# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_sztr2
_database_code_depnum_ccdc_archive 'CCDC 1968422'
loop_
_audit_author_name
_audit_author_address
'Adam Pietraszko'
;INTIBS PAN
Poland
;
_audit_update_record             
;
2019-11-27 deposited with the CCDC.	2020-01-21 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 N3 O4'
_chemical_formula_weight         159.11

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.6000(5)
_cell_length_b                   7.2286(6)
_cell_length_c                   8.4078(8)
_cell_angle_alpha                109.170(8)
_cell_angle_beta                 93.810(7)
_cell_angle_gamma                103.285(7)
_cell_volume                     309.12(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    6732
_cell_measurement_theta_min      3
_cell_measurement_theta_max      60.08

_exptl_crystal_description       UNSHAPED
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_F_000             164
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'EMPIRICAL CORRECTION'
_exptl_absorpt_correction_T_min  0.75438
_exptl_absorpt_correction_T_max  1.00121
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'RIGAKU oXFOR DIFFRACTION'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6732
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.596
_diffrn_reflns_theta_max         30.038
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1644
_reflns_number_gt                1112
_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       'CRYSALISPRO 1.171.38.43'
_computing_cell_refinement       'CRYSALISPRO 1.171.38.43'
_computing_data_reduction        'CRYSALISPRO 1.171.38.43'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 3.2'
_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)+(0.0539P)²+0.0505P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1644
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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
O3 O 0.2129(2) -0.00316(18) 0.24556(15) 0.0380(4) Uani 1 1 d . . . . .
O2 O 0.85128(19) 0.11728(18) 0.37440(15) 0.0373(4) Uani 1 1 d . . . . .
H2O H 0.964272 0.073436 0.332701 0.056 Uiso 1 1 calc R U . . .
O4 O 0.4519(2) 0.22994(19) 0.47997(16) 0.0402(4) Uani 1 1 d . . . . .
O1 O 0.6140(2) -0.1285(2) 0.14457(18) 0.0537(5) Uani 1 1 d . . . . .
N3 N 1.0979(3) 0.6907(2) 0.93136(18) 0.0340(4) Uani 1 1 d . . . . .
H3 H 1.146098 0.790220 1.027045 0.041 Uiso 1 1 calc R U . . .
N1 N 0.8646(3) 0.4639(2) 0.71231(19) 0.0343(4) Uani 1 1 d . . . . .
H1 H 0.737228 0.387117 0.637803 0.041 Uiso 1 1 calc R U . . .
N4 N 1.2523(3) 0.5934(2) 0.83869(19) 0.0389(4) Uani 1 1 d . . . . .
C7 C 0.4184(3) 0.0892(2) 0.3419(2) 0.0285(4) Uani 1 1 d . . . . .
C6 C 0.6400(3) 0.0121(2) 0.2752(2) 0.0295(4) Uani 1 1 d . . . . .
C2 C 0.8663(3) 0.6130(3) 0.8560(2) 0.0345(4) Uani 1 1 d . . . . .
H2 H 0.729273 0.654662 0.895688 0.041 Uiso 1 1 calc R U . . .
C5 C 1.1042(3) 0.4568(3) 0.7064(2) 0.0377(5) Uani 1 1 d . . . . .
H5 H 1.155725 0.365078 0.618315 0.045 Uiso 1 1 calc R U . . .

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
O3 0.0211(6) 0.0449(7) 0.0318(7) -0.0075(6) -0.0003(5) 0.0100(5)
O2 0.0196(6) 0.0433(8) 0.0337(7) -0.0066(6) 0.0017(5) 0.0100(5)
O4 0.0257(6) 0.0426(7) 0.0323(7) -0.0122(6) 0.0016(5) 0.0091(5)
O1 0.0321(7) 0.0589(9) 0.0400(8) -0.0229(7) -0.0005(6) 0.0159(6)
N3 0.0349(8) 0.0321(8) 0.0234(8) -0.0035(6) 0.0020(6) 0.0075(6)
N1 0.0254(7) 0.0349(8) 0.0297(8) -0.0020(7) -0.0007(6) 0.0046(6)
N4 0.0304(8) 0.0410(9) 0.0314(9) -0.0043(7) 0.0012(6) 0.0090(7)
C7 0.0218(7) 0.0304(8) 0.0263(9) 0.0013(7) 0.0031(6) 0.0069(6)
C6 0.0226(8) 0.0327(9) 0.0246(9) -0.0006(8) 0.0024(6) 0.0071(7)
C2 0.0324(9) 0.0355(10) 0.0315(10) 0.0049(8) 0.0057(7) 0.0115(7)
C5 0.0313(9) 0.0394(10) 0.0303(10) -0.0040(8) 0.0031(7) 0.0108(8)

_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
O3 C7 1.2626(19) . ?
O2 C6 1.3087(18) . ?
O2 H2O 0.8200 . ?
O4 C7 1.2353(19) . ?
O1 C6 1.1991(19) . ?
N3 C2 1.312(2) . ?
N3 N4 1.363(2) . ?
N3 H3 0.8600 . ?
N1 C2 1.326(2) . ?
N1 C5 1.358(2) . ?
N1 H1 0.8600 . ?
N4 C5 1.296(2) . ?
C7 C6 1.539(2) . ?
C2 H2 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
C6 O2 H2O 109.5 . . ?
C2 N3 N4 111.38(14) . . ?
C2 N3 H3 124.3 . . ?
N4 N3 H3 124.3 . . ?
C2 N1 C5 106.27(15) . . ?
C2 N1 H1 126.9 . . ?
C5 N1 H1 126.9 . . ?
C5 N4 N3 103.67(14) . . ?
O4 C7 O3 125.86(15) . . ?
O4 C7 C6 119.62(14) . . ?
O3 C7 C6 114.52(14) . . ?
O1 C6 O2 125.53(15) . . ?
O1 C6 C7 121.69(15) . . ?
O2 C6 C7 112.77(13) . . ?
N3 C2 N1 107.00(15) . . ?
N3 C2 H2 126.5 . . ?
N1 C2 H2 126.5 . . ?
N4 C5 N1 111.68(16) . . ?
N4 C5 H5 124.2 . . ?
N1 C5 H5 124.2 . . ?

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
C2 N3 N4 C5 0.2(2) . . . . ?
O4 C7 C6 O1 177.52(17) . . . . ?
O3 C7 C6 O1 -2.1(3) . . . . ?
O4 C7 C6 O2 -3.3(3) . . . . ?
O3 C7 C6 O2 177.07(15) . . . . ?
N4 N3 C2 N1 -0.2(2) . . . . ?
C5 N1 C2 N3 0.1(2) . . . . ?
N3 N4 C5 N1 -0.1(2) . . . . ?
C2 N1 C5 N4 0.0(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
_geom_hbond_publ_flag
O2 H2O O3 0.82 1.73 2.5522(16) 176.2 1_655 yes
O2 H2O O4 0.82 2.74 3.2610(16) 123.6 1_655 yes
N3 H3 O3 0.86 1.90 2.7515(19) 172.7 1_666 yes
N3 H3 O1 0.86 2.60 3.052(2) 114.0 1_666 yes
N1 H1 O2 0.86 2.65 3.0930(19) 113.0 . yes
N1 H1 O4 0.86 1.87 2.7297(19) 177.2 . yes
C2 H2 O1 0.93 2.40 3.173(2) 140.9 1_566 yes
C2 H2 N4 0.93 2.59 3.400(2) 145.9 1_455 yes
C5 H5 O2 0.93 2.46 3.033(2) 120.1 . yes
C5 H5 O4 0.93 2.31 3.164(2) 153.5 1_655 yes

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.054

_shelx_res_file                  
;
TITL sz_tri_2_a.res in P-1
    sztr2.res
    created by SHELXL-2018/3 at 15:42:35 on 26-Nov-2019
REM Old TITL sz_tri_2 in P-1
REM SHELXT solution in P-1
REM R1 0.235, Rweak 0.008, Alpha 0.030, Orientation as input
REM Formula found by SHELXT: C7 N O3
CELL 0.71073 5.6 7.2286 8.4078 109.17 93.81 103.285
ZERR 2 0.0005 0.0006 0.0008 0.008 0.007 0.007
LATT 1
SFAC C H N O
UNIT 8 10 6 8
TEMP   295
L.S. 21

HTAB  2.8
PLAN  20
BOND $H
EQIV $1 x+1, y, z
HTAB O2 O3_$1
HTAB O2 O4_$1
EQIV $2 x+1, y+1, z+1
HTAB N3 O3_$2
HTAB N3 O1_$2
HTAB N1 O2
HTAB N1 O4
EQIV $3 x, y+1, z+1
HTAB C2 O1_$3
EQIV $4 x-1, y, z
HTAB C2 N4_$4
HTAB C5 O2
HTAB C5 O4_$1

FMAP  2
ACTA
CONF
REM <olex2.extras>
REM <HklSrc "%.\\sz_tri_2.hkl">
REM </olex2.extras>
WGHT    0.053900    0.050500
EXTI    0.005462
FVAR       0.96974
O3    4    0.212853   -0.003164    0.245561    11.00000    0.02106    0.04487 =
         0.03182   -0.00754   -0.00029    0.00999
O2    4    0.851281    0.117280    0.374399    11.00000    0.01955    0.04332 =
         0.03374   -0.00663    0.00169    0.01001
AFIX 147
H2O   2    0.964272    0.073436    0.332701    11.00000   -1.50000
AFIX   0
O4    4    0.451912    0.229936    0.479971    11.00000    0.02566    0.04257 =
         0.03230   -0.01219    0.00164    0.00906
O1    4    0.614047   -0.128479    0.144567    11.00000    0.03207    0.05885 =
         0.03997   -0.02285   -0.00053    0.01585
N3    3    1.097875    0.690674    0.931356    11.00000    0.03489    0.03214 =
         0.02341   -0.00353    0.00201    0.00754
AFIX  43
H3    2    1.146098    0.790220    1.027045    11.00000   -1.20000
AFIX   0
N1    3    0.864590    0.463921    0.712314    11.00000    0.02541    0.03495 =
         0.02968   -0.00200   -0.00066    0.00458
AFIX  43
H1    2    0.737228    0.387117    0.637803    11.00000   -1.20000
AFIX   0
N4    3    1.252340    0.593437    0.838686    11.00000    0.03038    0.04101 =
         0.03140   -0.00428    0.00117    0.00901
C7    1    0.418392    0.089182    0.341870    11.00000    0.02184    0.03036 =
         0.02631    0.00131    0.00308    0.00694
C6    1    0.639997    0.012087    0.275198    11.00000    0.02256    0.03273 =
         0.02463   -0.00058    0.00236    0.00710
C2    1    0.866275    0.613035    0.855954    11.00000    0.03236    0.03552 =
         0.03151    0.00485    0.00572    0.01154
AFIX  43
H2    2    0.729273    0.654662    0.895688    11.00000   -1.20000
AFIX   0
C5    1    1.104248    0.456768    0.706422    11.00000    0.03133    0.03940 =
         0.03026   -0.00395    0.00307    0.01077
AFIX  43
H5    2    1.155725    0.365078    0.618315    11.00000   -1.20000
AFIX   0
HKLF 4




REM  sz_tri_2_a.res in P-1
REM wR2 = 0.1261, GooF = S = 1.112, Restrained GooF = 1.112 for all data
REM R1 = 0.0465 for 1112 Fo > 4sig(Fo) and 0.0828 for all 1644 data
REM 102 parameters refined using 0 restraints

END

WGHT      0.0535      0.0505

REM Instructions for potential hydrogen bonds
HTAB O2 O3_$1
HTAB O2 O4_$1
HTAB N3 O3_$2
HTAB N3 O1_$2
HTAB N1 O2
HTAB N1 O4
HTAB C2 O1_$3
HTAB C2 N4_$4
HTAB C5 O2
HTAB C5 O4_$1

REM Highest difference peak  0.268,  deepest hole -0.239,  1-sigma level  0.054
Q1    1   0.5319  0.0560  0.3110  11.00000  0.05    0.27
Q2    1   1.4284  0.6648  0.9031  11.00000  0.05    0.26
Q3    1   0.8815  0.2317  0.4798  11.00000  0.05    0.22
Q4    1   0.4577 -0.1759  0.0769  11.00000  0.05    0.21
Q5    1   1.4610  0.5822  0.8345  11.00000  0.05    0.20
Q6    1   0.6282  0.2912  0.5484  11.00000  0.05    0.19
Q7    1   0.1732  0.0672  0.2758  11.00000  0.05    0.17
Q8    1   0.9509  0.4485  0.7055  11.00000  0.05    0.17
Q9    1   0.6491 -0.0983  0.1201  11.00000  0.05    0.17
Q10   1   0.6309  0.2263  0.4643  11.00000  0.05    0.17
Q11   1   1.3054  0.5030  0.9129  11.00000  0.05    0.16
Q12   1   0.4980  0.3587  0.5623  11.00000  0.05    0.15
Q13   1   1.0727  0.0494  0.3044  11.00000  0.05    0.15
Q14   1   1.1943  0.6289  0.9000  11.00000  0.05    0.15
Q15   1   0.0554 -0.0438  0.1960  11.00000  0.05    0.15
Q16   1   1.0560  0.3403  0.6203  11.00000  0.05    0.14
Q17   1   0.5991  0.3247  0.7606  11.00000  0.05    0.14
Q18   1   0.4449  0.1103  0.5759  11.00000  0.05    0.14
Q19   1   1.4003  0.2930  0.6961  11.00000  0.05    0.14
Q20   1   0.8287  0.6478  0.8651  11.00000  0.05    0.14
;
_shelx_res_checksum              58143
