# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email liu_jinsong@gibh.ac.cn _publ_contact_author_name 'Jinsong Liu' loop_ _publ_author_name 'Jiangling Peng' 'Lanying Liu' 'Ziwei Hu' 'Jinbo Huang' 'Qiang Zhu' data_d _database_code_depnum_ccdc_archive 'CCDC 858032' #TrackingRef '8619_web_deposit_cif_file_0_JinsongLiu_1323746352.D.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 N2 O2' _chemical_formula_weight 272.34 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2365(4) _cell_length_b 9.1600(5) _cell_length_c 10.6061(5) _cell_angle_alpha 104.403(4) _cell_angle_beta 102.920(4) _cell_angle_gamma 90.218(4) _cell_volume 753.92(7) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.638 _exptl_absorpt_correction_type ? _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 1.54180 _diffrn_radiation_type CuK\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 15506 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0164 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.42 _diffrn_reflns_theta_max 67.02 _reflns_number_total 2644 _reflns_number_gt 2289 _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^)+(0.0555P)^2^+0.1160P] 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 2644 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1119 _refine_ls_wR_factor_gt 0.1067 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 N1 N 0.17109(14) 0.46772(12) 0.40123(11) 0.0529(3) Uani 1 1 d . . . N2 N 0.05937(13) 0.78882(12) 0.17448(11) 0.0490(3) Uani 1 1 d . . . O1 O 0.24188(17) 0.94704(12) 0.35483(13) 0.0881(4) Uani 1 1 d . . . O2 O 0.02932(15) 0.70727(13) -0.04999(10) 0.0727(3) Uani 1 1 d . . . C1 C 0.28258(17) 0.55340(16) 0.51405(13) 0.0525(3) Uani 1 1 d . . . C2 C 0.30580(16) 0.69793(15) 0.49564(13) 0.0509(3) Uani 1 1 d . . . C3 C 0.41665(18) 0.80468(18) 0.59497(15) 0.0630(4) Uani 1 1 d . . . H3A H 0.4362 0.9006 0.5847 0.076 Uiso 1 1 calc R . . C4 C 0.4963(2) 0.7637(2) 0.70865(16) 0.0781(5) Uani 1 1 d . . . H4A H 0.5696 0.8339 0.7761 0.094 Uiso 1 1 calc R . . C5 C 0.4699(2) 0.6200(2) 0.72537(16) 0.0794(5) Uani 1 1 d . . . H5A H 0.5252 0.5967 0.8038 0.095 Uiso 1 1 calc R . . C6 C 0.3640(2) 0.5121(2) 0.62853(15) 0.0669(4) Uani 1 1 d . . . H6A H 0.3473 0.4157 0.6389 0.080 Uiso 1 1 calc R . . C7 C 0.20208(16) 0.69705(15) 0.36624(13) 0.0495(3) Uani 1 1 d . . . C8 C 0.12504(17) 0.55319(15) 0.31419(13) 0.0511(3) Uani 1 1 d . . . H8A H 0.0518 0.5202 0.2308 0.061 Uiso 1 1 calc R . . C9 C 0.1108(2) 0.31196(17) 0.38082(17) 0.0683(4) Uani 1 1 d . . . H9A H 0.0457 0.2748 0.2909 0.102 Uiso 1 1 calc R . . H9B H 0.0427 0.3076 0.4426 0.102 Uiso 1 1 calc R . . H9C H 0.2041 0.2508 0.3956 0.102 Uiso 1 1 calc R . . C10 C 0.17593(17) 0.82088(15) 0.30501(14) 0.0549(4) Uani 1 1 d . . . C11 C 0.11900(18) 0.74055(15) 0.06250(15) 0.0558(4) Uani 1 1 d . . . C12 C 0.3059(2) 0.7325(2) 0.0822(2) 0.0794(5) Uani 1 1 d . . . H12A H 0.3329 0.6943 -0.0030 0.119 Uiso 1 1 calc R . . H12B H 0.3444 0.6663 0.1386 0.119 Uiso 1 1 calc R . . H12C H 0.3591 0.8316 0.1236 0.119 Uiso 1 1 calc R . . C13 C -0.12082(17) 0.82172(17) 0.16699(15) 0.0566(4) Uani 1 1 d . . . C14 C -0.1468(2) 0.8836(2) 0.30785(18) 0.0852(6) Uani 1 1 d . . . H14A H -0.0786 0.9755 0.3504 0.128 Uiso 1 1 calc R . . H14B H -0.1161 0.8107 0.3588 0.128 Uiso 1 1 calc R . . H14C H -0.2620 0.9036 0.3031 0.128 Uiso 1 1 calc R . . C15 C -0.2299(2) 0.6757(2) 0.0996(2) 0.0802(5) Uani 1 1 d . . . H15A H -0.2087 0.6332 0.0129 0.120 Uiso 1 1 calc R . . H15B H -0.3453 0.6971 0.0901 0.120 Uiso 1 1 calc R . . H15C H -0.2040 0.6050 0.1535 0.120 Uiso 1 1 calc R . . C16 C -0.1672(2) 0.9408(2) 0.08919(19) 0.0782(5) Uani 1 1 d . . . H16A H -0.1584 0.9012 -0.0016 0.117 Uiso 1 1 calc R . . H16B H -0.0927 1.0291 0.1300 0.117 Uiso 1 1 calc R . . H16C H -0.2797 0.9670 0.0902 0.117 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0573(7) 0.0486(6) 0.0540(6) 0.0176(5) 0.0101(5) 0.0032(5) N2 0.0481(6) 0.0494(6) 0.0492(6) 0.0166(5) 0.0064(5) 0.0014(5) O1 0.1057(9) 0.0522(7) 0.0867(8) 0.0214(6) -0.0221(7) -0.0205(6) O2 0.0868(8) 0.0749(7) 0.0516(6) 0.0123(5) 0.0108(5) 0.0030(6) C1 0.0521(7) 0.0588(8) 0.0492(7) 0.0171(6) 0.0136(6) 0.0111(6) C2 0.0468(7) 0.0560(8) 0.0474(7) 0.0107(6) 0.0086(6) 0.0076(6) C3 0.0575(8) 0.0647(9) 0.0559(8) 0.0046(7) 0.0027(7) 0.0043(7) C4 0.0673(10) 0.0940(13) 0.0551(9) 0.0028(9) -0.0041(7) 0.0091(9) C5 0.0785(11) 0.1052(15) 0.0522(9) 0.0258(9) 0.0034(8) 0.0223(10) C6 0.0697(10) 0.0812(11) 0.0562(9) 0.0294(8) 0.0145(7) 0.0177(8) C7 0.0492(7) 0.0477(7) 0.0484(7) 0.0121(6) 0.0046(6) 0.0020(5) C8 0.0532(7) 0.0491(7) 0.0489(7) 0.0143(6) 0.0058(6) 0.0020(6) C9 0.0807(11) 0.0534(9) 0.0749(10) 0.0248(7) 0.0172(8) -0.0002(7) C10 0.0555(8) 0.0478(8) 0.0556(8) 0.0129(6) 0.0017(6) -0.0031(6) C11 0.0621(8) 0.0470(7) 0.0594(9) 0.0156(6) 0.0145(7) 0.0013(6) C12 0.0648(10) 0.0823(12) 0.0972(13) 0.0222(10) 0.0320(9) 0.0086(8) C13 0.0499(8) 0.0597(8) 0.0638(9) 0.0232(7) 0.0119(6) 0.0076(6) C14 0.0832(12) 0.1030(14) 0.0811(12) 0.0296(10) 0.0361(10) 0.0285(10) C15 0.0515(9) 0.0803(12) 0.1066(14) 0.0284(10) 0.0089(9) -0.0063(8) C16 0.0731(11) 0.0785(11) 0.0919(12) 0.0418(10) 0.0148(9) 0.0226(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 N1 C8 1.3470(17) . ? N1 C1 1.3881(17) . ? N1 C9 1.4568(18) . ? N2 C11 1.3596(18) . ? N2 C10 1.4580(17) . ? N2 C13 1.5042(17) . ? O1 C10 1.2136(17) . ? O2 C11 1.2187(17) . ? C1 C6 1.390(2) . ? C1 C2 1.404(2) . ? C2 C3 1.3966(19) . ? C2 C7 1.4435(18) . ? C3 C4 1.378(2) . ? C3 H3A 0.9300 . ? C4 C5 1.394(3) . ? C4 H4A 0.9300 . ? C5 C6 1.371(2) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.3852(18) . ? C7 C10 1.435(2) . ? C8 H8A 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C11 C12 1.511(2) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.524(2) . ? C13 C16 1.525(2) . ? C13 C15 1.528(2) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 C8 N1 C1 108.78(11) . . ? C8 N1 C9 125.36(12) . . ? C1 N1 C9 125.85(12) . . ? C11 N2 C10 118.96(12) . . ? C11 N2 C13 121.74(11) . . ? C10 N2 C13 119.12(11) . . ? N1 C1 C6 129.12(14) . . ? N1 C1 C2 108.21(12) . . ? C6 C1 C2 122.67(14) . . ? C3 C2 C1 119.10(13) . . ? C3 C2 C7 134.51(14) . . ? C1 C2 C7 106.37(12) . . ? C4 C3 C2 118.07(16) . . ? C4 C3 H3A 121.0 . . ? C2 C3 H3A 121.0 . . ? C3 C4 C5 121.82(16) . . ? C3 C4 H4A 119.1 . . ? C5 C4 H4A 119.1 . . ? C6 C5 C4 121.36(15) . . ? C6 C5 H5A 119.3 . . ? C4 C5 H5A 119.3 . . ? C5 C6 C1 116.97(16) . . ? C5 C6 H6A 121.5 . . ? C1 C6 H6A 121.5 . . ? C8 C7 C10 126.18(12) . . ? C8 C7 C2 106.11(12) . . ? C10 C7 C2 127.65(12) . . ? N1 C8 C7 110.53(12) . . ? N1 C8 H8A 124.7 . . ? C7 C8 H8A 124.7 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O1 C10 C7 124.68(13) . . ? O1 C10 N2 119.43(13) . . ? C7 C10 N2 115.89(11) . . ? O2 C11 N2 122.98(14) . . ? O2 C11 C12 120.09(14) . . ? N2 C11 C12 116.92(14) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 C14 109.48(12) . . ? N2 C13 C16 109.63(12) . . ? C14 C13 C16 108.36(14) . . ? N2 C13 C15 109.16(12) . . ? C14 C13 C15 109.30(14) . . ? C16 C13 C15 110.90(14) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 C8 N1 C1 C6 -179.20(14) . . . . ? C9 N1 C1 C6 1.9(2) . . . . ? C8 N1 C1 C2 0.12(15) . . . . ? C9 N1 C1 C2 -178.76(13) . . . . ? N1 C1 C2 C3 -178.46(12) . . . . ? C6 C1 C2 C3 0.9(2) . . . . ? N1 C1 C2 C7 0.39(15) . . . . ? C6 C1 C2 C7 179.76(13) . . . . ? C1 C2 C3 C4 -1.3(2) . . . . ? C7 C2 C3 C4 -179.74(15) . . . . ? C2 C3 C4 C5 0.6(2) . . . . ? C3 C4 C5 C6 0.5(3) . . . . ? C4 C5 C6 C1 -0.9(2) . . . . ? N1 C1 C6 C5 179.42(14) . . . . ? C2 C1 C6 C5 0.2(2) . . . . ? C3 C2 C7 C8 177.85(15) . . . . ? C1 C2 C7 C8 -0.74(15) . . . . ? C3 C2 C7 C10 -5.0(3) . . . . ? C1 C2 C7 C10 176.45(14) . . . . ? C1 N1 C8 C7 -0.61(16) . . . . ? C9 N1 C8 C7 178.27(13) . . . . ? C10 C7 C8 N1 -176.40(13) . . . . ? C2 C7 C8 N1 0.84(15) . . . . ? C8 C7 C10 O1 177.84(15) . . . . ? C2 C7 C10 O1 1.2(3) . . . . ? C8 C7 C10 N2 -1.4(2) . . . . ? C2 C7 C10 N2 -178.01(12) . . . . ? C11 N2 C10 O1 89.76(18) . . . . ? C13 N2 C10 O1 -85.43(17) . . . . ? C11 N2 C10 C7 -91.00(15) . . . . ? C13 N2 C10 C7 93.81(15) . . . . ? C10 N2 C11 O2 177.84(12) . . . . ? C13 N2 C11 O2 -7.1(2) . . . . ? C10 N2 C11 C12 -3.51(19) . . . . ? C13 N2 C11 C12 171.56(13) . . . . ? C11 N2 C13 C14 -176.15(13) . . . . ? C10 N2 C13 C14 -1.10(17) . . . . ? C11 N2 C13 C16 -57.41(17) . . . . ? C10 N2 C13 C16 117.65(14) . . . . ? C11 N2 C13 C15 64.25(16) . . . . ? C10 N2 C13 C15 -120.70(14) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 67.02 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.146 _refine_diff_density_min -0.135 _refine_diff_density_rms 0.026 data_d _database_code_depnum_ccdc_archive 'CCDC 862590' #TrackingRef 'D.cif' _audit_creation_date 2012-01-13 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C14 H18 N2 O' _chemical_formula_sum 'C14 H18 N2 O' _chemical_formula_weight 230.30 _chemical_melting_point ? 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' _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 '-x, y+1/2, -z+1/2' 4 'x+1/2, -y+1/2, -z' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 'x, -y-1/2, z-1/2' 8 '-x-1/2, y-1/2, z' _cell_length_a 12.3714(4) _cell_length_b 10.1800(3) _cell_length_c 20.7350(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2611.39(13) _cell_formula_units_Z 8 _cell_measurement_reflns_used ? _cell_measurement_temperature 293(2) _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 0.588 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type ? _exptl_absorpt_process_details ? _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.172 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 992 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.11 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_unetI/netI 0.0308 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 13008 _diffrn_reflns_theta_full 66.58 _diffrn_reflns_theta_max 66.58 _diffrn_reflns_theta_min 4.26 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1709 _reflns_number_total 2299 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.139 _refine_diff_density_min -0.133 _refine_diff_density_rms 0.031 _refine_ls_extinction_coef 0.00105(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 160 _refine_ls_number_reflns 2299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0421 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+0.2394P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1086 _refine_ls_wR_factor_ref 0.1224 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.31974(10) 0.16614(11) 0.32243(6) 0.0591(4) Uani 1 1 d . . . N1 N 0.31881(11) 0.46659(13) 0.48645(6) 0.0535(4) Uani 1 1 d . . . N2 N 0.21978(12) 0.34732(13) 0.29849(7) 0.0537(4) Uani 1 1 d . . . H02 H 0.2088 0.4379 0.3108 0.078(6) Uiso 1 1 d R . . C1 C 0.45724(16) 0.3468(2) 0.55215(9) 0.0646(5) Uani 1 1 d . . . H1A H 0.4523 0.4006 0.5883 0.077 Uiso 1 1 calc R . . C2 C 0.52625(18) 0.2422(2) 0.55038(11) 0.0761(6) Uani 1 1 d . . . H2A H 0.5693 0.2241 0.5861 0.091 Uiso 1 1 calc R . . C3 C 0.53345(17) 0.1616(2) 0.49590(10) 0.0728(6) Uani 1 1 d . . . H3A H 0.5816 0.0915 0.4962 0.087 Uiso 1 1 calc R . . C4 C 0.47139(15) 0.18333(18) 0.44196(9) 0.0585(5) Uani 1 1 d . . . H4A H 0.4772 0.1290 0.4061 0.070 Uiso 1 1 calc R . . C5 C 0.32139(13) 0.34112(15) 0.39717(7) 0.0461(4) Uani 1 1 d . . . C6 C 0.27624(13) 0.44864(16) 0.42656(8) 0.0505(4) Uani 1 1 d . . . H6A H 0.2237 0.5020 0.4081 0.061 Uiso 1 1 calc R . . C7 C 0.39462(13) 0.36953(16) 0.49742(8) 0.0512(4) Uani 1 1 d . . . C8 C 0.39925(13) 0.28904(16) 0.44232(8) 0.0475(4) Uani 1 1 d . . . C9 C 0.28656(18) 0.5652(2) 0.53315(10) 0.0719(6) Uani 1 1 d . . . H9A H 0.2350 0.6237 0.5138 0.108 Uiso 1 1 calc R . . H9B H 0.3489 0.6142 0.5467 0.108 Uiso 1 1 calc R . . H9C H 0.2544 0.5231 0.5699 0.108 Uiso 1 1 calc R . . C10 C 0.28856(13) 0.27858(16) 0.33626(7) 0.0469(4) Uani 1 1 d . . . C11 C 0.16741(16) 0.29802(17) 0.23939(8) 0.0579(5) Uani 1 1 d . . . C12 C 0.1035(2) 0.1733(2) 0.25390(12) 0.0882(7) Uani 1 1 d . . . H12A H 0.0537 0.1899 0.2885 0.132 Uiso 1 1 calc R . . H12B H 0.1523 0.1045 0.2662 0.132 Uiso 1 1 calc R . . H12C H 0.0641 0.1471 0.2161 0.132 Uiso 1 1 calc R . . C13 C 0.2527(2) 0.2728(3) 0.18806(10) 0.0897(7) Uani 1 1 d . . . H13A H 0.2875 0.3540 0.1770 0.135 Uiso 1 1 calc R . . H13B H 0.2190 0.2364 0.1504 0.135 Uiso 1 1 calc R . . H13C H 0.3055 0.2122 0.2044 0.135 Uiso 1 1 calc R . . C14 C 0.0904(2) 0.4049(2) 0.21719(11) 0.0835(7) Uani 1 1 d . . . H14A H 0.1301 0.4846 0.2099 0.125 Uiso 1 1 calc R . . H14B H 0.0366 0.4196 0.2498 0.125 Uiso 1 1 calc R . . H14C H 0.0559 0.3781 0.1779 0.125 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 0.0737(8) 0.0502(7) 0.0534(7) -0.0009(5) -0.0041(6) 0.0072(6) N1 0.0588(8) 0.0534(8) 0.0483(8) -0.0043(6) -0.0033(6) 0.0014(6) N2 0.0655(9) 0.0479(7) 0.0477(8) 0.0000(6) -0.0101(6) 0.0012(6) C1 0.0663(11) 0.0738(12) 0.0537(10) 0.0004(9) -0.0108(8) -0.0024(10) C2 0.0750(13) 0.0849(14) 0.0683(13) 0.0072(10) -0.0231(10) 0.0066(11) C3 0.0667(12) 0.0684(12) 0.0833(15) 0.0055(10) -0.0160(10) 0.0141(9) C4 0.0567(10) 0.0559(10) 0.0629(11) 0.0014(8) -0.0036(8) 0.0016(8) C5 0.0471(8) 0.0476(8) 0.0437(8) 0.0035(6) 0.0009(6) -0.0036(7) C6 0.0514(9) 0.0517(9) 0.0485(9) 0.0033(7) -0.0050(7) -0.0002(7) C7 0.0520(9) 0.0536(9) 0.0481(9) 0.0039(7) -0.0034(7) -0.0046(7) C8 0.0468(8) 0.0476(8) 0.0480(9) 0.0069(7) -0.0002(7) -0.0055(7) C9 0.0796(13) 0.0725(12) 0.0637(12) -0.0174(10) -0.0040(9) 0.0069(10) C10 0.0508(9) 0.0473(9) 0.0425(8) 0.0048(7) 0.0031(7) -0.0036(7) C11 0.0721(11) 0.0528(9) 0.0488(9) 0.0002(7) -0.0133(8) -0.0004(8) C12 0.1020(17) 0.0755(13) 0.0872(16) 0.0079(12) -0.0328(13) -0.0258(12) C13 0.1144(18) 0.1055(18) 0.0492(11) 0.0016(11) -0.0021(12) 0.0204(15) C14 0.0963(16) 0.0741(13) 0.0803(15) -0.0028(11) -0.0361(12) 0.0139(12) _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 C10 1.2415(19) . ? N1 C6 1.361(2) . ? N1 C7 1.381(2) . ? N1 C9 1.451(2) . ? N2 H02 0.9665 . ? N2 C10 1.352(2) . ? N2 C11 1.474(2) . ? C1 H1A 0.9300 . ? C1 C2 1.366(3) . ? C1 C7 1.393(2) . ? C2 H2A 0.9300 . ? C2 C3 1.399(3) . ? C3 H3A 0.9300 . ? C3 C4 1.375(3) . ? C4 H4A 0.9300 . ? C4 C8 1.398(2) . ? C5 C6 1.372(2) . ? C5 C8 1.444(2) . ? C5 C10 1.472(2) . ? C6 H6A 0.9300 . ? C7 C8 1.407(2) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C11 C12 1.525(3) . ? C11 C13 1.521(3) . ? C11 C14 1.517(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C7 108.48(13) . . ? C6 N1 C9 126.53(15) . . ? C7 N1 C9 124.89(15) . . ? C10 N2 H02 115.4 . . ? C10 N2 C11 125.59(14) . . ? C11 N2 H02 118.9 . . ? C2 C1 H1A 121.5 . . ? C2 C1 C7 117.08(18) . . ? C7 C1 H1A 121.5 . . ? C1 C2 H2A 119.4 . . ? C1 C2 C3 121.25(18) . . ? C3 C2 H2A 119.4 . . ? C2 C3 H3A 119.1 . . ? C4 C3 C2 121.83(18) . . ? C4 C3 H3A 119.1 . . ? C3 C4 H4A 120.8 . . ? C3 C4 C8 118.41(17) . . ? C8 C4 H4A 120.8 . . ? C6 C5 C8 106.06(14) . . ? C6 C5 C10 127.89(15) . . ? C8 C5 C10 125.57(14) . . ? N1 C6 C5 110.78(14) . . ? N1 C6 H6A 124.6 . . ? C5 C6 H6A 124.6 . . ? N1 C7 C1 129.08(16) . . ? N1 C7 C8 108.09(14) . . ? C1 C7 C8 122.83(16) . . ? C4 C8 C5 134.82(16) . . ? C4 C8 C7 118.59(15) . . ? C7 C8 C5 106.59(14) . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O1 C10 N2 122.62(15) . . ? O1 C10 C5 120.76(14) . . ? N2 C10 C5 116.55(14) . . ? N2 C11 C12 110.31(15) . . ? N2 C11 C13 109.52(17) . . ? N2 C11 C14 106.50(14) . . ? C13 C11 C12 110.95(19) . . ? C14 C11 C12 109.33(19) . . ? C14 C11 C13 110.13(17) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 H02 O1 0.97 2.36 3.3195(18) 170.5 8_665 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 N1 C7 C8 C4 179.69(14) . . . . ? N1 C7 C8 C5 -0.57(17) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C1 C7 C8 C4 -1.4(2) . . . . ? C1 C7 C8 C5 178.39(16) . . . . ? C2 C1 C7 N1 179.57(18) . . . . ? C2 C1 C7 C8 0.9(3) . . . . ? C2 C3 C4 C8 -0.1(3) . . . . ? C3 C4 C8 C5 -178.69(18) . . . . ? C3 C4 C8 C7 1.0(2) . . . . ? C6 N1 C7 C1 -178.70(17) . . . . ? C6 N1 C7 C8 0.16(18) . . . . ? C6 C5 C8 C4 -179.57(18) . . . . ? C6 C5 C8 C7 0.75(17) . . . . ? C6 C5 C10 O1 -163.67(16) . . . . ? C6 C5 C10 N2 13.4(2) . . . . ? C7 N1 C6 C5 0.33(18) . . . . ? C7 C1 C2 C3 0.0(3) . . . . ? C8 C5 C6 N1 -0.68(18) . . . . ? C8 C5 C10 O1 7.2(2) . . . . ? C8 C5 C10 N2 -175.69(14) . . . . ? C9 N1 C6 C5 -176.17(17) . . . . ? C9 N1 C7 C1 -2.1(3) . . . . ? C9 N1 C7 C8 176.74(17) . . . . ? C10 N2 C11 C12 56.5(2) . . . . ? C10 N2 C11 C13 -65.9(2) . . . . ? C10 N2 C11 C14 175.05(18) . . . . ? C10 C5 C6 N1 171.61(15) . . . . ? C10 C5 C8 C4 7.9(3) . . . . ? C10 C5 C8 C7 -171.77(14) . . . . ? C11 N2 C10 O1 4.1(3) . . . . ? C11 N2 C10 C5 -172.91(15) . . . . ?