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

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Jesus Peregrina'
_publ_contact_author_email       JESUSMANUEL.PEREGRINA@UNIRIOJA.ES

_publ_section_title              
;
Stabilizing Unusual Conformations in Small Peptides
and Glucopeptides using a Hydroxylated Cyclobutane Amino Acid
;
loop_
_publ_author_name
'Jesus Peregrina'
'Alberto Avenoza'
'Jesus H Busto'
'Francisco Corzana'
'Alberto Fernandez-Tejada'

# Attachment 'compound1.cif'

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 716958'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H24 N4 O5, 2(O)'
_chemical_formula_sum            'C14 H28 N4 O7'
_chemical_formula_weight         360.36
_chemical_absolute_configuration syn

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   'P 21 21 21'

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

_cell_length_a                   7.8140(5)
_cell_length_b                   14.5374(8)
_cell_length_c                   16.0994(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1828.72(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5275
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prism
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.105
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16248
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.63
_diffrn_reflns_theta_max         28.25
_reflns_number_total             4471
_reflns_number_gt                2904
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius Kappa CCD'
_computing_cell_refinement       'Denzo and Scalepak (1997)'
_computing_data_reduction        'Denzo and Scalepak (1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP III'
_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^)+(0.0780P)^2^+0.8898P] 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   -0.6(19)
_refine_ls_number_reflns         4471
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1761
_refine_ls_wR_factor_gt          0.1490
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.4995(3) 0.51381(18) 0.54529(13) 0.0413(6) Uani 1 1 d . . .
O2 O 0.2387(3) 0.65488(16) 0.64680(15) 0.0434(6) Uani 1 1 d . . .
O3 O 0.1492(3) 0.63720(18) 0.30682(14) 0.0439(6) Uani 1 1 d . . .
N4 N 0.3897(4) 0.5839(2) 0.74735(18) 0.0344(6) Uani 1 1 d . . .
O5 O 0.6498(4) 0.39216(18) 0.72310(16) 0.0446(6) Uani 1 1 d . . .
N6 N 0.3070(4) 0.4485(2) 0.63143(18) 0.0348(6) Uani 1 1 d . . .
C7 C 0.6625(4) 0.4883(2) 0.7299(2) 0.0380(8) Uani 1 1 d . . .
N8 N 0.1148(3) 0.5363(2) 0.51042(16) 0.0343(6) Uani 1 1 d . . .
O9 O 0.1078(4) 0.40760(18) 0.43242(15) 0.0561(8) Uani 1 1 d . . .
C10 C 0.1464(4) 0.4469(3) 0.49787(19) 0.0377(8) Uani 1 1 d . . .
C11 C 0.1914(4) 0.6126(2) 0.37801(19) 0.0345(7) Uani 1 1 d . . .
N12 N 0.3513(4) 0.6054(2) 0.40163(17) 0.0443(8) Uani 1 1 d . . .
C13 C 0.6663(5) 0.6177(3) 0.6664(3) 0.0435(8) Uani 1 1 d . . .
C14 C 0.7927(5) 0.5354(3) 0.6743(3) 0.0484(10) Uani 1 1 d . . .
C15 C 0.5203(4) 0.5511(2) 0.6913(2) 0.0344(7) Uani 1 1 d . . .
C16 C 0.2306(5) 0.3920(2) 0.5664(2) 0.0388(8) Uani 1 1 d . . .
C17 C 0.4416(4) 0.5034(2) 0.61540(19) 0.0334(7) Uani 1 1 d . . .
C18 C 0.0521(5) 0.5942(3) 0.4429(2) 0.0397(8) Uani 1 1 d . . .
C19 C 0.2606(4) 0.6375(2) 0.7208(2) 0.0370(7) Uani 1 1 d . . .
C20 C 0.1015(6) 0.3262(3) 0.6060(3) 0.0536(10) Uani 1 1 d . . .
H20A H 0.1566 0.2916 0.6492 0.080 Uiso 1 1 calc R . .
H20B H 0.0584 0.2848 0.5645 0.080 Uiso 1 1 calc R . .
H20C H 0.0084 0.3608 0.6292 0.080 Uiso 1 1 calc R . .
C21 C 0.4960(5) 0.6224(4) 0.3479(2) 0.0560(10) Uani 1 1 d . . .
H21A H 0.6001 0.6128 0.3784 0.084 Uiso 1 1 calc R . .
H21B H 0.4919 0.6847 0.3283 0.084 Uiso 1 1 calc R . .
H21C H 0.4921 0.5811 0.3015 0.084 Uiso 1 1 calc R . .
C22 C 0.1441(5) 0.6769(3) 0.7864(2) 0.0522(10) Uani 1 1 d . . .
H22A H 0.1799 0.6558 0.8401 0.078 Uiso 1 1 calc R . .
H22B H 0.0287 0.6572 0.7761 0.078 Uiso 1 1 calc R . .
H22C H 0.1493 0.7429 0.7847 0.078 Uiso 1 1 calc R . .
C23 C -0.0195(6) 0.6837(3) 0.4768(2) 0.0550(11) Uani 1 1 d . . .
H23A H -0.1064 0.6706 0.5173 0.083 Uiso 1 1 calc R . .
H23B H -0.0681 0.7189 0.4322 0.083 Uiso 1 1 calc R . .
H23C H 0.0708 0.7184 0.5025 0.083 Uiso 1 1 calc R . .
O24 O 0.7139(7) 0.4167(3) 0.4191(3) 0.1094(14) Uani 1 1 d . . .
O25 O 0.6218(10) 0.2962(4) 0.5661(4) 0.155(2) Uani 1 1 d . . .
H18 H -0.037(4) 0.559(2) 0.4204(19) 0.026(8) Uiso 1 1 d . . .
H12 H 0.3779 0.5846 0.4517 0.065(13) Uiso 1 1 d . . .
H6 H 0.275(6) 0.432(3) 0.680(3) 0.065(14) Uiso 1 1 d . . .
H16 H 0.324(5) 0.360(3) 0.539(2) 0.040(10) Uiso 1 1 d . . .
H4 H 0.408(4) 0.580(2) 0.796(2) 0.028(9) Uiso 1 1 d . . .
H7 H 0.685(5) 0.511(2) 0.790(2) 0.035(9) Uiso 1 1 d . . .
H14A H 0.809(5) 0.493(3) 0.614(2) 0.047(10) Uiso 1 1 d . . .
H14B H 0.912(7) 0.544(4) 0.695(3) 0.078(15) Uiso 1 1 d . . .
H13A H 0.649(4) 0.655(2) 0.615(2) 0.030(9) Uiso 1 1 d . . .
H13B H 0.675(6) 0.669(3) 0.716(3) 0.062(13) Uiso 1 1 d . . .
H8 H 0.1555 0.5654 0.5599 0.057(12) Uiso 1 1 d . . .
H5 H 0.572(7) 0.373(4) 0.760(3) 0.071(15) 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 0.0369(12) 0.0580(16) 0.0291(11) 0.0049(10) 0.0060(10) 0.0025(12)
O2 0.0485(15) 0.0424(14) 0.0395(14) 0.0005(11) -0.0038(11) 0.0084(12)
O3 0.0465(14) 0.0542(15) 0.0312(11) 0.0059(11) -0.0039(11) -0.0053(12)
N4 0.0343(15) 0.0401(15) 0.0288(14) -0.0013(12) 0.0027(12) 0.0030(12)
O5 0.0454(14) 0.0419(14) 0.0465(14) 0.0039(12) 0.0013(12) 0.0073(12)
N6 0.0401(16) 0.0388(15) 0.0254(13) 0.0019(12) 0.0027(12) -0.0015(12)
C7 0.0307(17) 0.0436(19) 0.0397(18) 0.0023(16) -0.0035(14) 0.0028(15)
N8 0.0337(15) 0.0423(16) 0.0268(13) 0.0014(12) 0.0017(11) -0.0024(12)
O9 0.084(2) 0.0517(16) 0.0324(12) -0.0037(12) -0.0107(13) -0.0094(15)
C10 0.0420(18) 0.0431(19) 0.0281(15) -0.0003(15) 0.0028(15) -0.0082(16)
C11 0.0403(18) 0.0344(17) 0.0290(15) 0.0006(14) 0.0007(13) -0.0017(14)
N12 0.0366(16) 0.061(2) 0.0352(15) 0.0092(14) 0.0030(13) -0.0053(15)
C13 0.0383(19) 0.0396(19) 0.053(2) 0.0018(18) 0.0030(17) -0.0040(16)
C14 0.0288(18) 0.058(2) 0.058(2) 0.003(2) -0.0004(17) -0.0006(17)
C15 0.0299(16) 0.0382(18) 0.0350(15) 0.0024(14) 0.0008(13) 0.0005(15)
C16 0.0435(19) 0.0395(18) 0.0333(17) -0.0069(15) -0.0010(15) -0.0031(17)
C17 0.0319(16) 0.0397(18) 0.0286(15) 0.0065(14) 0.0020(13) 0.0062(14)
C18 0.0320(17) 0.049(2) 0.0383(18) 0.0059(16) -0.0038(14) -0.0053(16)
C19 0.0373(18) 0.0338(16) 0.0400(18) -0.0002(15) -0.0003(15) 0.0012(14)
C20 0.064(3) 0.045(2) 0.052(2) 0.0089(18) -0.0063(19) -0.018(2)
C21 0.0417(19) 0.080(3) 0.046(2) 0.014(2) 0.0095(17) -0.002(2)
C22 0.049(2) 0.057(2) 0.051(2) -0.0124(19) 0.0062(18) 0.014(2)
C23 0.051(2) 0.065(3) 0.050(2) 0.0154(19) 0.0096(18) 0.019(2)
O24 0.116(3) 0.122(3) 0.090(3) 0.012(3) 0.007(3) -0.013(3)
O25 0.194(6) 0.137(4) 0.133(4) 0.007(4) -0.032(4) 0.031(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 C17 1.225(4) . ?
O2 C19 1.230(4) . ?
O3 C11 1.245(4) . ?
N4 C19 1.345(5) . ?
N4 C15 1.443(4) . ?
N4 H4 0.80(4) . ?
O5 C7 1.405(4) . ?
O5 H5 0.89(6) . ?
N6 C17 1.345(4) . ?
N6 C16 1.459(4) . ?
N6 H6 0.85(5) . ?
C7 C14 1.518(5) . ?
C7 C15 1.566(5) . ?
C7 H7 1.03(4) . ?
N8 C10 1.339(5) . ?
N8 C18 1.459(4) . ?
N8 H8 0.96(3) . ?
O9 C10 1.236(4) . ?
C10 C16 1.513(5) . ?
C11 N12 1.310(4) . ?
C11 C18 1.532(5) . ?
N12 C21 1.445(5) . ?
N12 H12 0.89(3) . ?
C13 C15 1.549(5) . ?
C13 C14 1.557(6) . ?
C13 H13A 1.00(3) . ?
C13 H13B 1.10(5) . ?
C14 H14A 1.15(4) . ?
C14 H14B 1.00(6) . ?
C15 C17 1.534(5) . ?
C16 C20 1.529(5) . ?
C16 H16 0.97(4) . ?
C18 C23 1.518(6) . ?
C18 H18 0.94(3) . ?
C19 C22 1.507(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C19 N4 C15 121.6(3) . . ?
C19 N4 H4 119(3) . . ?
C15 N4 H4 118(3) . . ?
C7 O5 H5 108(3) . . ?
C17 N6 C16 121.1(3) . . ?
C17 N6 H6 125(3) . . ?
C16 N6 H6 112(3) . . ?
O5 C7 C14 116.8(3) . . ?
O5 C7 C15 119.9(3) . . ?
C14 C7 C15 88.8(3) . . ?
O5 C7 H7 113(2) . . ?
C14 C7 H7 107(2) . . ?
C15 C7 H7 108(2) . . ?
C10 N8 C18 120.7(3) . . ?
C10 N8 H8 120(3) . . ?
C18 N8 H8 119(3) . . ?
O9 C10 N8 122.2(3) . . ?
O9 C10 C16 119.0(3) . . ?
N8 C10 C16 118.9(3) . . ?
O3 C11 N12 122.9(3) . . ?
O3 C11 C18 119.4(3) . . ?
N12 C11 C18 117.7(3) . . ?
C11 N12 C21 124.0(3) . . ?
C11 N12 H12 121(3) . . ?
C21 N12 H12 115(3) . . ?
C15 C13 C14 88.0(3) . . ?
C15 C13 H13A 117(2) . . ?
C14 C13 H13A 125(2) . . ?
C15 C13 H13B 106(2) . . ?
C14 C13 H13B 115(2) . . ?
H13A C13 H13B 104(3) . . ?
C7 C14 C13 88.3(3) . . ?
C7 C14 H14A 109(2) . . ?
C13 C14 H14A 114(2) . . ?
C7 C14 H14B 119(3) . . ?
C13 C14 H14B 121(3) . . ?
H14A C14 H14B 104(4) . . ?
N4 C15 C17 111.3(3) . . ?
N4 C15 C13 118.4(3) . . ?
C17 C15 C13 111.8(3) . . ?
N4 C15 C7 116.5(3) . . ?
C17 C15 C7 109.7(3) . . ?
C13 C15 C7 86.8(3) . . ?
N6 C16 C10 113.8(3) . . ?
N6 C16 C20 108.9(3) . . ?
C10 C16 C20 110.3(3) . . ?
N6 C16 H16 107(2) . . ?
C10 C16 H16 105(2) . . ?
C20 C16 H16 112(2) . . ?
O1 C17 N6 122.6(3) . . ?
O1 C17 C15 122.0(3) . . ?
N6 C17 C15 115.4(3) . . ?
N8 C18 C23 110.5(3) . . ?
N8 C18 C11 111.7(3) . . ?
C23 C18 C11 110.9(3) . . ?
N8 C18 H18 102.8(19) . . ?
C23 C18 H18 110(2) . . ?
C11 C18 H18 111.0(19) . . ?
O2 C19 N4 122.0(3) . . ?
O2 C19 C22 121.1(3) . . ?
N4 C19 C22 116.8(3) . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N12 C21 H21A 109.5 . . ?
N12 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N12 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        28.25
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.050