# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2011


data_global

_journal_coden_Cambridge         177

_publ_requested_journal          'Organic & Biomolecular Chemistry'

loop_
_publ_author_name
'Maity, Sibaprasad'
'Kumar, Pankaj'
'Haldar, Debasish'

_publ_contact_author_name        'Debasish Haldar'
_publ_contact_author_address     
;
BCKV campus main office
Mohonpur, Haringhata
Nadia
Kolkata
West Bengal
India
745212
;

_publ_contact_author_email       deba_h76@yahoo.com
# Attachment 'val-phe.cif'

data_sm
_database_code_depnum_ccdc_archive 'CCDC 801305'
#TrackingRef 'val-phe.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            
methyl-2-(2-(tert-butoxycarbonylamino)-3-methylbutanamido)-3-phenylpropanoate
_chemical_absolute_configuration syn
_chemical_melting_point          356K
_chemical_formula_moiety         'C20 H30 N2 O5'
_chemical_formula_sum            'C20 H30 N2 O5'
_chemical_formula_weight         378.46

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   P2(1)2(1)2(1)
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   5.1057(5)
_cell_length_b                   10.2051(12)
_cell_length_c                   40.956(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2134.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2545
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      21.00

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.084
_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      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14620
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         0.99
_diffrn_reflns_theta_max         22.25
_reflns_number_total             2710
_reflns_number_gt                2070
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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^)+(0.0811P)^2^+0.3763P] 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    constr
_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   -1(2)
_refine_ls_number_reflns         2710
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1315
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_restrained_S_all      0.938
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.001

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 0.3739(4) 0.2581(3) 0.18307(5) 0.0539(7) Uani 1 1 d . . .
N2 N 0.2741(5) 0.2795(3) 0.13109(6) 0.0421(7) Uani 1 1 d . . .
H2 H 0.1150 0.2708 0.1376 0.050 Uiso 1 1 calc R . .
O3 O 0.6997(5) 0.2739(3) 0.14577(6) 0.0597(7) Uani 1 1 d . . .
O4 O 0.1018(4) 0.5065(2) 0.08817(6) 0.0539(7) Uani 1 1 d . . .
O5 O 0.8619(6) 0.7766(3) 0.04990(6) 0.0806(9) Uani 1 1 d . . .
N1 N 0.5418(5) 0.5140(3) 0.08958(6) 0.0383(7) Uani 1 1 d . . .
H1 H 0.6822 0.4686 0.0922 0.046 Uiso 1 1 calc R . .
O6 O 0.7144(5) 0.5864(2) 0.03198(6) 0.0613(8) Uani 1 1 d . . .
C1 C 0.3649(8) 0.2346(6) 0.23973(10) 0.118(2) Uani 1 1 d . . .
H1A H 0.2552 0.3110 0.2403 0.176 Uiso 1 1 calc R . .
H1B H 0.4623 0.2286 0.2597 0.176 Uiso 1 1 calc R . .
H1C H 0.2579 0.1579 0.2372 0.176 Uiso 1 1 calc R . .
C2 C 0.5524(7) 0.2447(4) 0.21127(8) 0.0588(11) Uani 1 1 d . . .
C3 C 0.4696(7) 0.2701(3) 0.15271(8) 0.0416(9) Uani 1 1 d . . .
C4 C 0.3260(6) 0.3041(3) 0.09668(7) 0.0379(9) Uani 1 1 d . . .
H4 H 0.5044 0.2746 0.0918 0.045 Uiso 1 1 calc R . .
C5 C 0.3129(7) 0.4508(3) 0.09087(7) 0.0356(8) Uani 1 1 d . . .
C6 C 0.5700(7) 0.6525(3) 0.08417(7) 0.0402(9) Uani 1 1 d . . .
H6 H 0.3946 0.6881 0.0801 0.048 Uiso 1 1 calc R . .
C7 C 0.6818(7) 0.7236(3) 0.11423(8) 0.0494(9) Uani 1 1 d . . .
H7A H 0.8295 0.6741 0.1226 0.059 Uiso 1 1 calc R . .
H7B H 0.7455 0.8091 0.1076 0.059 Uiso 1 1 calc R . .
C8 C 0.4845(7) 0.7403(4) 0.14086(8) 0.0455(9) Uani 1 1 d . . .
C9 C 0.4068(9) 0.6365(4) 0.16015(9) 0.0645(12) Uani 1 1 d . . .
H9 H 0.4864 0.5551 0.1577 0.077 Uiso 1 1 calc R . .
C10 C 0.2115(12) 0.6529(7) 0.18311(10) 0.0924(17) Uani 1 1 d . . .
H10 H 0.1563 0.5820 0.1956 0.111 Uiso 1 1 calc R . .
C11 C 0.0997(10) 0.7727(8) 0.18746(12) 0.101(2) Uani 1 1 d . . .
H11 H -0.0329 0.7840 0.2028 0.121 Uiso 1 1 calc R . .
C12 C 0.7195(9) 0.3665(5) 0.21456(10) 0.0761(13) Uani 1 1 d . . .
H12A H 0.8402 0.3711 0.1966 0.114 Uiso 1 1 calc R . .
H12B H 0.8151 0.3631 0.2347 0.114 Uiso 1 1 calc R . .
H12C H 0.6091 0.4427 0.2144 0.114 Uiso 1 1 calc R . .
C13 C 0.7134(9) 0.1225(4) 0.20798(11) 0.0811(14) Uani 1 1 d . . .
H13A H 0.6010 0.0500 0.2028 0.122 Uiso 1 1 calc R . .
H13B H 0.8021 0.1053 0.2282 0.122 Uiso 1 1 calc R . .
H13C H 0.8399 0.1339 0.1909 0.122 Uiso 1 1 calc R . .
C14 C 0.3716(9) 0.8582(5) 0.14653(11) 0.0745(13) Uani 1 1 d . . .
H14 H 0.4254 0.9303 0.1344 0.089 Uiso 1 1 calc R . .
C15 C 0.1824(12) 0.8743(7) 0.16944(14) 0.108(2) Uani 1 1 d . . .
H15 H 0.1092 0.9567 0.1727 0.129 Uiso 1 1 calc R . .
C16 C 0.7340(7) 0.6800(4) 0.05403(8) 0.0471(9) Uani 1 1 d . . .
C17 C 0.8721(10) 0.6006(5) 0.00281(9) 0.0829(15) Uani 1 1 d . . .
H17A H 0.8268 0.6808 -0.0080 0.124 Uiso 1 1 calc R . .
H17B H 0.8401 0.5280 -0.0115 0.124 Uiso 1 1 calc R . .
H17C H 1.0541 0.6024 0.0087 0.124 Uiso 1 1 calc R . .
C18 C 0.1381(7) 0.2313(3) 0.07418(8) 0.0484(9) Uani 1 1 d . . .
H18 H -0.0377 0.2673 0.0776 0.058 Uiso 1 1 calc R . .
C19 C 0.2143(10) 0.2567(4) 0.03908(8) 0.0819(14) Uani 1 1 d . . .
H19A H 0.3912 0.2281 0.0355 0.123 Uiso 1 1 calc R . .
H19B H 0.2014 0.3488 0.0346 0.123 Uiso 1 1 calc R . .
H19C H 0.0987 0.2094 0.0248 0.123 Uiso 1 1 calc R . .
C20 C 0.1276(11) 0.0859(4) 0.08131(11) 0.0860(15) Uani 1 1 d . . .
H20A H 0.0092 0.0443 0.0664 0.129 Uiso 1 1 calc R . .
H20B H 0.0677 0.0724 0.1033 0.129 Uiso 1 1 calc R . .
H20C H 0.2993 0.0489 0.0788 0.129 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 0.0305(13) 0.0983(19) 0.0330(13) 0.0124(13) 0.0003(11) 0.0066(14)
N2 0.0257(15) 0.066(2) 0.0345(16) 0.0082(13) 0.0058(13) 0.0005(14)
O3 0.0236(14) 0.105(2) 0.0507(15) 0.0042(14) 0.0023(11) 0.0015(14)
O4 0.0228(14) 0.0571(16) 0.0819(19) 0.0025(13) 0.0004(13) 0.0062(13)
O5 0.111(3) 0.0656(19) 0.0653(18) 0.0003(14) 0.0234(17) -0.034(2)
N1 0.0272(16) 0.0428(17) 0.0450(17) 0.0030(13) -0.0018(14) 0.0037(13)
O6 0.0752(19) 0.0662(18) 0.0424(15) -0.0049(13) 0.0066(14) -0.0109(15)
C1 0.056(3) 0.253(7) 0.044(2) 0.049(4) -0.004(2) 0.012(4)
C2 0.035(2) 0.101(3) 0.040(2) 0.017(2) -0.0076(18) 0.008(2)
C3 0.032(2) 0.056(2) 0.036(2) 0.0030(17) -0.0009(18) 0.0032(19)
C4 0.0274(19) 0.049(2) 0.037(2) -0.0016(16) 0.0074(16) 0.0036(16)
C5 0.029(2) 0.046(2) 0.0319(18) -0.0033(15) 0.0015(16) 0.0017(18)
C6 0.0328(19) 0.041(2) 0.046(2) 0.0004(16) -0.0006(17) 0.0017(16)
C7 0.044(2) 0.049(2) 0.055(2) -0.0062(17) 0.0007(18) -0.0040(19)
C8 0.042(2) 0.055(2) 0.040(2) -0.0053(19) -0.0031(16) 0.007(2)
C9 0.083(3) 0.065(3) 0.046(2) -0.003(2) 0.001(2) -0.008(2)
C10 0.094(4) 0.138(5) 0.045(3) -0.004(3) 0.009(3) -0.042(4)
C11 0.055(3) 0.201(7) 0.048(3) -0.030(4) 0.010(2) -0.001(4)
C12 0.077(3) 0.083(3) 0.069(3) -0.011(2) -0.024(3) 0.010(3)
C13 0.076(3) 0.075(3) 0.092(3) 0.015(3) -0.026(3) 0.004(3)
C14 0.085(3) 0.070(3) 0.069(3) -0.003(2) 0.012(3) 0.023(3)
C15 0.092(4) 0.153(6) 0.078(4) -0.037(4) 0.014(3) 0.053(4)
C16 0.043(2) 0.052(2) 0.046(2) 0.0014(19) 0.0015(19) -0.0013(19)
C17 0.115(4) 0.092(4) 0.041(2) 0.000(2) 0.023(3) -0.002(3)
C18 0.050(2) 0.051(2) 0.043(2) -0.0037(17) -0.0015(17) -0.0004(19)
C19 0.121(4) 0.084(3) 0.042(2) -0.006(2) -0.008(2) -0.012(3)
C20 0.115(4) 0.064(3) 0.079(3) -0.007(2) -0.006(3) -0.028(3)

_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 C3 1.342(4) . ?
O1 C2 1.477(4) . ?
N2 C3 1.338(4) . ?
N2 C4 1.456(4) . ?
N2 H2 0.8600 . ?
O3 C3 1.210(4) . ?
O4 C5 1.223(4) . ?
O5 C16 1.194(4) . ?
N1 C5 1.336(4) . ?
N1 C6 1.438(4) . ?
N1 H1 0.8600 . ?
O6 C16 1.318(4) . ?
O6 C17 1.448(4) . ?
C1 C2 1.512(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C13 1.500(5) . ?
C2 C12 1.514(6) . ?
C4 C5 1.517(4) . ?
C4 C18 1.523(5) . ?
C4 H4 0.9800 . ?
C6 C16 1.518(5) . ?
C6 C7 1.539(4) . ?
C6 H6 0.9800 . ?
C7 C8 1.495(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.354(5) . ?
C8 C9 1.380(5) . ?
C9 C10 1.381(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.361(7) . ?
C10 H10 0.9300 . ?
C11 C15 1.341(8) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.357(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.512(5) . ?
C18 C20 1.513(5) . ?
C18 H18 0.9800 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C3 O1 C2 120.6(2) . . ?
C3 N2 C4 121.2(3) . . ?
C3 N2 H2 119.4 . . ?
C4 N2 H2 119.4 . . ?
C5 N1 C6 124.6(3) . . ?
C5 N1 H1 117.7 . . ?
C6 N1 H1 117.7 . . ?
C16 O6 C17 116.8(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C13 110.2(3) . . ?
O1 C2 C1 102.6(3) . . ?
C13 C2 C1 111.1(4) . . ?
O1 C2 C12 109.9(3) . . ?
C13 C2 C12 112.5(3) . . ?
C1 C2 C12 110.1(4) . . ?
O3 C3 N2 124.5(3) . . ?
O3 C3 O1 125.1(3) . . ?
N2 C3 O1 110.4(3) . . ?
N2 C4 C5 108.3(2) . . ?
N2 C4 C18 112.8(3) . . ?
C5 C4 C18 111.0(3) . . ?
N2 C4 H4 108.2 . . ?
C5 C4 H4 108.2 . . ?
C18 C4 H4 108.2 . . ?
O4 C5 N1 122.8(3) . . ?
O4 C5 C4 120.8(3) . . ?
N1 C5 C4 116.3(3) . . ?
N1 C6 C16 111.2(3) . . ?
N1 C6 C7 112.2(3) . . ?
C16 C6 C7 111.0(3) . . ?
N1 C6 H6 107.4 . . ?
C16 C6 H6 107.4 . . ?
C7 C6 H6 107.4 . . ?
C8 C7 C6 112.8(3) . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C14 C8 C9 117.5(4) . . ?
C14 C8 C7 120.9(3) . . ?
C9 C8 C7 121.6(4) . . ?
C8 C9 C10 120.3(4) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.1(5) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C15 C11 C10 119.4(5) . . ?
C15 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 C15 122.0(5) . . ?
C8 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C11 C15 C14 120.7(5) . . ?
C11 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
O5 C16 O6 122.9(3) . . ?
O5 C16 C6 124.7(3) . . ?
O6 C16 C6 112.4(3) . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C20 111.2(3) . . ?
C19 C18 C4 109.2(3) . . ?
C20 C18 C4 112.6(3) . . ?
C19 C18 H18 107.9 . . ?
C20 C18 H18 107.9 . . ?
C4 C18 H18 107.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        22.25
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.035