# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_BINPA
_database_code_depnum_ccdc_archive 'CCDC 1429137'
_audit_update_record             
;
2015-10-01 deposited with the CCDC.
2016-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H4 N O6, C7 H7 N2'

_chemical_formula_sum            'C15 H11 N3 O6'
_chemical_formula_weight         329.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.6484(5)
_cell_length_b                   16.6146(11)
_cell_length_c                   11.9576(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.1110(10)
_cell_angle_gamma                90
_cell_volume                     1444.23(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      31.01

_exptl_crystal_description       PLATE
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23501
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.171
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2848
_reflns_number_gt                2376
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'



_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²+0.7280P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0172(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2848
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3151(2) 0.56616(11) 0.97585(17) 0.0455(4) Uani 1 1 d . . . . .
H1 H 0.3612 0.6149 0.9589 0.055 Uiso 1 1 calc R U . . .
C2 C 0.3430(3) 0.54095(13) 1.08943(17) 0.0534(5) Uani 1 1 d . . . . .
H2 H 0.4100 0.5737 1.1510 0.064 Uiso 1 1 calc R U . . .
C3 C 0.2746(3) 0.46811(13) 1.11568(17) 0.0547(5) Uani 1 1 d . . . . .
H3 H 0.2982 0.4533 1.1940 0.066 Uiso 1 1 calc R U . . .
C4 C 0.1732(3) 0.41761(12) 1.02898(16) 0.0487(5) Uani 1 1 d . . . . .
H4 H 0.1268 0.3691 1.0464 0.058 Uiso 1 1 calc R U . . .
C5 C 0.1436(2) 0.44266(10) 0.91394(14) 0.0360(4) Uani 1 1 d . . . . .
C6 C 0.2143(2) 0.51494(10) 0.88798(14) 0.0344(4) Uani 1 1 d . . . . .
C7 C 0.0618(2) 0.45495(11) 0.72164(16) 0.0416(4) Uani 1 1 d . . . . .
H7 H 0.0097 0.4443 0.6418 0.050 Uiso 1 1 calc R U . . .
C8 C 0.41318(19) 0.67045(8) 0.58166(12) 0.0258(3) Uani 1 1 d . . . . .
C9 C 0.5548(2) 0.64263(9) 0.54172(13) 0.0309(3) Uani 1 1 d . . . . .
C10 C 0.7380(2) 0.66015(11) 0.59741(15) 0.0395(4) Uani 1 1 d . . . . .
H10 H 0.8286 0.6419 0.5667 0.047 Uiso 1 1 calc R U . . .
C11 C 0.7836(2) 0.70501(11) 0.69883(16) 0.0433(4) Uani 1 1 d . . . . .
H11 H 0.9062 0.7172 0.7376 0.052 Uiso 1 1 calc R U . . .
C12 C 0.6482(2) 0.73197(10) 0.74326(15) 0.0381(4) Uani 1 1 d . . . . .
H12 H 0.6804 0.7613 0.8130 0.046 Uiso 1 1 calc R U . . .
C13 C 0.4639(2) 0.71585(9) 0.68512(13) 0.0285(3) Uani 1 1 d . . . . .
C14 C 0.3187(2) 0.74944(9) 0.73257(13) 0.0293(3) Uani 1 1 d . . . . .
C15 C 0.21134(19) 0.65379(9) 0.52058(12) 0.0273(3) Uani 1 1 d . . . . .
N1 N 0.15893(19) 0.51964(9) 0.76591(13) 0.0394(3) Uani 1 1 d . . . . .
N2 N 0.0495(2) 0.40768(9) 0.80720(13) 0.0415(4) Uani 1 1 d . . . . .
N3 N 0.51193(19) 0.59150(9) 0.43617(12) 0.0382(3) Uani 1 1 d . . . . .
O1 O 0.35682(17) 0.74179(8) 0.84429(10) 0.0479(3) Uani 1 1 d . . . . .
H1A H 0.2733 0.7610 0.8652 0.072 Uiso 1 1 calc R U . . .
O2 O 0.18074(16) 0.78138(8) 0.66786(10) 0.0442(3) Uani 1 1 d . . . . .
O3 O 0.12970(14) 0.60825(7) 0.56818(10) 0.0367(3) Uani 1 1 d . . . . .
O4 O 0.13603(14) 0.68933(7) 0.42258(9) 0.0347(3) Uani 1 1 d . . . . .
O5 O 0.36646(18) 0.55486(8) 0.40686(11) 0.0501(3) Uani 1 1 d . . . . .
O6 O 0.6245(2) 0.58802(10) 0.38314(13) 0.0643(4) Uani 1 1 d . . . . .
H1B H 0.186(3) 0.5575(15) 0.719(2) 0.068(7) Uiso 1 1 d . . . . .
H2A H -0.019(3) 0.3632(15) 0.7991(19) 0.067(7) Uiso 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
C1 C2 1.373(3) . ?
C1 C6 1.385(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.393(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9300 . ?
C5 N2 1.383(2) . ?
C5 C6 1.391(2) . ?
C6 N1 1.390(2) . ?
C7 N2 1.316(2) . ?
C7 N1 1.320(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(2) . ?
C8 C13 1.397(2) . ?
C8 C15 1.514(2) . ?
C9 C10 1.382(2) . ?
C9 N3 1.471(2) . ?
C10 C11 1.373(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.503(2) . ?
C14 O2 1.2190(19) . ?
C14 O1 1.2820(18) . ?
C15 O3 1.2278(18) . ?
C15 O4 1.2782(18) . ?
N1 H1B 0.91(2) . ?
N2 H2A 0.89(2) . ?
N3 O6 1.2188(18) . ?
N3 O5 1.2203(18) . ?
O1 H1A 0.8200 . ?

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 116.22(18) . . ?
C2 C1 H1 121.9 . . ?
C6 C1 H1 121.9 . . ?
C1 C2 C3 122.29(18) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 121.67(18) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 116.49(18) . . ?
C3 C4 H4 121.8 . . ?
C5 C4 H4 121.8 . . ?
N2 C5 C4 131.83(16) . . ?
N2 C5 C6 106.47(14) . . ?
C4 C5 C6 121.70(16) . . ?
C1 C6 N1 132.70(16) . . ?
C1 C6 C5 121.62(16) . . ?
N1 C6 C5 105.68(14) . . ?
N2 C7 N1 109.96(16) . . ?
N2 C7 H7 125.0 . . ?
N1 C7 H7 125.0 . . ?
C9 C8 C13 116.86(13) . . ?
C9 C8 C15 124.02(13) . . ?
C13 C8 C15 119.12(12) . . ?
C10 C9 C8 123.04(14) . . ?
C10 C9 N3 117.19(13) . . ?
C8 C9 N3 119.77(13) . . ?
C11 C10 C9 118.77(14) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 120.11(15) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 120.77(15) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 120.40(14) . . ?
C12 C13 C14 119.54(14) . . ?
C8 C13 C14 120.04(13) . . ?
O2 C14 O1 125.19(14) . . ?
O2 C14 C13 121.16(13) . . ?
O1 C14 C13 113.65(13) . . ?
O3 C15 O4 124.09(14) . . ?
O3 C15 C8 118.57(13) . . ?
O4 C15 C8 117.34(12) . . ?
C7 N1 C6 108.97(15) . . ?
C7 N1 H1B 121.4(15) . . ?
C6 N1 H1B 129.5(15) . . ?
C7 N2 C5 108.93(15) . . ?
C7 N2 H2A 126.2(15) . . ?
C5 N2 H2A 124.5(14) . . ?
O6 N3 O5 123.72(15) . . ?
O6 N3 C9 117.94(15) . . ?
O5 N3 C9 118.33(13) . . ?
C14 O1 H1A 109.5 . . ?

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
C6 C1 C2 C3 0.0(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 N2 -179.88(18) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C2 C1 C6 N1 179.90(17) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
N2 C5 C6 C1 179.13(15) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
N2 C5 C6 N1 -0.15(18) . . . . ?
C4 C5 C6 N1 179.58(15) . . . . ?
C13 C8 C9 C10 -2.1(2) . . . . ?
C15 C8 C9 C10 178.44(14) . . . . ?
C13 C8 C9 N3 177.35(13) . . . . ?
C15 C8 C9 N3 -2.1(2) . . . . ?
C8 C9 C10 C11 2.0(3) . . . . ?
N3 C9 C10 C11 -177.42(15) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 C13 -1.5(3) . . . . ?
C11 C12 C13 C8 1.4(2) . . . . ?
C11 C12 C13 C14 -177.04(15) . . . . ?
C9 C8 C13 C12 0.4(2) . . . . ?
C15 C8 C13 C12 179.87(14) . . . . ?
C9 C8 C13 C14 178.76(13) . . . . ?
C15 C8 C13 C14 -1.7(2) . . . . ?
C12 C13 C14 O2 134.46(17) . . . . ?
C8 C13 C14 O2 -44.0(2) . . . . ?
C12 C13 C14 O1 -44.7(2) . . . . ?
C8 C13 C14 O1 136.90(15) . . . . ?
C9 C8 C15 O3 110.02(17) . . . . ?
C13 C8 C15 O3 -69.46(19) . . . . ?
C9 C8 C15 O4 -70.88(19) . . . . ?
C13 C8 C15 O4 109.64(15) . . . . ?
N2 C7 N1 C6 0.0(2) . . . . ?
C1 C6 N1 C7 -179.06(18) . . . . ?
C5 C6 N1 C7 0.10(18) . . . . ?
N1 C7 N2 C5 -0.1(2) . . . . ?
C4 C5 N2 C7 -179.54(18) . . . . ?
C6 C5 N2 C7 0.15(19) . . . . ?
C10 C9 N3 O6 -22.2(2) . . . . ?
C8 C9 N3 O6 158.31(15) . . . . ?
C10 C9 N3 O5 157.55(15) . . . . ?
C8 C9 N3 O5 -21.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O1 0.93 2.51 3.377(2) 155.3 .
C7 H7 O3 0.93 2.56 3.479(2) 170.9 3_566
C7 H7 O4 0.93 2.50 3.064(2) 119.5 3_566
C10 H10 O3 0.93 2.36 3.2393(19) 156.6 1_655
O1 H1A O4 0.82 1.64 2.4537(15) 169.3 4_576
N1 H1B O3 0.91(2) 1.91(2) 2.7348(18) 149(2) .
N2 H2A O2 0.89(2) 1.96(2) 2.8143(19) 160(2) 2_546

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037

