Supplementary Material (ESI) for Chemical Communications
This journal is (c) The Royal Society of Chemistry 2006

data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_publ_contact_author_name        'Thomas J.J. Muller'
_publ_contact_author_address     
;
Organisch-Chemisches Institut
Universitat Heidelberg
Im Neuenheimer Feld 270
D-69120 Heidelberg
Germany
;
_publ_contact_author_email       Thomas.J.J.Mueller@oci.uni-heidelberg.de
_publ_contact_author_phone       '+49 6221 546207'
_publ_contact_author_fax         '+49 6221 546579'
loop_
_publ_author_name
_publ_author_address
E.Merkul
;Organisch-Chemisches Institut
Universitat Heidelberg
Im Neuenheimer Feld 270
D-69120 Heidelberg
Germany
;
T.J.J.Muller
;Organisch-Chemisches Institut
Universitat Heidelberg
Im Neuenheimer Feld 270
D-69120 Heidelberg
Germany
;

data_em9
_database_code_depnum_ccdc_archive 'CCDC 615998'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.34

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                   4.6910(1)
_cell_length_b                   10.5327(2)
_cell_length_c                   31.2403(6)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     1543.55(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colurless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9667
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13309
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_av_sigmaI/netI    0.037
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2738
_reflns_number_gt                2324
_reflns_threshold_expression     >2sigma(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. 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^)+(0.0456P)^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    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(12)
_refine_ls_number_reflns         2738
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0739
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
O10 O -0.0601(3) 0.90397(11) 0.75949(4) 0.0435(4) Uani 1 1 d . . .
O16 O 0.1698(3) 0.63909(10) 0.85236(4) 0.0348(3) Uani 1 1 d . . .
O27 O 0.7548(3) 0.40476(12) 1.01870(4) 0.0498(4) Uani 1 1 d . . .
N14 N 0.4134(4) 0.81152(15) 0.87120(5) 0.0449(4) Uani 1 1 d . . .
C1 C -0.3776(4) 0.77001(15) 0.72253(5) 0.0291(4) Uani 1 1 d . . .
C2 C -0.4805(4) 0.64835(17) 0.71465(6) 0.0344(4) Uani 1 1 d . . .
C3 C -0.6714(4) 0.62631(18) 0.68185(6) 0.0364(4) Uani 1 1 d . . .
C4 C -0.7712(4) 0.72418(16) 0.65610(5) 0.0333(4) Uani 1 1 d . . .
C5 C -0.6709(4) 0.84637(17) 0.66433(6) 0.0362(4) Uani 1 1 d . . .
C6 C -0.4766(4) 0.86899(18) 0.69652(6) 0.0355(4) Uani 1 1 d . . .
C7 C -0.9797(5) 0.6987(2) 0.62083(7) 0.0431(5) Uani 1 1 d . . .
C10 C -0.1687(4) 0.79897(15) 0.75678(5) 0.0307(4) Uani 1 1 d . . .
C11 C -0.0954(4) 0.69531(17) 0.78863(6) 0.0335(4) Uani 1 1 d . . .
C12 C 0.1068(4) 0.73342(15) 0.82273(5) 0.0330(4) Uani 1 1 d . . .
C13 C 0.2541(5) 0.83635(18) 0.83467(6) 0.0421(5) Uani 1 1 d . . .
C15 C 0.3558(4) 0.69470(16) 0.88045(5) 0.0342(4) Uani 1 1 d . . .
C21 C 0.4621(4) 0.61941(16) 0.91618(5) 0.0347(4) Uani 1 1 d . . .
C22 C 0.3624(4) 0.49658(17) 0.92431(6) 0.0395(5) Uani 1 1 d . . .
C23 C 0.4651(5) 0.42815(19) 0.95853(6) 0.0428(5) Uani 1 1 d . . .
C24 C 0.6685(4) 0.47985(17) 0.98564(6) 0.0375(5) Uani 1 1 d . . .
C25 C 0.7697(4) 0.60197(19) 0.97808(6) 0.0426(5) Uani 1 1 d . . .
C26 C 0.6682(4) 0.66992(18) 0.94329(6) 0.0400(5) Uani 1 1 d . . .
C28 C 0.9521(6) 0.4570(3) 1.04846(7) 0.0541(6) Uani 1 1 d . . .
H2 H -0.416(4) 0.5773(18) 0.7315(6) 0.041(5) Uiso 1 1 d . . .
H3 H -0.736(4) 0.5408(17) 0.6761(5) 0.035(5) Uiso 1 1 d . . .
H5 H -0.751(4) 0.9165(18) 0.6473(6) 0.051(5) Uiso 1 1 d . . .
H6 H -0.403(4) 0.9552(19) 0.7023(6) 0.050(5) Uiso 1 1 d . . .
H7A H -0.936(4) 0.7442(19) 0.5953(7) 0.053(6) Uiso 1 1 d . . .
H7B H -0.993(5) 0.606(2) 0.6135(6) 0.060(6) Uiso 1 1 d . . .
H7C H -1.173(5) 0.7279(19) 0.6287(6) 0.059(6) Uiso 1 1 d . . .
H11A H -0.278(4) 0.6720(16) 0.8023(5) 0.037(5) Uiso 1 1 d . . .
H11B H -0.030(4) 0.6237(19) 0.7725(6) 0.054(6) Uiso 1 1 d . . .
H13 H 0.261(4) 0.9153(18) 0.8199(5) 0.040(5) Uiso 1 1 d . . .
H22 H 0.216(4) 0.4606(16) 0.9040(6) 0.039(5) Uiso 1 1 d . . .
H23 H 0.404(5) 0.346(2) 0.9634(6) 0.057(6) Uiso 1 1 d . . .
H25 H 0.911(4) 0.6365(17) 0.9960(6) 0.039(5) Uiso 1 1 d . . .
H26 H 0.745(4) 0.7546(17) 0.9376(5) 0.034(4) Uiso 1 1 d . . .
H28A H 0.992(5) 0.388(2) 1.0709(8) 0.072(7) Uiso 1 1 d . . .
H28B H 1.142(6) 0.485(2) 1.0355(7) 0.079(8) Uiso 1 1 d . . .
H28C H 0.876(5) 0.5301(19) 1.0614(6) 0.053(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
O10 0.0573(9) 0.0267(7) 0.0465(8) 0.0010(5) -0.0069(7) -0.0073(6)
O16 0.0416(7) 0.0286(6) 0.0341(6) -0.0012(5) -0.0041(6) -0.0021(6)
O27 0.0590(9) 0.0482(8) 0.0422(7) 0.0043(6) -0.0121(7) 0.0040(7)
N14 0.0532(10) 0.0342(9) 0.0472(10) 0.0013(7) -0.0129(8) -0.0063(8)
C1 0.0307(9) 0.0255(9) 0.0310(9) -0.0001(7) 0.0063(7) 0.0056(7)
C2 0.0377(11) 0.0283(10) 0.0371(10) 0.0058(8) -0.0009(9) 0.0011(8)
C3 0.0359(10) 0.0331(10) 0.0403(11) 0.0005(8) 0.0005(9) -0.0025(9)
C4 0.0276(9) 0.0403(11) 0.0318(10) 0.0009(7) 0.0055(8) 0.0055(8)
C5 0.0377(10) 0.0343(10) 0.0365(10) 0.0058(8) 0.0023(9) 0.0093(9)
C6 0.0387(11) 0.0281(10) 0.0396(11) 0.0018(8) 0.0053(9) 0.0029(8)
C7 0.0372(12) 0.0531(14) 0.0391(12) 0.0012(10) -0.0012(9) 0.0074(10)
C10 0.0337(10) 0.0271(9) 0.0312(9) -0.0042(7) 0.0053(8) 0.0020(8)
C11 0.0370(11) 0.0285(9) 0.0349(10) -0.0013(8) -0.0016(9) 0.0004(8)
C12 0.0371(10) 0.0273(9) 0.0345(10) 0.0002(7) 0.0014(8) 0.0032(8)
C13 0.0503(12) 0.0297(10) 0.0462(11) 0.0037(9) -0.0101(10) -0.0061(9)
C15 0.0357(10) 0.0333(10) 0.0335(10) -0.0071(7) -0.0026(8) 0.0003(8)
C21 0.0367(10) 0.0342(10) 0.0333(10) -0.0061(8) 0.0005(8) 0.0042(8)
C22 0.0477(12) 0.0361(10) 0.0346(10) -0.0048(8) -0.0049(10) -0.0041(9)
C23 0.0552(14) 0.0333(11) 0.0400(11) -0.0019(8) -0.0029(10) -0.0034(10)
C24 0.0432(12) 0.0383(10) 0.0311(10) -0.0026(8) 0.0012(9) 0.0062(9)
C25 0.0409(11) 0.0469(12) 0.0401(11) -0.0053(9) -0.0082(10) -0.0001(10)
C26 0.0416(11) 0.0350(10) 0.0436(11) -0.0030(8) -0.0031(10) -0.0037(9)
C28 0.0507(15) 0.0724(17) 0.0393(13) 0.0064(12) -0.0072(12) -0.0006(13)

_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
O10 C10 1.221(2) . ?
O16 C15 1.369(2) . ?
O16 C12 1.3896(19) . ?
O27 C24 1.362(2) . ?
O27 C28 1.423(3) . ?
N14 C15 1.293(2) . ?
N14 C13 1.389(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.401(2) . ?
C1 C10 1.483(2) . ?
C2 C3 1.380(3) . ?
C2 H2 0.963(19) . ?
C3 C4 1.389(2) . ?
C3 H3 0.966(17) . ?
C4 C5 1.394(2) . ?
C4 C7 1.498(3) . ?
C5 C6 1.378(3) . ?
C5 H5 0.98(2) . ?
C6 H6 0.99(2) . ?
C7 H7A 0.95(2) . ?
C7 H7B 1.00(2) . ?
C7 H7C 0.99(2) . ?
C10 C11 1.517(2) . ?
C11 C12 1.482(2) . ?
C11 H11A 0.989(19) . ?
C11 H11B 0.96(2) . ?
C12 C13 1.339(2) . ?
C13 H13 0.951(18) . ?
C15 C21 1.457(2) . ?
C21 C26 1.391(2) . ?
C21 C22 1.399(3) . ?
C22 C23 1.376(3) . ?
C22 H22 1.009(19) . ?
C23 C24 1.387(3) . ?
C23 H23 0.92(2) . ?
C24 C25 1.391(3) . ?
C25 C26 1.386(3) . ?
C25 H25 0.94(2) . ?
C26 H26 0.979(18) . ?
C28 H28A 1.03(2) . ?
C28 H28B 1.02(3) . ?
C28 H28C 0.94(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
C15 O16 C12 104.87(13) . . ?
C24 O27 C28 117.67(16) . . ?
C15 N14 C13 104.51(16) . . ?
C2 C1 C6 117.90(16) . . ?
C2 C1 C10 123.13(15) . . ?
C6 C1 C10 118.98(15) . . ?
C3 C2 C1 120.75(16) . . ?
C3 C2 H2 118.5(11) . . ?
C1 C2 H2 120.7(11) . . ?
C2 C3 C4 121.58(17) . . ?
C2 C3 H3 119.8(10) . . ?
C4 C3 H3 118.6(10) . . ?
C3 C4 C5 117.69(16) . . ?
C3 C4 C7 120.90(17) . . ?
C5 C4 C7 121.41(16) . . ?
C6 C5 C4 121.16(16) . . ?
C6 C5 H5 121.1(12) . . ?
C4 C5 H5 117.6(11) . . ?
C5 C6 C1 120.91(18) . . ?
C5 C6 H6 121.6(11) . . ?
C1 C6 H6 117.5(12) . . ?
C4 C7 H7A 112.7(13) . . ?
C4 C7 H7B 112.5(12) . . ?
H7A C7 H7B 108.2(16) . . ?
C4 C7 H7C 111.1(12) . . ?
H7A C7 H7C 104.5(17) . . ?
H7B C7 H7C 107.4(17) . . ?
O10 C10 C1 120.82(15) . . ?
O10 C10 C11 120.82(15) . . ?
C1 C10 C11 118.36(14) . . ?
C12 C11 C10 114.93(15) . . ?
C12 C11 H11A 108.1(10) . . ?
C10 C11 H11A 105.5(10) . . ?
C12 C11 H11B 112.7(12) . . ?
C10 C11 H11B 107.1(12) . . ?
H11A C11 H11B 108.1(16) . . ?
C13 C12 O16 106.49(15) . . ?
C13 C12 C11 138.60(17) . . ?
O16 C12 C11 114.91(14) . . ?
C12 C13 N14 110.74(17) . . ?
C12 C13 H13 126.2(11) . . ?
N14 C13 H13 123.0(11) . . ?
N14 C15 O16 113.40(15) . . ?
N14 C15 C21 128.16(17) . . ?
O16 C15 C21 118.44(15) . . ?
C26 C21 C22 118.39(16) . . ?
C26 C21 C15 119.74(17) . . ?
C22 C21 C15 121.87(16) . . ?
C23 C22 C21 120.55(18) . . ?
C23 C22 H22 122.0(10) . . ?
C21 C22 H22 117.4(10) . . ?
C22 C23 C24 120.62(19) . . ?
C22 C23 H23 120.8(14) . . ?
C24 C23 H23 118.6(13) . . ?
O27 C24 C23 116.06(17) . . ?
O27 C24 C25 124.33(17) . . ?
C23 C24 C25 119.61(17) . . ?
C26 C25 C24 119.56(18) . . ?
C26 C25 H25 120.6(11) . . ?
C24 C25 H25 119.8(11) . . ?
C25 C26 C21 121.25(18) . . ?
C25 C26 H26 119.1(10) . . ?
C21 C26 H26 119.7(10) . . ?
O27 C28 H28A 106.9(13) . . ?
O27 C28 H28B 114.7(13) . . ?
H28A C28 H28B 108.2(19) . . ?
O27 C28 H28C 110.4(13) . . ?
H28A C28 H28C 111.0(18) . . ?
H28B C28 H28C 105.7(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.8(3) . . . . ?
C10 C1 C2 C3 -178.89(16) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C2 C3 C4 C7 -179.60(17) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C7 C4 C5 C6 -179.25(17) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C10 C1 C6 C5 -179.96(15) . . . . ?
C2 C1 C10 O10 171.68(17) . . . . ?
C6 C1 C10 O10 -8.0(2) . . . . ?
C2 C1 C10 C11 -8.9(2) . . . . ?
C6 C1 C10 C11 171.41(15) . . . . ?
O10 C10 C11 C12 1.5(3) . . . . ?
C1 C10 C11 C12 -177.86(15) . . . . ?
C15 O16 C12 C13 -0.11(19) . . . . ?
C15 O16 C12 C11 -179.67(15) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C10 C11 C12 O16 178.89(14) . . . . ?
O16 C12 C13 N14 0.4(2) . . . . ?
C11 C12 C13 N14 179.8(2) . . . . ?
C15 N14 C13 C12 -0.5(2) . . . . ?
C13 N14 C15 O16 0.5(2) . . . . ?
C13 N14 C15 C21 -179.23(18) . . . . ?
C12 O16 C15 N14 -0.2(2) . . . . ?
C12 O16 C15 C21 179.49(15) . . . . ?
N14 C15 C21 C26 -5.4(3) . . . . ?
O16 C15 C21 C26 174.93(15) . . . . ?
N14 C15 C21 C22 174.51(19) . . . . ?
O16 C15 C21 C22 -5.2(3) . . . . ?
C26 C21 C22 C23 0.5(3) . . . . ?
C15 C21 C22 C23 -179.44(18) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C28 O27 C24 C23 -176.79(18) . . . . ?
C28 O27 C24 C25 2.9(3) . . . . ?
C22 C23 C24 O27 179.59(17) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
O27 C24 C25 C26 179.65(18) . . . . ?
C23 C24 C25 C26 -0.7(3) . . . . ?
C24 C25 C26 C21 1.4(3) . . . . ?
C22 C21 C26 C25 -1.3(3) . . . . ?
C15 C21 C26 C25 178.63(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.038