# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2009


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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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#  fide research purposes only. It may contain copyright material 
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data_theod27
_database_code_depnum_ccdc_archive 'CCDC 666543'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            AD11
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 N2 O4'
_chemical_formula_weight         278.30

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           tetragonal
_symmetry_space_group_name_H-M   P4(2)/n

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

_cell_length_a                   22.8916(12)
_cell_length_b                   22.8916(12)
_cell_length_c                   5.224(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2737.3(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    208(2)
_cell_measurement_reflns_used    289
_cell_measurement_theta_min      5.12
_cell_measurement_theta_max      23.56

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9803
_exptl_absorpt_correction_T_max  0.9950
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      208(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  Siemens
_diffrn_measurement_method       phi
_diffrn_reflns_number            7109
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         20.77
_reflns_number_total             1430
_reflns_number_gt                1317
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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^)+(0.0100P)^2^+5.1000P] 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         1430
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   1.346
_refine_ls_restrained_S_all      1.346
_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
C1 C -0.0387(2) 0.7567(2) 0.4430(9) 0.0374(13) Uani 1 1 d . . .
H1A H -0.0240 0.7171 0.4729 0.045 Uiso 1 1 calc R . .
H1B H -0.0528 0.7720 0.6069 0.045 Uiso 1 1 calc R . .
C2 C 0.0107(2) 0.79448(18) 0.3504(9) 0.0304(12) Uani 1 1 d . . .
H2 H 0.0435 0.7910 0.4730 0.036 Uiso 1 1 calc R . .
C3 C 0.0338(2) 0.78343(18) 0.0853(8) 0.0315(12) Uani 1 1 d . . .
H3 H 0.0000 0.7772 -0.0297 0.038 Uiso 1 1 calc R . .
C4 C 0.0741(2) 0.7315(2) 0.0595(10) 0.0462(14) Uani 1 1 d . . .
H4A H 0.0601 0.7000 0.1708 0.055 Uiso 1 1 calc R . .
H4B H 0.0727 0.7173 -0.1174 0.055 Uiso 1 1 calc R . .
C5 C 0.1354(2) 0.7449(3) 0.1263(10) 0.0516(15) Uani 1 1 d . . .
H5 H 0.1614 0.7134 0.1455 0.062 Uiso 1 1 calc R . .
C6 C 0.1557(2) 0.7974(3) 0.1605(10) 0.0529(15) Uani 1 1 d . . .
H6 H 0.1958 0.8016 0.1947 0.063 Uiso 1 1 calc R . .
C7 C 0.1194(2) 0.8514(2) 0.1489(10) 0.0426(13) Uani 1 1 d . . .
H7A H 0.1411 0.8816 0.0556 0.051 Uiso 1 1 calc R . .
H7B H 0.1129 0.8657 0.3235 0.051 Uiso 1 1 calc R . .
C8 C 0.06071(19) 0.84253(18) 0.0203(8) 0.0309(12) Uani 1 1 d . . .
H8 H 0.0637 0.8479 -0.1673 0.037 Uiso 1 1 calc R . .
C9 C 0.01578(19) 0.88350(19) 0.1346(8) 0.0303(12) Uani 1 1 d . . .
H9 H 0.0354 0.9196 0.1929 0.036 Uiso 1 1 calc R . .
C10 C -0.0193(2) 0.9418(2) -0.2204(9) 0.0298(12) Uani 1 1 d . . .
C11 C -0.08364(19) 0.86934(19) -0.0568(9) 0.0322(12) Uani 1 1 d . . .
H11 H -0.0904 0.8397 0.0640 0.039 Uiso 1 1 calc R . .
C12 C -0.12470(19) 0.88054(18) -0.2287(9) 0.0295(12) Uani 1 1 d . . .
C13 C -0.1155(2) 0.9279(2) -0.4056(9) 0.0311(12) Uani 1 1 d . . .
C14 C -0.1793(2) 0.8449(2) -0.2493(10) 0.0431(13) Uani 1 1 d . . .
H14A H -0.1807 0.8168 -0.1103 0.065 Uiso 1 1 calc R . .
H14B H -0.1796 0.8243 -0.4117 0.065 Uiso 1 1 calc R . .
H14C H -0.2131 0.8704 -0.2395 0.065 Uiso 1 1 calc R . .
N1 N -0.03185(15) 0.89899(15) -0.0472(7) 0.0283(10) Uani 1 1 d . . .
N2 N -0.06325(16) 0.95625(17) -0.3808(8) 0.0303(10) Uani 1 1 d . . .
O1 O -0.08563(14) 0.75395(13) 0.2713(6) 0.0408(9) Uani 1 1 d . . .
H1 H -0.0839 0.7229 0.1893 0.061 Uiso 1 1 calc R . .
O2 O -0.00857(13) 0.85455(12) 0.3474(5) 0.0318(8) Uani 1 1 d . . .
O3 O 0.02897(14) 0.96457(13) -0.2314(6) 0.0379(9) Uani 1 1 d . . .
O4 O -0.15044(14) 0.94404(15) -0.5680(7) 0.0489(10) Uani 1 1 d . . .
H1C H -0.0527(18) 0.9854(19) -0.498(9) 0.037(14) 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
C1 0.052(3) 0.034(3) 0.025(3) 0.000(2) -0.013(3) -0.002(2)
C2 0.042(3) 0.024(3) 0.025(3) -0.001(2) -0.014(2) 0.001(2)
C3 0.044(3) 0.034(3) 0.016(3) -0.009(2) -0.004(2) 0.004(2)
C4 0.057(4) 0.044(3) 0.037(3) -0.005(3) -0.005(3) 0.012(3)
C5 0.051(4) 0.064(4) 0.039(3) -0.003(3) -0.004(3) 0.024(3)
C6 0.040(3) 0.082(5) 0.036(3) -0.003(3) -0.004(3) 0.008(3)
C7 0.040(3) 0.055(3) 0.033(3) -0.003(3) -0.003(3) -0.006(3)
C8 0.037(3) 0.040(3) 0.015(2) 0.000(2) 0.000(2) -0.002(2)
C9 0.043(3) 0.031(3) 0.016(3) 0.003(2) -0.005(2) -0.007(2)
C10 0.036(3) 0.029(3) 0.025(3) -0.003(3) -0.004(3) 0.001(2)
C11 0.034(3) 0.030(3) 0.033(3) 0.001(2) 0.003(3) -0.003(2)
C12 0.028(3) 0.030(3) 0.030(3) -0.005(2) 0.000(2) 0.003(2)
C13 0.035(3) 0.036(3) 0.022(3) -0.005(2) -0.005(3) 0.008(2)
C14 0.043(3) 0.043(3) 0.044(3) 0.001(3) -0.002(3) 0.001(2)
N1 0.037(2) 0.026(2) 0.022(2) 0.0025(19) -0.0014(19) -0.0020(19)
N2 0.035(3) 0.028(2) 0.028(2) 0.004(2) -0.004(2) -0.003(2)
O1 0.052(2) 0.035(2) 0.035(2) -0.0017(16) -0.0111(18) -0.0072(16)
O2 0.048(2) 0.0260(18) 0.0214(18) -0.0047(15) 0.0004(15) -0.0035(14)
O3 0.041(2) 0.037(2) 0.035(2) 0.0073(16) -0.0076(17) -0.0095(17)
O4 0.039(2) 0.060(2) 0.048(2) 0.018(2) -0.016(2) -0.0005(17)

_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
C1 O1 1.400(5) . ?
C1 C2 1.504(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C2 O2 1.444(5) . ?
C2 C3 1.503(6) . ?
C2 H2 0.9900 . ?
C3 C4 1.512(6) . ?
C3 C8 1.525(6) . ?
C3 H3 0.9900 . ?
C4 C5 1.477(7) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C6 1.302(7) . ?
C5 H5 0.9400 . ?
C6 C7 1.491(7) . ?
C6 H6 0.9400 . ?
C7 C8 1.516(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C9 1.515(6) . ?
C8 H8 0.9900 . ?
C9 O2 1.409(5) . ?
C9 N1 1.489(5) . ?
C9 H9 0.9900 . ?
C10 O3 1.224(5) . ?
C10 N2 1.350(6) . ?
C10 N1 1.364(5) . ?
C11 C12 1.325(6) . ?
C11 N1 1.367(5) . ?
C11 H11 0.9400 . ?
C12 C13 1.440(6) . ?
C12 C14 1.497(6) . ?
C13 O4 1.223(5) . ?
C13 N2 1.368(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
N2 H1C 0.94(5) . ?
O1 H1 0.8300 . ?

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 C1 C2 113.4(4) . . ?
O1 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
O1 C1 H1B 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
O2 C2 C3 104.9(3) . . ?
O2 C2 C1 108.6(4) . . ?
C3 C2 C1 117.6(4) . . ?
O2 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
C2 C3 C4 115.4(4) . . ?
C2 C3 C8 101.4(3) . . ?
C4 C3 C8 115.5(4) . . ?
C2 C3 H3 108.0 . . ?
C4 C3 H3 108.0 . . ?
C8 C3 H3 108.0 . . ?
C5 C4 C3 113.3(4) . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 124.3(5) . . ?
C6 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
C5 C6 C7 124.1(5) . . ?
C5 C6 H6 117.9 . . ?
C7 C6 H6 117.9 . . ?
C6 C7 C8 113.6(4) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 110.1(4) . . ?
C9 C8 C3 100.8(3) . . ?
C7 C8 C3 112.3(4) . . ?
C9 C8 H8 111.1 . . ?
C7 C8 H8 111.1 . . ?
C3 C8 H8 111.1 . . ?
O2 C9 N1 109.0(3) . . ?
O2 C9 C8 106.8(3) . . ?
N1 C9 C8 113.2(3) . . ?
O2 C9 H9 109.3 . . ?
N1 C9 H9 109.3 . . ?
C8 C9 H9 109.3 . . ?
O3 C10 N2 122.6(4) . . ?
O3 C10 N1 121.8(4) . . ?
N2 C10 N1 115.6(4) . . ?
C12 C11 N1 123.0(4) . . ?
C12 C11 H11 118.5 . . ?
N1 C11 H11 118.5 . . ?
C11 C12 C13 118.5(4) . . ?
C11 C12 C14 122.4(4) . . ?
C13 C12 C14 119.1(4) . . ?
O4 C13 N2 119.6(4) . . ?
O4 C13 C12 125.3(4) . . ?
N2 C13 C12 115.1(4) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 N1 C11 121.0(4) . . ?
C10 N1 C9 116.1(4) . . ?
C11 N1 C9 122.7(4) . . ?
C10 N2 C13 126.4(4) . . ?
C10 N2 H1C 113(3) . . ?
C13 N2 H1C 120(3) . . ?
C1 O1 H1 109.5 . . ?
C9 O2 C2 109.6(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O4 0.83 1.89 2.684(4) 160.2 7_465
N2 H1C O3 0.94(5) 1.90(5) 2.829(5) 172(4) 5_574

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        20.77
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.043