# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_L2DW22G_0m
_database_code_depnum_ccdc_archive 'CCDC 2049360'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2020-12-09 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H5 N5 O4'
_chemical_formula_weight         187.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c a'
_space_group_name_Hall           '-C 2bc 2'

_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+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   7.7002(7)
_cell_length_b                   14.3978(16)
_cell_length_c                   12.7602(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1414.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3719
_cell_measurement_theta_min      6.1494
_cell_measurement_theta_max      79.8878

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.382
_shelx_estimated_absorpt_T_min   0.809
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6126
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest diffractometer with PhotonIII_C14 charge-integrating and 
photon counting pixel array detector
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            5056
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         6.147
_diffrn_reflns_theta_max         79.922
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             812
_reflns_number_gt                741
_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       'Apex3 v2019.1-0 (Bruker, 2019)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1143 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0842P)²+0.8362P] where P=(Fo²+2Fc²)/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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0052(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         812
_refine_ls_number_parameters     72
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1427
_refine_ls_wR_factor_gt          0.1406
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.160
_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 0.000000 0.29744(15) -0.18427(17) 0.0272(6) Uani 1 2 d S T P . .
H1 H 0.000000 0.232183 -0.173226 0.033 Uiso 1 2 calc R U P . .
C2 C 0.000000 0.34319(15) -0.27768(18) 0.0276(6) Uani 1 2 d S T P . .
H2 H 0.000000 0.316490 -0.345758 0.033 Uiso 1 2 calc R U P . .
C3 C 0.000000 0.51297(16) -0.32694(19) 0.0355(6) Uani 1 2 d S T P . .
H3A H 0.052097 0.493417 -0.393446 0.053 Uiso 0.5 1 calc R U P . .
H3B H 0.067562 0.564336 -0.297327 0.053 Uiso 0.5 1 calc R U P . .
H3C H -0.119658 0.533459 -0.339175 0.053 Uiso 0.5 1 calc R U P . .
C4 C 0.000000 0.35438(15) -0.00123(18) 0.0254(5) Uani 1 2 d S T P . .
N1 N 0.000000 0.36491(13) -0.11074(14) 0.0251(5) Uani 1 2 d S T P . .
N2 N 0.000000 0.45010(13) -0.15185(15) 0.0296(5) Uani 1 2 d S T P . .
N3 N 0.000000 0.43452(13) -0.25325(14) 0.0254(5) Uani 1 2 d S T P . .
N4 N 0.15958(18) 0.35084(9) 0.04807(11) 0.0262(4) Uani 1 1 d . . . . .
O1 O 0.29081(16) 0.35979(9) -0.00925(10) 0.0352(4) Uani 1 1 d . . . . .
O2 O 0.17141(17) 0.33925(8) 0.14400(9) 0.0313(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 0.0313(12) 0.0242(10) 0.0261(11) -0.0022(8) 0.000 0.000
C2 0.0322(12) 0.0285(11) 0.0222(11) -0.0031(7) 0.000 0.000
C3 0.0512(16) 0.0277(11) 0.0275(11) 0.0061(9) 0.000 0.000
C4 0.0230(12) 0.0326(11) 0.0207(11) 0.0017(7) 0.000 0.000
N1 0.0285(10) 0.0262(9) 0.0206(10) 0.0001(6) 0.000 0.000
N2 0.0412(12) 0.0257(9) 0.0220(10) 0.0003(7) 0.000 0.000
N3 0.0297(10) 0.0262(9) 0.0202(9) 0.0013(6) 0.000 0.000
N4 0.0288(8) 0.0260(7) 0.0239(8) -0.0003(4) 0.0005(5) -0.0007(5)
O1 0.0255(8) 0.0472(8) 0.0327(7) -0.0026(5) 0.0063(5) -0.0051(5)
O2 0.0337(7) 0.0381(7) 0.0223(7) 0.0028(4) -0.0048(4) -0.0008(5)

_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 N1 1.351(3) . ?
C1 C2 1.362(3) . ?
C1 H1 0.9500 . ?
C2 N3 1.351(3) . ?
C2 H2 0.9500 . ?
C3 N3 1.470(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3 H3A 0.980(16) 12 ?
C3 H3B 0.98(2) 12 ?
C3 H3C 0.980(3) 12 ?
C4 N4 1.3814(17) 12 ?
C4 N4 1.3814(17) . ?
C4 N1 1.406(3) . ?
N1 N2 1.334(2) . ?
N2 N3 1.313(3) . ?
N4 O2 1.2387(18) . ?
N4 O1 1.2541(18) . ?

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
N1 C1 C2 105.07(19) . . ?
N1 C1 H1 127.5 . . ?
C2 C1 H1 127.5 . . ?
N3 C2 C1 105.60(19) . . ?
N3 C2 H2 127.2 . . ?
C1 C2 H2 127.2 . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N3 C3 H3A 109.5(4) . 12 ?
H3A C3 H3A 48.3 . 12 ?
H3B C3 H3A 140.2 . 12 ?
H3C C3 H3A 64.1 . 12 ?
N3 C3 H3B 109.5(4) . 12 ?
H3A C3 H3B 140.2 . 12 ?
H3B C3 H3B 64.1 . 12 ?
H3C C3 H3B 48.3 . 12 ?
H3A C3 H3B 109.5 12 12 ?
N3 C3 H3C 109.47(7) . 12 ?
H3A C3 H3C 64.1 . 12 ?
H3B C3 H3C 48.3 . 12 ?
H3C C3 H3C 140.2 . 12 ?
H3A C3 H3C 109.5 12 12 ?
H3B C3 H3C 109.5 12 12 ?
N4 C4 N4 125.6(2) 12 . ?
N4 C4 N1 117.18(10) 12 . ?
N4 C4 N1 117.18(10) . . ?
N2 N1 C1 112.84(18) . . ?
N2 N1 C4 119.34(17) . . ?
C1 N1 C4 127.82(19) . . ?
N3 N2 N1 103.32(16) . . ?
N2 N3 C2 113.17(18) . . ?
N2 N3 C3 119.94(18) . . ?
C2 N3 C3 126.89(19) . . ?
O2 N4 O1 122.06(14) . . ?
O2 N4 C4 121.36(14) . . ?
O1 N4 C4 116.58(14) . . ?

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
N1 C1 C2 N3 0.000(0) . . . . ?
C2 C1 N1 N2 0.000(0) . . . . ?
C2 C1 N1 C4 180.000(0) . . . . ?
N4 C4 N1 N2 89.20(16) 12 . . . ?
N4 C4 N1 N2 -89.20(16) . . . . ?
N4 C4 N1 C1 -90.80(16) 12 . . . ?
N4 C4 N1 C1 90.80(16) . . . . ?
C1 N1 N2 N3 0.000(0) . . . . ?
C4 N1 N2 N3 180.000(0) . . . . ?
N1 N2 N3 C2 0.000(0) . . . . ?
N1 N2 N3 C3 180.000(0) . . . . ?
C1 C2 N3 N2 0.000(0) . . . . ?
C1 C2 N3 C3 180.000(0) . . . . ?
N4 C4 N4 O2 3.7(3) 12 . . . ?
N1 C4 N4 O2 -178.09(15) . . . . ?
N4 C4 N4 O1 -176.46(14) 12 . . . ?
N1 C4 N4 O1 1.8(2) . . . . ?

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.063

_shelx_res_file                  
;
TITL L2DW22G_0m in Cmca
    L2DW22G_0m.res
    created by SHELXL-2018/3 at 13:00:24 on 12-Sep-2020
CELL 1.54178   7.70020  14.39779  12.76020  90.0000  90.0000  90.0000
ZERR    8.00   0.00070   0.00157   0.00110   0.0000   0.0000   0.0000
LATT  7
SYMM -X, 0.5-Y, 0.5+Z
SYMM -X, 0.5+Y, 0.5-Z
SYMM X, -Y, -Z
SFAC C H N O
UNIT 32 40 40 32
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
TEMP -123.150
SIZE 0.02 0.15 0.16

L.S. 4
BOND $H
ACTA
CONF
FMAP 2
PLAN 20
WGHT    0.084200    0.836200
EXTI    0.005207
FVAR       0.72338
C1    1    0.000000    0.297435   -0.184272    10.50000    0.03133    0.02419 =
         0.02611   -0.00221    0.00000    0.00000
AFIX  43
H1    2    0.000000    0.232183   -0.173226    10.50000   -1.20000
AFIX   0
C2    1    0.000000    0.343189   -0.277675    10.50000    0.03221    0.02851 =
         0.02215   -0.00313    0.00000    0.00000
AFIX  43
H2    2    0.000000    0.316490   -0.345758    10.50000   -1.20000
AFIX   0
C3    1    0.000000    0.512967   -0.326936    10.50000    0.05123    0.02771 =
         0.02750    0.00606    0.00000    0.00000
AFIX 137
H3A   2    0.052097    0.493417   -0.393446    10.50000   -1.50000
H3B   2    0.067562    0.564336   -0.297327    10.50000   -1.50000
H3C   2   -0.119658    0.533459   -0.339175    10.50000   -1.50000
AFIX   0
C4    1    0.000000    0.354383   -0.001235    10.50000    0.02297    0.03258 =
         0.02065    0.00169    0.00000    0.00000
N1    3    0.000000    0.364907   -0.110741    10.50000    0.02846    0.02623 =
         0.02059    0.00010    0.00000    0.00000
N2    3    0.000000    0.450102   -0.151849    10.50000    0.04117    0.02575 =
         0.02198    0.00028    0.00000    0.00000
N3    3    0.000000    0.434524   -0.253250    10.50000    0.02973    0.02621 =
         0.02017    0.00128    0.00000    0.00000
N4    3    0.159576    0.350844    0.048069    11.00000    0.02880    0.02598 =
         0.02387   -0.00030    0.00053   -0.00069
O1    4    0.290811    0.359789   -0.009248    11.00000    0.02553    0.04722 =
         0.03272   -0.00256    0.00627   -0.00510
O2    4    0.171408    0.339252    0.143996    11.00000    0.03367    0.03808 =
         0.02229    0.00285   -0.00483   -0.00080
HKLF 4




REM  L2DW22G_0m in Cmca
REM wR2 = 0.1427, GooF = S = 1.160, Restrained GooF = 1.160 for all data
REM R1 = 0.0461 for 741 Fo > 4sig(Fo) and 0.0483 for all 812 data
REM 72 parameters refined using 0 restraints

END

WGHT      0.0842      0.8368

REM Highest difference peak  0.321,  deepest hole -0.249,  1-sigma level  0.063
Q1    1   0.0000  0.2448 -0.1236  10.50000  0.05    0.28
Q2    1   0.0000  0.4552 -0.4965  10.50000  0.05    0.24
Q3    1   0.0000  0.3140 -0.2324  10.50000  0.05    0.22
Q4    1   0.0000  0.3329 -0.3729  10.50000  0.05    0.22
Q5    1   0.0000  0.3614  0.1071  10.50000  0.05    0.21
Q6    1   0.2858  0.3503 -0.0962  11.00000  0.05    0.19
Q7    1   0.1502  0.3411 -0.0570  11.00000  0.05    0.19
Q8    1   0.1651  0.4325  0.1103  11.00000  0.05    0.18
Q9    1   0.3321  0.3391  0.1495  11.00000  0.05    0.18
Q10   1   0.0000  0.3509  0.1520  10.50000  0.05    0.18
Q11   1  -0.1584  0.5364 -0.3042  11.00000  0.05    0.17
Q12   1   0.1737  0.4292  0.0027  11.00000  0.05    0.17
Q13   1   0.0000  0.2745 -0.1807  10.50000  0.05    0.17
Q14   1   0.1396  0.4952 -0.3747  11.00000  0.05    0.17
Q15   1   0.1656  0.4235  0.1949  11.00000  0.05    0.17
Q16   1   0.1445  0.2509  0.1818  11.00000  0.05    0.17
Q17   1   0.0000  0.2477 -0.0180  10.50000  0.05    0.17
Q18   1   0.1686  0.2832 -0.0159  11.00000  0.05    0.16
Q19   1   0.0000  0.3076  0.1822  10.50000  0.05    0.16
Q20   1   0.0680  0.2320 -0.1449  11.00000  0.05    0.16
;
_shelx_res_checksum              21122
