Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Xiaoming Feng' _publ_contact_author_email xmfeng@scu.edu.cn _publ_section_title ; Enantioselective aza-Micheal reaction of hydrazide to chalcones through the nonactivated amine moiety conjugated addition ; loop_ _publ_author_name 'Jun Jiang' 'Yunfei Cai' 'Weiliang Chen' 'Lili Lin' 'Xiaohua Liu' ; Xiaoming Feng ; # Attachment '- 101110_s1_jj.cif' data_101110_S1_JJ _database_code_depnum_ccdc_archive 'CCDC 801220' _audit_creation_method SHELXL-97 _chemical_absolute_configuration ad _chemical_formula_moiety 'C22 H19 Cl N2 O2' _chemical_formula_sum 'C22 H19 Cl N2 O2' _chemical_formula_weight 378.84 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ? 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' Cl Cl 0.1484 0.1585 '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 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' _cell_angle_alpha 90.00 _cell_angle_beta 105.291(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 12.6570(9) _cell_length_b 5.2425(3) _cell_length_c 14.9418(10) _cell_measurement_reflns_used 1704 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 28.9651 _cell_measurement_theta_min 3.2564 _cell_volume 956.35(11) _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.98239 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_F_000 396 _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.28 _exptl_special_details ? _diffrn_ambient_temperature 294.0 _diffrn_detector_area_resol_mean 16.0874 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -16.00 13.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -17.0486 -77.0000 -30.0000 29 #__ type_ start__ end____ width___ exp.time_ 2 omega 17.00 92.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 20.0174 38.0000 -150.0000 75 #__ type_ start__ end____ width___ exp.time_ 3 omega -53.00 52.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 20.0174 -27.0000 38.0000 105 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0134364 _diffrn_orient_matrix_UB_12 -0.0237866 _diffrn_orient_matrix_UB_13 -0.0484208 _diffrn_orient_matrix_UB_21 0.0544698 _diffrn_orient_matrix_UB_22 -0.0408583 _diffrn_orient_matrix_UB_23 0.0040331 _diffrn_orient_matrix_UB_31 -0.0150476 _diffrn_orient_matrix_UB_32 -0.1267862 _diffrn_orient_matrix_UB_33 0.0078078 _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0123 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 3884 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.26 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2489 _reflns_number_total 3162 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)' _refine_diff_density_max 0.309 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.035 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0464 _refine_ls_abs_structure_Flack 0.12(10) _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 244 _refine_ls_number_reflns 3162 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1065 _refine_ls_wR_factor_ref 0.1209 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0511P)^2^+0.1425P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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 Cl1 Cl 0.43463(7) 0.8490(3) 0.26665(6) 0.0822(4) Uani 1 1 d . . . C9 C 0.2819(2) 0.8176(6) 0.50739(18) 0.0413(7) Uani 1 1 d . . . C12 C 0.3769(2) 0.8381(8) 0.36046(19) 0.0527(8) Uani 1 1 d . . . N2 N 0.16404(19) 1.0380(5) 0.58255(16) 0.0474(6) Uani 1 1 d . . . H2 H 0.1598 1.1556 0.5416 0.057 Uiso 1 1 calc R . . N1 N 0.10963(19) 1.0468(5) 0.65332(16) 0.0469(6) Uani 1 1 d . . . H1 H 0.1307 1.1554 0.6976 0.056 Uiso 1 1 calc R . . C7 C 0.0258(2) 0.8906(7) 0.65383(19) 0.0466(7) Uani 1 1 d . . . C8 C 0.2289(2) 0.8044(6) 0.58696(17) 0.0433(7) Uani 1 1 d . . . H8 H 0.1802 0.6561 0.5786 0.052 Uiso 1 1 calc R . . C13 C 0.4040(3) 1.0181(7) 0.4287(2) 0.0592(8) Uani 1 1 d . . . H13 H 0.4539 1.1464 0.4262 0.071 Uiso 1 1 calc R . . O1 O -0.00773(18) 0.7345(5) 0.59236(16) 0.0728(8) Uani 1 1 d . . . C17 C 0.2978(2) 0.8454(6) 0.84928(18) 0.0466(7) Uani 1 1 d . . . C6 C -0.0214(2) 0.9033(6) 0.7364(2) 0.0468(7) Uani 1 1 d . . . C11 C 0.3047(3) 0.6467(7) 0.3641(2) 0.0639(9) Uani 1 1 d . . . H11 H 0.2877 0.5240 0.3176 0.077 Uiso 1 1 calc R . . C14 C 0.3559(3) 1.0065(7) 0.5018(2) 0.0564(8) Uani 1 1 d . . . H14 H 0.3739 1.1291 0.5483 0.068 Uiso 1 1 calc R . . C1 C -0.0961(3) 0.7170(7) 0.7426(2) 0.0648(9) Uani 1 1 d . . . H1A H -0.1157 0.5929 0.6967 0.078 Uiso 1 1 calc R . . C16 C 0.2670(3) 0.7029(7) 0.7598(2) 0.0524(8) Uani 1 1 d . . . C5 C 0.0067(3) 1.0853(7) 0.8043(2) 0.0654(10) Uani 1 1 d . . . H5 H 0.0572 1.2116 0.8011 0.078 Uiso 1 1 calc R . . O2 O 0.2092(2) 0.5152(5) 0.75266(15) 0.0671(7) Uani 1 1 d . . . C4 C -0.0411(3) 1.0794(9) 0.8786(3) 0.0799(12) Uani 1 1 d . . . H4 H -0.0229 1.2038 0.9245 0.096 Uiso 1 1 calc R . . C15 C 0.3129(2) 0.7858(9) 0.68016(19) 0.0685(11) Uani 1 1 d . . . H15B H 0.3476 0.9510 0.6951 0.082 Uiso 1 1 calc R . . H15A H 0.3692 0.6655 0.6748 0.082 Uiso 1 1 calc R . . C3 C -0.1145(3) 0.8923(10) 0.8845(3) 0.0753(12) Uani 1 1 d . . . H3 H -0.1453 0.8879 0.9345 0.090 Uiso 1 1 calc R . . C10 C 0.2572(3) 0.6369(7) 0.4377(2) 0.0568(9) Uani 1 1 d . . . H10 H 0.2080 0.5070 0.4401 0.068 Uiso 1 1 calc R . . C2 C -0.1418(3) 0.7147(9) 0.8170(3) 0.0817(12) Uani 1 1 d . . . H2A H -0.1922 0.5886 0.8207 0.098 Uiso 1 1 calc R . . C18 C 0.2541(3) 0.7675(7) 0.9204(2) 0.0666(10) Uani 1 1 d . . . H18 H 0.2063 0.6296 0.9112 0.080 Uiso 1 1 calc R . . C22 C 0.3682(3) 1.0503(8) 0.8666(2) 0.0686(10) Uani 1 1 d . . . H22 H 0.3996 1.1063 0.8204 0.082 Uiso 1 1 calc R . . C19 C 0.2804(3) 0.8912(9) 1.0049(2) 0.0806(12) Uani 1 1 d . . . H19 H 0.2510 0.8342 1.0521 0.097 Uiso 1 1 calc R . . C20 C 0.3483(3) 1.0939(8) 1.0197(3) 0.0790(12) Uani 1 1 d . . . H20 H 0.3644 1.1778 1.0765 0.095 Uiso 1 1 calc R . . C21 C 0.3933(3) 1.1757(8) 0.9517(3) 0.0820(12) Uani 1 1 d . . . H21 H 0.4407 1.3147 0.9620 0.098 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 Cl1 0.0751(6) 0.1280(9) 0.0563(5) -0.0035(6) 0.0398(4) -0.0055(7) C9 0.0403(14) 0.0483(17) 0.0369(13) -0.0006(14) 0.0127(11) 0.0028(15) C12 0.0453(16) 0.076(2) 0.0418(15) 0.0040(18) 0.0196(13) 0.006(2) N2 0.0593(15) 0.0450(14) 0.0461(13) 0.0048(12) 0.0287(12) 0.0056(14) N1 0.0504(14) 0.0505(15) 0.0451(13) -0.0054(12) 0.0219(11) -0.0004(14) C7 0.0387(15) 0.0583(19) 0.0419(15) -0.0055(16) 0.0093(12) 0.0029(17) C8 0.0439(15) 0.0513(18) 0.0376(14) 0.0017(13) 0.0159(12) 0.0022(16) C13 0.059(2) 0.065(2) 0.0596(19) -0.0002(19) 0.0264(17) -0.014(2) O1 0.0587(14) 0.103(2) 0.0600(14) -0.0302(15) 0.0213(11) -0.0256(15) C17 0.0474(15) 0.0509(18) 0.0432(15) 0.0069(15) 0.0149(12) 0.0090(17) C6 0.0387(14) 0.0550(18) 0.0475(16) 0.0044(15) 0.0130(13) 0.0073(16) C11 0.070(2) 0.079(2) 0.0491(18) -0.0172(18) 0.0260(17) -0.011(2) C14 0.067(2) 0.0606(19) 0.0477(17) -0.0116(16) 0.0266(16) -0.012(2) C1 0.068(2) 0.063(2) 0.069(2) 0.0073(19) 0.0285(18) 0.001(2) C16 0.0529(18) 0.065(2) 0.0406(16) 0.0113(15) 0.0136(14) 0.0174(19) C5 0.065(2) 0.077(3) 0.061(2) -0.0133(19) 0.0294(18) -0.009(2) O2 0.0936(18) 0.0541(14) 0.0536(13) 0.0005(12) 0.0193(13) -0.0024(15) C4 0.084(3) 0.101(3) 0.063(2) -0.014(2) 0.033(2) 0.006(3) C15 0.0516(17) 0.115(3) 0.0432(16) 0.015(2) 0.0203(14) 0.017(2) C3 0.075(2) 0.100(3) 0.061(2) 0.023(2) 0.0358(19) 0.017(3) C10 0.0587(19) 0.064(2) 0.0528(18) -0.0106(16) 0.0233(16) -0.0102(18) C2 0.085(3) 0.088(3) 0.084(3) 0.027(3) 0.043(2) 0.002(3) C18 0.081(2) 0.071(3) 0.057(2) -0.0047(17) 0.0360(18) -0.011(2) C22 0.079(2) 0.073(2) 0.059(2) 0.014(2) 0.0277(19) -0.007(2) C19 0.101(3) 0.095(3) 0.058(2) -0.010(2) 0.042(2) -0.015(3) C20 0.091(3) 0.087(3) 0.060(2) -0.014(2) 0.020(2) 0.007(3) C21 0.085(3) 0.072(3) 0.086(3) -0.006(2) 0.016(2) -0.016(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C12 1.744(3) . ? C9 C8 1.513(3) . ? C9 C14 1.381(4) . ? C9 C10 1.382(4) . ? C12 C13 1.365(5) . ? C12 C11 1.368(5) . ? N2 H2 0.8600 . ? N2 N1 1.407(3) . ? N2 C8 1.466(4) . ? N1 H1 0.8600 . ? N1 C7 1.342(4) . ? C7 O1 1.220(4) . ? C7 C6 1.506(4) . ? C8 H8 0.9800 . ? C8 C15 1.516(4) . ? C13 H13 0.9300 . ? C13 C14 1.384(4) . ? C17 C16 1.491(4) . ? C17 C18 1.383(4) . ? C17 C22 1.375(5) . ? C6 C1 1.380(5) . ? C6 C5 1.370(4) . ? C11 H11 0.9300 . ? C11 C10 1.385(4) . ? C14 H14 0.9300 . ? C1 H1A 0.9300 . ? C1 C2 1.383(4) . ? C16 O2 1.214(4) . ? C16 C15 1.519(4) . ? C5 H5 0.9300 . ? C5 C4 1.398(4) . ? C4 H4 0.9300 . ? C4 C3 1.370(6) . ? C15 H15B 0.9700 . ? C15 H15A 0.9700 . ? C3 H3 0.9300 . ? C3 C2 1.348(6) . ? C10 H10 0.9300 . ? C2 H2A 0.9300 . ? C18 H18 0.9300 . ? C18 C19 1.379(5) . ? C22 H22 0.9300 . ? C22 C21 1.392(5) . ? C19 H19 0.9300 . ? C19 C20 1.347(6) . ? C20 H20 0.9300 . ? C20 C21 1.358(5) . ? C21 H21 0.9300 . ? 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 C9 C8 H8 109.3 . . ? C9 C8 C15 112.1(2) . . ? C9 C14 C13 121.7(3) . . ? C9 C14 H14 119.1 . . ? C9 C10 C11 120.9(3) . . ? C9 C10 H10 119.5 . . ? C12 C13 H13 120.6 . . ? C12 C13 C14 118.9(3) . . ? C12 C11 H11 120.2 . . ? C12 C11 C10 119.5(3) . . ? N2 N1 H1 119.0 . . ? N2 C8 C9 106.6(2) . . ? N2 C8 H8 109.3 . . ? N2 C8 C15 110.1(3) . . ? N1 N2 H2 124.1 . . ? N1 N2 C8 111.9(2) . . ? N1 C7 C6 117.5(3) . . ? C7 N1 N2 121.9(2) . . ? C7 N1 H1 119.0 . . ? C8 N2 H2 124.1 . . ? C8 C15 C16 114.6(3) . . ? C8 C15 H15B 108.6 . . ? C8 C15 H15A 108.6 . . ? C13 C12 Cl1 120.1(3) . . ? C13 C12 C11 121.1(3) . . ? C13 C14 H14 119.1 . . ? O1 C7 N1 121.6(3) . . ? O1 C7 C6 120.8(3) . . ? C17 C16 C15 119.7(3) . . ? C17 C18 H18 119.5 . . ? C17 C22 H22 119.3 . . ? C17 C22 C21 121.4(3) . . ? C6 C1 H1A 120.0 . . ? C6 C1 C2 120.0(4) . . ? C6 C5 H5 120.3 . . ? C6 C5 C4 119.4(3) . . ? C11 C12 Cl1 118.8(3) . . ? C11 C10 H10 119.5 . . ? C14 C9 C8 121.9(3) . . ? C14 C9 C10 117.9(3) . . ? C14 C13 H13 120.6 . . ? C1 C6 C7 116.8(3) . . ? C1 C2 H2A 119.5 . . ? C16 C15 H15B 108.6 . . ? C16 C15 H15A 108.6 . . ? C5 C6 C7 123.8(3) . . ? C5 C6 C1 119.5(3) . . ? C5 C4 H4 119.7 . . ? O2 C16 C17 119.6(3) . . ? O2 C16 C15 120.6(3) . . ? C4 C5 H5 120.3 . . ? C4 C3 H3 120.3 . . ? C15 C8 H8 109.3 . . ? H15B C15 H15A 107.6 . . ? C3 C4 C5 120.6(4) . . ? C3 C4 H4 119.7 . . ? C3 C2 C1 121.0(4) . . ? C3 C2 H2A 119.5 . . ? C10 C9 C8 120.2(3) . . ? C10 C11 H11 120.2 . . ? C2 C1 H1A 120.0 . . ? C2 C3 C4 119.4(3) . . ? C2 C3 H3 120.3 . . ? C18 C17 C16 118.6(3) . . ? C18 C19 H19 119.6 . . ? C22 C17 C16 124.3(3) . . ? C22 C17 C18 117.1(3) . . ? C22 C21 H21 120.2 . . ? C19 C18 C17 121.0(3) . . ? C19 C18 H18 119.5 . . ? C19 C20 H20 120.0 . . ? C19 C20 C21 120.1(4) . . ? C20 C19 C18 120.7(4) . . ? C20 C19 H19 119.6 . . ? C20 C21 C22 119.6(4) . . ? C20 C21 H21 120.2 . . ? C21 C22 H22 119.3 . . ? C21 C20 H20 120.0 . . ? 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 Cl1 C12 C13 C14 179.2(3) . . . . ? Cl1 C12 C11 C10 -179.3(3) . . . . ? C9 C8 C15 C16 -164.7(3) . . . . ? C12 C13 C14 C9 0.2(5) . . . . ? C12 C11 C10 C9 -0.1(5) . . . . ? N2 N1 C7 O1 -0.5(4) . . . . ? N2 N1 C7 C6 175.8(3) . . . . ? N2 C8 C15 C16 76.8(4) . . . . ? N1 N2 C8 C9 179.5(2) . . . . ? N1 N2 C8 C15 -58.7(3) . . . . ? N1 C7 C6 C1 -170.7(3) . . . . ? N1 C7 C6 C5 8.6(4) . . . . ? C7 C6 C1 C2 179.2(3) . . . . ? C7 C6 C5 C4 -179.5(3) . . . . ? C8 C9 C14 C13 -179.9(3) . . . . ? C8 C9 C10 C11 179.8(3) . . . . ? C8 N2 N1 C7 -69.7(3) . . . . ? C13 C12 C11 C10 0.8(5) . . . . ? O1 C7 C6 C1 5.6(4) . . . . ? O1 C7 C6 C5 -175.1(3) . . . . ? C17 C16 C15 C8 -133.1(3) . . . . ? C17 C18 C19 C20 1.0(6) . . . . ? C17 C22 C21 C20 0.5(6) . . . . ? C6 C1 C2 C3 -0.1(6) . . . . ? C6 C5 C4 C3 0.8(6) . . . . ? C11 C12 C13 C14 -0.9(5) . . . . ? C14 C9 C8 N2 62.8(3) . . . . ? C14 C9 C8 C15 -57.7(4) . . . . ? C14 C9 C10 C11 -0.5(5) . . . . ? C1 C6 C5 C4 -0.2(5) . . . . ? C16 C17 C18 C19 179.5(3) . . . . ? C16 C17 C22 C21 179.8(3) . . . . ? C5 C6 C1 C2 -0.1(5) . . . . ? C5 C4 C3 C2 -1.0(6) . . . . ? O2 C16 C15 C8 50.1(5) . . . . ? C4 C3 C2 C1 0.6(6) . . . . ? C10 C9 C8 N2 -117.5(3) . . . . ? C10 C9 C8 C15 121.9(3) . . . . ? C10 C9 C14 C13 0.4(5) . . . . ? C18 C17 C16 O2 -3.7(4) . . . . ? C18 C17 C16 C15 179.4(3) . . . . ? C18 C17 C22 C21 -0.7(5) . . . . ? C18 C19 C20 C21 -1.2(6) . . . . ? C22 C17 C16 O2 175.8(3) . . . . ? C22 C17 C16 C15 -1.1(5) . . . . ? C22 C17 C18 C19 0.0(5) . . . . ? C19 C20 C21 C22 0.5(6) . . . . ? 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 H2 O1 0.86 2.42 3.013(3) 126.8 2_556 N1 H1 O2 0.86 2.19 2.972(4) 151.4 1_565