.5548(11) 0.047(7) Uiso 1 1 d . . . H6C H 0.434(2) -0.0585(17) 0.5214(9) 0.041(6) Uiso 1 1 d . . . C7 C 0.12121(17) 0.08928(17) 0.59164(9) 0.0255(4) Uani 1 1 d . . . H7A H 0.116(2) 0.1318(16) 0.5558(10) 0.041(6) Uiso 1 1 d . . . H7B H 0.0491(18) 0.0431(14) 0.5921(8) 0.021(5) Uiso 1 1 d . . . C8 C 0.1157(2) 0.15488(18) 0.64701(10) 0.0319(5) Uani 1 1 d . . . H8A H 0.038(2) 0.1978(17) 0.6476(9) 0.038(6) Uiso 1 1 d . . . H8B H 0.191(2) 0.2021(17) 0.6502(9) 0.038(6) Uiso 1 1 d . . . H8C H 0.115(2) 0.1108(17) 0.6836(10) 0.037(6) Uiso 1 1 d . . . C9 C 0.7607(2) 0.22051(16) 0.62980(10) 0.0288(5) Uani 1 1 d . . . H9A H 0.774(2) 0.1653(17) 0.6555(9) 0.034(6) Uiso 1 1 d . . . H9B H 0.7822(19) 0.2008(15) 0.5884(10) 0.034(6) Uiso 1 1 d . . . C10 C 0.61048(17) 0.33612(14) 0.59328(8) 0.0192(4) Uani 1 1 d . . . H10A H 0.6323(17) 0.3190(14) 0.5513(8) 0.021(5) Uiso 1 1 d . . . H10B H 0.5216(18) 0.3549(14) 0.5957(8) 0.020(5) Uiso 1 1 d . . . C11 C 0.8161(2) 0.38993(18) 0.60926(9) 0.0314(5) Uani 1 1 d . . . H11A H 0.871(2) 0.4501(18) 0.6218(9) 0.040(6) Uiso 1 1 d . . . H11B H 0.8387(19) 0.3686(15) 0.5708(10) 0.031(6) Uiso 1 1 d . . . C12 C 0.6570(2) 0.44741(15) 0.67242(8) 0.0262(5) Uani 1 1 d . . . H12A H 0.571(2) 0.4685(15) 0.6745(9) 0.030(6) Uiso 1 1 d . . . H12B H 0.7131(19) 0.5040(17) 0.6855(9) 0.029(5) Uiso 1 1 d . . . C13 C 0.80704(17) 0.33150(16) 0.70885(8) 0.0227(4) Uani 1 1 d . . . H13A H 0.8594(19) 0.3903(15) 0.7224(9) 0.026(5) Uiso 1 1 d . . . H13B H 0.8211(17) 0.2724(14) 0.7339(8) 0.018(5) Uiso 1 1 d . . . C14 C 0.59968(19) 0.27798(15) 0.69322(8) 0.0216(4) Uani 1 1 d . . . H14A H 0.5167(19) 0.2995(15) 0.6933(8) 0.024(5) Uiso 1 1 d . . . H14B H 0.6138(19) 0.2201(16) 0.7204(9) 0.031(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 0.0222(7) 0.0249(7) 0.0208(7) 0.0001(5) -0.0068(5) -0.0040(6) O2 0.0297(7) 0.0262(7) 0.0171(6) 0.0061(6) 0.0001(5) -0.0042(6) O3 0.0223(7) 0.0301(8) 0.0223(7) 0.0059(6) -0.0026(6) -0.0097(6) N1 0.0192(8) 0.0198(8) 0.0149(7) 0.0012(6) -0.0009(6) -0.0053(7) N2 0.0189(8) 0.0200(8) 0.0142(7) 0.0038(6) -0.0021(6) -0.0029(6) N3 0.0193(8) 0.0453(11) 0.0203(8) -0.0067(8) -0.0019(7) 0.0052(8) N4 0.0253(9) 0.0189(8) 0.0162(7) 0.0001(6) -0.0021(6) -0.0030(7) N5 0.0340(10) 0.0207(8) 0.0153(8) 0.0015(6) -0.0017(7) -0.0035(7) N6 0.0204(8) 0.0162(8) 0.0150(7) 0.0001(6) -0.0022(6) 0.0008(6) C1 0.0182(9) 0.0166(9) 0.0164(8) -0.0016(7) 0.0011(7) 0.0010(7) C2 0.0198(9) 0.0191(9) 0.0138(8) -0.0012(7) 0.0031(7) 0.0003(7) C3 0.0175(9) 0.0230(10) 0.0135(8) 0.0022(7) -0.0023(7) -0.0034(7) C4 0.0147(9) 0.0217(9) 0.0154(8) -0.0009(7) 0.0011(7) -0.0005(7) C5 0.0284(11) 0.0310(11) 0.0156(9) 0.0008(9) -0.0022(8) -0.0103(9) C6 0.0396(13) 0.0292(12) 0.0264(11) -0.0084(10) 0.0045(10) -0.0067(10) C7 0.0179(10) 0.0328(11) 0.0257(10) 0.0108(9) -0.0022(8) 0.0014(9) C8 0.0280(12) 0.0327(12) 0.0351(12) 0.0025(10) 0.0071(9) 0.0104(10) C9 0.0361(12) 0.0271(11) 0.0230(10) -0.0040(9) -0.0040(9) 0.0134(9) C10 0.0196(10) 0.0239(10) 0.0142(9) 0.0011(7) -0.0025(7) 0.0014(8) C11 0.0291(12) 0.0478(14) 0.0174(10) 0.0000(9) 0.0027(9) -0.0162(10) C12 0.0429(13) 0.0178(10) 0.0180(9) 0.0011(8) -0.0044(9) 0.0047(9) C13 0.0205(10) 0.0307(11) 0.0169(9) 0.0000(8) -0.0032(8) 0.0002(9) C14 0.0219(10) 0.0275(11) 0.0153(9) 0.0009(8) -0.0012(8) -0.0063(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.219(2) . ? O2 C2 1.217(2) . ? O3 C4 1.216(2) . ? N1 C1 1.375(2) . ? N1 C2 1.379(2) . ? N1 H1A 0.97(2) . ? N2 C4 1.370(2) . ? N2 C1 1.374(2) . ? N2 H2A 0.91(2) . ? N3 C9 1.460(3) . ? N3 C13 1.469(2) . ? N3 C11 1.474(3) . ? N4 C9 1.475(3) . ? N4 C10 1.480(2) . ? N4 C14 1.481(2) . ? N5 C10 1.463(2) . ? N5 C11 1.465(3) . ? N5 C12 1.467(2) . ? N6 C14 1.470(2) . ? N6 C13 1.476(2) . ? N6 C12 1.477(2) . ? C2 C3 1.520(2) . ? C3 C4 1.519(2) . ? C3 C7 1.543(3) . ? C3 C5 1.547(2) . ? C5 C6 1.521(3) . ? C5 H5A 1.01(2) . ? C5 H5B 1.01(2) . ? C6 H6A 0.97(3) . ? C6 H6B 0.94(2) . ? C6 H6C 1.03(2) . ? C7 C8 1.527(3) . ? C7 H7A 0.99(2) . ? C7 H7B 0.994(19) . ? C8 H8A 1.02(2) . ? C8 H8B 1.03(2) . ? C8 H8C 1.01(2) . ? C9 H9A 0.95(2) . ? C9 H9B 1.00(2) . ? C10 H10A 1.005(19) . ? C10 H10B 1.00(2) . ? C11 H11A 1.04(2) . ? C11 H11B 0.95(2) . ? C12 H12A 0.98(2) . ? C12 H12B 1.01(2) . ? C13 H13A 1.01(2) . ? C13 H13B 0.979(19) . ? C14 H14A 0.95(2) . ? C14 H14B 1.00(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 125.96(16) . . ? C1 N1 H1A 115.9(12) . . ? C2 N1 H1A 118.1(12) . . ? C4 N2 C1 126.30(16) . . ? C4 N2 H2A 117.7(15) . . ? C1 N2 H2A 115.9(15) . . ? C9 N3 C13 108.07(16) . . ? C9 N3 C11 107.87(15) . . ? C13 N3 C11 108.28(16) . . ? C9 N4 C10 107.77(15) . . ? C9 N4 C14 107.80(15) . . ? C10 N4 C14 107.86(15) . . ? C10 N5 C11 108.27(16) . . ? C10 N5 C12 108.34(15) . . ? C11 N5 C12 107.80(15) . . ? C14 N6 C13 108.34(15) . . ? C14 N6 C12 107.60(14) . . ? C13 N6 C12 107.93(15) . . ? O1 C1 N2 121.67(16) . . ? O1 C1 N1 121.61(16) . . ? N2 C1 N1 116.71(15) . . ? O2 C2 N1 120.06(16) . . ? O2 C2 C3 121.86(16) . . ? N1 C2 C3 118.08(15) . . ? C4 C3 C2 114.59(14) . . ? C4 C3 C7 108.12(15) . . ? C2 C3 C7 107.25(15) . . ? C4 C3 C5 107.43(15) . . ? C2 C3 C5 108.33(14) . . ? C7 C3 C5 111.16(15) . . ? O3 C4 N2 120.27(16) . . ? O3 C4 C3 121.49(16) . . ? N2 C4 C3 118.24(15) . . ? C6 C5 C3 113.21(16) . . ? C6 C5 H5A 110.2(11) . . ? C3 C5 H5A 105.9(12) . . ? C6 C5 H5B 111.7(12) . . ? C3 C5 H5B 106.6(12) . . ? H5A C5 H5B 109.0(16) . . ? C5 C6 H6A 110.7(15) . . ? C5 C6 H6B 111.9(15) . . ? H6A C6 H6B 106.8(19) . . ? C5 C6 H6C 112.4(12) . . ? H6A C6 H6C 107.6(19) . . ? H6B C6 H6C 107.1(19) . . ? C8 C7 C3 113.52(16) . . ? C8 C7 H7A 110.3(12) . . ? C3 C7 H7A 107.5(13) . . ? C8 C7 H7B 108.2(11) . . ? C3 C7 H7B 109.2(11) . . ? H7A C7 H7B 108.1(17) . . ? C7 C8 H8A 111.2(12) . . ? C7 C8 H8B 112.0(12) . . ? H8A C8 H8B 108.3(17) . . ? C7 C8 H8C 110.0(13) . . ? H8A C8 H8C 107.5(17) . . ? H8B C8 H8C 107.7(17) . . ? N3 C9 N4 112.77(16) . . ? N3 C9 H9A 108.2(14) . . ? N4 C9 H9A 108.6(14) . . ? N3 C9 H9B 109.0(12) . . ? N4 C9 H9B 108.7(12) . . ? H9A C9 H9B 109.6(17) . . ? N5 C10 N4 112.14(14) . . ? N5 C10 H10A 107.5(11) . . ? N4 C10 H10A 110.3(11) . . ? N5 C10 H10B 109.9(11) . . ? N4 C10 H10B 107.3(11) . . ? H10A C10 H10B 109.7(15) . . ? N5 C11 N3 112.45(16) . . ? N5 C11 H11A 108.9(13) . . ? N3 C11 H11A 109.4(12) . . ? N5 C11 H11B 111.0(13) . . ? N3 C11 H11B 105.7(12) . . ? H11A C11 H11B 109.3(17) . . ? N5 C12 N6 112.60(15) . . ? N5 C12 H12A 108.9(12) . . ? N6 C12 H12A 109.2(12) . . ? N5 C12 H12B 108.5(11) . . ? N6 C12 H12B 107.1(12) . . ? H12A C12 H12B 110.6(17) . . ? N3 C13 N6 112.01(14) . . ? N3 C13 H13A 109.8(11) . . ? N6 C13 H13A 107.7(11) . . ? N3 C13 H13B 107.3(11) . . ? N6 C13 H13B 109.3(11) . . ? H13A C13 H13B 110.7(15) . . ? N6 C14 N4 112.11(15) . . ? N6 C14 H14A 108.3(12) . . ? N4 C14 H14A 106.9(12) . . ? N6 C14 H14B 107.9(12) . . ? N4 C14 H14B 109.5(12) . . ? H14A C14 H14B 112.2(17) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.225 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.041