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


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Dhevalapally B. Ramachary'
_publ_contact_author_email       ramchary.db@gmail.com
loop_
_publ_author_name
D.B.Ramachary
R.Madhavachary
'M. Shiva Prasad'

data_dbr22
_database_code_depnum_ccdc_archive 'CCDC 856223'
#TrackingRef 'DBR-22.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 N O5'
_chemical_formula_weight         275.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 '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) '

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                   6.0553(2)
_cell_length_b                   13.8095(5)
_cell_length_c                   15.5347(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1299.02(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1861
_cell_measurement_theta_min      2.8421
_cell_measurement_theta_max      71.6185

_exptl_crystal_description       black
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576.0
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95505
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.3291
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3960
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.28
_diffrn_reflns_theta_max         71.76
_reflns_number_total             2486
_reflns_number_gt                2093
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0536P)^2^+0.1134P] 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   0.3(3)
_refine_ls_number_reflns         2486
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1146
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
C7 C 0.1323(4) 0.56083(18) 0.05592(16) 0.0502(6) Uani 1 1 d . . .
C8 C 0.3790(4) 0.57688(16) 0.05752(15) 0.0437(5) Uani 1 1 d . . .
C9 C 0.4764(3) 0.56100(16) -0.03339(14) 0.0417(5) Uani 1 1 d . . .
H9 H 0.6377 0.5653 -0.0302 0.050 Uiso 1 1 calc R . .
C10 C 0.3919(5) 0.63692(18) -0.09728(16) 0.0541(6) Uani 1 1 d . . .
H10A H 0.2318 0.6350 -0.0988 0.065 Uiso 1 1 calc R . .
H10B H 0.4362 0.7009 -0.0780 0.065 Uiso 1 1 calc R . .
C14 C 0.4248(4) 0.67833(18) 0.09654(16) 0.0499(6) Uani 1 1 d . . .
C13 C 0.5078(5) 0.6665(2) 0.18664(17) 0.0663(7) Uani 1 1 d . . .
H13A H 0.4340 0.7114 0.2252 0.080 Uiso 1 1 calc R . .
H13B H 0.6656 0.6781 0.1893 0.080 Uiso 1 1 calc R . .
C12 C 0.4549(5) 0.5629(2) 0.21073(17) 0.0678(8) Uani 1 1 d . . .
H12A H 0.3063 0.5576 0.2335 0.081 Uiso 1 1 calc R . .
H12B H 0.5585 0.5386 0.2532 0.081 Uiso 1 1 calc R . .
C11 C 0.4769(4) 0.50780(18) 0.12582(15) 0.0514(6) Uani 1 1 d . . .
H11A H 0.3950 0.4475 0.1278 0.062 Uiso 1 1 calc R . .
H11B H 0.6305 0.4936 0.1134 0.062 Uiso 1 1 calc R . .
O5 O 0.0577(3) 0.48481(13) 0.00796(12) 0.0588(5) Uani 1 1 d . . .
O1 O 0.0004(3) 0.60745(14) 0.09504(13) 0.0687(5) Uani 1 1 d . . .
O2 O 0.3996(4) 0.75304(13) 0.05856(13) 0.0703(5) Uani 1 1 d . . .
C4 C 0.4130(4) 0.46054(16) -0.06082(15) 0.0454(5) Uani 1 1 d . . .
N1 N 0.4799(5) 0.61954(16) -0.18573(16) 0.0689(7) Uani 1 1 d . . .
C3 C 0.2057(4) 0.42678(18) -0.03789(16) 0.0501(6) Uani 1 1 d . . .
C5 C 0.5494(5) 0.39923(18) -0.10725(17) 0.0589(7) Uani 1 1 d . . .
H5 H 0.6895 0.4201 -0.1232 0.071 Uiso 1 1 calc R . .
O3 O 0.6736(5) 0.6019(2) -0.19401(17) 0.1022(9) Uani 1 1 d . . .
O4 O 0.3497(6) 0.6261(2) -0.24511(15) 0.1156(11) Uani 1 1 d . . .
C2 C 0.1346(5) 0.3351(2) -0.06042(18) 0.0647(7) Uani 1 1 d . . .
H2 H -0.0049 0.3134 -0.0444 0.078 Uiso 1 1 calc R . .
C6 C 0.4799(6) 0.3078(2) -0.13001(19) 0.0716(9) Uani 1 1 d . . .
H6 H 0.5734 0.2673 -0.1611 0.086 Uiso 1 1 calc R . .
C1 C 0.2756(7) 0.2764(2) -0.1073(2) 0.0746(9) Uani 1 1 d . . .
H1 H 0.2297 0.2147 -0.1234 0.090 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
C7 0.0405(12) 0.0559(13) 0.0541(13) 0.0118(12) 0.0061(11) 0.0020(11)
C8 0.0372(11) 0.0451(12) 0.0488(12) -0.0004(10) 0.0038(10) 0.0010(9)
C9 0.0323(10) 0.0454(11) 0.0474(11) -0.0008(10) 0.0051(9) -0.0020(9)
C10 0.0605(16) 0.0484(13) 0.0535(13) 0.0030(11) 0.0040(13) -0.0052(12)
C14 0.0423(13) 0.0512(13) 0.0561(13) -0.0064(12) 0.0136(11) -0.0012(11)
C13 0.0745(18) 0.0694(17) 0.0550(15) -0.0131(14) 0.0020(14) -0.0041(15)
C12 0.0777(19) 0.0780(18) 0.0476(14) -0.0005(13) -0.0043(14) 0.0020(17)
C11 0.0450(14) 0.0554(14) 0.0539(13) 0.0025(11) -0.0037(11) 0.0037(11)
O5 0.0372(9) 0.0673(11) 0.0719(11) 0.0022(9) 0.0006(8) -0.0088(8)
O1 0.0473(10) 0.0776(12) 0.0811(13) 0.0018(11) 0.0191(10) 0.0103(9)
O2 0.0909(14) 0.0504(10) 0.0696(12) -0.0017(9) 0.0074(12) 0.0019(10)
C4 0.0464(13) 0.0446(12) 0.0451(12) 0.0038(10) -0.0061(11) 0.0006(10)
N1 0.104(2) 0.0478(12) 0.0550(14) 0.0024(10) 0.0098(15) -0.0195(13)
C3 0.0502(13) 0.0500(13) 0.0501(13) 0.0072(11) -0.0106(11) -0.0061(11)
C5 0.0680(18) 0.0569(15) 0.0519(14) -0.0044(12) 0.0020(13) 0.0063(13)
O3 0.111(2) 0.115(2) 0.0802(17) -0.0095(15) 0.0445(15) -0.0071(16)
O4 0.175(3) 0.116(2) 0.0551(13) 0.0104(14) -0.0244(17) -0.029(2)
C2 0.0710(18) 0.0603(16) 0.0630(16) 0.0124(14) -0.0179(15) -0.0191(14)
C6 0.098(3) 0.0545(16) 0.0618(17) -0.0085(13) -0.0063(17) 0.0142(17)
C1 0.111(3) 0.0451(15) 0.0680(19) -0.0003(14) -0.028(2) -0.0047(17)

_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
C7 O1 1.192(3) . ?
C7 O5 1.364(3) . ?
C7 C8 1.511(3) . ?
C8 C11 1.545(3) . ?
C8 C9 1.546(3) . ?
C8 C14 1.551(3) . ?
C9 C4 1.501(3) . ?
C9 C10 1.532(3) . ?
C10 N1 1.493(4) . ?
C14 O2 1.198(3) . ?
C14 C13 1.496(4) . ?
C13 C12 1.514(4) . ?
C12 C11 1.528(4) . ?
O5 C3 1.397(3) . ?
C4 C5 1.385(3) . ?
C4 C3 1.386(3) . ?
N1 O3 1.204(3) . ?
N1 O4 1.217(4) . ?
C3 C2 1.382(4) . ?
C5 C6 1.378(4) . ?
C2 C1 1.385(5) . ?
C6 C1 1.358(5) . ?

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
O1 C7 O5 118.2(2) . . ?
O1 C7 C8 125.1(2) . . ?
O5 C7 C8 116.7(2) . . ?
C7 C8 C11 107.47(19) . . ?
C7 C8 C9 110.0(2) . . ?
C11 C8 C9 113.16(18) . . ?
C7 C8 C14 108.40(19) . . ?
C11 C8 C14 102.75(19) . . ?
C9 C8 C14 114.63(19) . . ?
C4 C9 C10 111.29(19) . . ?
C4 C9 C8 107.02(18) . . ?
C10 C9 C8 111.55(19) . . ?
N1 C10 C9 111.5(2) . . ?
O2 C14 C13 126.7(2) . . ?
O2 C14 C8 124.2(2) . . ?
C13 C14 C8 109.1(2) . . ?
C14 C13 C12 105.3(2) . . ?
C13 C12 C11 103.8(2) . . ?
C12 C11 C8 104.6(2) . . ?
C7 O5 C3 120.50(18) . . ?
C5 C4 C3 117.9(2) . . ?
C5 C4 C9 124.1(2) . . ?
C3 C4 C9 118.0(2) . . ?
O3 N1 O4 124.4(3) . . ?
O3 N1 C10 118.6(3) . . ?
O4 N1 C10 117.0(3) . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 O5 117.0(2) . . ?
C4 C3 O5 121.3(2) . . ?
C6 C5 C4 120.8(3) . . ?
C3 C2 C1 118.6(3) . . ?
C1 C6 C5 120.3(3) . . ?
C6 C1 C2 120.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        71.76
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.031