# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Phillip Koech' _publ_contact_author_email david.heldebrant@pnnl.gov loop_ _publ_author_name 'Phillip Koech' 'Jian Zhang' 'Igor Kutnyakov' 'Lelia Cosimbescu' 'Suh-Jane Lee' 'Mark Bowden' 'Tricia Smurthwaite' 'David Heldebrant' data_DMIPent _database_code_depnum_ccdc_archive 'CCDC 904856' #TrackingRef 'DMIPent cmpd 11a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-((1,3-dimethylimidazolidin-2-ylidene)amino)pentan-1-ol ; _chemical_name_common 1-((1,3-dimethylimidazolidin-2-ylidene)amino)pentan-1-ol _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H21 N3 O' _chemical_formula_weight 199.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 8.4702(7) _cell_length_b 11.9583(10) _cell_length_c 13.0770(10) _cell_angle_alpha 67.299(6) _cell_angle_beta 72.507(6) _cell_angle_gamma 74.577(6) _cell_volume 1148.39(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.153 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.634 _exptl_absorpt_correction_T_max 0.745 _exptl_absorpt_process_details ? _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 ? _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 10908 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0788 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.69 _reflns_number_total 5104 _reflns_number_gt 2344 _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^)+(0.0597P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.009(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5104 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1437 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1404 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _refine_ls_shift/su_max 0.033 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.3827(2) 0.88215(14) 0.34076(15) 0.0493(5) Uani 1 1 d . . . H1 H 0.671(3) 0.143(2) 0.193(3) 0.108(12) Uiso 1 1 d . . . H2 H 0.760(4) 1.262(3) -0.003(3) 0.122(12) Uiso 1 1 d . . . C1 C 0.2609(3) 0.80820(19) 0.37697(17) 0.0426(5) Uani 1 1 d . . . N2 N 0.1053(2) 0.88070(15) 0.40035(15) 0.0500(5) Uani 1 1 d . . . C2 C 0.3014(3) 1.00283(19) 0.3498(2) 0.0754(8) Uani 1 1 d . . . H2A H 0.3521 1.0677 0.2864 0.091 Uiso 1 1 calc R . . H2B H 0.3078 1.0088 0.4203 0.091 Uiso 1 1 calc R . . N3 N 0.2716(2) 0.69638(15) 0.38799(15) 0.0483(5) Uani 1 1 d . . . C3 C 0.1231(3) 1.00969(19) 0.3473(2) 0.0670(7) Uani 1 1 d . . . H3A H 0.0450 1.0594 0.3908 0.080 Uiso 1 1 calc R . . H3B H 0.1071 1.0423 0.2700 0.080 Uiso 1 1 calc R . . N4 N 1.2044(2) 0.45984(14) 0.11225(16) 0.0485(5) Uani 1 1 d . . . C4 C 0.4316(3) 0.62179(17) 0.35629(18) 0.0457(6) Uani 1 1 d . . . H4A H 0.4936 0.5954 0.4154 0.055 Uiso 1 1 calc R . . H4B H 0.4974 0.6708 0.2866 0.055 Uiso 1 1 calc R . . N5 N 0.9903(2) 0.48605(14) 0.25639(15) 0.0466(5) Uani 1 1 d . . . C5 C 0.4066(3) 0.51063(17) 0.33925(18) 0.0474(6) Uani 1 1 d . . . H5A H 0.3566 0.5378 0.2741 0.057 Uiso 1 1 calc R . . H5B H 0.3282 0.4684 0.4054 0.057 Uiso 1 1 calc R . . N6 N 1.0613(2) 0.66022(14) 0.08736(15) 0.0472(5) Uani 1 1 d . . . C6 C 0.5674(3) 0.42058(17) 0.32056(18) 0.0464(6) Uani 1 1 d . . . H6A H 0.6133 0.3893 0.3879 0.056 Uiso 1 1 calc R . . H6B H 0.6485 0.4643 0.2577 0.056 Uiso 1 1 calc R . . C7 C 0.5459(3) 0.31238(17) 0.29538(19) 0.0465(6) Uani 1 1 d . . . H7A H 0.4575 0.2729 0.3546 0.056 Uiso 1 1 calc R . . H7B H 0.5108 0.3427 0.2240 0.056 Uiso 1 1 calc R . . C8 C 0.7030(3) 0.21888(19) 0.2882(2) 0.0551(6) Uani 1 1 d . . . H8A H 0.7910 0.2583 0.2284 0.066 Uiso 1 1 calc R . . H8B H 0.7388 0.1894 0.3593 0.066 Uiso 1 1 calc R . . C9 C -0.0422(3) 0.8472(2) 0.3933(2) 0.0657(7) Uani 1 1 d . . . H9A H -0.0416 0.8653 0.3150 0.099 Uiso 1 1 calc R . . H9B H -0.1413 0.8931 0.4272 0.099 Uiso 1 1 calc R . . H9C H -0.0415 0.7608 0.4331 0.099 Uiso 1 1 calc R . . O1 O 0.6838(2) 0.11713(14) 0.26596(18) 0.0695(5) Uani 1 1 d . . . C10 C 0.5435(3) 0.8386(2) 0.3730(2) 0.0594(7) Uani 1 1 d . . . H10A H 0.6062 0.9049 0.3419 0.089 Uiso 1 1 calc R . . H10B H 0.6051 0.7731 0.3440 0.089 Uiso 1 1 calc R . . H10C H 0.5256 0.8088 0.4544 0.089 Uiso 1 1 calc R . . C11 C 1.0812(3) 0.54623(18) 0.14948(18) 0.0419(5) Uani 1 1 d . . . C12 C 1.0714(3) 0.35743(17) 0.2916(2) 0.0565(7) Uani 1 1 d . . . H12A H 0.9889 0.3033 0.3318 0.068 Uiso 1 1 calc R . . H12B H 1.1468 0.3434 0.3400 0.068 Uiso 1 1 calc R . . C13 C 1.1662(3) 0.33802(18) 0.1814(2) 0.0598(7) Uani 1 1 d . . . H13A H 1.2677 0.2775 0.1902 0.072 Uiso 1 1 calc R . . H13B H 1.0975 0.3127 0.1495 0.072 Uiso 1 1 calc R . . C14 C 0.9302(3) 0.5390(2) 0.34730(19) 0.0600(7) Uani 1 1 d . . . H14A H 1.0207 0.5673 0.3550 0.090 Uiso 1 1 calc R . . H14B H 0.8897 0.4777 0.4174 0.090 Uiso 1 1 calc R . . H14C H 0.8408 0.6070 0.3294 0.090 Uiso 1 1 calc R . . C15 C 1.2723(3) 0.4822(2) -0.0081(2) 0.0697(8) Uani 1 1 d . . . H15A H 1.1885 0.4794 -0.0423 0.105 Uiso 1 1 calc R . . H15B H 1.3684 0.4203 -0.0189 0.105 Uiso 1 1 calc R . . H15C H 1.3052 0.5618 -0.0430 0.105 Uiso 1 1 calc R . . C16 C 0.9148(3) 0.74650(17) 0.12041(18) 0.0500(6) Uani 1 1 d . . . H16A H 0.9347 0.7741 0.1754 0.060 Uiso 1 1 calc R . . H16B H 0.8177 0.7056 0.1558 0.060 Uiso 1 1 calc R . . C17 C 0.8805(3) 0.85623(17) 0.01705(18) 0.0488(6) Uani 1 1 d . . . H17A H 0.8410 0.8300 -0.0310 0.059 Uiso 1 1 calc R . . H17B H 0.9846 0.8865 -0.0263 0.059 Uiso 1 1 calc R . . C18 C 0.7511(3) 0.96017(17) 0.04805(18) 0.0473(6) Uani 1 1 d . . . H18A H 0.7881 0.9835 0.0992 0.057 Uiso 1 1 calc R . . H18B H 0.6455 0.9308 0.0882 0.057 Uiso 1 1 calc R . . C19 C 0.7219(3) 1.07323(17) -0.05494(18) 0.0508(6) Uani 1 1 d . . . H19A H 0.8292 1.0982 -0.0983 0.061 Uiso 1 1 calc R . . H19B H 0.6769 1.0509 -0.1031 0.061 Uiso 1 1 calc R . . C20 C 0.6041(3) 1.18131(19) -0.0261(2) 0.0596(7) Uani 1 1 d . . . H20A H 0.5889 1.2477 -0.0962 0.072 Uiso 1 1 calc R . . H20B H 0.4954 1.1575 0.0149 0.072 Uiso 1 1 calc R . . O2 O 0.6615(2) 1.22519(13) 0.04038(14) 0.0574(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 N1 0.0451(12) 0.0357(10) 0.0629(13) -0.0144(9) -0.0108(10) -0.0044(9) C1 0.0446(14) 0.0379(13) 0.0407(13) -0.0134(10) -0.0084(11) -0.0003(11) N2 0.0408(12) 0.0436(11) 0.0650(13) -0.0236(9) -0.0105(10) 0.0006(9) C2 0.0645(19) 0.0411(15) 0.115(2) -0.0264(14) -0.0173(17) -0.0027(12) N3 0.0441(12) 0.0398(11) 0.0576(13) -0.0200(9) -0.0072(9) -0.0003(9) C3 0.0658(19) 0.0424(14) 0.086(2) -0.0228(12) -0.0166(15) 0.0041(12) N4 0.0519(12) 0.0335(10) 0.0540(13) -0.0158(9) -0.0064(10) -0.0019(9) C4 0.0472(14) 0.0396(12) 0.0486(14) -0.0150(10) -0.0096(11) -0.0055(10) N5 0.0486(12) 0.0389(10) 0.0477(12) -0.0107(8) -0.0083(10) -0.0082(8) C5 0.0478(14) 0.0411(12) 0.0530(15) -0.0176(10) -0.0114(12) -0.0041(10) N6 0.0486(12) 0.0326(10) 0.0506(12) -0.0126(8) -0.0035(9) -0.0019(8) C6 0.0470(14) 0.0460(13) 0.0475(14) -0.0201(10) -0.0077(11) -0.0062(10) C7 0.0449(14) 0.0432(12) 0.0518(15) -0.0176(10) -0.0091(11) -0.0073(10) C8 0.0597(16) 0.0439(13) 0.0674(17) -0.0251(12) -0.0182(13) -0.0036(11) C9 0.0467(16) 0.0691(16) 0.0831(19) -0.0359(14) -0.0151(14) 0.0037(12) O1 0.0929(14) 0.0401(9) 0.0783(14) -0.0237(9) -0.0212(11) -0.0075(8) C10 0.0550(16) 0.0549(14) 0.0696(17) -0.0201(12) -0.0151(14) -0.0111(11) C11 0.0399(13) 0.0397(13) 0.0492(15) -0.0176(11) -0.0103(11) -0.0071(10) C12 0.0619(16) 0.0392(13) 0.0624(18) -0.0070(11) -0.0163(14) -0.0114(11) C13 0.0686(17) 0.0355(13) 0.0745(19) -0.0154(12) -0.0195(15) -0.0080(11) C14 0.0577(16) 0.0660(15) 0.0505(16) -0.0200(12) -0.0038(13) -0.0096(12) C15 0.081(2) 0.0539(15) 0.0612(19) -0.0248(13) -0.0004(15) 0.0013(13) C16 0.0500(14) 0.0377(12) 0.0571(16) -0.0176(11) -0.0064(12) -0.0026(10) C17 0.0488(14) 0.0408(12) 0.0569(15) -0.0214(11) -0.0113(12) -0.0005(10) C18 0.0467(14) 0.0406(12) 0.0565(15) -0.0205(11) -0.0114(12) -0.0041(10) C19 0.0574(15) 0.0439(13) 0.0550(15) -0.0194(11) -0.0198(12) -0.0020(11) C20 0.0676(18) 0.0449(14) 0.0682(17) -0.0224(12) -0.0253(14) 0.0044(12) O2 0.0656(12) 0.0479(9) 0.0618(11) -0.0262(8) -0.0046(10) -0.0137(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 N1 C1 1.392(3) . ? N1 C10 1.449(3) . ? N1 C2 1.458(3) . ? C1 N3 1.270(2) . ? C1 N2 1.392(2) . ? N2 C9 1.447(3) . ? N2 C3 1.455(3) . ? C2 C3 1.500(3) . ? N3 C4 1.452(2) . ? N4 C11 1.379(2) . ? N4 C13 1.450(2) . ? N4 C15 1.447(3) . ? C4 C5 1.506(3) . ? N5 C11 1.391(2) . ? N5 C12 1.460(2) . ? N5 C14 1.456(3) . ? C5 C6 1.515(3) . ? N6 C11 1.285(2) . ? N6 C16 1.460(2) . ? C6 C7 1.518(3) . ? C7 C8 1.498(3) . ? C8 O1 1.413(2) . ? C12 C13 1.496(3) . ? C16 C17 1.516(3) . ? C17 C18 1.519(3) . ? C18 C19 1.523(3) . ? C19 C20 1.507(3) . ? C20 O2 1.418(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C10 122.93(17) . . ? C1 N1 C2 108.82(18) . . ? C10 N1 C2 113.73(18) . . ? N3 C1 N1 131.8(2) . . ? N3 C1 N2 120.71(19) . . ? N1 C1 N2 107.48(18) . . ? C1 N2 C9 118.71(17) . . ? C1 N2 C3 108.96(18) . . ? C9 N2 C3 117.22(18) . . ? N1 C2 C3 103.18(19) . . ? C1 N3 C4 121.49(18) . . ? N2 C3 C2 101.17(17) . . ? C11 N4 C13 109.17(18) . . ? C11 N4 C15 120.28(17) . . ? C13 N4 C15 117.15(18) . . ? N3 C4 C5 111.09(17) . . ? C11 N5 C12 108.04(18) . . ? C11 N5 C14 122.47(17) . . ? C12 N5 C14 114.20(17) . . ? C4 C5 C6 113.76(17) . . ? C11 N6 C16 120.52(18) . . ? C5 C6 C7 114.32(17) . . ? C8 C7 C6 113.18(17) . . ? O1 C8 C7 113.60(18) . . ? N6 C11 N4 121.5(2) . . ? N6 C11 N5 130.3(2) . . ? N4 C11 N5 108.20(17) . . ? N5 C12 C13 103.30(17) . . ? N4 C13 C12 101.37(17) . . ? N6 C16 C17 110.21(17) . . ? C16 C17 C18 112.74(18) . . ? C17 C18 C19 113.12(18) . . ? C20 C19 C18 114.26(18) . . ? O2 C20 C19 113.52(17) . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.239 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.035 # Attachment 'DMIProp cmpd 21a.cif' data_DMIProp _database_code_depnum_ccdc_archive 'CCDC 904857' #TrackingRef 'DMIProp cmpd 21a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-((1,3-dimethylimidazolidin-2-ylidene)amino)propan-2-ol ; _chemical_name_common 1-((1,3-dimethylimidazolidin-2-ylidene)amino)propan-2-ol _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H17 N3 O' _chemical_formula_weight 171.25 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 'P 21/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 8.6849(3) _cell_length_b 13.0353(5) _cell_length_c 9.2292(4) _cell_angle_alpha 90.00 _cell_angle_beta 113.225(2) _cell_angle_gamma 90.00 _cell_volume 960.17(6) _cell_formula_units_Z 4 _cell_measurement_temperature 223 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.185 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.647 _exptl_absorpt_correction_T_max 0.745 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223 _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 6530 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 26.82 _reflns_number_total 2047 _reflns_number_gt 1420 _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2047 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0699 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1380 _refine_ls_wR_factor_gt 0.1142 _refine_ls_goodness_of_fit_ref 0.896 _refine_ls_restrained_S_all 0.896 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.002 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 0.15141(19) 0.35393(12) 0.44122(18) 0.0234(4) Uani 1 1 d . . . H1 H 0.582(2) 0.2946(12) 0.7508(19) 0.022(4) Uiso 1 1 d . . . C8 C 0.4833(3) 0.39398(16) 0.8686(2) 0.0380(5) Uani 1 1 d . . . H8 H -0.142(3) 0.2086(16) 0.460(3) 0.056(6) Uiso 1 1 d . . . H14 H 0.256(3) 0.5536(18) 0.401(3) 0.060(6) Uiso 1 1 d . . . H13 H 0.476(3) 0.2011(16) 0.953(2) 0.048(6) Uiso 1 1 d . . . H12 H -0.054(2) 0.5290(16) 0.331(2) 0.040(5) Uiso 1 1 d . . . H11 H -0.229(3) 0.3946(14) 0.336(2) 0.043(5) Uiso 1 1 d . . . H10 H 0.594(3) 0.4147(16) 0.952(3) 0.049(6) Uiso 1 1 d . . . H9 H 0.444(3) 0.4479(16) 0.787(2) 0.043(5) Uiso 1 1 d . . . H15 H 0.362(3) 0.4635(18) 0.371(3) 0.061(7) Uiso 1 1 d . . . H16 H 0.233(2) 0.5230(15) 0.227(3) 0.046(5) Uiso 1 1 d . . . H17 H -0.032(3) 0.177(2) 0.361(3) 0.079(8) Uiso 1 1 d . . . O1 O 0.55337(16) 0.21350(10) 0.91671(14) 0.0341(3) Uani 1 1 d . . . C2 C -0.0464(2) 0.46452(14) 0.2711(2) 0.0326(4) Uani 1 1 d . . . H2 H -0.175(3) 0.3246(15) 0.221(3) 0.044(5) Uiso 1 1 d . . . C3 C -0.1359(2) 0.37510(16) 0.3077(2) 0.0351(5) Uani 1 1 d . . . H3 H 0.399(3) 0.3866(15) 0.919(2) 0.044(5) Uiso 1 1 d . . . C4 C 0.2557(3) 0.49739(16) 0.3332(3) 0.0384(5) Uani 1 1 d . . . H4 H 0.244(3) 0.2701(15) 0.713(2) 0.040(5) Uiso 1 1 d . . . C5 C -0.0367(3) 0.21573(16) 0.4518(3) 0.0405(5) Uani 1 1 d . . . H5 H 0.336(3) 0.1853(15) 0.643(2) 0.040(5) Uiso 1 1 d . . . C6 C 0.3297(2) 0.26074(14) 0.6680(2) 0.0289(4) Uani 1 1 d . . . H6 H 0.044(3) 0.1825(17) 0.547(3) 0.057(6) Uiso 1 1 d . . . C7 C 0.4954(2) 0.29138(13) 0.79893(19) 0.0286(4) Uani 1 1 d . . . H7 H -0.086(2) 0.4788(14) 0.158(2) 0.035(5) Uiso 1 1 d . . . N1 N 0.29981(17) 0.32557(11) 0.53096(15) 0.0274(4) Uani 1 1 d . . . N2 N 0.12447(16) 0.42590(10) 0.32425(15) 0.0273(4) Uani 1 1 d . . . N3 N -0.00299(17) 0.32419(11) 0.44055(16) 0.0278(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 0.0229(8) 0.0244(8) 0.0230(8) -0.0038(6) 0.0092(7) -0.0015(7) C8 0.0358(11) 0.0380(11) 0.0349(10) -0.0032(9) 0.0082(9) -0.0015(9) O1 0.0238(6) 0.0451(8) 0.0327(7) 0.0120(6) 0.0106(6) 0.0085(5) C2 0.0297(9) 0.0335(10) 0.0319(10) 0.0043(8) 0.0092(8) 0.0072(8) C3 0.0226(9) 0.0464(11) 0.0344(10) 0.0051(9) 0.0091(8) 0.0036(8) C4 0.0359(11) 0.0339(11) 0.0440(12) 0.0074(9) 0.0142(9) -0.0064(9) C5 0.0295(11) 0.0406(12) 0.0446(12) 0.0068(10) 0.0073(9) -0.0107(9) C6 0.0234(9) 0.0342(10) 0.0274(9) 0.0036(7) 0.0082(7) -0.0008(7) C7 0.0223(8) 0.0342(9) 0.0278(9) 0.0052(7) 0.0083(7) 0.0026(7) N1 0.0219(7) 0.0329(8) 0.0248(7) 0.0027(6) 0.0065(6) -0.0010(6) N2 0.0221(7) 0.0278(7) 0.0289(7) 0.0035(6) 0.0067(6) -0.0005(6) N3 0.0194(7) 0.0334(8) 0.0286(7) 0.0004(6) 0.0073(6) -0.0025(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 N1 1.281(2) . ? C1 N2 1.379(2) . ? C1 N3 1.394(2) . ? C8 C7 1.506(3) . ? O1 C7 1.426(2) . ? C2 N2 1.457(2) . ? C2 C3 1.512(3) . ? C3 N3 1.470(2) . ? C4 N2 1.449(2) . ? C5 N3 1.456(2) . ? C6 N1 1.457(2) . ? C6 C7 1.523(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 N1 C1 N2 121.29(14) . . ? N1 C1 N3 130.04(15) . . ? N2 C1 N3 108.66(13) . . ? N2 C2 C3 101.75(14) . . ? N3 C3 C2 103.34(14) . . ? N1 C6 C7 109.02(13) . . ? O1 C7 C8 111.70(14) . . ? O1 C7 C6 110.93(14) . . ? C8 C7 C6 111.61(15) . . ? C1 N1 C6 121.20(13) . . ? C1 N2 C2 109.55(13) . . ? C1 N2 C4 120.39(14) . . ? C2 N2 C4 118.10(14) . . ? C1 N3 C5 119.36(14) . . ? C1 N3 C3 108.43(13) . . ? C5 N3 C3 112.59(15) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.82 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.159 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.039