# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Robert A. Stockman' 'David L. Hughes' 'Martin Rejzek' _publ_contact_author_name 'Dr Robert A. Stockman' _publ_contact_author_address ; School of Chemical Sciences and Pharmacy University of East Anglia Norwich NR4 7TJ UNITED KINGDOM ; _publ_contact_author_email R.STOCKMAN@UEA.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Combining Two-Directional Synthesis and Tandem Reactions, Part 5: An Efficient Strategy for the Total Syntheses of (±)-Hippodamine and (±)-epi-Hippodamine ; data_martinr3 _database_code_depnum_ccdc_archive 'CCDC 248861' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H23 N O' _chemical_formula_structural 'tricyclic C13 H23 N O' _chemical_formula_sum 'C13 H23 N O' _chemical_formula_weight 209.32 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.766(3) _cell_length_b 9.337(2) _cell_length_c 13.7672(17) _cell_angle_alpha 90.00 _cell_angle_beta 102.381(17) _cell_angle_gamma 90.00 _cell_volume 1226.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 12 _exptl_crystal_description plate _exptl_crystal_colour 'clear, colourless' _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.134 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type psi-scans _exptl_absorpt_correction_T_min 0.358 _exptl_absorpt_correction_T_max 0.401 _exptl_absorpt_process_details 'EMPABS, (Sheldrick et al, 1977)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type Mo-K\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius CAD4 diffractometer' _diffrn_measurement_method 'scintillation counter; \w/\q scans' _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '10000 s' _diffrn_standards_decay_% 5.7 _diffrn_reflns_number 2146 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2146 _reflns_number_gt 1263 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'CAD4/EXPRESS (Enraf-Nonius, 1992)' _computing_cell_refinement 'CAD4/EXPRESS (Enraf-Nonius, 1992)' _computing_data_reduction 'CAD4 (Hursthouse, 1976)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson, 1971)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0645P)^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_extinction_coef ? _refine_ls_number_reflns 2146 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0814 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1362 _refine_ls_wR_factor_gt 0.1114 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 N N 0.68779(14) 0.68193(16) 0.77631(10) 0.0309(4) Uani 1 1 d . . . C1 C 0.61971(18) 0.57015(19) 0.82639(13) 0.0336(4) Uani 1 1 d . . . H1 H 0.6484 0.4755 0.8073 0.040 Uiso 1 1 calc R . . C2 C 0.46147(19) 0.5844(2) 0.79252(14) 0.0367(5) Uani 1 1 d . . . H2A H 0.4172 0.5106 0.8247 0.044 Uiso 1 1 calc R . . H2B H 0.4332 0.6764 0.8144 0.044 Uiso 1 1 calc R . . C3 C 0.40806(18) 0.57254(19) 0.68084(13) 0.0356(5) Uani 1 1 d . . . O3 O 0.43293(14) 0.43125(14) 0.64701(11) 0.0413(4) Uani 1 1 d . . . H3O H 0.388(2) 0.381(2) 0.6752(16) 0.050(7) Uiso 1 1 d . . . C31 C 0.2518(2) 0.6055(2) 0.65235(17) 0.0519(6) Uani 1 1 d . . . H31A H 0.2015 0.5393 0.6851 0.078 Uiso 1 1 calc R . . H31B H 0.2199 0.5967 0.5816 0.078 Uiso 1 1 calc R . . H31C H 0.2355 0.7014 0.6724 0.078 Uiso 1 1 calc R . . C4 C 0.49061(19) 0.6754(2) 0.62974(14) 0.0361(5) Uani 1 1 d . . . H4A H 0.4592 0.7722 0.6386 0.043 Uiso 1 1 calc R . . H4B H 0.4686 0.6552 0.5590 0.043 Uiso 1 1 calc R . . C5 C 0.64907(18) 0.66996(19) 0.66638(13) 0.0331(4) Uani 1 1 d . . . H5 H 0.6856 0.7565 0.6405 0.040 Uiso 1 1 calc R . . C6 C 0.7188(2) 0.5436(2) 0.62509(14) 0.0431(5) Uani 1 1 d . . . H6A H 0.6842 0.4546 0.6472 0.052 Uiso 1 1 calc R . . H6B H 0.6939 0.5455 0.5530 0.052 Uiso 1 1 calc R . . C7 C 0.8770(2) 0.5492(2) 0.65934(15) 0.0507(6) Uani 1 1 d . . . H7A H 0.9133 0.6317 0.6302 0.061 Uiso 1 1 calc R . . H7B H 0.9181 0.4638 0.6373 0.061 Uiso 1 1 calc R . . C8 C 0.9171(2) 0.5593(2) 0.77197(15) 0.0476(5) Uani 1 1 d . . . H8A H 1.0178 0.5712 0.7929 0.057 Uiso 1 1 calc R . . H8B H 0.8915 0.4711 0.8008 0.057 Uiso 1 1 calc R . . C9 C 0.84302(18) 0.6855(2) 0.80960(14) 0.0384(5) Uani 1 1 d . . . H9 H 0.8748 0.7720 0.7807 0.046 Uiso 1 1 calc R . . C10 C 0.8841(2) 0.7035(2) 0.92177(14) 0.0461(6) Uani 1 1 d . . . H10A H 0.9854 0.7007 0.9428 0.055 Uiso 1 1 calc R . . H10B H 0.8524 0.7962 0.9398 0.055 Uiso 1 1 calc R . . C11 C 0.8211(2) 0.5871(2) 0.97550(15) 0.0491(6) Uani 1 1 d . . . H11A H 0.8595 0.4947 0.9631 0.059 Uiso 1 1 calc R . . H11B H 0.8442 0.6048 1.0466 0.059 Uiso 1 1 calc R . . C12 C 0.6632(2) 0.5860(2) 0.93857(14) 0.0438(5) Uani 1 1 d . . . H12A H 0.6248 0.6745 0.9583 0.053 Uiso 1 1 calc R . . H12B H 0.6239 0.5075 0.9698 0.053 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 N 0.0324(9) 0.0269(8) 0.0329(8) 0.0016(6) 0.0063(7) 0.0001(6) C1 0.0410(11) 0.0238(9) 0.0383(11) 0.0013(8) 0.0137(8) -0.0016(8) C2 0.0401(11) 0.0283(10) 0.0454(11) -0.0012(8) 0.0174(9) -0.0005(8) C3 0.0363(11) 0.0236(10) 0.0479(12) -0.0054(8) 0.0114(9) 0.0011(8) O3 0.0490(9) 0.0250(7) 0.0527(9) -0.0054(6) 0.0173(7) -0.0057(6) C31 0.0404(12) 0.0467(13) 0.0683(15) -0.0070(11) 0.0109(11) -0.0013(10) C4 0.0404(11) 0.0253(9) 0.0410(11) 0.0003(8) 0.0055(9) -0.0008(8) C5 0.0369(10) 0.0293(10) 0.0336(10) 0.0049(8) 0.0085(8) -0.0011(8) C6 0.0459(12) 0.0461(13) 0.0404(11) -0.0041(9) 0.0159(9) 0.0029(9) C7 0.0456(13) 0.0573(14) 0.0532(13) -0.0030(11) 0.0197(10) 0.0106(11) C8 0.0342(11) 0.0552(14) 0.0543(13) 0.0036(11) 0.0119(9) 0.0092(10) C9 0.0345(11) 0.0355(11) 0.0450(12) 0.0033(9) 0.0080(9) -0.0005(8) C10 0.0435(12) 0.0439(13) 0.0467(13) -0.0028(9) 0.0001(10) 0.0023(9) C11 0.0583(14) 0.0497(13) 0.0369(11) 0.0013(10) 0.0044(10) 0.0096(11) C12 0.0536(13) 0.0419(12) 0.0384(11) 0.0035(9) 0.0149(9) 0.0024(10) _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 N C5 1.484(2) . ? N C1 1.484(2) . ? N C9 1.487(2) . ? C1 C12 1.519(2) . ? C1 C2 1.521(2) . ? C1 H1 0.9800 . ? C2 C3 1.518(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O3 1.437(2) . ? C3 C4 1.520(3) . ? C3 C31 1.524(3) . ? O3 H3O 0.80(2) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C4 C5 1.522(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.531(3) . ? C5 H5 0.9800 . ? C6 C7 1.517(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.519(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.530(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.519(3) . ? C9 H9 0.9800 . ? C10 C11 1.517(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.516(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? 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 C5 N C1 112.29(13) . . ? C5 N C9 109.64(13) . . ? C1 N C9 113.65(13) . . ? N C1 C12 110.38(14) . . ? N C1 C2 108.84(14) . . ? C12 C1 C2 110.33(15) . . ? N C1 H1 109.1 . . ? C12 C1 H1 109.1 . . ? C2 C1 H1 109.1 . . ? C3 C2 C1 114.20(15) . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? O3 C3 C2 110.49(14) . . ? O3 C3 C4 106.67(15) . . ? C2 C3 C4 108.75(14) . . ? O3 C3 C31 109.38(15) . . ? C2 C3 C31 110.71(15) . . ? C4 C3 C31 110.76(15) . . ? C3 O3 H3O 103.8(16) . . ? C3 C31 H31A 109.5 . . ? C3 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C3 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C3 C4 C5 115.33(15) . . ? C3 C4 H4A 108.4 . . ? C5 C4 H4A 108.4 . . ? C3 C4 H4B 108.4 . . ? C5 C4 H4B 108.4 . . ? H4A C4 H4B 107.5 . . ? N C5 C4 110.74(14) . . ? N C5 C6 113.60(14) . . ? C4 C5 C6 113.84(15) . . ? N C5 H5 106.0 . . ? C4 C5 H5 106.0 . . ? C6 C5 H5 106.0 . . ? C7 C6 C5 111.25(16) . . ? C7 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? C7 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C6 C7 C8 109.97(15) . . ? 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 . . ? C7 C8 C9 110.88(16) . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? N C9 C10 110.18(15) . . ? N C9 C8 113.77(15) . . ? C10 C9 C8 112.86(16) . . ? N C9 H9 106.5 . . ? C10 C9 H9 106.5 . . ? C8 C9 H9 106.5 . . ? C11 C10 C9 111.74(16) . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? C12 C11 C10 109.30(16) . . ? C12 C11 H11A 109.8 . . ? C10 C11 H11A 109.8 . . ? C12 C11 H11B 109.8 . . ? C10 C11 H11B 109.8 . . ? H11A C11 H11B 108.3 . . ? C11 C12 C1 112.60(15) . . ? C11 C12 H12A 109.1 . . ? C1 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C1 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? 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 N C1 C12 179.58(14) . . . . ? C9 N C1 C12 54.40(18) . . . . ? C5 N C1 C2 -59.19(18) . . . . ? C9 N C1 C2 175.63(14) . . . . ? N C1 C2 C3 57.76(19) . . . . ? C12 C1 C2 C3 179.02(15) . . . . ? C1 C2 C3 O3 65.40(19) . . . . ? C1 C2 C3 C4 -51.4(2) . . . . ? C1 C2 C3 C31 -173.27(15) . . . . ? O3 C3 C4 C5 -71.36(19) . . . . ? C2 C3 C4 C5 47.8(2) . . . . ? C31 C3 C4 C5 169.69(16) . . . . ? C1 N C5 C4 56.18(18) . . . . ? C9 N C5 C4 -176.47(14) . . . . ? C1 N C5 C6 -73.40(18) . . . . ? C9 N C5 C6 53.95(19) . . . . ? C3 C4 C5 N -51.0(2) . . . . ? C3 C4 C5 C6 78.4(2) . . . . ? N C5 C6 C7 -55.4(2) . . . . ? C4 C5 C6 C7 176.57(16) . . . . ? C5 C6 C7 C8 54.2(2) . . . . ? C6 C7 C8 C9 -54.2(2) . . . . ? C5 N C9 C10 177.85(15) . . . . ? C1 N C9 C10 -55.57(19) . . . . ? C5 N C9 C8 -54.27(19) . . . . ? C1 N C9 C8 72.31(19) . . . . ? C7 C8 C9 N 55.7(2) . . . . ? C7 C8 C9 C10 -177.82(16) . . . . ? N C9 C10 C11 56.1(2) . . . . ? C8 C9 C10 C11 -72.3(2) . . . . ? C9 C10 C11 C12 -55.9(2) . . . . ? C10 C11 C12 C1 55.1(2) . . . . ? N C1 C12 C11 -54.1(2) . . . . ? C2 C1 C12 C11 -174.45(16) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.150 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.042 # # CIF for compound 22 of the paper: # # Combining two directional sythesis and tandem reactions, part 5: an #efficient strategy # for the total sytheses of (+/-)-hippodamine and (+/-)-epi-hippodamine # by M. Rejzek, R.A. Stockman and D.L. Hughes # data_martinr1 _database_code_depnum_ccdc_archive 'CCDC 248862' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H23 N O' _chemical_formula_structural 'a hippodamine derivative' _chemical_formula_sum 'C13 H23 N O' _chemical_formula_weight 209.32 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 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 7.660(2) _cell_length_b 14.610(3) _cell_length_c 10.367(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.13(3) _cell_angle_gamma 90.00 _cell_volume 1160.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 140(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'tapered rectangular prism' _exptl_crystal_colour 'clear, colourless,' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type 'not applied' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku R-Axis-IIc' _diffrn_measurement_method 'image-plate oscillation photos' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6714 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 25.36 _reflns_number_total 2043 _reflns_number_gt 1851 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'MSC R-Axis-II control software' _computing_cell_refinement 'DENZO/CELL (Otwinowski and Minor, 1985)' _computing_data_reduction 'DENZO, SCALEPACK (Otwinowski and Minor, 1985)' _computing_structure_solution 'SHELXS (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson, 1971)' _computing_publication_material 'SHELXL (Sheldrick, 1997)' _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^)+(0.0384P)^2^+0.3841P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2043 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1034 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 N N 0.57163(12) 0.63129(6) 0.25152(9) 0.0157(2) Uani 1 1 d . . . C1 C 0.43476(16) 0.77877(8) 0.41834(11) 0.0215(3) Uani 1 1 d . . . H1 H 0.4606 0.8435 0.4348 0.026 Uiso 1 1 calc R . . C2 C 0.38783(16) 0.77035(8) 0.27380(11) 0.0218(3) Uani 1 1 d . . . H2A H 0.2696 0.7926 0.2600 0.026 Uiso 1 1 calc R . . H2B H 0.4649 0.8100 0.2261 0.026 Uiso 1 1 calc R . . C3 C 0.39976(14) 0.67323(8) 0.21723(11) 0.0180(3) Uani 1 1 d . . . H3 H 0.3993 0.6811 0.1233 0.022 Uiso 1 1 calc R . . C4 C 0.24385(15) 0.61076(8) 0.24552(12) 0.0217(3) Uani 1 1 d . . . H4A H 0.2371 0.6009 0.3378 0.026 Uiso 1 1 calc R . . H4B H 0.1366 0.6402 0.2165 0.026 Uiso 1 1 calc R . . C5 C 0.26273(16) 0.51842(9) 0.17687(13) 0.0263(3) Uani 1 1 d . . . H5A H 0.1687 0.4780 0.2016 0.032 Uiso 1 1 calc R . . H5B H 0.2548 0.5274 0.0842 0.032 Uiso 1 1 calc R . . C6 C 0.43818(16) 0.47484(8) 0.21291(13) 0.0245(3) Uani 1 1 d . . . H6A H 0.4532 0.4191 0.1636 0.029 Uiso 1 1 calc R . . H6B H 0.4401 0.4589 0.3037 0.029 Uiso 1 1 calc R . . C7 C 0.58865(15) 0.54106(8) 0.18554(11) 0.0195(3) Uani 1 1 d . . . H7 H 0.5836 0.5536 0.0927 0.023 Uiso 1 1 calc R . . C8 C 0.76822(16) 0.49930(9) 0.21416(12) 0.0248(3) Uani 1 1 d . . . H8A H 0.7742 0.4390 0.1752 0.030 Uiso 1 1 calc R . . H8B H 0.8574 0.5372 0.1759 0.030 Uiso 1 1 calc R . . C9 C 0.80433(17) 0.49130(9) 0.35906(13) 0.0291(3) Uani 1 1 d . . . H9A H 0.7231 0.4484 0.3965 0.035 Uiso 1 1 calc R . . H9B H 0.9219 0.4686 0.3745 0.035 Uiso 1 1 calc R . . C10 C 0.78410(16) 0.58487(9) 0.42163(12) 0.0257(3) Uani 1 1 d . . . H10A H 0.8747 0.6253 0.3907 0.031 Uiso 1 1 calc R . . H10B H 0.8002 0.5787 0.5143 0.031 Uiso 1 1 calc R . . C11 C 0.60571(15) 0.62822(8) 0.39303(11) 0.0182(3) Uani 1 1 d . . . H11 H 0.5147 0.5918 0.4340 0.022 Uiso 1 1 calc R . . C12 C 0.60318(15) 0.72560(8) 0.44704(11) 0.0223(3) Uani 1 1 d . . . H12A H 0.7003 0.7593 0.4117 0.027 Uiso 1 1 calc R . . H12B H 0.6212 0.7226 0.5398 0.027 Uiso 1 1 calc R . . C13 C 0.28657(16) 0.75225(9) 0.50738(11) 0.0240(3) Uani 1 1 d . . . H13A H 0.1849 0.7898 0.4882 0.029 Uiso 1 1 calc R . . H13B H 0.2549 0.6887 0.4930 0.029 Uiso 1 1 calc R . . O13 O 0.33960(13) 0.76480(7) 0.63864(9) 0.0334(3) Uani 1 1 d . . . H13 H 0.250(3) 0.7950(14) 0.6773(19) 0.062(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N 0.0154(5) 0.0171(5) 0.0148(5) 0.0002(4) 0.0023(4) 0.0012(4) C1 0.0267(6) 0.0163(6) 0.0217(6) -0.0030(4) 0.0018(5) 0.0007(5) C2 0.0261(6) 0.0181(6) 0.0212(6) 0.0031(4) 0.0021(5) 0.0035(5) C3 0.0177(6) 0.0210(6) 0.0152(5) 0.0017(4) 0.0007(4) 0.0026(4) C4 0.0161(5) 0.0257(6) 0.0233(6) -0.0024(5) 0.0015(5) 0.0011(4) C5 0.0211(6) 0.0280(7) 0.0297(7) -0.0072(5) 0.0022(5) -0.0048(5) C6 0.0257(6) 0.0185(6) 0.0294(7) -0.0047(5) 0.0047(5) -0.0020(5) C7 0.0197(6) 0.0198(6) 0.0191(6) -0.0022(4) 0.0045(5) 0.0013(4) C8 0.0219(6) 0.0246(6) 0.0282(7) -0.0013(5) 0.0069(5) 0.0049(5) C9 0.0236(6) 0.0325(7) 0.0314(7) 0.0059(5) 0.0036(5) 0.0115(5) C10 0.0199(6) 0.0366(7) 0.0204(6) 0.0025(5) -0.0001(5) 0.0059(5) C11 0.0166(6) 0.0230(6) 0.0152(6) 0.0021(4) 0.0024(5) 0.0009(4) C12 0.0213(6) 0.0268(7) 0.0188(6) -0.0035(5) 0.0008(5) -0.0018(5) C13 0.0256(6) 0.0260(6) 0.0206(6) -0.0046(5) 0.0028(5) 0.0062(5) O13 0.0308(5) 0.0484(6) 0.0210(5) -0.0078(4) 0.0024(4) 0.0137(4) _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 N C11 1.4857(14) . ? N C3 1.4888(14) . ? N C7 1.4920(14) . ? C1 C13 1.5271(17) . ? C1 C12 1.5301(17) . ? C1 C2 1.5390(16) . ? C1 H1 0.9800 . ? C2 C3 1.5387(16) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.5359(16) . ? C3 H3 0.9800 . ? C4 C5 1.5335(17) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.5269(18) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.5356(16) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.5285(16) . ? C7 H7 0.9800 . ? C8 C9 1.5265(18) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.5224(19) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.5298(16) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.5292(16) . ? C11 H11 0.9800 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 O13 1.4243(15) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? O13 H13 0.91(2) . ? 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 N C3 112.68(9) . . ? C11 N C7 114.26(9) . . ? C3 N C7 109.82(9) . . ? C13 C1 C12 112.81(10) . . ? C13 C1 C2 113.96(10) . . ? C12 C1 C2 109.19(10) . . ? C13 C1 H1 106.8 . . ? C12 C1 H1 106.8 . . ? C2 C1 H1 106.8 . . ? C3 C2 C1 115.49(9) . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2A 108.4 . . ? C3 C2 H2B 108.4 . . ? C1 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? N C3 C4 113.40(9) . . ? N C3 C2 110.33(9) . . ? C4 C3 C2 115.02(9) . . ? N C3 H3 105.7 . . ? C4 C3 H3 105.7 . . ? C2 C3 H3 105.7 . . ? C5 C4 C3 110.69(9) . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C4 110.11(10) . . ? C6 C5 H5A 109.6 . . ? C4 C5 H5A 109.6 . . ? C6 C5 H5B 109.6 . . ? C4 C5 H5B 109.6 . . ? H5A C5 H5B 108.2 . . ? C5 C6 C7 110.63(10) . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? N C7 C8 110.49(9) . . ? N C7 C6 113.53(9) . . ? C8 C7 C6 112.86(10) . . ? N C7 H7 106.5 . . ? C8 C7 H7 106.5 . . ? C6 C7 H7 106.5 . . ? C9 C8 C7 111.50(10) . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? C10 C9 C8 109.42(10) . . ? C10 C9 H9A 109.8 . . ? C8 C9 H9A 109.8 . . ? C10 C9 H9B 109.8 . . ? C8 C9 H9B 109.8 . . ? H9A C9 H9B 108.2 . . ? C9 C10 C11 112.78(10) . . ? C9 C10 H10A 109.0 . . ? C11 C10 H10A 109.0 . . ? C9 C10 H10B 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? N C11 C12 109.28(9) . . ? N C11 C10 110.05(9) . . ? C12 C11 C10 109.39(10) . . ? N C11 H11 109.4 . . ? C12 C11 H11 109.4 . . ? C10 C11 H11 109.4 . . ? C11 C12 C1 114.70(10) . . ? C11 C12 H12A 108.6 . . ? C1 C12 H12A 108.6 . . ? C11 C12 H12B 108.6 . . ? C1 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? O13 C13 C1 110.08(10) . . ? O13 C13 H13A 109.6 . . ? C1 C13 H13A 109.6 . . ? O13 C13 H13B 109.6 . . ? C1 C13 H13B 109.6 . . ? H13A C13 H13B 108.2 . . ? C13 O13 H13 106.2(12) . . ? 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 C13 C1 C2 C3 -81.08(12) . . . . ? C12 C1 C2 C3 46.06(13) . . . . ? C11 N C3 C4 -73.72(12) . . . . ? C7 N C3 C4 54.87(12) . . . . ? C11 N C3 C2 56.95(11) . . . . ? C7 N C3 C2 -174.45(8) . . . . ? C1 C2 C3 N -50.57(13) . . . . ? C1 C2 C3 C4 79.24(13) . . . . ? N C3 C4 C5 -55.79(13) . . . . ? C2 C3 C4 C5 175.91(10) . . . . ? C3 C4 C5 C6 54.43(14) . . . . ? C4 C5 C6 C7 -54.39(13) . . . . ? C11 N C7 C8 -55.19(12) . . . . ? C3 N C7 C8 177.09(9) . . . . ? C11 N C7 C6 72.77(13) . . . . ? C3 N C7 C6 -54.95(12) . . . . ? C5 C6 C7 N 55.88(13) . . . . ? C5 C6 C7 C8 -177.39(9) . . . . ? N C7 C8 C9 55.31(13) . . . . ? C6 C7 C8 C9 -73.02(13) . . . . ? C7 C8 C9 C10 -55.55(13) . . . . ? C8 C9 C10 C11 55.30(13) . . . . ? C3 N C11 C12 -59.63(11) . . . . ? C7 N C11 C12 174.12(9) . . . . ? C3 N C11 C10 -179.76(9) . . . . ? C7 N C11 C10 53.99(12) . . . . ? C9 C10 C11 N -54.00(13) . . . . ? C9 C10 C11 C12 -174.07(10) . . . . ? N C11 C12 C1 56.25(13) . . . . ? C10 C11 C12 C1 176.79(9) . . . . ? C13 C1 C12 C11 78.86(12) . . . . ? C2 C1 C12 C11 -48.93(13) . . . . ? C12 C1 C13 O13 56.56(13) . . . . ? C2 C1 C13 O13 -178.20(9) . . . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 25.36 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.189 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.034