Download citation
Download citation
link to html
The crystal structure of the metastable β form of 5-nitro-2,4-dihydro-3H-1,2,4-triazol-3-one (β-NTO, monoclinic, P21/c) has been investigated at five temperatures in the range 100–298 K using single-crystal X-ray diffraction techniques. The second-rank thermal expansion tensor has been determined to describe thermal behavior of the crystal. The most significant thermal expansion is in a plane, which is almost perpendicular to the planes of all the NTO molecules. Perpendicular to the plane of maximal thermal expansion, a modest thermal contraction takes place. Both thermal expansion and contraction of the crystal lattice indicate anharmonicity of the atomic thermal motion. The experimental thermal variation of the unit-cell parameters is in qualitative agreement with that previously obtained from molecular dynamics calculations. Rigid-body analysis of the molecular thermal motion was performed using the libration and translation second-rank tensors. Although the translation part of the thermal motion is not strongly anisotropic, the largest displacements of the NTO molecules are oriented in the plane of maximal thermal expansion of the crystal and have significant anharmonic components. The libration motion is more anisotropic, and the largest libration as well as the largest translation principal axes are directed along the C5—N5 bond in each NTO molecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S002188980300092X/do0018sup1.cif
Contains datablocks 100, 150, 200, 250, 298

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S002188980300092X/do0018100sup2.hkl
Contains datablock 100

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S002188980300092X/do0018150sup3.hkl
Contains datablock 150

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S002188980300092X/do0018200sup4.hkl
Contains datablock 200

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S002188980300092X/do0018250sup5.hkl
Contains datablock 250

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S002188980300092X/do0018298sup6.hkl
Contains datablock 298

CCDC references: 200142; 200143; 200144; 200145; 200146

Computing details top

For all compounds, data collection: Bruker SMART; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: Bruker SHELXTL; program(s) used to refine structure: Bruker SHELXTL; molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
(100) 5-nitro-2,4-dihydro-3H-1,2,4,-triazol-3-one top
Crystal data top
C2H2N4O3F(000) = 264
Mr = 130.08Dx = 1.926 Mg m3
Monoclinic, P21/cAg Kα radiation, λ = 0.56086 Å
a = 9.3129 (4) ÅCell parameters from 1406 reflections
b = 5.4458 (2) Åθ = 1.8–35.5°
c = 9.0261 (3) ŵ = 0.11 mm1
β = 101.464 (1)°T = 100 K
V = 448.64 (3) Å3Plate-like, colorless
Z = 40.24 × 0.08 × 0.02 mm
Data collection top
Bruker platform
diffractometer
1036 independent reflections
Radiation source: fine-focus sealed tube1036 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 35.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1813
Tmin = 0.919, Tmax = 1.000k = 107
2922 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093Calculated w = 1/[σ2(Fo2) + (0.0576P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
1036 reflectionsΔρmax = 0.56 e Å3
90 parametersΔρmin = 0.28 e Å3
0 restraints
Crystal data top
C2H2N4O3V = 448.64 (3) Å3
Mr = 130.08Z = 4
Monoclinic, P21/cAg Kα radiation, λ = 0.56086 Å
a = 9.3129 (4) ŵ = 0.11 mm1
b = 5.4458 (2) ÅT = 100 K
c = 9.0261 (3) Å0.24 × 0.08 × 0.02 mm
β = 101.464 (1)°
Data collection top
Bruker platform
diffractometer
1036 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1036 reflections with I > 2σ(I)
Tmin = 0.919, Tmax = 1.000Rint = 0.034
2922 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04190 parameters
wR(F2) = 0.0930 restraints
S = 1.10Δρmax = 0.56 e Å3
1036 reflectionsΔρmin = 0.28 e Å3
Special details top

Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N20.6539 (2)0.7348 (3)0.2358 (2)0.0110 (3)
H20.583 (3)0.636 (5)0.199 (3)0.027 (7)*
O30.86326 (15)0.5898 (2)0.1599 (2)0.0126 (3)
N10.6154 (2)0.9264 (3)0.3183 (2)0.0111 (3)
N40.8523 (2)0.9462 (3)0.3060 (2)0.0092 (3)
H40.946 (3)0.998 (5)0.318 (3)0.025 (7)*
C30.7983 (2)0.7401 (3)0.2253 (2)0.0096 (3)
O5B0.8698 (2)1.3632 (2)0.4765 (2)0.0161 (3)
O5A0.6410 (2)1.3248 (2)0.4979 (2)0.0181 (3)
N50.7507 (2)1.2608 (3)0.4511 (2)0.0115 (3)
C50.7380 (2)1.0440 (3)0.3573 (2)0.0095 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0077 (6)0.0097 (6)0.0154 (7)0.0006 (5)0.0018 (5)0.0029 (5)
O30.0103 (6)0.0133 (5)0.0144 (6)0.0023 (5)0.0029 (5)0.0031 (5)
N10.0098 (7)0.0101 (6)0.0134 (7)0.0016 (5)0.0026 (5)0.0007 (5)
N40.0060 (6)0.0103 (6)0.0114 (7)0.0006 (5)0.0019 (5)0.0013 (5)
C30.0078 (6)0.0109 (7)0.0098 (7)0.0010 (6)0.0005 (5)0.0006 (6)
O5B0.0155 (7)0.0139 (6)0.0187 (7)0.0056 (5)0.0032 (5)0.0020 (5)
O5A0.0153 (7)0.0198 (6)0.0199 (8)0.0042 (5)0.0051 (6)0.0061 (5)
N50.0122 (7)0.0107 (6)0.0113 (7)0.0010 (6)0.0021 (5)0.0005 (5)
C50.0100 (7)0.0088 (7)0.0097 (7)0.0002 (5)0.0022 (6)0.0002 (5)
Geometric parameters (Å, º) top
N2—C31.368 (2)N4—C31.377 (2)
N2—N11.370 (2)O5B—N51.222 (2)
O3—C31.235 (2)O5A—N51.230 (2)
N1—C51.295 (2)N5—C51.444 (2)
N4—C51.352 (2)
C3—N2—N1112.85 (14)O5B—N5—O5A126.2 (2)
C5—N1—N2102.31 (14)O5B—N5—C5116.65 (15)
C5—N4—C3105.83 (14)O5A—N5—C5117.11 (15)
O3—C3—N2126.9 (2)N1—C5—N4115.1 (2)
O3—C3—N4129.1 (2)N1—C5—N5121.9 (2)
N2—C3—N4103.96 (14)N4—C5—N5123.01 (15)
(150) 5-nitro-2,4-dihydro-3H-1,2,4,-triazol-3-one top
Crystal data top
C2H2N4O3F(000) = 264
Mr = 130.08Dx = 1.914 Mg m3
Monoclinic, P21/cAg Kα radiation, λ = 0.56086 Å
a = 9.3185 (4) ÅCell parameters from 1287 reflections
b = 5.4615 (2) Åθ = 1.8–33.4°
c = 9.0475 (3) ŵ = 0.10 mm1
β = 101.332 (1)°T = 150 K
V = 451.48 (3) Å3Plate-like, colorless
Z = 40.24 × 0.08 × 0.02 mm
Data collection top
Bruker platform
diffractometer
894 independent reflections
Radiation source: fine-focus sealed tube894 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω–scanθmax = 33.4°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1713
Tmin = 0.912, Tmax = 1.000k = 107
2578 measured reflectionsl = 1615
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092Calculated w = 1/[σ2(Fo2) + (0.0607P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
894 reflectionsΔρmax = 0.53 e Å3
90 parametersΔρmin = 0.24 e Å3
0 restraints
Crystal data top
C2H2N4O3V = 451.48 (3) Å3
Mr = 130.08Z = 4
Monoclinic, P21/cAg Kα radiation, λ = 0.56086 Å
a = 9.3185 (4) ŵ = 0.10 mm1
b = 5.4615 (2) ÅT = 150 K
c = 9.0475 (3) Å0.24 × 0.08 × 0.02 mm
β = 101.332 (1)°
Data collection top
Bruker platform
diffractometer
894 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
894 reflections with I > 2σ(I)
Tmin = 0.912, Tmax = 1.000Rint = 0.030
2578 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03990 parameters
wR(F2) = 0.0920 restraints
S = 1.08Δρmax = 0.53 e Å3
894 reflectionsΔρmin = 0.24 e Å3
Special details top

Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N20.6538 (2)0.7362 (3)0.2357 (2)0.0149 (3)
H20.585 (3)0.640 (5)0.198 (3)0.027 (7)*
O30.8630 (2)0.5905 (2)0.1601 (2)0.0176 (3)
N10.6155 (2)0.9272 (3)0.3179 (2)0.0147 (3)
N40.8522 (2)0.9456 (3)0.3060 (2)0.0124 (3)
H40.945 (4)0.995 (6)0.318 (4)0.046 (9)*
C30.7987 (2)0.7406 (3)0.2251 (2)0.0127 (3)
O5B0.8699 (2)1.3613 (3)0.4764 (2)0.0222 (3)
O5A0.6413 (2)1.3242 (3)0.4975 (2)0.0258 (4)
N50.7507 (2)1.2599 (3)0.4508 (2)0.0164 (3)
C50.7378 (2)1.0433 (3)0.3572 (2)0.0131 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0089 (7)0.0142 (7)0.0214 (8)0.0019 (6)0.0024 (6)0.0039 (6)
O30.0132 (7)0.0199 (7)0.0195 (7)0.0028 (5)0.0027 (6)0.0045 (6)
N10.0107 (7)0.0151 (7)0.0180 (8)0.0009 (6)0.0023 (6)0.0012 (6)
N40.0083 (7)0.0139 (7)0.0150 (8)0.0012 (6)0.0021 (6)0.0016 (6)
C30.0090 (7)0.0152 (8)0.0131 (8)0.0002 (7)0.0001 (6)0.0015 (7)
O5B0.0212 (8)0.0196 (7)0.0255 (8)0.0081 (6)0.0042 (7)0.0037 (6)
O5A0.0209 (8)0.0282 (8)0.0289 (10)0.0066 (6)0.0064 (7)0.0088 (6)
N50.0179 (8)0.0152 (7)0.0159 (8)0.0005 (7)0.0028 (7)0.0006 (6)
C50.0125 (8)0.0123 (8)0.0145 (9)0.0007 (6)0.0025 (7)0.0005 (6)
Geometric parameters (Å, º) top
N2—N11.369 (2)N4—C31.377 (2)
N2—C31.372 (2)O5B—N51.222 (2)
O3—C31.231 (2)O5A—N51.228 (2)
N1—C51.291 (2)N5—C51.447 (3)
N4—C51.353 (2)
N1—N2—C3112.9 (2)O5B—N5—O5A126.2 (2)
C5—N1—N2102.34 (15)O5B—N5—C5116.7 (2)
C5—N4—C3106.0 (2)O5A—N5—C5117.1 (2)
O3—C3—N2126.9 (2)N1—C5—N4115.1 (2)
O3—C3—N4129.5 (2)N1—C5—N5122.0 (2)
N2—C3—N4103.6 (2)N4—C5—N5122.9 (2)
(200) 5-nitro-2,4-dihydro-3H-1,2,4,-triazol-3-one top
Crystal data top
C2H2N4O3F(000) = 264
Mr = 130.08Dx = 1.901 Mg m3
Monoclinic, P21/cAg Kα radiation, λ = 0.56086 Å
a = 9.3220 (4) ÅCell parameters from 1193 reflections
b = 5.4791 (2) Åθ = 1.8–31.1°
c = 9.0685 (3) ŵ = 0.10 mm1
β = 101.182 (1)°T = 200 K
V = 454.39 (3) Å3Plate-like, colorless
Z = 40.24 × 0.08 × 0.02 mm
Data collection top
Bruker platform
diffractometer
758 independent reflections
Radiation source: fine-focus sealed tube757 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω–scanθmax = 31.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1713
Tmin = 0.806, Tmax = 1.000k = 107
2264 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091Calculated w = 1/[σ2(Fo2) + (0.0611P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.033
758 reflectionsΔρmax = 0.40 e Å3
90 parametersΔρmin = 0.25 e Å3
0 restraints
Crystal data top
C2H2N4O3V = 454.39 (3) Å3
Mr = 130.08Z = 4
Monoclinic, P21/cAg Kα radiation, λ = 0.56086 Å
a = 9.3220 (4) ŵ = 0.10 mm1
b = 5.4791 (2) ÅT = 200 K
c = 9.0685 (3) Å0.24 × 0.08 × 0.02 mm
β = 101.182 (1)°
Data collection top
Bruker platform
diffractometer
758 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
757 reflections with I > 2σ(I)
Tmin = 0.806, Tmax = 1.000Rint = 0.029
2264 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03790 parameters
wR(F2) = 0.0910 restraints
S = 1.09Δρmax = 0.40 e Å3
758 reflectionsΔρmin = 0.25 e Å3
Special details top

Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N20.6540 (2)0.7379 (3)0.2356 (2)0.0191 (4)
H20.582 (4)0.645 (6)0.199 (4)0.044 (9)*
O30.8629 (2)0.5915 (3)0.1605 (2)0.0229 (4)
N10.6157 (2)0.9281 (3)0.3179 (2)0.0198 (4)
N40.8522 (2)0.9453 (3)0.3059 (2)0.0163 (4)
H40.945 (4)0.996 (6)0.319 (4)0.046 (9)*
C30.7985 (2)0.7417 (4)0.2251 (2)0.0167 (4)
O5B0.8701 (2)1.3592 (3)0.4764 (2)0.0292 (4)
O5A0.6416 (2)1.3237 (3)0.4967 (2)0.0340 (5)
N50.7510 (2)1.2590 (4)0.4503 (2)0.0211 (4)
C50.7380 (2)1.0430 (4)0.3573 (3)0.0163 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0117 (8)0.0179 (8)0.0277 (10)0.0014 (7)0.0036 (7)0.0045 (8)
O30.0168 (8)0.0254 (8)0.0263 (9)0.0037 (6)0.0039 (7)0.0061 (7)
N10.0156 (9)0.0193 (8)0.0246 (10)0.0023 (7)0.0041 (8)0.0007 (7)
N40.0120 (8)0.0180 (8)0.0190 (9)0.0015 (7)0.0035 (7)0.0016 (7)
C30.0134 (8)0.0182 (9)0.0181 (10)0.0003 (8)0.0021 (7)0.0022 (8)
O5B0.0297 (10)0.0264 (8)0.0321 (10)0.0111 (7)0.0070 (8)0.0054 (7)
O5A0.0282 (10)0.0358 (10)0.0390 (12)0.0089 (8)0.0088 (9)0.0127 (8)
N50.0245 (10)0.0192 (8)0.0196 (10)0.0010 (8)0.0045 (8)0.0010 (8)
C50.0143 (9)0.0171 (9)0.0181 (10)0.0005 (7)0.0042 (8)0.0017 (8)
Geometric parameters (Å, º) top
N2—C31.368 (3)N4—C31.375 (3)
N2—N11.369 (3)O5B—N51.220 (2)
O3—C31.232 (3)O5A—N51.228 (2)
N1—C51.291 (3)N5—C51.445 (3)
N4—C51.353 (3)
C3—N2—N1113.0 (2)O5B—N5—O5A126.1 (2)
C5—N1—N2102.2 (2)O5B—N5—C5116.9 (2)
C5—N4—C3105.9 (2)O5A—N5—C5117.1 (2)
O3—C3—N2126.9 (2)N1—C5—N4115.1 (2)
O3—C3—N4129.4 (2)N1—C5—N5122.0 (2)
N2—C3—N4103.7 (2)N4—C5—N5122.9 (2)
(250) 5-nitro-2,4-dihydro-3H-1,2,4,-triazol-3-one top
Crystal data top
C2H2N4O3F(000) = 264
Mr = 130.08Dx = 1.889 Mg m3
Monoclinic, P21/cAg Kα radiation, λ = 0.56086 Å
a = 9.3233 (4) ÅCell parameters from 1204 reflections
b = 5.4977 (2) Åθ = 1.8–30.7°
c = 9.0885 (3) ŵ = 0.10 mm1
β = 101.019 (1)°T = 250 K
V = 457.26 (3) Å3Plate-like, colorless
Z = 40.24 × 0.08 × 0.02 mm
Data collection top
Radiation source: fine-focus sealed tube656 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
θmax = 30.7°, θmin = 1.8°
Tmin = 0.839, Tmax = 1.000h = 1512
2007 measured reflectionsk = 87
657 independent reflectionsl = 1214
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090Calculated w = 1/[σ2(Fo2) + (0.0649P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.025
657 reflectionsΔρmax = 0.34 e Å3
90 parametersΔρmin = 0.21 e Å3
0 restraints
Crystal data top
C2H2N4O3V = 457.26 (3) Å3
Mr = 130.08Z = 4
Monoclinic, P21/cAg Kα radiation, λ = 0.56086 Å
a = 9.3233 (4) ŵ = 0.10 mm1
b = 5.4977 (2) ÅT = 250 K
c = 9.0885 (3) Å0.24 × 0.08 × 0.02 mm
β = 101.019 (1)°
Data collection top
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
657 independent reflections
Tmin = 0.839, Tmax = 1.000656 reflections with I > 2σ(I)
2007 measured reflectionsRint = 0.031
Refinement top
R[F2 > 2σ(F2)] = 0.03690 parameters
wR(F2) = 0.0900 restraints
S = 1.06Δρmax = 0.34 e Å3
657 reflectionsΔρmin = 0.21 e Å3
Special details top

Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N20.6541 (2)0.7397 (4)0.2353 (3)0.0246 (5)
H20.584 (4)0.647 (6)0.201 (4)0.043 (9)*
O30.8626 (2)0.5925 (3)0.1607 (2)0.0285 (4)
N10.6159 (2)0.9300 (3)0.3175 (2)0.0237 (4)
N40.8523 (2)0.9446 (3)0.3061 (2)0.0204 (4)
H40.943 (3)0.996 (6)0.317 (4)0.037 (8)*
C30.7985 (3)0.7421 (4)0.2252 (3)0.0200 (4)
O5B0.8706 (2)1.3569 (3)0.4763 (2)0.0372 (5)
O5A0.6421 (2)1.3235 (4)0.4960 (3)0.0436 (6)
N50.7511 (2)1.2584 (4)0.4498 (2)0.0263 (5)
C50.7385 (2)1.0434 (4)0.3570 (3)0.0202 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0142 (9)0.0228 (10)0.0363 (13)0.0018 (8)0.0038 (9)0.0052 (9)
O30.0191 (9)0.0319 (9)0.0335 (10)0.0040 (7)0.0028 (8)0.0082 (8)
N10.0164 (10)0.0251 (10)0.0291 (12)0.0030 (8)0.0036 (9)0.0010 (9)
N40.0143 (9)0.0212 (10)0.0256 (12)0.0024 (8)0.0037 (8)0.0015 (8)
C30.0148 (10)0.0211 (10)0.0231 (11)0.0002 (9)0.0011 (8)0.0037 (10)
O5B0.0364 (12)0.0324 (10)0.0429 (12)0.0131 (8)0.0078 (10)0.0064 (9)
O5A0.0351 (12)0.0460 (12)0.0507 (15)0.0101 (9)0.0107 (11)0.0168 (10)
N50.0307 (12)0.0235 (10)0.0246 (11)0.0007 (10)0.0047 (9)0.0006 (9)
C50.0185 (11)0.0194 (11)0.0227 (12)0.0008 (8)0.0042 (9)0.0021 (9)
Geometric parameters (Å, º) top
N2—C31.367 (3)N4—C31.375 (3)
N2—N11.371 (3)O5B—N51.221 (3)
O3—C31.229 (3)O5A—N51.225 (3)
N1—C51.291 (3)N5—C51.444 (3)
N4—C51.350 (3)
C3—N2—N1113.0 (2)O5B—N5—O5A126.1 (2)
C5—N1—N2102.2 (2)O5B—N5—C5116.6 (2)
C5—N4—C3106.2 (2)O5A—N5—C5117.3 (2)
O3—C3—N2126.9 (2)N1—C5—N4115.0 (2)
O3—C3—N4129.5 (2)N1—C5—N5121.8 (2)
N2—C3—N4103.6 (2)N4—C5—N5123.2 (2)
(298) 5-nitro-2,4-dihydro-3H-1,2,4,-triazol-3-one top
Crystal data top
C2H2N4O3F(000) = 264
Mr = 130.08Dx = 1.876 Mg m3
Monoclinic, P21/cAg Kα radiation, λ = 0.56086 Å
a = 9.3207 (4) ÅCell parameters from 165 reflections
b = 5.5215 (2) Åθ = 1.8–28.3°
c = 9.1102 (3) ŵ = 0.10 mm1
β = 100.870 (1)°T = 298 K
V = 460.44 (3) Å3Plate-like, colorless
Z = 40.24 × 0.08 × 0.02 mm
Data collection top
Bruker Platform
diffractometer
578 independent reflections
Radiation source: fine-focus sealed tube578 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
ω–scanθmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 159
Tmin = 0.560, Tmax = 1.000k = 87
1691 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108Calculated w = 1/[σ2(Fo2) + (0.0767P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.002
578 reflectionsΔρmax = 0.35 e Å3
90 parametersΔρmin = 0.27 e Å3
0 restraints
Crystal data top
C2H2N4O3V = 460.44 (3) Å3
Mr = 130.08Z = 4
Monoclinic, P21/cAg Kα radiation, λ = 0.56086 Å
a = 9.3207 (4) ŵ = 0.10 mm1
b = 5.5215 (2) ÅT = 298 K
c = 9.1102 (3) Å0.24 × 0.08 × 0.02 mm
β = 100.870 (1)°
Data collection top
Bruker Platform
diffractometer
578 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
578 reflections with I > 2σ(I)
Tmin = 0.560, Tmax = 1.000Rint = 0.050
1691 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04490 parameters
wR(F2) = 0.1080 restraints
S = 1.11Δρmax = 0.35 e Å3
578 reflectionsΔρmin = 0.27 e Å3
Special details top

Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N20.6540 (3)0.7414 (6)0.2357 (3)0.0301 (7)
H20.586 (4)0.641 (7)0.201 (4)0.037 (10)*
O30.8626 (2)0.5938 (4)0.1612 (2)0.0334 (6)
N10.6163 (2)0.9308 (5)0.3172 (3)0.0278 (6)
N40.8523 (3)0.9441 (5)0.3060 (3)0.0240 (6)
H40.940 (4)0.990 (8)0.316 (4)0.044 (11)*
C30.7986 (3)0.7430 (7)0.2253 (3)0.0262 (7)
O5B0.8705 (3)1.3544 (5)0.4762 (3)0.0442 (7)
O5A0.6424 (3)1.3238 (6)0.4944 (3)0.0528 (9)
N50.7519 (3)1.2566 (6)0.4496 (3)0.0318 (7)
C50.7385 (3)1.0437 (6)0.3568 (3)0.0240 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0187 (11)0.031 (2)0.0399 (15)0.0029 (13)0.0040 (10)0.0060 (15)
O30.0236 (10)0.039 (2)0.0363 (12)0.0065 (10)0.0028 (9)0.0095 (11)
N10.0239 (13)0.025 (2)0.0349 (15)0.0036 (11)0.0059 (11)0.0004 (13)
N40.0171 (11)0.025 (2)0.0294 (14)0.0038 (11)0.0027 (10)0.0020 (12)
C30.0178 (11)0.035 (2)0.0248 (14)0.0019 (15)0.0009 (10)0.0057 (15)
O5B0.0472 (15)0.039 (2)0.047 (2)0.0164 (13)0.0095 (11)0.0089 (13)
O5A0.0436 (14)0.060 (2)0.056 (2)0.0145 (13)0.0104 (12)0.0222 (14)
N50.0374 (14)0.028 (2)0.0287 (14)0.0016 (14)0.0037 (11)0.0006 (14)
C50.0241 (13)0.023 (2)0.0241 (13)0.0001 (12)0.0029 (10)0.0005 (14)
Geometric parameters (Å, º) top
N2—N11.366 (4)N4—C31.373 (4)
N2—C31.369 (4)O5B—N51.212 (3)
O3—C31.228 (4)O5A—N51.226 (3)
N1—C51.290 (4)N5—C51.440 (4)
N4—C51.352 (4)
N1—N2—C3113.0 (3)O5B—N5—O5A125.7 (3)
C5—N1—N2102.6 (2)O5B—N5—C5117.1 (3)
C5—N4—C3106.4 (2)O5A—N5—C5117.2 (3)
O3—C3—N2127.0 (3)N1—C5—N4114.6 (3)
O3—C3—N4129.5 (3)N1—C5—N5122.2 (3)
N2—C3—N4103.5 (3)N4—C5—N5123.1 (2)

Experimental details

(100)(150)(200)(250)
Crystal data
Chemical formulaC2H2N4O3C2H2N4O3C2H2N4O3C2H2N4O3
Mr130.08130.08130.08130.08
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)100150200250
a, b, c (Å)9.3129 (4), 5.4458 (2), 9.0261 (3)9.3185 (4), 5.4615 (2), 9.0475 (3)9.3220 (4), 5.4791 (2), 9.0685 (3)9.3233 (4), 5.4977 (2), 9.0885 (3)
β (°) 101.464 (1) 101.332 (1) 101.182 (1) 101.019 (1)
V3)448.64 (3)451.48 (3)454.39 (3)457.26 (3)
Z4444
Radiation typeAg Kα, λ = 0.56086 ÅAg Kα, λ = 0.56086 ÅAg Kα, λ = 0.56086 ÅAg Kα, λ = 0.56086 Å
µ (mm1)0.110.100.100.10
Crystal size (mm)0.24 × 0.08 × 0.020.24 × 0.08 × 0.020.24 × 0.08 × 0.020.24 × 0.08 × 0.02
Data collection
DiffractometerBruker platform
diffractometer
Bruker platform
diffractometer
Bruker platform
diffractometer
?
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Multi-scan
(SADABS; Sheldrick, 1996)
Multi-scan
(SADABS; Sheldrick, 1996)
Multi-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.919, 1.0000.912, 1.0000.806, 1.0000.839, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
2922, 1036, 1036 2578, 894, 894 2264, 758, 757 2007, 657, 656
Rint0.0340.0300.0290.031
(sin θ/λ)max1)1.0360.9820.9210.909
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.093, 1.10 0.039, 0.092, 1.08 0.037, 0.091, 1.09 0.036, 0.090, 1.06
No. of reflections1036894758657
No. of parameters90909090
Δρmax, Δρmin (e Å3)0.56, 0.280.53, 0.240.40, 0.250.34, 0.21


(298)
Crystal data
Chemical formulaC2H2N4O3
Mr130.08
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)9.3207 (4), 5.5215 (2), 9.1102 (3)
β (°) 100.870 (1)
V3)460.44 (3)
Z4
Radiation typeAg Kα, λ = 0.56086 Å
µ (mm1)0.10
Crystal size (mm)0.24 × 0.08 × 0.02
Data collection
DiffractometerBruker Platform
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.560, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
1691, 578, 578
Rint0.050
(sin θ/λ)max1)0.844
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.108, 1.11
No. of reflections578
No. of parameters90
Δρmax, Δρmin (e Å3)0.35, 0.27

Computer programs: Bruker SMART, Bruker SAINT, Bruker SHELXTL.

 

Follow J. Appl. Cryst.
Sign up for e-alerts
Follow J. Appl. Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds