# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2005



data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Amit Basak'
_publ_contact_author_address     
;
Chemistry
IIT
IIT Kharagpur 721302 India
Khargpur
INDIA
;

_publ_contact_author_email       ABSK@CHEM.IITKGP.ERNET.IN

_publ_section_title              
;
A Novel Azetidinyl gamma-Lactam Based Peptide With a
Preference for beta-Turn Conformation
;
loop_
_publ_author_name
'Amit Basak'
'Valerio Bertolasi'
'Amit Kumar Das'
'Subhash C. Ghosh'

data_akd41
_database_code_depnum_ccdc_archive 'CCDC 280282'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H22 N2 O5'
_chemical_formula_weight         382.41

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   P21
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.7593(5)
_cell_length_b                   7.8597(6)
_cell_length_c                   18.4268(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.990(4)
_cell_angle_gamma                90.00
_cell_volume                     978.80(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4323
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   ?
_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 Kappa CCD'
_diffrn_measurement_method       Omega/2theta
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4322
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_sigmaI/netI    0.0938
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.71
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2369
_reflns_number_gt                1244
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Kappa CCD server software (Nonius, 1997)'
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek,1990)'
_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^)+(0.0614P)^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   -2(2)
_refine_ls_number_reflns         2369
_refine_ls_number_parameters     273
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1422
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_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
N1 N 0.2414(5) -0.1833(5) 0.62229(17) 0.0557(9) Uani 1 1 d . . .
C2 C 0.2743(6) -0.3584(5) 0.6425(2) 0.0547(11) Uani 1 1 d . . .
H2 H 0.2952 -0.3686 0.6950 0.071(13) Uiso 1 1 calc R . .
C3 C 0.0796(8) -0.4499(9) 0.6183(3) 0.0908(18) Uani 1 1 d . . .
H31 H 0.0976 -0.5100 0.5729 0.12(2) Uiso 1 1 calc R . .
H32 H 0.0386 -0.5307 0.6549 0.11(2) Uiso 1 1 calc R . .
C4 C -0.0685(9) -0.3131(12) 0.6093(4) 0.111(2) Uani 1 1 d . . .
H41 H -0.1565 -0.3104 0.6503 0.19(4) Uiso 1 1 calc R . .
H42 H -0.1467 -0.3299 0.5653 0.15(3) Uiso 1 1 calc R . .
C5 C 0.0498(8) -0.1503(9) 0.6051(3) 0.0863(18) Uani 1 1 d . . .
C6 C 0.3860(7) -0.0489(6) 0.6295(2) 0.0649(12) Uani 1 1 d . . .
H61 H 0.3491 0.0428 0.5967 0.075(13) Uiso 1 1 calc R . .
H62 H 0.5133 -0.0922 0.6144 0.095(17) Uiso 1 1 calc R . .
C7 C 0.4087(6) 0.0233(6) 0.7060(2) 0.0574(11) Uani 1 1 d . . .
H7 H 0.4652 0.1379 0.7034 0.076(14) Uiso 1 1 calc R . .
C8 C 0.5210(7) -0.0795(6) 0.7633(2) 0.0607(11) Uani 1 1 d . . .
N9 N 0.3699(5) -0.0622(4) 0.81168(18) 0.0583(9) Uani 1 1 d . . .
C10 C 0.2317(6) 0.0236(5) 0.7599(2) 0.0526(10) Uani 1 1 d . . .
H10 H 0.1266 -0.0539 0.7435 0.059(12) Uiso 1 1 calc R . .
C12 C 0.3424(7) -0.1191(5) 0.8838(2) 0.0589(11) Uani 1 1 d . . .
C13 C 0.1583(8) -0.0996(7) 0.9149(2) 0.0724(14) Uani 1 1 d . . .
H13 H 0.0548 -0.0476 0.8895 0.079(16) Uiso 1 1 calc R . .
C14 C 0.1327(11) -0.1598(8) 0.9853(3) 0.0947(19) Uani 1 1 d . . .
H14 H 0.0107 -0.1490 1.0074 0.099(19) Uiso 1 1 calc R . .
C15 C 0.2877(13) -0.2351(9) 1.0218(3) 0.104(2) Uani 1 1 d . . .
H15 H 0.2687 -0.2761 1.0686 0.098(17) Uiso 1 1 calc R . .
C16 C 0.4662(12) -0.2511(8) 0.9918(3) 0.0940(17) Uani 1 1 d . . .
H16 H 0.5693 -0.3011 1.0183 0.11(2) Uiso 1 1 calc R . .
C17 C 0.4992(8) -0.1941(6) 0.9216(3) 0.0745(14) Uani 1 1 d . . .
H17 H 0.6225 -0.2058 0.9006 0.085(17) Uiso 1 1 calc R . .
C18 C 0.1480(6) 0.1914(5) 0.7833(2) 0.0519(10) Uani 1 1 d . . .
C19 C 0.2595(8) 0.3058(6) 0.8226(2) 0.0660(12) Uani 1 1 d . . .
H19 H 0.3899 0.2799 0.8351 0.064(13) Uiso 1 1 calc R . .
C20 C 0.1786(10) 0.4604(6) 0.8439(3) 0.0805(15) Uani 1 1 d . . .
H20 H 0.2537 0.5360 0.8717 0.11(2) Uiso 1 1 calc R . .
C21 C -0.0116(9) 0.5012(7) 0.8240(3) 0.0833(15) Uani 1 1 d . . .
H21 H -0.0647 0.6057 0.8372 0.097(18) Uiso 1 1 calc R . .
C22 C -0.1236(8) 0.3877(8) 0.7844(3) 0.0785(14) Uani 1 1 d . . .
H22 H -0.2531 0.4148 0.7710 0.078(15) Uiso 1 1 calc R . .
C23 C -0.0438(7) 0.2328(7) 0.7645(3) 0.0654(12) Uani 1 1 d . . .
H23 H -0.1207 0.1559 0.7380 0.14(3) Uiso 1 1 calc R . .
C11 C 0.4403(6) -0.4396(5) 0.6029(2) 0.0538(10) Uani 1 1 d . . .
O2 O 0.4886(4) -0.3985(4) 0.54212(15) 0.0657(9) Uani 1 1 d . . .
O3 O 0.5238(5) -0.5643(4) 0.63993(18) 0.0725(9) Uani 1 1 d . . .
H13' H 0.6141 -0.6051 0.6164 0.10(2) Uiso 1 1 calc R . .
O4 O 0.6775(5) -0.1517(5) 0.76749(18) 0.0852(11) Uani 1 1 d . . .
O1 O -0.0106(7) -0.0068(7) 0.5926(3) 0.139(2) Uani 1 1 d . . .
O5 O 0.7514(5) -0.7443(4) 0.56212(19) 0.0818(11) 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
N1 0.057(2) 0.057(2) 0.0536(19) -0.0022(17) 0.0019(16) 0.0118(18)
C2 0.060(3) 0.056(3) 0.048(2) -0.0008(19) 0.0057(19) -0.001(2)
C3 0.072(3) 0.104(5) 0.097(4) -0.016(4) 0.017(3) -0.032(4)
C4 0.057(3) 0.171(8) 0.104(4) -0.045(5) -0.001(3) 0.000(4)
C5 0.083(4) 0.115(5) 0.061(3) -0.023(3) -0.009(3) 0.044(4)
C6 0.084(3) 0.054(3) 0.057(2) 0.003(2) 0.016(2) 0.003(2)
C7 0.065(3) 0.041(2) 0.066(3) 0.000(2) 0.012(2) -0.004(2)
C8 0.063(3) 0.049(3) 0.070(3) -0.001(2) 0.008(2) 0.002(2)
N9 0.072(2) 0.048(2) 0.0549(19) 0.0037(17) 0.0051(17) 0.0083(18)
C10 0.063(2) 0.044(2) 0.050(2) -0.0020(19) 0.0021(19) 0.001(2)
C12 0.084(3) 0.038(2) 0.054(2) -0.0016(19) 0.001(2) -0.002(2)
C13 0.092(3) 0.066(3) 0.060(3) 0.003(2) 0.006(3) 0.000(3)
C14 0.129(5) 0.091(5) 0.065(3) 0.008(3) 0.022(4) -0.005(4)
C15 0.151(6) 0.107(5) 0.054(3) 0.013(3) -0.007(4) -0.009(5)
C16 0.120(5) 0.088(4) 0.074(4) 0.011(3) -0.019(4) 0.006(4)
C17 0.094(4) 0.063(3) 0.066(3) -0.001(2) -0.011(3) 0.004(3)
C18 0.061(3) 0.041(2) 0.054(2) -0.0032(19) 0.0030(19) -0.001(2)
C19 0.072(3) 0.052(3) 0.073(3) -0.006(2) -0.010(2) 0.008(2)
C20 0.114(4) 0.046(3) 0.081(3) -0.017(2) -0.004(3) 0.000(3)
C21 0.108(4) 0.060(3) 0.082(3) -0.007(3) 0.010(3) 0.021(3)
C22 0.073(3) 0.079(4) 0.084(3) 0.000(3) 0.008(3) 0.027(3)
C23 0.062(3) 0.067(3) 0.067(3) -0.004(2) 0.000(2) 0.003(3)
C11 0.060(2) 0.043(2) 0.058(2) -0.003(2) -0.008(2) 0.004(2)
O2 0.0686(19) 0.072(2) 0.0564(17) 0.0050(15) 0.0082(14) 0.0165(16)
O3 0.090(2) 0.056(2) 0.0719(19) 0.0067(17) 0.0023(18) 0.0140(18)
O4 0.080(2) 0.087(3) 0.089(2) 0.004(2) 0.0114(18) 0.024(2)
O1 0.152(4) 0.147(5) 0.116(3) -0.015(3) -0.023(3) 0.106(4)
O5 0.088(2) 0.064(2) 0.093(2) -0.0203(18) -0.0163(18) 0.0185(19)

_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
N1 C5 1.353(6) . ?
N1 C2 1.442(6) . ?
N1 C6 1.444(6) . ?
C2 C11 1.492(6) . ?
C2 C3 1.558(7) . ?
C2 H2 0.9800 . ?
C3 C4 1.476(10) . ?
C3 H31 0.9700 . ?
C3 H32 0.9700 . ?
C4 C5 1.512(10) . ?
C4 H41 0.9700 . ?
C4 H42 0.9700 . ?
C5 O1 1.220(8) . ?
C6 C7 1.524(6) . ?
C6 H61 0.9700 . ?
C6 H62 0.9700 . ?
C7 C8 1.522(6) . ?
C7 C10 1.569(5) . ?
C7 H7 0.9800 . ?
C8 O4 1.202(5) . ?
C8 N9 1.374(5) . ?
N9 C12 1.418(5) . ?
N9 C10 1.485(5) . ?
C10 C18 1.501(6) . ?
C10 H10 0.9800 . ?
C12 C13 1.387(6) . ?
C12 C17 1.390(6) . ?
C13 C14 1.395(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.343(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(8) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.372(6) . ?
C18 C23 1.376(6) . ?
C19 C20 1.392(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.369(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.384(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C11 O2 1.215(5) . ?
C11 O3 1.316(5) . ?
O3 H13 0.8200 . ?

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
C5 N1 C2 112.7(5) . . ?
C5 N1 C6 121.7(5) . . ?
C2 N1 C6 125.0(4) . . ?
N1 C2 C11 113.3(4) . . ?
N1 C2 C3 104.0(4) . . ?
C11 C2 C3 107.5(4) . . ?
N1 C2 H2 110.6 . . ?
C11 C2 H2 110.6 . . ?
C3 C2 H2 110.6 . . ?
C4 C3 C2 105.3(5) . . ?
C4 C3 H31 110.7 . . ?
C2 C3 H31 110.7 . . ?
C4 C3 H32 110.7 . . ?
C2 C3 H32 110.7 . . ?
H31 C3 H32 108.8 . . ?
C3 C4 C5 105.3(5) . . ?
C3 C4 H41 110.7 . . ?
C5 C4 H41 110.7 . . ?
C3 C4 H42 110.7 . . ?
C5 C4 H42 110.7 . . ?
H41 C4 H42 108.8 . . ?
O1 C5 N1 122.5(7) . . ?
O1 C5 C4 128.1(6) . . ?
N1 C5 C4 109.3(5) . . ?
N1 C6 C7 114.5(3) . . ?
N1 C6 H61 108.6 . . ?
C7 C6 H61 108.6 . . ?
N1 C6 H62 108.6 . . ?
C7 C6 H62 108.6 . . ?
H61 C6 H62 107.6 . . ?
C8 C7 C6 119.0(4) . . ?
C8 C7 C10 86.4(3) . . ?
C6 C7 C10 121.4(4) . . ?
C8 C7 H7 109.3 . . ?
C6 C7 H7 109.3 . . ?
C10 C7 H7 109.3 . . ?
O4 C8 N9 132.0(4) . . ?
O4 C8 C7 136.3(4) . . ?
N9 C8 C7 91.7(3) . . ?
C8 N9 C12 133.5(4) . . ?
C8 N9 C10 95.4(3) . . ?
C12 N9 C10 130.9(3) . . ?
N9 C10 C18 116.8(3) . . ?
N9 C10 C7 85.9(3) . . ?
C18 C10 C7 118.6(3) . . ?
N9 C10 H10 111.1 . . ?
C18 C10 H10 111.1 . . ?
C7 C10 H10 111.1 . . ?
C13 C12 C17 121.4(4) . . ?
C13 C12 N9 119.0(4) . . ?
C17 C12 N9 119.5(4) . . ?
C12 C13 C14 118.2(5) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
C15 C14 C13 119.9(6) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 121.5(6) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 120.9(6) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C12 C17 C16 118.1(5) . . ?
C12 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
C19 C18 C23 119.0(4) . . ?
C19 C18 C10 121.4(4) . . ?
C23 C18 C10 119.6(4) . . ?
C18 C19 C20 120.4(5) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 120.0(5) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 119.8(5) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C23 120.0(5) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C18 C23 C22 120.7(5) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
O2 C11 O3 123.8(4) . . ?
O2 C11 C2 123.5(4) . . ?
O3 C11 C2 112.6(4) . . ?
C11 O3 H13 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.035