Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Prof Dario Braga' _publ_contact_author_address ; Dipartimento di Chimica G. Ciamician University of Bologna via Selmi 2 Bologna 40126 ITALY ; _publ_contact_author_email DARIO.BRAGA@UNIBO.IT _publ_section_title ; Solid-state versus Solution Preparation of Two Crystals Forms of [HN(CH2CH2)3NH][OOC(CH2)COOH]2. Polymorphs or Hydrogen Bond Isomers? ; loop_ _publ_author_name 'Dario Braga' 'Lucia Maini' data_new _database_code_depnum_ccdc_archive 'CCDC 229133' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 N2 O8' _chemical_formula_weight 320.30 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 Orthorhombic _symmetry_space_group_name_H-M Pncm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x, -y+1/2, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, y, -z' '-x, y-1/2, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 8.946(2) _cell_length_b 12.144(2) _cell_length_c 6.584(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 715.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 214(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 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.865 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 214(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 1258 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 24.96 _reflns_number_total 690 _reflns_number_gt 540 _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^)+(0.1475P)^2^+0.7295P] 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 0.052(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 690 _refine_ls_number_parameters 76 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0931 _refine_ls_R_factor_gt 0.0802 _refine_ls_wR_factor_ref 0.2428 _refine_ls_wR_factor_gt 0.2285 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H100 H 0.1373 0.3396 0.0000 0.050 Uiso 1 2 d S . . H300 H 0.6024 0.3185 0.0000 0.050 Uiso 1 2 d S . . C1 C 0.6259(6) 0.1754(4) 0.0000 0.0586(14) Uani 1 2 d S . . C2 C 0.4628(5) 0.1449(4) 0.0000 0.0509(13) Uani 1 2 d S . . H2A H 0.4435 0.0997 0.1187 0.061 Uiso 0.50 1 calc PR . . H2B H 0.4435 0.0997 -0.1187 0.061 Uiso 0.50 1 calc PR . . C3 C 0.3520(5) 0.2391(4) 0.0000 0.0516(13) Uani 1 2 d S . . O1 O 0.2168(4) 0.2173(3) 0.0000 0.0612(12) Uani 1 2 d S . . O2 O 0.4004(5) 0.3360(3) 0.0000 0.0731(14) Uani 1 2 d S . . O3 O 0.6588(5) 0.2787(3) 0.0000 0.0856(16) Uani 1 2 d S . . O4 O 0.7210(4) 0.1062(4) 0.0000 0.0863(16) Uani 1 2 d S . . C9 C 0.039(2) 0.4432(12) 0.203(2) 0.053(3) Uiso 0.25 1 d P . . C8 C -0.0640(17) 0.3875(12) 0.122(3) 0.052(4) Uiso 0.25 1 d P . . C10 C 0.1668(13) 0.5071(10) -0.109(2) 0.038(3) Uiso 0.25 1 d P . . C4 C -0.0777(18) 0.3816(13) 0.0000 0.036(3) Uiso 0.25 2 d SP . . C5 C -0.0216(13) 0.4120(9) 0.1875(16) 0.0186(19) Uiso 0.25 1 d P . . C6 C 0.1174(15) 0.4831(10) 0.185(2) 0.038(3) Uiso 0.25 1 d P . . C7 C 0.1791(14) 0.5172(10) 0.0000 0.019(3) Uiso 0.25 2 d SP . . N1 N 0.0792(3) 0.4163(2) 0.0000 0.0337(10) Uani 1 2 d S . . 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 0.047(3) 0.063(3) 0.066(3) 0.000 0.000 0.006(3) C2 0.040(3) 0.049(3) 0.064(3) 0.000 0.000 0.014(2) C3 0.056(3) 0.054(3) 0.045(3) 0.000 0.000 0.026(2) O1 0.045(2) 0.068(2) 0.070(2) 0.000 0.000 0.0258(17) O2 0.080(3) 0.046(2) 0.094(3) 0.000 0.000 0.0199(19) O3 0.060(3) 0.072(3) 0.125(4) 0.000 0.000 -0.005(2) O4 0.038(2) 0.097(3) 0.125(4) 0.000 0.000 0.020(2) N1 0.0180(15) 0.0305(16) 0.053(2) 0.000 0.000 0.0051(13) _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 O4 1.196(6) . ? C1 O3 1.288(7) . ? C1 C2 1.506(7) . ? C2 C3 1.514(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O1 1.239(6) . ? C3 O2 1.253(7) . ? O3 H300 0.6991 . ? C9 C5 0.669(14) . ? C9 C6 0.860(17) . ? C9 C8 1.26(2) . ? C9 N1 1.420(15) . ? C9 C10 1.51(2) 6 ? C9 C9 1.55(3) 2_565 ? C9 C6 1.666(19) 2_565 ? C9 C5 1.769(19) 2_565 ? C9 C4 1.85(2) . ? C9 C7 2.04(2) . ? C9 C10 2.04(2) 5_565 ? C8 C5 0.649(14) . ? C8 C4 0.813(19) . ? C8 N1 1.550(14) . ? C8 C10 1.579(17) 5_565 ? C8 C8 1.60(4) 6 ? C8 C6 1.694(19) 2_565 ? C8 C7 1.744(18) 5_565 ? C10 C6 0.729(13) 6 ? C10 C7 0.734(14) . ? C10 C10 1.43(3) 6 ? C10 C9 1.51(2) 6 ? C10 N1 1.530(12) . ? C10 C8 1.579(17) 5_565 ? C10 C5 1.710(15) 5_565 ? C10 C4 1.725(18) 5_565 ? C10 C6 2.00(2) . ? C10 C9 2.04(2) 5_565 ? C4 C8 0.813(19) 6 ? C4 C5 1.383(15) . ? C4 C5 1.383(15) 6 ? C4 N1 1.466(16) . ? C4 C7 1.53(2) 5_565 ? C4 C10 1.725(18) 2_565 ? C4 C10 1.725(18) 5_565 ? C4 C9 1.85(2) 6 ? C5 C6 1.514(16) . ? C5 N1 1.529(9) . ? C5 C6 1.535(13) 2_565 ? C5 C10 1.710(15) 5_565 ? C5 C9 1.769(19) 2_565 ? C6 C10 0.729(13) 6 ? C6 C7 1.398(16) . ? C6 N1 1.501(11) . ? C6 C5 1.535(13) 2_565 ? C6 C9 1.666(19) 2_565 ? C6 C8 1.694(19) 2_565 ? C7 C10 0.734(14) 6 ? C7 C6 1.398(16) 6 ? C7 N1 1.517(13) . ? C7 C4 1.53(2) 5_565 ? C7 C8 1.744(18) 5_565 ? C7 C8 1.744(18) 2_565 ? C7 C9 2.04(2) 6 ? N1 C9 1.420(15) 6 ? N1 C6 1.501(11) 6 ? N1 C5 1.529(9) 6 ? N1 C10 1.530(12) 6 ? N1 C8 1.550(14) 6 ? N1 H100 1.0672 . ? 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 O4 C1 O3 121.5(5) . . ? O4 C1 C2 121.0(5) . . ? O3 C1 C2 117.5(5) . . ? C1 C2 C3 116.6(4) . . ? C1 C2 H2A 108.1 . . ? C3 C2 H2A 108.1 . . ? C1 C2 H2B 108.1 . . ? C3 C2 H2B 108.1 . . ? H2A C2 H2B 107.3 . . ? O1 C3 O2 122.6(4) . . ? O1 C3 C2 118.5(5) . . ? O2 C3 C2 118.9(4) . . ? C1 O3 H300 120.6 . . ? C5 C9 C6 163(3) . . ? C5 C9 C8 16.5(13) . . ? C6 C9 C8 147.0(19) . . ? C5 C9 N1 86.2(17) . . ? C6 C9 N1 78.1(13) . . ? C8 C9 N1 70.3(9) . . ? C5 C9 C10 147(2) . 6 ? C6 C9 C10 16.3(10) . 6 ? C8 C9 C10 130.7(14) . 6 ? N1 C9 C10 62.8(8) . 6 ? C5 C9 C9 98(2) . 2_565 ? C6 C9 C9 82.2(18) . 2_565 ? C8 C9 C9 98.5(17) . 2_565 ? N1 C9 C9 108.6(6) . 2_565 ? C10 C9 C9 83.3(15) 6 2_565 ? C5 C9 C6 67.1(17) . 2_565 ? C6 C9 C6 111.8(15) . 2_565 ? C8 C9 C6 69.1(13) . 2_565 ? N1 C9 C6 105.6(10) . 2_565 ? C10 C9 C6 109.2(11) 6 2_565 ? C9 C9 C6 30.8(8) 2_565 2_565 ? C5 C9 C5 118.8(18) . 2_565 ? C6 C9 C5 60.2(13) . 2_565 ? C8 C9 C5 116.3(12) . 2_565 ? N1 C9 C5 101.4(11) . 2_565 ? C10 C9 C5 62.2(11) 6 2_565 ? C9 C9 C5 22.0(7) 2_565 2_565 ? C6 C9 C5 52.2(6) 2_565 2_565 ? C5 C9 C4 37.5(13) . . ? C6 C9 C4 126.0(16) . . ? C8 C9 C4 21.0(9) . . ? N1 C9 C4 51.1(7) . . ? C10 C9 C4 109.7(10) 6 . ? C9 C9 C4 96.0(12) 2_565 . ? C6 C9 C4 72.0(11) 2_565 . ? C5 C9 C4 108.1(10) 2_565 . ? C5 C9 C7 130.5(19) . . ? C6 C9 C7 33.0(10) . . ? C8 C9 C7 114.1(11) . . ? N1 C9 C7 48.0(6) . . ? C10 C9 C7 16.8(6) 6 . ? C9 C9 C7 83.4(12) 2_565 . ? C6 C9 C7 103.4(9) 2_565 . ? C5 C9 C7 65.1(10) 2_565 . ? C4 C9 C7 93.0(8) . . ? C5 C9 C10 52.3(14) . 5_565 ? C6 C9 C10 121.8(14) . 5_565 ? C8 C9 C10 50.9(9) . 5_565 ? N1 C9 C10 90.6(9) . 5_565 ? C10 C9 C10 113.9(9) 6 5_565 ? C9 C9 C10 47.6(10) 2_565 5_565 ? C6 C9 C10 19.6(6) 2_565 5_565 ? C5 C9 C10 66.9(7) 2_565 5_565 ? C4 C9 C10 52.4(8) . 5_565 ? C7 C9 C10 103.0(7) . 5_565 ? C5 C8 C4 142(3) . . ? C5 C8 C9 17.0(13) . . ? C4 C8 C9 125(2) . . ? C5 C8 N1 76.0(15) . . ? C4 C8 N1 68.7(16) . . ? C9 C8 N1 59.6(9) . . ? C5 C8 C10 90.3(18) . 5_565 ? C4 C8 C10 86.0(18) . 5_565 ? C9 C8 C10 90.8(12) . 5_565 ? N1 C8 C10 105.7(9) . 5_565 ? C5 C8 C8 132.0(17) . 6 ? C4 C8 C8 10.1(17) . 6 ? C9 C8 C8 115.0(10) . 6 ? N1 C8 C8 58.9(7) . 6 ? C10 C8 C8 86.9(8) 5_565 6 ? C5 C8 C6 64.9(16) . 2_565 ? C4 C8 C6 106.3(19) . 2_565 ? C9 C8 C6 66.8(12) . 2_565 ? N1 C8 C6 98.6(9) . 2_565 ? C10 C8 C6 25.4(5) 5_565 2_565 ? C8 C8 C6 104.2(7) 6 2_565 ? C5 C8 C7 110.4(18) . 5_565 ? C4 C8 C7 61.2(16) . 5_565 ? C9 C8 C7 105.7(11) . 5_565 ? N1 C8 C7 95.8(8) . 5_565 ? C10 C8 C7 24.9(6) 5_565 5_565 ? C8 C8 C7 62.7(6) 6 5_565 ? C6 C8 C7 48.0(7) 2_565 5_565 ? C6 C10 C7 146(2) 6 . ? C6 C10 C10 133.5(14) 6 6 ? C7 C10 C10 13.0(14) . 6 ? C6 C10 C9 19.3(12) 6 6 ? C7 C10 C9 126.7(18) . 6 ? C10 C10 C9 114.2(8) 6 6 ? C6 C10 N1 73.9(13) 6 . ? C7 C10 N1 75.1(15) . . ? C10 C10 N1 62.1(5) 6 . ? C9 C10 N1 55.6(7) 6 . ? C6 C10 C8 86.2(16) 6 5_565 ? C7 C10 C8 90.2(16) . 5_565 ? C10 C10 C8 93.1(8) 6 5_565 ? C9 C10 C8 87.4(10) 6 5_565 ? N1 C10 C8 108.1(8) . 5_565 ? C6 C10 C5 63.9(14) 6 5_565 ? C7 C10 C5 108.3(16) . 5_565 ? C10 C10 C5 107.7(6) 6 5_565 ? C9 C10 C5 66.2(9) 6 5_565 ? N1 C10 C5 99.6(8) . 5_565 ? C8 C10 C5 22.3(5) 5_565 5_565 ? C6 C10 C4 108.5(15) 6 5_565 ? C7 C10 C4 62.2(14) . 5_565 ? C10 C10 C4 65.5(5) 6 5_565 ? C9 C10 C4 102.9(9) 6 5_565 ? N1 C10 C4 97.7(8) . 5_565 ? C8 C10 C4 28.1(7) 5_565 5_565 ? C5 C10 C4 47.5(6) 5_565 5_565 ? C6 C10 C6 118.1(17) 6 . ? C7 C10 C6 28.1(13) . . ? C10 C10 C6 15.3(4) 6 . ? C9 C10 C6 98.9(10) 6 . ? N1 C10 C6 48.1(6) . . ? C8 C10 C6 92.4(9) 5_565 . ? C5 C10 C6 102.1(8) 5_565 . ? C4 C10 C6 67.2(6) 5_565 . ? C6 C10 C9 50.2(13) 6 5_565 ? C7 C10 C9 112.5(16) . 5_565 ? C10 C10 C9 107.7(5) 6 5_565 ? C9 C10 C9 49.0(9) 6 5_565 ? N1 C10 C9 83.8(8) . 5_565 ? C8 C10 C9 38.3(7) 5_565 5_565 ? C5 C10 C9 18.0(4) 5_565 5_565 ? C4 C10 C9 58.4(7) 5_565 5_565 ? C6 C10 C9 97.9(7) . 5_565 ? C8 C4 C8 160(3) 6 . ? C8 C4 C5 143(2) 6 . ? C8 C4 C5 16.8(13) . . ? C8 C4 C5 16.8(13) 6 6 ? C8 C4 C5 143(2) . 6 ? C5 C4 C5 126.4(15) . 6 ? C8 C4 N1 80.2(17) 6 . ? C8 C4 N1 80.2(17) . . ? C5 C4 N1 64.9(7) . . ? C5 C4 N1 64.9(7) 6 . ? C8 C4 C7 91.1(16) 6 5_565 ? C8 C4 C7 91.1(16) . 5_565 ? C5 C4 C7 90.0(8) . 5_565 ? C5 C4 C7 90.0(8) 6 5_565 ? N1 C4 C7 109.7(11) . 5_565 ? C8 C4 C10 65.9(15) 6 2_565 ? C8 C4 C10 114.1(19) . 2_565 ? C5 C4 C10 109.2(10) . 2_565 ? C5 C4 C10 65.7(7) 6 2_565 ? N1 C4 C10 102.5(10) . 2_565 ? C7 C4 C10 25.1(5) 5_565 2_565 ? C8 C4 C10 114.1(19) 6 5_565 ? C8 C4 C10 65.9(15) . 5_565 ? C5 C4 C10 65.7(7) . 5_565 ? C5 C4 C10 109.2(10) 6 5_565 ? N1 C4 C10 102.5(10) . 5_565 ? C7 C4 C10 25.1(5) 5_565 5_565 ? C10 C4 C10 49.0(10) 2_565 5_565 ? C8 C4 C9 126(2) 6 . ? C8 C4 C9 33.9(14) . . ? C5 C4 C9 17.1(6) . . ? C5 C4 C9 109.3(13) 6 . ? N1 C4 C9 49.0(7) . . ? C7 C4 C9 90.6(8) 5_565 . ? C10 C4 C9 104.0(10) 2_565 . ? C10 C4 C9 69.2(8) 5_565 . ? C8 C4 C9 33.9(14) 6 6 ? C8 C4 C9 126(2) . 6 ? C5 C4 C9 109.3(13) . 6 ? C5 C4 C9 17.1(6) 6 6 ? N1 C4 C9 49.0(7) . 6 ? C7 C4 C9 90.6(8) 5_565 6 ? C10 C4 C9 69.2(8) 2_565 6 ? C10 C4 C9 104.0(10) 5_565 6 ? C9 C4 C9 92.2(13) . 6 ? C8 C5 C9 146(3) . . ? C8 C5 C4 21.2(17) . . ? C9 C5 C4 125.4(18) . . ? C8 C5 C6 137.2(18) . . ? C9 C5 C6 9.3(15) . . ? C4 C5 C6 116.1(9) . . ? C8 C5 N1 79.6(16) . . ? C9 C5 N1 67.9(15) . . ? C4 C5 N1 60.2(7) . . ? C6 C5 N1 59.1(6) . . ? C8 C5 C6 92.6(18) . 2_565 ? C9 C5 C6 89.2(17) . 2_565 ? C4 C5 C6 90.5(11) . 2_565 ? C6 C5 C6 89.1(10) . 2_565 ? N1 C5 C6 106.9(7) . 2_565 ? C8 C5 C10 67.4(16) . 5_565 ? C9 C5 C10 109.7(16) . 5_565 ? C4 C5 C10 66.8(9) . 5_565 ? C6 C5 C10 107.0(8) . 5_565 ? N1 C5 C10 100.5(7) . 5_565 ? C6 C5 C10 25.2(5) 2_565 5_565 ? C8 C5 C9 116.2(18) . 2_565 ? C9 C5 C9 60.1(18) . 2_565 ? C4 C5 C9 106.5(10) . 2_565 ? C6 C5 C9 60.4(10) . 2_565 ? N1 C5 C9 93.7(9) . 2_565 ? C6 C5 C9 29.1(5) 2_565 2_565 ? C10 C5 C9 51.6(7) 5_565 2_565 ? C10 C6 C9 144(2) 6 . ? C10 C6 C7 17.1(12) 6 . ? C9 C6 C7 127.5(15) . . ? C10 C6 N1 78.3(13) 6 . ? C9 C6 N1 67.8(12) . . ? C7 C6 N1 63.0(7) . . ? C10 C6 C5 137.2(16) 6 . ? C9 C6 C5 7.2(12) . . ? C7 C6 C5 120.2(9) . . ? N1 C6 C5 61.0(5) . . ? C10 C6 C5 90.9(16) 6 2_565 ? C9 C6 C5 90.7(15) . 2_565 ? C7 C6 C5 89.2(10) . 2_565 ? N1 C6 C5 109.3(8) . 2_565 ? C5 C6 C5 90.8(10) . 2_565 ? C10 C6 C9 110.1(16) 6 2_565 ? C9 C6 C9 67.0(16) . 2_565 ? C7 C6 C9 103.6(10) . 2_565 ? N1 C6 C9 99.0(10) . 2_565 ? C5 C6 C9 67.4(11) . 2_565 ? C5 C6 C9 23.7(5) 2_565 2_565 ? C10 C6 C8 68.4(15) 6 2_565 ? C9 C6 C8 109.1(14) . 2_565 ? C7 C6 C8 67.9(10) . 2_565 ? N1 C6 C8 103.8(8) . 2_565 ? C5 C6 C8 107.5(9) . 2_565 ? C5 C6 C8 22.5(5) 2_565 2_565 ? C9 C6 C8 44.1(7) 2_565 2_565 ? C10 C6 C10 31.2(11) 6 . ? C9 C6 C10 113.3(15) . . ? C7 C6 C10 14.3(6) . . ? N1 C6 C10 49.3(7) . . ? C5 C6 C10 106.0(8) . . ? C5 C6 C10 90.8(9) 2_565 . ? C9 C6 C10 100.2(9) 2_565 . ? C8 C6 C10 72.0(9) 2_565 . ? C10 C7 C10 154(3) . 6 ? C10 C7 C6 17.0(12) . 6 ? C10 C7 C6 137.6(19) 6 6 ? C10 C7 C6 137.6(19) . . ? C10 C7 C6 17.0(12) 6 . ? C6 C7 C6 120.9(13) 6 . ? C10 C7 N1 77.1(14) . . ? C10 C7 N1 77.1(14) 6 . ? C6 C7 N1 61.8(6) 6 . ? C6 C7 N1 61.8(6) . . ? C10 C7 C4 92.6(15) . 5_565 ? C10 C7 C4 92.6(15) 6 5_565 ? C6 C7 C4 90.2(8) 6 5_565 ? C6 C7 C4 90.2(8) . 5_565 ? N1 C7 C4 107.5(10) . 5_565 ? C10 C7 C8 64.9(14) . 5_565 ? C10 C7 C8 118.0(17) 6 5_565 ? C6 C7 C8 64.2(8) 6 5_565 ? C6 C7 C8 111.3(10) . 5_565 ? N1 C7 C8 100.8(8) . 5_565 ? C4 C7 C8 27.8(6) 5_565 5_565 ? C10 C7 C8 118.0(17) . 2_565 ? C10 C7 C8 64.9(14) 6 2_565 ? C6 C7 C8 111.3(10) 6 2_565 ? C6 C7 C8 64.2(8) . 2_565 ? N1 C7 C8 100.8(8) . 2_565 ? C4 C7 C8 27.8(6) 5_565 2_565 ? C8 C7 C8 54.7(12) 5_565 2_565 ? C10 C7 C9 36.5(13) . 6 ? C10 C7 C9 118.2(17) 6 6 ? C6 C7 C9 19.6(6) 6 6 ? C6 C7 C9 101.3(10) . 6 ? N1 C7 C9 44.1(5) . 6 ? C4 C7 C9 89.4(8) 5_565 6 ? C8 C7 C9 68.3(8) 5_565 6 ? C8 C7 C9 103.3(8) 2_565 6 ? C10 C7 C9 118.2(17) . . ? C10 C7 C9 36.5(13) 6 . ? C6 C7 C9 101.3(10) 6 . ? C6 C7 C9 19.6(6) . . ? N1 C7 C9 44.1(5) . . ? C4 C7 C9 89.4(8) 5_565 . ? C8 C7 C9 103.3(8) 5_565 . ? C8 C7 C9 68.3(8) 2_565 . ? C9 C7 C9 81.8(11) 6 . ? C9 N1 C9 140.1(11) 6 . ? C9 N1 C4 79.9(9) 6 . ? C9 N1 C4 79.9(9) . . ? C9 N1 C6 134.0(9) 6 . ? C9 N1 C6 34.1(7) . . ? C4 N1 C6 112.0(7) . . ? C9 N1 C6 34.1(7) 6 6 ? C9 N1 C6 134.0(9) . 6 ? C4 N1 C6 112.0(7) . 6 ? C6 N1 C6 108.2(11) . 6 ? C9 N1 C7 87.9(8) 6 . ? C9 N1 C7 87.9(8) . . ? C4 N1 C7 142.9(8) . . ? C6 N1 C7 55.2(6) . . ? C6 N1 C7 55.2(6) 6 . ? C9 N1 C5 25.9(6) 6 6 ? C9 N1 C5 128.2(10) . 6 ? C4 N1 C5 55.0(6) . 6 ? C6 N1 C5 143.8(6) . 6 ? C6 N1 C5 59.9(7) 6 6 ? C7 N1 C5 112.0(6) . 6 ? C9 N1 C5 128.2(10) 6 . ? C9 N1 C5 25.9(6) . . ? C4 N1 C5 55.0(6) . . ? C6 N1 C5 59.9(7) . . ? C6 N1 C5 143.8(6) 6 . ? C7 N1 C5 112.0(6) . . ? C5 N1 C5 107.7(10) 6 . ? C9 N1 C10 61.6(8) 6 . ? C9 N1 C10 113.8(11) . . ? C4 N1 C10 134.3(7) . . ? C6 N1 C10 82.7(10) . . ? C6 N1 C10 27.8(5) 6 . ? C7 N1 C10 27.9(5) . . ? C5 N1 C10 87.1(7) 6 . ? C5 N1 C10 134.7(7) . . ? C9 N1 C10 113.8(11) 6 6 ? C9 N1 C10 61.6(8) . 6 ? C4 N1 C10 134.3(7) . 6 ? C6 N1 C10 27.8(5) . 6 ? C6 N1 C10 82.7(10) 6 6 ? C7 N1 C10 27.9(5) . 6 ? C5 N1 C10 134.7(7) 6 6 ? C5 N1 C10 87.1(7) . 6 ? C10 N1 C10 55.7(11) . 6 ? C9 N1 C8 50.1(8) 6 6 ? C9 N1 C8 109.2(12) . 6 ? C4 N1 C8 31.1(7) . 6 ? C6 N1 C8 136.8(8) . 6 ? C6 N1 C8 83.8(8) 6 6 ? C7 N1 C8 132.0(7) . 6 ? C5 N1 C8 24.3(5) 6 6 ? C5 N1 C8 85.6(11) . 6 ? C10 N1 C8 110.2(8) . 6 ? C10 N1 C8 145.8(7) 6 6 ? C9 N1 C8 109.2(12) 6 . ? C9 N1 C8 50.1(8) . . ? C4 N1 C8 31.1(7) . . ? C6 N1 C8 83.8(8) . . ? C6 N1 C8 136.8(8) 6 . ? C7 N1 C8 132.0(7) . . ? C5 N1 C8 85.6(11) 6 . ? C5 N1 C8 24.3(5) . . ? C10 N1 C8 145.8(7) . . ? C10 N1 C8 110.2(8) 6 . ? C8 N1 C8 62.2(14) 6 . ? C9 N1 H100 108.9 6 . ? C9 N1 H100 108.9 . . ? C4 N1 H100 102.4 . . ? C6 N1 H100 111.1 . . ? C6 N1 H100 111.1 6 . ? C7 N1 H100 114.7 . . ? C5 N1 H100 104.9 6 . ? C5 N1 H100 104.9 . . ? C10 N1 H100 112.3 . . ? C10 N1 H100 112.3 6 . ? C8 N1 H100 101.8 6 . ? C8 N1 H100 101.8 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.417 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.082 data_lm066 _database_code_depnum_ccdc_archive 'CCDC 229134' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 N2 O8' _chemical_formula_weight 320.30 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 6.807(3) _cell_length_b 8.939(4) _cell_length_c 11.833(7) _cell_angle_alpha 94.54(4) _cell_angle_beta 90.75(4) _cell_angle_gamma 94.00(3) _cell_volume 715.9(6) _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 plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.789 _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 2631 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0104 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2499 _reflns_number_gt 2244 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0902P)^2^+0.2709P] 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 0.086(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2499 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1363 _refine_ls_wR_factor_gt 0.1310 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 -0.2581(3) 0.1699(2) 0.52874(16) 0.0388(4) Uani 1 1 d . . . C2 C -0.2466(3) 0.0362(2) 0.59898(15) 0.0373(4) Uani 1 1 d . . . H2A H -0.1300 0.0547 0.6474 0.045 Uiso 1 1 calc R . . H2B H -0.3593 0.0348 0.6483 0.045 Uiso 1 1 calc R . . C3 C -0.2403(3) -0.1186(2) 0.54073(17) 0.0427(5) Uani 1 1 d . . . O1 O -0.2753(3) 0.14093(18) 0.42209(13) 0.0616(5) Uani 1 1 d . . . O2 O -0.2523(2) 0.29685(15) 0.57522(15) 0.0577(4) Uani 1 1 d . . . O3 O -0.2502(3) -0.12767(18) 0.43030(13) 0.0626(5) Uani 1 1 d . . . O4 O -0.2277(3) -0.22737(18) 0.59326(18) 0.0752(6) Uani 1 1 d . . . C4 C 0.2144(2) 0.22159(19) 0.05302(14) 0.0313(4) Uani 1 1 d . . . C5 C 0.1604(3) 0.08863(19) 0.12206(14) 0.0341(4) Uani 1 1 d . . . H5A H 0.1719 0.1219 0.2021 0.041 Uiso 1 1 calc R . . H5B H 0.0240 0.0539 0.1058 0.041 Uiso 1 1 calc R . . C6 C 0.2872(3) -0.03998(18) 0.09814(14) 0.0325(4) Uani 1 1 d . . . O5 O 0.2779(2) 0.19065(15) -0.04641(11) 0.0427(4) Uani 1 1 d . . . O6 O 0.1896(2) 0.34871(14) 0.09283(12) 0.0473(4) Uani 1 1 d . . . O7 O 0.2300(2) -0.16057(16) 0.05474(16) 0.0606(5) Uani 1 1 d . . . O8 O 0.47146(19) -0.00453(14) 0.12981(11) 0.0386(3) Uani 1 1 d . . . C7 C 0.0901(4) 0.5079(3) 0.6728(2) 0.0597(6) Uani 1 1 d . . . H7A H 0.0806 0.4570 0.5972 0.072 Uiso 1 1 calc R . . H7B H -0.0218 0.5688 0.6832 0.072 Uiso 1 1 calc R . . C8 C 0.0886(3) 0.3939(2) 0.75988(15) 0.0369(4) Uani 1 1 d . . . H8A H -0.0241 0.4046 0.8084 0.044 Uiso 1 1 calc R . . H8B H 0.0786 0.2931 0.7225 0.044 Uiso 1 1 calc R . . C9 C 0.4445(4) 0.5117(3) 0.6672(2) 0.0666(7) Uani 1 1 d . . . H9A H 0.5661 0.5754 0.6717 0.080 Uiso 1 1 calc R . . H9B H 0.4338 0.4588 0.5924 0.080 Uiso 1 1 calc R . . C10 C 0.4470(3) 0.4005(2) 0.75589(15) 0.0384(4) Uani 1 1 d . . . H10A H 0.4427 0.2990 0.7199 0.046 Uiso 1 1 calc R . . H10B H 0.5671 0.4182 0.8014 0.046 Uiso 1 1 calc R . . C11 C 0.2867(4) 0.6840(2) 0.80065(18) 0.0523(6) Uani 1 1 d . . . H11A H 0.1752 0.7451 0.8114 0.063 Uiso 1 1 calc R . . H11B H 0.4063 0.7498 0.8089 0.063 Uiso 1 1 calc R . . C12 C 0.2856(3) 0.5709(2) 0.88795(15) 0.0395(4) Uani 1 1 d . . . H12A H 0.4050 0.5866 0.9343 0.047 Uiso 1 1 calc R . . H12B H 0.1737 0.5822 0.9370 0.047 Uiso 1 1 calc R . . N1 N 0.2754(2) 0.60446(17) 0.68607(13) 0.0374(4) Uani 1 1 d . . . N2 N 0.2733(2) 0.41819(15) 0.82893(11) 0.0285(3) Uani 1 1 d . . . H200 H 0.277(4) 0.349(3) 0.881(2) 0.059(7) Uiso 1 1 d . . . H100 H 0.279(3) 0.674(3) 0.639(2) 0.054(6) Uiso 1 1 d . . . H800 H 0.552(4) -0.075(3) 0.099(2) 0.063(7) Uiso 1 1 d . . . H300 H -0.252(4) 0.004(4) 0.407(3) 0.088(9) 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 0.0333(9) 0.0387(10) 0.0450(10) 0.0098(8) 0.0014(7) -0.0004(7) C2 0.0452(10) 0.0347(9) 0.0322(9) 0.0052(7) 0.0002(7) 0.0007(7) C3 0.0427(10) 0.0353(10) 0.0498(11) 0.0035(8) 0.0032(8) 0.0014(8) O1 0.0892(12) 0.0562(10) 0.0404(8) 0.0194(7) -0.0049(7) -0.0032(8) O2 0.0589(9) 0.0315(8) 0.0825(11) 0.0020(7) 0.0055(8) 0.0044(6) O3 0.0867(12) 0.0500(9) 0.0480(9) -0.0140(7) 0.0057(8) 0.0026(8) O4 0.1005(14) 0.0374(9) 0.0908(13) 0.0196(8) -0.0030(10) 0.0100(8) C4 0.0295(8) 0.0327(9) 0.0327(9) 0.0052(7) 0.0009(6) 0.0067(6) C5 0.0388(9) 0.0339(9) 0.0306(8) 0.0051(7) 0.0068(7) 0.0064(7) C6 0.0419(9) 0.0287(9) 0.0274(8) 0.0036(6) 0.0049(6) 0.0032(7) O5 0.0538(8) 0.0431(7) 0.0360(7) 0.0151(5) 0.0145(6) 0.0213(6) O6 0.0622(9) 0.0302(7) 0.0500(8) 0.0011(6) 0.0087(6) 0.0077(6) O7 0.0553(9) 0.0353(8) 0.0870(12) -0.0181(7) -0.0011(8) 0.0005(6) O8 0.0397(7) 0.0345(7) 0.0411(7) -0.0046(5) -0.0002(5) 0.0086(5) C7 0.0650(14) 0.0505(12) 0.0630(14) 0.0216(10) -0.0331(11) -0.0130(10) C8 0.0341(9) 0.0347(9) 0.0409(10) 0.0035(7) -0.0015(7) -0.0042(7) C9 0.0742(16) 0.0620(14) 0.0716(15) 0.0308(12) 0.0438(13) 0.0251(12) C10 0.0368(9) 0.0398(10) 0.0398(9) 0.0027(8) 0.0101(7) 0.0107(7) C11 0.0824(15) 0.0264(9) 0.0468(11) -0.0047(8) -0.0073(10) 0.0043(9) C12 0.0541(11) 0.0341(9) 0.0290(8) -0.0067(7) -0.0008(7) 0.0049(8) N1 0.0501(9) 0.0296(7) 0.0336(8) 0.0103(6) 0.0024(6) 0.0013(6) N2 0.0352(7) 0.0264(7) 0.0244(7) 0.0022(5) 0.0028(5) 0.0046(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 O2 1.219(2) . ? C1 O1 1.270(3) . ? C1 C2 1.514(3) . ? C2 C3 1.500(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O4 1.202(3) . ? C3 O3 1.303(3) . ? O1 H300 1.24(3) . ? O3 H300 1.23(3) . ? C4 O6 1.219(2) . ? C4 O5 1.275(2) . ? C4 C5 1.522(2) . ? C5 C6 1.497(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O7 1.194(2) . ? C6 O8 1.314(2) . ? O8 H800 0.92(3) . ? C7 N1 1.477(3) . ? C7 C8 1.505(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N2 1.484(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N1 1.474(3) . ? C9 C10 1.502(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N2 1.483(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N1 1.479(3) . ? C11 C12 1.501(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N2 1.480(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? N1 H100 0.87(3) . ? N2 H200 0.91(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 O2 C1 O1 123.56(18) . . ? O2 C1 C2 119.98(18) . . ? O1 C1 C2 116.45(17) . . ? C3 C2 C1 119.58(16) . . ? C3 C2 H2A 107.4 . . ? C1 C2 H2A 107.4 . . ? C3 C2 H2B 107.4 . . ? C1 C2 H2B 107.4 . . ? H2A C2 H2B 107.0 . . ? O4 C3 O3 122.3(2) . . ? O4 C3 C2 121.7(2) . . ? O3 C3 C2 115.96(17) . . ? C1 O1 H300 104.5(15) . . ? C3 O3 H300 104.2(15) . . ? O6 C4 O5 123.95(16) . . ? O6 C4 C5 119.51(15) . . ? O5 C4 C5 116.49(15) . . ? C6 C5 C4 113.20(14) . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5B 108.9 . . ? C4 C5 H5B 108.9 . . ? H5A C5 H5B 107.8 . . ? O7 C6 O8 123.41(17) . . ? O7 C6 C5 124.64(17) . . ? O8 C6 C5 111.95(15) . . ? C6 O8 H800 110.8(16) . . ? N1 C7 C8 108.74(16) . . ? N1 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? N1 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? N2 C8 C7 109.07(15) . . ? N2 C8 H8A 109.9 . . ? C7 C8 H8A 109.9 . . ? N2 C8 H8B 109.9 . . ? C7 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? N1 C9 C10 109.13(16) . . ? N1 C9 H9A 109.9 . . ? C10 C9 H9A 109.9 . . ? N1 C9 H9B 109.9 . . ? C10 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? N2 C10 C9 108.84(15) . . ? N2 C10 H10A 109.9 . . ? C9 C10 H10A 109.9 . . ? N2 C10 H10B 109.9 . . ? C9 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? N1 C11 C12 109.39(15) . . ? N1 C11 H11A 109.8 . . ? C12 C11 H11A 109.8 . . ? N1 C11 H11B 109.8 . . ? C12 C11 H11B 109.8 . . ? H11A C11 H11B 108.2 . . ? N2 C12 C11 108.61(14) . . ? N2 C12 H12A 110.0 . . ? C11 C12 H12A 110.0 . . ? N2 C12 H12B 110.0 . . ? C11 C12 H12B 110.0 . . ? H12A C12 H12B 108.3 . . ? C9 N1 C7 109.62(19) . . ? C9 N1 C11 110.83(19) . . ? C7 N1 C11 109.59(18) . . ? C9 N1 H100 109.5(16) . . ? C7 N1 H100 111.4(16) . . ? C11 N1 H100 105.8(17) . . ? C12 N2 C10 109.67(14) . . ? C12 N2 C8 109.66(14) . . ? C10 N2 C8 110.43(14) . . ? C12 N2 H200 109.0(16) . . ? C10 N2 H200 107.4(16) . . ? C8 N2 H200 110.7(16) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.314 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.056