# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2011 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Harris, Kenneth' _publ_contact_author_email HarrisKDM@cardiff.ac.uk loop_ _publ_author_name J.Marti-Rujas B.Kariuki C.Hughes A.Morte-Rodenas K.Harris data_sp136m _database_code_depnum_ccdc_archive 'CCDC 809763' #TrackingRef 'rt-1-06.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H14 O2, 2(C H4 N2 O)' _chemical_formula_sum 'C8 H22 N4 O4' _chemical_formula_weight 238.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.1642(2) _cell_length_b 7.4945(3) _cell_length_c 8.4337(3) _cell_angle_alpha 94.823(2) _cell_angle_beta 96.022(3) _cell_angle_gamma 101.486(3) _cell_volume 316.26(2) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 937 _cell_measurement_theta_min 5.30 _cell_measurement_theta_max 66.62 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 130 _exptl_absorpt_coefficient_mu 0.835 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8247 _exptl_absorpt_correction_T_max 0.8920 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 6000 CCD' _diffrn_measurement_method 'CCD slices' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1982 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 5.30 _diffrn_reflns_theta_max 66.62 _reflns_number_total 1033 _reflns_number_gt 937 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution SHELXTL _computing_structure_refinement SHELXTL _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^)+(0.1082P)^2^+0.0250P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1033 _refine_ls_number_parameters 75 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1505 _refine_ls_wR_factor_gt 0.1465 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0110(3) 0.24761(19) -0.60938(17) 0.0346(4) Uani 1 1 d . . . C2 C -0.4279(3) 0.7242(2) -0.84455(19) 0.0424(5) Uani 1 1 d . . . H2A H -0.5074 0.8234 -0.8050 0.051 Uiso 1 1 calc R . . H2B H -0.5332 0.6664 -0.9444 0.051 Uiso 1 1 calc R . . C3 C -0.1494(3) 0.8023(2) -0.87714(19) 0.0404(5) Uani 1 1 d . . . H3A H -0.0757 0.7053 -0.9267 0.049 Uiso 1 1 calc R . . H3B H -0.0394 0.8500 -0.7763 0.049 Uiso 1 1 calc R . . C4 C -0.1402(3) 0.9549(2) -0.98660(18) 0.0397(5) Uani 1 1 d . . . H4A H -0.2417 0.9047 -1.0895 0.048 Uiso 1 1 calc R . . H4B H -0.2254 1.0475 -0.9402 0.048 Uiso 1 1 calc R . . N1 N 0.0165(3) 0.39050(18) -0.69474(17) 0.0457(4) Uani 1 1 d . . . H1C H 0.1655 0.4489 -0.7190 0.055 Uiso 1 1 calc R . . H1D H -0.1290 0.4240 -0.7254 0.055 Uiso 1 1 calc R . . N2 N -0.2224(2) 0.15931(18) -0.57402(17) 0.0458(5) Uani 1 1 d . . . H2C H -0.2297 0.0668 -0.5196 0.055 Uiso 1 1 calc R . . H2D H -0.3659 0.1947 -0.6056 0.055 Uiso 1 1 calc R . . O2 O -0.4379(2) 0.59237(14) -0.72981(14) 0.0452(4) Uani 1 1 d . . . H1 H -0.3825 0.6453 -0.6399 0.068 Uiso 1 1 calc R . . O1 O 0.2228(2) 0.19739(14) -0.56395(13) 0.0434(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 C1 0.0318(8) 0.0348(8) 0.0396(8) 0.0070(6) 0.0064(5) 0.0104(6) C2 0.0367(10) 0.0435(10) 0.0500(9) 0.0195(7) 0.0060(6) 0.0093(7) C3 0.0384(9) 0.0422(9) 0.0452(9) 0.0171(6) 0.0102(6) 0.0117(7) C4 0.0379(9) 0.0434(9) 0.0417(9) 0.0161(6) 0.0091(6) 0.0105(7) N1 0.0381(8) 0.0433(8) 0.0609(9) 0.0223(6) 0.0093(6) 0.0125(6) N2 0.0308(8) 0.0473(8) 0.0652(10) 0.0220(6) 0.0121(6) 0.0124(6) O2 0.0414(7) 0.0424(7) 0.0546(7) 0.0223(5) 0.0109(5) 0.0063(5) O1 0.0292(6) 0.0473(7) 0.0595(8) 0.0227(5) 0.0095(4) 0.0127(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 C1 O1 1.2588(18) . ? C1 N2 1.331(2) . ? C1 N1 1.3371(19) . ? C2 O2 1.4377(17) . ? C2 C3 1.504(2) . ? C3 C4 1.525(2) . ? C4 C4 1.520(3) 2_573 ? 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 N2 120.73(14) . . ? O1 C1 N1 120.53(14) . . ? N2 C1 N1 118.73(13) . . ? O2 C2 C3 113.08(12) . . ? C2 C3 C4 112.30(13) . . ? C4 C4 C3 113.65(16) 2_573 . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 66.62 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.208 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.059 # Attachment 'rt-1-08.cif' data_kdm0703 _database_code_depnum_ccdc_archive 'CCDC 809764' #TrackingRef 'rt-1-08.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H18 O2, 2(C H4 N2 O)' _chemical_formula_sum 'C10 H26 N4 O4' _chemical_formula_weight 266.35 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 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 10.6090(5) _cell_length_b 5.2000(3) _cell_length_c 14.3020(7) _cell_angle_alpha 90.00 _cell_angle_beta 112.627(4) _cell_angle_gamma 90.00 _cell_volume 728.27(6) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1080 _cell_measurement_theta_min 4.12 _cell_measurement_theta_max 27.35 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9771 _exptl_absorpt_correction_T_max 0.9907 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6704 _diffrn_reflns_av_R_equivalents 0.0881 _diffrn_reflns_av_sigmaI/netI 0.0646 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_max 27.35 _reflns_number_total 1641 _reflns_number_gt 1080 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997' _computing_structure_solution 'Sir-92 (A. Altomare et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-99 for Windows (Farrugia, 1995)' _computing_publication_material 'WinGX publication routines (Farrugia, 1995)' _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^)+(0.0732P)^2^+0.1058P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1641 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0985 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1620 _refine_ls_wR_factor_gt 0.1428 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 O1 O 0.94558(14) 0.2108(2) 0.63648(8) 0.0440(4) Uani 1 1 d . . . N2 N 0.82916(18) 0.4218(3) 0.49136(11) 0.0451(5) Uani 1 1 d . . . H2C H 0.8085 0.2800 0.4580 0.054 Uiso 1 1 calc R . . H2D H 0.8014 0.5658 0.4608 0.054 Uiso 1 1 calc R . . C1 C 0.90433(18) 0.4184(3) 0.59076(12) 0.0316(4) Uani 1 1 d . . . N1 N 0.93344(17) 0.6425(3) 0.63928(11) 0.0439(5) Uani 1 1 d . . . H1B H 0.9815 0.6465 0.7033 0.053 Uiso 1 1 calc R . . H1A H 0.9042 0.7834 0.6066 0.053 Uiso 1 1 calc R . . O2 O 0.80991(14) 0.5747(3) 0.88220(9) 0.0456(4) Uani 1 1 d . . . H2 H 0.8845 0.6131 0.8816 0.068 Uiso 1 1 calc R . . C2 C 0.7127(2) 0.5469(4) 0.78027(14) 0.0427(5) Uani 1 1 d . . . H2A H 0.6317 0.4625 0.7813 0.051 Uiso 1 1 calc R . . H2B H 0.7513 0.4373 0.7432 0.051 Uiso 1 1 calc R . . C3 C 0.67210(19) 0.8000(4) 0.72551(13) 0.0400(5) Uani 1 1 d . . . H3A H 0.7537 0.8907 0.7290 0.048 Uiso 1 1 calc R . . H3B H 0.6268 0.9045 0.7594 0.048 Uiso 1 1 calc R . . C4 C 0.5775(2) 0.7671(4) 0.61497(12) 0.0423(5) Uani 1 1 d . . . H4A H 0.6199 0.6507 0.5828 0.051 Uiso 1 1 calc R . . H4B H 0.4931 0.6883 0.6119 0.051 Uiso 1 1 calc R . . C5 C 0.5439(2) 1.0178(4) 0.55570(14) 0.0454(5) Uani 1 1 d . . . H5A H 0.4966 1.1305 0.5855 0.055 Uiso 1 1 calc R . . H5B H 0.6284 1.1015 0.5619 0.055 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 0.0589(9) 0.0296(8) 0.0377(7) 0.0042(5) 0.0120(6) 0.0024(6) N2 0.0600(11) 0.0361(10) 0.0325(8) 0.0007(6) 0.0103(7) 0.0004(7) C1 0.0344(9) 0.0299(10) 0.0326(9) 0.0009(7) 0.0152(7) -0.0008(7) N1 0.0606(11) 0.0297(9) 0.0381(8) -0.0004(6) 0.0153(8) 0.0006(7) O2 0.0508(8) 0.0445(9) 0.0352(7) 0.0053(5) 0.0095(6) 0.0002(7) C2 0.0471(11) 0.0405(12) 0.0371(9) 0.0010(8) 0.0125(9) -0.0048(9) C3 0.0419(11) 0.0390(11) 0.0371(9) 0.0024(8) 0.0130(8) 0.0037(8) C4 0.0450(11) 0.0389(11) 0.0382(10) 0.0027(8) 0.0106(9) 0.0005(8) C5 0.0506(12) 0.0406(11) 0.0387(10) 0.0044(8) 0.0101(9) -0.0007(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.251(2) . ? N2 C1 1.336(2) . ? N2 H2C 0.8600 . ? N2 H2D 0.8600 . ? C1 N1 1.330(2) . ? N1 H1B 0.8600 . ? N1 H1A 0.8600 . ? O2 C2 1.433(2) . ? O2 H2 0.8200 . ? C2 C3 1.507(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.521(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.520(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C5 1.516(4) 3_676 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N2 H2C 120.0 . . ? C1 N2 H2D 120.0 . . ? H2C N2 H2D 120.0 . . ? O1 C1 N1 121.26(15) . . ? O1 C1 N2 120.89(16) . . ? N1 C1 N2 117.85(16) . . ? C1 N1 H1B 120.0 . . ? C1 N1 H1A 120.0 . . ? H1B N1 H1A 120.0 . . ? C2 O2 H2 109.5 . . ? O2 C2 C3 112.99(16) . . ? O2 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? O2 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 112.59(16) . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 113.74(17) . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C5 C5 C4 113.5(2) 3_676 . ? C5 C5 H5A 108.9 3_676 . ? C4 C5 H5A 108.9 . . ? C5 C5 H5B 108.9 3_676 . ? C4 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C2 C3 C4 175.53(16) . . . . ? C2 C3 C4 C5 -175.42(17) . . . . ? C3 C4 C5 C5 176.7(2) . . . 3_676 ? 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 N2 H2C O2 0.86 2.14 2.983(2) 165.8 4_565 N2 H2D O2 0.86 2.20 3.015(2) 157.8 4_575 N1 H1B O1 0.86 2.14 2.9818(19) 164.6 2_756 O2 H2 O1 0.82 1.98 2.799(2) 173.6 2_756 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.35 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.191 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.050 # Attachment 'rt-1-10.cif' data_kdm0705 _database_code_depnum_ccdc_archive 'CCDC 809765' #TrackingRef 'rt-1-10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H22 O2, 2(C H4 N2 O)' _chemical_formula_sum 'C12 H30 N4 O4' _chemical_formula_weight 294.40 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.1899(2) _cell_length_b 7.4045(3) _cell_length_c 11.2621(5) _cell_angle_alpha 99.469(2) _cell_angle_beta 96.754(2) _cell_angle_gamma 101.269(3) _cell_volume 413.61(3) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1176 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 27.52 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 162 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9489 _exptl_absorpt_correction_T_max 0.9869 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4915 _diffrn_reflns_av_R_equivalents 0.1220 _diffrn_reflns_av_sigmaI/netI 0.0943 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.52 _reflns_number_total 1869 _reflns_number_gt 1176 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997' _computing_structure_solution 'Sir-92 (A. Altomare et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-99 for Windows (Farrugia, 1995)' _computing_publication_material 'WinGX publication routines (Farrugia, 1995)' _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^)+(0.1024P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.17(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1869 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0999 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1962 _refine_ls_wR_factor_gt 0.1702 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0777(3) 0.2875(3) 0.58519(15) 0.0367(5) Uani 1 1 d . . . C2 C -0.2050(4) 0.8451(3) 0.76207(17) 0.0450(5) Uani 1 1 d . . . H2A H -0.0645 0.9239 0.7322 0.054 Uiso 1 1 calc R . . H2B H -0.1277 0.8139 0.8367 0.054 Uiso 1 1 calc R . . C3 C -0.4140(3) 0.9537(2) 0.79006(16) 0.0410(5) Uani 1 1 d . . . H3A H -0.5471 0.8788 0.8262 0.049 Uiso 1 1 calc R . . H3B H -0.5013 0.9760 0.7145 0.049 Uiso 1 1 calc R . . C4 C -0.3016(4) 1.1412(3) 0.87635(17) 0.0455(5) Uani 1 1 d . . . H4A H -0.2162 1.1185 0.9522 0.055 Uiso 1 1 calc R . . H4B H -0.1665 1.2150 0.8407 0.055 Uiso 1 1 calc R . . C5 C -0.5091(4) 1.2533(3) 0.90399(17) 0.0462(5) Uani 1 1 d . . . H5A H -0.6403 1.1814 0.9426 0.055 Uiso 1 1 calc R . . H5B H -0.5995 1.2714 0.8279 0.055 Uiso 1 1 calc R . . C6 C -0.3971(4) 1.4432(3) 0.98571(18) 0.0490(6) Uani 1 1 d . . . H6A H -0.2659 1.5149 0.9469 0.059 Uiso 1 1 calc R . . H6B H -0.3062 1.4248 1.0617 0.059 Uiso 1 1 calc R . . N1 N -0.1724(3) 0.1910(2) 0.55587(14) 0.0484(5) Uani 1 1 d . . . H1C H -0.2075 0.0787 0.5138 0.058 Uiso 1 1 calc R . . H1D H -0.2992 0.2407 0.5789 0.058 Uiso 1 1 calc R . . N2 N 0.1250(3) 0.4615(2) 0.65001(15) 0.0486(5) Uani 1 1 d . . . H2C H 0.2853 0.5268 0.6697 0.058 Uiso 1 1 calc R . . H2D H -0.0049 0.5085 0.6721 0.058 Uiso 1 1 calc R . . O1 O 0.2653(2) 0.21681(17) 0.55218(11) 0.0464(5) Uani 1 1 d . . . O2 O -0.3074(3) 0.67587(18) 0.67352(12) 0.0486(4) Uani 1 1 d . . . H2 H -0.3169 0.7005 0.6050 0.073 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0400(10) 0.0323(10) 0.0390(9) 0.0072(7) 0.0055(7) 0.0111(8) C2 0.0466(10) 0.0342(11) 0.0502(11) -0.0029(8) 0.0041(8) 0.0103(8) C3 0.0435(10) 0.0313(11) 0.0448(10) -0.0016(8) 0.0067(8) 0.0078(8) C4 0.0484(11) 0.0349(11) 0.0500(11) -0.0010(8) 0.0042(9) 0.0114(9) C5 0.0524(11) 0.0332(11) 0.0500(11) -0.0027(8) 0.0044(9) 0.0133(9) C6 0.0547(12) 0.0330(11) 0.0556(12) -0.0032(9) 0.0079(9) 0.0108(9) N1 0.0374(9) 0.0372(10) 0.0679(11) 0.0005(8) 0.0095(7) 0.0087(7) N2 0.0460(9) 0.0332(10) 0.0635(11) -0.0032(8) 0.0078(7) 0.0121(7) O1 0.0360(7) 0.0360(8) 0.0640(9) -0.0034(6) 0.0101(6) 0.0099(6) O2 0.0556(8) 0.0315(8) 0.0555(8) -0.0043(6) 0.0099(7) 0.0116(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 1.257(2) . ? C1 N1 1.328(2) . ? C1 N2 1.333(2) . ? C2 O2 1.432(2) . ? C2 C3 1.504(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.522(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.513(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.513(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C6 1.516(4) 2_487 ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? N1 H1C 0.8600 . ? N1 H1D 0.8600 . ? N2 H2C 0.8600 . ? N2 H2D 0.8600 . ? O2 H2 0.8200 . ? 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 N1 120.77(17) . . ? O1 C1 N2 120.81(16) . . ? N1 C1 N2 118.42(16) . . ? O2 C2 C3 112.91(15) . . ? O2 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? O2 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 112.99(15) . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 113.60(15) . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C4 C5 C6 113.88(17) . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5B 108.8 . . ? C6 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C5 C6 C6 114.4(2) . 2_487 ? C5 C6 H6A 108.7 . . ? C6 C6 H6A 108.7 2_487 . ? C5 C6 H6B 108.7 . . ? C6 C6 H6B 108.7 2_487 . ? H6A C6 H6B 107.6 . . ? C1 N1 H1C 120.0 . . ? C1 N1 H1D 120.0 . . ? H1C N1 H1D 120.0 . . ? C1 N2 H2C 120.0 . . ? C1 N2 H2D 120.0 . . ? H2C N2 H2D 120.0 . . ? C2 O2 H2 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C2 C3 C4 -175.37(15) . . . . ? C2 C3 C4 C5 179.20(17) . . . . ? C3 C4 C5 C6 -177.69(16) . . . . ? C4 C5 C6 C6 -179.9(2) . . . 2_487 ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.258 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.063 # Attachment 'rt-1-12.cif' data_kdm0729 _database_code_depnum_ccdc_archive 'CCDC 809766' #TrackingRef 'rt-1-12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H26 O2, 2(C H4 N2 O)' _chemical_formula_sum 'C14 H34 N4 O4' _chemical_formula_weight 322.45 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 5.1986(3) _cell_length_b 7.4194(5) _cell_length_c 12.4230(9) _cell_angle_alpha 88.755(4) _cell_angle_beta 79.063(4) _cell_angle_gamma 78.612(3) _cell_volume 461.13(5) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1263 _cell_measurement_theta_min 3.24 _cell_measurement_theta_max 27.52 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.161 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 178 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9589 _exptl_absorpt_correction_T_max 0.9891 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4782 _diffrn_reflns_av_R_equivalents 0.0710 _diffrn_reflns_av_sigmaI/netI 0.0798 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 27.52 _reflns_number_total 2088 _reflns_number_gt 1263 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997' _computing_structure_solution 'Sir-92 (A. Altomare et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-99 for Windows (Farrugia, 1995)' _computing_publication_material 'WinGX publication routines (Farrugia, 1995)' _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^)+(0.0836P)^2^+0.0529P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2088 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1154 _refine_ls_R_factor_gt 0.0658 _refine_ls_wR_factor_ref 0.1857 _refine_ls_wR_factor_gt 0.1572 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 O2 O 0.2062(3) 0.3721(2) -0.15620(11) 0.0487(4) Uani 1 1 d . . . H2 H 0.1954 0.3297 -0.0943 0.073 Uiso 1 1 calc R . . O1 O 0.2303(3) 0.2029(2) 0.04714(11) 0.0472(4) Uani 1 1 d . . . N1 N 0.3643(4) 0.4203(3) 0.13446(14) 0.0500(5) Uani 1 1 d . . . H1B H 0.2025 0.4800 0.1525 0.060 Uiso 1 1 calc R . . H1A H 0.4924 0.4614 0.1540 0.060 Uiso 1 1 calc R . . N2 N 0.6680(3) 0.1753(3) 0.05012(14) 0.0493(5) Uani 1 1 d . . . H2C H 0.7056 0.0741 0.0128 0.059 Uiso 1 1 calc R . . H2D H 0.7934 0.2185 0.0704 0.059 Uiso 1 1 calc R . . C1 C 0.4163(4) 0.2649(3) 0.07642(15) 0.0371(5) Uani 1 1 d . . . C2 C 0.3167(4) 0.2263(3) -0.23575(17) 0.0472(6) Uani 1 1 d . . . H2A H 0.4546 0.1398 -0.2086 0.057 Uiso 1 1 calc R . . H2B H 0.3997 0.2772 -0.3030 0.057 Uiso 1 1 calc R . . C3 C 0.1098(4) 0.1253(3) -0.26066(16) 0.0413(5) Uani 1 1 d . . . H3A H -0.0210 0.2100 -0.2929 0.050 Uiso 1 1 calc R . . H3B H 0.0175 0.0824 -0.1926 0.050 Uiso 1 1 calc R . . C4 C 0.2288(4) -0.0381(3) -0.33847(17) 0.0453(6) Uani 1 1 d . . . H4A H 0.3181 0.0056 -0.4069 0.054 Uiso 1 1 calc R . . H4B H 0.3627 -0.1209 -0.3068 0.054 Uiso 1 1 calc R . . C5 C 0.0249(4) -0.1444(3) -0.36284(17) 0.0458(6) Uani 1 1 d . . . H5A H -0.0685 -0.1845 -0.2942 0.055 Uiso 1 1 calc R . . H5B H -0.1056 -0.0626 -0.3967 0.055 Uiso 1 1 calc R . . C6 C 0.1445(5) -0.3105(3) -0.43730(17) 0.0490(6) Uani 1 1 d . . . H6A H 0.2742 -0.3927 -0.4032 0.059 Uiso 1 1 calc R . . H6B H 0.2390 -0.2704 -0.5057 0.059 Uiso 1 1 calc R . . C7 C -0.0595(4) -0.4167(3) -0.46247(16) 0.0470(6) Uani 1 1 d . . . H7A H -0.1896 -0.3343 -0.4963 0.056 Uiso 1 1 calc R . . H7B H -0.1536 -0.4570 -0.3940 0.056 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 0.0518(10) 0.0423(9) 0.0553(9) -0.0163(7) -0.0126(7) -0.0128(7) O1 0.0336(8) 0.0481(10) 0.0624(9) -0.0157(7) -0.0102(6) -0.0113(7) N1 0.0412(11) 0.0463(11) 0.0648(11) -0.0175(9) -0.0089(8) -0.0131(9) N2 0.0343(11) 0.0473(11) 0.0699(12) -0.0121(9) -0.0130(8) -0.0118(9) C1 0.0337(11) 0.0407(12) 0.0392(10) -0.0028(9) -0.0072(8) -0.0123(9) C2 0.0437(13) 0.0453(13) 0.0549(12) -0.0137(10) -0.0067(10) -0.0154(10) C3 0.0401(12) 0.0408(13) 0.0453(11) -0.0094(9) -0.0087(9) -0.0114(10) C4 0.0459(13) 0.0431(13) 0.0473(11) -0.0128(10) -0.0060(9) -0.0110(10) C5 0.0457(13) 0.0429(13) 0.0505(12) -0.0124(10) -0.0056(10) -0.0149(10) C6 0.0490(14) 0.0441(13) 0.0560(13) -0.0150(10) -0.0090(10) -0.0136(11) C7 0.0489(14) 0.0408(13) 0.0527(13) -0.0141(10) -0.0081(10) -0.0120(11) _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 C2 1.436(2) . ? O1 C1 1.263(2) . ? N1 C1 1.328(3) . ? N2 C1 1.328(3) . ? C2 C3 1.506(3) . ? C3 C4 1.521(3) . ? C4 C5 1.517(3) . ? C5 C6 1.514(3) . ? C6 C7 1.519(3) . ? C7 C7 1.520(4) 2_544 ? 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 N1 120.72(19) . . ? O1 C1 N2 120.64(19) . . ? N1 C1 N2 118.64(18) . . ? O2 C2 C3 112.71(17) . . ? C2 C3 C4 112.92(17) . . ? C5 C4 C3 113.86(17) . . ? C6 C5 C4 113.87(18) . . ? C5 C6 C7 114.00(19) . . ? C6 C7 C7 114.2(2) . 2_544 ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.207 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.056 # Attachment 'rt-1-14.cif' data_kdm0739 _database_code_depnum_ccdc_archive 'CCDC 809767' #TrackingRef 'rt-1-14.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H30 O2, 2(C H4 N2 O)' _chemical_formula_sum 'C16 H38 N4 O4' _chemical_formula_weight 350.50 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 5.2049(3) _cell_length_b 7.4169(5) _cell_length_c 13.6376(9) _cell_angle_alpha 95.676(4) _cell_angle_beta 97.552(4) _cell_angle_gamma 101.479(3) _cell_volume 507.21(6) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1458 _cell_measurement_theta_min 3.38 _cell_measurement_theta_max 27.54 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max .25 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.148 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 194 _exptl_absorpt_coefficient_mu 0.082 _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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6171 _diffrn_reflns_av_R_equivalents 0.0863 _diffrn_reflns_av_sigmaI/netI 0.0791 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 27.54 _reflns_number_total 2294 _reflns_number_gt 1458 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997' _computing_structure_solution 'Sir-92 (A. Altomare et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-99 for Windows (Farrugia, 1995)' _computing_publication_material 'WinGX publication routines (Farrugia, 1995)' _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^)+(0.0937P)^2^+0.0617P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2294 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1142 _refine_ls_R_factor_gt 0.0706 _refine_ls_wR_factor_ref 0.1990 _refine_ls_wR_factor_gt 0.1732 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2292(3) 0.19060(19) 0.95708(10) 0.0482(4) Uani 1 1 d . . . O2 O -0.4239(3) 0.5891(2) 0.85793(10) 0.0504(4) Uani 1 1 d . . . H2 H -0.3835 0.6472 0.9141 0.076 Uiso 1 1 calc R . . C3 C -0.6076(4) 0.8102(3) 0.76319(14) 0.0426(5) Uani 1 1 d . . . H3A H -0.6416 0.8702 0.8252 0.051 Uiso 1 1 calc R . . H3B H -0.7660 0.7180 0.7341 0.051 Uiso 1 1 calc R . . C7 C -0.9441(4) 1.3029(3) 0.58053(15) 0.0478(5) Uani 1 1 d . . . H7A H -0.9784 1.3615 0.6429 0.057 Uiso 1 1 calc R . . H7B H -1.1035 1.2124 0.5506 0.057 Uiso 1 1 calc R . . C4 C -0.5533(4) 0.9541(3) 0.69238(15) 0.0459(5) Uani 1 1 d . . . H4A H -0.3926 1.0446 0.7209 0.055 Uiso 1 1 calc R . . H4B H -0.5226 0.8935 0.6300 0.055 Uiso 1 1 calc R . . C2 C -0.3812(4) 0.7147(3) 0.78530(15) 0.0467(5) Uani 1 1 d . . . H2A H -0.3564 0.6466 0.7240 0.056 Uiso 1 1 calc R . . H2B H -0.2198 0.8076 0.8094 0.056 Uiso 1 1 calc R . . C5 C -0.7776(4) 1.0547(3) 0.67088(15) 0.0467(5) Uani 1 1 d . . . H5A H -0.9370 0.9647 0.6404 0.056 Uiso 1 1 calc R . . H5B H -0.8122 1.1120 0.7335 0.056 Uiso 1 1 calc R . . N1 N 0.0246(4) 0.3875(3) 0.87773(13) 0.0513(5) Uani 1 1 d . . . H9A H 0.1715 0.4432 0.8617 0.062 Uiso 1 1 calc R . . H9B H -0.1196 0.4237 0.8598 0.062 Uiso 1 1 calc R . . C6 C -0.7202(4) 1.2026(3) 0.60286(15) 0.0498(6) Uani 1 1 d . . . H6A H -0.6843 1.1454 0.5405 0.060 Uiso 1 1 calc R . . H6B H -0.5613 1.2929 0.6336 0.060 Uiso 1 1 calc R . . C8 C -0.8879(4) 1.4497(3) 0.51126(15) 0.0483(6) Uani 1 1 d . . . H8A H -0.7285 1.5401 0.5412 0.058 Uiso 1 1 calc R . . H8B H -0.8535 1.3911 0.4490 0.058 Uiso 1 1 calc R . . N2 N -0.2099(3) 0.1629(3) 0.95434(12) 0.0503(5) Uani 1 1 d . . . H10A H -0.2171 0.0712 0.9886 0.060 Uiso 1 1 calc R . . H10B H -0.3516 0.2014 0.9356 0.060 Uiso 1 1 calc R . . C1 C 0.0203(4) 0.2452(3) 0.93035(13) 0.0379(5) 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 0.0360(8) 0.0531(10) 0.0630(9) 0.0241(7) 0.0114(6) 0.0170(7) O2 0.0542(9) 0.0478(9) 0.0554(8) 0.0243(7) 0.0071(7) 0.0184(7) C3 0.0422(11) 0.0432(12) 0.0463(11) 0.0159(9) 0.0085(8) 0.0127(9) C7 0.0513(12) 0.0469(13) 0.0519(12) 0.0191(9) 0.0105(10) 0.0185(10) C4 0.0449(11) 0.0491(13) 0.0493(11) 0.0203(9) 0.0093(9) 0.0156(10) C2 0.0469(12) 0.0474(13) 0.0536(11) 0.0219(9) 0.0124(9) 0.0181(10) C5 0.0508(12) 0.0465(13) 0.0503(11) 0.0201(9) 0.0116(9) 0.0187(10) N1 0.0472(10) 0.0511(11) 0.0650(11) 0.0271(9) 0.0129(8) 0.0204(9) C6 0.0532(13) 0.0496(14) 0.0536(12) 0.0216(10) 0.0109(10) 0.0183(11) C8 0.0515(13) 0.0482(13) 0.0521(11) 0.0210(10) 0.0100(9) 0.0186(11) N2 0.0361(9) 0.0524(11) 0.0685(11) 0.0225(9) 0.0115(8) 0.0147(8) C1 0.0367(10) 0.0385(11) 0.0409(10) 0.0063(8) 0.0056(8) 0.0131(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 1.257(2) . ? O2 C2 1.434(2) . ? C3 C2 1.504(3) . ? C3 C4 1.519(3) . ? C7 C6 1.517(3) . ? C7 C8 1.520(3) . ? C4 C5 1.518(3) . ? C5 C6 1.516(3) . ? N1 C1 1.332(2) . ? C8 C8 1.520(4) 2_386 ? N2 C1 1.329(3) . ? 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 C3 C4 112.83(16) . . ? C6 C7 C8 113.91(18) . . ? C5 C4 C3 113.53(17) . . ? O2 C2 C3 112.81(16) . . ? C6 C5 C4 113.60(17) . . ? C5 C6 C7 113.90(18) . . ? C8 C8 C7 114.0(2) 2_386 . ? O1 C1 N2 120.80(18) . . ? O1 C1 N1 120.78(18) . . ? N2 C1 N1 118.42(17) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.289 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.051 # Attachment 'rt-1-16.cif' data_diol16h _database_code_depnum_ccdc_archive 'CCDC 809768' #TrackingRef 'rt-1-16.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H34 O2, 2(C H4 N2 O)' _chemical_formula_sum 'C18 H42 N4 O4' _chemical_formula_weight 378.56 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' O O 0.0106 0.0060 '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' _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 5.1973(5) _cell_length_b 7.3964(12) _cell_length_c 15.0141(16) _cell_angle_alpha 103.295(4) _cell_angle_beta 92.698(3) _cell_angle_gamma 101.711(5) _cell_volume 547.33(12) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1615 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 24.30 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.148 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 210 _exptl_absorpt_coefficient_mu 0.081 _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 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-axis IIc Image plate' _diffrn_measurement_method 'Image plate slices' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3090 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 24.30 _reflns_number_total 1707 _reflns_number_gt 1615 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC Software' _computing_cell_refinement 'MSC Software' _computing_data_reduction 'MSC Software' _computing_structure_solution SHELXS86 _computing_structure_refinement SHELXL97 _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 fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1860P)^2^+0.0000P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1707 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0589 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.1650 _refine_ls_wR_factor_gt 0.1649 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.2641(3) 0.6812(2) 0.4609(1) 0.048(1) Uani 1 1 d . . . O2 O 0.0982(3) 0.0575(2) 0.3705(1) 0.051(1) Uani 1 1 d . . . N1 N -0.7031(3) 0.6528(3) 0.4584(1) 0.052(1) Uani 1 1 d . . . N2 N -0.4577(3) 0.8597(3) 0.3874(1) 0.051(1) Uani 1 1 d . . . C1 C -0.4685(4) 0.7298(3) 0.4362(1) 0.039(1) Uani 1 1 d . . . C3 C -0.0711(4) 0.2554(3) 0.2830(1) 0.044(1) Uani 1 1 d . . . C8 C -0.3136(4) 0.8390(3) 0.0523(2) 0.049(1) Uani 1 1 d . . . C4 C -0.0063(4) 0.3835(3) 0.2178(1) 0.048(1) Uani 1 1 d . . . C7 C -0.3794(4) 0.7079(3) 0.1156(1) 0.049(1) Uani 1 1 d . . . C5 C -0.2260(4) 0.4793(3) 0.1982(1) 0.049(1) Uani 1 1 d . . . C2 C 0.1513(4) 0.1656(3) 0.3034(1) 0.049(1) Uani 1 1 d . . . C9 C -0.5334(4) 0.9346(3) 0.0319(1) 0.048(1) Uani 1 1 d . . . C6 C -0.1591(4) 0.6125(3) 0.1361(2) 0.050(1) Uani 1 1 d . . . H92 H -0.5726 1.0044 0.0880 0.075 Uiso 1 1 d . . . H2 H 0.1447 0.1752 0.4400 0.075 Uiso 1 1 d . . . H72 H -0.4293 0.7706 0.1738 0.075 Uiso 1 1 d . . . H62 H 0.0122 0.7148 0.1674 0.075 Uiso 1 1 d . . . H41 H 0.0282 0.3075 0.1568 0.075 Uiso 1 1 d . . . H11 H -0.6035 0.8990 0.3772 0.075 Uiso 1 1 d . . . H12 H -0.3028 0.9128 0.3797 0.075 Uiso 1 1 d . . . H13 H -0.7120 0.5594 0.4901 0.075 Uiso 1 1 d . . . H14 H -0.8452 0.6799 0.4422 0.075 Uiso 1 1 d . . . H32 H -0.1221 0.3259 0.3363 0.075 Uiso 1 1 d . . . H31 H -0.2318 0.1557 0.2595 0.075 Uiso 1 1 d . . . H51 H -0.3810 0.3875 0.1695 0.075 Uiso 1 1 d . . . H52 H -0.2788 0.5415 0.2535 0.075 Uiso 1 1 d . . . H42 H 0.1526 0.4779 0.2422 0.075 Uiso 1 1 d . . . H61 H -0.1042 0.5520 0.0767 0.075 Uiso 1 1 d . . . H21 H 0.1856 0.0725 0.2479 0.075 Uiso 1 1 d . . . H22 H 0.3175 0.2681 0.3209 0.075 Uiso 1 1 d . . . H82 H -0.1386 0.9372 0.0791 0.075 Uiso 1 1 d . . . H81 H -0.2596 0.7655 -0.0059 0.075 Uiso 1 1 d . . . H71 H -0.5443 0.6099 0.0916 0.075 Uiso 1 1 d . . . H91 H -0.7096 0.8254 0.0052 0.075 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 0.036(1) 0.060(1) 0.061(1) 0.032(1) 0.006(1) 0.018(1) O2 0.052(1) 0.054(1) 0.056(1) 0.031(1) 0.002(1) 0.017(1) N1 0.034(1) 0.060(1) 0.071(1) 0.031(1) 0.007(1) 0.013(1) N2 0.046(1) 0.056(1) 0.065(1) 0.033(1) 0.009(1) 0.020(1) C1 0.037(1) 0.041(1) 0.041(1) 0.011(1) 0.002(1) 0.014(1) C3 0.043(1) 0.051(1) 0.048(1) 0.023(1) 0.005(1) 0.016(1) C8 0.053(1) 0.053(1) 0.053(1) 0.029(1) 0.005(1) 0.021(1) C4 0.049(1) 0.055(1) 0.050(1) 0.028(1) 0.007(1) 0.020(1) C7 0.051(1) 0.056(1) 0.052(1) 0.029(1) 0.007(1) 0.022(1) C5 0.052(1) 0.056(1) 0.050(1) 0.026(1) 0.007(1) 0.024(1) C2 0.048(1) 0.055(1) 0.055(1) 0.029(1) 0.008(1) 0.020(1) C9 0.052(1) 0.053(1) 0.050(1) 0.026(1) 0.007(1) 0.020(1) C6 0.051(1) 0.057(1) 0.055(1) 0.031(1) 0.007(1) 0.021(1) _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 1.255(2) . ? O2 C2 1.427(2) . ? N1 C1 1.329(2) . ? N2 C1 1.330(2) . ? C3 C2 1.498(3) . ? C3 C4 1.516(3) . ? C8 C7 1.510(3) . ? C8 C9 1.514(3) . ? C4 C5 1.512(3) . ? C7 C6 1.516(3) . ? C5 C6 1.509(3) . ? C9 C9 1.514(4) 2_475 ? O2 H2 1.174 . ? N1 H13 0.919 . ? N1 H14 0.843 . ? N2 H11 0.884 . ? N2 H12 0.847 . ? C3 H32 0.931 . ? C3 H31 0.984 . ? C8 H82 1.039 . ? C8 H81 1.002 . ? C4 H41 1.003 . ? C4 H42 0.961 . ? C7 H72 0.964 . ? C7 H71 0.994 . ? C5 H51 0.952 . ? C5 H52 0.934 . ? C2 H21 0.999 . ? C2 H22 1.006 . ? C9 H92 0.937 . ? C9 H91 1.081 . ? C6 H62 1.053 . ? C6 H61 0.985 . ? 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 N1 120.8(2) . . ? O1 C1 N2 121.3(2) . . ? N1 C1 N2 117.9(2) . . ? C2 C3 C4 112.9(2) . . ? C7 C8 C9 114.2(2) . . ? C5 C4 C3 113.7(2) . . ? C8 C7 C6 114.2(2) . . ? C6 C5 C4 113.9(2) . . ? O2 C2 C3 112.8(2) . . ? C8 C9 C9 114.0(2) . 2_475 ? C5 C6 C7 114.3(2) . . ? C2 O2 H2 102.8 . . ? C1 N1 H13 118.1 . . ? C1 N1 H14 123.6 . . ? H13 N1 H14 118.2 . . ? C1 N2 H11 117.9 . . ? C1 N2 H12 114.4 . . ? H11 N2 H12 126.2 . . ? C2 C3 H32 111.9 . . ? C4 C3 H32 108.4 . . ? C2 C3 H31 109.6 . . ? C4 C3 H31 111.5 . . ? H32 C3 H31 102.1 . . ? C7 C8 H82 108.8 . . ? C9 C8 H82 112.0 . . ? C7 C8 H81 108.7 . . ? C9 C8 H81 111.0 . . ? H82 C8 H81 101.3 . . ? C5 C4 H41 106.3 . . ? C3 C4 H41 110.1 . . ? C5 C4 H42 109.9 . . ? C3 C4 H42 109.4 . . ? H41 C4 H42 107.2 . . ? C8 C7 H72 113.1 . . ? C6 C7 H72 107.3 . . ? C8 C7 H71 111.3 . . ? C6 C7 H71 109.8 . . ? H72 C7 H71 100.3 . . ? C6 C5 H51 106.8 . . ? C4 C5 H51 110.9 . . ? C6 C5 H52 111.1 . . ? C4 C5 H52 109.8 . . ? H51 C5 H52 103.7 . . ? O2 C2 H21 104.6 . . ? C3 C2 H21 111.9 . . ? O2 C2 H22 113.0 . . ? C3 C2 H22 108.3 . . ? H21 C2 H22 105.9 . . ? C8 C9 H92 107.7 . . ? C9 C9 H92 109.4 2_475 . ? C8 C9 H91 108.4 . . ? C9 C9 H91 111.6 2_475 . ? H92 C9 H91 105.4 . . ? C5 C6 H62 107.3 . . ? C7 C6 H62 110.8 . . ? C5 C6 H61 113.7 . . ? C7 C6 H61 107.3 . . ? H62 C6 H61 102.9 . . ? _diffrn_measured_fraction_theta_max 0.96 _diffrn_reflns_theta_full 24.3 _diffrn_measured_fraction_theta_full 0.96 _refine_diff_density_max 0.140 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.030