# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2006


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Arindam Banerjee'
_publ_contact_author_address     
;
Department of Biological Chemistry
Indian Association for the Cultivation of Science
Jadavpur
Kolkata
West Bengal
700032
INDIA
;

_publ_contact_author_email       BCAB@MAHENDRA.IACS.RES.IN

_publ_section_title              
;
Formation of triple helical nanofibers using
self-assembling chiral pseudopeptides and reversal of the
nanostructure's handedness using mirror image building blocks
;

_publ_section_references         
;
Oxford Diffraction Ltd, Crysalis Program (2005)

Oxford Diffraction Ltd, Abspack Program (2005)

Sheldrick, G.M. (1997) SHELXL program for crystallography refinement.
University of Gottingen, Germany.

Spek, A.L., (2004) PLATON program, Utrecht University, The Netherlands
;
loop_
_publ_author_name
'Arindam Banerjee'
'Partha Pratim Bose'
'Apurba Das'
M.Drew

# Attachment 'btc-revised.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 606026'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H13 N O3'
_chemical_formula_weight         183.20

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           hexagonal
_symmetry_space_group_name_H-M   P63

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

_cell_length_a                   15.769(3)
_cell_length_b                   15.769(3)
_cell_length_c                   7.0910(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1527.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_standards_number         ?
_diffrn_measurement_device       'Oxford Diffaction X-Calibur System'
_diffrn_measurement_method       '311 frames, counting time 10 s.'
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10753
_diffrn_reflns_av_R_equivalents  0.1245
_diffrn_reflns_av_sigmaI/netI    0.1204
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         30.30
_reflns_number_total             1906
_reflns_number_gt                1133
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON(Spek,2004)

_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     
;
w=1/[\s^2^(Fo^2^)+(0.1431P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1906
_refine_ls_number_parameters     121
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1528
_refine_ls_R_factor_gt           0.1011
_refine_ls_wR_factor_ref         0.2557
_refine_ls_wR_factor_gt          0.2352
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.9159(3) 0.9085(3) 0.0651(8) 0.0226(10) Uani 1 1 d . . .
C2 C 1.0068(4) 0.9154(3) 0.0653(8) 0.0214(10) Uani 1 1 d . . .
H2 H 1.0115 0.8589 0.0654 0.026 Uiso 1 1 calc R . .
C11 C 0.8226(3) 0.8111(3) 0.0511(8) 0.0201(10) Uani 1 1 d . . .
O11 O 0.7556(2) 0.8008(3) -0.0541(6) 0.0284(9) Uani 1 1 d . . .
N12 N 0.8177(3) 0.7364(3) 0.1534(7) 0.0263(10) Uani 1 1 d . . .
H12 H 0.8665 0.7461 0.2228 0.032 Uiso 1 1 calc R . .
C13 C 0.7310(4) 0.6400(3) 0.1470(9) 0.0279(12) Uani 1 1 d . . .
H13 H 0.6843 0.6437 0.0610 0.034 Uiso 1 1 calc R . .
C131 C 0.7511(4) 0.5600(4) 0.0711(9) 0.0328(12) Uani 1 1 d . . .
H131 H 0.6878 0.4998 0.0571 0.039 Uiso 1 1 calc R . .
C132 C 0.8136(5) 0.5380(4) 0.2033(11) 0.0411(15) Uani 1 1 d . . .
H13A H 0.7833 0.5208 0.3254 0.049 Uiso 1 1 calc R . .
H13B H 0.8775 0.5948 0.2141 0.049 Uiso 1 1 calc R . .
H13C H 0.8194 0.4844 0.1538 0.049 Uiso 1 1 calc R . .
C133 C 0.7990(5) 0.5895(5) -0.1283(10) 0.0481(17) Uani 1 1 d . . .
H13D H 0.8040 0.5361 -0.1812 0.058 Uiso 1 1 calc R . .
H13E H 0.8633 0.6459 -0.1175 0.058 Uiso 1 1 calc R . .
H13F H 0.7594 0.6046 -0.2087 0.058 Uiso 1 1 calc R . .
C14 C 0.6828(3) 0.6118(3) 0.3415(8) 0.0260(11) Uani 1 1 d . . .
O14 O 0.7123(3) 0.6633(3) 0.4820(6) 0.0409(11) Uani 1 1 d . . .
O15 O 0.6035(3) 0.5242(3) 0.3389(7) 0.0383(10) Uani 1 1 d . . .
C16 C 0.5514(5) 0.4895(5) 0.5155(10) 0.0518(19) Uani 1 1 d . . .
H16A H 0.5257 0.5308 0.5526 0.062 Uiso 1 1 calc R . .
H16B H 0.5955 0.4912 0.6108 0.062 Uiso 1 1 calc R . .
H16C H 0.4986 0.4235 0.5002 0.062 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
C1 0.027(2) 0.027(2) 0.012(2) 0.001(2) -0.001(2) 0.012(2)
C2 0.031(2) 0.025(2) 0.015(2) -0.001(2) 0.002(2) 0.019(2)
C11 0.0144(19) 0.021(2) 0.028(3) -0.001(2) 0.000(2) 0.0113(17)
O11 0.0186(16) 0.0278(19) 0.033(2) 0.0069(16) -0.0067(16) 0.0071(15)
N12 0.023(2) 0.023(2) 0.031(3) 0.002(2) -0.0070(19) 0.0099(17)
C13 0.022(2) 0.019(2) 0.037(3) 0.002(2) -0.003(3) 0.0070(19)
C131 0.032(3) 0.028(3) 0.032(3) -0.005(3) -0.006(3) 0.011(2)
C132 0.054(4) 0.033(3) 0.046(4) 0.001(3) 0.005(3) 0.029(3)
C133 0.048(4) 0.049(4) 0.029(3) -0.008(3) 0.002(3) 0.010(3)
C14 0.022(2) 0.019(2) 0.033(3) 0.001(2) -0.001(2) 0.0079(19)
O14 0.041(2) 0.041(2) 0.029(2) -0.0075(19) 0.0070(19) 0.0111(18)
O15 0.033(2) 0.0297(19) 0.035(2) -0.0004(18) 0.005(2) 0.0028(16)
C16 0.043(3) 0.043(3) 0.040(4) 0.004(3) 0.020(3) -0.001(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
C1 C2 1.382(7) . ?
C1 C2 1.397(7) 3_675 ?
C1 C11 1.508(6) . ?
C2 C1 1.397(7) 2_765 ?
C11 O11 1.236(6) . ?
C11 N12 1.353(6) . ?
N12 C13 1.451(6) . ?
C13 C14 1.529(8) . ?
C13 C131 1.542(8) . ?
C131 C132 1.521(9) . ?
C131 C133 1.561(9) . ?
C14 O14 1.221(7) . ?
C14 O15 1.321(6) . ?
O15 C16 1.447(8) . ?

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
C2 C1 C2 120.2(5) . 3_675 ?
C2 C1 C11 121.7(4) . . ?
C2 C1 C11 117.9(4) 3_675 . ?
C1 C2 C1 119.8(5) . 2_765 ?
O11 C11 N12 122.5(4) . . ?
O11 C11 C1 120.6(4) . . ?
N12 C11 C1 116.9(4) . . ?
C11 N12 C13 120.6(4) . . ?
N12 C13 C14 110.3(5) . . ?
N12 C13 C131 113.3(4) . . ?
C14 C13 C131 110.7(4) . . ?
C132 C131 C13 113.2(5) . . ?
C132 C131 C133 110.7(5) . . ?
C13 C131 C133 109.9(5) . . ?
O14 C14 O15 123.6(5) . . ?
O14 C14 C13 125.0(4) . . ?
O15 C14 C13 111.4(5) . . ?
C14 O15 C16 116.4(5) . . ?

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
C2 C1 C2 C1 -0.1(11) 3_675 . . 2_765 ?
C11 C1 C2 C1 175.5(4) . . . 2_765 ?
C2 C1 C11 O11 -136.1(6) . . . . ?
C2 C1 C11 O11 39.6(7) 3_675 . . . ?
C2 C1 C11 N12 41.8(7) . . . . ?
C2 C1 C11 N12 -142.5(5) 3_675 . . . ?
O11 C11 N12 C13 -1.6(8) . . . . ?
C1 C11 N12 C13 -179.5(5) . . . . ?
C11 N12 C13 C14 -116.7(5) . . . . ?
C11 N12 C13 C131 118.6(5) . . . . ?
N12 C13 C131 C132 68.1(7) . . . . ?
C14 C13 C131 C132 -56.5(6) . . . . ?
N12 C13 C131 C133 -56.2(6) . . . . ?
C14 C13 C131 C133 179.3(4) . . . . ?
N12 C13 C14 O14 0.6(7) . . . . ?
C131 C13 C14 O14 126.8(5) . . . . ?
N12 C13 C14 O15 180.0(4) . . . . ?
C131 C13 C14 O15 -53.8(5) . . . . ?
O14 C14 O15 C16 -0.6(8) . . . . ?
C13 C14 O15 C16 180.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        30.30
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.746
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.110

#===END