# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author 'Andrei S.Batsanov' _publ_contact_author_email a.s.batsanov@durham.ac.uk _publ_section_title ; Stereoselective Synthesis and Rearrangement-Fragmentation of Arylidene Diketopiperazines ; _publ_contact_author_name 'Andrei S.Batsanov' loop_ _publ_author_name 'Shouxin Liu' 'Yun Mu' 'Jianrong Han' 'Xiaoli Zhen' 'Yihua Yang' ; Xia Tian ; 'Andrew Whiting' #===END data_5a.6a _database_code_depnum_ccdc_archive 'CCDC 696109' #TrackingRef 'Combined-DKP-structures.cif' _database_code_CSD 696189 _audit_creation_method SHELXL-97 _chemical_name_systematic ; racemic cyclo[2-hydroxy-2-[(3,4,5-trimethyloxy)phenylmethyl]glycyl-prolyl ; _chemical_name_common ;racemic cyclo(2-hydroxy-2-((3,4,5- trimethyloxy)phenylmethyl)glycyl-prolyl ; _chemical_melting_point ? _chemical_formula_moiety 'C17 H22 N2 O6' _chemical_formula_sum 'C17 H22 N2 O6' _chemical_formula_weight 350.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.525(3) _cell_length_b 10.852(4) _cell_length_c 11.633(4) _cell_angle_alpha 103.951(6) _cell_angle_beta 105.568(7) _cell_angle_gamma 99.030(6) _cell_volume 862.8(6) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 922 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 21.38 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9777 _exptl_absorpt_correction_T_max 0.9878 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 4282 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0722 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3014 _reflns_number_gt 1437 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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. ; _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^)+(0.0911P)^2^+0.0142P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3014 _refine_ls_number_parameters 230 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1443 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1914 _refine_ls_wR_factor_gt 0.1453 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 0.6250(4) 0.8881(3) 0.8946(3) 0.0757(9) Uani 1 1 d . . . O2 O 0.7634(4) 0.7158(3) 0.9993(3) 0.0742(9) Uani 1 1 d . . . O3 O 1.0689(5) 0.6374(3) 0.9616(3) 0.0815(10) Uani 1 1 d . . . O4 O 1.0288(4) 0.8156(2) 0.4219(2) 0.0534(7) Uani 1 1 d . . . H4 H 1.0900 0.8918 0.4479 0.080 Uiso 1 1 calc R . . O5 O 0.7592(3) 0.4395(2) 0.4015(2) 0.0663(8) Uani 1 1 d . . . O6 O 0.7404(4) 0.9424(3) 0.5043(3) 0.0720(9) Uani 1 1 d . . . N1 N 0.9125(4) 0.6506(3) 0.4930(3) 0.0445(8) Uani 1 1 d . . . H1 H 1.0050 0.6270 0.5369 0.053 Uiso 1 1 calc R . . N2 N 0.5968(5) 0.7331(3) 0.4032(3) 0.0575(9) Uani 1 1 d . . . C1 C 0.9880(5) 0.8320(3) 0.7421(3) 0.0452(9) Uani 1 1 d . . . C2 C 0.8401(5) 0.8801(3) 0.7714(3) 0.0509(10) Uani 1 1 d . . . H2 H 0.7871 0.9359 0.7306 0.061 Uiso 1 1 calc R . . C3 C 0.7712(6) 0.8455(4) 0.8608(4) 0.0548(10) Uani 1 1 d . . . C4 C 0.8470(6) 0.7617(4) 0.9207(4) 0.0551(10) Uani 1 1 d . . . C5 C 0.9990(6) 0.7161(3) 0.8950(4) 0.0568(11) Uani 1 1 d . . . C6 C 1.0689(6) 0.7508(3) 0.8063(3) 0.0544(10) Uani 1 1 d . . . H6 H 1.1704 0.7200 0.7891 0.065 Uiso 1 1 calc R . . C7 C 0.5681(7) 0.9918(5) 0.8538(4) 0.0878(15) Uani 1 1 d . . . H7A H 0.6736 1.0666 0.8856 0.132 Uiso 1 1 calc R . . H7B H 0.4666 1.0134 0.8840 0.132 Uiso 1 1 calc R . . H7C H 0.5253 0.9662 0.7641 0.132 Uiso 1 1 calc R . . C8 C 0.8395(7) 0.7883(5) 1.1252(4) 0.0956(17) Uani 1 1 d . . . H8A H 0.9667 0.7795 1.1578 0.143 Uiso 1 1 calc R . . H8B H 0.7630 0.7567 1.1709 0.143 Uiso 1 1 calc R . . H8C H 0.8410 0.8787 1.1335 0.143 Uiso 1 1 calc R . . C9 C 1.2205(8) 0.5861(5) 0.9354(5) 0.0997(17) Uani 1 1 d . . . H9A H 1.1834 0.5396 0.8480 0.150 Uiso 1 1 calc R . . H9B H 1.2512 0.5276 0.9838 0.150 Uiso 1 1 calc R . . H9C H 1.3297 0.6564 0.9566 0.150 Uiso 1 1 calc R . . C10 C 1.0601(5) 0.8646(3) 0.6413(3) 0.0462(10) Uani 1 1 d . . . H10A H 1.1862 0.8487 0.6536 0.055 Uiso 1 1 calc R . . H10B H 1.0720 0.9572 0.6512 0.055 Uiso 1 1 calc R . . C11 C 0.9376(5) 0.7891(3) 0.5086(3) 0.0405(9) Uani 1 1 d . . . C12 C 0.7483(5) 0.8281(4) 0.4726(4) 0.0473(10) Uani 1 1 d . . . C13 C 0.4042(6) 0.7517(4) 0.3631(5) 0.0824(14) Uani 1 1 d . . . H13A H 0.3936 0.8045 0.3062 0.099 Uiso 1 1 calc R . . H13B H 0.3694 0.7944 0.4344 0.099 Uiso 1 1 calc R . . C14 C 0.2797(6) 0.6171(5) 0.2987(4) 0.0864(15) Uani 1 1 d . . . H14A H 0.1764 0.6028 0.3327 0.104 Uiso 1 1 calc R . . H14B H 0.2267 0.6041 0.2097 0.104 Uiso 1 1 calc R . . C15 C 0.4058(6) 0.5266(5) 0.3226(5) 0.0916(16) Uani 1 1 d D . . H15A H 0.3880 0.4930 0.3899 0.110 Uiso 1 1 calc R . . H15B H 0.3769 0.4534 0.2482 0.110 Uiso 1 1 calc R . . C16 C 0.5975(6) 0.6003(4) 0.3565(5) 0.0859(15) Uani 1 1 d D . . H16 H 0.6133 0.5959 0.2748 0.103 Uiso 1 1 calc R . . C17 C 0.7627(5) 0.5559(4) 0.4188(3) 0.0477(10) 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 O1 0.083(2) 0.081(2) 0.089(2) 0.0323(18) 0.0563(18) 0.0316(18) O2 0.103(2) 0.0581(18) 0.0614(19) 0.0149(15) 0.0384(17) 0.0023(16) O3 0.119(3) 0.076(2) 0.079(2) 0.0430(18) 0.0479(19) 0.046(2) O4 0.0567(18) 0.0544(17) 0.0661(17) 0.0247(14) 0.0373(14) 0.0195(14) O5 0.0510(17) 0.0378(16) 0.091(2) 0.0005(14) 0.0059(14) 0.0168(13) O6 0.0623(19) 0.0448(17) 0.131(3) 0.0401(17) 0.0451(17) 0.0284(14) N1 0.0404(18) 0.0344(17) 0.061(2) 0.0166(15) 0.0133(15) 0.0176(14) N2 0.047(2) 0.050(2) 0.078(2) 0.0167(18) 0.0178(18) 0.0290(18) C1 0.054(2) 0.035(2) 0.046(2) 0.0077(18) 0.0196(19) 0.0083(18) C2 0.065(3) 0.039(2) 0.055(2) 0.0152(19) 0.028(2) 0.0167(19) C3 0.062(3) 0.047(2) 0.059(3) 0.009(2) 0.030(2) 0.011(2) C4 0.077(3) 0.041(2) 0.050(2) 0.0116(19) 0.031(2) 0.005(2) C5 0.081(3) 0.036(2) 0.054(3) 0.015(2) 0.023(2) 0.013(2) C6 0.068(3) 0.044(2) 0.056(2) 0.013(2) 0.028(2) 0.018(2) C7 0.074(3) 0.122(4) 0.090(4) 0.040(3) 0.039(3) 0.050(3) C8 0.130(5) 0.092(4) 0.057(3) 0.008(3) 0.035(3) 0.017(3) C9 0.137(5) 0.101(4) 0.105(4) 0.060(3) 0.057(4) 0.072(4) C10 0.049(2) 0.036(2) 0.061(3) 0.0151(18) 0.027(2) 0.0132(17) C11 0.045(2) 0.035(2) 0.055(2) 0.0202(18) 0.0262(19) 0.0173(17) C12 0.051(3) 0.044(2) 0.069(3) 0.031(2) 0.035(2) 0.025(2) C13 0.047(3) 0.082(4) 0.120(4) 0.029(3) 0.019(3) 0.036(3) C14 0.057(3) 0.103(4) 0.081(3) 0.003(3) 0.003(2) 0.039(3) C15 0.056(3) 0.081(3) 0.107(4) 0.001(3) -0.003(3) 0.023(3) C16 0.063(3) 0.072(3) 0.102(4) 0.003(3) 0.002(3) 0.034(3) C17 0.049(3) 0.041(2) 0.049(2) 0.0040(19) 0.0135(19) 0.020(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 O1 C3 1.372(4) . ? O1 C7 1.405(5) . ? O2 C4 1.382(4) . ? O2 C8 1.394(5) . ? O3 C5 1.360(4) . ? O3 C9 1.417(5) . ? O4 C11 1.421(4) . ? O4 H4 0.8200 . ? O5 C17 1.225(4) . ? O6 C12 1.222(4) . ? N1 C17 1.326(4) . ? N1 C11 1.446(4) . ? N1 H1 0.8600 . ? N2 C12 1.322(4) . ? N2 C16 1.414(5) . ? N2 C13 1.461(5) . ? C1 C2 1.388(5) . ? C1 C6 1.395(5) . ? C1 C10 1.509(5) . ? C2 C3 1.381(5) . ? C2 H2 0.9300 . ? C3 C4 1.376(5) . ? C4 C5 1.390(5) . ? C5 C6 1.378(5) . ? C6 H6 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.514(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.528(5) . ? C13 C14 1.496(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.491(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.434(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.475(5) . ? C16 H16 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 C3 O1 C7 117.2(3) . . ? C4 O2 C8 115.2(3) . . ? C5 O3 C9 117.3(3) . . ? C11 O4 H4 109.5 . . ? C17 N1 C11 127.3(3) . . ? C17 N1 H1 116.4 . . ? C11 N1 H1 116.4 . . ? C12 N2 C16 125.3(3) . . ? C12 N2 C13 124.3(3) . . ? C16 N2 C13 110.4(3) . . ? C2 C1 C6 119.0(3) . . ? C2 C1 C10 121.2(3) . . ? C6 C1 C10 119.8(3) . . ? C3 C2 C1 120.4(4) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? O1 C3 C4 115.7(4) . . ? O1 C3 C2 124.0(4) . . ? C4 C3 C2 120.3(4) . . ? C3 C4 O2 119.9(4) . . ? C3 C4 C5 119.8(4) . . ? O2 C4 C5 120.2(4) . . ? O3 C5 C6 124.2(4) . . ? O3 C5 C4 115.7(4) . . ? C6 C5 C4 120.1(4) . . ? C5 C6 C1 120.3(4) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O3 C9 H9A 109.5 . . ? O3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 C10 C11 115.3(3) . . ? C1 C10 H10A 108.5 . . ? C11 C10 H10A 108.5 . . ? C1 C10 H10B 108.5 . . ? C11 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? O4 C11 N1 106.4(3) . . ? O4 C11 C10 110.7(3) . . ? N1 C11 C10 109.4(3) . . ? O4 C11 C12 105.8(3) . . ? N1 C11 C12 112.3(3) . . ? C10 C11 C12 112.1(3) . . ? O6 C12 N2 122.2(3) . . ? O6 C12 C11 120.9(4) . . ? N2 C12 C11 116.9(3) . . ? N2 C13 C14 105.2(3) . . ? N2 C13 H13A 110.7 . . ? C14 C13 H13A 110.7 . . ? N2 C13 H13B 110.7 . . ? C14 C13 H13B 110.7 . . ? H13A C13 H13B 108.8 . . ? C15 C14 C13 105.4(3) . . ? C15 C14 H14A 110.7 . . ? C13 C14 H14A 110.7 . . ? C15 C14 H14B 110.7 . . ? C13 C14 H14B 110.7 . . ? H14A C14 H14B 108.8 . . ? C16 C15 C14 107.1(4) . . ? C16 C15 H15A 110.3 . . ? C14 C15 H15A 110.3 . . ? C16 C15 H15B 110.3 . . ? C14 C15 H15B 110.3 . . ? H15A C15 H15B 108.6 . . ? N2 C16 C15 106.7(4) . . ? N2 C16 C17 117.3(4) . . ? C15 C16 C17 122.6(4) . . ? N2 C16 H16 102.3 . . ? C15 C16 H16 102.3 . . ? C17 C16 H16 102.3 . . ? O5 C17 N1 123.4(3) . . ? O5 C17 C16 121.5(4) . . ? N1 C17 C16 115.1(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 C6 C1 C2 C3 -1.5(5) . . . . ? C10 C1 C2 C3 177.6(3) . . . . ? C7 O1 C3 C4 168.3(4) . . . . ? C7 O1 C3 C2 -12.8(6) . . . . ? C1 C2 C3 O1 -179.6(3) . . . . ? C1 C2 C3 C4 -0.8(6) . . . . ? O1 C3 C4 O2 6.3(5) . . . . ? C2 C3 C4 O2 -172.6(3) . . . . ? O1 C3 C4 C5 -178.3(3) . . . . ? C2 C3 C4 C5 2.7(6) . . . . ? C8 O2 C4 C3 -93.6(5) . . . . ? C8 O2 C4 C5 91.1(4) . . . . ? C9 O3 C5 C6 -1.4(6) . . . . ? C9 O3 C5 C4 178.3(4) . . . . ? C3 C4 C5 O3 177.8(3) . . . . ? O2 C4 C5 O3 -6.8(5) . . . . ? C3 C4 C5 C6 -2.5(6) . . . . ? O2 C4 C5 C6 172.9(3) . . . . ? O3 C5 C6 C1 179.9(3) . . . . ? C4 C5 C6 C1 0.2(6) . . . . ? C2 C1 C6 C5 1.8(5) . . . . ? C10 C1 C6 C5 -177.4(3) . . . . ? C2 C1 C10 C11 -77.4(4) . . . . ? C6 C1 C10 C11 101.7(4) . . . . ? C17 N1 C11 O4 -92.0(4) . . . . ? C17 N1 C11 C10 148.5(3) . . . . ? C17 N1 C11 C12 23.3(5) . . . . ? C1 C10 C11 O4 -173.1(3) . . . . ? C1 C10 C11 N1 -56.2(4) . . . . ? C1 C10 C11 C12 69.0(4) . . . . ? C16 N2 C12 O6 175.7(4) . . . . ? C13 N2 C12 O6 -3.7(6) . . . . ? C16 N2 C12 C11 -2.4(6) . . . . ? C13 N2 C12 C11 178.2(4) . . . . ? O4 C11 C12 O6 -80.1(4) . . . . ? N1 C11 C12 O6 164.3(3) . . . . ? C10 C11 C12 O6 40.7(5) . . . . ? O4 C11 C12 N2 98.0(4) . . . . ? N1 C11 C12 N2 -17.6(4) . . . . ? C10 C11 C12 N2 -141.2(3) . . . . ? C12 N2 C13 C14 -174.4(4) . . . . ? C16 N2 C13 C14 6.0(5) . . . . ? N2 C13 C14 C15 8.4(5) . . . . ? C13 C14 C15 C16 -19.8(6) . . . . ? C12 N2 C16 C15 161.8(4) . . . . ? C13 N2 C16 C15 -18.7(5) . . . . ? C12 N2 C16 C17 19.7(7) . . . . ? C13 N2 C16 C17 -160.7(4) . . . . ? C14 C15 C16 N2 23.7(6) . . . . ? C14 C15 C16 C17 163.3(4) . . . . ? C11 N1 C17 O5 172.6(3) . . . . ? C11 N1 C17 C16 -7.1(5) . . . . ? N2 C16 C17 O5 165.5(4) . . . . ? C15 C16 C17 O5 29.9(7) . . . . ? N2 C16 C17 N1 -14.7(6) . . . . ? C15 C16 C17 N1 -150.4(4) . . . . ? 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 O4 H4 O6 0.82 1.90 2.708(4) 170.8 2_776 N1 H1 O5 0.86 2.04 2.877(4) 165.1 2_766 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.254 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.045 #===END #====================================================================== data_4a _database_code_depnum_ccdc_archive 'CCDC 696110' #TrackingRef 'Combined-DKP-structures.cif' _database_code_CSD 696110 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (S)-cyclo[N-cyclohexyloxy-2-[(\b-pyridyl) methylene]glycyl-prolyl ; _chemical_name_common ;(S)-cyclo(N-cyclohexyloxy-2-((beta-pyridyl) methylene)glycyl- prolyl ; _chemical_melting_point ? _chemical_formula_moiety 'C19 H23 N3 O3' _chemical_formula_sum 'C19 H23 N3 O3' _chemical_formula_weight 341.40 _chemical_absolute_configuration syn 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 9.7941(14) _cell_length_b 10.3009(15) _cell_length_c 17.223(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1737.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 4139 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 24.95 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9214 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _exptl_special_details ; 2047 unique reflections after merging 1520 Friedel pairs ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 9847 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 26.43 _reflns_number_total 2047 _reflns_number_gt 1686 _reflns_threshold_expression I>2\s(I) _reflns_Friedel_coverage 0.74 _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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. ; _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^+0.2958P] 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 0.027(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'undeterminable, all \Df" set to 0, Friedel equivalents merged' _refine_ls_number_reflns 2047 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0829 _refine_ls_wR_factor_gt 0.0741 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 O1 O 0.03177(15) 0.48573(15) 0.32100(10) 0.0546(4) Uani 1 1 d . . . O2 O 0.49334(17) 0.46410(16) 0.16027(10) 0.0627(5) Uani 1 1 d . . . O3 O 0.38080(14) 0.69617(14) 0.18860(8) 0.0446(4) Uani 1 1 d . . . N1 N 0.21023(18) 0.36682(17) 0.28047(11) 0.0420(4) Uani 1 1 d . . . N2 N 0.33047(18) 0.58206(16) 0.22215(10) 0.0428(4) Uani 1 1 d . . . N3 N -0.0128(3) 0.9289(2) 0.42877(15) 0.0762(7) Uani 1 1 d . . . C1 C 0.2358(2) 0.5980(2) 0.28453(12) 0.0388(5) Uani 1 1 d . . . C2 C 0.1500(2) 0.4790(2) 0.29789(11) 0.0402(5) Uani 1 1 d . . . C3 C 0.1363(2) 0.2425(2) 0.28032(14) 0.0483(5) Uani 1 1 d . . . H3A H 0.0551 0.2476 0.2482 0.058 Uiso 1 1 calc R . . H3B H 0.1100 0.2178 0.3326 0.058 Uiso 1 1 calc R . . C4 C 0.2383(3) 0.1470(3) 0.24676(15) 0.0599(7) Uani 1 1 d . . . H4A H 0.1930 0.0833 0.2143 0.072 Uiso 1 1 calc R . . H4B H 0.2873 0.1022 0.2877 0.072 Uiso 1 1 calc R . . C5 C 0.3348(3) 0.2311(2) 0.19897(15) 0.0553(6) Uani 1 1 d . . . H5A H 0.4225 0.1890 0.1919 0.066 Uiso 1 1 calc R . . H5B H 0.2961 0.2510 0.1485 0.066 Uiso 1 1 calc R . . C6 C 0.3483(2) 0.3528(2) 0.24843(13) 0.0422(5) Uani 1 1 d . . . H6 H 0.4116 0.3347 0.2912 0.051 Uiso 1 1 calc R . . C7 C 0.3984(2) 0.4702(2) 0.20525(13) 0.0445(5) Uani 1 1 d . . . C8 C 0.2868(2) 0.7432(2) 0.12850(12) 0.0481(5) Uani 1 1 d . . . H8 H 0.1941 0.7465 0.1499 0.058 Uiso 1 1 calc R . . C9 C 0.2871(3) 0.6582(3) 0.05741(14) 0.0604(7) Uani 1 1 d . . . H9A H 0.2560 0.5717 0.0709 0.073 Uiso 1 1 calc R . . H9B H 0.3791 0.6515 0.0370 0.073 Uiso 1 1 calc R . . C10 C 0.1935(3) 0.7163(3) -0.00368(17) 0.0818(10) Uani 1 1 d . . . H10A H 0.0999 0.7131 0.0147 0.098 Uiso 1 1 calc R . . H10B H 0.1991 0.6649 -0.0508 0.098 Uiso 1 1 calc R . . C11 C 0.2315(3) 0.8566(3) -0.02204(16) 0.0778(9) Uani 1 1 d . . . H11A H 0.3194 0.8584 -0.0479 0.093 Uiso 1 1 calc R . . H11B H 0.1643 0.8929 -0.0573 0.093 Uiso 1 1 calc R . . C12 C 0.2382(3) 0.9390(3) 0.05038(16) 0.0751(9) Uani 1 1 d . . . H12A H 0.1475 0.9472 0.0724 0.090 Uiso 1 1 calc R . . H12B H 0.2702 1.0253 0.0369 0.090 Uiso 1 1 calc R . . C13 C 0.3338(3) 0.8795(2) 0.11041(14) 0.0555(6) Uani 1 1 d . . . H13A H 0.4263 0.8776 0.0903 0.067 Uiso 1 1 calc R . . H13B H 0.3332 0.9315 0.1574 0.067 Uiso 1 1 calc R . . C14 C 0.2204(2) 0.7130(2) 0.31930(12) 0.0441(5) Uani 1 1 d . . . H14 H 0.2788 0.7780 0.3018 0.053 Uiso 1 1 calc R . . C15 C 0.1255(2) 0.7525(2) 0.38085(12) 0.0433(5) Uani 1 1 d . . . C16 C 0.0837(3) 0.6765(2) 0.44323(13) 0.0534(6) Uani 1 1 d . . . H16 H 0.1157 0.5919 0.4486 0.064 Uiso 1 1 calc R . . C17 C -0.0053(3) 0.7277(3) 0.49685(15) 0.0647(7) Uani 1 1 d . . . H17 H -0.0344 0.6787 0.5391 0.078 Uiso 1 1 calc R . . C18 C -0.0504(3) 0.8529(3) 0.48675(17) 0.0730(8) Uani 1 1 d . . . H18 H -0.1113 0.8863 0.5231 0.088 Uiso 1 1 calc R . . C19 C 0.0743(3) 0.8782(2) 0.37825(15) 0.0574(6) Uani 1 1 d . . . H19 H 0.1035 0.9311 0.3378 0.069 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 0.0373(8) 0.0559(9) 0.0706(10) -0.0054(8) 0.0129(8) 0.0000(8) O2 0.0497(9) 0.0589(10) 0.0795(12) -0.0079(9) 0.0250(9) -0.0008(9) O3 0.0409(8) 0.0441(8) 0.0488(8) 0.0039(7) -0.0005(7) -0.0071(7) N1 0.0345(8) 0.0401(9) 0.0513(10) 0.0022(8) 0.0004(8) -0.0003(8) N2 0.0390(9) 0.0423(10) 0.0471(10) -0.0002(8) 0.0066(8) -0.0029(8) N3 0.0820(17) 0.0644(14) 0.0821(16) -0.0137(13) 0.0178(14) 0.0143(13) C1 0.0348(10) 0.0438(11) 0.0378(10) 0.0022(9) -0.0005(9) 0.0022(9) C2 0.0361(10) 0.0448(12) 0.0397(10) -0.0018(9) -0.0014(9) 0.0020(10) C3 0.0441(12) 0.0433(12) 0.0575(13) 0.0060(11) -0.0024(11) -0.0046(10) C4 0.0584(15) 0.0465(13) 0.0748(17) -0.0072(12) 0.0023(14) -0.0046(12) C5 0.0533(13) 0.0484(13) 0.0641(14) -0.0087(11) 0.0071(13) 0.0020(12) C6 0.0332(10) 0.0435(11) 0.0497(11) -0.0020(9) -0.0032(10) 0.0030(10) C7 0.0326(10) 0.0493(12) 0.0516(12) -0.0065(11) -0.0008(10) -0.0006(10) C8 0.0348(10) 0.0626(14) 0.0468(12) 0.0080(11) 0.0051(10) 0.0006(11) C9 0.0641(16) 0.0636(15) 0.0535(13) 0.0008(12) -0.0092(13) -0.0190(14) C10 0.0712(18) 0.115(3) 0.0592(15) 0.0118(18) -0.0157(15) -0.0224(19) C11 0.0687(18) 0.108(2) 0.0567(15) 0.0261(16) 0.0022(14) 0.0097(19) C12 0.0753(19) 0.0841(19) 0.0660(16) 0.0209(15) 0.0198(15) 0.0310(17) C13 0.0660(15) 0.0472(13) 0.0535(13) 0.0001(11) 0.0097(12) 0.0104(12) C14 0.0440(11) 0.0433(12) 0.0450(11) 0.0012(10) 0.0016(10) -0.0014(10) C15 0.0437(11) 0.0435(11) 0.0426(11) -0.0062(10) -0.0026(10) -0.0006(10) C16 0.0614(14) 0.0546(14) 0.0443(12) -0.0007(11) -0.0010(12) 0.0021(13) C17 0.0707(17) 0.079(2) 0.0447(12) -0.0036(13) 0.0095(13) -0.0123(16) C18 0.0647(17) 0.082(2) 0.0719(19) -0.0249(17) 0.0190(15) 0.0027(16) C19 0.0680(16) 0.0465(13) 0.0577(14) -0.0052(11) 0.0103(13) 0.0014(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 C2 1.226(2) . ? O2 C7 1.212(2) . ? O3 N2 1.400(2) . ? O3 C8 1.468(3) . ? N1 C2 1.332(3) . ? N1 C6 1.468(3) . ? N1 C3 1.471(3) . ? N2 C7 1.362(3) . ? N2 C1 1.429(3) . ? N3 C18 1.321(4) . ? N3 C19 1.326(3) . ? C1 C14 1.336(3) . ? C1 C2 1.504(3) . ? C3 C4 1.517(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.524(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.521(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.502(3) . ? C6 H6 0.9800 . ? C8 C9 1.505(3) . ? C8 C13 1.511(3) . ? C8 H8 0.9800 . ? C9 C10 1.518(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.526(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.510(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.524(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.467(3) . ? C14 H14 0.9300 . ? C15 C19 1.389(3) . ? C15 C16 1.391(3) . ? C16 C17 1.376(3) . ? C16 H16 0.9300 . ? C17 C18 1.374(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19 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 N2 O3 C8 110.32(15) . . ? C2 N1 C6 125.32(18) . . ? C2 N1 C3 122.52(16) . . ? C6 N1 C3 111.55(17) . . ? C7 N2 O3 116.76(16) . . ? C7 N2 C1 125.11(17) . . ? O3 N2 C1 116.26(15) . . ? C18 N3 C19 116.3(2) . . ? C14 C1 N2 120.83(18) . . ? C14 C1 C2 126.24(19) . . ? N2 C1 C2 112.57(17) . . ? O1 C2 N1 122.7(2) . . ? O1 C2 C1 122.08(19) . . ? N1 C2 C1 115.17(16) . . ? N1 C3 C4 103.97(17) . . ? N1 C3 H3A 111.0 . . ? C4 C3 H3A 111.0 . . ? N1 C3 H3B 111.0 . . ? C4 C3 H3B 111.0 . . ? H3A C3 H3B 109.0 . . ? C3 C4 C5 104.2(2) . . ? C3 C4 H4A 110.9 . . ? C5 C4 H4A 110.9 . . ? C3 C4 H4B 110.9 . . ? C5 C4 H4B 110.9 . . ? H4A C4 H4B 108.9 . . ? C6 C5 C4 102.73(19) . . ? C6 C5 H5A 111.2 . . ? C4 C5 H5A 111.2 . . ? C6 C5 H5B 111.2 . . ? C4 C5 H5B 111.2 . . ? H5A C5 H5B 109.1 . . ? N1 C6 C7 114.09(18) . . ? N1 C6 C5 102.19(17) . . ? C7 C6 C5 114.49(18) . . ? N1 C6 H6 108.6 . . ? C7 C6 H6 108.6 . . ? C5 C6 H6 108.6 . . ? O2 C7 N2 123.7(2) . . ? O2 C7 C6 121.7(2) . . ? N2 C7 C6 114.55(17) . . ? O3 C8 C9 112.38(19) . . ? O3 C8 C13 105.10(18) . . ? C9 C8 C13 111.85(19) . . ? O3 C8 H8 109.1 . . ? C9 C8 H8 109.1 . . ? C13 C8 H8 109.1 . . ? C8 C9 C10 109.5(2) . . ? C8 C9 H9A 109.8 . . ? C10 C9 H9A 109.8 . . ? C8 C9 H9B 109.8 . . ? C10 C9 H9B 109.8 . . ? H9A C9 H9B 108.2 . . ? C9 C10 C11 111.7(2) . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? C12 C11 C10 111.8(2) . . ? C12 C11 H11A 109.2 . . ? C10 C11 H11A 109.2 . . ? C12 C11 H11B 109.2 . . ? C10 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C11 C12 C13 111.2(2) . . ? C11 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? C11 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C8 C13 C12 109.1(2) . . ? C8 C13 H13A 109.9 . . ? C12 C13 H13A 109.9 . . ? C8 C13 H13B 109.9 . . ? C12 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C1 C14 C15 129.9(2) . . ? C1 C14 H14 115.1 . . ? C15 C14 H14 115.1 . . ? C19 C15 C16 116.3(2) . . ? C19 C15 C14 117.6(2) . . ? C16 C15 C14 126.0(2) . . ? C17 C16 C15 119.3(2) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C18 118.6(3) . . ? C16 C17 H17 120.7 . . ? C18 C17 H17 120.7 . . ? N3 C18 C17 124.2(3) . . ? N3 C18 H18 117.9 . . ? C17 C18 H18 117.9 . . ? N3 C19 C15 125.3(2) . . ? N3 C19 H19 117.3 . . ? C15 C19 H19 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 C8 O3 N2 C7 109.4(2) . . . . ? C8 O3 N2 C1 -85.32(19) . . . . ? C7 N2 C1 C14 149.7(2) . . . . ? O3 N2 C1 C14 -14.2(3) . . . . ? C7 N2 C1 C2 -36.8(3) . . . . ? O3 N2 C1 C2 159.32(16) . . . . ? C6 N1 C2 O1 176.3(2) . . . . ? C3 N1 C2 O1 6.0(3) . . . . ? C6 N1 C2 C1 -1.6(3) . . . . ? C3 N1 C2 C1 -171.97(19) . . . . ? C14 C1 C2 O1 25.6(3) . . . . ? N2 C1 C2 O1 -147.5(2) . . . . ? C14 C1 C2 N1 -156.4(2) . . . . ? N2 C1 C2 N1 30.5(2) . . . . ? C2 N1 C3 C4 172.3(2) . . . . ? C6 N1 C3 C4 0.8(2) . . . . ? N1 C3 C4 C5 -24.1(2) . . . . ? C3 C4 C5 C6 38.1(2) . . . . ? C2 N1 C6 C7 -24.4(3) . . . . ? C3 N1 C6 C7 146.83(19) . . . . ? C2 N1 C6 C5 -148.6(2) . . . . ? C3 N1 C6 C5 22.7(2) . . . . ? C4 C5 C6 N1 -36.6(2) . . . . ? C4 C5 C6 C7 -160.51(19) . . . . ? O3 N2 C7 O2 -4.2(3) . . . . ? C1 N2 C7 O2 -167.9(2) . . . . ? O3 N2 C7 C6 174.63(16) . . . . ? C1 N2 C7 C6 10.8(3) . . . . ? N1 C6 C7 O2 -161.80(19) . . . . ? C5 C6 C7 O2 -44.6(3) . . . . ? N1 C6 C7 N2 19.4(3) . . . . ? C5 C6 C7 N2 136.6(2) . . . . ? N2 O3 C8 C9 -70.9(2) . . . . ? N2 O3 C8 C13 167.23(16) . . . . ? O3 C8 C9 C10 -177.07(19) . . . . ? C13 C8 C9 C10 -59.1(3) . . . . ? C8 C9 C10 C11 54.8(3) . . . . ? C9 C10 C11 C12 -53.3(3) . . . . ? C10 C11 C12 C13 54.2(3) . . . . ? O3 C8 C13 C12 -177.78(18) . . . . ? C9 C8 C13 C12 60.0(3) . . . . ? C11 C12 C13 C8 -56.7(3) . . . . ? N2 C1 C14 C15 176.5(2) . . . . ? C2 C1 C14 C15 3.9(4) . . . . ? C1 C14 C15 C19 -144.8(2) . . . . ? C1 C14 C15 C16 36.8(4) . . . . ? C19 C15 C16 C17 1.1(3) . . . . ? C14 C15 C16 C17 179.4(2) . . . . ? C15 C16 C17 C18 0.1(4) . . . . ? C19 N3 C18 C17 -0.1(4) . . . . ? C16 C17 C18 N3 -0.6(4) . . . . ? C18 N3 C19 C15 1.5(4) . . . . ? C16 C15 C19 N3 -2.0(4) . . . . ? C14 C15 C19 N3 179.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.115 _refine_diff_density_min -0.129 _refine_diff_density_rms 0.029