# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/477 data_global _publ_contact_author ; Prof. Christopher S. Frampton Department of Chemistry Roche Discovery Welwyn Welwyn Garden City Hertfordshire AL7 3AY U.K. ; _publ_contact_author_phone '44(1707)366272' _publ_contact_author_fax '44(1707)366907' _publ_contact_author_email 'christopher.frampton@roche.com' _publ_section_title ; Synthesis of C2-Symmetric Analogues of 4-(Pyrrolidino)pyridine: A Novel Class of Chiral Nucleophilic Catalysts Paper Reference: B004704J ; loop_ _publ_author_name _publ_author_address 'Spivey, Alan C.' ; Department of Chemistry University of Sheffield Brook Hill Sheffield S3 7HF U.K. ; 'Maddaford, Adrian' ; Department of Chemistry University of Sheffield Brook Hill Sheffield S3 7HF U.K. ; 'Fekner, Tomasz' ; Department of Chemistry University of Sheffield Brook Hill Sheffield S3 7HF U.K. ; 'Redgrave, Alison' ; Glaxowellcome Medicines Research Centre Gunnels Wood Road Stevenage Hertfordshire SG1 2NY U.K. ; 'Frampton, Christopher S.' ; Department of Chemistry Roche Discovery Welwyn Welwyn Garden City Hertfordshire AL7 3AY U.K. ; _publ_section_experimental ; The data collection nominally covered a sphere of reciprocal space by a combination of four sets of exposures; each set had a different \f angle for the crystal, 0, 90, 180 and 270\% repectively. Each exposure covered 0.3\% in \w with a 30 second correlated frame time. A total of 640, 470, 640, 470 frames were accumalated in each \w sweep respectively. The crystal to detector distance was 4.935 cm. Coverage of the unique set was 95.0% to 29.13\% in \q, (0.73\%A) and 100.0% complete to 26.37\% in \q, (0.80\%A). Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analyzing the duplicate reflections, a further 50 frames of data were collected at positive 2\q to improve cell refinement statistics. the data were trucatated to 0.80\%A for structure refinement. ; _publ_section_exptl_refinement ; Hydrogen atoms were placed geometrically and refined with a riding model with U~iso~ allowed to refine freely. Area detector scaling and absorption corrections were performed by sadabs. This correction was used to scale the frames of data and to correct for absorption of the primary beam by the crystal support using the method of Blessing (1995). A correction for absorption of the primary beam by the crystal was not applied and as such no transmission factors are quoted. ; _publ_section_references ; Blessing R.H. (1995). Acta Cryst., A51, 33-38. Bruker AXS (1997). SMART, SAINT and SADABS area-detector control and integration software. Bruker AXS Inc., Madison, WI 53719, U.S.A. Sheldrick, G.M. (1997). SHELXTL V5.10. Bruker AXS Inc., Madison, WI 53179, U.S.A. ; data_csf93s _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'CSF93/Spivey/AN-Wafers/4999/12-3-99.' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H24 N2 O2' _chemical_formula_weight 360.44 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 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 5.3697(3) _cell_length_b 16.3416(14) _cell_length_c 21.7265(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1906.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 5943 _cell_measurement_theta_min 1.56 _cell_measurement_theta_max 26.35 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.080 _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 123(1) _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 AXS 1K SMART CCD area detector' _diffrn_measurement_method 'narrow frame omega scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 'see text' _diffrn_standards_decay_% none _diffrn_reflns_number 19928 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 26.35 _reflns_number_total 3905 _reflns_number_gt 3531 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5 (Bruker AXS, 1998)' _computing_cell_refinement 'SMART V5 & SAINT V5 (Bruker AXS,1998)' _computing_data_reduction 'SAINT V5 (Bruker AXS, 1998)' _computing_structure_solution 'SHELXTL V5.10 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL V5.10 (Sheldrick, 1998)' _computing_molecular_graphics 'SHELXTL V5.10 (Sheldrick, 1998)' _computing_publication_material 'SHELXTL V5.10 (Sheldrick, 1998)' _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^)+(0.0590P)^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 mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.9(9) #'Absolute structure not determined' _refine_ls_number_reflns 3905 _refine_ls_number_parameters 268 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0806 _refine_ls_wR_factor_gt 0.0789 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 0.83451(16) 0.42483(6) 0.66137(4) 0.0283(2) Uani 1 1 d . . . O2 O 0.22580(17) 0.39597(5) 0.93253(4) 0.0276(2) Uani 1 1 d . . . N1 N 0.5514(2) 0.49703(6) 0.80494(4) 0.0234(2) Uani 1 1 d . . . N2 N 0.6204(2) 0.75238(6) 0.82804(5) 0.0330(3) Uani 1 1 d . . . C1 C 0.7109(2) 0.44832(8) 0.76379(6) 0.0239(3) Uani 1 1 d . . . H1A H 0.8900 0.4627 0.7701 0.022(3) Uiso 1 1 calc R . . C2 C 0.6609(3) 0.36069(8) 0.78507(6) 0.0279(3) Uani 1 1 d . . . H2A H 0.7700 0.3455 0.8200 0.029(4) Uiso 1 1 calc R . . H2B H 0.6858 0.3212 0.7511 0.037(4) Uiso 1 1 calc R . . C3 C 0.3873(3) 0.36410(7) 0.80483(6) 0.0263(3) Uani 1 1 d . . . H3A H 0.2750 0.3622 0.7687 0.027(4) Uiso 1 1 calc R . . H3B H 0.3458 0.3183 0.8329 0.047(5) Uiso 1 1 calc R . . C4 C 0.3685(2) 0.44652(7) 0.83797(5) 0.0230(3) Uani 1 1 d . . . H4A H 0.1977 0.4699 0.8328 0.016(3) Uiso 1 1 calc R . . C5 C 0.5702(2) 0.58013(8) 0.81121(5) 0.0226(3) Uani 1 1 d . . . C6 C 0.3955(2) 0.62600(7) 0.84482(5) 0.0240(3) Uani 1 1 d . . . H6A H 0.2556 0.5998 0.8629 0.023(3) Uiso 1 1 calc R . . C7 C 0.4281(3) 0.70950(8) 0.85149(6) 0.0289(3) Uani 1 1 d . . . H7A H 0.3061 0.7388 0.8743 0.029(4) Uiso 1 1 calc R . . C8 C 0.7833(3) 0.70815(8) 0.79557(6) 0.0319(3) Uani 1 1 d . . . H8A H 0.9213 0.7363 0.7782 0.027(4) Uiso 1 1 calc R . . C9 C 0.7678(2) 0.62478(8) 0.78511(6) 0.0273(3) Uani 1 1 d . . . H9A H 0.8894 0.5980 0.7606 0.037(4) Uiso 1 1 calc R . . C10 C 0.6372(2) 0.46119(8) 0.69639(5) 0.0250(3) Uani 1 1 d . . . H10A H 0.4764 0.4341 0.6873 0.031(4) Uiso 1 1 calc R . . H10B H 0.6221 0.5202 0.6869 0.019(3) Uiso 1 1 calc R . . C11 C 0.7889(2) 0.41073(7) 0.59994(6) 0.0223(3) Uani 1 1 d . . . C12 C 0.5870(2) 0.44274(8) 0.56792(6) 0.0255(3) Uani 1 1 d . . . H12A H 0.4713 0.4777 0.5879 0.027(4) Uiso 1 1 calc R . . C13 C 0.5570(3) 0.42272(8) 0.50598(6) 0.0276(3) Uani 1 1 d . . . H13A H 0.4192 0.4442 0.4838 0.034(4) Uiso 1 1 calc R . . C14 C 0.7246(3) 0.37202(8) 0.47631(6) 0.0283(3) Uani 1 1 d . . . H14A H 0.7010 0.3580 0.4343 0.029(4) Uiso 1 1 calc R . . C15 C 0.9283(3) 0.34169(8) 0.50871(6) 0.0278(3) Uani 1 1 d . . . H15A H 1.0453 0.3074 0.4884 0.038(4) Uiso 1 1 calc R . . C16 C 0.9622(2) 0.36101(7) 0.57021(6) 0.0250(3) Uani 1 1 d . . . H16A H 1.1024 0.3405 0.5920 0.025(4) Uiso 1 1 calc R . . C17 C 0.4317(2) 0.43926(7) 0.90639(5) 0.0232(3) Uani 1 1 d . . . H17A H 0.5887 0.4085 0.9124 0.025(3) Uiso 1 1 calc R . . H17B H 0.4492 0.4940 0.9254 0.021(3) Uiso 1 1 calc R . . C18 C 0.2300(2) 0.37829(7) 0.99435(6) 0.0233(3) Uani 1 1 d . . . C19 C 0.0355(3) 0.32902(8) 1.01482(6) 0.0300(3) Uani 1 1 d . . . H19A H -0.0856 0.3093 0.9866 0.037(4) Uiso 1 1 calc R . . C20 C 0.0200(3) 0.30899(9) 1.07662(7) 0.0360(3) Uani 1 1 d . . . H20A H -0.1127 0.2754 1.0907 0.038(4) Uiso 1 1 calc R . . C21 C 0.1962(3) 0.33741(9) 1.11815(7) 0.0371(3) Uani 1 1 d . . . H21A H 0.1844 0.3236 1.1605 0.038(4) Uiso 1 1 calc R . . C22 C 0.3893(3) 0.38608(9) 1.09718(6) 0.0339(3) Uani 1 1 d . . . H22A H 0.5102 0.4056 1.1255 0.039(4) Uiso 1 1 calc R . . C23 C 0.4095(3) 0.40707(8) 1.03503(6) 0.0273(3) Uani 1 1 d . . . H23A H 0.5430 0.4403 1.0209 0.030(4) 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 0.0257(5) 0.0387(5) 0.0205(4) -0.0025(4) 0.0002(4) 0.0065(4) O2 0.0272(5) 0.0313(5) 0.0243(5) 0.0015(4) -0.0005(4) -0.0070(4) N1 0.0293(6) 0.0222(5) 0.0187(5) -0.0003(4) 0.0029(4) 0.0006(4) N2 0.0400(7) 0.0227(5) 0.0362(6) 0.0033(5) -0.0110(5) 0.0007(5) C1 0.0255(6) 0.0255(6) 0.0208(6) -0.0025(5) -0.0012(5) 0.0033(5) C2 0.0359(7) 0.0248(6) 0.0229(6) -0.0030(5) -0.0036(5) 0.0040(6) C3 0.0357(7) 0.0218(6) 0.0214(6) -0.0016(5) -0.0036(5) -0.0013(6) C4 0.0246(6) 0.0225(6) 0.0219(6) -0.0002(5) -0.0015(5) -0.0017(5) C5 0.0266(6) 0.0241(6) 0.0171(5) 0.0016(5) -0.0073(5) 0.0000(5) C6 0.0266(6) 0.0250(6) 0.0204(6) 0.0011(5) -0.0042(5) 0.0012(5) C7 0.0349(7) 0.0257(6) 0.0262(6) -0.0004(5) -0.0086(6) 0.0055(6) C8 0.0309(7) 0.0294(7) 0.0353(8) 0.0091(6) -0.0074(6) -0.0049(6) C9 0.0278(7) 0.0288(7) 0.0254(6) 0.0042(5) -0.0022(5) 0.0013(6) C10 0.0257(6) 0.0286(6) 0.0207(6) -0.0021(5) 0.0013(5) 0.0049(5) C11 0.0250(6) 0.0223(6) 0.0196(6) 0.0016(5) 0.0014(5) -0.0031(5) C12 0.0258(6) 0.0278(6) 0.0228(6) -0.0021(5) 0.0035(5) 0.0027(5) C13 0.0265(6) 0.0316(6) 0.0246(6) 0.0019(5) -0.0021(6) 0.0000(5) C14 0.0340(7) 0.0300(7) 0.0210(6) -0.0008(5) 0.0033(5) -0.0046(6) C15 0.0304(7) 0.0265(6) 0.0264(6) 0.0004(5) 0.0089(6) 0.0014(6) C16 0.0229(6) 0.0252(6) 0.0268(6) 0.0047(5) 0.0025(5) 0.0009(5) C17 0.0244(6) 0.0232(6) 0.0220(6) 0.0003(5) 0.0001(5) -0.0030(5) C18 0.0250(6) 0.0199(6) 0.0250(6) 0.0011(5) 0.0026(5) 0.0035(5) C19 0.0277(7) 0.0274(7) 0.0349(7) 0.0045(6) 0.0005(6) 0.0002(5) C20 0.0359(8) 0.0329(7) 0.0392(8) 0.0116(6) 0.0097(6) 0.0006(6) C21 0.0482(9) 0.0365(7) 0.0266(7) 0.0100(6) 0.0078(6) 0.0073(7) C22 0.0390(8) 0.0360(7) 0.0269(7) 0.0002(6) -0.0017(6) 0.0035(7) C23 0.0286(7) 0.0270(6) 0.0263(6) 0.0012(5) 0.0021(6) 0.0005(6) _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 C11 1.3763(15) . yes O1 C10 1.4332(15) . yes O2 C18 1.3741(15) . yes O2 C17 1.4300(15) . yes N1 C5 1.3684(16) . yes N1 C4 1.4701(16) . yes N1 C1 1.4717(16) . yes N2 C8 1.3360(19) . yes N2 C7 1.3479(18) . yes C1 C2 1.5284(18) . yes C1 C10 1.5314(16) . yes C2 C3 1.532(2) . yes C3 C4 1.5306(16) . yes C4 C17 1.5294(16) . yes C5 C6 1.4053(17) . yes C5 C9 1.4074(18) . yes C6 C7 1.3833(18) . yes C8 C9 1.384(2) . yes C11 C12 1.3902(18) . yes C11 C16 1.3941(17) . yes C12 C13 1.3944(17) . yes C13 C14 1.3827(19) . yes C14 C15 1.3921(19) . yes C15 C16 1.3848(18) . yes C18 C23 1.3897(19) . yes C18 C19 1.3916(18) . yes C19 C20 1.3846(19) . yes C20 C21 1.387(2) . yes C21 C22 1.384(2) . yes C22 C23 1.3974(18) . yes C1 H1A 1.0000 . no C2 H2A 0.9900 . no C2 H2B 0.9900 . no C3 H3A 0.9900 . no C3 H3B 0.9900 . no C4 H4A 1.0000 . no C6 H6A 0.9500 . no C7 H7A 0.9500 . no C8 H8A 0.9500 . no C9 H9A 0.9500 . no C10 H10A 0.9900 . no C10 H10B 0.9900 . no C12 H12A 0.9500 . no C13 H13A 0.9500 . no C14 H14A 0.9500 . no C15 H15A 0.9500 . no C16 H16A 0.9500 . no C17 H17A 0.9900 . no C17 H17B 0.9900 . no C19 H19A 0.9500 . no C20 H20A 0.9500 . no C21 H21A 0.9500 . no C22 H22A 0.9500 . no C23 H23A 0.9500 . no 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 C11 O1 C10 116.91(9) . . yes C18 O2 C17 118.65(9) . . yes C5 N1 C4 123.90(10) . . yes C5 N1 C1 123.68(10) . . yes C4 N1 C1 112.42(10) . . yes C8 N2 C7 114.82(11) . . yes N1 C1 C2 102.77(10) . . yes N1 C1 C10 110.89(10) . . yes C2 C1 C10 111.88(10) . . yes C1 C2 C3 102.65(10) . . yes C4 C3 C2 103.11(11) . . yes N1 C4 C17 111.71(10) . . yes N1 C4 C3 102.74(10) . . yes C17 C4 C3 111.99(10) . . yes N1 C5 C6 122.14(11) . . yes N1 C5 C9 122.00(12) . . yes C6 C5 C9 115.85(11) . . yes C7 C6 C5 119.74(12) . . yes N2 C7 C6 124.77(13) . . yes N2 C8 C9 125.46(13) . . yes C8 C9 C5 119.32(13) . . yes O1 C10 C1 105.07(10) . . yes O1 C11 C12 124.12(11) . . yes O1 C11 C16 115.34(11) . . yes C12 C11 C16 120.53(11) . . yes C11 C12 C13 119.00(12) . . yes C14 C13 C12 121.01(12) . . yes C13 C14 C15 119.28(12) . . yes C16 C15 C14 120.66(12) . . yes C15 C16 C11 119.49(12) . . yes O2 C17 C4 104.65(9) . . yes O2 C18 C23 124.18(11) . . yes O2 C18 C19 114.94(11) . . yes C23 C18 C19 120.87(12) . . yes C20 C19 C18 119.46(13) . . yes C19 C20 C21 120.69(13) . . yes C22 C21 C20 119.29(13) . . yes C21 C22 C23 121.16(13) . . yes C18 C23 C22 118.53(12) . . yes N1 C1 H1A 110.4 . . no C2 C1 H1A 110.4 . . no C10 C1 H1A 110.4 . . no C1 C2 H2A 111.2 . . no C3 C2 H2A 111.2 . . no C1 C2 H2B 111.2 . . no C3 C2 H2B 111.2 . . no H2A C2 H2B 109.1 . . no C4 C3 H3A 111.1 . . no C2 C3 H3A 111.1 . . no C4 C3 H3B 111.1 . . no C2 C3 H3B 111.1 . . no H3A C3 H3B 109.1 . . no N1 C4 H4A 110.1 . . no C17 C4 H4A 110.1 . . no C3 C4 H4A 110.1 . . no C7 C6 H6A 120.1 . . no C5 C6 H6A 120.1 . . no N2 C7 H7A 117.6 . . no C6 C7 H7A 117.6 . . no N2 C8 H8A 117.3 . . no C9 C8 H8A 117.3 . . no C8 C9 H9A 120.3 . . no C5 C9 H9A 120.3 . . no O1 C10 H10A 110.7 . . no C1 C10 H10A 110.7 . . no O1 C10 H10B 110.7 . . no C1 C10 H10B 110.7 . . no H10A C10 H10B 108.8 . . no C11 C12 H12A 120.5 . . no C13 C12 H12A 120.5 . . no C14 C13 H13A 119.5 . . no C12 C13 H13A 119.5 . . no C13 C14 H14A 120.4 . . no C15 C14 H14A 120.4 . . no C16 C15 H15A 119.7 . . no C14 C15 H15A 119.7 . . no C15 C16 H16A 120.3 . . no C11 C16 H16A 120.3 . . no O2 C17 H17A 110.8 . . no C4 C17 H17A 110.8 . . no O2 C17 H17B 110.8 . . no C4 C17 H17B 110.8 . . no H17A C17 H17B 108.9 . . no C20 C19 H19A 120.3 . . no C18 C19 H19A 120.3 . . no C19 C20 H20A 119.7 . . no C21 C20 H20A 119.7 . . no C22 C21 H21A 120.4 . . no C20 C21 H21A 120.4 . . no C21 C22 H22A 119.4 . . no C23 C22 H22A 119.4 . . no C18 C23 H23A 120.7 . . no C22 C23 H23A 120.7 . . no 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 C5 N1 C1 C2 166.72(11) . . . . no C4 N1 C1 C2 -13.88(13) . . . . no C5 N1 C1 C10 -73.58(14) . . . . no C4 N1 C1 C10 105.82(11) . . . . no N1 C1 C2 C3 33.21(12) . . . . no C10 C1 C2 C3 -85.80(12) . . . . no C1 C2 C3 C4 -40.71(12) . . . . no C5 N1 C4 C17 -71.68(14) . . . . no C1 N1 C4 C17 108.92(11) . . . . no C5 N1 C4 C3 168.11(11) . . . . no C1 N1 C4 C3 -11.29(13) . . . . no C2 C3 C4 N1 31.80(12) . . . . no C2 C3 C4 C17 -88.22(12) . . . . no C4 N1 C5 C6 -7.54(18) . . . . no C1 N1 C5 C6 171.79(11) . . . . no C4 N1 C5 C9 171.53(11) . . . . no C1 N1 C5 C9 -9.15(18) . . . . no N1 C5 C6 C7 177.75(11) . . . . no C9 C5 C6 C7 -1.36(17) . . . . no C8 N2 C7 C6 1.17(19) . . . . no C5 C6 C7 N2 -0.39(19) . . . . no C7 N2 C8 C9 -0.15(19) . . . . no N2 C8 C9 C5 -1.6(2) . . . . no N1 C5 C9 C8 -176.85(12) . . . . no C6 C5 C9 C8 2.27(17) . . . . no C11 O1 C10 C1 165.23(10) . . . . no N1 C1 C10 O1 168.48(10) . . . . no C2 C1 C10 O1 -77.44(12) . . . . no C10 O1 C11 C12 12.52(17) . . . . no C10 O1 C11 C16 -167.65(10) . . . . no O1 C11 C12 C13 -178.58(12) . . . . no C16 C11 C12 C13 1.59(19) . . . . no C11 C12 C13 C14 -0.2(2) . . . . no C12 C13 C14 C15 -1.01(19) . . . . no C13 C14 C15 C16 0.80(19) . . . . no C14 C15 C16 C11 0.59(19) . . . . no O1 C11 C16 C15 178.36(11) . . . . no C12 C11 C16 C15 -1.80(18) . . . . no C18 O2 C17 C4 178.77(10) . . . . no N1 C4 C17 O2 174.39(9) . . . . no C3 C4 C17 O2 -70.99(12) . . . . no C17 O2 C18 C23 7.06(17) . . . . no C17 O2 C18 C19 -173.78(11) . . . . no O2 C18 C19 C20 -178.72(12) . . . . no C23 C18 C19 C20 0.5(2) . . . . no C18 C19 C20 C21 -0.1(2) . . . . no C19 C20 C21 C22 -0.2(2) . . . . no C20 C21 C22 C23 0.1(2) . . . . no O2 C18 C23 C22 178.53(12) . . . . no C19 C18 C23 C22 -0.58(18) . . . . no C21 C22 C23 C18 0.3(2) . . . . no _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.154 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.033 #===END