# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1058823'
_audit_update_record             
;
2015-07-24 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'isonicotinamidium picrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N5 O8'
_chemical_formula_sum            'C12 H9 N5 O8'
_chemical_formula_weight         351.24

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           MONOCLINIC
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_HALL  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.290(5)
_cell_length_b                   7.430(5)
_cell_length_c                   14.697(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 116.638(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1394.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4279
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      31.47

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28313
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         31.47
_reflns_number_total             4279
_reflns_number_gt                2706
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2009)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0440P)²+1.7100P] where P=(Fo²+2Fc²)/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_number_reflns         4279
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1711
_refine_ls_wR_factor_gt          0.1482
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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
O8 O 0.53282(13) 0.2055(3) 0.99539(12) 0.0406(4) Uani 1 1 d . . .
N5 N 0.71992(15) 0.1268(3) 0.98113(15) 0.0351(5) Uani 1 1 d . . .
O1 O 0.68226(15) 0.3168(3) 0.68874(16) 0.0533(5) Uani 1 1 d . . .
N2 N 0.51114(18) 0.3380(3) 0.58306(16) 0.0467(6) Uani 1 1 d . . .
H2A H 0.5169 0.2775 0.5359 0.056 Uiso 1 1 calc R . .
H2B H 0.4510 0.3781 0.5736 0.056 Uiso 1 1 calc R . .
C3 C 0.57894(17) 0.4695(3) 0.75157(16) 0.0265(4) Uani 1 1 d . . .
N1 N 0.56509(15) 0.6349(3) 0.90991(14) 0.0328(4) Uani 1 1 d . . .
H1A H 0.5607 0.6859 0.9604 0.039 Uiso 1 1 calc R . .
C12 C 0.61579(16) 0.0919(3) 0.89924(16) 0.0270(4) Uani 1 1 d . . .
C11 C 0.61145(17) 0.0149(3) 0.81284(16) 0.0286(5) Uani 1 1 d . . .
H11 H 0.6724 -0.0112 0.8074 0.034 Uiso 1 1 calc R . .
C7 C 0.52573(17) 0.1367(3) 0.91541(16) 0.0277(4) Uani 1 1 d . . .
N4 N 0.50708(17) -0.1023(3) 0.64101(15) 0.0369(5) Uani 1 1 d . . .
C6 C 0.59476(19) 0.3694(3) 0.67006(18) 0.0329(5) Uani 1 1 d . . .
O2 O 0.73503(17) 0.2564(3) 1.03547(17) 0.0624(6) Uani 1 1 d . . .
N3 N 0.33061(16) 0.1057(4) 0.83414(16) 0.0451(6) Uani 1 1 d . . .
O7 O 0.32344(16) 0.2142(4) 0.89222(17) 0.0704(8) Uani 1 1 d . . .
C2 C 0.48220(17) 0.4963(3) 0.74998(17) 0.0318(5) Uani 1 1 d . . .
H2 H 0.4213 0.4583 0.6946 0.038 Uiso 1 1 calc R . .
C4 C 0.66779(18) 0.5303(3) 0.83434(18) 0.0331(5) Uani 1 1 d . . .
H4 H 0.7332 0.5143 0.8363 0.040 Uiso 1 1 calc R . .
C10 C 0.51407(17) -0.0231(3) 0.73358(16) 0.0292(5) Uani 1 1 d . . .
O4 O 0.58709(16) -0.1281(4) 0.63306(15) 0.0610(6) Uani 1 1 d . . .
C8 C 0.42896(17) 0.0842(3) 0.82925(16) 0.0297(5) Uani 1 1 d . . .
C1 C 0.47740(18) 0.5798(3) 0.83125(18) 0.0344(5) Uani 1 1 d . . .
H1 H 0.4130 0.5978 0.8313 0.041 Uiso 1 1 calc R . .
C9 C 0.42295(18) 0.0080(3) 0.74186(16) 0.0313(5) Uani 1 1 d . . .
H9 H 0.3584 -0.0223 0.6888 0.038 Uiso 1 1 calc R . .
O3 O 0.78931(15) 0.0193(3) 0.99160(17) 0.0625(6) Uani 1 1 d . . .
O5 O 0.42054(16) -0.1423(4) 0.57355(15) 0.0629(7) Uani 1 1 d . . .
C5 C 0.65945(19) 0.6140(3) 0.91340(19) 0.0363(5) Uani 1 1 d . . .
H5 H 0.7190 0.6559 0.9690 0.044 Uiso 1 1 calc R . .
O6 O 0.25762(16) 0.0098(4) 0.77999(19) 0.0808(9) Uani 1 1 d . . .


_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
O8 C7 1.244(3) . ?
N5 O2 1.207(3) . ?
N5 O3 1.228(3) . ?
N5 C12 1.458(3) . ?
O1 C6 1.218(3) . ?
N2 C6 1.322(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C3 C4 1.382(3) . ?
C3 C2 1.387(3) . ?
C3 C6 1.511(3) . ?
N1 C1 1.332(3) . ?
N1 C5 1.335(3) . ?
N1 H1A 0.8600 . ?
C12 C11 1.368(3) . ?
C12 C7 1.448(3) . ?
C11 C10 1.385(3) . ?
C11 H11 0.9300 . ?
C7 C8 1.448(3) . ?
N4 O4 1.216(3) . ?
N4 O5 1.225(3) . ?
N4 C10 1.444(3) . ?
N3 O7 1.211(3) . ?
N3 O6 1.218(3) . ?
N3 C8 1.448(3) . ?
C2 C1 1.375(3) . ?
C2 H2 0.9300 . ?
C4 C5 1.369(3) . ?
C4 H4 0.9300 . ?
C10 C9 1.380(3) . ?
C8 C9 1.371(3) . ?
C1 H1 0.9300 . ?
C9 H9 0.9300 . ?
C5 H5 0.9300 . ?

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
O2 N5 O3 122.8(2) . . ?
O2 N5 C12 120.1(2) . . ?
O3 N5 C12 117.1(2) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C4 C3 C2 118.9(2) . . ?
C4 C3 C6 116.98(19) . . ?
C2 C3 C6 124.0(2) . . ?
C1 N1 C5 122.6(2) . . ?
C1 N1 H1A 118.7 . . ?
C5 N1 H1A 118.7 . . ?
C11 C12 C7 125.05(19) . . ?
C11 C12 N5 116.45(19) . . ?
C7 C12 N5 118.48(19) . . ?
C12 C11 C10 118.4(2) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
O8 C7 C8 125.3(2) . . ?
O8 C7 C12 123.2(2) . . ?
C8 C7 C12 111.41(19) . . ?
O4 N4 O5 122.4(2) . . ?
O4 N4 C10 119.0(2) . . ?
O5 N4 C10 118.7(2) . . ?
O1 C6 N2 123.6(2) . . ?
O1 C6 C3 118.9(2) . . ?
N2 C6 C3 117.5(2) . . ?
O7 N3 O6 122.1(2) . . ?
O7 N3 C8 119.9(2) . . ?
O6 N3 C8 118.0(2) . . ?
C1 C2 C3 119.2(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C9 C10 C11 121.5(2) . . ?
C9 C10 N4 118.8(2) . . ?
C11 C10 N4 119.6(2) . . ?
C9 C8 N3 116.0(2) . . ?
C9 C8 C7 124.4(2) . . ?
N3 C8 C7 119.6(2) . . ?
N1 C1 C2 119.9(2) . . ?
N1 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C8 C9 C10 119.1(2) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
N1 C5 C4 119.4(2) . . ?
N1 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?

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
O2 N5 C12 C11 146.3(2) . . . . ?
O3 N5 C12 C11 -34.1(3) . . . . ?
O2 N5 C12 C7 -35.0(3) . . . . ?
O3 N5 C12 C7 144.7(2) . . . . ?
C7 C12 C11 C10 0.4(4) . . . . ?
N5 C12 C11 C10 179.1(2) . . . . ?
C11 C12 C7 O8 179.5(2) . . . . ?
N5 C12 C7 O8 0.9(3) . . . . ?
C11 C12 C7 C8 1.9(3) . . . . ?
N5 C12 C7 C8 -176.7(2) . . . . ?
C4 C3 C6 O1 13.9(3) . . . . ?
C2 C3 C6 O1 -163.2(2) . . . . ?
C4 C3 C6 N2 -168.6(2) . . . . ?
C2 C3 C6 N2 14.3(3) . . . . ?
C4 C3 C2 C1 -1.0(4) . . . . ?
C6 C3 C2 C1 176.0(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C6 C3 C4 C5 -176.7(2) . . . . ?
C12 C11 C10 C9 -2.7(3) . . . . ?
C12 C11 C10 N4 179.3(2) . . . . ?
O4 N4 C10 C9 179.2(2) . . . . ?
O5 N4 C10 C9 -1.3(4) . . . . ?
O4 N4 C10 C11 -2.6(4) . . . . ?
O5 N4 C10 C11 176.8(2) . . . . ?
O7 N3 C8 C9 -159.0(3) . . . . ?
O6 N3 C8 C9 22.4(4) . . . . ?
O7 N3 C8 C7 23.1(4) . . . . ?
O6 N3 C8 C7 -155.6(3) . . . . ?
O8 C7 C8 C9 -179.8(2) . . . . ?
C12 C7 C8 C9 -2.3(3) . . . . ?
O8 C7 C8 N3 -2.1(4) . . . . ?
C12 C7 C8 N3 175.4(2) . . . . ?
C5 N1 C1 C2 0.6(4) . . . . ?
C3 C2 C1 N1 0.5(4) . . . . ?
N3 C8 C9 C10 -177.5(2) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C11 C10 C9 C8 2.3(4) . . . . ?
N4 C10 C9 C8 -179.6(2) . . . . ?
C1 N1 C5 C4 -1.1(4) . . . . ?
C3 C4 C5 N1 0.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.925
_diffrn_reflns_theta_full        31.47
_diffrn_measured_fraction_theta_full 0.925
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.073
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_preparation       Luminescent
