# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1887487'
_audit_update_record             
;
2018-12-26 deposited with the CCDC.	2019-03-21 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H6 N2 O4'
_chemical_formula_weight         158.12
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   5.6945(6)
_cell_length_b                   17.5460(18)
_cell_length_c                   6.6210(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.106(4)
_cell_angle_gamma                90
_cell_volume                     635.58(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7309
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         3.407
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                968
_reflns_number_total             1112
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    ?
_computing_publication_material  ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    ?
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.201
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0170P)²+0.6828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0964
_refine_special_details          ?
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.2571(4) 0.06628(13) 0.1742(4) 0.0137(6) Uani 1 1 d . . . . .
H1 H 0.102826 0.088317 0.128737 0.016 Uiso 1 1 calc R U . . .
C2 C 0.3068(4) -0.00839(13) 0.2099(4) 0.0134(6) Uani 1 1 d . . . . .
H2 H 0.193571 -0.047695 0.194236 0.016 Uiso 1 1 calc R U . . .
C3 C 0.6534(4) 0.05340(13) 0.2782(4) 0.0135(6) Uani 1 1 d . . . . .
H3 H 0.819694 0.064350 0.317807 0.016 Uiso 1 1 calc R U . . .
C4 C -0.1467(4) 0.26872(13) 0.1701(4) 0.0107(5) Uani 1 1 d . . . . .
C5 C -0.3944(4) 0.30577(13) 0.1677(4) 0.0114(5) Uani 1 1 d . . . . .
N1 N 0.4764(4) 0.10353(11) 0.2172(3) 0.0129(5) Uani 1 1 d . . . . .
H1A H 0.495334 0.151835 0.206269 0.015 Uiso 1 1 calc R U . . .
N2 N 0.5558(4) -0.01525(11) 0.2738(3) 0.0125(5) Uani 1 1 d . . . . .
H2A H 0.635655 -0.057182 0.305818 0.015 Uiso 1 1 calc R U . . .
O1 O -0.1197(3) 0.20046(9) 0.1723(3) 0.0176(4) Uani 1 1 d . . . . .
O2 O 0.0228(3) 0.31960(9) 0.1699(3) 0.0152(4) Uani 1 1 d . . . . .
H2B H 0.150428 0.297821 0.170581 0.023 Uiso 1 1 calc R U . . .
O3 O -0.5623(3) 0.25903(9) 0.1702(3) 0.0148(4) Uani 1 1 d . . . . .
O4 O -0.4103(3) 0.37635(9) 0.1636(3) 0.0151(4) Uani 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 0.0104(12) 0.0156(13) 0.0158(13) 0.0002(10) 0.0047(10) 0.0017(10)
C2 0.0105(12) 0.0128(13) 0.0165(14) -0.0010(10) 0.0032(10) -0.0008(10)
C3 0.0086(12) 0.0152(13) 0.0172(14) 0.0003(10) 0.0044(10) -0.0004(10)
C4 0.0117(12) 0.0116(13) 0.0087(12) -0.0001(10) 0.0027(10) -0.0005(10)
C5 0.0106(12) 0.0121(13) 0.0107(13) -0.0007(10) 0.0015(10) -0.0006(10)
N1 0.0166(11) 0.0078(10) 0.0158(11) -0.0011(8) 0.0071(9) -0.0016(9)
N2 0.0138(11) 0.0084(10) 0.0153(11) 0.0013(8) 0.0043(9) 0.0018(8)
O1 0.0139(9) 0.0098(9) 0.0312(11) 0.0013(8) 0.0096(8) 0.0025(7)
O2 0.0092(9) 0.0102(8) 0.0277(11) 0.0014(7) 0.0074(8) 0.0013(7)
O3 0.0097(9) 0.0111(9) 0.0241(10) 0.0006(7) 0.0057(7) -0.0003(7)
O4 0.0106(9) 0.0093(9) 0.0256(10) -0.0008(7) 0.0052(8) 0.0003(7)

_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 H1 0.9300 . ?
C1 C2 1.347(3) . ?
C1 N1 1.368(3) . ?
C2 H2 0.9300 . ?
C2 N2 1.368(3) . ?
C3 H3 0.9300 . ?
C3 N1 1.314(3) . ?
C3 N2 1.323(3) . ?
C4 C5 1.549(3) . ?
C4 O1 1.207(3) . ?
C4 O2 1.315(3) . ?
C5 O3 1.263(3) . ?
C5 O4 1.241(3) . ?
N1 H1A 0.8600 . ?
N2 H2A 0.8600 . ?
O2 H2B 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 H1 126.5 . . ?
C2 C1 N1 107.0(2) . . ?
N1 C1 H1 126.5 . . ?
C1 C2 H2 126.6 . . ?
C1 C2 N2 106.8(2) . . ?
N2 C2 H2 126.6 . . ?
N1 C3 H3 125.6 . . ?
N1 C3 N2 108.7(2) . . ?
N2 C3 H3 125.6 . . ?
O1 C4 C5 121.9(2) . . ?
O1 C4 O2 125.6(2) . . ?
O2 C4 C5 112.44(19) . . ?
O3 C5 C4 114.68(19) . . ?
O4 C5 C4 118.6(2) . . ?
O4 C5 O3 126.7(2) . . ?
C1 N1 H1A 125.6 . . ?
C3 N1 C1 108.8(2) . . ?
C3 N1 H1A 125.6 . . ?
C2 N2 H2A 125.7 . . ?
C3 N2 C2 108.6(2) . . ?
C3 N2 H2A 125.7 . . ?
C4 O2 H2B 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
C1 C2 N2 C3 0.5(3) . . . . ?
C2 C1 N1 C3 -0.3(3) . . . . ?
N1 C1 C2 N2 -0.1(3) . . . . ?
N1 C3 N2 C2 -0.7(3) . . . . ?
N2 C3 N1 C1 0.7(3) . . . . ?
O1 C4 C5 O3 0.6(3) . . . . ?
O1 C4 C5 O4 -179.3(2) . . . . ?
O2 C4 C5 O3 -179.3(2) . . . . ?
O2 C4 C5 O4 0.8(3) . . . . ?

_shelx_res_file                  
;
TITL SIR92 run in space group P 21/n
    shelx.res
    created by SHELXL-2016/6 at 09:19:51 on 04-Jun-2018
CELL  0.71073   5.6945  17.5460   6.6210   90.000  106.106   90.000
ZERR     4.00   0.0006   0.0018   0.0007    0.000    0.004    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  20 24 8 16
MERG   2
OMIT    -3.00  50.05
OMIT     0   2   0
OMIT     0   3   6
OMIT     2   1   6
OMIT     0   6   7
OMIT    -2  17   4
OMIT     5   5   1
OMIT     0   8   0
OMIT    -2   6   5
FMAP   2
PLAN   20
SIZE     0.150   0.190   0.280
ACTA
BOND   $H
CONF
L.S.  10
TEMP     0.00
WGHT    0.017000    0.682800
EXTI    0.013364
FVAR       0.21254
C1    1    0.257072    0.066279    0.174151    11.00000    0.01044    0.01556 =
         0.01580    0.00019    0.00467    0.00175
AFIX  43
H1    2    0.102826    0.088317    0.128737    11.00000   -1.20000
AFIX   0
C2    1    0.306772   -0.008385    0.209938    11.00000    0.01049    0.01284 =
         0.01645   -0.00104    0.00323   -0.00082
AFIX  43
H2    2    0.193571   -0.047695    0.194236    11.00000   -1.20000
AFIX   0
C3    1    0.653373    0.053400    0.278177    11.00000    0.00856    0.01524 =
         0.01718    0.00026    0.00440   -0.00039
AFIX  43
H3    2    0.819694    0.064350    0.317807    11.00000   -1.20000
AFIX   0
C4    1   -0.146715    0.268722    0.170136    11.00000    0.01170    0.01163 =
         0.00867   -0.00008    0.00266   -0.00053
C5    1   -0.394420    0.305766    0.167729    11.00000    0.01060    0.01213 =
         0.01074   -0.00070    0.00155   -0.00056
N1    3    0.476381    0.103531    0.217246    11.00000    0.01664    0.00781 =
         0.01581   -0.00106    0.00715   -0.00158
AFIX  43
H1A   2    0.495334    0.151835    0.206269    11.00000   -1.20000
AFIX   0
N2    3    0.555810   -0.015245    0.273821    11.00000    0.01383    0.00842 =
         0.01528    0.00134    0.00429    0.00178
AFIX  43
H2A   2    0.635655   -0.057182    0.305818    11.00000   -1.20000
AFIX   0
O1    4   -0.119705    0.200455    0.172261    11.00000    0.01389    0.00984 =
         0.03120    0.00127    0.00964    0.00245
O2    4    0.022813    0.319602    0.169920    11.00000    0.00916    0.01021 =
         0.02769    0.00137    0.00737    0.00135
AFIX 147
H2B   2    0.150428    0.297821    0.170581    11.00000   -1.50000
AFIX   0
O3    4   -0.562255    0.259029    0.170179    11.00000    0.00966    0.01111 =
         0.02408    0.00060    0.00566   -0.00032
O4    4   -0.410260    0.376346    0.163583    11.00000    0.01059    0.00931 =
         0.02563   -0.00076    0.00523    0.00034
HKLF    4




REM  SIR92 run in space group P 21/n
REM R1 =  0.0479 for     968 Fo > 4sig(Fo)  and  0.0593 for all    1112 data
REM    102 parameters refined using      0 restraints

END

WGHT      0.0165      0.6821

REM Highest difference peak  0.271,  deepest hole -0.309,  1-sigma level  0.061
Q1    1   0.7390 -0.1013  0.3171  11.00000  0.05    0.27
Q2    1   0.2117 -0.0634  0.2788  11.00000  0.05    0.23
Q3    1  -0.2520  0.2934  0.1946  11.00000  0.05    0.23
Q4    1   0.1148  0.1967  0.2997  11.00000  0.05    0.21
Q5    1  -0.4721  0.2179  0.2659  11.00000  0.05    0.20
Q6    1   0.2551  0.0400  0.2751  11.00000  0.05    0.19
Q7    1   0.2238 -0.0795  0.1999  11.00000  0.05    0.19
Q8    1  -0.0696  0.1781  0.0589  11.00000  0.05    0.18
Q9    1   0.2923  0.2919  0.1779  11.00000  0.05    0.18
Q10   1   0.7772 -0.0678  0.3259  11.00000  0.05    0.18
Q11   1   0.5153  0.1013  0.3770  11.00000  0.05    0.17
Q12   1   0.2579  0.1573  0.0955  11.00000  0.05    0.17
Q13   1  -0.1807  0.1584  0.1988  11.00000  0.05    0.17
Q14   1   0.5697  0.2025  0.2434  11.00000  0.05    0.17
Q15   1  -0.2311  0.1382  0.0889  11.00000  0.05    0.17
Q16   1   0.2054  0.1564  0.2483  11.00000  0.05    0.17
Q17   1   0.4382 -0.0208  0.2184  11.00000  0.05    0.16
Q18   1   0.4308 -0.1014  0.2556  11.00000  0.05    0.16
Q19   1  -0.3987  0.3827  0.0091  11.00000  0.05    0.16
Q20   1  -0.7430  0.2264  0.0452  11.00000  0.05    0.16
;
_shelx_res_checksum              69344
