Supplementary Material (ESI) for Chemical Communications
This journal is (c) The Royal Society of Chemistry 2003

data_03032
_database_code_CSD               214215

_exptl_crystal_id                MSC03032
_audit_creation_date             02/12/2003

_chemical_formula_structural     C17H21NO3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 N O3'
_chemical_formula_weight         287.35

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   'C2   '

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

_cell_length_a                   21.75(2)
_cell_length_b                   5.316(5)
_cell_length_c                   12.868(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.12(4)
_cell_angle_gamma                90.00
_cell_volume                     1487(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    137(2)
_cell_measurement_reflns_used    297
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      22.87

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_max          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      137(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_details      
'   0.30 degree frames measured for  64.59 seconds each'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_device       'three-circle goniometer with fixed chi'
_diffrn_measurement_device_type  'Bruker Platform goniometer'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker SMART 6000'
_diffrn_detector_area_resol_mean 44.52
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            9184
_diffrn_reflns_av_R_equivalents  0.3471
_diffrn_reflns_av_sigmaI/netI    0.5230
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         27.92
_reflns_number_total             3511
_reflns_number_gt                844
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1999)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999), XTEL (local package)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0466P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(5)
_refine_ls_number_reflns         3511
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.3102
_refine_ls_R_factor_gt           0.0892
_refine_ls_wR_factor_ref         0.2262
_refine_ls_wR_factor_gt          0.1618
_refine_ls_goodness_of_fit_ref   0.760
_refine_ls_restrained_S_all      0.760
_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
O1 O 0.3445(3) 0.0440(11) 0.0511(5) 0.0472(18) Uani 1 1 d . . .
C2 C 0.2970(4) -0.0176(18) 0.0868(6) 0.034(2) Uani 1 1 d . . .
O3 O 0.2444(3) 0.0944(11) 0.0584(4) 0.0378(15) Uani 1 1 d . . .
C4 C 0.1947(4) -0.0022(16) 0.1146(6) 0.036(2) Uani 1 1 d . . .
H22 H 0.1611 -0.0549 0.0664 0.044 Uiso 1 1 calc R . .
H23 H 0.1786 0.1276 0.1620 0.044 Uiso 1 1 calc R . .
C5 C 0.2191(3) -0.2301(16) 0.1773(6) 0.026(2) Uani 1 1 d . . .
H24 H 0.2038 -0.3897 0.1447 0.031 Uiso 1 1 calc R . .
N6 N 0.2842(3) -0.2004(14) 0.1587(5) 0.0307(17) Uani 1 1 d . . .
C7 C 0.3216(4) -0.396(2) 0.1893(7) 0.036(2) Uani 1 1 d . . .
O8 O 0.3014(3) -0.5688(12) 0.2365(5) 0.0448(18) Uani 1 1 d . . .
C9 C 0.3903(3) -0.377(2) 0.1727(7) 0.041(3) Uani 1 1 d . . .
H26 H 0.4030 -0.5167 0.1269 0.050 Uiso 1 1 calc R . .
H25 H 0.3991 -0.2174 0.1365 0.050 Uiso 1 1 calc R . .
C10 C 0.4272(4) -0.387(2) 0.2687(7) 0.048(3) Uani 1 1 d . . .
H27 H 0.4153 -0.5421 0.3077 0.058 Uiso 1 1 calc R . .
C11 C 0.4100(5) -0.156(3) 0.3348(10) 0.097(5) Uani 1 1 d . . .
H28 H 0.4140 -0.0031 0.2930 0.146 Uiso 1 1 calc R . .
H30 H 0.4376 -0.1459 0.3958 0.146 Uiso 1 1 calc R . .
H29 H 0.3674 -0.1728 0.3576 0.146 Uiso 1 1 calc R . .
C12 C 0.4946(4) -0.403(2) 0.2472(7) 0.053(3) Uani 1 1 d . . .
H31 H 0.5004 -0.5483 0.1991 0.064 Uiso 1 1 calc R . .
C13 C 0.5307(4) -0.463(2) 0.3478(8) 0.083(4) Uani 1 1 d . . .
H33 H 0.5747 -0.4697 0.3334 0.124 Uiso 1 1 calc R . .
H34 H 0.5173 -0.6261 0.3748 0.124 Uiso 1 1 calc R . .
H32 H 0.5230 -0.3319 0.3995 0.124 Uiso 1 1 calc R . .
C14 C 0.5209(4) -0.188(3) 0.1992(10) 0.078(4) Uani 1 1 d . . .
H35 H 0.5220 -0.0388 0.2396 0.093 Uiso 1 1 calc R . .
C15 C 0.5441(5) -0.172(4) 0.1043(10) 0.154(8) Uani 1 1 d . . .
H37 H 0.5443 -0.3150 0.0602 0.185 Uiso 1 1 calc R . .
H36 H 0.5605 -0.0166 0.0808 0.185 Uiso 1 1 calc R . .
C16 C 0.2020(3) -0.2221(18) 0.2860(6) 0.028(2) Uani 1 1 d . . .
C17 C 0.2190(3) -0.0379(15) 0.3534(6) 0.0232(19) Uani 1 1 d . . .
H39 H 0.2459 0.0897 0.3297 0.028 Uiso 1 1 calc R . .
C18 C 0.1996(4) -0.0257(16) 0.4524(7) 0.033(2) Uani 1 1 d . . .
H40 H 0.2117 0.1108 0.4959 0.040 Uiso 1 1 calc R . .
C19 C 0.1624(4) -0.2123(19) 0.4896(6) 0.035(2) Uani 1 1 d . . .
H41 H 0.1493 -0.2093 0.5595 0.042 Uiso 1 1 calc R . .
C20 C 0.1444(4) -0.405(2) 0.4234(7) 0.042(2) Uani 1 1 d . . .
H42 H 0.1188 -0.5363 0.4479 0.050 Uiso 1 1 calc R . .
C21 C 0.1633(3) -0.4057(19) 0.3226(7) 0.034(2) Uani 1 1 d . . .
H43 H 0.1496 -0.5354 0.2770 0.041 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 0.042(4) 0.035(4) 0.066(5) 0.009(4) 0.020(3) 0.001(3)
C2 0.042(6) 0.034(6) 0.025(5) 0.005(5) 0.007(4) 0.014(5)
O3 0.043(4) 0.036(4) 0.034(3) 0.011(4) 0.003(3) 0.006(4)
C4 0.037(5) 0.037(7) 0.037(5) 0.007(5) 0.011(4) 0.005(5)
C5 0.026(5) 0.013(5) 0.038(5) -0.004(5) -0.012(4) -0.005(4)
N6 0.027(4) 0.029(4) 0.037(4) 0.007(4) 0.005(3) 0.002(4)
C7 0.027(5) 0.056(7) 0.025(5) -0.009(6) 0.006(4) -0.001(6)
O8 0.034(4) 0.042(5) 0.059(5) 0.019(4) 0.015(3) 0.004(3)
C9 0.033(5) 0.052(7) 0.039(6) 0.022(5) 0.011(4) 0.012(5)
C10 0.035(5) 0.062(7) 0.047(6) -0.010(6) 0.005(4) 0.002(6)
C11 0.035(6) 0.133(14) 0.124(11) -0.075(10) 0.001(7) -0.026(7)
C12 0.031(5) 0.077(9) 0.051(6) 0.002(6) -0.004(5) 0.012(6)
C13 0.047(7) 0.105(11) 0.096(9) -0.005(9) -0.016(6) 0.000(7)
C14 0.038(7) 0.107(12) 0.088(10) 0.008(9) -0.003(6) -0.003(7)
C15 0.050(8) 0.34(3) 0.074(10) 0.039(14) -0.003(8) -0.011(12)
C16 0.021(5) 0.030(6) 0.034(5) 0.006(5) 0.001(4) 0.012(5)
C17 0.024(4) 0.023(5) 0.023(5) -0.002(4) -0.003(3) -0.009(4)
C18 0.036(5) 0.021(5) 0.043(6) -0.003(5) -0.001(4) -0.003(5)
C19 0.035(5) 0.038(6) 0.031(5) 0.003(6) 0.013(4) 0.010(5)
C20 0.030(5) 0.048(7) 0.048(6) -0.001(6) 0.012(4) -0.004(6)
C21 0.022(5) 0.026(6) 0.054(6) -0.001(5) -0.002(4) -0.004(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 C2 1.184(9) . ?
C2 O3 1.334(9) . ?
C2 N6 1.374(10) . ?
O3 C4 1.408(8) . ?
C4 C5 1.543(11) . ?
C5 N6 1.450(9) . ?
C5 C16 1.456(10) . ?
N6 C7 1.371(11) . ?
C7 O8 1.190(11) . ?
C7 C9 1.518(10) . ?
C9 C10 1.461(11) . ?
C10 C12 1.498(11) . ?
C10 C11 1.545(14) . ?
C12 C14 1.423(16) . ?
C12 C13 1.534(12) . ?
C14 C15 1.334(14) . ?
C16 C17 1.354(11) . ?
C16 C21 1.377(11) . ?
C17 C18 1.352(10) . ?
C18 C19 1.372(11) . ?
C19 C20 1.384(13) . ?
C20 C21 1.369(11) . ?

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
O1 C2 O3 121.3(8) . . ?
O1 C2 N6 130.3(8) . . ?
O3 C2 N6 108.5(7) . . ?
C2 O3 C4 111.0(7) . . ?
O3 C4 C5 107.2(6) . . ?
N6 C5 C16 115.0(6) . . ?
N6 C5 C4 98.9(6) . . ?
C16 C5 C4 112.9(8) . . ?
C7 N6 C2 127.1(7) . . ?
C7 N6 C5 116.4(7) . . ?
C2 N6 C5 113.5(7) . . ?
O8 C7 N6 120.7(7) . . ?
O8 C7 C9 119.7(9) . . ?
N6 C7 C9 119.3(9) . . ?
C10 C9 C7 113.9(7) . . ?
C9 C10 C12 111.7(7) . . ?
C9 C10 C11 107.5(9) . . ?
C12 C10 C11 113.2(9) . . ?
C14 C12 C10 116.0(10) . . ?
C14 C12 C13 109.3(9) . . ?
C10 C12 C13 110.0(8) . . ?
C15 C14 C12 127.9(16) . . ?
C17 C16 C21 117.0(8) . . ?
C17 C16 C5 124.4(8) . . ?
C21 C16 C5 118.4(9) . . ?
C18 C17 C16 123.5(8) . . ?
C17 C18 C19 119.4(8) . . ?
C18 C19 C20 118.9(8) . . ?
C21 C20 C19 119.9(9) . . ?
C20 C21 C16 121.3(9) . . ?

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
O1 C2 O3 C4 -177.3(9) . . . . ?
N6 C2 O3 C4 2.9(9) . . . . ?
C2 O3 C4 C5 -7.9(9) . . . . ?
O3 C4 C5 N6 9.2(8) . . . . ?
O3 C4 C5 C16 131.2(7) . . . . ?
O1 C2 N6 C7 -16.4(16) . . . . ?
O3 C2 N6 C7 163.4(8) . . . . ?
O1 C2 N6 C5 -176.0(10) . . . . ?
O3 C2 N6 C5 3.9(9) . . . . ?
C16 C5 N6 C7 69.7(10) . . . . ?
C4 C5 N6 C7 -169.9(7) . . . . ?
C16 C5 N6 C2 -128.5(8) . . . . ?
C4 C5 N6 C2 -8.0(8) . . . . ?
C2 N6 C7 O8 -165.3(8) . . . . ?
C5 N6 C7 O8 -6.3(12) . . . . ?
C2 N6 C7 C9 21.2(13) . . . . ?
C5 N6 C7 C9 -179.7(8) . . . . ?
O8 C7 C9 C10 -54.7(14) . . . . ?
N6 C7 C9 C10 118.8(9) . . . . ?
C7 C9 C10 C12 172.4(10) . . . . ?
C7 C9 C10 C11 -62.8(11) . . . . ?
C9 C10 C12 C14 66.0(14) . . . . ?
C11 C10 C12 C14 -55.5(13) . . . . ?
C9 C10 C12 C13 -169.4(9) . . . . ?
C11 C10 C12 C13 69.1(14) . . . . ?
C10 C12 C14 C15 -113.7(13) . . . . ?
C13 C12 C14 C15 121.3(13) . . . . ?
N6 C5 C16 C17 51.3(11) . . . . ?
C4 C5 C16 C17 -61.1(10) . . . . ?
N6 C5 C16 C21 -132.4(7) . . . . ?
C4 C5 C16 C21 115.2(9) . . . . ?
C21 C16 C17 C18 -0.5(12) . . . . ?
C5 C16 C17 C18 175.9(8) . . . . ?
C16 C17 C18 C19 2.2(13) . . . . ?
C17 C18 C19 C20 -1.7(12) . . . . ?
C18 C19 C20 C21 -0.4(12) . . . . ?
C19 C20 C21 C16 2.2(13) . . . . ?
C17 C16 C21 C20 -1.7(12) . . . . ?
C5 C16 C21 C20 -178.3(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.92
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.060