# Supplementary Material (ESI) for ChemComm
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 182/1557

data_3c

_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           128-129
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H17 N O3'
_chemical_formula_weight          235.28

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    Cc

loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 'x, -y, z+1/2'
 'x+1/2, y+1/2, z'
 'x+1/2, -y+1/2, z+1/2'

_cell_length_a                    15.632(1)
_cell_length_b                    9.417(1)
_cell_length_c                    9.668(1)
_cell_angle_alpha                 90.00
_cell_angle_beta                  111.10(1)
_cell_angle_gamma                 90.00
_cell_volume                      1327.8(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     1889
_cell_measurement_theta_min       2.57
_cell_measurement_theta_max       27

_exptl_crystal_description        prism
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.10 
_exptl_crystal_size_mid           0.05 
_exptl_crystal_size_min           0.05 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.177
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              504
_exptl_absorpt_coefficient_mu     0.084
_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       293(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   'Nonius KappaCCD'
_diffrn_measurement_method        Phi/Omega-scans
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             1890
_diffrn_reflns_av_R_equivalents   0.2000
_diffrn_reflns_av_sigmaI/netI     0.0692
_diffrn_reflns_limit_h_min        -19
_diffrn_reflns_limit_h_max        18
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_theta_min          2.57
_diffrn_reflns_theta_max          27.00
_reflns_number_total              1889
_reflns_number_gt                 1055
_reflns_threshold_expression      >2sigma(I)

_computing_data_collection        'Nonius COLLECT'
_computing_cell_refinement        'Nomius DENZO'
_computing_data_reduction         'Nonius DENZO'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'XTAL'

_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^)+(0.0000P)^2^+0.4750P] 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      SHELXL
_refine_ls_extinction_coef        0.0091(12)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0(2)
_refine_ls_number_reflns          1889
_refine_ls_number_parameters      225
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.1224
_refine_ls_R_factor_gt            0.0505
_refine_ls_wR_factor_ref          0.0961
_refine_ls_wR_factor_gt           0.0757
_refine_ls_goodness_of_fit_ref    1.108
_refine_ls_restrained_S_all       1.108
_refine_ls_shift/su_max           0.866
_refine_ls_shift/su_mean          0.110

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 0.1972(3) 0.5054(3) 0.3222(3) 0.0947(12) Uani 1 1 d . . .
C2 C 0.3620(5) 0.8503(8) 0.0660(6) 0.0957(18) Uani 1 1 d . . .
H2 H 0.337(5) 0.946(7) 0.055(7) 0.15(3) Uiso 1 1 d . . .
N3 N 0.1844(3) 0.5814(4) 0.0969(4) 0.0637(11) Uani 1 1 d . . .
H3N H 0.185(3) 0.566(4) 0.013(4) 0.059(12) Uiso 1 1 d . . .
C4 C 0.1780(3) 0.7304(5) 0.1321(4) 0.0606(13) Uani 1 1 d . . .
O5 O 0.1216(2) 0.8346(4) 0.3094(4) 0.1032(13) Uani 1 1 d . . .
H5O H 0.211(5) 0.956(7) 0.248(8) 0.15(3) Uiso 1 1 d . . .
C6 C 0.1087(4) 0.7495(6) 0.2089(6) 0.0796(16) Uani 1 1 d . . .
C7 C 0.2735(4) 0.7871(6) 0.2291(6) 0.0791(17) Uani 1 1 d . . .
H7 H 0.290(3) 0.737(5) 0.314(6) 0.076(15) Uiso 1 1 d . . .
C8 C 0.2178(6) 0.3328(7) 0.1556(8) 0.0915(19) Uani 1 1 d . . .
H8A H 0.274(5) 0.291(8) 0.219(8) 0.16(4) Uiso 1 1 d . . .
H8B H 0.209(4) 0.318(5) 0.064(9) 0.13(2) Uiso 1 1 d . . .
H8C H 0.172(6) 0.269(9) 0.183(9) 0.22(4) Uiso 1 1 d . . .
O9 O 0.2708(3) 0.9363(4) 0.2527(4) 0.1150(16) Uani 1 1 d . . .
C10 C 0.1987(3) 0.4786(5) 0.1974(5) 0.0694(14) Uani 1 1 d . . .
C11 C 0.1371(5) 0.8108(7) -0.0173(6) 0.0899(18) Uani 1 1 d . . .
H11A H 0.172(3) 0.801(4) -0.074(5) 0.080(15) Uiso 1 1 d . . .
H11B H 0.129(4) 0.920(7) 0.001(6) 0.13(2) Uiso 1 1 d . . .
H11C H 0.069(5) 0.765(7) -0.077(7) 0.16(3) Uiso 1 1 d . . .
C12 C 0.3943(4) 0.6310(8) 0.1940(7) 0.0940(18) Uani 1 1 d . . .
H12 H 0.384(3) 0.579(5) 0.261(5) 0.069(15) Uiso 1 1 d . . .
C13 C 0.3455(4) 0.7573(6) 0.1643(5) 0.0773(15) Uani 1 1 d . . .
C14 C 0.4228(6) 0.8159(11) -0.0028(7) 0.116(2) Uani 1 1 d . . .
H14 H 0.432(4) 0.882(6) -0.086(7) 0.126(19) Uiso 1 1 d . . .
C15 C 0.4695(5) 0.6918(12) 0.0251(9) 0.118(2) Uani 1 1 d . . .
H15 H 0.521(5) 0.672(7) -0.024(7) 0.16(3) Uiso 1 1 d . . .
C16 C 0.0187(5) 0.6699(12) 0.1521(10) 0.117(2) Uani 1 1 d . . .
H16A H 0.018(8) 0.584(12) 0.195(11) 0.24(6) Uiso 1 1 d . . .
H16B H 0.003(5) 0.646(7) 0.051(9) 0.17(3) Uiso 1 1 d . . .
H16C H -0.036(5) 0.702(8) 0.175(7) 0.18(3) Uiso 1 1 d . . .
C17 C 0.4562(5) 0.5997(9) 0.1222(9) 0.113(2) Uani 1 1 d . . .
H17 H 0.489(4) 0.516(6) 0.145(6) 0.08(2) 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
O1 0.152(3) 0.096(3) 0.050(2) 0.0016(15) 0.0525(19) -0.003(2)
C2 0.107(5) 0.089(5) 0.104(5) -0.008(3) 0.053(4) -0.024(4)
N3 0.085(3) 0.071(3) 0.041(2) 0.001(2) 0.031(2) -0.005(2)
C4 0.079(3) 0.061(3) 0.048(3) -0.005(2) 0.031(3) 0.003(3)
O5 0.135(3) 0.106(3) 0.089(3) -0.022(2) 0.064(2) 0.007(2)
C6 0.087(5) 0.090(4) 0.067(4) -0.002(3) 0.034(3) 0.009(3)
C7 0.112(5) 0.067(4) 0.063(4) -0.012(3) 0.037(4) -0.018(3)
C8 0.140(7) 0.074(4) 0.069(4) -0.002(3) 0.049(4) 0.001(4)
O9 0.142(5) 0.082(3) 0.133(4) -0.042(2) 0.065(3) -0.016(3)
C10 0.089(4) 0.081(4) 0.046(3) 0.000(2) 0.033(2) -0.007(3)
C11 0.116(6) 0.091(5) 0.069(4) 0.023(3) 0.041(4) 0.023(4)
C12 0.084(5) 0.111(6) 0.077(4) 0.005(3) 0.017(3) -0.010(4)
C13 0.092(4) 0.080(4) 0.066(3) -0.010(2) 0.035(3) -0.017(3)
C14 0.119(6) 0.136(7) 0.107(6) -0.002(4) 0.058(5) -0.024(5)
C15 0.078(5) 0.160(8) 0.119(6) -0.020(5) 0.039(4) -0.020(5)
C16 0.094(6) 0.156(8) 0.123(6) -0.031(5) 0.064(5) -0.013(5)
C17 0.089(5) 0.121(6) 0.122(6) 0.000(5) 0.029(5) 0.018(5)

_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 C10 1.241(4) . ?
C2 C14 1.381(9) . ?
C2 C13 1.383(8) . ?
N3 C10 1.332(5) . ?
N3 C4 1.455(5) . ?
C4 C6 1.527(6) . ?
C4 C11 1.551(6) . ?
C4 C7 1.545(6) . ?
O5 C6 1.219(5) . ?
C6 C16 1.512(9) . ?
C7 O9 1.426(6) . ?
C7 C13 1.499(7) . ?
C8 C10 1.491(7) . ?
C12 C13 1.386(7) . ?
C12 C17 1.410(9) . ?
C14 C15 1.352(9) . ?
C15 C17 1.348(10) . ?

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
C14 C2 C13 120.9(7) . . ?
C10 N3 C4 122.5(4) . . ?
N3 C4 C6 110.4(4) . . ?
N3 C4 C11 107.0(4) . . ?
C6 C4 C11 105.6(4) . . ?
N3 C4 C7 110.0(4) . . ?
C6 C4 C7 111.3(4) . . ?
C11 C4 C7 112.4(5) . . ?
O5 C6 C16 118.7(5) . . ?
O5 C6 C4 121.5(5) . . ?
C16 C6 C4 119.6(5) . . ?
O9 C7 C13 108.7(5) . . ?
O9 C7 C4 111.1(5) . . ?
C13 C7 C4 112.9(4) . . ?
O1 C10 N3 120.3(4) . . ?
O1 C10 C8 121.8(4) . . ?
N3 C10 C8 117.9(4) . . ?
C13 C12 C17 120.1(7) . . ?
C12 C13 C2 117.4(6) . . ?
C12 C13 C7 121.0(5) . . ?
C2 C13 C7 121.5(6) . . ?
C15 C14 C2 121.5(7) . . ?
C14 C15 C17 119.2(7) . . ?
C15 C17 C12 120.9(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
C10 N3 C4 C6 -51.4(6) . . . . ?
C10 N3 C4 C11 -165.9(5) . . . . ?
C10 N3 C4 C7 71.8(5) . . . . ?
N3 C4 C6 O5 142.3(5) . . . . ?
C11 C4 C6 O5 -102.3(6) . . . . ?
C7 C4 C6 O5 19.8(6) . . . . ?
N3 C4 C6 C16 -42.4(8) . . . . ?
C11 C4 C6 C16 72.9(7) . . . . ?
C7 C4 C6 C16 -164.9(6) . . . . ?
N3 C4 C7 O9 174.1(4) . . . . ?
C6 C4 C7 O9 -63.2(5) . . . . ?
C11 C4 C7 O9 54.9(5) . . . . ?
N3 C4 C7 C13 51.7(5) . . . . ?
C6 C4 C7 C13 174.3(5) . . . . ?
C11 C4 C7 C13 -67.5(6) . . . . ?
C4 N3 C10 O1 8.0(6) . . . . ?
C4 N3 C10 C8 -171.1(6) . . . . ?
C17 C12 C13 C2 -1.5(8) . . . . ?
C17 C12 C13 C7 174.6(6) . . . . ?
C14 C2 C13 C12 1.9(8) . . . . ?
C14 C2 C13 C7 -174.3(5) . . . . ?
O9 C7 C13 C12 148.5(5) . . . . ?
C4 C7 C13 C12 -87.7(6) . . . . ?
O9 C7 C13 C2 -35.5(8) . . . . ?
C4 C7 C13 C2 88.3(6) . . . . ?
C13 C2 C14 C15 -1.1(9) . . . . ?
C2 C14 C15 C17 0.0(9) . . . . ?
C14 C15 C17 C12 0.3(10) . . . . ?
C13 C12 C17 C15 0.5(10) . . . . ?

_diffrn_measured_fraction_theta_max    0.765
_diffrn_reflns_theta_full              27.00
_diffrn_measured_fraction_theta_full   0.765
_refine_diff_density_max    0.099
_refine_diff_density_min   -0.111
_refine_diff_density_rms    0.023