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


data_global
_journal_name_full               'RSC Advances'
_journal_coden_cambridge         1500
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
'Bhisma Patel'
'Srimanta Guin'
'Saroj Rout'
'Nilufa Khatun'
'Tuhin Ghosh'
_publ_contact_author_name        'Srimanta Guin'
_publ_contact_author_email       s.guin@iitg.ernet.in

data_4a
_database_code_depnum_ccdc_archive 'CCDC 824583'
#TrackingRef '- final.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 N3 O2'
_chemical_formula_weight         191.19

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           Triclinic
_symmetry_space_group_name_H-M   'P-1 '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2269(8)
_cell_length_b                   10.1265(11)
_cell_length_c                   11.1995(11)
_cell_angle_alpha                84.312(6)
_cell_angle_beta                 86.837(6)
_cell_angle_gamma                76.573(7)
_cell_volume                     902.56(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4450
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      28.480

_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12792
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         28.48
_reflns_number_total             4510
_reflns_number_gt                2747
_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^)+(0.1554P)^2^+0.1646P] 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    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4312
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0782
_refine_ls_wR_factor_ref         0.2489
_refine_ls_wR_factor_gt          0.2253
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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 0.8667(3) 0.7095(3) 0.9722(2) 0.0385(6) Uani 1 1 d . . .
C7 C 1.1578(3) 0.6174(3) 0.9056(2) 0.0374(6) Uani 1 1 d . . .
C4 C 0.5248(3) 0.8165(3) 0.9464(2) 0.0433(6) Uani 1 1 d . . .
C2 C 0.7610(4) 0.7376(3) 1.0713(2) 0.0455(7) Uani 1 1 d . . .
H2 H 0.8050 0.7212 1.1475 0.055 Uiso 1 1 calc R . .
C6 C 0.7987(4) 0.7372(3) 0.8590(2) 0.0478(7) Uani 1 1 d . . .
H6 H 0.8675 0.7198 0.7910 0.057 Uiso 1 1 calc R . .
C8 C 1.4057(4) 0.5393(3) 0.8397(2) 0.0503(7) Uani 1 1 d . . .
H8 H 1.5201 0.5015 0.8361 0.060 Uiso 1 1 calc R . .
C5 C 0.6300(4) 0.7903(3) 0.8473(3) 0.0522(8) Uani 1 1 d . . .
H5 H 0.5862 0.8088 0.7711 0.063 Uiso 1 1 calc R . .
C3 C 0.5920(4) 0.7894(3) 1.0596(2) 0.0479(7) Uani 1 1 d . . .
H3 H 0.5227 0.8063 1.1275 0.058 Uiso 1 1 calc R . .
C9 C 0.2478(4) 0.9042(3) 1.0236(3) 0.0581(8) Uani 1 1 d . . .
H9A H 0.2506 0.8253 1.0792 0.087 Uiso 1 1 calc R . .
H9B H 0.1361 0.9391 0.9964 0.087 Uiso 1 1 calc R . .
H9C H 0.2824 0.9728 1.0627 0.087 Uiso 1 1 calc R . .
O1 O 1.3157(2) 0.5659(2) 0.94518(15) 0.0445(5) Uani 1 1 d . . .
O2 O 0.3584(3) 0.8676(2) 0.92326(19) 0.0567(6) Uani 1 1 d . . .
N1 N 1.0393(3) 0.6542(2) 0.9906(2) 0.0416(6) Uani 1 1 d . . .
N3 N 1.1505(3) 0.6233(3) 0.78946(19) 0.0483(6) Uani 1 1 d . . .
N2 N 1.3178(3) 0.5713(3) 0.7490(2) 0.0537(7) Uani 1 1 d . . .
C10 C 0.4808(4) 0.7462(3) 0.4687(2) 0.0422(6) Uani 1 1 d . . .
C13 C 0.7558(4) 0.8631(3) 0.4324(3) 0.0501(7) Uani 1 1 d . . .
C15 C 0.6142(4) 0.7060(3) 0.5438(2) 0.0486(7) Uani 1 1 d . . .
H15 H 0.6128 0.6390 0.6067 0.058 Uiso 1 1 calc R . .
C11 C 0.4845(4) 0.8480(3) 0.3763(3) 0.0527(8) Uani 1 1 d . . .
H11 H 0.3938 0.8779 0.3267 0.063 Uiso 1 1 calc R . .
C14 C 0.7496(4) 0.7652(3) 0.5255(3) 0.0525(8) Uani 1 1 d . . .
H14 H 0.8383 0.7383 0.5773 0.063 Uiso 1 1 calc R . .
C12 C 0.6234(4) 0.9052(3) 0.3576(3) 0.0532(8) Uani 1 1 d . . .
H12 H 0.6264 0.9718 0.2946 0.064 Uiso 1 1 calc R . .
C16 C 0.2493(3) 0.6577(3) 0.4064(2) 0.0415(6) Uani 1 1 d . . .
C17 C 0.1283(3) 0.6282(3) 0.2499(2) 0.0412(6) Uani 1 1 d . . .
H17 H 0.1010 0.6290 0.1703 0.049 Uiso 1 1 calc R . .
C18 C 0.9125(6) 1.0141(5) 0.3292(4) 0.0861(13) Uani 1 1 d . . .
H18A H 0.9053 0.9814 0.2525 0.129 Uiso 1 1 calc R . .
H18B H 1.0176 1.0390 0.3332 0.129 Uiso 1 1 calc R . .
H18C H 0.8228 1.0923 0.3393 0.129 Uiso 1 1 calc R . .
N4 N 0.3420(3) 0.6839(3) 0.4919(2) 0.0545(7) Uani 1 1 d . . .
N7 N 0.1236(3) 0.5958(2) 0.44629(16) 0.0346(5) Uani 1 1 d . . .
O4 O 0.2581(3) 0.6804(3) 0.2908(2) 0.0697(7) Uani 1 1 d . . .
N6 N 0.0558(4) 0.5800(4) 0.3407(3) 0.0725(9) Uani 1 1 d . . .
O3 O 0.9003(3) 0.9104(3) 0.4212(2) 0.0711(7) Uani 1 1 d . . .
H4N H 0.334(4) 0.640(3) 0.569(3) 0.048(8) Uiso 1 1 d . . .
H1N H 1.055(3) 0.637(3) 1.058(2) 0.030(7) 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
C1 0.0438(14) 0.0369(13) 0.0368(13) -0.0053(10) -0.0034(11) -0.0120(11)
C7 0.0404(14) 0.0394(13) 0.0352(12) -0.0025(10) -0.0040(10) -0.0145(11)
C4 0.0416(15) 0.0403(14) 0.0484(15) -0.0076(11) -0.0071(12) -0.0077(11)
C2 0.0509(16) 0.0549(16) 0.0310(12) -0.0050(11) -0.0055(11) -0.0111(13)
C6 0.0483(16) 0.0580(17) 0.0349(13) -0.0108(12) -0.0042(12) -0.0038(13)
C8 0.0444(15) 0.0657(19) 0.0406(15) -0.0038(13) 0.0011(12) -0.0134(14)
C5 0.0558(18) 0.0593(18) 0.0389(14) -0.0116(12) -0.0113(13) -0.0029(14)
C3 0.0492(16) 0.0536(16) 0.0404(14) -0.0077(12) 0.0043(12) -0.0103(13)
C9 0.0450(17) 0.0550(18) 0.074(2) -0.0109(15) 0.0010(15) -0.0093(14)
O1 0.0428(11) 0.0562(12) 0.0350(9) -0.0041(8) -0.0022(8) -0.0125(9)
O2 0.0449(12) 0.0635(13) 0.0582(13) -0.0086(10) -0.0071(10) -0.0028(10)
N1 0.0445(13) 0.0535(14) 0.0281(11) -0.0056(9) -0.0058(10) -0.0117(10)
N3 0.0463(14) 0.0642(16) 0.0351(12) -0.0057(10) -0.0014(10) -0.0134(12)
N2 0.0537(15) 0.0694(17) 0.0381(13) -0.0054(11) 0.0055(11) -0.0157(13)
C10 0.0435(14) 0.0515(15) 0.0330(12) -0.0081(11) 0.0018(11) -0.0126(12)
C13 0.0559(18) 0.0516(17) 0.0454(15) -0.0098(12) -0.0011(13) -0.0154(14)
C15 0.0526(17) 0.0565(17) 0.0357(13) -0.0043(12) -0.0015(12) -0.0098(14)
C11 0.0508(17) 0.0618(19) 0.0450(15) 0.0049(13) -0.0117(13) -0.0134(14)
C14 0.0504(17) 0.0644(19) 0.0416(15) -0.0025(13) -0.0076(12) -0.0106(14)
C12 0.0650(19) 0.0523(17) 0.0445(15) 0.0025(12) -0.0078(14) -0.0194(15)
C16 0.0435(14) 0.0485(15) 0.0318(12) -0.0058(10) -0.0016(10) -0.0084(12)
C17 0.0473(15) 0.0590(16) 0.0216(11) -0.0031(10) -0.0039(10) -0.0205(13)
C18 0.090(3) 0.088(3) 0.091(3) 0.019(2) -0.009(2) -0.051(3)
N4 0.0578(16) 0.0759(18) 0.0333(12) 0.0003(11) -0.0054(11) -0.0238(13)
N7 0.0354(11) 0.0483(12) 0.0228(9) -0.0006(8) -0.0011(8) -0.0160(9)
O4 0.0737(16) 0.0880(18) 0.0511(13) -0.0058(12) -0.0025(11) -0.0260(14)
N6 0.078(2) 0.083(2) 0.0583(17) -0.0062(15) -0.0156(15) -0.0193(17)
O3 0.0661(15) 0.0862(18) 0.0693(15) 0.0090(13) -0.0143(12) -0.0382(14)

_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(4) . ?
C1 C6 1.391(4) . ?
C1 N1 1.418(4) . ?
C7 N3 1.300(3) . ?
C7 N1 1.340(4) . ?
C7 O1 1.364(3) . ?
C4 C5 1.377(4) . ?
C4 O2 1.376(3) . ?
C4 C3 1.388(4) . ?
C2 C3 1.377(4) . ?
C6 C5 1.375(4) . ?
C8 N2 1.252(4) . ?
C8 O1 1.375(3) . ?
C9 O2 1.429(4) . ?
N3 N2 1.422(4) . ?
C10 C15 1.379(4) . ?
C10 C11 1.390(4) . ?
C10 N4 1.428(4) . ?
C13 C14 1.373(4) . ?
C13 C12 1.373(4) . ?
C13 O3 1.376(4) . ?
C15 C14 1.379(4) . ?
C11 C12 1.394(4) . ?
C16 O4 1.293(3) . ?
C16 N4 1.340(3) . ?
C16 N7 1.363(3) . ?
C17 N6 1.265(4) . ?
C17 O4 1.413(4) . ?
C18 O3 1.413(4) . ?
N7 N6 1.374(3) . ?

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 C6 118.3(3) . . ?
C2 C1 N1 118.6(2) . . ?
C6 C1 N1 123.1(3) . . ?
N3 C7 N1 131.4(2) . . ?
N3 C7 O1 112.8(2) . . ?
N1 C7 O1 115.8(2) . . ?
C5 C4 O2 115.8(2) . . ?
C5 C4 C3 118.8(3) . . ?
O2 C4 C3 125.3(3) . . ?
C3 C2 C1 121.4(2) . . ?
C5 C6 C1 120.2(3) . . ?
N2 C8 O1 113.0(3) . . ?
C4 C5 C6 121.2(3) . . ?
C2 C3 C4 120.0(3) . . ?
C7 O1 C8 102.0(2) . . ?
C4 O2 C9 117.1(2) . . ?
C7 N1 C1 126.5(2) . . ?
C7 N3 N2 104.7(2) . . ?
C8 N2 N3 107.5(2) . . ?
C15 C10 C11 119.0(3) . . ?
C15 C10 N4 118.2(2) . . ?
C11 C10 N4 122.7(2) . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 O3 115.6(3) . . ?
C12 C13 O3 124.9(3) . . ?
C10 C15 C14 120.0(3) . . ?
C12 C11 C10 120.4(3) . . ?
C13 C14 C15 121.2(3) . . ?
C13 C12 C11 119.8(3) . . ?
O4 C16 N4 131.2(3) . . ?
O4 C16 N7 113.3(2) . . ?
N4 C16 N7 115.5(2) . . ?
N6 C17 O4 107.8(2) . . ?
C16 N4 C10 124.2(2) . . ?
C16 N7 N6 102.0(2) . . ?
C16 O4 C17 104.6(2) . . ?
C17 N6 N7 112.2(3) . . ?
C13 O3 C18 118.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        28.48
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.077