# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       anita@iiserbhopal.ac.in
_publ_contact_author_name        'Anita Dutt Konar'
_publ_author_name                'Anita Dutt Konar'

# Attachment '- Peptide I.cif'

data_as1f
_database_code_depnum_ccdc_archive 'CCDC 861407'
#TrackingRef '- Peptide I.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H28 N4 O6'
_chemical_formula_sum            'C21 H28 N4 O6'
_chemical_formula_weight         432.47
_chemical_absolute_configuration unk

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           ?
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   6.0152(11)
_cell_length_b                   12.442(2)
_cell_length_c                   29.838(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2233.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   "Empirical''Bruker SADABS V2.10"
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'Bruker SADABS V2.10'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(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            4001
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_sigmaI/netI    0.1484
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         28.70
_reflns_number_total             3136
_reflns_number_gt                1628
_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^)+(0.0487P)^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   -1(2)
_refine_ls_number_reflns         3136
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   0.799
_refine_ls_restrained_S_all      0.799
_refine_ls_shift/su_max          0.002
_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
H1A H 0.007(11) 0.786(3) 0.1444(14) 0.017(12) Uiso 1 1 d . . .
H2A H 0.321(11) 0.635(3) 0.1369(12) 0.012(11) Uiso 1 1 d . . .
O6 O 0.0823(10) 1.1575(2) 0.18337(11) 0.0410(17) Uani 1 1 d . . .
O1 O 0.3641(8) 0.97301(18) 0.03348(8) 0.0268(12) Uani 1 1 d . . .
O2 O 0.2671(8) 0.8860(2) 0.09847(9) 0.0331(13) Uani 1 1 d . . .
N2 N 0.1435(10) 0.6355(2) 0.12233(11) 0.0207(14) Uani 1 1 d . . .
O3 O -0.0493(8) 0.6895(2) 0.06056(11) 0.0244(12) Uani 1 1 d . . .
C8 C 0.1286(14) 0.6760(3) 0.08045(14) 0.022(2) Uani 1 1 d . . .
N1 N 0.3616(9) 0.7957(2) 0.03546(11) 0.0239(14) Uani 1 1 d . . .
H1 H 0.3854 0.7991 0.0071 0.029 Uiso 1 1 calc R . .
C10 C 0.0482(11) 0.5564(3) 0.19232(14) 0.030(2) Uani 1 1 d . . .
H10A H 0.1621 0.5035 0.1878 0.045 Uiso 1 1 calc R . .
H10B H -0.0685 0.5264 0.2103 0.045 Uiso 1 1 calc R . .
H10C H 0.1102 0.6178 0.2073 0.045 Uiso 1 1 calc R . .
O4 O -0.4154(9) 0.6497(3) 0.16459(11) 0.0346(16) Uani 1 1 d . . .
C5 C 0.3532(11) 0.6936(3) 0.05844(14) 0.0232(17) Uani 1 1 d . . .
H5 H 0.4695 0.6916 0.0814 0.028 Uiso 1 1 calc R . .
C17 C -0.2368(13) 1.0556(3) 0.20013(15) 0.029(2) Uani 1 1 d . . .
N3 N -0.1463(10) 0.7790(3) 0.16150(13) 0.0278(16) Uani 1 1 d . . .
C4 C 0.3310(11) 0.8856(3) 0.05999(15) 0.0252(18) Uani 1 1 d . . .
C14 C -0.4564(13) 0.8596(4) 0.20258(15) 0.031(2) Uani 1 1 d . . .
H14 H -0.5303 0.7940 0.2034 0.038 Uiso 1 1 calc R . .
C6 C 0.3943(12) 0.6028(3) 0.02446(13) 0.0272(19) Uani 1 1 d . . .
H6A H 0.2844 0.6070 0.0007 0.033 Uiso 1 1 calc R . .
H6B H 0.5400 0.6118 0.0111 0.033 Uiso 1 1 calc R . .
O5 O -0.2129(11) 1.2441(2) 0.21226(12) 0.065(2) Uani 1 1 d . . .
C7 C 0.3811(12) 0.4969(3) 0.04615(14) 0.0260(18) Uani 1 1 d . . .
C13 C -0.2545(12) 0.8675(3) 0.18094(14) 0.0220(17) Uani 1 1 d . . .
C19 C -0.1264(15) 1.1618(3) 0.19925(16) 0.031(2) Uani 1 1 d . . .
C12 C -0.2223(14) 0.6754(4) 0.15728(15) 0.026(2) Uani 1 1 d . . .
C11 C -0.1460(13) 0.4956(3) 0.12195(15) 0.033(2) Uani 1 1 d . . .
H11A H -0.2155 0.5202 0.0949 0.049 Uiso 1 1 calc R . .
H11B H -0.2548 0.4612 0.1406 0.049 Uiso 1 1 calc R . .
H11C H -0.0304 0.4453 0.1147 0.049 Uiso 1 1 calc R . .
C18 C -0.1430(11) 0.9660(3) 0.17914(13) 0.0244(17) Uani 1 1 d . . .
H18 H -0.0079 0.9718 0.1642 0.029 Uiso 1 1 calc R . .
C9 C -0.0466(11) 0.5910(3) 0.14681(14) 0.0184(18) Uani 1 1 d . . .
C16 C -0.4433(13) 1.0476(4) 0.22162(16) 0.032(2) Uani 1 1 d . . .
H16 H -0.5076 1.1080 0.2347 0.039 Uiso 1 1 calc R . .
N7 N 0.3710(10) 0.4156(3) 0.06392(13) 0.0388(18) Uani 1 1 d . . .
C3 C 0.4148(13) 1.1516(3) 0.01246(14) 0.037(2) Uani 1 1 d . . .
H3A H 0.5616 1.1300 0.0036 0.056 Uiso 1 1 calc R . .
H3B H 0.4166 1.2259 0.0210 0.056 Uiso 1 1 calc R . .
H3C H 0.3141 1.1417 -0.0122 0.056 Uiso 1 1 calc R . .
C15 C -0.5509(13) 0.9496(4) 0.22332(16) 0.042(2) Uani 1 1 d . . .
H15 H -0.6861 0.9434 0.2382 0.050 Uiso 1 1 calc R . .
C28 C 0.3394(13) 1.0838(3) 0.05187(14) 0.027(2) Uani 1 1 d . . .
C2 C 0.4986(12) 1.0977(3) 0.09147(17) 0.035(2) Uani 1 1 d . . .
H2B H 0.4404 1.0606 0.1171 0.053 Uiso 1 1 calc R . .
H2C H 0.5140 1.1727 0.0983 0.053 Uiso 1 1 calc R . .
H2D H 0.6413 1.0684 0.0838 0.053 Uiso 1 1 calc R . .
C20 C 0.2025(14) 1.2573(3) 0.18236(17) 0.056(3) Uani 1 1 d . . .
H20A H 0.1304 1.3062 0.1621 0.084 Uiso 1 1 calc R . .
H20B H 0.3519 1.2445 0.1724 0.084 Uiso 1 1 calc R . .
H20C H 0.2053 1.2880 0.2119 0.084 Uiso 1 1 calc R . .
C1 C 0.1029(13) 1.1056(3) 0.06451(15) 0.0292(19) Uani 1 1 d . . .
H1B H 0.0082 1.0913 0.0393 0.044 Uiso 1 1 calc R . .
H1C H 0.0875 1.1794 0.0733 0.044 Uiso 1 1 calc R . .
H1D H 0.0612 1.0599 0.0891 0.044 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
O6 0.055(6) 0.0260(17) 0.042(2) -0.0058(13) 0.004(2) 0.006(2)
O1 0.039(4) 0.0185(13) 0.0225(17) 0.0023(11) 0.0044(19) -0.0012(16)
O2 0.053(4) 0.0299(15) 0.0164(17) -0.0016(12) 0.0057(18) 0.0004(18)
N2 0.023(5) 0.0235(17) 0.015(2) -0.0014(13) -0.001(2) -0.003(2)
O3 0.020(5) 0.0308(16) 0.0222(19) 0.0001(13) -0.004(2) 0.0006(17)
C8 0.033(7) 0.0163(19) 0.016(3) -0.0052(15) 0.003(3) 0.005(2)
N1 0.034(5) 0.0201(16) 0.0174(19) 0.0027(13) 0.008(2) 0.0004(19)
C10 0.027(7) 0.039(2) 0.024(3) 0.0103(19) 0.000(3) -0.001(3)
O4 0.024(6) 0.0425(19) 0.037(2) -0.0011(15) 0.001(2) -0.004(2)
C5 0.033(6) 0.0186(19) 0.018(2) -0.0009(15) 0.001(3) -0.001(2)
C17 0.033(7) 0.034(2) 0.019(3) -0.0043(17) -0.006(3) 0.014(3)
N3 0.027(6) 0.0297(19) 0.027(2) -0.0029(15) 0.010(3) -0.001(2)
C4 0.022(6) 0.026(2) 0.028(3) 0.0003(18) 0.000(3) -0.004(2)
C14 0.022(7) 0.046(3) 0.026(3) -0.005(2) 0.002(3) 0.007(3)
C6 0.033(6) 0.024(2) 0.025(3) 0.0007(16) 0.008(3) 0.003(2)
O5 0.085(7) 0.0352(18) 0.076(3) -0.0165(17) 0.007(3) 0.021(2)
C7 0.022(6) 0.027(2) 0.029(3) -0.0093(17) 0.000(3) 0.002(2)
C13 0.011(6) 0.036(2) 0.018(3) -0.0011(17) 0.000(3) 0.009(3)
C19 0.031(8) 0.037(3) 0.026(3) -0.0020(19) -0.004(3) 0.005(3)
C12 0.025(8) 0.033(3) 0.018(3) 0.0000(18) -0.005(3) 0.003(3)
C11 0.036(7) 0.026(2) 0.036(3) -0.0008(18) -0.006(3) -0.009(3)
C18 0.017(6) 0.041(2) 0.016(2) 0.0007(18) -0.005(3) 0.013(3)
C9 0.006(6) 0.033(2) 0.017(2) 0.0009(17) 0.005(2) 0.000(2)
C16 0.018(7) 0.048(3) 0.031(3) -0.007(2) -0.006(3) 0.021(3)
N7 0.045(6) 0.0252(19) 0.046(3) -0.0029(17) -0.005(3) -0.001(2)
C3 0.050(7) 0.020(2) 0.041(3) 0.0003(19) 0.012(3) 0.001(3)
C15 0.033(8) 0.060(3) 0.033(3) -0.009(2) 0.007(3) 0.018(4)
C28 0.029(7) 0.021(2) 0.030(3) -0.0045(17) 0.007(3) -0.009(3)
C2 0.029(7) 0.031(2) 0.045(3) -0.003(2) -0.011(3) -0.003(3)
C20 0.086(10) 0.025(2) 0.058(4) -0.001(2) -0.008(4) -0.003(3)
C1 0.028(7) 0.033(2) 0.027(3) -0.0002(19) -0.005(3) -0.004(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
O6 C19 1.343(9) . ?
O6 C20 1.437(7) . ?
O1 C4 1.359(4) . ?
O1 C28 1.491(4) . ?
O2 C4 1.211(5) . ?
N2 C8 1.350(5) . ?
N2 C9 1.466(7) . ?
O3 C8 1.235(8) . ?
C8 C5 1.518(9) . ?
N1 C4 1.349(5) . ?
N1 C5 1.445(4) . ?
C10 C9 1.534(6) . ?
O4 C12 1.224(8) . ?
C5 C6 1.538(5) . ?
C17 C18 1.398(6) . ?
C17 C16 1.402(10) . ?
C17 C19 1.479(7) . ?
N3 C12 1.374(6) . ?
N3 C13 1.404(6) . ?
C14 C13 1.379(9) . ?
C14 C15 1.400(7) . ?
C6 C7 1.470(5) . ?
O5 C19 1.212(6) . ?
C7 N7 1.144(5) . ?
C13 C18 1.398(7) . ?
C12 C9 1.523(8) . ?
C11 C9 1.521(6) . ?
C16 C15 1.382(8) . ?
C3 C28 1.517(6) . ?
C28 C1 1.497(9) . ?
C28 C2 1.531(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
C19 O6 C20 116.3(4) . . ?
C4 O1 C28 120.7(3) . . ?
C8 N2 C9 123.4(6) . . ?
O3 C8 N2 123.6(7) . . ?
O3 C8 C5 122.9(4) . . ?
N2 C8 C5 113.3(6) . . ?
C4 N1 C5 117.8(3) . . ?
N1 C5 C8 111.3(4) . . ?
N1 C5 C6 109.1(3) . . ?
C8 C5 C6 108.8(4) . . ?
C18 C17 C16 120.4(5) . . ?
C18 C17 C19 121.6(6) . . ?
C16 C17 C19 118.0(5) . . ?
C12 N3 C13 128.3(6) . . ?
O2 C4 N1 124.1(4) . . ?
O2 C4 O1 126.5(4) . . ?
N1 C4 O1 109.1(4) . . ?
C13 C14 C15 120.6(6) . . ?
C7 C6 C5 111.1(3) . . ?
N7 C7 C6 178.5(4) . . ?
C14 C13 C18 120.2(5) . . ?
C14 C13 N3 123.1(5) . . ?
C18 C13 N3 116.7(6) . . ?
O5 C19 O6 123.2(6) . . ?
O5 C19 C17 123.8(7) . . ?
O6 C19 C17 113.0(5) . . ?
O4 C12 N3 123.0(6) . . ?
O4 C12 C9 121.0(5) . . ?
N3 C12 C9 115.8(7) . . ?
C13 C18 C17 119.2(6) . . ?
N2 C9 C11 111.0(4) . . ?
N2 C9 C12 112.5(4) . . ?
C11 C9 C12 111.4(5) . . ?
N2 C9 C10 104.9(5) . . ?
C11 C9 C10 111.1(3) . . ?
C12 C9 C10 105.6(4) . . ?
C15 C16 C17 119.6(5) . . ?
C16 C15 C14 120.0(7) . . ?
O1 C28 C1 110.8(4) . . ?
O1 C28 C3 101.5(3) . . ?
C1 C28 C3 112.3(5) . . ?
O1 C28 C2 109.0(4) . . ?
C1 C28 C2 112.3(4) . . ?
C3 C28 C2 110.4(5) . . ?

_diffrn_measured_fraction_theta_max 0.614
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_full 0.614
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.054

# Attachment '- Peptide II.cif'

data_final
_database_code_depnum_ccdc_archive 'CCDC 861408'
#TrackingRef '- Peptide II.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H29 N3 O7'
_chemical_formula_sum            'C20 H29 N3 O7'
_chemical_formula_weight         423.46
_chemical_absolute_configuration unk

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           ?
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   6.037(2)
_cell_length_b                   11.169(4)
_cell_length_c                   16.091(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.612(4)
_cell_angle_gamma                90.00
_cell_volume                     1079.7(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'Bruker SADABS V2.10'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(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            4068
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.28
_diffrn_reflns_theta_max         28.13
_reflns_number_total             3724
_reflns_number_gt                3480
_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^)+(0.1016P)^2^+0.0318P] 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   1.0(11)
_refine_ls_number_reflns         3724
_refine_ls_number_parameters     294
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1451
_refine_ls_wR_factor_gt          0.1272
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.070
_refine_ls_shift/su_mean         0.007

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
H1A H 1.244(5) 0.753(3) 0.3760(19) 0.015(7) Uiso 1 1 d . . .
H3' H 0.752(5) 0.514(3) 0.1994(18) 0.014(7) Uiso 1 1 d . . .
O5 O 0.3689(3) 0.57925(19) 0.07970(10) 0.0232(4) Uani 1 1 d . . .
O6 O -0.1251(3) 0.2792(2) 0.10572(11) 0.0257(4) Uani 1 1 d . . .
O3 O 1.4475(3) 0.8862(2) 0.30041(11) 0.0263(5) Uani 1 1 d . . .
H3 H 1.5566 0.8493 0.2877 0.039 Uiso 1 1 calc R . .
O4 O 0.7788(3) 0.7643(2) 0.23025(11) 0.0267(5) Uani 1 1 d . . .
O2 O 0.9886(3) 0.5342(2) 0.32576(11) 0.0252(4) Uani 1 1 d . . .
O7 O -0.0996(3) 0.1272(2) 0.19713(11) 0.0268(5) Uani 1 1 d . . .
O1 O 1.1317(3) 0.60026(19) 0.45493(10) 0.0230(4) Uani 1 1 d . . .
N3 N 0.6201(3) 0.5000(2) 0.17957(12) 0.0193(5) Uani 1 1 d . . .
C17 C 0.4750(4) 0.2618(3) 0.32268(15) 0.0268(6) Uani 1 1 d . . .
H17 H 0.5360 0.2276 0.3724 0.032 Uiso 1 1 calc R . .
C13 C 0.5591(4) 0.5720(2) 0.11356(13) 0.0176(5) Uani 1 1 d . . .
N2 N 0.9455(3) 0.6541(2) 0.13567(12) 0.0180(5) Uani 1 1 d . . .
H2' H 1.0669 0.6197 0.1251 0.022 Uiso 1 1 calc R . .
C20 C 0.2893(4) 0.3690(3) 0.17559(13) 0.0187(5) Uani 1 1 d . . .
H20 H 0.2250 0.4052 0.1270 0.022 Uiso 1 1 calc R . .
C18 C 0.2746(4) 0.2192(3) 0.28393(15) 0.0232(6) Uani 1 1 d . . .
N1 N 1.1636(4) 0.7131(2) 0.34340(12) 0.0221(5) Uani 1 1 d . . .
C19 C 0.1835(4) 0.2734(3) 0.21090(14) 0.0186(5) Uani 1 1 d . . .
C6 C 1.1775(4) 0.7313(3) 0.25493(13) 0.0201(5) Uani 1 1 d . . .
H6 H 1.2814 0.6734 0.2344 0.024 Uiso 1 1 calc R . .
C15 C 0.4924(4) 0.4099(3) 0.21365(14) 0.0193(5) Uani 1 1 d . . .
C7 C 1.2620(4) 0.8592(3) 0.24282(16) 0.0245(6) Uani 1 1 d . . .
H7A H 1.3037 0.8678 0.1864 0.029 Uiso 1 1 calc R . .
H7B H 1.1432 0.9156 0.2500 0.029 Uiso 1 1 calc R . .
C1 C 1.1305(5) 0.5293(3) 0.59104(15) 0.0296(6) Uani 1 1 d . . .
H1B H 1.2898 0.5237 0.5941 0.044 Uiso 1 1 calc R . .
H1C H 1.0751 0.4719 0.6283 0.044 Uiso 1 1 calc R . .
H1D H 1.0889 0.6084 0.6068 0.044 Uiso 1 1 calc R . .
C21 C -0.0278(4) 0.2295(3) 0.16532(14) 0.0198(5) Uani 1 1 d . . .
C10 C 0.7495(4) 0.6395(3) 0.07529(14) 0.0195(5) Uani 1 1 d . . .
C16 C 0.5838(4) 0.3553(3) 0.28732(15) 0.0227(6) Uani 1 1 d . . .
C4 C 1.0857(4) 0.6079(3) 0.37092(14) 0.0212(6) Uani 1 1 d . . .
C23 C -0.3039(4) 0.0806(3) 0.15617(17) 0.0291(6) Uani 1 1 d . . .
H23A H -0.4241 0.1339 0.1653 0.044 Uiso 1 1 calc R . .
H23B H -0.3328 0.0032 0.1786 0.044 Uiso 1 1 calc R . .
H23C H -0.2913 0.0738 0.0974 0.044 Uiso 1 1 calc R . .
C2 C 1.1066(5) 0.3813(3) 0.47448(18) 0.0329(7) Uani 1 1 d . . .
H2B H 1.0507 0.3684 0.4173 0.049 Uiso 1 1 calc R . .
H2C H 1.0499 0.3204 0.5088 0.049 Uiso 1 1 calc R . .
H2D H 1.2663 0.3778 0.4796 0.049 Uiso 1 1 calc R . .
C12 C 0.6654(4) 0.7594(3) 0.03941(15) 0.0244(6) Uani 1 1 d . . .
H12A H 0.6224 0.8093 0.0837 0.037 Uiso 1 1 calc R . .
H12B H 0.5393 0.7463 -0.0007 0.037 Uiso 1 1 calc R . .
H12C H 0.7816 0.7980 0.0127 0.037 Uiso 1 1 calc R . .
C11 C 0.8190(4) 0.5574(3) 0.00563(14) 0.0234(6) Uani 1 1 d . . .
H11A H 0.9386 0.5940 -0.0203 0.035 Uiso 1 1 calc R . .
H11B H 0.6944 0.5453 -0.0353 0.035 Uiso 1 1 calc R . .
H11C H 0.8674 0.4817 0.0291 0.035 Uiso 1 1 calc R . .
C3 C 0.7811(5) 0.5188(3) 0.49473(17) 0.0307(7) Uani 1 1 d . . .
H3A H 0.7450 0.6009 0.5046 0.046 Uiso 1 1 calc R . .
H3B H 0.7188 0.4688 0.5351 0.046 Uiso 1 1 calc R . .
H3C H 0.7207 0.4961 0.4396 0.046 Uiso 1 1 calc R . .
C29 C 1.0324(4) 0.5037(3) 0.50254(16) 0.0246(6) Uani 1 1 d . . .
C8 C 0.9478(4) 0.7177(3) 0.20631(13) 0.0178(5) Uani 1 1 d . . .
H1 H 0.710(5) 0.380(3) 0.3137(17) 0.015(7) Uiso 1 1 d . . .
H2 H 0.217(4) 0.158(3) 0.3068(18) 0.010(6) 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
O5 0.0209(8) 0.0274(12) 0.0221(8) 0.0058(8) 0.0065(6) 0.0009(8)
O6 0.0296(9) 0.0216(12) 0.0255(8) 0.0036(8) 0.0003(7) -0.0020(8)
O3 0.0241(9) 0.0294(13) 0.0265(9) -0.0066(8) 0.0085(7) -0.0056(8)
O4 0.0261(9) 0.0317(13) 0.0239(8) -0.0019(8) 0.0107(6) 0.0027(8)
O2 0.0339(10) 0.0231(13) 0.0185(8) -0.0003(8) 0.0016(7) -0.0079(8)
O7 0.0295(9) 0.0240(13) 0.0273(9) 0.0039(8) 0.0045(7) -0.0086(8)
O1 0.0319(9) 0.0227(13) 0.0148(7) 0.0015(7) 0.0039(6) -0.0049(8)
N3 0.0193(10) 0.0199(14) 0.0187(9) 0.0020(8) 0.0029(7) -0.0026(9)
C17 0.0332(13) 0.0291(19) 0.0185(10) 0.0047(11) 0.0052(9) -0.0025(12)
C13 0.0213(10) 0.0167(15) 0.0162(9) -0.0011(9) 0.0087(7) 0.0000(9)
N2 0.0162(9) 0.0224(14) 0.0162(9) 0.0007(8) 0.0054(6) -0.0017(8)
C20 0.0232(11) 0.0192(16) 0.0146(9) -0.0006(9) 0.0055(8) 0.0001(10)
C18 0.0288(12) 0.0222(17) 0.0200(10) 0.0043(11) 0.0090(9) -0.0043(11)
N1 0.0279(11) 0.0246(15) 0.0142(9) -0.0032(9) 0.0038(7) -0.0089(10)
C19 0.0200(10) 0.0189(15) 0.0181(9) -0.0016(9) 0.0082(8) 0.0000(9)
C6 0.0255(11) 0.0220(16) 0.0138(9) -0.0017(10) 0.0066(8) -0.0021(10)
C15 0.0231(11) 0.0178(16) 0.0185(10) -0.0011(10) 0.0093(8) -0.0020(10)
C7 0.0291(13) 0.0222(17) 0.0234(11) 0.0020(11) 0.0094(9) -0.0031(11)
C1 0.0341(14) 0.038(2) 0.0173(11) 0.0003(11) 0.0041(9) -0.0029(12)
C21 0.0198(10) 0.0216(16) 0.0189(10) -0.0038(10) 0.0064(7) -0.0016(10)
C10 0.0187(10) 0.0250(17) 0.0158(10) 0.0014(9) 0.0060(8) 0.0004(10)
C16 0.0202(11) 0.0293(18) 0.0188(10) -0.0006(10) 0.0024(8) -0.0057(10)
C4 0.0232(11) 0.0260(18) 0.0150(10) 0.0000(10) 0.0053(8) -0.0004(10)
C23 0.0254(12) 0.0306(19) 0.0317(13) 0.0021(12) 0.0047(9) -0.0088(12)
C2 0.0420(16) 0.028(2) 0.0304(13) 0.0036(13) 0.0098(11) 0.0009(13)
C12 0.0301(12) 0.0215(17) 0.0219(11) 0.0054(10) 0.0035(9) -0.0008(11)
C11 0.0229(11) 0.0327(19) 0.0154(10) -0.0005(10) 0.0055(8) 0.0005(11)
C3 0.0327(14) 0.034(2) 0.0265(12) 0.0002(12) 0.0082(10) -0.0039(12)
C29 0.0338(14) 0.0230(18) 0.0183(10) 0.0024(10) 0.0089(9) -0.0029(11)
C8 0.0216(11) 0.0164(15) 0.0164(10) 0.0038(9) 0.0063(8) -0.0014(10)

_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
O5 C13 1.224(3) . ?
O6 C21 1.210(3) . ?
O3 C7 1.414(3) . ?
O4 C8 1.240(3) . ?
O2 C4 1.211(3) . ?
O7 C21 1.341(3) . ?
O7 C23 1.438(3) . ?
O1 C4 1.356(3) . ?
O1 C29 1.483(3) . ?
N3 C13 1.354(3) . ?
N3 C15 1.411(3) . ?
C17 C16 1.385(4) . ?
C17 C18 1.390(4) . ?
C13 C10 1.551(3) . ?
N2 C8 1.339(3) . ?
N2 C10 1.465(3) . ?
C20 C15 1.393(3) . ?
C20 C19 1.394(4) . ?
C18 C19 1.387(4) . ?
N1 C4 1.356(4) . ?
N1 C6 1.449(3) . ?
C19 C21 1.491(3) . ?
C6 C8 1.532(3) . ?
C6 C7 1.535(4) . ?
C15 C16 1.398(4) . ?
C1 C29 1.515(4) . ?
C10 C12 1.525(4) . ?
C10 C11 1.538(4) . ?
C2 C29 1.521(5) . ?
C3 C29 1.519(4) . ?

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
C21 O7 C23 115.4(2) . . ?
C4 O1 C29 120.5(2) . . ?
C13 N3 C15 127.7(2) . . ?
C16 C17 C18 120.1(2) . . ?
O5 C13 N3 124.0(2) . . ?
O5 C13 C10 119.3(2) . . ?
N3 C13 C10 116.4(2) . . ?
C8 N2 C10 124.3(2) . . ?
C15 C20 C19 119.4(2) . . ?
C19 C18 C17 119.1(3) . . ?
C4 N1 C6 119.8(2) . . ?
C18 C19 C20 121.4(2) . . ?
C18 C19 C21 121.5(2) . . ?
C20 C19 C21 117.1(2) . . ?
N1 C6 C8 110.57(18) . . ?
N1 C6 C7 107.9(2) . . ?
C8 C6 C7 108.8(2) . . ?
C20 C15 C16 119.2(2) . . ?
C20 C15 N3 123.6(2) . . ?
C16 C15 N3 117.1(2) . . ?
O3 C7 C6 111.5(2) . . ?
O6 C21 O7 123.0(2) . . ?
O6 C21 C19 124.4(2) . . ?
O7 C21 C19 112.7(2) . . ?
N2 C10 C12 111.7(2) . . ?
N2 C10 C11 106.84(19) . . ?
C12 C10 C11 110.6(2) . . ?
N2 C10 C13 111.88(18) . . ?
C12 C10 C13 110.17(19) . . ?
C11 C10 C13 105.4(2) . . ?
C17 C16 C15 120.9(2) . . ?
O2 C4 O1 126.6(3) . . ?
O2 C4 N1 123.8(2) . . ?
O1 C4 N1 109.6(2) . . ?
O1 C29 C1 102.0(2) . . ?
O1 C29 C3 109.1(2) . . ?
C1 C29 C3 110.6(2) . . ?
O1 C29 C2 110.8(2) . . ?
C1 C29 C2 110.4(3) . . ?
C3 C29 C2 113.3(3) . . ?
O4 C8 N2 123.1(2) . . ?
O4 C8 C6 122.1(2) . . ?
N2 C8 C6 114.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.863
_diffrn_reflns_theta_full        28.13
_diffrn_measured_fraction_theta_full 0.863
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.057