# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Fabrizia Grepioni' 'Dario Braga' 'Marcella Cadoni' 'Lucia Maini' 'van de Streek, Jacco' _publ_contact_author_name 'Fabrizia Grepioni' _publ_contact_author_address ; Dipartimento di Chimica G. Ciamician University of Bologna Via Selmi 2 Bologna 40126 ITALY ; _publ_contact_author_email FABRIZIA.GREPIONI@UNIBO.IT _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Solid-gas reactions between 1,3-dimethylbarbituric acid and amines. A structural and spectroscopic study ; data_1 _database_code_depnum_ccdc_archive 'CCDC 654148' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H11 N3 O3' _chemical_formula_weight 173.18 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 Trigonal _symmetry_space_group_name_H-M P3c1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-y, -x, z+1/2' '-x+y, -x, z' 'x, x-y, z+1/2' '-x+y, y, z+1/2' _cell_length_a 8.250(1) _cell_length_b 8.250(1) _cell_length_c 7.150(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 421.5(1) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 184 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type Psi-scan _exptl_absorpt_correction_T_min 0.891 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1432 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 5.70 _diffrn_reflns_theta_max 24.96 _reflns_number_total 272 _reflns_number_gt 210 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0650P)^2^+0.0153P] 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 0.041(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(4) _refine_ls_number_reflns 272 _refine_ls_number_parameters 48 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N2 N 0.3333 -0.3333 -0.2517(11) 0.084(2) Uani 1 3 d SD . . H100 H 0.3333 -0.3333 -0.13(3) 2(10) Uiso 1 3 d SD . . H200 H 0.397(6) -0.219(5) -0.274(9) 0.089(14) Uiso 1 1 d . . . N1 N 0.4819(5) 0.2772(4) -0.0036(5) 0.0510(11) Uani 0.67 1 d P . 1 C2 C 0.2860(7) 0.2156(10) -0.0038(15) 0.0732(19) Uani 0.67 1 d P A 1 H2A H 0.2468 0.2232 0.1207 0.110 Uiso 0.67 1 calc PR A 1 H2B H 0.2174 0.0884 -0.0466 0.110 Uiso 0.67 1 calc PR A 1 H2C H 0.2625 0.2938 -0.0857 0.110 Uiso 0.67 1 calc PR A 1 C3 C 0.4819(5) 0.2772(4) -0.0036(5) 0.0510(11) Uani 0.33 1 d P . 2 H3 H 0.3549 0.2385 -0.0041 0.061 Uiso 0.33 1 calc PR . 2 C1 C 0.5339(6) 0.1420(5) -0.0032(4) 0.0481(10) Uani 1 1 d . . . O1 O 0.4140(4) -0.0285(4) -0.0033(8) 0.0711(10) 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 N2 0.092(3) 0.092(3) 0.067(4) 0.000 0.000 0.0461(17) N1 0.0445(18) 0.052(2) 0.055(2) 0.0049(19) 0.0002(18) 0.0236(14) C2 0.050(3) 0.067(3) 0.107(5) -0.001(5) -0.003(5) 0.032(3) C3 0.0445(18) 0.052(2) 0.055(2) 0.0049(19) 0.0002(18) 0.0236(14) C1 0.048(2) 0.041(2) 0.051(3) 0.001(2) -0.003(2) 0.0181(17) O1 0.0638(19) 0.0430(15) 0.098(2) 0.0007(17) -0.001(2) 0.0203(15) _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 N2 H100 0.9(2) . ? N2 H200 0.84(4) . ? N1 C1 1.375(5) 4_665 ? N1 C1 1.381(5) . ? N1 C2 1.431(7) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C1 O1 1.251(6) . ? C1 C3 1.375(5) 2_655 ? C1 N1 1.375(5) 2_655 ? 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 H100 N2 H200 101(5) . . ? C1 N1 C1 123.4(5) 4_665 . ? C1 N1 C2 118.9(5) 4_665 . ? C1 N1 C2 117.7(4) . . ? O1 C1 C3 122.2(3) . 2_655 ? O1 C1 N1 122.2(3) . 2_655 ? C3 C1 N1 0.0(4) 2_655 2_655 ? O1 C1 N1 121.2(4) . . ? C3 C1 N1 116.6(5) 2_655 . ? N1 C1 N1 116.6(5) 2_655 . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.108 _refine_diff_density_min -0.104 _refine_diff_density_rms 0.032 # Attachment '2-revised.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 654149' _chemical_name_systematic '1,3-dimethylbarbiturate methylammonium' _chemical_name_common ? _chemical_formula_moiety 'C6 H7 N2 O3 1-, C H6 N 1+' _chemical_formula_sum 'C7 H13 N3 O3' _chemical_formula_structural '(C6 H7 N2 O3) (C N H6)' _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_weight 187.2 _chemical_melting_point ? _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' _space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y+1/2,-z _cell_length_a 8.42266(14) _cell_length_b 6.972150(61) _cell_length_c 8.06305(13) _cell_angle_alpha 90 _cell_angle_beta 98.6845(14) _cell_angle_gamma 90 _cell_volume 468.066(12) _cell_formula_units_Z 2 _cell_measurement_temperature 298 _cell_special_details ;? ; _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 200 _exptl_absorpt_coefficient_mu 0.884 _exptl_special_details ;? ; _diffrn_ambient_temperature 298 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54060 _diffrn_radiation_monochromator ? _diffrn_measurement_device_type "Panalytical X\'Pert PRO" _diffrn_measurement_method \q/2\q _refine_special_details ; ? ; _refine_ls_structure_factor_coef Inet _refine_ls_matrix_type fullcycle _refine_ls_R_factor_all ? _refine_ls_goodness_of_fit_all 1.23 _refine_ls_restrained_S_all ? _refine_ls_restrained_S_obs ? _refine_ls_number_parameters 78 _refine_ls_number_restraints 67 _refine_ls_number_constraints 0 _refine_ls_hydrogen_treatment refall _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ? _refine_ls_shift/su_max 0.00 _refine_ls_shift/su_mean ? _refine_ls_extinction_method ? _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'local program' _computing_cell_refinement 'TOPAS (Coelho, 2006)' _computing_data_reduction ? _computing_structure_solution 'DASH (David et al., 2006)' _computing_structure_refinement TOPAS loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv C1 C 0 0.71070(37) 0.93862(44) 0.45475(38) 1 3.409(67) O2 O 0 0.63981(47) 0.91515(45) 0.30959(44) 1 3.409(67) N3 N 0 0.63064(36) 0.92602(30) 0.59095(37) 1 3.409(67) N4 N 0 0.87182(35) 0.97880(31) 0.48482(37) 1 3.409(67) C5 C 0 0.70405(37) 0.95153(36) 0.75562(39) 1 3.409(67) C6 C 0 0.45885(36) 0.88477(38) 0.55611(41) 1 3.409(67) C7 C 0 0.95824(37) 1.00642(39) 0.64469(39) 1 3.409(67) C8 C 0 0.95265(37) 0.99224(37) 0.33704(38) 1 3.409(67) C9 C 0 0.86890(37) 0.99155(35) 0.77783(39) 1 3.409(67) O10 O 0 0.62000(44) 0.93762(49) 0.86992(45) 1 3.409(67) H11 H 0 0.3901(14) 1.0112(22) 0.5739(14) 1 4.090632 H12 H 0 0.4288(17) 0.8385(20) 0.4265(18) 1 4.090632 H13 H 0 0.4370(14) 0.7768(17) 0.6461(15) 1 4.090632 O14 O 0 1.10586(46) 1.03919(47) 0.65852(48) 1 3.409(67) H15 H 0 0.9877(15) 0.8515(17) 0.2967(14) 1 4.090632 H16 H 0 0.8730(16) 1.0621(22) 0.2363(13) 1 4.090632 H17 H 0 1.0560(15) 1.0777(22) 0.3745(13) 1 4.090632 H18 H 0 0.9306(14) 1.0125(22) 0.9016(13) 1 4.090632 C19 C 0 0.28847(38) -0.03737(47) 0.05134(37) 1 3.409(67) H20 H 0 0.2508(14) -0.1651(17) -0.0209(17) 1 4.090632 H21 H 0 0.1918(13) 0.0201(21) 0.1082(13) 1 4.090632 H22 H 0 0.3911(13) -0.0672(23) 0.1446(13) 1 4.090632 N23 N 0 0.33435(35) 0.11436(41) -0.06382(36) 1 3.409(67) H24 H 0 0.2407(16) 0.1487(17) -0.1521(15) 1 4.090632 H25 H 0 0.3695(17) 0.2349(19) 0.0008(21) 1 4.090632 H26 H 0 0.4261(17) 0.0741(21) -0.1223(14) 1 4.090632 # Attachment '2a-revised.cif' data_2a _database_code_depnum_ccdc_archive 'CCDC 654150' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H23 N5 O9' _chemical_formula_weight 393.36 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.500(2) _cell_length_b 10.560(3) _cell_length_c 11.412(2) _cell_angle_alpha 65.843(17) _cell_angle_beta 88.118(18) _cell_angle_gamma 71.467(19) _cell_volume 880.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3258 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0827 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 24.97 _reflns_number_total 3089 _reflns_number_gt 1540 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0821P)^2^+0.6263P] 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 3089 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1382 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1610 _refine_ls_wR_factor_gt 0.1170 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_restrained_S_all 0.918 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2600(4) 0.3442(4) 0.7251(3) 0.0253(8) Uani 1 1 d . . . C2 C 0.2849(4) 0.3595(4) 0.5993(3) 0.0291(8) Uani 1 1 d . . . O1 O 0.4000(3) 0.3981(3) 0.5383(2) 0.0436(7) Uani 1 1 d . . . N1 N 0.1738(4) 0.3275(3) 0.5366(3) 0.0328(8) Uani 1 1 d . . . C3 C 0.1923(5) 0.3457(5) 0.4024(4) 0.0487(11) Uani 1 1 d . . . H3A H 0.2609 0.2539 0.4024 0.073 Uiso 1 1 calc R . . H3B H 0.2438 0.4192 0.3603 0.073 Uiso 1 1 calc R . . H3C H 0.0843 0.3760 0.3571 0.073 Uiso 1 1 calc R . . C4 C 0.0507(5) 0.2749(4) 0.5951(4) 0.0361(9) Uani 1 1 d . . . O2 O -0.0398(4) 0.2425(3) 0.5384(3) 0.0524(8) Uani 1 1 d . . . N2 N 0.0352(4) 0.2556(3) 0.7211(3) 0.0321(7) Uani 1 1 d . . . C5 C -0.0969(5) 0.1999(5) 0.7839(4) 0.0503(12) Uani 1 1 d . . . H5A H -0.2034 0.2670 0.7371 0.075 Uiso 1 1 calc R . . H5B H -0.0942 0.1910 0.8710 0.075 Uiso 1 1 calc R . . H5C H -0.0796 0.1051 0.7847 0.075 Uiso 1 1 calc R . . C6 C 0.1390(4) 0.2874(4) 0.7905(3) 0.0285(8) Uani 1 1 d . . . O3 O 0.1218(3) 0.2614(3) 0.9070(2) 0.0400(7) Uani 1 1 d . . . C7 C 0.3745(4) 0.3709(4) 0.8032(3) 0.0271(8) Uani 1 1 d . . . O4 O 0.4768(3) 0.4518(3) 0.7271(2) 0.0339(6) Uani 1 1 d . . . H400 H 0.4715 0.4453 0.6588 0.090 Uiso 1 1 d . . . C8 C 0.2722(4) 0.4686(4) 0.8678(3) 0.0270(8) Uani 1 1 d . . . O5 O 0.1555(3) 0.5790(3) 0.8064(2) 0.0404(7) Uani 1 1 d . . . N3 N 0.3264(4) 0.4336(3) 0.9935(3) 0.0287(7) Uani 1 1 d . . . C9 C 0.2318(5) 0.5307(4) 1.0529(4) 0.0391(10) Uani 1 1 d . . . H9A H 0.2006 0.6314 0.9905 0.059 Uiso 1 1 calc R . . H9B H 0.2999 0.5170 1.1254 0.059 Uiso 1 1 calc R . . H9C H 0.1331 0.5070 1.0816 0.059 Uiso 1 1 calc R . . C10 C 0.4611(5) 0.3128(4) 1.0691(4) 0.0323(9) Uani 1 1 d . . . O6 O 0.5072(4) 0.2948(3) 1.1757(3) 0.0492(8) Uani 1 1 d . . . N4 N 0.5416(4) 0.2128(3) 1.0185(3) 0.0313(7) Uani 1 1 d . . . C11 C 0.6820(5) 0.0835(4) 1.1029(4) 0.0441(11) Uani 1 1 d . . . H11A H 0.7298 0.0230 1.0582 0.066 Uiso 1 1 calc R . . H11B H 0.6422 0.0276 1.1802 0.066 Uiso 1 1 calc R . . H11C H 0.7654 0.1158 1.1253 0.066 Uiso 1 1 calc R . . C12 C 0.4970(4) 0.2245(4) 0.8987(3) 0.0278(8) Uani 1 1 d . . . O7 O 0.5633(3) 0.1256(3) 0.8667(3) 0.0441(7) Uani 1 1 d . . . N5 N 0.3177(4) 0.7742(4) 0.5672(3) 0.0415(8) Uani 1 1 d . . . H500 H 0.3763 0.7852 0.5046 0.090 Uiso 1 1 d . . . H501 H 0.3942 0.6948 0.6508 0.090 Uiso 1 1 d . . . H503 H 0.2526 0.7343 0.5347 0.090 Uiso 1 1 d . . . C13 C 0.2252(7) 0.9111(5) 0.5807(5) 0.0689(15) Uani 1 1 d . . . H13A H 0.1512 0.8910 0.6461 0.103 Uiso 1 1 calc R . . H13B H 0.1616 0.9835 0.4999 0.103 Uiso 1 1 calc R . . H13C H 0.3029 0.9475 0.6050 0.103 Uiso 1 1 calc R . . O8 O 0.4225(5) 0.9573(4) 0.3388(3) 0.0753(11) Uani 1 1 d . . . H800 H 0.3021 1.0566 0.2911 0.090 Uiso 1 1 d . . . H801 H 0.4273 0.9224 0.2642 0.090 Uiso 1 1 d . . . O9 O 0.1278(5) 1.1783(4) 0.1790(3) 0.0882(13) Uani 1 1 d . . . H900 H 0.1451 1.1963 0.0987 0.090 Uiso 1 1 d . . . H901 H 0.0422 1.2578 0.1808 0.090 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 C1 0.0229(19) 0.033(2) 0.0244(18) -0.0154(16) 0.0022(15) -0.0101(16) C2 0.027(2) 0.035(2) 0.0282(19) -0.0152(17) 0.0045(17) -0.0115(17) O1 0.0452(17) 0.067(2) 0.0335(15) -0.0250(14) 0.0153(13) -0.0338(16) N1 0.0279(17) 0.047(2) 0.0274(17) -0.0176(15) -0.0004(14) -0.0136(15) C3 0.057(3) 0.067(3) 0.031(2) -0.027(2) 0.001(2) -0.024(2) C4 0.029(2) 0.038(2) 0.043(2) -0.022(2) -0.0023(19) -0.0067(19) O2 0.0455(18) 0.069(2) 0.061(2) -0.0368(17) -0.0013(15) -0.0288(16) N2 0.0244(17) 0.0394(18) 0.0383(18) -0.0182(15) 0.0072(14) -0.0159(14) C5 0.033(2) 0.066(3) 0.070(3) -0.036(3) 0.020(2) -0.029(2) C6 0.0219(19) 0.027(2) 0.036(2) -0.0162(17) 0.0038(16) -0.0027(16) O3 0.0404(17) 0.0532(18) 0.0325(15) -0.0225(14) 0.0148(12) -0.0182(14) C7 0.025(2) 0.032(2) 0.0278(19) -0.0152(17) 0.0050(16) -0.0109(17) O4 0.0320(15) 0.0444(16) 0.0333(14) -0.0189(12) 0.0079(12) -0.0200(13) C8 0.026(2) 0.033(2) 0.0254(18) -0.0153(17) 0.0033(16) -0.0099(18) O5 0.0389(16) 0.0375(16) 0.0367(15) -0.0187(13) -0.0061(13) 0.0029(13) N3 0.0279(17) 0.0332(17) 0.0254(16) -0.0164(14) 0.0014(13) -0.0053(14) C9 0.040(2) 0.043(2) 0.037(2) -0.0233(19) 0.0058(18) -0.0083(19) C10 0.030(2) 0.036(2) 0.032(2) -0.0143(18) 0.0033(18) -0.0130(18) O6 0.056(2) 0.0513(18) 0.0336(16) -0.0205(14) -0.0147(14) -0.0032(15) N4 0.0319(18) 0.0296(17) 0.0279(16) -0.0113(14) -0.0044(13) -0.0047(14) C11 0.041(2) 0.036(2) 0.042(2) -0.013(2) -0.009(2) 0.0014(19) C12 0.028(2) 0.031(2) 0.031(2) -0.0184(17) 0.0044(16) -0.0111(17) O7 0.0431(17) 0.0415(17) 0.0475(17) -0.0286(15) -0.0021(14) 0.0000(14) N5 0.038(2) 0.043(2) 0.042(2) -0.0170(17) -0.0038(16) -0.0130(16) C13 0.075(4) 0.062(3) 0.067(3) -0.031(3) -0.009(3) -0.013(3) O8 0.098(3) 0.074(2) 0.054(2) -0.0308(19) 0.0103(19) -0.024(2) O9 0.104(3) 0.080(3) 0.045(2) -0.0238(19) 0.0035(19) 0.012(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.396(5) . ? C1 C2 1.394(5) . ? C1 C7 1.503(5) . ? C2 O1 1.258(4) . ? C2 N1 1.401(5) . ? N1 C4 1.367(5) . ? N1 C3 1.473(5) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 O2 1.228(4) . ? C4 N2 1.376(5) . ? N2 C6 1.403(4) . ? N2 C5 1.463(5) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 O3 1.257(4) . ? C7 O4 1.433(4) . ? C7 C12 1.528(5) . ? C7 C8 1.541(5) . ? O4 H400 0.8136 . ? C8 O5 1.215(4) . ? C8 N3 1.381(4) . ? N3 C10 1.385(4) . ? N3 C9 1.473(4) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 O6 1.211(4) . ? C10 N4 1.389(5) . ? N4 C12 1.376(4) . ? N4 C11 1.477(5) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 O7 1.211(4) . ? N5 C13 1.478(5) . ? N5 H500 0.8471 . ? N5 H501 1.0373 . ? N5 H503 0.9537 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? O8 H800 1.1536 . ? O8 H801 1.0522 . ? O9 H900 0.8738 . ? O9 H901 0.9266 . ? 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 C6 C1 C2 121.7(3) . . ? C6 C1 C7 116.1(3) . . ? C2 C1 C7 121.8(3) . . ? O1 C2 N1 117.6(3) . . ? O1 C2 C1 125.3(3) . . ? N1 C2 C1 117.2(3) . . ? C4 N1 C2 123.3(3) . . ? C4 N1 C3 117.4(3) . . ? C2 N1 C3 119.2(3) . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O2 C4 N1 121.4(4) . . ? O2 C4 N2 121.2(4) . . ? N1 C4 N2 117.4(3) . . ? C4 N2 C6 123.0(3) . . ? C4 N2 C5 117.6(3) . . ? C6 N2 C5 119.3(3) . . ? N2 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O3 C6 C1 123.4(3) . . ? O3 C6 N2 119.5(3) . . ? C1 C6 N2 117.1(3) . . ? O4 C7 C1 113.6(3) . . ? O4 C7 C12 105.2(3) . . ? C1 C7 C12 110.1(3) . . ? O4 C7 C8 103.9(3) . . ? C1 C7 C8 110.3(3) . . ? C12 C7 C8 113.5(3) . . ? C7 O4 H400 103.9 . . ? O5 C8 N3 121.3(3) . . ? O5 C8 C7 120.6(3) . . ? N3 C8 C7 117.8(3) . . ? C8 N3 C10 125.2(3) . . ? C8 N3 C9 117.5(3) . . ? C10 N3 C9 117.3(3) . . ? N3 C9 H9A 109.5 . . ? N3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O6 C10 N4 121.1(4) . . ? O6 C10 N3 121.1(3) . . ? N4 C10 N3 117.8(3) . . ? C12 N4 C10 124.8(3) . . ? C12 N4 C11 118.9(3) . . ? C10 N4 C11 116.3(3) . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O7 C12 N4 120.6(3) . . ? O7 C12 C7 121.0(3) . . ? N4 C12 C7 118.1(3) . . ? C13 N5 H500 114.9 . . ? C13 N5 H501 112.1 . . ? H500 N5 H501 108.1 . . ? C13 N5 H503 116.1 . . ? H500 N5 H503 92.5 . . ? H501 N5 H503 111.5 . . ? N5 C13 H13A 109.5 . . ? N5 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N5 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? H800 O8 H801 94.1 . . ? H900 O9 H901 108.9 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.394 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.056 # Attachment '2b-revised.cif' data_2b _database_code_depnum_ccdc_archive 'CCDC 654151' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 N6 O6' _chemical_formula_weight 372.39 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 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 11.290(5) _cell_length_b 19.761(6) _cell_length_c 8.300(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.17 _cell_angle_gamma 90.00 _cell_volume 1844.2(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1747 _diffrn_reflns_av_R_equivalents 0.0535 _diffrn_reflns_av_sigmaI/netI 0.0657 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1626 _reflns_number_gt 807 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1348P)^2^+0.5265P] 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 0.008(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1626 _refine_ls_number_parameters 125 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1389 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.2106 _refine_ls_wR_factor_gt 0.1588 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 0.957 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H300 H 0.2556 0.2536 0.1970 0.050 Uiso 1 1 d . . . H301 H 0.3626 0.2854 0.1359 0.050 Uiso 1 1 d . . . H302 H 0.3762 0.2518 0.2758 0.050 Uiso 1 1 d . . . O2 O 0.1813(2) 0.17170(13) 0.1301(3) 0.0514(8) Uani 1 1 d . . . O3 O -0.0191(3) 0.26371(15) -0.0346(3) 0.0517(8) Uani 1 1 d . . . C4 C 0.0000 0.1801(3) 0.2500 0.0385(12) Uani 1 2 d S . . N2 N -0.0113(3) 0.36100(15) 0.1091(3) 0.0411(8) Uani 1 1 d . . . C5 C 0.0000 0.2547(3) 0.2500 0.0358(12) Uani 1 2 d S . . N1 N 0.0899(3) 0.07405(15) 0.1913(4) 0.0439(9) Uani 1 1 d . . . C3 C 0.0935(3) 0.14483(19) 0.1892(4) 0.0402(9) Uani 1 1 d . . . O1 O 0.0000 -0.0249(2) 0.2500 0.0627(12) Uani 1 2 d S . . N3 N 0.3265(3) 0.27974(17) 0.2121(4) 0.0462(9) Uani 1 1 d . . . C2 C 0.0000 0.0374(3) 0.2500 0.0448(13) Uani 1 2 d S . . C6 C -0.0108(3) 0.29123(18) 0.1032(4) 0.0379(9) Uani 1 1 d . . . C7 C 0.0000 0.3990(3) 0.2500 0.0442(14) Uani 1 2 d S . . O4 O 0.0000 0.4601(2) 0.2500 0.0778(15) Uani 1 2 d S . . C9 C -0.0274(6) 0.3998(2) -0.0434(5) 0.0761(16) Uani 1 1 d . . . H9A H -0.0455 0.3692 -0.1322 0.114 Uiso 1 1 calc R . . H9B H 0.0444 0.4239 -0.0590 0.114 Uiso 1 1 calc R . . H9C H -0.0916 0.4313 -0.0382 0.114 Uiso 1 1 calc R . . C8 C 0.1873(4) 0.0354(2) 0.1302(6) 0.0638(13) Uani 1 1 d . . . H8A H 0.2309 0.0123 0.2183 0.096 Uiso 1 1 calc R . . H8B H 0.2394 0.0657 0.0802 0.096 Uiso 1 1 calc R . . H8C H 0.1552 0.0030 0.0520 0.096 Uiso 1 1 calc R . . C10 C 0.2999(5) 0.3457(2) 0.2732(8) 0.0782(16) Uani 1 1 d . . . H10A H 0.2663 0.3410 0.3749 0.117 Uiso 1 1 calc R . . H10B H 0.2439 0.3682 0.1973 0.117 Uiso 1 1 calc R . . H10C H 0.3716 0.3719 0.2882 0.117 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 O2 0.0479(17) 0.0470(17) 0.0618(18) -0.0031(13) 0.0197(13) -0.0066(13) O3 0.066(2) 0.0624(19) 0.0271(14) -0.0105(12) 0.0030(12) 0.0004(15) C4 0.042(3) 0.038(3) 0.035(3) 0.000 0.004(2) 0.000 N2 0.061(2) 0.0373(18) 0.0255(16) 0.0050(13) 0.0075(14) 0.0003(15) C5 0.040(3) 0.038(3) 0.030(3) 0.000 0.007(2) 0.000 N1 0.0392(18) 0.0387(19) 0.055(2) -0.0029(15) 0.0097(15) 0.0038(14) C3 0.040(2) 0.040(2) 0.041(2) -0.0028(17) 0.0037(17) -0.0031(18) O1 0.057(3) 0.043(3) 0.090(3) 0.000 0.017(2) 0.000 N3 0.0412(19) 0.060(2) 0.0382(18) 0.0020(15) 0.0075(13) -0.0082(16) C2 0.042(3) 0.034(3) 0.059(3) 0.000 0.005(3) 0.000 C6 0.036(2) 0.046(2) 0.032(2) -0.0050(16) 0.0057(15) -0.0029(17) C7 0.061(4) 0.033(3) 0.040(3) 0.000 0.013(3) 0.000 O4 0.141(5) 0.042(3) 0.053(3) 0.000 0.021(3) 0.000 C9 0.130(5) 0.065(3) 0.033(3) 0.020(2) 0.010(3) 0.002(3) C8 0.058(3) 0.051(3) 0.086(3) -0.003(2) 0.027(2) 0.012(2) C10 0.065(3) 0.060(3) 0.111(4) -0.015(3) 0.011(3) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C3 1.262(4) . ? O3 C6 1.262(4) . ? C4 C3 1.396(4) 2 ? C4 C3 1.396(4) . ? C4 C5 1.475(7) . ? N2 C6 1.380(5) . ? N2 C7 1.387(4) . ? N2 C9 1.476(5) . ? C5 C6 1.412(4) . ? C5 C6 1.412(4) 2 ? N1 C2 1.372(4) . ? N1 C3 1.400(5) . ? N1 C8 1.465(5) . ? O1 C2 1.229(7) . ? N3 C10 1.440(6) . ? C2 N1 1.372(4) 2 ? C7 O4 1.207(7) . ? C7 N2 1.387(4) 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 C3 C4 C3 120.2(5) 2 . ? C3 C4 C5 119.9(2) 2 . ? C3 C4 C5 119.9(2) . . ? C6 N2 C7 124.8(3) . . ? C6 N2 C9 119.2(3) . . ? C7 N2 C9 115.9(3) . . ? C6 C5 C6 118.5(5) . 2 ? C6 C5 C4 120.8(2) . . ? C6 C5 C4 120.8(2) 2 . ? C2 N1 C3 123.7(3) . . ? C2 N1 C8 116.7(3) . . ? C3 N1 C8 119.5(3) . . ? O2 C3 C4 125.2(4) . . ? O2 C3 N1 116.7(3) . . ? C4 C3 N1 118.1(4) . . ? O1 C2 N1 121.9(2) . . ? O1 C2 N1 121.9(2) . 2 ? N1 C2 N1 116.2(5) . 2 ? O3 C6 N2 117.6(3) . . ? O3 C6 C5 123.7(4) . . ? N2 C6 C5 118.7(3) . . ? O4 C7 N2 122.8(2) . . ? O4 C7 N2 122.8(2) . 2 ? N2 C7 N2 114.4(4) . 2 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.280 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.066 # Attachment '3a-revised.cif' data_3a _database_code_depnum_ccdc_archive 'CCDC 654152' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H31 N7 O9' _chemical_formula_weight 513.52 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4950(10) _cell_length_b 12.416(2) _cell_length_c 12.697(2) _cell_angle_alpha 110.082(2) _cell_angle_beta 95.887(2) _cell_angle_gamma 95.181(2) _cell_volume 1239.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.742871 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10652 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 28.48 _reflns_number_total 5575 _reflns_number_gt 3883 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0886P)^2^+0.3800P] 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 5575 _refine_ls_number_parameters 341 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1453 _refine_ls_wR_factor_gt 0.1309 _refine_ls_goodness_of_fit_ref 0.834 _refine_ls_restrained_S_all 0.834 _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 H700 H 0.477(2) 0.4486(19) 0.6983(18) 0.071(6) Uiso 1 1 d . . . H701 H 0.316(3) 0.4934(17) 0.7213(17) 0.068(6) Uiso 1 1 d . . . C1 C 0.70612(18) 0.34620(13) 0.58279(14) 0.0461(4) Uani 1 1 d . . . C2 C 0.8819(2) 0.25239(14) 0.44805(13) 0.0484(4) Uani 1 1 d . . . C3 C 0.98688(18) 0.42648(13) 0.61305(14) 0.0459(4) Uani 1 1 d . . . C4 C 0.83466(18) 0.42844(13) 0.64398(14) 0.0475(4) Uani 1 1 d . . . H4 H 0.8183 0.4878 0.7088 0.057 Uiso 1 1 calc R . . C5 C 0.6084(2) 0.16389(17) 0.42257(18) 0.0665(5) Uani 1 1 d . . . H5A H 0.6014 0.1518 0.3433 0.100 Uiso 1 1 calc R . . H5B H 0.5089 0.1840 0.4482 0.100 Uiso 1 1 calc R . . H5C H 0.6308 0.0942 0.4346 0.100 Uiso 1 1 calc R . . C6 C 1.1602(2) 0.33299(19) 0.47333(18) 0.0670(5) Uani 1 1 d . . . H6A H 1.1535 0.2689 0.4034 0.100 Uiso 1 1 calc R . . H6B H 1.2379 0.3240 0.5291 0.100 Uiso 1 1 calc R . . H6C H 1.1915 0.4038 0.4615 0.100 Uiso 1 1 calc R . . N1 N 0.73640(16) 0.25771(11) 0.48593(11) 0.0484(3) Uani 1 1 d . . . N2 N 1.00456(15) 0.33653(12) 0.51284(11) 0.0476(3) Uani 1 1 d . . . O1 O 0.56631(14) 0.34225(11) 0.60523(12) 0.0639(3) Uani 1 1 d . . . O2 O 0.90186(17) 0.17541(12) 0.36134(11) 0.0697(4) Uani 1 1 d . . . O3 O 1.10744(14) 0.49670(11) 0.66644(11) 0.0638(3) Uani 1 1 d . . . C7 C 0.8818(3) -0.11895(19) 0.38363(19) 0.0755(6) Uani 1 1 d . . . H7A H 0.7734 -0.1535 0.3755 0.113 Uiso 1 1 calc R . . H7B H 0.8827 -0.0455 0.3740 0.113 Uiso 1 1 calc R . . H7C H 0.9352 -0.1079 0.4577 0.113 Uiso 1 1 calc R . . C8 C 0.8786(2) -0.28720(16) 0.21264(18) 0.0602(5) Uani 1 1 d . . . C9 C 0.9662(2) -0.35894(19) 0.12576(18) 0.0713(5) Uani 1 1 d . . . H9A H 0.9139 -0.3639 0.0523 0.086 Uiso 1 1 calc R . . H9B H 0.9538 -0.4365 0.1280 0.086 Uiso 1 1 calc R . . C10 C 1.1387(2) -0.32292(18) 0.13170(18) 0.0639(5) Uani 1 1 d . . . C11 C 1.3788(2) -0.1880(2) 0.2294(2) 0.0834(7) Uani 1 1 d . . . H11A H 1.4405 -0.2381 0.2544 0.125 Uiso 1 1 calc R . . H11B H 1.4049 -0.1102 0.2826 0.125 Uiso 1 1 calc R . . H11C H 1.4026 -0.1906 0.1563 0.125 Uiso 1 1 calc R . . C12 C 1.1265(2) -0.15993(16) 0.30354(16) 0.0566(4) Uani 1 1 d . . . N3 N 0.96452(17) -0.19526(12) 0.29743(13) 0.0540(4) Uani 1 1 d . . . N4 N 1.20797(17) -0.22670(13) 0.22143(14) 0.0575(4) Uani 1 1 d . . . O4 O 1.19296(19) -0.07375(14) 0.37825(14) 0.0822(4) Uani 1 1 d . . . O5 O 0.73625(18) -0.30969(14) 0.20880(18) 0.0973(6) Uani 1 1 d . . . O6 O 1.2153(2) -0.37516(17) 0.06082(16) 0.1018(6) Uani 1 1 d . . . C13 C 1.02967(18) 0.98457(13) 0.86865(12) 0.0426(3) Uani 1 1 d . . . C14 C 1.3090(2) 1.06321(17) 0.89544(18) 0.0655(5) Uani 1 1 d . . . H14A H 1.4095 1.0529 0.9303 0.098 Uiso 1 1 calc R . . H14B H 1.2774 1.1350 0.9410 0.098 Uiso 1 1 calc R . . H14C H 1.3196 1.0645 0.8213 0.098 Uiso 1 1 calc R . . C15 C 1.23557(18) 0.86290(14) 0.87943(14) 0.0495(4) Uani 1 1 d . . . C16 C 1.10915(19) 0.76672(15) 0.86747(15) 0.0525(4) Uani 1 1 d . . . H16A H 1.1234 0.7005 0.8027 0.063 Uiso 1 1 calc R . . H16B H 1.1273 0.7454 0.9339 0.063 Uiso 1 1 calc R . . C17 C 0.93987(19) 0.78686(14) 0.85325(14) 0.0487(4) Uani 1 1 d . . . C18 C 0.74716(19) 0.91186(18) 0.82108(17) 0.0615(5) Uani 1 1 d . . . H18A H 0.7335 0.9148 0.7462 0.092 Uiso 1 1 calc R . . H18B H 0.7263 0.9836 0.8743 0.092 Uiso 1 1 calc R . . H18C H 0.6741 0.8494 0.8237 0.092 Uiso 1 1 calc R . . N5 N 0.91159(14) 0.89312(11) 0.85027(11) 0.0439(3) Uani 1 1 d . . . N6 N 1.18764(14) 0.96733(11) 0.88586(11) 0.0442(3) Uani 1 1 d . . . O7 O 0.99541(15) 1.07834(11) 0.87253(11) 0.0623(3) Uani 1 1 d . . . O8 O 1.37542(14) 0.85107(13) 0.88652(14) 0.0788(4) Uani 1 1 d . . . O9 O 0.83123(16) 0.71290(12) 0.84402(15) 0.0785(4) Uani 1 1 d . . . C19 C 0.4688(2) 0.60301(17) 0.6866(2) 0.0685(5) Uani 1 1 d . . . H19A H 0.4210 0.6710 0.7225 0.103 Uiso 1 1 calc R . . H19B H 0.4278 0.5716 0.6073 0.103 Uiso 1 1 calc R . . H19C H 0.5826 0.6229 0.6961 0.103 Uiso 1 1 calc R . . C20 C 0.4854(3) 0.5579(2) 0.86125(18) 0.0739(6) Uani 1 1 d . . . H20A H 0.6000 0.5728 0.8748 0.111 Uiso 1 1 calc R . . H20B H 0.4498 0.5002 0.8912 0.111 Uiso 1 1 calc R . . H20C H 0.4423 0.6280 0.8978 0.111 Uiso 1 1 calc R . . N7 N 0.43068(17) 0.51629(12) 0.73858(13) 0.0526(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 C1 0.0416(8) 0.0467(8) 0.0519(9) 0.0165(7) 0.0092(7) 0.0173(7) C2 0.0517(9) 0.0543(9) 0.0403(8) 0.0152(7) 0.0075(7) 0.0178(7) C3 0.0429(8) 0.0474(8) 0.0487(8) 0.0174(7) 0.0044(7) 0.0138(7) C4 0.0448(8) 0.0470(8) 0.0481(8) 0.0105(7) 0.0094(7) 0.0160(7) C5 0.0545(10) 0.0635(11) 0.0667(12) 0.0081(9) -0.0002(9) 0.0042(9) C6 0.0535(10) 0.0835(13) 0.0673(12) 0.0239(10) 0.0265(9) 0.0175(9) N1 0.0440(7) 0.0499(7) 0.0471(7) 0.0115(6) 0.0035(6) 0.0107(6) N2 0.0420(7) 0.0575(8) 0.0456(7) 0.0172(6) 0.0123(6) 0.0162(6) O1 0.0409(6) 0.0617(7) 0.0818(9) 0.0121(6) 0.0173(6) 0.0139(5) O2 0.0744(9) 0.0748(9) 0.0485(7) 0.0033(6) 0.0159(6) 0.0194(7) O3 0.0411(6) 0.0628(7) 0.0741(8) 0.0090(6) 0.0032(6) 0.0071(6) C7 0.0818(14) 0.0764(13) 0.0751(13) 0.0250(11) 0.0291(11) 0.0333(11) C8 0.0519(10) 0.0562(10) 0.0790(13) 0.0287(9) 0.0198(9) 0.0097(8) C9 0.0639(12) 0.0715(12) 0.0728(13) 0.0157(10) 0.0189(10) 0.0106(10) C10 0.0623(11) 0.0699(12) 0.0691(12) 0.0302(10) 0.0233(10) 0.0194(9) C11 0.0488(11) 0.0965(16) 0.124(2) 0.0600(15) 0.0219(12) 0.0135(10) C12 0.0564(10) 0.0594(10) 0.0620(11) 0.0304(9) 0.0072(9) 0.0146(8) N3 0.0552(8) 0.0553(8) 0.0611(9) 0.0270(7) 0.0195(7) 0.0178(7) N4 0.0462(8) 0.0638(9) 0.0777(10) 0.0399(8) 0.0176(7) 0.0151(7) O4 0.0754(10) 0.0796(10) 0.0796(10) 0.0185(8) -0.0049(8) 0.0077(8) O5 0.0548(9) 0.0823(10) 0.1436(16) 0.0213(10) 0.0359(9) 0.0031(7) O6 0.0856(12) 0.1172(14) 0.0975(12) 0.0183(10) 0.0493(10) 0.0273(10) C13 0.0396(8) 0.0522(8) 0.0369(7) 0.0163(6) 0.0056(6) 0.0092(6) C14 0.0483(10) 0.0695(12) 0.0765(13) 0.0283(10) 0.0053(9) -0.0080(8) C15 0.0367(8) 0.0559(9) 0.0493(9) 0.0096(7) 0.0050(6) 0.0109(7) C16 0.0470(9) 0.0529(9) 0.0586(10) 0.0192(8) 0.0089(7) 0.0136(7) C17 0.0415(8) 0.0476(8) 0.0504(9) 0.0085(7) 0.0091(7) 0.0045(7) C18 0.0345(8) 0.0776(12) 0.0675(11) 0.0197(10) 0.0024(7) 0.0121(8) N5 0.0323(6) 0.0533(7) 0.0440(7) 0.0137(6) 0.0064(5) 0.0087(5) N6 0.0348(6) 0.0504(7) 0.0444(7) 0.0143(6) 0.0051(5) 0.0024(5) O7 0.0623(8) 0.0585(7) 0.0729(8) 0.0317(6) 0.0041(6) 0.0155(6) O8 0.0368(7) 0.0784(9) 0.1089(12) 0.0169(8) 0.0062(7) 0.0166(6) O9 0.0523(8) 0.0582(8) 0.1162(12) 0.0215(8) 0.0166(8) -0.0049(6) C19 0.0594(11) 0.0588(11) 0.0906(15) 0.0311(10) 0.0118(10) 0.0058(9) C20 0.0664(12) 0.0781(13) 0.0686(13) 0.0173(11) 0.0113(10) -0.0007(10) N7 0.0354(7) 0.0481(7) 0.0696(9) 0.0135(7) 0.0126(6) 0.0064(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2500(19) . ? C1 C4 1.385(2) . ? C1 N1 1.405(2) . ? C2 O2 1.2246(19) . ? C2 N1 1.370(2) . ? C2 N2 1.375(2) . ? C3 O3 1.249(2) . ? C3 C4 1.389(2) . ? C3 N2 1.408(2) . ? C4 H4 0.9300 . ? C5 N1 1.461(2) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 N2 1.460(2) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 N3 1.468(2) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 O5 1.208(2) . ? C8 N3 1.356(3) . ? C8 C9 1.476(3) . ? C9 C10 1.479(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O6 1.204(2) . ? C10 N4 1.368(3) . ? C11 N4 1.469(2) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 O4 1.203(2) . ? C12 N4 1.383(2) . ? C12 N3 1.392(2) . ? C13 O7 1.2113(19) . ? C13 N6 1.3850(19) . ? C13 N5 1.384(2) . ? C14 N6 1.466(2) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 O8 1.2082(19) . ? C15 N6 1.372(2) . ? C15 C16 1.487(2) . ? C16 C17 1.485(2) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 O9 1.208(2) . ? C17 N5 1.375(2) . ? C18 N5 1.468(2) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 N7 1.473(2) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 N7 1.471(3) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? N7 H700 0.96(2) . ? N7 H701 0.97(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 O1 C1 C4 126.73(15) . . ? O1 C1 N1 116.70(14) . . ? C4 C1 N1 116.57(13) . . ? O2 C2 N1 121.45(16) . . ? O2 C2 N2 121.69(16) . . ? N1 C2 N2 116.86(13) . . ? O3 C3 C4 125.69(15) . . ? O3 C3 N2 118.06(14) . . ? C4 C3 N2 116.25(14) . . ? C1 C4 C3 123.08(14) . . ? C1 C4 H4 118.5 . . ? C3 C4 H4 118.5 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C2 N1 C1 123.60(14) . . ? C2 N1 C5 117.31(14) . . ? C1 N1 C5 119.07(14) . . ? C2 N2 C3 123.56(13) . . ? C2 N2 C6 117.69(14) . . ? C3 N2 C6 118.73(15) . . ? N3 C7 H7A 109.5 . . ? N3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O5 C8 N3 121.31(18) . . ? O5 C8 C9 121.4(2) . . ? N3 C8 C9 117.26(17) . . ? C8 C9 C10 118.74(18) . . ? C8 C9 H9A 107.6 . . ? C10 C9 H9A 107.6 . . ? C8 C9 H9B 107.6 . . ? C10 C9 H9B 107.6 . . ? H9A C9 H9B 107.1 . . ? O6 C10 N4 121.1(2) . . ? O6 C10 C9 121.9(2) . . ? N4 C10 C9 116.99(16) . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O4 C12 N4 121.27(18) . . ? O4 C12 N3 120.70(18) . . ? N4 C12 N3 118.03(17) . . ? C8 N3 C12 124.45(15) . . ? C8 N3 C7 119.27(16) . . ? C12 N3 C7 115.97(17) . . ? C10 N4 C12 124.36(16) . . ? C10 N4 C11 118.38(17) . . ? C12 N4 C11 117.21(18) . . ? O7 C13 N6 120.82(15) . . ? O7 C13 N5 120.69(14) . . ? N6 C13 N5 118.46(13) . . ? N6 C14 H14A 109.5 . . ? N6 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N6 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O8 C15 N6 120.98(16) . . ? O8 C15 C16 121.63(16) . . ? N6 C15 C16 117.35(13) . . ? C17 C16 C15 118.06(14) . . ? C17 C16 H16A 107.8 . . ? C15 C16 H16A 107.8 . . ? C17 C16 H16B 107.8 . . ? C15 C16 H16B 107.8 . . ? H16A C16 H16B 107.1 . . ? O9 C17 N5 121.22(15) . . ? O9 C17 C16 121.56(16) . . ? N5 C17 C16 117.22(14) . . ? N5 C18 H18A 109.5 . . ? N5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 N5 C13 124.31(13) . . ? C17 N5 C18 119.20(14) . . ? C13 N5 C18 116.43(14) . . ? C15 N6 C13 124.06(13) . . ? C15 N6 C14 118.69(14) . . ? C13 N6 C14 116.66(14) . . ? N7 C19 H19A 109.5 . . ? N7 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N7 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N7 C20 H20A 109.5 . . ? N7 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N7 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C20 N7 C19 113.39(16) . . ? C20 N7 H700 112.0(12) . . ? C19 N7 H700 106.9(12) . . ? C20 N7 H701 111.6(12) . . ? C19 N7 H701 107.0(12) . . ? H700 N7 H701 105.4(17) . . ? _diffrn_measured_fraction_theta_max 0.888 _diffrn_reflns_theta_full 28.48 _diffrn_measured_fraction_theta_full 0.888 _refine_diff_density_max 0.241 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.036