# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Ying-Chun Chen.' 'Jin-Gen Deng.' 'Xiao-Li Ma.' 'Yong Wu.' 'Jian-Wu Xie.' 'Dong Xue.' 'Lei Yue.' 'Jin Zhu.' _publ_contact_author_name 'Ying-Chun Chen' _publ_contact_author_address ; Department of Medicinal Chemistry The Key Lab. of Drug-Targetting of Education Ministry West China School of Pharmacy Sichuan University Chengdu 610041 CHINA ; _publ_contact_author_email YCCHENHUAXI@YAHOO.COM.CN _publ_requested_journal 'Chemical Communications' _publ_section_title ; Organocatalytic and Direct Asymmetric Vinylogous Michael Addition of a,a-Dicyanoolefins to a,b-Unsaturated Aldehydes ; # Attachment 'Y2044-enantiopure 4aa.CIF' data_y2044 _database_code_depnum_ccdc_archive 'CCDC 295476' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 N2 O' _chemical_formula_weight 264.32 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.076(1) _cell_length_b 13.777(3) _cell_length_c 17.439(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1459.74(51) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 35 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 13.65 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.20 _diffrn_reflns_number 2014 _diffrn_reflns_av_R_equivalents 0.0093 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1903 _reflns_number_gt 1215 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _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^)+(0.0360P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.039(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -3(3) _refine_ls_number_reflns 1903 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0791 _refine_ls_wR_factor_gt 0.0722 _refine_ls_goodness_of_fit_ref 0.905 _refine_ls_restrained_S_all 0.905 _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 O O 1.0901(4) 0.53840(16) 0.37058(12) 0.0963(7) Uani 1 1 d . . . N1 N 0.5422(5) 0.26782(15) 0.70375(12) 0.0896(8) Uani 1 1 d . . . N2 N 0.2025(4) 0.31624(17) 0.49181(14) 0.0920(9) Uani 1 1 d . . . C1 C 0.7507(4) 0.60783(15) 0.64772(11) 0.0498(6) Uani 1 1 d . . . C2 C 0.9051(5) 0.64305(18) 0.69939(12) 0.0640(7) Uani 1 1 d . . . H2 H 0.9057 0.7089 0.7110 0.077 Uiso 1 1 calc R . . C3 C 1.0566(5) 0.5837(2) 0.73377(13) 0.0718(8) Uani 1 1 d . . . H3 H 1.1558 0.6093 0.7690 0.086 Uiso 1 1 calc R . . C4 C 1.0621(5) 0.4865(2) 0.71632(13) 0.0657(7) Uani 1 1 d . . . H4 H 1.1684 0.4465 0.7381 0.079 Uiso 1 1 calc R . . C5 C 0.9094(4) 0.44883(17) 0.66644(12) 0.0541(6) Uani 1 1 d . . . H5 H 0.9125 0.3829 0.6552 0.065 Uiso 1 1 calc R . . C6 C 0.7496(4) 0.50752(14) 0.63231(10) 0.0436(5) Uani 1 1 d . . . C7 C 0.5833(4) 0.46867(14) 0.57930(11) 0.0424(5) Uani 1 1 d . . . C8 C 0.5084(4) 0.53730(14) 0.51736(11) 0.0419(5) Uani 1 1 d . . . H8 H 0.3859 0.5068 0.4898 0.050 Uiso 1 1 calc R . . C9 C 0.4187(4) 0.62597(16) 0.56057(12) 0.0558(7) Uani 1 1 d . . . H9A H 0.3597 0.6720 0.5238 0.067 Uiso 1 1 calc R . . H9B H 0.2991 0.6055 0.5937 0.067 Uiso 1 1 calc R . . C10 C 0.5939(5) 0.67591(16) 0.60866(12) 0.0643(7) Uani 1 1 d . . . H10A H 0.6774 0.7193 0.5759 0.077 Uiso 1 1 calc R . . H10B H 0.5218 0.7152 0.6474 0.077 Uiso 1 1 calc R . . C11 C 0.4899(4) 0.38011(14) 0.58717(12) 0.0466(6) Uani 1 1 d . . . C12 C 0.5255(5) 0.31811(15) 0.65228(14) 0.0605(7) Uani 1 1 d . . . C13 C 0.3307(5) 0.34499(17) 0.53386(15) 0.0610(7) Uani 1 1 d . . . C14 C 0.6917(4) 0.56015(14) 0.45898(11) 0.0410(5) Uani 1 1 d . . . H14 H 0.8200 0.5852 0.4867 0.049 Uiso 1 1 calc R . . C15 C 0.6150(4) 0.63713(14) 0.40159(11) 0.0541(7) Uani 1 1 d . . . H15A H 0.7236 0.6444 0.3620 0.065 Uiso 1 1 calc R . . H15B H 0.5956 0.6979 0.4276 0.065 Uiso 1 1 calc R . . H15C H 0.4779 0.6173 0.3792 0.065 Uiso 1 1 calc R . . C16 C 0.7582(4) 0.46778(14) 0.41702(12) 0.0521(6) Uani 1 1 d . . . H16A H 0.7869 0.4176 0.4547 0.063 Uiso 1 1 calc R . . H16B H 0.6351 0.4464 0.3859 0.063 Uiso 1 1 calc R . . C17 C 0.9530(5) 0.4773(2) 0.36732(15) 0.0718(8) Uani 1 1 d . . . H17 H 0.9703 0.4304 0.3294 0.086 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 O 0.0727(13) 0.1228(16) 0.0935(15) -0.0105(14) 0.0266(13) -0.0198(15) N1 0.131(2) 0.0667(14) 0.0712(14) 0.0259(12) 0.0092(18) -0.0059(17) N2 0.096(2) 0.0726(15) 0.108(2) -0.0038(15) -0.0254(19) -0.0211(16) C1 0.0694(16) 0.0486(12) 0.0314(10) 0.0011(10) 0.0078(13) -0.0009(13) C2 0.086(2) 0.0684(15) 0.0379(12) -0.0050(12) 0.0091(15) -0.0218(17) C3 0.072(2) 0.106(2) 0.0372(13) -0.0021(14) -0.0013(15) -0.0192(19) C4 0.0608(17) 0.094(2) 0.0425(13) 0.0124(14) -0.0019(14) -0.0012(18) C5 0.0573(15) 0.0622(14) 0.0429(12) 0.0059(12) 0.0011(13) 0.0055(15) C6 0.0523(13) 0.0489(12) 0.0296(10) 0.0059(10) 0.0042(12) 0.0006(12) C7 0.0481(13) 0.0417(11) 0.0374(11) 0.0006(9) 0.0092(12) 0.0084(12) C8 0.0455(13) 0.0422(11) 0.0380(11) 0.0047(9) 0.0006(11) 0.0011(12) C9 0.0641(17) 0.0554(13) 0.0479(12) 0.0101(11) 0.0114(13) 0.0170(15) C10 0.096(2) 0.0489(13) 0.0481(13) -0.0039(12) 0.0105(16) 0.0085(16) C11 0.0583(15) 0.0389(11) 0.0426(12) 0.0036(10) 0.0051(13) 0.0010(12) C12 0.0841(19) 0.0439(12) 0.0535(13) 0.0062(12) 0.0087(16) -0.0044(15) C13 0.0692(19) 0.0467(15) 0.0671(17) 0.0055(13) 0.0027(16) -0.0065(14) C14 0.0442(14) 0.0437(11) 0.0350(10) 0.0011(10) -0.0025(11) -0.0042(11) C15 0.0700(17) 0.0501(12) 0.0420(11) 0.0097(10) 0.0017(13) -0.0070(13) C16 0.0602(15) 0.0515(13) 0.0447(11) -0.0014(11) 0.0032(13) -0.0009(14) C17 0.075(2) 0.0828(19) 0.0573(16) -0.0110(15) 0.0193(17) 0.0041(18) _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 O C17 1.185(3) . ? N1 C12 1.138(3) . ? N2 C13 1.141(3) . ? C1 C2 1.389(3) . ? C1 C6 1.408(3) . ? C1 C10 1.500(3) . ? C2 C3 1.369(3) . ? C2 H2 0.9300 . ? C3 C4 1.374(3) . ? C3 H3 0.9300 . ? C4 C5 1.374(3) . ? C4 H4 0.9300 . ? C5 C6 1.397(3) . ? C5 H5 0.9300 . ? C6 C7 1.470(3) . ? C7 C11 1.352(3) . ? C7 C8 1.506(3) . ? C8 C9 1.535(3) . ? C8 C14 1.542(3) . ? C8 H8 0.9800 . ? C9 C10 1.520(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C13 1.426(3) . ? C11 C12 1.437(3) . ? C14 C16 1.523(3) . ? C14 C15 1.531(3) . ? C14 H14 0.9800 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.473(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17 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 C2 C1 C6 118.1(2) . . ? C2 C1 C10 120.3(2) . . ? C6 C1 C10 121.6(2) . . ? C3 C2 C1 122.0(2) . . ? C3 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? C2 C3 C4 120.1(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 119.5(3) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 121.4(2) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 118.9(2) . . ? C5 C6 C7 122.34(18) . . ? C1 C6 C7 118.7(2) . . ? C11 C7 C6 123.56(18) . . ? C11 C7 C8 120.8(2) . . ? C6 C7 C8 115.48(18) . . ? C7 C8 C9 104.77(15) . . ? C7 C8 C14 112.54(18) . . ? C9 C8 C14 114.71(17) . . ? C7 C8 H8 108.2 . . ? C9 C8 H8 108.2 . . ? C14 C8 H8 108.2 . . ? C10 C9 C8 112.5(2) . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9B 109.1 . . ? C8 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C1 C10 C9 114.35(18) . . ? C1 C10 H10A 108.7 . . ? C9 C10 H10A 108.7 . . ? C1 C10 H10B 108.7 . . ? C9 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C7 C11 C13 121.6(2) . . ? C7 C11 C12 123.6(2) . . ? C13 C11 C12 114.5(2) . . ? N1 C12 C11 176.4(3) . . ? N2 C13 C11 179.3(3) . . ? C16 C14 C15 110.22(16) . . ? C16 C14 C8 109.78(17) . . ? C15 C14 C8 110.68(18) . . ? C16 C14 H14 108.7 . . ? C15 C14 H14 108.7 . . ? C8 C14 H14 108.7 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C14 114.94(19) . . ? C17 C16 H16A 108.5 . . ? C14 C16 H16A 108.5 . . ? C17 C16 H16B 108.5 . . ? C14 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? O C17 C16 126.8(3) . . ? O C17 H17 116.6 . . ? C16 C17 H17 116.6 . . ? 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 C6 C1 C2 C3 1.4(3) . . . . ? C10 C1 C2 C3 -177.3(2) . . . . ? C1 C2 C3 C4 1.4(4) . . . . ? C2 C3 C4 C5 -2.5(4) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C4 C5 C6 C1 2.1(3) . . . . ? C4 C5 C6 C7 -179.4(2) . . . . ? C2 C1 C6 C5 -3.1(3) . . . . ? C10 C1 C6 C5 175.62(19) . . . . ? C2 C1 C6 C7 178.40(18) . . . . ? C10 C1 C6 C7 -2.9(3) . . . . ? C5 C6 C7 C11 36.0(3) . . . . ? C1 C6 C7 C11 -145.5(2) . . . . ? C5 C6 C7 C8 -148.33(19) . . . . ? C1 C6 C7 C8 30.1(3) . . . . ? C11 C7 C8 C9 117.9(2) . . . . ? C6 C7 C8 C9 -57.9(2) . . . . ? C11 C7 C8 C14 -116.8(2) . . . . ? C6 C7 C8 C14 67.4(2) . . . . ? C7 C8 C9 C10 61.9(2) . . . . ? C14 C8 C9 C10 -62.0(2) . . . . ? C2 C1 C10 C9 -173.6(2) . . . . ? C6 C1 C10 C9 7.7(3) . . . . ? C8 C9 C10 C1 -38.6(3) . . . . ? C6 C7 C11 C13 -179.4(2) . . . . ? C8 C7 C11 C13 5.2(3) . . . . ? C6 C7 C11 C12 6.6(3) . . . . ? C8 C7 C11 C12 -168.8(2) . . . . ? C7 C11 C12 N1 139(4) . . . . ? C13 C11 C12 N1 -36(4) . . . . ? C7 C11 C13 N2 -158(27) . . . . ? C12 C11 C13 N2 16(27) . . . . ? C7 C8 C14 C16 63.3(2) . . . . ? C9 C8 C14 C16 -177.00(19) . . . . ? C7 C8 C14 C15 -174.76(17) . . . . ? C9 C8 C14 C15 -55.1(2) . . . . ? C15 C14 C16 C17 65.9(3) . . . . ? C8 C14 C16 C17 -171.93(19) . . . . ? C14 C16 C17 O 19.8(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.112 _refine_diff_density_min -0.116 _refine_diff_density_rms 0.028 # Attachment 'Y2045-enantiopure 4ca.CIF' data_y2045 _database_code_depnum_ccdc_archive 'CCDC 295477' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 N2 O S' _chemical_formula_weight 282.35 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' S S 0.1246 0.1234 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.534(1) _cell_length_b 7.610(1) _cell_length_c 12.685(1) _cell_angle_alpha 90.00 _cell_angle_beta 97.25(1) _cell_angle_gamma 90.00 _cell_volume 721.52(14) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 29 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 14.81 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9029 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.98 _diffrn_reflns_number 3788 _diffrn_reflns_av_R_equivalents 0.0126 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3158 _reflns_number_gt 2554 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _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^)+(0.0510P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.035(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(8) _refine_ls_number_reflns 3158 _refine_ls_number_parameters 183 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0924 _refine_ls_wR_factor_gt 0.0885 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 S S 0.95450(9) 0.14273(8) 0.11199(4) 0.0673(2) Uani 1 1 d . . . O O 0.4373(2) 0.4601(3) 0.20959(16) 0.0751(5) Uani 1 1 d . . . N1 N 0.5965(4) -0.0865(3) 0.4971(2) 0.0962(8) Uani 1 1 d . . . N2 N 0.9059(4) 0.3726(3) 0.57325(19) 0.0945(8) Uani 1 1 d . . . C1 C 0.7436(3) 0.0723(3) 0.13839(16) 0.0533(5) Uani 1 1 d . . . C2 C 0.6423(5) -0.0241(3) 0.05788(19) 0.0807(9) Uani 1 1 d . . . H2 H 0.6908 -0.0489 -0.0043 0.097 Uiso 1 1 calc R . . C3 C 0.4759(5) -0.0819(4) 0.0686(3) 0.0972(12) Uani 1 1 d . . . H3 H 0.4119 -0.1468 0.0144 0.117 Uiso 1 1 calc R . . C4 C 0.3998(4) -0.0441(3) 0.1610(3) 0.0856(10) Uani 1 1 d . . . H4 H 0.2847 -0.0822 0.1683 0.103 Uiso 1 1 calc R . . C5 C 0.4960(3) 0.0492(3) 0.2405(2) 0.0600(6) Uani 1 1 d . . . H5 H 0.4444 0.0753 0.3015 0.072 Uiso 1 1 calc R . . C6 C 0.6707(2) 0.1068(2) 0.23271(14) 0.0427(5) Uani 1 1 d . . . C7 C 0.7704(2) 0.2080(2) 0.31928(13) 0.0364(4) Uani 1 1 d . . . C8 C 0.9050(2) 0.3402(2) 0.29057(14) 0.0383(4) Uani 1 1 d . . . H8 H 0.9659 0.3882 0.3572 0.046 Uiso 1 1 calc R . . C9 C 1.0430(3) 0.2343(3) 0.23879(16) 0.0505(5) Uani 1 1 d . . . H9A H 1.0872 0.1396 0.2861 0.061 Uiso 1 1 calc R . . H9B H 1.1434 0.3098 0.2293 0.061 Uiso 1 1 calc R . . C10 C 0.7516(3) 0.1783(3) 0.42319(14) 0.0459(5) Uani 1 1 d . . . C11 C 0.6599(3) 0.0309(3) 0.46153(18) 0.0622(6) Uani 1 1 d . . . C12 C 0.8391(3) 0.2881(3) 0.50603(16) 0.0593(6) Uani 1 1 d . . . C13 C 0.8233(3) 0.4964(2) 0.22374(15) 0.0441(4) Uani 1 1 d . . . H13 H 0.7502 0.4497 0.1606 0.053 Uiso 1 1 calc R . . C14 C 0.9699(3) 0.6115(3) 0.18725(19) 0.0693(7) Uani 1 1 d . . . H14A H 1.0470 0.6533 0.2481 0.083 Uiso 1 1 calc R . . H14B H 0.9164 0.7098 0.1478 0.083 Uiso 1 1 calc R . . H14C H 1.0385 0.5439 0.1429 0.083 Uiso 1 1 calc R . . C15 C 0.7023(3) 0.6055(3) 0.28696(17) 0.0533(5) Uani 1 1 d . . . H15A H 0.7462 0.5934 0.3618 0.064 Uiso 1 1 calc R . . H15B H 0.7153 0.7281 0.2684 0.064 Uiso 1 1 calc R . . C16 C 0.5088(3) 0.5629(3) 0.2725(2) 0.0593(6) Uani 1 1 d . . . H16 H 0.4371 0.6209 0.3160 0.071 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 S 0.0940(4) 0.0590(4) 0.0543(3) -0.0016(3) 0.0304(3) 0.0162(4) O 0.0607(10) 0.0669(11) 0.0977(13) 0.0027(11) 0.0103(9) -0.0047(9) N1 0.136(2) 0.0716(14) 0.0927(17) 0.0034(14) 0.0597(16) -0.0267(16) N2 0.140(2) 0.0883(18) 0.0517(11) -0.0125(12) -0.0009(13) -0.0243(17) C1 0.0763(14) 0.0349(10) 0.0452(10) 0.0002(8) -0.0065(10) 0.0115(10) C2 0.136(3) 0.0474(13) 0.0493(13) -0.0070(11) -0.0232(15) 0.0111(17) C3 0.122(3) 0.0495(15) 0.099(2) -0.0094(16) -0.069(2) 0.0013(17) C4 0.0669(17) 0.0431(14) 0.133(3) 0.0013(17) -0.0418(18) -0.0012(13) C5 0.0492(12) 0.0369(10) 0.0893(17) -0.0031(11) -0.0092(11) 0.0034(10) C6 0.0436(10) 0.0298(10) 0.0520(10) -0.0028(8) -0.0046(8) 0.0062(8) C7 0.0359(9) 0.0302(8) 0.0433(9) -0.0006(7) 0.0061(7) 0.0064(7) C8 0.0374(9) 0.0412(10) 0.0352(9) 0.0016(8) 0.0005(7) -0.0003(8) C9 0.0475(11) 0.0461(12) 0.0601(12) 0.0092(10) 0.0158(9) 0.0074(9) C10 0.0534(11) 0.0401(10) 0.0463(10) -0.0023(9) 0.0149(8) -0.0016(9) C11 0.0854(16) 0.0505(13) 0.0570(13) -0.0060(11) 0.0334(12) -0.0057(13) C12 0.0837(15) 0.0542(12) 0.0414(10) -0.0025(10) 0.0129(11) -0.0103(12) C13 0.0539(11) 0.0376(10) 0.0401(9) 0.0009(8) 0.0035(8) 0.0055(9) C14 0.0908(17) 0.0480(13) 0.0734(14) 0.0166(11) 0.0268(13) 0.0034(13) C15 0.0607(12) 0.0402(12) 0.0586(11) -0.0020(9) 0.0059(9) 0.0106(10) C16 0.0663(14) 0.0513(13) 0.0634(13) 0.0121(11) 0.0202(11) 0.0104(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 S C1 1.749(3) . ? S C9 1.802(2) . ? O C16 1.196(3) . ? N1 C11 1.133(3) . ? N2 C12 1.134(3) . ? C1 C2 1.403(3) . ? C1 C6 1.403(3) . ? C2 C3 1.351(4) . ? C2 H2 0.9300 . ? C3 C4 1.398(5) . ? C3 H3 0.9300 . ? C4 C5 1.365(4) . ? C4 H4 0.9300 . ? C5 C6 1.402(3) . ? C5 H5 0.9300 . ? C6 C7 1.468(2) . ? C7 C10 1.362(2) . ? C7 C8 1.505(2) . ? C8 C9 1.528(3) . ? C8 C13 1.542(2) . ? C8 H8 0.9800 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.434(3) . ? C10 C12 1.436(3) . ? C13 C14 1.526(3) . ? C13 C15 1.533(3) . ? C13 H13 0.9800 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.481(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16 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 C1 S C9 100.97(10) . . ? C2 C1 C6 118.9(2) . . ? C2 C1 S 116.4(2) . . ? C6 C1 S 124.67(16) . . ? C3 C2 C1 121.6(3) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C2 C3 C4 120.1(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 119.4(3) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 121.7(3) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C5 C6 C1 118.28(19) . . ? C5 C6 C7 120.47(17) . . ? C1 C6 C7 121.18(17) . . ? C10 C7 C6 122.05(16) . . ? C10 C7 C8 120.05(16) . . ? C6 C7 C8 117.80(15) . . ? C7 C8 C9 105.50(15) . . ? C7 C8 C13 114.46(14) . . ? C9 C8 C13 114.58(15) . . ? C7 C8 H8 107.3 . . ? C9 C8 H8 107.3 . . ? C13 C8 H8 107.3 . . ? C8 C9 S 113.11(14) . . ? C8 C9 H9A 109.0 . . ? S C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? S C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C7 C10 C11 124.85(17) . . ? C7 C10 C12 121.13(18) . . ? C11 C10 C12 113.79(17) . . ? N1 C11 C10 175.5(3) . . ? N2 C12 C10 178.2(3) . . ? C14 C13 C15 110.40(17) . . ? C14 C13 C8 110.83(16) . . ? C15 C13 C8 110.63(15) . . ? C14 C13 H13 108.3 . . ? C15 C13 H13 108.3 . . ? C8 C13 H13 108.3 . . ? 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 . . ? C16 C15 C13 117.25(19) . . ? C16 C15 H15A 108.0 . . ? C13 C15 H15A 108.0 . . ? C16 C15 H15B 108.0 . . ? C13 C15 H15B 108.0 . . ? H15A C15 H15B 107.2 . . ? O C16 C15 125.4(2) . . ? O C16 H16 117.3 . . ? C15 C16 H16 117.3 . . ? 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 C9 S C1 C2 -173.59(16) . . . . ? C9 S C1 C6 6.93(19) . . . . ? C6 C1 C2 C3 1.0(3) . . . . ? S C1 C2 C3 -178.5(2) . . . . ? C1 C2 C3 C4 0.8(4) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? C3 C4 C5 C6 -0.8(4) . . . . ? C4 C5 C6 C1 2.5(3) . . . . ? C4 C5 C6 C7 179.57(19) . . . . ? C2 C1 C6 C5 -2.6(3) . . . . ? S C1 C6 C5 176.87(15) . . . . ? C2 C1 C6 C7 -179.60(16) . . . . ? S C1 C6 C7 -0.1(3) . . . . ? C5 C6 C7 C10 34.4(3) . . . . ? C1 C6 C7 C10 -148.65(18) . . . . ? C5 C6 C7 C8 -149.38(17) . . . . ? C1 C6 C7 C8 27.6(2) . . . . ? C10 C7 C8 C9 115.13(18) . . . . ? C6 C7 C8 C9 -61.15(18) . . . . ? C10 C7 C8 C13 -117.96(18) . . . . ? C6 C7 C8 C13 65.75(19) . . . . ? C7 C8 C9 S 68.00(16) . . . . ? C13 C8 C9 S -58.83(19) . . . . ? C1 S C9 C8 -41.20(16) . . . . ? C6 C7 C10 C11 11.0(3) . . . . ? C8 C7 C10 C11 -165.13(19) . . . . ? C6 C7 C10 C12 -174.89(18) . . . . ? C8 C7 C10 C12 9.0(3) . . . . ? C7 C10 C11 N1 137(3) . . . . ? C12 C10 C11 N1 -37(3) . . . . ? C7 C10 C12 N2 172(9) . . . . ? C11 C10 C12 N2 -13(10) . . . . ? C7 C8 C13 C14 -173.23(16) . . . . ? C9 C8 C13 C14 -51.2(2) . . . . ? C7 C8 C13 C15 64.0(2) . . . . ? C9 C8 C13 C15 -173.96(17) . . . . ? C14 C13 C15 C16 143.11(19) . . . . ? C8 C13 C15 C16 -93.8(2) . . . . ? C13 C15 C16 O -6.2(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.174 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.029 # Attachment 'Y2068-racemic 5a.CIF' data_y2068 _database_code_depnum_ccdc_archive 'CCDC 295478' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 N2 O' _chemical_formula_weight 326.38 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.603(4) _cell_length_b 6.159(1) _cell_length_c 18.040(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.72(2) _cell_angle_gamma 90.00 _cell_volume 1717.96(73) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 28 _cell_measurement_theta_min 3.56 _cell_measurement_theta_max 12.95 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.52 _diffrn_reflns_number 3776 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0527 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.49 _reflns_number_total 3203 _reflns_number_gt 1916 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _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^)+(0.0426P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0204(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3203 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0815 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1033 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _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 O O 0.46401(8) 0.6747(3) 0.58182(8) 0.0558(4) Uani 1 1 d . . . H0 H 0.5028 0.7615 0.5771 0.067 Uiso 1 1 calc R . . N1 N 0.44231(11) 0.8848(3) 0.39617(10) 0.0585(5) Uani 1 1 d . . . N2 N 0.34329(12) 0.2927(4) 0.47592(12) 0.0687(6) Uani 1 1 d . . . C1 C 0.20614(11) 0.8175(3) 0.39080(10) 0.0389(5) Uani 1 1 d . . . C2 C 0.22704(13) 0.6854(4) 0.33407(10) 0.0514(6) Uani 1 1 d . . . H2 H 0.2705 0.5822 0.3447 0.062 Uiso 1 1 calc R . . C3 C 0.18485(15) 0.7031(5) 0.26177(12) 0.0674(7) Uani 1 1 d . . . H3 H 0.1996 0.6126 0.2242 0.081 Uiso 1 1 calc R . . C4 C 0.12127(16) 0.8550(5) 0.24626(13) 0.0744(8) Uani 1 1 d . . . H4 H 0.0927 0.8682 0.1978 0.089 Uiso 1 1 calc R . . C5 C 0.09910(13) 0.9883(5) 0.30154(14) 0.0681(7) Uani 1 1 d . . . H5 H 0.0557 1.0912 0.2900 0.082 Uiso 1 1 calc R . . C6 C 0.14033(11) 0.9722(4) 0.37452(11) 0.0488(6) Uani 1 1 d . . . C7 C 0.11623(13) 1.1083(4) 0.43737(12) 0.0592(6) Uani 1 1 d . . . H7A H 0.0587 1.1675 0.4238 0.071 Uiso 1 1 calc R . . H7B H 0.1564 1.2283 0.4468 0.071 Uiso 1 1 calc R . . C8 C 0.11851(12) 0.9704(4) 0.50737(12) 0.0550(6) Uani 1 1 d . . . H8A H 0.1073 1.0611 0.5490 0.066 Uiso 1 1 calc R . . H8B H 0.0736 0.8607 0.4997 0.066 Uiso 1 1 calc R . . C9 C 0.20577(11) 0.8618(3) 0.52579(10) 0.0372(5) Uani 1 1 d . . . C10 C 0.24788(10) 0.8005(3) 0.46940(9) 0.0324(4) Uani 1 1 d . . . C11 C 0.34116(11) 0.7149(3) 0.48500(9) 0.0337(5) Uani 1 1 d . . . C12 C 0.38328(11) 0.7785(3) 0.56530(10) 0.0390(5) Uani 1 1 d . . . H12 H 0.3913 0.9362 0.5683 0.047 Uiso 1 1 calc R . . C13 C 0.32366(11) 0.7083(4) 0.61985(10) 0.0445(5) Uani 1 1 d . . . H13A H 0.3518 0.7310 0.6705 0.053 Uiso 1 1 calc R . . H13B H 0.3114 0.5545 0.6135 0.053 Uiso 1 1 calc R . . C14 C 0.23928(12) 0.8358(3) 0.60782(10) 0.0426(5) Uani 1 1 d . . . H14 H 0.2514 0.9815 0.6284 0.051 Uiso 1 1 calc R . . C15 C 0.17286(12) 0.7315(3) 0.65153(10) 0.0426(5) Uani 1 1 d . . . C16 C 0.15938(13) 0.8115(4) 0.72028(11) 0.0506(6) Uani 1 1 d . . . H16 H 0.1897 0.9338 0.7393 0.061 Uiso 1 1 calc R . . C17 C 0.10165(13) 0.7137(4) 0.76169(12) 0.0569(6) Uani 1 1 d . . . H17 H 0.0935 0.7698 0.8081 0.068 Uiso 1 1 calc R . . C18 C 0.05684(14) 0.5352(4) 0.73423(12) 0.0585(7) Uani 1 1 d . . . H18 H 0.0177 0.4696 0.7618 0.070 Uiso 1 1 calc R . . C19 C 0.06918(15) 0.4517(4) 0.66585(13) 0.0661(7) Uani 1 1 d . . . H19 H 0.0384 0.3299 0.6471 0.079 Uiso 1 1 calc R . . C20 C 0.12740(14) 0.5492(4) 0.62512(12) 0.0591(6) Uani 1 1 d . . . H20 H 0.1361 0.4910 0.5791 0.071 Uiso 1 1 calc R . . C21 C 0.39611(11) 0.8079(3) 0.43221(10) 0.0378(5) Uani 1 1 d . . . C22 C 0.34315(12) 0.4761(4) 0.47864(11) 0.0428(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O 0.0310(7) 0.0737(11) 0.0596(9) 0.0173(8) -0.0058(7) -0.0014(7) N1 0.0471(10) 0.0763(14) 0.0552(11) 0.0079(11) 0.0175(9) -0.0086(10) N2 0.0671(14) 0.0471(13) 0.0926(16) -0.0012(12) 0.0132(11) 0.0032(11) C1 0.0297(10) 0.0494(13) 0.0369(11) 0.0055(10) 0.0021(8) -0.0037(10) C2 0.0465(12) 0.0690(16) 0.0376(11) -0.0012(11) 0.0013(9) -0.0034(12) C3 0.0684(16) 0.092(2) 0.0385(13) -0.0048(13) -0.0050(11) -0.0140(16) C4 0.0601(15) 0.114(2) 0.0429(14) 0.0170(16) -0.0157(12) -0.0176(17) C5 0.0410(12) 0.093(2) 0.0652(16) 0.0297(16) -0.0101(12) 0.0039(14) C6 0.0289(10) 0.0646(15) 0.0521(13) 0.0167(12) 0.0022(9) 0.0015(11) C7 0.0394(11) 0.0668(16) 0.0729(16) 0.0177(13) 0.0130(11) 0.0200(12) C8 0.0400(11) 0.0680(16) 0.0599(13) 0.0061(13) 0.0168(10) 0.0142(12) C9 0.0328(10) 0.0409(12) 0.0391(11) 0.0012(9) 0.0091(8) 0.0010(9) C10 0.0267(9) 0.0353(11) 0.0349(10) 0.0023(9) 0.0027(8) 0.0008(9) C11 0.0299(10) 0.0379(12) 0.0335(10) 0.0026(9) 0.0049(8) -0.0003(9) C12 0.0309(10) 0.0469(12) 0.0375(11) 0.0049(10) -0.0011(8) -0.0029(9) C13 0.0448(11) 0.0567(14) 0.0304(10) 0.0045(10) -0.0005(8) -0.0065(11) C14 0.0473(12) 0.0453(13) 0.0365(11) -0.0046(10) 0.0103(9) -0.0055(10) C15 0.0446(12) 0.0478(13) 0.0372(11) 0.0003(10) 0.0119(9) -0.0007(10) C16 0.0503(12) 0.0638(15) 0.0394(11) -0.0049(11) 0.0124(10) -0.0041(12) C17 0.0529(13) 0.0780(18) 0.0425(12) -0.0004(13) 0.0167(11) 0.0027(14) C18 0.0471(13) 0.0765(18) 0.0553(14) 0.0191(14) 0.0193(11) 0.0020(13) C19 0.0679(15) 0.0661(18) 0.0676(16) -0.0006(13) 0.0205(13) -0.0192(14) C20 0.0696(15) 0.0618(16) 0.0505(13) -0.0109(12) 0.0246(11) -0.0167(13) C21 0.0297(10) 0.0451(12) 0.0385(11) -0.0003(10) 0.0043(8) 0.0026(10) C22 0.0305(11) 0.0490(15) 0.0492(13) 0.0021(11) 0.0070(9) 0.0028(11) _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 O C12 1.408(2) . ? O H0 0.8200 . ? N1 C21 1.137(2) . ? N2 C22 1.131(3) . ? C1 C2 1.380(3) . ? C1 C6 1.403(3) . ? C1 C10 1.482(2) . ? C2 C3 1.384(3) . ? C2 H2 0.9300 . ? C3 C4 1.365(3) . ? C3 H3 0.9300 . ? C4 C5 1.372(3) . ? C4 H4 0.9300 . ? C5 C6 1.389(3) . ? C5 H5 0.9300 . ? C6 C7 1.498(3) . ? C7 C8 1.518(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.513(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.337(2) . ? C9 C14 1.510(3) . ? C10 C11 1.538(2) . ? C11 C22 1.476(3) . ? C11 C21 1.480(2) . ? C11 C12 1.558(2) . ? C12 C13 1.506(2) . ? C12 H12 0.9800 . ? C13 C14 1.524(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.526(2) . ? C14 H14 0.9800 . ? C15 C16 1.377(3) . ? C15 C20 1.379(3) . ? C16 C17 1.383(3) . ? C16 H16 0.9300 . ? C17 C18 1.360(3) . ? C17 H17 0.9300 . ? C18 C19 1.374(3) . ? C18 H18 0.9300 . ? C19 C20 1.380(3) . ? C19 H19 0.9300 . ? C20 H20 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 C12 O H0 109.5 . . ? C2 C1 C6 118.96(18) . . ? C2 C1 C10 123.40(18) . . ? C6 C1 C10 117.61(18) . . ? C1 C2 C3 121.5(2) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C4 C3 C2 119.2(2) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 120.6(2) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 121.1(2) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 118.7(2) . . ? C5 C6 C7 123.1(2) . . ? C1 C6 C7 118.20(17) . . ? C6 C7 C8 109.67(19) . . ? C6 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? C6 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C9 C8 C7 110.47(16) . . ? C9 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? C9 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? C10 C9 C14 125.07(16) . . ? C10 C9 C8 118.51(17) . . ? C14 C9 C8 116.40(16) . . ? C9 C10 C1 120.66(16) . . ? C9 C10 C11 120.48(16) . . ? C1 C10 C11 118.86(15) . . ? C22 C11 C21 108.39(16) . . ? C22 C11 C10 110.88(16) . . ? C21 C11 C10 111.45(15) . . ? C22 C11 C12 108.18(16) . . ? C21 C11 C12 107.01(15) . . ? C10 C11 C12 110.77(14) . . ? O C12 C13 110.18(15) . . ? O C12 C11 109.65(15) . . ? C13 C12 C11 108.35(15) . . ? O C12 H12 109.5 . . ? C13 C12 H12 109.5 . . ? C11 C12 H12 109.5 . . ? C12 C13 C14 110.90(16) . . ? C12 C13 H13A 109.5 . . ? C14 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 108.0 . . ? C9 C14 C13 111.89(15) . . ? C9 C14 C15 112.40(16) . . ? C13 C14 C15 110.07(16) . . ? C9 C14 H14 107.4 . . ? C13 C14 H14 107.4 . . ? C15 C14 H14 107.4 . . ? C16 C15 C20 117.97(19) . . ? C16 C15 C14 120.76(19) . . ? C20 C15 C14 121.20(18) . . ? C15 C16 C17 121.3(2) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C18 C17 C16 119.7(2) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C19 120.2(2) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C20 119.8(2) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C15 C20 C19 121.0(2) . . ? C15 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? N1 C21 C11 174.9(2) . . ? N2 C22 C11 177.6(2) . . ? 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 C6 C1 C2 C3 0.3(3) . . . . ? C10 C1 C2 C3 178.3(2) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C4 C5 C6 C1 0.6(3) . . . . ? C4 C5 C6 C7 -177.7(2) . . . . ? C2 C1 C6 C5 -0.6(3) . . . . ? C10 C1 C6 C5 -178.78(18) . . . . ? C2 C1 C6 C7 177.70(19) . . . . ? C10 C1 C6 C7 -0.4(3) . . . . ? C5 C6 C7 C8 139.6(2) . . . . ? C1 C6 C7 C8 -38.7(3) . . . . ? C6 C7 C8 C9 54.8(2) . . . . ? C7 C8 C9 C10 -34.0(3) . . . . ? C7 C8 C9 C14 144.71(19) . . . . ? C14 C9 C10 C1 175.13(18) . . . . ? C8 C9 C10 C1 -6.3(3) . . . . ? C14 C9 C10 C11 -6.0(3) . . . . ? C8 C9 C10 C11 172.56(18) . . . . ? C2 C1 C10 C9 -152.81(19) . . . . ? C6 C1 C10 C9 25.2(3) . . . . ? C2 C1 C10 C11 28.3(3) . . . . ? C6 C1 C10 C11 -153.66(17) . . . . ? C9 C10 C11 C22 102.7(2) . . . . ? C1 C10 C11 C22 -78.4(2) . . . . ? C9 C10 C11 C21 -136.43(19) . . . . ? C1 C10 C11 C21 42.5(2) . . . . ? C9 C10 C11 C12 -17.4(2) . . . . ? C1 C10 C11 C12 161.49(16) . . . . ? C22 C11 C12 O 50.56(19) . . . . ? C21 C11 C12 O -66.04(19) . . . . ? C10 C11 C12 O 172.28(14) . . . . ? C22 C11 C12 C13 -69.73(19) . . . . ? C21 C11 C12 C13 173.67(16) . . . . ? C10 C11 C12 C13 52.0(2) . . . . ? O C12 C13 C14 174.26(16) . . . . ? C11 C12 C13 C14 -65.8(2) . . . . ? C10 C9 C14 C13 -6.2(3) . . . . ? C8 C9 C14 C13 175.26(17) . . . . ? C10 C9 C14 C15 -130.6(2) . . . . ? C8 C9 C14 C15 50.8(2) . . . . ? C12 C13 C14 C9 42.3(2) . . . . ? C12 C13 C14 C15 168.07(16) . . . . ? C9 C14 C15 C16 -136.4(2) . . . . ? C13 C14 C15 C16 98.1(2) . . . . ? C9 C14 C15 C20 46.5(3) . . . . ? C13 C14 C15 C20 -78.9(2) . . . . ? C20 C15 C16 C17 -0.4(3) . . . . ? C14 C15 C16 C17 -177.63(18) . . . . ? C15 C16 C17 C18 -0.2(3) . . . . ? C16 C17 C18 C19 0.3(3) . . . . ? C17 C18 C19 C20 0.2(4) . . . . ? C16 C15 C20 C19 1.0(3) . . . . ? C14 C15 C20 C19 178.1(2) . . . . ? C18 C19 C20 C15 -0.8(4) . . . . ? C22 C11 C21 N1 -114(2) . . . . ? C10 C11 C21 N1 123(2) . . . . ? C12 C11 C21 N1 2(2) . . . . ? C21 C11 C22 N2 169(6) . . . . ? C10 C11 C22 N2 -68(6) . . . . ? C12 C11 C22 N2 54(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 O H0 N1 0.82 2.37 3.082(2) 146.2 3_676 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.174 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.033