Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2001

data_ak0101 

_database_code_CSD	169817


_journal_coden_Cambridge      182

_publ_requested_journal       'Chemical Communications'

loop_
_publ_author_name
'Bond, Andrew'
'Kirby, Anthony J.'
'Rodriguez, Encina'

_publ_contact_author_name     	'Prof Anthony J. Kirby'  
_publ_contact_author_address 
;
Chemistry
University of Cambridge
University Chemical Laborataory
Cambridge
CB2 1EW
UNITED KINGDOM
;

_publ_contact_author_email       'AJK1@CAM.AC.UK'

_publ_section_title		
;
Efficient Intramolecular General Acid Catalysis: a Preview from a Crystal 
Structure.
;


_audit_creation_method            SHELXL-97 
_chemical_name_systematic         ?
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C13 H17 N O5'
_chemical_formula_sum             'C13 H17 N O5' 
_chemical_formula_weight          267.28 

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    P2(1)/n

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

_cell_length_a                    11.5493(8) 
_cell_length_b                    8.4256(4) 
_cell_length_c                    13.4272(11) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  98.756(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1291.37(15) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     180(2) 
_cell_measurement_reflns_used     5886
_cell_measurement_theta_min       1.00 
_cell_measurement_theta_max       27.48 

_exptl_crystal_description        needle 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.46 
_exptl_crystal_size_mid           0.12 
_exptl_crystal_size_min           0.12 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.375 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              568 
_exptl_absorpt_coefficient_mu     0.106 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.846
_exptl_absorpt_correction_T_max   1.906
_exptl_absorpt_process_details    'Sortav Blessing (1995)'

_exptl_special_details 
; 
H(2O) (associated with intramolecular hydrogen bond) located in difference
Fourier and refined without restraint.
; 

_diffrn_ambient_temperature       180(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 Kappa CCD'
_diffrn_measurement_method        'Thin slice \w and \f scans'
_diffrn_standards_number          0
_diffrn_reflns_number             6633 
_diffrn_reflns_av_R_equivalents   0.0817 
_diffrn_reflns_av_sigmaI/netI     0.0714 
_diffrn_reflns_limit_h_min        -14 
_diffrn_reflns_limit_h_max        14 
_diffrn_reflns_limit_k_min        -10 
_diffrn_reflns_limit_k_max        10 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        17 
_diffrn_reflns_theta_min          3.57 
_diffrn_reflns_theta_max          27.44 
_diffrn_measured_fraction_theta_max    0.955 
_diffrn_reflns_theta_full              27.44 
_diffrn_measured_fraction_theta_full   0.955 
_reflns_number_total              2812
_reflns_number_gt                 1994 
_reflns_threshold_expression      >2sigma(I) 

_computing_data_collection        'Collect (Nonius B.V. 1998)'
_computing_cell_refinement        'HKL Scalepack (Otwinowski & Minor 1997)' 
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution     'SHELXS-97 (Sheldrick 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick 1997)' 
_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^)+(0.1225P)^2^+0.9024P] 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          2812 
_refine_ls_number_parameters      178 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1104 
_refine_ls_R_factor_gt            0.0819 
_refine_ls_wR_factor_ref          0.2505 
_refine_ls_wR_factor_gt           0.2292 
_refine_ls_goodness_of_fit_ref    1.087 
_refine_ls_restrained_S_all       1.087 
_refine_ls_shift/su_max           0.003 
_refine_ls_shift/su_mean          0.001 
_refine_diff_density_max          0.451 
_refine_diff_density_min          -0.505 
_refine_diff_density_rms          0.101 

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 0.4412(2) -0.0324(3) 0.84024(17) 0.0499(6) Uani 1 1 d . . . 
O2 O 0.8169(2) -0.0083(3) 1.0000(2) 0.0610(7) Uani 1 1 d . . . 
H2O H 0.801(4) 0.094(6) 0.989(3) 0.078(14) Uiso 1 1 d . . . 
O3 O 0.7366(3) -0.2445(3) 0.9950(2) 0.0645(8) Uani 1 1 d . . . 
O4 O 0.76614(19) 0.2768(2) 0.92731(16) 0.0445(6) Uani 1 1 d . . . 
O5 O 0.9080(2) 0.3951(3) 0.8445(2) 0.0645(8) Uani 1 1 d . . . 
N1 N 0.5278(2) -0.1271(3) 0.8964(2) 0.0488(7) Uani 1 1 d . . . 
C1 C 0.4873(3) 0.1125(3) 0.8306(2) 0.0426(7) Uani 1 1 d . . . 
C2 C 0.4352(3) 0.2529(4) 0.7723(2) 0.0467(8) Uani 1 1 d . . . 
C3 C 0.5241(3) 0.2897(4) 0.6988(2) 0.0489(8) Uani 1 1 d . . . 
H3A H 0.5238 0.2010 0.6504 0.059 Uiso 1 1 calc R . . 
H3B H 0.4989 0.3869 0.6600 0.059 Uiso 1 1 calc R . . 
C4 C 0.6491(3) 0.3135(4) 0.7547(2) 0.0449(7) Uani 1 1 d . . . 
H4A H 0.6748 0.4238 0.7450 0.054 Uiso 1 1 calc R . . 
H4B H 0.7034 0.2407 0.7269 0.054 Uiso 1 1 calc R . . 
C5 C 0.6523(3) 0.2798(3) 0.8690(2) 0.0370(6) Uani 1 1 d . . . 
C6 C 0.5714(3) 0.4007(3) 0.9106(2) 0.0474(8) Uani 1 1 d . . . 
H6A H 0.5687 0.3780 0.9826 0.057 Uiso 1 1 calc R . . 
H6B H 0.6027 0.5093 0.9055 0.057 Uiso 1 1 calc R . . 
C7 C 0.4472(3) 0.3906(4) 0.8504(3) 0.0556(9) Uani 1 1 d . . . 
H7A H 0.4280 0.4922 0.8147 0.067 Uiso 1 1 calc R . . 
H7B H 0.3902 0.3743 0.8976 0.067 Uiso 1 1 calc R . . 
C8 C 0.5977(3) 0.1200(3) 0.8772(2) 0.0362(6) Uani 1 1 d . . . 
C9 C 0.6200(3) -0.0341(3) 0.9172(2) 0.0378(7) Uani 1 1 d . . . 
C10 C 0.3109(3) 0.2292(5) 0.7201(3) 0.0664(10) Uani 1 1 d . . . 
H10A H 0.2606 0.2020 0.7701 0.100 Uiso 1 1 calc R . . 
H10B H 0.3090 0.1430 0.6709 0.100 Uiso 1 1 calc R . . 
H10C H 0.2827 0.3273 0.6854 0.100 Uiso 1 1 calc R . . 
C11 C 0.8418(3) 0.4088(4) 0.9216(3) 0.0525(8) Uani 1 1 d . . . 
H11A H 0.7942 0.5067 0.9115 0.063 Uiso 1 1 calc R . . 
H11B H 0.8951 0.4190 0.9864 0.063 Uiso 1 1 calc R . . 
C12 C 0.9917(4) 0.2726(5) 0.8615(4) 0.0801(13) Uani 1 1 d . . . 
H12A H 1.0392 0.2716 0.8069 0.120 Uiso 1 1 calc R . . 
H12B H 0.9516 0.1704 0.8635 0.120 Uiso 1 1 calc R . . 
H12C H 1.0424 0.2906 0.9259 0.120 Uiso 1 1 calc R . . 
C13 C 0.7280(3) -0.1061(3) 0.9743(2) 0.0440(7) Uani 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 0.0547(13) 0.0431(12) 0.0521(13) 0.0027(10) 0.0086(10) -0.0098(10) 
O2 0.0630(15) 0.0435(14) 0.0717(17) 0.0111(12) -0.0052(12) -0.0025(11) 
O3 0.0849(19) 0.0344(13) 0.0746(18) 0.0128(11) 0.0138(14) 0.0056(11) 
O4 0.0534(12) 0.0361(11) 0.0436(12) 0.0035(9) 0.0062(9) -0.0087(9) 
O5 0.0676(16) 0.0586(16) 0.0729(17) 0.0250(13) 0.0285(13) 0.0029(12) 
N1 0.0637(17) 0.0378(14) 0.0465(15) 0.0035(11) 0.0139(12) -0.0083(12) 
C1 0.0509(17) 0.0399(16) 0.0381(15) -0.0002(12) 0.0103(13) -0.0038(12) 
C2 0.0495(17) 0.0472(18) 0.0441(17) 0.0071(13) 0.0095(14) 0.0049(13) 
C3 0.066(2) 0.0447(17) 0.0367(16) 0.0083(13) 0.0096(14) 0.0057(15) 
C4 0.0602(19) 0.0397(16) 0.0376(15) 0.0054(12) 0.0163(13) 0.0023(13) 
C5 0.0481(16) 0.0325(13) 0.0314(14) -0.0007(11) 0.0096(12) -0.0012(11) 
C6 0.067(2) 0.0331(15) 0.0454(17) -0.0059(13) 0.0195(15) 0.0020(14) 
C7 0.062(2) 0.049(2) 0.060(2) -0.0017(16) 0.0249(17) 0.0109(15) 
C8 0.0502(16) 0.0308(13) 0.0291(13) -0.0011(10) 0.0110(11) -0.0023(11) 
C9 0.0547(17) 0.0286(13) 0.0325(14) -0.0029(11) 0.0142(12) -0.0038(11) 
C10 0.060(2) 0.074(3) 0.065(2) 0.009(2) 0.0059(18) 0.0040(18) 
C11 0.062(2) 0.0332(16) 0.064(2) 0.0000(14) 0.0137(16) -0.0106(14) 
C12 0.072(3) 0.071(3) 0.105(4) 0.026(3) 0.039(3) 0.015(2) 
C13 0.0631(19) 0.0342(16) 0.0377(15) 0.0006(12) 0.0169(13) 0.0001(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 
O1 C1 1.346(4) . ? 
O1 N1 1.405(4) . ? 
O2 C13 1.321(4) . ? 
O2 H2O 0.89(5) . ? 
O3 C13 1.199(4) . ? 
O4 C11 1.424(3) . ? 
O4 C5 1.425(4) . ? 
O5 C11 1.383(4) . ? 
O5 C12 1.409(5) . ? 
N1 C9 1.318(4) . ? 
C1 C8 1.334(4) . ? 
C1 C2 1.493(4) . ? 
C2 C10 1.511(5) . ? 
C2 C7 1.555(5) . ? 
C2 C3 1.560(5) . ? 
C3 C4 1.536(5) . ? 
C3 H3A 0.9900 . ? 
C3 H3B 0.9900 . ? 
C4 C5 1.556(4) . ? 
C4 H4A 0.9900 . ? 
C4 H4B 0.9900 . ? 
C5 C8 1.498(4) . ? 
C5 C6 1.544(4) . ? 
C6 C7 1.538(5) . ? 
C6 H6A 0.9900 . ? 
C6 H6B 0.9900 . ? 
C7 H7A 0.9900 . ? 
C7 H7B 0.9900 . ? 
C8 C9 1.413(4) . ? 
C9 C13 1.490(4) . ? 
C10 H10A 0.9800 . ? 
C10 H10B 0.9800 . ? 
C10 H10C 0.9800 . ? 
C11 H11A 0.9900 . ? 
C11 H11B 0.9900 . ? 
C12 H12A 0.9800 . ? 
C12 H12B 0.9800 . ? 
C12 H12C 0.9800 . ? 

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 
C1 O1 N1 107.9(2) . . ? 
C13 O2 H2O 115(3) . . ? 
C11 O4 C5 118.6(2) . . ? 
C11 O5 C12 112.5(3) . . ? 
C9 N1 O1 105.2(2) . . ? 
C8 C1 O1 111.1(3) . . ? 
C8 C1 C2 119.3(3) . . ? 
O1 C1 C2 129.5(3) . . ? 
C1 C2 C10 114.6(3) . . ? 
C1 C2 C7 104.5(3) . . ? 
C10 C2 C7 113.1(3) . . ? 
C1 C2 C3 103.7(2) . . ? 
C10 C2 C3 113.7(3) . . ? 
C7 C2 C3 106.2(3) . . ? 
C4 C3 C2 112.1(2) . . ? 
C4 C3 H3A 109.2 . . ? 
C2 C3 H3A 109.2 . . ? 
C4 C3 H3B 109.2 . . ? 
C2 C3 H3B 109.2 . . ? 
H3A C3 H3B 107.9 . . ? 
C3 C4 C5 109.7(2) . . ? 
C3 C4 H4A 109.7 . . ? 
C5 C4 H4A 109.7 . . ? 
C3 C4 H4B 109.7 . . ? 
C5 C4 H4B 109.7 . . ? 
H4A C4 H4B 108.2 . . ? 
O4 C5 C8 107.8(2) . . ? 
O4 C5 C6 111.8(2) . . ? 
C8 C5 C6 106.4(2) . . ? 
O4 C5 C4 115.3(2) . . ? 
C8 C5 C4 106.8(2) . . ? 
C6 C5 C4 108.2(2) . . ? 
C7 C6 C5 109.9(2) . . ? 
C7 C6 H6A 109.7 . . ? 
C5 C6 H6A 109.7 . . ? 
C7 C6 H6B 109.7 . . ? 
C5 C6 H6B 109.7 . . ? 
H6A C6 H6B 108.2 . . ? 
C6 C7 C2 112.1(3) . . ? 
C6 C7 H7A 109.2 . . ? 
C2 C7 H7A 109.2 . . ? 
C6 C7 H7B 109.2 . . ? 
C2 C7 H7B 109.2 . . ? 
H7A C7 H7B 107.9 . . ? 
C1 C8 C9 103.9(3) . . ? 
C1 C8 C5 113.0(2) . . ? 
C9 C8 C5 143.1(3) . . ? 
N1 C9 C8 111.8(3) . . ? 
N1 C9 C13 117.0(3) . . ? 
C8 C9 C13 131.3(3) . . ? 
C2 C10 H10A 109.5 . . ? 
C2 C10 H10B 109.5 . . ? 
H10A C10 H10B 109.5 . . ? 
C2 C10 H10C 109.5 . . ? 
H10A C10 H10C 109.5 . . ? 
H10B C10 H10C 109.5 . . ? 
O5 C11 O4 112.9(3) . . ? 
O5 C11 H11A 109.0 . . ? 
O4 C11 H11A 109.0 . . ? 
O5 C11 H11B 109.0 . . ? 
O4 C11 H11B 109.0 . . ? 
H11A C11 H11B 107.8 . . ? 
O5 C12 H12A 109.5 . . ? 
O5 C12 H12B 109.5 . . ? 
H12A C12 H12B 109.5 . . ? 
O5 C12 H12C 109.5 . . ? 
H12A C12 H12C 109.5 . . ? 
H12B C12 H12C 109.5 . . ? 
O3 C13 O2 120.8(3) . . ? 
O3 C13 C9 123.3(3) . . ? 
O2 C13 C9 115.9(3) . . ? 

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 
C1 O1 N1 C9 0.1(3) . . . . ? 
N1 O1 C1 C8 -0.5(3) . . . . ? 
N1 O1 C1 C2 175.4(3) . . . . ? 
C8 C1 C2 C10 178.2(3) . . . . ? 
O1 C1 C2 C10 2.5(5) . . . . ? 
C8 C1 C2 C7 -57.5(4) . . . . ? 
O1 C1 C2 C7 126.9(3) . . . . ? 
C8 C1 C2 C3 53.6(4) . . . . ? 
O1 C1 C2 C3 -122.1(3) . . . . ? 
C1 C2 C3 C4 -55.0(3) . . . . ? 
C10 C2 C3 C4 179.8(3) . . . . ? 
C7 C2 C3 C4 54.8(3) . . . . ? 
C2 C3 C4 C5 4.7(4) . . . . ? 
C11 O4 C5 C8 172.3(2) . . . . ? 
C11 O4 C5 C6 -71.1(3) . . . . ? 
C11 O4 C5 C4 53.0(3) . . . . ? 
C3 C4 C5 O4 171.9(2) . . . . ? 
C3 C4 C5 C8 52.1(3) . . . . ? 
C3 C4 C5 C6 -62.1(3) . . . . ? 
O4 C5 C6 C7 -175.6(2) . . . . ? 
C8 C5 C6 C7 -58.1(3) . . . . ? 
C4 C5 C6 C7 56.4(3) . . . . ? 
C5 C6 C7 C2 5.3(4) . . . . ? 
C1 C2 C7 C6 48.5(3) . . . . ? 
C10 C2 C7 C6 173.8(3) . . . . ? 
C3 C2 C7 C6 -60.8(3) . . . . ? 
O1 C1 C8 C9 0.7(3) . . . . ? 
C2 C1 C8 C9 -175.7(3) . . . . ? 
O1 C1 C8 C5 -179.6(2) . . . . ? 
C2 C1 C8 C5 4.0(4) . . . . ? 
O4 C5 C8 C1 175.8(2) . . . . ? 
C6 C5 C8 C1 55.7(3) . . . . ? 
C4 C5 C8 C1 -59.7(3) . . . . ? 
O4 C5 C8 C9 -4.7(5) . . . . ? 
C6 C5 C8 C9 -124.8(4) . . . . ? 
C4 C5 C8 C9 119.8(4) . . . . ? 
O1 N1 C9 C8 0.3(3) . . . . ? 
O1 N1 C9 C13 -178.1(2) . . . . ? 
C1 C8 C9 N1 -0.6(3) . . . . ? 
C5 C8 C9 N1 179.8(3) . . . . ? 
C1 C8 C9 C13 177.5(3) . . . . ? 
C5 C8 C9 C13 -2.0(6) . . . . ? 
C12 O5 C11 O4 -68.0(4) . . . . ? 
C5 O4 C11 O5 -88.0(3) . . . . ? 
N1 C9 C13 O3 5.7(4) . . . . ? 
C8 C9 C13 O3 -172.4(3) . . . . ? 
N1 C9 C13 O2 -175.8(3) . . . . ? 
C8 C9 C13 O2 6.1(5) . . . . ? 

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 
O2 H2O O4  0.89(5) 1.76(5) 2.625(3) 162(4) .