# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'A Furstner' 'Jens Ackerstaff' _publ_contact_author_name 'Alois Furstner' _publ_contact_author_email FUERSTNER@MPI-MUELHEIM.MPG.DE _publ_section_title ; Formal Total Synthesis of (?)-Haouamine A ; ############################################################################ # # _publ_requested_journal 'Chem. Comm.' # Attachment 'Ackerstaff_5370.CIF' ############################################################################ # # # # # ### # # ### ### # ### # # ### # # ### # ### # # # # # # # # # # # # # ## ## # ## # # # # # # # # # # ### # # ### ### # ### # # # ### # ## # ### ### # # # # # # # # # # # # # # # # # # ## # # # ### ### # # ### ### # # ### # # # # # # # # # # # # # # # # # ### ### ### # # # # # ## ## # # # # # # # # # # # # # # # ### # ### ### # ### # # # # # # # # # ## # # # # # # # # # # # ### # # # # # ### # # # # # ############################################################################ ############################################################################ # # # This Supplementary Material is written in the Crystallographic # # Information File (CIF) format. For further details see: S.R. Hall, # # F.H. Allen and I.D. Brown, Acta Cryst. (1991) A47, 655-685. # # # ############################################################################ data_5370 _database_code_depnum_ccdc_archive 'CCDC 683071' #_publ_requested_category ?FI ; full inorganic #_publ_requested_category ?FM ; full organometallic #_publ_requested_category ?FO ; full organic #?If CI, CM or CO remember to remove section "..._molecular_graphics" #_publ_requested_category ?CI ; electronic inorganic #_publ_requested_category ?CM ; electronic organometallic #_publ_requested_category ?CO ; electronic organic _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_compound_source toluene/pentane _chemical_formula_moiety 'C21 H21 N O4' _chemical_formula_sum 'C21 H21 N O4' _chemical_formula_weight 351.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 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 5.11170(10) _cell_length_b 9.8304(2) _cell_length_c 34.9917(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1758.33(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 34557 _cell_measurement_theta_min 4.67 _cell_measurement_theta_max 68.79 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method none _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.749 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Scalepack, Otwinowski (1997)' _exptl_absorpt_correction_T_min 1 _exptl_absorpt_correction_T_max 1 _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_monochromator 'focusing multilayer optic' _diffrn_measurement_device_type 'Bruker AXS X8 Proteum' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 34417 _diffrn_reflns_av_R_equivalents 0.0511 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 4.67 _diffrn_reflns_theta_max 68.79 _reflns_number_total 3215 _reflns_number_gt 3189 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'PROTEUM2 (Bruker AXS, 2004)' _computing_cell_refinement 'PROTEUM2 (Bruker AXS, 2004)' _computing_data_reduction 'SAINT software (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _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^)+(0.0187P)^2^+0.7075P] 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_abs_structure_details 'Flack, H. D. (1983). Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(2) _chemical_absolute_configuration rm _refine_ls_number_reflns 3215 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0340 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0787 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.162 _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 N1 N -0.7016(3) -0.36144(14) -0.10889(4) 0.0259(3) Uani 1 1 d . . . C2 C -0.7197(3) -0.30847(18) -0.06999(4) 0.0274(4) Uani 1 1 d . . . H2A H -0.6647 -0.2119 -0.0697 0.033 Uiso 1 1 calc R . . H2B H -0.6001 -0.3601 -0.0531 0.033 Uiso 1 1 calc R . . C3 C -0.9983(3) -0.32011(16) -0.05499(4) 0.0255(3) Uani 1 1 d . . . H3 H -1.1182 -0.2597 -0.0699 0.031 Uiso 1 1 calc R . . O3 O -0.9862(2) -0.27691(13) -0.01582(3) 0.0309(3) Uani 1 1 d . . . H3A H -1.1370 -0.2562 -0.0082 0.046 Uiso 1 1 calc R . . C4 C -1.0868(3) -0.46617(17) -0.05772(4) 0.0260(3) Uani 1 1 d . . . H4 H -1.2038 -0.5024 -0.0392 0.031 Uiso 1 1 calc R . . C4A C -1.0004(3) -0.54405(16) -0.08610(4) 0.0234(3) Uani 1 1 d . . . C4B C -1.0200(3) -0.69112(16) -0.09295(4) 0.0243(3) Uani 1 1 d . . . C5 C -1.1870(3) -0.78919(17) -0.07702(4) 0.0249(3) Uani 1 1 d . . . O5 O -1.3649(2) -0.74318(11) -0.05083(3) 0.0285(3) Uani 1 1 d . . . C5' C -1.5261(4) -0.84323(18) -0.03266(5) 0.0342(4) Uani 1 1 d . . . H5'1 H -1.4151 -0.9113 -0.0202 0.051 Uiso 1 1 calc R . . H5'2 H -1.6364 -0.8877 -0.0519 0.051 Uiso 1 1 calc R . . H5'3 H -1.6372 -0.7991 -0.0135 0.051 Uiso 1 1 calc R . . C6 C -1.1681(4) -0.92356(17) -0.08915(5) 0.0281(4) Uani 1 1 d . . . H6 H -1.2854 -0.9903 -0.0795 0.034 Uiso 1 1 calc R . . C7 C -0.9756(4) -0.95970(17) -0.11554(5) 0.0308(4) Uani 1 1 d . . . H7 H -0.9629 -1.0518 -0.1236 0.037 Uiso 1 1 calc R . . C8 C -0.8027(4) -0.86493(18) -0.13035(5) 0.0299(4) Uani 1 1 d . . . H8 H -0.6699 -0.8916 -0.1478 0.036 Uiso 1 1 calc R . . C8A C -0.8279(3) -0.73041(17) -0.11915(4) 0.0273(4) Uani 1 1 d . . . C9 C -0.6645(3) -0.60970(16) -0.13084(5) 0.0274(4) Uani 1 1 d . . . H9A H -0.6319 -0.6096 -0.1587 0.033 Uiso 1 1 calc R . . H9B H -0.4948 -0.6087 -0.1172 0.033 Uiso 1 1 calc R . . C9A C -0.8363(3) -0.48834(16) -0.11893(4) 0.0246(3) Uani 1 1 d . . . H9A1 H -0.9575 -0.4680 -0.1406 0.030 Uiso 1 1 calc R . . C10 C -0.5501(3) -0.29420(16) -0.13452(4) 0.0257(3) Uani 1 1 d . . . O10 O -0.4236(2) -0.19191(12) -0.12784(3) 0.0345(3) Uani 1 1 d . . . O11 O -0.5595(2) -0.35611(12) -0.16923(3) 0.0299(3) Uani 1 1 d . . . C12 C -0.4178(4) -0.29022(19) -0.20024(5) 0.0337(4) Uani 1 1 d . . . H12A H -0.3178 -0.3590 -0.2148 0.040 Uiso 1 1 calc R . . H12B H -0.2923 -0.2235 -0.1896 0.040 Uiso 1 1 calc R . . C13 C -0.6068(3) -0.21933(17) -0.22621(5) 0.0290(4) Uani 1 1 d . . . C14 C -0.7690(4) -0.11835(19) -0.21191(5) 0.0370(4) Uani 1 1 d . . . H14 H -0.7547 -0.0930 -0.1858 0.044 Uiso 1 1 calc R . . C15 C -0.9510(4) -0.0539(2) -0.23481(7) 0.0499(5) Uani 1 1 d . . . H15 H -1.0612 0.0144 -0.2243 0.060 Uiso 1 1 calc R . . C16 C -0.9729(5) -0.0880(3) -0.27250(7) 0.0544(6) Uani 1 1 d . . . H16 H -1.0985 -0.0438 -0.2882 0.065 Uiso 1 1 calc R . . C17 C -0.8129(5) -0.1865(3) -0.28772(6) 0.0540(6) Uani 1 1 d . . . H17 H -0.8280 -0.2098 -0.3140 0.065 Uiso 1 1 calc R . . C18 C -0.6265(4) -0.2532(2) -0.26467(5) 0.0416(5) Uani 1 1 d . . . H18 H -0.5154 -0.3207 -0.2753 0.050 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 N1 0.0263(7) 0.0263(7) 0.0251(6) -0.0013(5) 0.0006(6) -0.0059(6) C2 0.0250(8) 0.0298(9) 0.0274(8) -0.0055(7) -0.0012(7) -0.0014(7) C3 0.0232(8) 0.0283(8) 0.0250(7) -0.0037(6) -0.0026(6) 0.0033(7) O3 0.0247(6) 0.0393(7) 0.0287(5) -0.0099(5) 0.0016(5) 0.0013(6) C4 0.0217(8) 0.0300(9) 0.0264(8) 0.0025(6) -0.0019(6) 0.0017(7) C4A 0.0186(8) 0.0245(8) 0.0271(7) 0.0015(6) -0.0021(6) -0.0026(7) C4B 0.0231(8) 0.0232(8) 0.0267(7) 0.0015(6) -0.0049(7) -0.0026(7) C5 0.0225(7) 0.0276(8) 0.0244(7) 0.0001(6) -0.0015(6) -0.0001(7) O5 0.0262(6) 0.0292(6) 0.0300(6) 0.0001(5) 0.0041(5) -0.0021(5) C5' 0.0323(9) 0.0369(10) 0.0335(9) 0.0031(7) 0.0075(8) -0.0055(9) C6 0.0277(8) 0.0244(8) 0.0321(8) 0.0009(7) 0.0004(7) -0.0050(7) C7 0.0326(9) 0.0242(8) 0.0357(9) -0.0040(7) 0.0014(8) -0.0005(8) C8 0.0289(9) 0.0303(9) 0.0304(8) -0.0025(7) 0.0023(7) -0.0015(8) C8A 0.0280(8) 0.0288(9) 0.0251(7) 0.0005(6) -0.0021(7) -0.0004(8) C9 0.0247(8) 0.0278(9) 0.0296(8) 0.0011(6) 0.0018(7) -0.0032(7) C9A 0.0233(8) 0.0264(8) 0.0241(7) 0.0012(6) 0.0001(6) -0.0045(7) C10 0.0220(8) 0.0244(8) 0.0306(8) 0.0012(6) -0.0008(6) -0.0002(7) O10 0.0345(7) 0.0295(6) 0.0394(6) -0.0007(5) 0.0008(5) -0.0079(6) O11 0.0360(7) 0.0286(6) 0.0251(5) 0.0018(5) 0.0052(5) -0.0053(6) C12 0.0346(10) 0.0348(10) 0.0319(8) 0.0058(7) 0.0109(7) -0.0010(8) C13 0.0305(9) 0.0269(8) 0.0296(8) 0.0039(7) 0.0047(7) -0.0091(7) C14 0.0405(11) 0.0304(10) 0.0401(10) 0.0030(8) 0.0037(8) -0.0026(8) C15 0.0427(12) 0.0409(12) 0.0661(14) 0.0190(10) 0.0029(11) 0.0022(10) C16 0.0377(12) 0.0635(14) 0.0620(14) 0.0277(11) -0.0114(11) -0.0135(11) C17 0.0567(13) 0.0732(16) 0.0322(10) 0.0121(10) -0.0098(10) -0.0309(14) C18 0.0452(12) 0.0460(11) 0.0335(9) -0.0027(8) 0.0072(8) -0.0152(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 N1 C10 1.357(2) . Y N1 C2 1.4605(19) . Y N1 C9A 1.468(2) . Y C2 C3 1.522(2) . Y C2 H2A 0.9900 . N C2 H2B 0.9900 . N C3 O3 1.4363(18) . Y C3 C4 1.508(2) . Y C3 H3 1.0000 . N O3 H3A 0.8400 . N C4 C4A 1.330(2) . Y C4 H4 0.9500 . N C4A C4B 1.469(2) . Y C4A C9A 1.524(2) . Y C4B C8A 1.398(2) . Y C4B C5 1.403(2) . Y C5 O5 1.3677(19) . Y C5 C6 1.391(2) . Y O5 C5' 1.432(2) . Y C5' H5'1 0.9800 . N C5' H5'2 0.9800 . N C5' H5'3 0.9800 . N C6 C7 1.395(2) . Y C6 H6 0.9500 . N C7 C8 1.385(2) . Y C7 H7 0.9500 . N C8 C8A 1.385(2) . Y C8 H8 0.9500 . N C8A C9 1.508(2) . Y C9 C9A 1.539(2) . Y C9 H9A 0.9900 . N C9 H9B 0.9900 . N C9A H9A1 1.0000 . N C10 O10 1.218(2) . Y C10 O11 1.3596(19) . Y O11 C12 1.4565(19) . Y C12 C13 1.498(2) . Y C12 H12A 0.9900 . N C12 H12B 0.9900 . N C13 C14 1.387(3) . Y C13 C18 1.390(2) . Y C14 C15 1.382(3) . Y C14 H14 0.9500 . N C15 C16 1.365(3) . Y C15 H15 0.9500 . N C16 C17 1.375(3) . Y C16 H16 0.9500 . N C17 C18 1.410(3) . Y C17 H17 0.9500 . N C18 H18 0.9500 . N 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 C10 N1 C2 118.59(13) . . Y C10 N1 C9A 121.58(13) . . Y C2 N1 C9A 119.77(13) . . Y N1 C2 C3 110.72(13) . . Y N1 C2 H2A 109.5 . . N C3 C2 H2A 109.5 . . N N1 C2 H2B 109.5 . . N C3 C2 H2B 109.5 . . N H2A C2 H2B 108.1 . . N O3 C3 C4 110.78(13) . . Y O3 C3 C2 105.44(12) . . Y C4 C3 C2 109.29(13) . . Y O3 C3 H3 110.4 . . N C4 C3 H3 110.4 . . N C2 C3 H3 110.4 . . N C3 O3 H3A 109.5 . . N C4A C4 C3 119.72(15) . . Y C4A C4 H4 120.1 . . N C3 C4 H4 120.1 . . N C4 C4A C4B 131.76(15) . . Y C4 C4A C9A 122.62(14) . . Y C4B C4A C9A 105.55(13) . . Y C8A C4B C5 119.87(15) . . Y C8A C4B C4A 109.34(14) . . Y C5 C4B C4A 130.75(15) . . Y O5 C5 C6 124.39(15) . . Y O5 C5 C4B 116.31(14) . . Y C6 C5 C4B 119.27(15) . . Y C5 O5 C5' 116.92(13) . . Y O5 C5' H5'1 109.5 . . N O5 C5' H5'2 109.5 . . N H5'1 C5' H5'2 109.5 . . N O5 C5' H5'3 109.5 . . N H5'1 C5' H5'3 109.5 . . N H5'2 C5' H5'3 109.5 . . N C5 C6 C7 119.53(16) . . Y C5 C6 H6 120.2 . . N C7 C6 H6 120.2 . . N C8 C7 C6 121.77(16) . . Y C8 C7 H7 119.1 . . N C6 C7 H7 119.1 . . N C7 C8 C8A 118.48(16) . . Y C7 C8 H8 120.8 . . N C8A C8 H8 120.8 . . N C8 C8A C4B 120.98(16) . . Y C8 C8A C9 128.53(16) . . Y C4B C8A C9 110.47(14) . . Y C8A C9 C9A 102.74(13) . . Y C8A C9 H9A 111.2 . . N C9A C9 H9A 111.2 . . N C8A C9 H9B 111.2 . . N C9A C9 H9B 111.2 . . N H9A C9 H9B 109.1 . . N N1 C9A C4A 112.53(12) . . Y N1 C9A C9 117.14(14) . . Y C4A C9A C9 103.87(12) . . Y N1 C9A H9A1 107.6 . . N C4A C9A H9A1 107.6 . . N C9 C9A H9A1 107.6 . . N O10 C10 N1 125.34(15) . . Y O10 C10 O11 124.04(14) . . Y N1 C10 O11 110.62(13) . . Y C10 O11 C12 116.67(13) . . Y O11 C12 C13 109.75(14) . . Y O11 C12 H12A 109.7 . . N C13 C12 H12A 109.7 . . N O11 C12 H12B 109.7 . . N C13 C12 H12B 109.7 . . N H12A C12 H12B 108.2 . . N C14 C13 C18 118.49(17) . . Y C14 C13 C12 119.98(15) . . Y C18 C13 C12 121.53(17) . . Y C15 C14 C13 121.44(19) . . Y C15 C14 H14 119.3 . . N C13 C14 H14 119.3 . . N C16 C15 C14 120.2(2) . . Y C16 C15 H15 119.9 . . N C14 C15 H15 119.9 . . N C15 C16 C17 119.9(2) . . Y C15 C16 H16 120.0 . . N C17 C16 H16 120.0 . . N C16 C17 C18 120.50(19) . . Y C16 C17 H17 119.7 . . N C18 C17 H17 119.7 . . N C13 C18 C17 119.5(2) . . Y C13 C18 H18 120.3 . . N C17 C18 H18 120.3 . . N _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 68.79 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.158 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.043