# Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Ying-Chun Chen' _publ_contact_author_email YCCHENHUAXI@YAHOO.COM.CN _publ_section_title ; Tributyltin Hydride-Mediated Radical Cyclisation Reactions: Efficient Construction of Multiply Substituted Cyclopentanes ; loop_ _publ_author_name 'Ying-Chun Chen' 'Hai-Lei Cui' 'Zheng-Yu Ding' 'Jie Lei' 'Rui Li' 'Li Wu' # Attachment 'racemic_2a.cif' data_2a _database_code_depnum_ccdc_archive 'CCDC 763227' #TrackingRef 'racemic_2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 N2 O' _chemical_formula_weight 354.44 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 P2(1)/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 11.932(3) _cell_length_b 11.410(2) _cell_length_c 14.195(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.394(2) _cell_angle_gamma 90.00 _cell_volume 1872.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 5689 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.50 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.43 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9673 _exptl_absorpt_correction_T_max 0.9673 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku SPIDER' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14779 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4285 _reflns_number_gt 3675 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto Version 3.0 (Rigaku 2004)' _computing_cell_refinement 'Rapid Auto Version 3.0 (Rigaku 2004)' _computing_data_reduction 'Rapid Auto Version 3.0 (Rigaku 2004)' _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^)+(0.0560P)^2^+0.6690P] 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 4285 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1092 _refine_ls_wR_factor_gt 0.1019 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.98824(8) 0.45903(9) 0.17078(8) 0.0286(2) Uani 1 1 d . . . N1 N 0.75068(10) 0.45903(10) 0.09778(8) 0.0186(2) Uani 1 1 d . . . N2 N 0.46947(9) 0.64347(10) 0.02731(8) 0.0212(2) Uani 1 1 d . . . C1 C 0.66517(11) 0.92603(11) 0.08976(9) 0.0181(3) Uani 1 1 d . . . H1 H 0.6856 0.8840 0.0387 0.022 Uiso 1 1 calc R . . C2 C 0.62193(11) 1.03889(12) 0.07243(10) 0.0208(3) Uani 1 1 d . . . H2 H 0.6147 1.0743 0.0107 0.025 Uiso 1 1 calc R . . C3 C 0.58930(11) 1.09971(12) 0.14608(10) 0.0213(3) Uani 1 1 d . . . H3 H 0.5588 1.1768 0.1348 0.026 Uiso 1 1 calc R . . C4 C 0.60144(11) 1.04727(11) 0.23608(10) 0.0197(3) Uani 1 1 d . . . H4 H 0.5780 1.0889 0.2859 0.024 Uiso 1 1 calc R . . C5 C 0.64735(11) 0.93456(11) 0.25541(9) 0.0169(3) Uani 1 1 d . . . C6 C 0.66491(12) 0.88350(11) 0.35657(9) 0.0213(3) Uani 1 1 d . . . H6A H 0.5929 0.8440 0.3620 0.026 Uiso 1 1 calc R . . H6B H 0.6812 0.9477 0.4050 0.026 Uiso 1 1 calc R . . C7 C 0.76448(12) 0.79580(11) 0.37928(9) 0.0189(3) Uani 1 1 d . . . H7A H 0.7712 0.7606 0.4442 0.023 Uiso 1 1 calc R . . H7B H 0.8382 0.8360 0.3799 0.023 Uiso 1 1 calc R . . C8 C 0.74090(11) 0.70029(10) 0.30157(9) 0.0151(2) Uani 1 1 d . . . H8 H 0.6662 0.6606 0.3016 0.018 Uiso 1 1 calc R . . C9 C 0.73303(10) 0.75244(10) 0.19825(8) 0.0140(2) Uani 1 1 d . . . C10 C 0.67935(10) 0.87269(11) 0.18069(9) 0.0151(3) Uani 1 1 d . . . C11 C 0.68093(10) 0.65517(11) 0.12605(8) 0.0147(3) Uani 1 1 d . . . C12 C 0.76117(11) 0.56704(11) 0.13604(8) 0.0149(2) Uani 1 1 d . . . C13 C 0.86904(10) 0.60971(11) 0.21021(9) 0.0152(3) Uani 1 1 d . . . C14 C 0.83801(11) 0.60612(11) 0.31337(9) 0.0158(3) Uani 1 1 d . . . H14 H 0.9069 0.6367 0.3626 0.019 Uiso 1 1 calc R . . C15 C 0.86038(10) 0.74330(11) 0.19265(9) 0.0153(3) Uani 1 1 d . . . H15A H 0.8712 0.7658 0.1282 0.018 Uiso 1 1 calc R . . H15B H 0.9139 0.7883 0.2446 0.018 Uiso 1 1 calc R . . C16 C 0.81299(11) 0.48484(11) 0.34616(9) 0.0169(3) Uani 1 1 d . . . C17 C 0.90342(12) 0.41830(12) 0.40254(9) 0.0214(3) Uani 1 1 d . . . H17 H 0.9794 0.4499 0.4197 0.026 Uiso 1 1 calc R . . C18 C 0.88374(13) 0.30622(12) 0.43403(10) 0.0259(3) Uani 1 1 d . . . H18 H 0.9461 0.2621 0.4725 0.031 Uiso 1 1 calc R . . C19 C 0.77342(13) 0.25913(12) 0.40929(10) 0.0259(3) Uani 1 1 d . . . H19 H 0.7597 0.1829 0.4310 0.031 Uiso 1 1 calc R . . C20 C 0.68295(12) 0.32382(12) 0.35268(10) 0.0233(3) Uani 1 1 d . . . H20 H 0.6072 0.2915 0.3355 0.028 Uiso 1 1 calc R . . C21 C 0.70231(11) 0.43539(11) 0.32100(10) 0.0197(3) Uani 1 1 d . . . H21 H 0.6398 0.4786 0.2818 0.024 Uiso 1 1 calc R . . C22 C 0.56468(11) 0.64842(11) 0.07250(9) 0.0155(3) Uani 1 1 d . . . C23 C 0.98325(11) 0.55168(11) 0.21258(9) 0.0186(3) Uani 1 1 d . . . C24 C 1.09168(11) 0.61122(13) 0.26964(11) 0.0248(3) Uani 1 1 d . . . H24A H 1.1589 0.5622 0.2691 0.030 Uiso 1 1 calc R . . H24B H 1.0867 0.6229 0.3369 0.030 Uiso 1 1 calc R . . H24C H 1.0999 0.6873 0.2401 0.030 Uiso 1 1 calc R . . H1A H 0.8167(17) 0.4150(16) 0.1128(13) 0.037(5) Uiso 1 1 d . . . H1B H 0.6813(16) 0.4328(15) 0.0611(13) 0.034(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0218(5) 0.0262(5) 0.0359(6) -0.0045(4) 0.0036(4) 0.0078(4) N1 0.0175(5) 0.0166(5) 0.0201(6) -0.0036(4) 0.0016(4) 0.0022(4) N2 0.0180(6) 0.0209(6) 0.0233(6) -0.0051(4) 0.0023(5) 0.0009(4) C1 0.0168(6) 0.0198(6) 0.0169(6) -0.0020(5) 0.0027(5) 0.0000(5) C2 0.0184(6) 0.0208(7) 0.0215(6) 0.0030(5) 0.0013(5) 0.0005(5) C3 0.0171(6) 0.0156(6) 0.0295(7) -0.0006(5) 0.0025(5) 0.0021(5) C4 0.0164(6) 0.0178(6) 0.0259(7) -0.0061(5) 0.0070(5) -0.0019(5) C5 0.0150(6) 0.0163(6) 0.0196(6) -0.0030(5) 0.0049(5) -0.0036(5) C6 0.0291(7) 0.0175(6) 0.0200(6) -0.0042(5) 0.0113(5) -0.0026(5) C7 0.0265(7) 0.0165(6) 0.0140(6) -0.0012(5) 0.0055(5) -0.0033(5) C8 0.0169(6) 0.0138(6) 0.0147(6) -0.0010(4) 0.0044(5) -0.0028(5) C9 0.0143(6) 0.0133(6) 0.0137(6) -0.0015(4) 0.0025(4) -0.0017(4) C10 0.0130(6) 0.0143(6) 0.0176(6) -0.0018(4) 0.0031(5) -0.0021(4) C11 0.0144(6) 0.0155(6) 0.0142(6) -0.0020(4) 0.0032(5) -0.0007(5) C12 0.0154(6) 0.0172(6) 0.0122(5) 0.0000(4) 0.0039(5) -0.0002(5) C13 0.0138(6) 0.0159(6) 0.0154(6) 0.0004(4) 0.0025(5) -0.0006(5) C14 0.0163(6) 0.0162(6) 0.0139(6) 0.0001(4) 0.0015(5) -0.0028(5) C15 0.0145(6) 0.0158(6) 0.0152(6) 0.0006(4) 0.0026(5) -0.0003(5) C16 0.0217(6) 0.0153(6) 0.0144(6) -0.0009(4) 0.0056(5) -0.0016(5) C17 0.0231(7) 0.0207(6) 0.0187(6) 0.0008(5) 0.0022(5) -0.0012(5) C18 0.0341(8) 0.0213(7) 0.0207(7) 0.0040(5) 0.0039(6) 0.0034(6) C19 0.0393(8) 0.0167(6) 0.0245(7) 0.0022(5) 0.0135(6) -0.0022(6) C20 0.0261(7) 0.0186(6) 0.0280(7) -0.0025(5) 0.0118(6) -0.0054(5) C21 0.0206(6) 0.0178(6) 0.0214(6) -0.0006(5) 0.0068(5) -0.0011(5) C22 0.0184(6) 0.0139(6) 0.0150(6) -0.0026(4) 0.0060(5) 0.0006(5) C23 0.0166(6) 0.0201(6) 0.0189(6) 0.0053(5) 0.0037(5) 0.0023(5) C24 0.0147(6) 0.0279(7) 0.0302(7) 0.0029(6) 0.0026(5) 0.0013(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 O1 C23 1.2210(16) . ? N1 C12 1.3400(16) . ? N1 H1A 0.914(19) . ? N1 H1B 0.912(19) . ? N2 C22 1.1588(17) . ? C1 C2 1.3864(18) . ? C1 C10 1.3988(18) . ? C1 H1 0.9500 . ? C2 C3 1.3887(19) . ? C2 H2 0.9500 . ? C3 C4 1.3853(19) . ? C3 H3 0.9500 . ? C4 C5 1.3981(18) . ? C4 H4 0.9500 . ? C5 C10 1.4037(17) . ? C5 C6 1.5152(18) . ? C6 C7 1.5253(19) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5262(17) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C14 1.5585(17) . ? C8 C9 1.5637(16) . ? C8 H8 1.0000 . ? C9 C10 1.5086(17) . ? C9 C11 1.5337(16) . ? C9 C15 1.5447(17) . ? C11 C12 1.3713(17) . ? C11 C22 1.4085(17) . ? C12 C13 1.5259(16) . ? C13 C23 1.5079(17) . ? C13 C15 1.5439(17) . ? C13 C14 1.5978(17) . ? C14 C16 1.5133(17) . ? C14 H14 1.0000 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.3970(18) . ? C16 C21 1.3984(18) . ? C17 C18 1.3938(19) . ? C17 H17 0.9500 . ? C18 C19 1.384(2) . ? C18 H18 0.9500 . ? C19 C20 1.387(2) . ? C19 H19 0.9500 . ? C20 C21 1.3885(18) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C23 C24 1.5068(18) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 C12 N1 H1A 115.0(11) . . ? C12 N1 H1B 120.9(11) . . ? H1A N1 H1B 124.1(16) . . ? C2 C1 C10 121.48(12) . . ? C2 C1 H1 119.3 . . ? C10 C1 H1 119.3 . . ? C1 C2 C3 119.49(12) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 119.59(12) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 121.63(12) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C4 C5 C10 118.77(12) . . ? C4 C5 C6 119.66(11) . . ? C10 C5 C6 121.55(11) . . ? C5 C6 C7 111.68(11) . . ? C5 C6 H6A 109.3 . . ? C7 C6 H6A 109.3 . . ? C5 C6 H6B 109.3 . . ? C7 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? C6 C7 C8 108.77(10) . . ? C6 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? C6 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C7 C8 C14 114.59(10) . . ? C7 C8 C9 111.31(10) . . ? C14 C8 C9 103.47(9) . . ? C7 C8 H8 109.1 . . ? C14 C8 H8 109.1 . . ? C9 C8 H8 109.1 . . ? C10 C9 C11 117.58(10) . . ? C10 C9 C15 115.83(10) . . ? C11 C9 C15 99.04(9) . . ? C10 C9 C8 115.16(10) . . ? C11 C9 C8 105.74(9) . . ? C15 C9 C8 101.08(9) . . ? C1 C10 C5 119.03(11) . . ? C1 C10 C9 119.81(11) . . ? C5 C10 C9 121.11(11) . . ? C12 C11 C22 125.76(11) . . ? C12 C11 C9 107.76(10) . . ? C22 C11 C9 125.55(11) . . ? N1 C12 C11 129.79(12) . . ? N1 C12 C13 123.43(11) . . ? C11 C12 C13 106.55(10) . . ? C23 C13 C12 118.55(11) . . ? C23 C13 C15 117.45(10) . . ? C12 C13 C15 101.10(9) . . ? C23 C13 C14 112.48(10) . . ? C12 C13 C14 106.03(9) . . ? C15 C13 C14 98.73(9) . . ? C16 C14 C8 117.73(10) . . ? C16 C14 C13 114.44(10) . . ? C8 C14 C13 102.67(9) . . ? C16 C14 H14 107.1 . . ? C8 C14 H14 107.1 . . ? C13 C14 H14 107.1 . . ? C13 C15 C9 94.91(9) . . ? C13 C15 H15A 112.8 . . ? C9 C15 H15A 112.8 . . ? C13 C15 H15B 112.8 . . ? C9 C15 H15B 112.8 . . ? H15A C15 H15B 110.2 . . ? C17 C16 C21 118.22(12) . . ? C17 C16 C14 119.33(11) . . ? C21 C16 C14 122.44(11) . . ? C18 C17 C16 120.97(13) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C19 C18 C17 120.02(13) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 119.64(13) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C19 C20 C21 120.48(13) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C20 C21 C16 120.65(12) . . ? C20 C21 H21 119.7 . . ? C16 C21 H21 119.7 . . ? N2 C22 C11 179.04(14) . . ? O1 C23 C24 120.83(12) . . ? O1 C23 C13 121.48(12) . . ? C24 C23 C13 117.68(11) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 C10 C1 C2 C3 -1.53(19) . . . . ? C1 C2 C3 C4 0.63(19) . . . . ? C2 C3 C4 C5 0.84(19) . . . . ? C3 C4 C5 C10 -1.40(19) . . . . ? C3 C4 C5 C6 176.72(12) . . . . ? C4 C5 C6 C7 -151.37(11) . . . . ? C10 C5 C6 C7 26.70(17) . . . . ? C5 C6 C7 C8 -56.43(14) . . . . ? C6 C7 C8 C14 178.03(10) . . . . ? C6 C7 C8 C9 61.06(13) . . . . ? C7 C8 C9 C10 -35.07(14) . . . . ? C14 C8 C9 C10 -158.62(10) . . . . ? C7 C8 C9 C11 -166.65(10) . . . . ? C14 C8 C9 C11 69.80(11) . . . . ? C7 C8 C9 C15 90.55(11) . . . . ? C14 C8 C9 C15 -33.00(11) . . . . ? C2 C1 C10 C5 0.96(19) . . . . ? C2 C1 C10 C9 -176.51(11) . . . . ? C4 C5 C10 C1 0.50(18) . . . . ? C6 C5 C10 C1 -177.58(11) . . . . ? C4 C5 C10 C9 177.93(11) . . . . ? C6 C5 C10 C9 -0.15(18) . . . . ? C11 C9 C10 C1 -52.52(16) . . . . ? C15 C9 C10 C1 64.21(15) . . . . ? C8 C9 C10 C1 -178.21(11) . . . . ? C11 C9 C10 C5 130.07(12) . . . . ? C15 C9 C10 C5 -113.20(13) . . . . ? C8 C9 C10 C5 4.38(16) . . . . ? C10 C9 C11 C12 161.33(11) . . . . ? C15 C9 C11 C12 35.83(12) . . . . ? C8 C9 C11 C12 -68.47(12) . . . . ? C10 C9 C11 C22 -29.22(17) . . . . ? C15 C9 C11 C22 -154.73(12) . . . . ? C8 C9 C11 C22 100.97(13) . . . . ? C22 C11 C12 N1 1.6(2) . . . . ? C9 C11 C12 N1 171.01(12) . . . . ? C22 C11 C12 C13 -172.97(11) . . . . ? C9 C11 C12 C13 -3.55(13) . . . . ? N1 C12 C13 C23 24.85(17) . . . . ? C11 C12 C13 C23 -160.16(11) . . . . ? N1 C12 C13 C15 154.76(12) . . . . ? C11 C12 C13 C15 -30.24(12) . . . . ? N1 C12 C13 C14 -102.69(13) . . . . ? C11 C12 C13 C14 72.31(12) . . . . ? C7 C8 C14 C16 108.25(12) . . . . ? C9 C8 C14 C16 -130.38(11) . . . . ? C7 C8 C14 C13 -125.08(11) . . . . ? C9 C8 C14 C13 -3.71(11) . . . . ? C23 C13 C14 C16 -67.62(13) . . . . ? C12 C13 C14 C16 63.46(13) . . . . ? C15 C13 C14 C16 167.75(10) . . . . ? C23 C13 C14 C8 163.62(10) . . . . ? C12 C13 C14 C8 -65.30(11) . . . . ? C15 C13 C14 C8 38.99(11) . . . . ? C23 C13 C15 C9 -179.61(10) . . . . ? C12 C13 C15 C9 49.79(10) . . . . ? C14 C13 C15 C9 -58.57(10) . . . . ? C10 C9 C15 C13 -177.63(10) . . . . ? C11 C9 C15 C13 -50.91(10) . . . . ? C8 C9 C15 C13 57.20(10) . . . . ? C8 C14 C16 C17 -148.23(12) . . . . ? C13 C14 C16 C17 91.04(14) . . . . ? C8 C14 C16 C21 32.70(17) . . . . ? C13 C14 C16 C21 -88.03(14) . . . . ? C21 C16 C17 C18 -0.84(19) . . . . ? C14 C16 C17 C18 -179.95(12) . . . . ? C16 C17 C18 C19 0.2(2) . . . . ? C17 C18 C19 C20 0.3(2) . . . . ? C18 C19 C20 C21 -0.2(2) . . . . ? C19 C20 C21 C16 -0.5(2) . . . . ? C17 C16 C21 C20 0.99(19) . . . . ? C14 C16 C21 C20 -179.93(12) . . . . ? C12 C11 C22 N2 -92(8) . . . . ? C9 C11 C22 N2 101(8) . . . . ? C12 C13 C23 O1 -14.09(18) . . . . ? C15 C13 C23 O1 -136.07(13) . . . . ? C14 C13 C23 O1 110.34(14) . . . . ? C12 C13 C23 C24 166.70(11) . . . . ? C15 C13 C23 C24 44.72(16) . . . . ? C14 C13 C23 C24 -68.86(14) . . . . ? 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 N1 H1A O1 0.914(19) 2.069(19) 2.7655(16) 132.1(15) . N1 H1B N2 0.912(19) 2.109(19) 3.0170(16) 173.9(16) 3_665 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.311 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.042