Low-temperature phase transition and high-pressure phase stability of 1H-pyrazole-1-carboxamidine nitrate

The phase transition observed in a temperature-dependent experiment at 174 K is unachievable under high-pressure conditions. Negative thermal expansion for phase (II) and negative compressibility for phase (I) were observed. A new salt of 1H-pyrazole-1-carboxamidine, (HPyCA)NO₃, for guanylation reaction was obtained in a crystalline form. The compound crystallizes in monoclinic space group P2₁/c and a phase transition at 174 K to triclinic modification P1 was found. An unusual increase of the unit-cell volume was observed just after transition. Although the volume decreases upon cooling, it remains higher down to 160 K in comparison to the unit-cell volume of phase (I). The mechanism of the phase transition is connected with a minor movement of the nitrate anions. The triclinic phase was unreachable at room-temperature high-pressure conditions up to 1.27 GPa. On further compression, delamination of the crystal was observed. Phase (I) exhibits negative linear compressibility, whereas abnormal behaviour of the b unit-cell parameter upon cooling was observed, indicating negative thermal linear expansion. The unusual nature of the compound is associated with the two-dimensional hydrogen-bonding network, which is less susceptible to deformation than stacking interactions connecting the layers of hydrogen bonds. Infrared spectroscopy and differential scanning calorimetry measurements were used to investigate the changes of intermolecular interactions during the phase transition.

Computing details

For all structures, data collection: CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018); cell refinement: CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018); data reduction: CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018). Program(s) used to solve structure: SHELXS (Sheldrick, 2008) for 0.12GPa, 0.13GPa, 0.19GPa, 0.28GPa, 0.32GPa, 0.39GPa, 0.44GPa, 0.46GPa, 0.52GPa, 0.67GPa, 0.89GPa, 1.11GPa, 1.15GPa, 1.27GPa; ShelXT (Sheldrick, 2015) for 0.58GPa, 100K, 300K. For all structures, program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(0.12GPa)

Crystal data

C4H7N4·NO3	F(000) = 360
Mr = 173.15	Dx = 1.582 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.1374 (19) Å	Cell parameters from 438 reflections
b = 10.305 (10) Å	θ = 3.5–19.9°
c = 13.935 (5) Å	µ = 0.14 mm^−1
β = 99.71 (3)°	T = 293 K
V = 727.2 (8) Å^3	Prism, colourless
Z = 4

Data collection

Xcalibur, Sapphire2, large Be window diffractometer	533 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	297 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
Detector resolution: 8.2214 pixels mm^-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −5→5
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −7→7
Tmin = 0.205, Tmax = 1.000	l = −16→16
3916 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.151	w = 1/[σ^2(Fo^2) + (0.042P)^2 + 1.1814P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
533 reflections	Δρmax = 0.15 e Å^−3
109 parameters	Δρmin = −0.17 e Å^−3
54 restraints

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1107 (16)	0.7847 (14)	0.5402 (7)	0.070 (4)
H1	−0.041811	0.824034	0.507598	0.084*
C2	0.3306 (14)	0.8552 (12)	0.5874 (5)	0.069 (3)
H2	0.353075	0.944744	0.589048	0.082*
C3	0.4970 (17)	0.7666 (14)	0.6284 (5)	0.066 (3)
H3	0.662304	0.782080	0.665402	0.079*
C4	0.4752 (17)	0.5217 (14)	0.6284 (5)	0.059 (3)
N1	0.3825 (13)	0.6464 (11)	0.6068 (4)	0.057 (3)
N2	0.1403 (10)	0.6610 (11)	0.5465 (5)	0.064 (4)
N3	0.3391 (12)	0.4213 (10)	0.5917 (4)	0.076 (3)
H3A	0.399302	0.344280	0.604577	0.091*
H3B	0.189102	0.432186	0.554556	0.091*
N4	0.7069 (10)	0.5069 (8)	0.6858 (4)	0.070 (4)
H4A	0.769222	0.430297	0.699245	0.084*
H4B	0.794883	0.573809	0.709605	0.084*
N5	0.2477 (19)	0.6494 (19)	0.8251 (6)	0.066 (6)
O1	0.4839 (9)	0.6741 (7)	0.8580 (3)	0.075 (3)
O2	0.1697 (19)	0.5353 (15)	0.8211 (6)	0.107 (6)
O3	0.0898 (11)	0.7371 (10)	0.7940 (4)	0.085 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.057 (5)	0.061 (13)	0.086 (6)	0.009 (5)	0.000 (4)	−0.015 (8)
C2	0.065 (6)	0.066 (12)	0.073 (5)	−0.008 (4)	0.004 (4)	0.005 (6)
C3	0.058 (5)	0.069 (11)	0.066 (5)	−0.013 (4)	−0.001 (4)	0.001 (6)
C4	0.043 (4)	0.070 (11)	0.065 (5)	0.005 (4)	0.011 (3)	−0.001 (6)
N1	0.035 (4)	0.065 (10)	0.069 (4)	−0.004 (3)	0.004 (3)	−0.007 (5)
N2	0.045 (4)	0.065 (13)	0.074 (4)	0.003 (4)	−0.008 (3)	−0.013 (6)
N3	0.057 (5)	0.070 (11)	0.091 (4)	0.006 (4)	−0.017 (3)	−0.004 (5)
N4	0.057 (4)	0.065 (14)	0.080 (4)	0.000 (3)	−0.013 (3)	−0.014 (4)
N5	0.056 (7)	0.07 (2)	0.070 (4)	−0.002 (5)	0.001 (4)	−0.003 (6)
O1	0.048 (4)	0.071 (12)	0.099 (4)	−0.008 (3)	−0.007 (3)	−0.004 (4)
O2	0.078 (6)	0.08 (2)	0.152 (6)	−0.014 (6)	−0.022 (4)	−0.010 (7)
O3	0.054 (4)	0.103 (15)	0.094 (4)	0.010 (4)	−0.002 (3)	0.018 (5)

Geometric parameters (Å, º)

C1—C2	1.409 (14)	C4—N4	1.326 (9)
C1—N2	1.285 (14)	N1—N2	1.387 (9)
C2—C3	1.313 (15)	N5—O1	1.249 (9)
C3—N1	1.382 (16)	N5—O2	1.24 (2)
C4—N1	1.386 (16)	N5—O3	1.243 (19)
C4—N3	1.304 (14)
N2—C1—C2	113.8 (8)	C3—N1—N2	109.9 (11)
C3—C2—C1	104.9 (12)	C4—N1—N2	118.1 (11)
C2—C3—N1	107.8 (9)	C1—N2—N1	103.4 (9)
N3—C4—N1	120.6 (9)	O2—N5—O1	119.8 (19)
N3—C4—N4	120.9 (12)	O2—N5—O3	119.1 (11)
N4—C4—N1	118.6 (12)	O3—N5—O1	121.1 (17)
C3—N1—C4	131.8 (10)

(0.13GPa)

Crystal data

C4H7N4·NO3	F(000) = 360
Mr = 173.15	Dx = 1.583 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.1439 (9) Å	Cell parameters from 1185 reflections
b = 10.2415 (9) Å	θ = 4.0–21.9°
c = 14.008 (9) Å	µ = 0.14 mm^−1
β = 100.11 (4)°	T = 293 K
V = 726.5 (5) Å^3	Prism, colourless
Z = 4

Data collection

Xcalibur, Sapphire2, large Be window diffractometer	457 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	330 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 8.2214 pixels mm^-1	θmax = 25.1°, θmin = 4.0°
ω scans	h = −5→5
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −12→12
Tmin = 0.222, Tmax = 1.000	l = −8→9
3998 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0253P)^2 + 0.797P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.107	(Δ/σ)max < 0.001
S = 1.14	Δρmax = 0.10 e Å^−3
457 reflections	Δρmin = −0.13 e Å^−3
110 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.024 (7)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1111 (14)	0.7877 (5)	0.5380 (8)	0.059 (9)
H1	−0.035497	0.827309	0.500879	0.071*
C2	0.3256 (15)	0.8563 (5)	0.5892 (9)	0.069 (9)
H2	0.346847	0.946475	0.592781	0.083*
C3	0.4951 (15)	0.7654 (4)	0.6322 (9)	0.067 (9)
H3	0.656829	0.780155	0.672248	0.080*
C4	0.4781 (15)	0.5226 (4)	0.6294 (9)	0.037 (9)
N1	0.3828 (11)	0.6469 (3)	0.6056 (7)	0.040 (8)
N2	0.1402 (10)	0.6607 (3)	0.5482 (7)	0.062 (7)
N3	0.3397 (11)	0.4238 (4)	0.5910 (7)	0.071 (8)
H3A	0.398422	0.345675	0.602186	0.085*
H3B	0.189376	0.436508	0.554266	0.085*
N4	0.7073 (11)	0.5080 (4)	0.6856 (7)	0.069 (7)
H4A	0.771111	0.431093	0.698110	0.083*
H4B	0.794373	0.575385	0.709991	0.083*
N5	0.2467 (12)	0.6486 (4)	0.8249 (8)	0.077 (9)
O1	0.4850 (9)	0.6735 (3)	0.8574 (6)	0.060 (6)
O2	0.1682 (10)	0.5354 (3)	0.8225 (7)	0.107 (8)
O3	0.0896 (9)	0.7382 (3)	0.7936 (6)	0.065 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.058 (6)	0.051 (4)	0.06 (2)	−0.003 (3)	0.000 (11)	0.002 (4)
C2	0.076 (7)	0.043 (3)	0.08 (2)	−0.009 (3)	0.001 (11)	0.003 (4)
C3	0.060 (6)	0.047 (3)	0.08 (2)	−0.010 (3)	−0.006 (10)	−0.016 (4)
C4	0.036 (6)	0.048 (3)	0.03 (2)	−0.001 (3)	0.020 (11)	−0.001 (4)
N1	0.033 (5)	0.046 (3)	0.04 (2)	0.000 (2)	0.011 (10)	−0.001 (3)
N2	0.045 (4)	0.045 (3)	0.089 (16)	0.001 (2)	−0.011 (8)	−0.002 (3)
N3	0.063 (6)	0.042 (3)	0.093 (17)	0.002 (2)	−0.027 (9)	−0.002 (3)
N4	0.055 (5)	0.065 (3)	0.073 (17)	0.000 (2)	−0.026 (9)	0.003 (4)
N5	0.063 (6)	0.058 (3)	0.10 (2)	−0.001 (3)	−0.027 (10)	0.001 (4)
O1	0.041 (4)	0.058 (2)	0.077 (15)	−0.0050 (18)	0.000 (7)	−0.009 (3)
O2	0.071 (5)	0.055 (3)	0.176 (18)	−0.020 (2)	−0.033 (9)	−0.001 (3)
O3	0.046 (5)	0.071 (3)	0.076 (16)	0.008 (2)	0.003 (8)	0.013 (3)

Geometric parameters (Å, º)

C1—C2	1.396 (7)	C4—N4	1.306 (6)
C1—N2	1.315 (6)	N1—N2	1.368 (5)
C2—C3	1.344 (7)	N5—O1	1.256 (6)
C3—N1	1.367 (6)	N5—O2	1.227 (5)
C4—N1	1.384 (6)	N5—O3	1.250 (5)
C4—N3	1.299 (6)
N2—C1—C2	112.2 (5)	C3—N1—N2	111.6 (4)
C3—C2—C1	105.9 (4)	N2—N1—C4	119.0 (4)
C2—C3—N1	106.4 (4)	C1—N2—N1	103.9 (4)
N3—C4—N1	118.1 (4)	O2—N5—O1	119.8 (4)
N3—C4—N4	122.1 (4)	O2—N5—O3	119.7 (5)
N4—C4—N1	119.7 (4)	O3—N5—O1	120.5 (4)
C3—N1—C4	129.5 (4)

(0.19GPa)

Crystal data

C4H7N4·NO3	F(000) = 360
Mr = 173.15	Dx = 1.597 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.1216 (12) Å	Cell parameters from 1212 reflections
b = 10.2236 (11) Å	θ = 4.0–22.2°
c = 13.952 (10) Å	µ = 0.14 mm^−1
β = 99.70 (5)°	T = 293 K
V = 720.1 (6) Å^3	Prism, colourless
Z = 4

Data collection

Xcalibur, Sapphire2, large Be window diffractometer	445 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	305 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
Detector resolution: 8.2214 pixels mm^-1	θmax = 25.1°, θmin = 4.0°
ω scans	h = −5→5
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −12→12
Tmin = 0.353, Tmax = 1.000	l = −9→9
3976 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.062	H-atom parameters constrained
wR(F^2) = 0.184	w = 1/[σ^2(Fo^2) + (0.1077P)^2 + 0.7671P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
445 reflections	Δρmax = 0.15 e Å^−3
109 parameters	Δρmin = −0.20 e Å^−3
0 restraints

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1087 (19)	0.7885 (6)	0.5374 (11)	0.077 (11)
H1	−0.037038	0.827790	0.499529	0.092*
C2	0.324 (2)	0.8571 (6)	0.5900 (13)	0.069 (12)
H2	0.344263	0.947403	0.595041	0.082*
C3	0.495 (2)	0.7666 (5)	0.6313 (12)	0.073 (11)
H3	0.658372	0.781270	0.670149	0.088*
C4	0.477 (2)	0.5229 (5)	0.6302 (12)	0.058 (12)
N1	0.3806 (16)	0.6468 (4)	0.6050 (9)	0.045 (10)
N2	0.1399 (15)	0.6614 (4)	0.5488 (9)	0.077 (9)
N3	0.3389 (15)	0.4240 (5)	0.5916 (9)	0.070 (8)
H3A	0.400260	0.345943	0.601061	0.084*
H3B	0.185994	0.436582	0.556557	0.084*
N4	0.7079 (16)	0.5087 (5)	0.6834 (10)	0.076 (9)
H4A	0.774525	0.431836	0.694183	0.092*
H4B	0.794732	0.576175	0.708014	0.092*
N5	0.2461 (17)	0.6480 (5)	0.8264 (10)	0.072 (11)
O1	0.4846 (12)	0.6734 (4)	0.8569 (8)	0.088 (8)
O2	0.1671 (13)	0.5350 (4)	0.8237 (8)	0.091 (10)
O3	0.0884 (14)	0.7378 (4)	0.7939 (9)	0.085 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.057 (9)	0.047 (4)	0.12 (2)	−0.001 (3)	−0.010 (14)	0.001 (5)
C2	0.055 (10)	0.046 (4)	0.10 (3)	−0.002 (3)	0.012 (15)	−0.011 (5)
C3	0.055 (9)	0.049 (4)	0.11 (2)	−0.011 (3)	−0.016 (14)	−0.013 (5)
C4	0.041 (9)	0.047 (4)	0.08 (3)	−0.003 (3)	−0.002 (15)	0.003 (5)
N1	0.033 (7)	0.047 (3)	0.05 (2)	−0.002 (2)	0.005 (12)	0.002 (4)
N2	0.047 (7)	0.042 (3)	0.13 (2)	0.001 (2)	−0.020 (11)	0.001 (4)
N3	0.051 (7)	0.043 (3)	0.104 (18)	0.000 (3)	−0.020 (10)	0.006 (4)
N4	0.046 (8)	0.063 (4)	0.11 (2)	0.005 (3)	−0.020 (12)	−0.003 (4)
N5	0.054 (8)	0.053 (4)	0.10 (2)	0.000 (3)	−0.014 (13)	0.000 (4)
O1	0.045 (5)	0.050 (3)	0.152 (17)	−0.003 (2)	−0.029 (9)	−0.007 (4)
O2	0.064 (8)	0.056 (3)	0.14 (2)	−0.015 (3)	−0.021 (13)	−0.003 (4)
O3	0.059 (7)	0.066 (3)	0.12 (2)	0.005 (3)	−0.017 (12)	0.009 (4)

Geometric parameters (Å, º)

C1—C2	1.407 (10)	C4—N4	1.294 (7)
C1—N2	1.315 (8)	N1—N2	1.353 (7)
C2—C3	1.335 (9)	N5—O1	1.251 (8)
C3—N1	1.379 (7)	N5—O2	1.222 (6)
C4—N1	1.383 (8)	N5—O3	1.256 (6)
C4—N3	1.298 (8)
N2—C1—C2	111.2 (6)	N2—N1—C3	111.1 (4)
C3—C2—C1	106.1 (5)	N2—N1—C4	120.0 (5)
C2—C3—N1	106.5 (6)	C1—N2—N1	105.0 (4)
N3—C4—N1	117.5 (6)	O1—N5—O3	120.1 (6)
N4—C4—N1	120.1 (5)	O2—N5—O1	120.4 (5)
N4—C4—N3	122.1 (6)	O2—N5—O3	119.4 (6)
C3—N1—C4	128.9 (5)

(0.28GPa)

Crystal data

C4H7N4·NO3	F(000) = 360
Mr = 173.15	Dx = 1.609 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.0993 (14) Å	Cell parameters from 457 reflections
b = 10.252 (8) Å	θ = 3.0–19.3°
c = 13.845 (3) Å	µ = 0.14 mm^−1
β = 99.11 (2)°	T = 293 K
V = 714.6 (6) Å^3	Prism, colourless
Z = 4

Data collection

Xcalibur, Sapphire2, large Be window diffractometer	516 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	309 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 8.2214 pixels mm^-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −5→5
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −6→6
Tmin = 0.361, Tmax = 1.000	l = −16→16
3803 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.165	w = 1/[σ^2(Fo^2) + (0.081P)^2 + 0.4842P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
516 reflections	Δρmax = 0.14 e Å^−3
109 parameters	Δρmin = −0.12 e Å^−3
6 restraints

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1087 (15)	0.7869 (13)	0.5390 (6)	0.062 (4)
H1	−0.042950	0.825867	0.504837	0.075*
C2	0.3269 (15)	0.8590 (13)	0.5867 (5)	0.060 (5)
H2	0.348969	0.949081	0.588558	0.072*
C3	0.4921 (18)	0.7693 (16)	0.6281 (5)	0.057 (5)
H3	0.656783	0.785196	0.665791	0.068*
C4	0.4750 (17)	0.5203 (16)	0.6289 (5)	0.052 (6)
N1	0.3814 (14)	0.6471 (13)	0.6066 (4)	0.048 (5)
N2	0.1382 (10)	0.6618 (11)	0.5469 (5)	0.055 (4)
N3	0.3363 (12)	0.4238 (10)	0.5915 (4)	0.067 (4)
H3A	0.393695	0.345506	0.602543	0.080*
H3B	0.185523	0.437189	0.555258	0.080*
N4	0.7064 (9)	0.5081 (8)	0.6849 (3)	0.060 (3)
H4A	0.772735	0.431844	0.698181	0.072*
H4B	0.791860	0.576327	0.708286	0.072*
N5	0.2509 (16)	0.6445 (18)	0.8249 (5)	0.069 (5)
O1	0.4835 (8)	0.6735 (6)	0.8579 (3)	0.065 (3)
O2	0.1637 (18)	0.5365 (15)	0.8242 (5)	0.110 (6)
O3	0.0884 (10)	0.7363 (9)	0.7935 (3)	0.073 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.051 (4)	0.061 (11)	0.072 (4)	0.016 (5)	−0.001 (3)	−0.003 (6)
C2	0.061 (7)	0.05 (2)	0.064 (4)	−0.001 (5)	0.006 (4)	0.003 (6)
C3	0.049 (6)	0.06 (2)	0.060 (4)	−0.012 (5)	0.003 (4)	0.001 (6)
C4	0.037 (6)	0.07 (2)	0.054 (4)	0.002 (5)	0.009 (4)	0.007 (6)
N1	0.033 (5)	0.05 (2)	0.063 (3)	−0.010 (4)	0.006 (3)	−0.011 (6)
N2	0.042 (4)	0.048 (15)	0.069 (4)	0.005 (4)	−0.009 (3)	−0.002 (6)
N3	0.049 (5)	0.063 (16)	0.081 (4)	0.001 (4)	−0.014 (3)	−0.002 (5)
N4	0.051 (4)	0.048 (12)	0.074 (3)	0.000 (3)	−0.014 (3)	−0.006 (4)
N5	0.038 (6)	0.10 (2)	0.062 (4)	0.003 (5)	0.002 (3)	0.002 (5)
O1	0.041 (3)	0.056 (11)	0.093 (3)	−0.008 (2)	−0.008 (2)	−0.007 (3)
O2	0.064 (5)	0.12 (2)	0.133 (6)	−0.025 (6)	−0.019 (3)	0.007 (7)
O3	0.047 (4)	0.086 (13)	0.083 (3)	0.005 (3)	0.001 (2)	0.011 (4)

Geometric parameters (Å, º)

C1—C2	1.410 (16)	C4—N4	1.311 (9)
C1—N2	1.295 (13)	N1—N2	1.385 (10)
C2—C3	1.316 (18)	N5—O1	1.238 (8)
C3—N1	1.386 (18)	N5—O2	1.19 (2)
C4—N1	1.403 (17)	N5—O3	1.283 (18)
C4—N3	1.277 (16)
N2—C1—C2	114.0 (8)	N2—N1—C3	109.1 (13)
C3—C2—C1	103.9 (13)	N2—N1—C4	118.2 (11)
C2—C3—N1	109.1 (9)	C1—N2—N1	103.8 (9)
N3—C4—N1	118.8 (9)	O1—N5—O3	118.6 (16)
N3—C4—N4	123.7 (14)	O2—N5—O1	124.0 (18)
N4—C4—N1	117.5 (14)	O2—N5—O3	117.3 (10)
C3—N1—C4	132.6 (12)

(0.32GPa)

Crystal data

C4H7N4·NO3	F(000) = 360
Mr = 173.15	Dx = 1.614 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.1064 (10) Å	Cell parameters from 1262 reflections
b = 10.1978 (9) Å	θ = 4.0–22.4°
c = 13.867 (8) Å	µ = 0.14 mm^−1
β = 99.36 (4)°	T = 293 K
V = 712.5 (4) Å^3	Prism, colourless
Z = 4

Data collection

Xcalibur, Sapphire2, large Be window diffractometer	445 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	320 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
Detector resolution: 8.2214 pixels mm^-1	θmax = 25.0°, θmin = 4.0°
ω scans	h = −5→5
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −12→12
Tmin = 0.058, Tmax = 1.000	l = −9→9
3886 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.041	w = 1/[σ^2(Fo^2) + (0.0575P)^2 + 0.3399P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.110	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.11 e Å^−3
445 reflections	Δρmin = −0.11 e Å^−3
110 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.027 (11)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1066 (13)	0.7894 (4)	0.5381 (7)	0.056 (7)
H1	−0.041746	0.829014	0.501960	0.067*
C2	0.3244 (14)	0.8587 (4)	0.5878 (8)	0.058 (8)
H2	0.346449	0.949237	0.590378	0.069*
C3	0.4952 (13)	0.7677 (4)	0.6310 (8)	0.059 (7)
H3	0.658594	0.782716	0.670008	0.071*
C4	0.4770 (13)	0.5233 (4)	0.6291 (8)	0.038 (8)
N1	0.3791 (11)	0.6478 (3)	0.6057 (6)	0.049 (7)
N2	0.1364 (10)	0.6616 (3)	0.5486 (6)	0.057 (6)
N3	0.3385 (10)	0.4243 (3)	0.5910 (6)	0.060 (6)
H3A	0.397206	0.345840	0.602326	0.072*
H3B	0.187725	0.437060	0.554482	0.072*
N4	0.7065 (10)	0.5096 (3)	0.6850 (6)	0.055 (6)
H4A	0.771354	0.432516	0.697837	0.066*
H4B	0.793095	0.577566	0.709029	0.066*
N5	0.2476 (11)	0.6475 (3)	0.8246 (7)	0.055 (7)
O1	0.4843 (8)	0.6736 (2)	0.8566 (5)	0.064 (5)
O2	0.1674 (9)	0.5342 (3)	0.8236 (6)	0.090 (7)
O3	0.0875 (9)	0.7378 (3)	0.7929 (6)	0.077 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.050 (6)	0.045 (3)	0.068 (17)	0.003 (2)	−0.002 (9)	0.000 (3)
C2	0.056 (6)	0.042 (3)	0.073 (18)	−0.004 (2)	0.004 (9)	−0.005 (3)
C3	0.053 (6)	0.045 (3)	0.075 (17)	−0.011 (2)	−0.006 (9)	−0.010 (3)
C4	0.030 (6)	0.045 (3)	0.042 (18)	−0.001 (2)	0.012 (10)	−0.002 (3)
N1	0.041 (5)	0.039 (2)	0.061 (17)	−0.0018 (17)	−0.010 (9)	0.003 (2)
N2	0.042 (4)	0.042 (2)	0.082 (13)	0.0009 (17)	−0.010 (7)	0.002 (2)
N3	0.048 (5)	0.039 (2)	0.085 (14)	0.0019 (18)	−0.015 (7)	−0.002 (3)
N4	0.046 (5)	0.057 (2)	0.057 (13)	0.0008 (19)	−0.011 (7)	0.002 (3)
N5	0.044 (5)	0.053 (3)	0.065 (17)	−0.0019 (19)	−0.001 (9)	−0.002 (3)
O1	0.041 (4)	0.0478 (18)	0.095 (12)	−0.0042 (14)	−0.011 (6)	−0.007 (2)
O2	0.062 (5)	0.047 (2)	0.148 (15)	−0.0168 (17)	−0.023 (8)	−0.004 (3)
O3	0.054 (4)	0.061 (2)	0.106 (14)	0.0089 (17)	−0.018 (8)	0.010 (3)

Geometric parameters (Å, º)

C1—C2	1.400 (6)	C4—N4	1.303 (5)
C1—N2	1.318 (5)	N1—N2	1.366 (4)
C2—C3	1.346 (6)	N5—O1	1.247 (5)
C3—N1	1.380 (5)	N5—O2	1.226 (4)
C4—N1	1.384 (5)	N5—O3	1.261 (4)
C4—N3	1.295 (5)
N2—C1—C2	112.1 (4)	N2—N1—C3	111.6 (3)
C3—C2—C1	106.1 (4)	N2—N1—C4	119.3 (3)
C2—C3—N1	106.1 (4)	C1—N2—N1	104.1 (3)
N3—C4—N1	117.9 (4)	O1—N5—O3	120.3 (4)
N3—C4—N4	122.5 (4)	O2—N5—O1	120.5 (3)
N4—C4—N1	119.6 (3)	O2—N5—O3	119.2 (4)
C3—N1—C4	129.1 (4)

(0.39GPa)

Crystal data

C4H7N4·NO3	F(000) = 360
Mr = 173.15	Dx = 1.624 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.0897 (19) Å	Cell parameters from 424 reflections
b = 10.213 (11) Å	θ = 3.6–20.1°
c = 13.789 (5) Å	µ = 0.14 mm^−1
β = 98.86 (3)°	T = 293 K
V = 708.2 (8) Å^3	Prism, colourless
Z = 4

Data collection

Xcalibur, Sapphire2, large Be window diffractometer	516 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	284 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
Detector resolution: 8.2214 pixels mm^-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −5→5
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −6→6
Tmin = 0.226, Tmax = 1.000	l = −16→16
3763 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.067	H-atom parameters constrained
wR(F^2) = 0.228	w = 1/[σ^2(Fo^2) + (0.1251P)^2 + 0.5955P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
516 reflections	Δρmax = 0.18 e Å^−3
109 parameters	Δρmin = −0.20 e Å^−3
0 restraints

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.107 (2)	0.786 (2)	0.5400 (8)	0.086 (9)
H1	−0.046830	0.824594	0.507050	0.104*
C2	0.3261 (18)	0.8598 (17)	0.5870 (6)	0.064 (7)
H2	0.347978	0.950188	0.588426	0.077*
C3	0.4930 (19)	0.7684 (19)	0.6286 (6)	0.065 (7)
H3	0.657274	0.783750	0.666714	0.078*
C4	0.4753 (18)	0.519 (2)	0.6297 (6)	0.064 (7)
N1	0.3811 (17)	0.6463 (16)	0.6055 (5)	0.060 (7)
N2	0.1382 (15)	0.6637 (16)	0.5466 (6)	0.079 (7)
N3	0.3356 (14)	0.4241 (13)	0.5913 (5)	0.080 (6)
H3A	0.392617	0.345174	0.600808	0.096*
H3B	0.184156	0.438647	0.555852	0.096*
N4	0.7062 (11)	0.5088 (10)	0.6844 (4)	0.070 (4)
H4A	0.775709	0.432730	0.697051	0.084*
H4B	0.789422	0.577779	0.707953	0.084*
N5	0.2458 (19)	0.648 (2)	0.8268 (6)	0.070 (7)
O1	0.4837 (9)	0.6736 (8)	0.8575 (4)	0.080 (4)
O2	0.166 (2)	0.5327 (17)	0.8240 (6)	0.104 (7)
O3	0.0868 (12)	0.7364 (11)	0.7940 (4)	0.086 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.054 (7)	0.12 (3)	0.085 (6)	0.026 (9)	−0.003 (5)	−0.023 (10)
C2	0.073 (9)	0.03 (3)	0.080 (5)	−0.009 (5)	−0.013 (5)	−0.007 (7)
C3	0.046 (7)	0.07 (3)	0.070 (5)	−0.003 (6)	−0.008 (4)	−0.004 (7)
C4	0.027 (7)	0.10 (3)	0.065 (5)	0.008 (5)	0.002 (4)	0.011 (8)
N1	0.040 (7)	0.07 (3)	0.069 (4)	−0.013 (5)	−0.005 (4)	−0.015 (7)
N2	0.027 (6)	0.12 (3)	0.083 (5)	0.007 (6)	−0.010 (4)	−0.016 (7)
N3	0.053 (6)	0.09 (2)	0.091 (5)	0.003 (5)	−0.027 (4)	−0.002 (6)
N4	0.059 (6)	0.056 (16)	0.086 (4)	0.003 (3)	−0.018 (3)	−0.017 (5)
N5	0.045 (8)	0.09 (3)	0.075 (5)	−0.001 (5)	−0.003 (4)	−0.010 (6)
O1	0.034 (4)	0.098 (13)	0.101 (4)	−0.006 (3)	−0.012 (3)	−0.009 (4)
O2	0.065 (6)	0.10 (2)	0.133 (6)	−0.012 (6)	−0.018 (4)	−0.011 (7)
O3	0.043 (5)	0.117 (16)	0.092 (4)	0.010 (4)	−0.007 (3)	0.012 (5)

Geometric parameters (Å, º)

C1—C2	1.42 (2)	C4—N4	1.299 (10)
C1—N2	1.26 (2)	N1—N2	1.382 (12)
C2—C3	1.33 (2)	N5—O1	1.247 (10)
C3—N1	1.39 (2)	N5—O2	1.25 (2)
C4—N1	1.41 (2)	N5—O3	1.25 (2)
C4—N3	1.27 (2)
N2—C1—C2	114.3 (11)	N2—N1—C3	108.6 (17)
C3—C2—C1	103.3 (17)	N2—N1—C4	120.0 (13)
C2—C3—N1	108.6 (9)	C1—N2—N1	105.1 (15)
N3—C4—N1	117.3 (10)	O1—N5—O3	121.1 (19)
N3—C4—N4	125.2 (18)	O2—N5—O1	120 (2)
N4—C4—N1	117.4 (17)	O2—N5—O3	118.8 (11)
C3—N1—C4	131.4 (15)

(0.44GPa)

Crystal data

C4H7N4·NO3	F(000) = 360
Mr = 173.15	Dx = 1.625 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.0963 (11) Å	Cell parameters from 1295 reflections
b = 10.1784 (11) Å	θ = 4.0–22.1°
c = 13.823 (10) Å	µ = 0.14 mm^−1
β = 99.25 (4)°	T = 293 K
V = 707.7 (5) Å^3	Prism, colourless
Z = 4

Data collection

Xcalibur, Sapphire2, large Be window diffractometer	447 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	340 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
Detector resolution: 8.2214 pixels mm^-1	θmax = 25.0°, θmin = 4.0°
ω scans	h = −5→5
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −12→12
Tmin = 0.239, Tmax = 1.000	l = −9→9
3896 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0423P)^2 + 0.7871P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.115	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.12 e Å^−3
447 reflections	Δρmin = −0.12 e Å^−3
110 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.023 (9)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1055 (14)	0.7902 (4)	0.5386 (8)	0.048 (8)
H1	−0.043965	0.829941	0.503073	0.058*
C2	0.3247 (16)	0.8592 (5)	0.5876 (9)	0.056 (8)
H2	0.348879	0.949809	0.589441	0.067*
C3	0.4931 (14)	0.7677 (4)	0.6314 (9)	0.052 (8)
H3	0.654842	0.782557	0.671689	0.063*
C4	0.4757 (14)	0.5235 (4)	0.6298 (9)	0.043 (8)
N1	0.3801 (11)	0.6484 (3)	0.6052 (7)	0.033 (8)
N2	0.1360 (11)	0.6620 (3)	0.5486 (7)	0.055 (7)
N3	0.3368 (12)	0.4238 (3)	0.5917 (7)	0.066 (7)
H3A	0.396670	0.345331	0.602619	0.079*
H3B	0.185031	0.436362	0.555602	0.079*
N4	0.7066 (11)	0.5098 (4)	0.6850 (7)	0.061 (7)
H4A	0.772258	0.432670	0.697351	0.073*
H4B	0.793373	0.577952	0.709046	0.073*
N5	0.2460 (13)	0.6477 (4)	0.8249 (8)	0.068 (8)
O1	0.4838 (9)	0.6737 (3)	0.8570 (5)	0.065 (6)
O2	0.1661 (10)	0.5337 (3)	0.8245 (6)	0.086 (7)
O3	0.0860 (10)	0.7380 (3)	0.7937 (6)	0.062 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.043 (6)	0.047 (3)	0.06 (2)	0.002 (3)	0.010 (10)	0.006 (4)
C2	0.067 (7)	0.043 (3)	0.06 (2)	−0.009 (3)	0.005 (11)	−0.002 (4)
C3	0.049 (6)	0.042 (3)	0.062 (18)	−0.007 (2)	−0.004 (9)	−0.007 (4)
C4	0.034 (6)	0.041 (3)	0.05 (2)	−0.002 (2)	0.004 (10)	−0.001 (4)
N1	0.029 (5)	0.040 (3)	0.029 (18)	0.0000 (18)	0.006 (9)	0.001 (3)
N2	0.041 (5)	0.039 (2)	0.078 (15)	0.0002 (18)	−0.008 (8)	−0.001 (3)
N3	0.057 (5)	0.037 (2)	0.092 (16)	0.001 (2)	−0.025 (9)	0.000 (3)
N4	0.049 (5)	0.052 (3)	0.071 (15)	0.001 (2)	−0.020 (8)	0.002 (3)
N5	0.060 (6)	0.047 (3)	0.087 (19)	0.000 (2)	−0.021 (10)	−0.002 (3)
O1	0.043 (4)	0.047 (2)	0.096 (14)	−0.0064 (16)	−0.017 (7)	−0.005 (3)
O2	0.062 (5)	0.047 (2)	0.136 (16)	−0.0165 (19)	−0.023 (8)	−0.001 (3)
O3	0.042 (5)	0.062 (3)	0.078 (16)	0.0089 (19)	0.002 (8)	0.010 (3)

Geometric parameters (Å, º)

C1—C2	1.399 (7)	C4—N4	1.303 (5)
C1—N2	1.319 (5)	N1—N2	1.366 (5)
C2—C3	1.343 (7)	N5—O1	1.250 (6)
C3—N1	1.368 (5)	N5—O2	1.229 (5)
C4—N1	1.383 (5)	N5—O3	1.258 (5)
C4—N3	1.299 (6)
N2—C1—C2	112.0 (4)	N2—N1—C3	111.6 (3)
C3—C2—C1	105.8 (4)	N2—N1—C4	119.1 (3)
C2—C3—N1	106.6 (4)	C1—N2—N1	104.0 (3)
N3—C4—N1	118.1 (4)	O1—N5—O3	120.3 (4)
N3—C4—N4	122.4 (4)	O2—N5—O1	120.2 (4)
N4—C4—N1	119.4 (4)	O2—N5—O3	119.5 (5)
C3—N1—C4	129.3 (4)

(0.46GPa)

Crystal data

C4H7N4·NO3	F(000) = 360
Mr = 173.15	Dx = 1.629 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.0956 (10) Å	Cell parameters from 1269 reflections
b = 10.1775 (10) Å	θ = 4.0–22.0°
c = 13.792 (9) Å	µ = 0.14 mm^−1
β = 99.13 (4)°	T = 293 K
V = 706.2 (5) Å^3	Prism, colourless
Z = 4

Data collection

Xcalibur, Sapphire2, large Be window diffractometer	445 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	332 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
Detector resolution: 8.2214 pixels mm^-1	θmax = 25.0°, θmin = 4.0°
ω scans	h = −5→5
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −12→12
Tmin = 0.317, Tmax = 1.000	l = −8→9
3896 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.051	w = 1/[σ^2(Fo^2) + (0.0676P)^2 + 0.7303P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.140	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.14 e Å^−3
445 reflections	Δρmin = −0.13 e Å^−3
110 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.031 (15)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1057 (15)	0.7901 (5)	0.5380 (9)	0.059 (9)
H1	−0.042104	0.829642	0.501271	0.071*
C2	0.3233 (17)	0.8596 (5)	0.5885 (10)	0.054 (9)
H2	0.345941	0.950315	0.591083	0.065*
C3	0.4927 (16)	0.7681 (5)	0.6323 (10)	0.062 (8)
H3	0.653608	0.782846	0.673062	0.074*
C4	0.4769 (15)	0.5237 (4)	0.6296 (9)	0.042 (9)
N1	0.3802 (12)	0.6486 (3)	0.6049 (8)	0.059 (9)
N2	0.1360 (11)	0.6620 (3)	0.5488 (7)	0.057 (7)
N3	0.3385 (13)	0.4243 (4)	0.5910 (8)	0.085 (8)
H3A	0.397702	0.345696	0.601959	0.102*
H3B	0.187632	0.437084	0.554371	0.102*
N4	0.7064 (13)	0.5101 (4)	0.6855 (8)	0.071 (8)
H4A	0.771876	0.432903	0.698098	0.086*
H4B	0.792603	0.578207	0.709816	0.086*
N5	0.2456 (14)	0.6475 (4)	0.8253 (8)	0.068 (9)
O1	0.4857 (10)	0.6735 (3)	0.8558 (6)	0.071 (6)
O2	0.1665 (10)	0.5336 (3)	0.8238 (7)	0.094 (7)
O3	0.0865 (10)	0.7376 (3)	0.7934 (7)	0.073 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.060 (7)	0.042 (3)	0.07 (2)	−0.001 (3)	−0.007 (11)	0.005 (4)
C2	0.064 (7)	0.040 (3)	0.06 (2)	−0.002 (3)	0.008 (11)	−0.008 (4)
C3	0.062 (6)	0.044 (3)	0.07 (2)	−0.007 (3)	−0.017 (10)	−0.008 (4)
C4	0.032 (6)	0.040 (3)	0.05 (2)	0.000 (2)	0.010 (11)	0.004 (4)
N1	0.049 (6)	0.037 (3)	0.08 (2)	−0.002 (2)	−0.022 (10)	0.001 (3)
N2	0.039 (5)	0.040 (3)	0.086 (16)	−0.0004 (19)	−0.009 (8)	0.003 (3)
N3	0.069 (6)	0.034 (3)	0.132 (19)	0.002 (2)	−0.044 (10)	−0.003 (3)
N4	0.058 (5)	0.054 (3)	0.088 (18)	0.002 (2)	−0.031 (9)	0.004 (3)
N5	0.057 (6)	0.047 (3)	0.09 (2)	0.002 (2)	−0.019 (10)	−0.001 (3)
O1	0.051 (4)	0.046 (2)	0.104 (14)	−0.0041 (18)	−0.023 (7)	−0.006 (3)
O2	0.068 (5)	0.046 (3)	0.153 (18)	−0.014 (2)	−0.030 (9)	−0.002 (3)
O3	0.055 (5)	0.059 (3)	0.094 (17)	0.005 (2)	−0.014 (9)	0.012 (3)

Geometric parameters (Å, º)

C1—C2	1.404 (8)	C4—N4	1.302 (6)
C1—N2	1.319 (6)	N1—N2	1.363 (5)
C2—C3	1.347 (8)	N5—O1	1.258 (6)
C3—N1	1.372 (6)	N5—O2	1.226 (5)
C4—N1	1.386 (6)	N5—O3	1.256 (5)
C4—N3	1.298 (6)
N2—C1—C2	111.9 (5)	N2—N1—C3	111.8 (4)
C3—C2—C1	105.9 (4)	N2—N1—C4	119.2 (4)
C2—C3—N1	106.2 (5)	C1—N2—N1	104.0 (4)
N3—C4—N1	117.7 (5)	O2—N5—O1	120.3 (4)
N3—C4—N4	122.6 (4)	O2—N5—O3	119.5 (5)
N4—C4—N1	119.6 (4)	O3—N5—O1	120.2 (4)
C3—N1—C4	128.9 (4)

(0.52GPa)

Crystal data

C4H7N4·NO3	F(000) = 360
Mr = 173.15	Dx = 1.638 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.0851 (15) Å	Cell parameters from 1174 reflections
b = 10.1654 (13) Å	θ = 4.0–22.3°
c = 13.751 (13) Å	µ = 0.14 mm^−1
β = 98.93 (6)°	T = 293 K
V = 702.2 (7) Å^3	Prism, colourless
Z = 4

Data collection

Xcalibur, Sapphire2, large Be window diffractometer	438 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	317 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 8.2214 pixels mm^-1	θmax = 25.0°, θmin = 4.0°
ω scans	h = −5→5
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −12→12
Tmin = 0.107, Tmax = 1.000	l = −8→9
3830 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[σ^2(Fo^2) + (0.0796P)^2 + 0.3747P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.141	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.13 e Å^−3
438 reflections	Δρmin = −0.15 e Å^−3
110 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.031 (17)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1059 (15)	0.7904 (5)	0.5377 (9)	0.058 (9)
H1	−0.041590	0.829834	0.500607	0.069*
C2	0.3226 (16)	0.8606 (4)	0.5880 (10)	0.057 (9)
H2	0.344256	0.951404	0.590976	0.068*
C3	0.4921 (16)	0.7690 (4)	0.6309 (10)	0.065 (8)
H3	0.655024	0.784108	0.670404	0.078*
C4	0.4765 (15)	0.5240 (4)	0.6291 (9)	0.040 (9)
N1	0.3793 (12)	0.6488 (3)	0.6055 (8)	0.056 (9)
N2	0.1349 (12)	0.6626 (3)	0.5489 (7)	0.072 (7)
N3	0.3369 (12)	0.4248 (4)	0.5918 (8)	0.072 (8)
H3A	0.395274	0.346042	0.603375	0.086*
H3B	0.185579	0.437516	0.555373	0.086*
N4	0.7062 (12)	0.5106 (4)	0.6846 (7)	0.063 (7)
H4A	0.771089	0.433387	0.697819	0.076*
H4B	0.793389	0.578994	0.708125	0.076*
N5	0.2441 (14)	0.6473 (4)	0.8261 (9)	0.074 (9)
O1	0.4830 (9)	0.6734 (3)	0.8567 (6)	0.076 (6)
O2	0.1661 (10)	0.5335 (3)	0.8248 (7)	0.095 (8)
O3	0.0853 (10)	0.7378 (3)	0.7937 (7)	0.068 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.046 (7)	0.043 (3)	0.08 (2)	0.004 (3)	−0.005 (11)	0.002 (4)
C2	0.060 (7)	0.039 (3)	0.07 (2)	−0.001 (3)	−0.002 (11)	−0.008 (3)
C3	0.059 (7)	0.043 (3)	0.085 (19)	−0.008 (3)	−0.018 (10)	−0.010 (4)
C4	0.035 (6)	0.037 (3)	0.05 (2)	−0.004 (2)	0.008 (11)	0.004 (4)
N1	0.040 (6)	0.037 (3)	0.08 (2)	−0.0022 (19)	−0.018 (10)	0.002 (3)
N2	0.052 (5)	0.038 (3)	0.112 (17)	0.002 (2)	−0.028 (9)	−0.003 (3)
N3	0.055 (6)	0.034 (2)	0.114 (18)	0.004 (2)	−0.028 (9)	−0.004 (3)
N4	0.049 (5)	0.053 (3)	0.078 (17)	0.002 (2)	−0.020 (9)	0.002 (3)
N5	0.055 (6)	0.046 (3)	0.11 (2)	0.001 (2)	−0.027 (11)	−0.004 (3)
O1	0.047 (4)	0.044 (2)	0.123 (15)	−0.0048 (17)	−0.026 (7)	−0.004 (3)
O2	0.064 (5)	0.044 (2)	0.162 (19)	−0.015 (2)	−0.031 (10)	−0.001 (3)
O3	0.045 (5)	0.056 (3)	0.098 (17)	0.0059 (19)	−0.008 (9)	0.011 (3)

Geometric parameters (Å, º)

C1—C2	1.401 (7)	C4—N4	1.300 (6)
C1—N2	1.314 (6)	N1—N2	1.367 (6)
C2—C3	1.342 (7)	N5—O1	1.251 (6)
C3—N1	1.372 (6)	N5—O2	1.223 (5)
C4—N1	1.382 (6)	N5—O3	1.259 (5)
C4—N3	1.293 (6)
N2—C1—C2	112.3 (4)	N2—N1—C3	111.2 (3)
C3—C2—C1	105.4 (4)	N2—N1—C4	119.2 (3)
C2—C3—N1	106.9 (4)	C1—N2—N1	104.1 (4)
N3—C4—N1	118.0 (4)	O1—N5—O3	120.0 (4)
N3—C4—N4	122.6 (4)	O2—N5—O1	120.1 (4)
N4—C4—N1	119.4 (4)	O2—N5—O3	119.9 (5)
C3—N1—C4	129.6 (4)

(0.58GPa)

Crystal data

C4H7N4·NO3	F(000) = 360
Mr = 173.15	Dx = 1.638 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.099 (4) Å	Cell parameters from 239 reflections
b = 10.193 (19) Å	θ = 3.0–23.4°
c = 13.666 (7) Å	µ = 0.14 mm^−1
β = 98.65 (6)°	T = 293 K
V = 702.2 (15) Å^3	Prism, colourless
Z = 4

Data collection

Xcalibur, Sapphire2, large Be window diffractometer	508 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	254 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.084
Detector resolution: 8.2214 pixels mm^-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −5→5
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −6→6
Tmin = 0.259, Tmax = 1.000	l = −16→16
3755 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.066	H-atom parameters constrained
wR(F^2) = 0.229	w = 1/[σ^2(Fo^2) + (0.1044P)^2 + 1.3001P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
508 reflections	Δρmax = 0.16 e Å^−3
109 parameters	Δρmin = −0.16 e Å^−3
0 restraints

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.105 (2)	0.784 (2)	0.5401 (10)	0.098 (11)
H1	−0.052389	0.820560	0.508287	0.118*
C2	0.322 (2)	0.8647 (18)	0.5854 (7)	0.070 (8)
H2	0.340664	0.955430	0.585716	0.084*
C3	0.489 (2)	0.772 (2)	0.6268 (8)	0.058 (7)
H3	0.653307	0.788618	0.664068	0.070*
C4	0.472 (2)	0.521 (2)	0.6281 (7)	0.056 (8)
N1	0.382 (2)	0.6466 (17)	0.6065 (6)	0.048 (7)
N2	0.1382 (19)	0.6594 (17)	0.5458 (9)	0.081 (8)
N3	0.3354 (18)	0.4221 (15)	0.5919 (6)	0.080 (6)
H3A	0.395577	0.343877	0.603544	0.097*
H3B	0.183661	0.433859	0.556072	0.097*
N4	0.7054 (13)	0.5097 (11)	0.6835 (5)	0.075 (5)
H4A	0.772945	0.433262	0.696947	0.090*
H4B	0.790378	0.578715	0.706283	0.090*
N5	0.247 (2)	0.646 (3)	0.8256 (8)	0.086 (8)
O1	0.4827 (11)	0.6741 (9)	0.8565 (5)	0.075 (4)
O2	0.160 (2)	0.535 (2)	0.8249 (8)	0.113 (8)
O3	0.0842 (14)	0.7375 (11)	0.7931 (5)	0.074 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.032 (8)	0.17 (4)	0.083 (8)	0.017 (10)	−0.016 (5)	−0.038 (14)
C2	0.067 (11)	0.05 (3)	0.083 (6)	0.001 (7)	−0.011 (6)	0.004 (9)
C3	0.059 (9)	0.02 (3)	0.087 (7)	−0.016 (7)	−0.003 (6)	−0.004 (9)
C4	0.045 (9)	0.05 (3)	0.073 (7)	0.009 (7)	0.003 (5)	−0.001 (10)
N1	0.047 (8)	0.01 (3)	0.080 (5)	−0.006 (6)	−0.007 (4)	−0.001 (9)
N2	0.038 (7)	0.10 (3)	0.098 (7)	0.002 (7)	−0.011 (5)	−0.005 (10)
N3	0.059 (7)	0.07 (2)	0.096 (6)	0.001 (5)	−0.031 (5)	−0.001 (7)
N4	0.056 (7)	0.065 (18)	0.092 (5)	−0.003 (4)	−0.026 (4)	−0.007 (6)
N5	0.032 (9)	0.14 (3)	0.085 (6)	0.000 (7)	0.004 (5)	−0.022 (9)
O1	0.036 (5)	0.072 (15)	0.111 (5)	−0.004 (3)	−0.013 (3)	−0.007 (5)
O2	0.063 (7)	0.12 (3)	0.138 (8)	−0.023 (7)	−0.029 (5)	0.012 (10)
O3	0.042 (5)	0.068 (18)	0.103 (5)	0.008 (4)	−0.011 (3)	0.011 (6)

Geometric parameters (Å, º)

C1—C2	1.44 (3)	C4—N4	1.317 (12)
C1—N2	1.28 (3)	N1—N2	1.393 (15)
C2—C3	1.34 (2)	N5—O1	1.247 (11)
C3—N1	1.40 (2)	N5—O2	1.21 (3)
C4—N1	1.38 (2)	N5—O3	1.28 (3)
C4—N3	1.28 (2)
N2—C1—C2	116.9 (12)	C4—N1—N2	116.9 (15)
C3—C2—C1	100.2 (18)	N2—N1—C3	108.5 (16)
C2—C3—N1	111.0 (12)	C1—N2—N1	103.2 (15)
N3—C4—N1	120.4 (13)	O1—N5—O3	119 (2)
N3—C4—N4	123.1 (19)	O2—N5—O1	124 (3)
N4—C4—N1	116.5 (19)	O2—N5—O3	117.3 (14)
C4—N1—C3	134.4 (17)

(0.67GPa)

Crystal data

C4H7N4·NO3	F(000) = 360
Mr = 173.15	Dx = 1.655 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.0608 (12) Å	Cell parameters from 766 reflections
b = 10.1526 (10) Å	θ = 4.0–20.5°
c = 13.677 (10) Å	µ = 0.14 mm^−1
β = 98.54 (5)°	T = 293 K
V = 695.0 (6) Å^3	Prism, colourless
Z = 4

Data collection

Xcalibur, Sapphire2, large Be window diffractometer	434 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	312 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
Detector resolution: 8.2214 pixels mm^-1	θmax = 25.0°, θmin = 4.0°
ω scans	h = −5→5
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −12→12
Tmin = 0.015, Tmax = 1.000	l = −9→9
3721 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[σ^2(Fo^2) + (0.0264P)^2 + 0.9907P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.112	(Δ/σ)max < 0.001
S = 1.15	Δρmax = 0.13 e Å^−3
434 reflections	Δρmin = −0.16 e Å^−3
110 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.026 (8)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1019 (16)	0.7907 (5)	0.5387 (10)	0.067 (10)
H1	−0.047704	0.830388	0.502871	0.081*
C2	0.3218 (17)	0.8604 (5)	0.5885 (10)	0.052 (10)
H2	0.343815	0.951386	0.591189	0.063*
C3	0.4935 (16)	0.7695 (5)	0.6315 (10)	0.062 (9)
H3	0.656641	0.784537	0.671079	0.075*
C4	0.4767 (17)	0.5245 (5)	0.6297 (10)	0.043 (10)
N1	0.3785 (14)	0.6495 (4)	0.6051 (9)	0.051 (10)
N2	0.1335 (12)	0.6627 (4)	0.5488 (8)	0.056 (8)
N3	0.3373 (13)	0.4241 (4)	0.5904 (9)	0.056 (9)
H3A	0.398670	0.345445	0.600063	0.068*
H3B	0.184372	0.436830	0.554968	0.068*
N4	0.7087 (13)	0.5108 (4)	0.6838 (7)	0.058 (8)
H4A	0.776102	0.433514	0.694999	0.069*
H4B	0.794805	0.578975	0.708493	0.069*
N5	0.2457 (15)	0.6475 (4)	0.8257 (9)	0.075 (10)
O1	0.4864 (10)	0.6738 (3)	0.8560 (6)	0.076 (7)
O2	0.1657 (11)	0.5327 (4)	0.8253 (7)	0.084 (9)
O3	0.0844 (12)	0.7374 (4)	0.7941 (7)	0.063 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.046 (8)	0.041 (4)	0.11 (2)	0.003 (3)	−0.010 (13)	0.004 (4)
C2	0.057 (8)	0.041 (3)	0.06 (2)	−0.004 (3)	0.002 (12)	−0.008 (4)
C3	0.053 (7)	0.038 (3)	0.09 (2)	−0.008 (3)	−0.017 (12)	−0.004 (4)
C4	0.029 (8)	0.041 (4)	0.06 (2)	−0.004 (3)	0.010 (13)	0.006 (4)
N1	0.037 (6)	0.035 (3)	0.08 (2)	−0.002 (2)	−0.012 (11)	0.002 (4)
N2	0.037 (6)	0.041 (3)	0.085 (18)	0.001 (2)	−0.012 (9)	0.000 (3)
N3	0.052 (7)	0.034 (3)	0.08 (2)	0.001 (2)	−0.014 (11)	0.000 (3)
N4	0.046 (7)	0.052 (3)	0.068 (19)	0.002 (2)	−0.017 (10)	0.001 (3)
N5	0.061 (7)	0.044 (3)	0.11 (2)	0.005 (3)	−0.030 (12)	−0.006 (4)
O1	0.041 (5)	0.046 (2)	0.128 (16)	−0.004 (2)	−0.027 (8)	−0.005 (3)
O2	0.058 (7)	0.045 (3)	0.14 (2)	−0.014 (2)	−0.021 (11)	0.000 (3)
O3	0.049 (6)	0.058 (3)	0.078 (18)	0.008 (2)	−0.005 (10)	0.011 (3)

Geometric parameters (Å, º)

C1—C2	1.407 (7)	C4—N4	1.299 (6)
C1—N2	1.314 (6)	N1—N2	1.365 (6)
C2—C3	1.342 (7)	N5—O1	1.255 (6)
C3—N1	1.375 (6)	N5—O2	1.234 (6)
C4—N1	1.386 (6)	N5—O3	1.258 (5)
C4—N3	1.308 (6)
N2—C1—C2	111.8 (5)	N2—N1—C3	112.0 (4)
C3—C2—C1	106.3 (4)	N2—N1—C4	119.3 (4)
C2—C3—N1	105.8 (5)	C1—N2—N1	104.1 (4)
N3—C4—N1	117.5 (5)	O1—N5—O3	120.5 (5)
N4—C4—N1	119.8 (4)	O2—N5—O1	120.3 (4)
N4—C4—N3	122.5 (5)	O2—N5—O3	119.2 (5)
C3—N1—C4	128.7 (4)

(0.89GPa)

Crystal data

C4H7N4·NO3	F(000) = 360
Mr = 173.15	Dx = 1.676 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.036 (2) Å	Cell parameters from 414 reflections
b = 10.162 (2) Å	θ = 4.0–20.6°
c = 13.54 (2) Å	µ = 0.14 mm^−1
β = 97.94 (9)°	T = 293 K
V = 686.1 (12) Å^3	Prism, colourless
Z = 4

Data collection

Xcalibur, Sapphire2, large Be window diffractometer	421 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	271 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
Detector resolution: 8.2214 pixels mm^-1	θmax = 25.0°, θmin = 4.0°
ω scans	h = −5→5
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −11→12
Tmin = 0.177, Tmax = 1.000	l = −8→8
3600 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0809P)^2 + 0.5673P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.150	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.15 e Å^−3
421 reflections	Δρmin = −0.15 e Å^−3
110 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.036 (18)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1050 (19)	0.7917 (6)	0.5371 (12)	0.076 (11)
H1	−0.042516	0.831590	0.500110	0.091*
C2	0.3218 (18)	0.8616 (6)	0.5885 (12)	0.053 (10)
H2	0.342760	0.952466	0.592276	0.064*
C3	0.4927 (19)	0.7700 (5)	0.6312 (12)	0.079 (10)
H3	0.655498	0.784792	0.671118	0.095*
C4	0.477 (2)	0.5242 (5)	0.6303 (13)	0.075 (13)
N1	0.3791 (15)	0.6499 (4)	0.6041 (11)	0.094 (11)
N2	0.1335 (13)	0.6631 (4)	0.5471 (9)	0.082 (9)
N3	0.3377 (16)	0.4250 (4)	0.5900 (11)	0.094 (10)
H3A	0.399087	0.346228	0.598627	0.112*
H3B	0.184465	0.438250	0.554679	0.112*
N4	0.7086 (15)	0.5112 (5)	0.6842 (9)	0.072 (9)
H4A	0.777881	0.434291	0.694881	0.086*
H4B	0.793305	0.579540	0.709370	0.086*
N5	0.2445 (16)	0.6470 (5)	0.8270 (10)	0.082 (11)
O1	0.4865 (11)	0.6736 (3)	0.8560 (8)	0.074 (7)
O2	0.1650 (13)	0.5327 (4)	0.8259 (9)	0.085 (10)
O3	0.0857 (12)	0.7376 (4)	0.7932 (8)	0.085 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.062 (9)	0.044 (4)	0.11 (3)	0.002 (3)	−0.022 (14)	0.007 (5)
C2	0.052 (8)	0.043 (4)	0.07 (2)	−0.005 (3)	0.008 (13)	−0.006 (5)
C3	0.063 (7)	0.040 (4)	0.12 (2)	−0.008 (4)	−0.032 (12)	−0.007 (5)
C4	0.052 (9)	0.034 (4)	0.13 (3)	−0.013 (3)	−0.026 (17)	0.013 (5)
N1	0.058 (8)	0.032 (3)	0.17 (3)	0.001 (3)	−0.051 (13)	−0.002 (4)
N2	0.056 (6)	0.039 (3)	0.14 (2)	0.004 (3)	−0.039 (11)	−0.001 (4)
N3	0.072 (7)	0.033 (3)	0.16 (2)	0.003 (3)	−0.054 (12)	0.001 (4)
N4	0.058 (7)	0.054 (3)	0.09 (2)	0.001 (3)	−0.030 (11)	0.005 (4)
N5	0.049 (7)	0.044 (4)	0.14 (3)	0.003 (3)	−0.026 (13)	−0.009 (5)
O1	0.044 (5)	0.044 (3)	0.126 (18)	−0.004 (2)	−0.019 (9)	−0.001 (3)
O2	0.056 (7)	0.042 (3)	0.15 (2)	−0.013 (2)	−0.013 (12)	−0.003 (3)
O3	0.060 (6)	0.055 (3)	0.13 (2)	0.006 (2)	−0.026 (11)	0.019 (4)

Geometric parameters (Å, º)

C1—C2	1.404 (9)	C4—N4	1.295 (7)
C1—N2	1.319 (7)	N1—N2	1.370 (7)
C2—C3	1.342 (9)	N5—O1	1.257 (7)
C3—N1	1.376 (7)	N5—O2	1.228 (7)
C4—N1	1.397 (8)	N5—O3	1.263 (6)
C4—N3	1.304 (8)
N2—C1—C2	112.6 (5)	N2—N1—C3	111.9 (4)
C3—C2—C1	105.7 (5)	N2—N1—C4	119.4 (4)
C2—C3—N1	106.4 (5)	C1—N2—N1	103.4 (4)
N3—C4—N1	116.8 (6)	O1—N5—O3	119.7 (5)
N4—C4—N1	119.6 (5)	O2—N5—O1	120.5 (5)
N4—C4—N3	123.2 (5)	O2—N5—O3	119.7 (5)
C3—N1—C4	128.7 (5)

(1.11GPa)

Crystal data

C4H7N4·NO3	F(000) = 360
Mr = 173.15	Dx = 1.693 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.024 (5) Å	Cell parameters from 239 reflections
b = 10.158 (4) Å	θ = 4.0–19.5°
c = 13.43 (4) Å	µ = 0.14 mm^−1
β = 97.88 (18)°	T = 293 K
V = 679 (2) Å^3	Prism, colourless
Z = 4

Data collection

Xcalibur, Sapphire2, large Be window diffractometer	413 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	236 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.101
Detector resolution: 8.2214 pixels mm^-1	θmax = 25.0°, θmin = 4.0°
ω scans	h = −5→5
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −12→12
Tmin = 0.066, Tmax = 1.000	l = −9→8
3583 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.054	w = 1/[σ^2(Fo^2) + (0.0811P)^2 + 0.7055P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.163	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.14 e Å^−3
413 reflections	Δρmin = −0.13 e Å^−3
110 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.027 (18)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.104 (2)	0.7921 (8)	0.5385 (15)	0.095 (15)
H1	−0.045567	0.831751	0.501851	0.114*
C2	0.321 (2)	0.8624 (7)	0.5878 (15)	0.064 (13)
H2	0.342663	0.953298	0.590322	0.076*
C3	0.493 (2)	0.7714 (6)	0.6309 (14)	0.095 (13)
H3	0.659806	0.786939	0.668695	0.114*
C4	0.473 (3)	0.5242 (6)	0.6336 (17)	0.104 (17)
N1	0.3751 (19)	0.6498 (5)	0.6083 (14)	0.116 (15)
N2	0.1317 (17)	0.6633 (5)	0.5494 (11)	0.088 (11)
N3	0.3397 (19)	0.4247 (5)	0.5882 (13)	0.098 (13)
H3A	0.409986	0.347346	0.591466	0.117*
H3B	0.182438	0.436907	0.555269	0.117*
N4	0.7097 (19)	0.5114 (6)	0.6842 (11)	0.090 (12)
H4A	0.786317	0.435568	0.689049	0.108*
H4B	0.790687	0.578824	0.712880	0.108*
N5	0.245 (2)	0.6483 (6)	0.8285 (13)	0.091 (14)
O1	0.4873 (14)	0.6738 (4)	0.8566 (9)	0.082 (9)
O2	0.1637 (17)	0.5315 (5)	0.8273 (11)	0.099 (12)
O3	0.0838 (16)	0.7380 (5)	0.7945 (10)	0.103 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.074 (11)	0.054 (6)	0.14 (3)	0.008 (4)	−0.044 (18)	−0.005 (7)
C2	0.066 (11)	0.048 (5)	0.07 (3)	−0.010 (4)	−0.004 (17)	−0.002 (6)
C3	0.069 (10)	0.037 (4)	0.16 (3)	0.001 (4)	−0.041 (16)	−0.016 (6)
C4	0.076 (12)	0.032 (5)	0.18 (4)	−0.011 (4)	−0.05 (2)	0.014 (7)
N1	0.060 (9)	0.032 (4)	0.23 (3)	−0.005 (3)	−0.062 (17)	0.004 (6)
N2	0.062 (8)	0.040 (4)	0.15 (3)	−0.001 (3)	−0.038 (13)	0.001 (5)
N3	0.072 (10)	0.037 (4)	0.17 (3)	0.000 (3)	−0.043 (16)	0.013 (5)
N4	0.077 (10)	0.061 (5)	0.11 (3)	0.006 (4)	−0.049 (16)	−0.003 (5)
N5	0.083 (11)	0.047 (5)	0.13 (3)	0.003 (4)	−0.044 (17)	−0.013 (6)
O1	0.050 (6)	0.046 (3)	0.14 (2)	−0.005 (3)	−0.022 (11)	−0.004 (4)
O2	0.075 (9)	0.044 (4)	0.16 (3)	−0.014 (3)	−0.027 (16)	0.006 (4)
O3	0.064 (8)	0.055 (4)	0.17 (3)	0.006 (3)	−0.033 (14)	0.021 (5)

Geometric parameters (Å, º)

C1—C2	1.395 (11)	C4—N4	1.294 (9)
C1—N2	1.322 (9)	N1—N2	1.369 (9)
C2—C3	1.341 (10)	N5—O1	1.253 (10)
C3—N1	1.386 (9)	N5—O2	1.254 (8)
C4—N1	1.392 (9)	N5—O3	1.262 (7)
C4—N3	1.315 (10)
N2—C1—C2	112.9 (7)	N2—N1—C3	111.1 (6)
C3—C2—C1	105.7 (6)	N2—N1—C4	119.3 (6)
C2—C3—N1	106.7 (7)	C1—N2—N1	103.7 (5)
N3—C4—N1	116.9 (8)	O1—N5—O2	120.0 (6)
N4—C4—N1	119.2 (6)	O1—N5—O3	120.6 (7)
N4—C4—N3	122.6 (8)	O2—N5—O3	119.2 (7)
C3—N1—C4	129.6 (6)

(1.15GPa)

Crystal data

C4H7N4·NO3	F(000) = 360
Mr = 173.15	Dx = 1.702 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.028 (6) Å	Cell parameters from 163 reflections
b = 10.152 (6) Å	θ = 4.0–18.9°
c = 13.36 (5) Å	µ = 0.15 mm^−1
β = 97.9 (2)°	T = 293 K
V = 676 (3) Å^3	Prism, colourless
Z = 4

Data collection

Xcalibur, Sapphire2, large Be window diffractometer	403 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	221 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.128
Detector resolution: 8.2214 pixels mm^-1	θmax = 24.8°, θmin = 4.0°
ω scans	h = −5→5
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −11→11
Tmin = 0.073, Tmax = 1.000	l = −8→8
3550 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.059	w = 1/[σ^2(Fo^2) + (0.0966P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.173	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.14 e Å^−3
403 reflections	Δρmin = −0.12 e Å^−3
110 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.03 (2)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.104 (3)	0.7926 (7)	0.5354 (16)	0.087 (14)
H1	−0.040828	0.832219	0.495982	0.104*
C2	0.320 (3)	0.8628 (8)	0.5892 (18)	0.076 (15)
H2	0.338585	0.953765	0.593889	0.091*
C3	0.492 (3)	0.7714 (7)	0.6323 (17)	0.116 (15)
H3	0.657604	0.786659	0.671180	0.139*
C4	0.479 (3)	0.5252 (7)	0.6297 (19)	0.080 (18)
N1	0.376 (2)	0.6504 (5)	0.6075 (16)	0.120 (16)
N2	0.1322 (19)	0.6642 (5)	0.5475 (13)	0.093 (12)
N3	0.334 (2)	0.4248 (6)	0.5915 (16)	0.127 (16)
H3A	0.393602	0.345741	0.601675	0.152*
H3B	0.180280	0.438127	0.556299	0.152*
N4	0.711 (2)	0.5115 (6)	0.6828 (12)	0.092 (13)
H4A	0.776937	0.434071	0.694750	0.110*
H4B	0.799151	0.579725	0.706518	0.110*
N5	0.246 (2)	0.6470 (7)	0.8289 (14)	0.076 (15)
O1	0.4900 (15)	0.6739 (4)	0.8551 (10)	0.096 (11)
O2	0.1661 (19)	0.5325 (5)	0.8283 (13)	0.125 (15)
O3	0.0833 (19)	0.7380 (5)	0.7953 (12)	0.127 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.090 (12)	0.049 (5)	0.11 (3)	0.008 (5)	−0.017 (19)	−0.005 (7)
C2	0.072 (12)	0.051 (5)	0.11 (4)	−0.007 (5)	0.026 (19)	−0.009 (7)
C3	0.085 (12)	0.047 (5)	0.20 (4)	0.000 (5)	−0.035 (19)	−0.018 (8)
C4	0.061 (12)	0.039 (5)	0.14 (4)	−0.006 (5)	0.01 (2)	0.003 (8)
N1	0.071 (11)	0.038 (5)	0.23 (4)	−0.001 (4)	−0.038 (19)	−0.003 (6)
N2	0.070 (8)	0.049 (4)	0.15 (3)	0.004 (3)	−0.021 (14)	−0.011 (5)
N3	0.086 (12)	0.042 (4)	0.24 (4)	0.001 (4)	−0.034 (19)	0.010 (6)
N4	0.072 (10)	0.062 (5)	0.13 (3)	0.001 (4)	−0.027 (16)	0.004 (6)
N5	0.086 (12)	0.052 (5)	0.08 (4)	−0.003 (4)	−0.012 (18)	−0.008 (6)
O1	0.059 (7)	0.058 (4)	0.16 (3)	−0.005 (3)	−0.016 (13)	−0.012 (5)
O2	0.097 (11)	0.050 (4)	0.21 (3)	−0.014 (4)	−0.034 (19)	−0.002 (5)
O3	0.084 (9)	0.063 (4)	0.22 (3)	0.007 (3)	−0.031 (17)	0.016 (5)

Geometric parameters (Å, º)

C1—C2	1.408 (12)	C4—N4	1.283 (10)
C1—N2	1.319 (9)	N1—N2	1.377 (10)
C2—C3	1.346 (12)	N5—O1	1.258 (11)
C3—N1	1.381 (9)	N5—O2	1.229 (9)
C4—N1	1.390 (10)	N5—O3	1.274 (8)
C4—N3	1.315 (10)
N2—C1—C2	112.1 (7)	N2—N1—C3	111.3 (7)
C3—C2—C1	106.0 (7)	N2—N1—C4	119.6 (6)
C2—C3—N1	106.5 (8)	C1—N2—N1	104.1 (6)
N3—C4—N1	117.1 (8)	O1—N5—O3	119.6 (7)
N4—C4—N1	120.0 (7)	O2—N5—O1	120.8 (7)
N4—C4—N3	122.9 (7)	O2—N5—O3	119.3 (8)
C3—N1—C4	129.0 (8)

(1.27GPa)

Crystal data

C4H7N4·NO3	F(000) = 360
Mr = 173.15	Dx = 1.712 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.984 (12) Å	Cell parameters from 110 reflections
b = 10.093 (11) Å	θ = 4.0–18.8°
c = 13.53 (12) Å	µ = 0.15 mm^−1
β = 99.3 (4)°	T = 293 K
V = 672 (6) Å^3	Prism, colourless
Z = 4

Data collection

Xcalibur, Sapphire2, large Be window diffractometer	405 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	196 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.171
Detector resolution: 8.2214 pixels mm^-1	θmax = 24.9°, θmin = 4.1°
ω scans	h = −5→5
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −11→11
Tmin = 0.681, Tmax = 1.000	l = −8→7
3512 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.066	H-atom parameters constrained
wR(F^2) = 0.174	w = 1/[σ^2(Fo^2) + (0.0726P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
405 reflections	Δρmax = 0.12 e Å^−3
109 parameters	Δρmin = −0.15 e Å^−3
6 restraints

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.096 (3)	0.7943 (9)	0.5408 (19)	0.11 (2)
H1	−0.062400	0.834015	0.508430	0.130*
C2	0.319 (3)	0.8632 (9)	0.586 (2)	0.077 (6)
H2	0.341519	0.954667	0.587491	0.092*
C3	0.498 (3)	0.7714 (8)	0.6281 (19)	0.112 (18)
H3	0.668213	0.786919	0.665614	0.134*
C4	0.475 (3)	0.5246 (8)	0.630 (2)	0.08 (2)
N1	0.379 (2)	0.6502 (6)	0.6047 (18)	0.06 (2)
N2	0.1322 (19)	0.6644 (6)	0.5484 (14)	0.109 (15)
N3	0.333 (2)	0.4250 (6)	0.5907 (18)	0.093 (17)
H3A	0.395346	0.345798	0.600219	0.111*
H3B	0.175462	0.437804	0.555122	0.111*
N4	0.714 (2)	0.5119 (6)	0.6843 (14)	0.130 (16)
H4A	0.784664	0.434480	0.695706	0.156*
H4B	0.802015	0.580929	0.708820	0.156*
N5	0.245 (3)	0.6454 (9)	0.8281 (19)	0.10 (3)
O1	0.4861 (17)	0.6737 (5)	0.8568 (13)	0.114 (13)
O2	0.1636 (19)	0.5297 (6)	0.8283 (14)	0.139 (17)
O3	0.0816 (16)	0.7362 (6)	0.7981 (12)	0.089 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.106 (14)	0.057 (7)	0.15 (5)	0.008 (6)	−0.01 (2)	0.002 (10)
C2	0.086 (8)	0.071 (5)	0.078 (13)	−0.016 (6)	0.026 (9)	0.002 (7)
C3	0.075 (10)	0.056 (6)	0.20 (5)	0.009 (6)	0.002 (19)	−0.016 (9)
C4	0.062 (11)	0.038 (6)	0.16 (6)	0.003 (5)	0.03 (3)	−0.013 (9)
N1	0.051 (11)	0.057 (6)	0.07 (5)	−0.008 (4)	0.04 (2)	0.007 (7)
N2	0.069 (9)	0.054 (5)	0.19 (4)	−0.011 (4)	−0.021 (16)	0.006 (6)
N3	0.075 (10)	0.041 (5)	0.16 (4)	0.000 (4)	0.016 (19)	0.016 (7)
N4	0.087 (10)	0.060 (5)	0.22 (4)	0.000 (4)	−0.036 (17)	0.000 (7)
N5	0.067 (12)	0.076 (7)	0.16 (7)	−0.001 (6)	−0.01 (3)	0.006 (10)
O1	0.063 (7)	0.052 (4)	0.22 (3)	0.001 (3)	−0.005 (14)	−0.011 (6)
O2	0.100 (10)	0.047 (4)	0.25 (4)	−0.030 (4)	−0.03 (2)	0.014 (6)
O3	0.055 (8)	0.086 (5)	0.13 (4)	−0.005 (4)	0.032 (17)	0.014 (7)

Geometric parameters (Å, º)

C1—C2	1.366 (14)	C4—N4	1.305 (12)
C1—N2	1.325 (11)	N1—N2	1.343 (12)
C2—C3	1.347 (12)	N5—O1	1.236 (11)
C3—N1	1.374 (10)	N5—O2	1.235 (11)
C4—N1	1.378 (11)	N5—O3	1.249 (9)
C4—N3	1.292 (11)
N2—C1—C2	112.3 (9)	N2—N1—C3	110.9 (8)
C3—C2—C1	105.8 (9)	N2—N1—C4	119.1 (7)
C2—C3—N1	106.4 (10)	C1—N2—N1	104.4 (7)
N3—C4—N1	118.1 (10)	O1—N5—O3	118.8 (9)
N3—C4—N4	123.0 (8)	O2—N5—O1	121.4 (8)
N4—C4—N1	118.6 (8)	O2—N5—O3	119.8 (9)
C3—N1—C4	130.0 (10)

(100K)

Crystal data

C4H7N4·NO3	Z = 4
Mr = 173.15	F(000) = 360
Triclinic, P1	Dx = 1.635 Mg m^−3
a = 5.0927 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2465 (3) Å	Cell parameters from 2734 reflections
c = 13.6617 (4) Å	θ = 5.8–29.0°
α = 88.714 (3)°	µ = 0.14 mm^−1
β = 98.962 (3)°	T = 100 K
γ = 92.480 (3)°	Prism, colourless
V = 703.45 (4) Å^3	0.49 × 0.38 × 0.33 mm

Data collection

Xcalibur, Atlas diffractometer	2716 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2045 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 10.6249 pixels mm^-1	θmax = 29.2°, θmin = 2.5°
ω scans	h = −6→6
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −14→13
Tmin = 0.922, Tmax = 1.000	l = −18→18
6317 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.058P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
2716 reflections	Δρmax = 0.21 e Å^−3
217 parameters	Δρmin = −0.21 e Å^−3
0 restraints

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C11	−0.3861 (3)	0.21428 (12)	0.03993 (11)	0.0186 (3)
H11	−0.534865	0.171800	0.004444	0.022*
C12	−0.1637 (3)	0.14934 (12)	0.08833 (11)	0.0188 (3)
H12	−0.138943	0.059862	0.090650	0.023*
C13	0.0081 (3)	0.24472 (12)	0.13113 (11)	0.0176 (3)
H13	0.174993	0.233938	0.168394	0.021*
C14	−0.0191 (3)	0.48732 (12)	0.12935 (10)	0.0162 (3)
C21	1.3897 (3)	−0.28961 (12)	0.46444 (11)	0.0193 (3)
H21	1.537735	−0.326835	0.501267	0.023*
C22	1.1723 (3)	−0.36299 (12)	0.41352 (11)	0.0198 (3)
H22	1.150663	−0.453483	0.410612	0.024*
C23	1.0004 (3)	−0.27290 (12)	0.36938 (11)	0.0185 (3)
H23	0.836362	−0.289373	0.330215	0.022*
C24	1.0205 (3)	−0.02909 (12)	0.37019 (10)	0.0153 (3)
N2	0.7517 (3)	0.34022 (10)	0.32221 (9)	0.0183 (3)
N11	−0.1172 (3)	0.36093 (10)	0.10771 (9)	0.0159 (3)
N12	−0.3608 (2)	0.34228 (10)	0.05037 (9)	0.0173 (3)
N13	−0.1637 (3)	0.58361 (10)	0.08997 (9)	0.0198 (3)
H13A	−0.107843	0.663193	0.100737	0.024*
H13B	−0.314246	0.567169	0.053376	0.024*
N14	0.2094 (2)	0.50762 (10)	0.18505 (9)	0.0195 (3)
H14A	0.270361	0.586163	0.197119	0.023*
H14B	0.299833	0.442513	0.209853	0.023*
N21	1.1198 (3)	−0.15233 (10)	0.39479 (9)	0.0170 (3)
N22	1.3609 (2)	−0.16279 (10)	0.45428 (9)	0.0177 (3)
N23	1.1631 (3)	0.07258 (10)	0.40890 (9)	0.0195 (3)
H23A	1.107293	0.150102	0.396243	0.023*
H23B	1.312039	0.061497	0.446861	0.023*
N24	0.7947 (2)	−0.01891 (10)	0.31254 (9)	0.0193 (3)
H24A	0.731791	0.056853	0.298004	0.023*
H24B	0.707797	−0.087907	0.288793	0.023*
O21	0.99244 (19)	0.32225 (8)	0.35522 (7)	0.0202 (2)
O22	0.5960 (2)	0.24491 (9)	0.29448 (8)	0.0232 (3)
O23	0.6680 (2)	0.45255 (9)	0.31662 (9)	0.0290 (3)
N1	0.2524 (3)	0.86582 (10)	0.17230 (9)	0.0176 (3)
O11	0.4124 (2)	0.77799 (8)	0.20569 (8)	0.0212 (2)
O12	0.01163 (19)	0.83490 (8)	0.14291 (8)	0.0209 (2)
O13	0.3334 (2)	0.98037 (9)	0.16892 (10)	0.0328 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0195 (8)	0.0168 (6)	0.0191 (8)	−0.0030 (5)	0.0022 (6)	−0.0013 (5)
C12	0.0208 (8)	0.0170 (6)	0.0187 (8)	0.0016 (5)	0.0033 (6)	0.0013 (5)
C13	0.0158 (8)	0.0193 (6)	0.0177 (8)	0.0044 (5)	0.0018 (6)	0.0044 (5)
C14	0.0162 (8)	0.0166 (6)	0.0160 (8)	−0.0011 (5)	0.0032 (6)	0.0008 (5)
C21	0.0201 (8)	0.0185 (6)	0.0184 (8)	0.0005 (5)	0.0008 (6)	0.0019 (5)
C22	0.0232 (9)	0.0172 (6)	0.0188 (8)	−0.0020 (5)	0.0028 (7)	−0.0004 (5)
C23	0.0175 (8)	0.0193 (6)	0.0176 (8)	−0.0063 (5)	0.0013 (6)	−0.0027 (5)
C24	0.0140 (8)	0.0180 (6)	0.0136 (7)	−0.0006 (5)	0.0023 (6)	0.0011 (5)
N2	0.0176 (7)	0.0212 (6)	0.0154 (7)	0.0000 (4)	0.0009 (5)	0.0029 (4)
N11	0.0134 (7)	0.0165 (5)	0.0165 (7)	−0.0002 (4)	−0.0010 (5)	0.0010 (4)
N12	0.0140 (7)	0.0190 (5)	0.0174 (7)	−0.0010 (4)	−0.0015 (5)	0.0004 (4)
N13	0.0167 (7)	0.0150 (5)	0.0245 (7)	−0.0031 (4)	−0.0059 (5)	0.0003 (4)
N14	0.0160 (7)	0.0194 (6)	0.0213 (7)	−0.0013 (4)	−0.0023 (5)	−0.0001 (4)
N21	0.0162 (7)	0.0159 (6)	0.0183 (7)	−0.0018 (4)	0.0011 (5)	−0.0003 (4)
N22	0.0139 (7)	0.0194 (5)	0.0180 (7)	−0.0006 (4)	−0.0024 (5)	0.0008 (4)
N23	0.0165 (7)	0.0145 (5)	0.0243 (7)	−0.0012 (4)	−0.0058 (5)	0.0009 (4)
N24	0.0164 (7)	0.0177 (6)	0.0220 (7)	−0.0003 (4)	−0.0026 (5)	−0.0002 (4)
O21	0.0131 (5)	0.0201 (5)	0.0255 (6)	0.0014 (4)	−0.0028 (4)	0.0016 (4)
O22	0.0175 (6)	0.0262 (5)	0.0242 (6)	−0.0067 (4)	−0.0004 (5)	−0.0041 (4)
O23	0.0232 (7)	0.0213 (5)	0.0398 (7)	0.0066 (4)	−0.0046 (5)	0.0039 (4)
N1	0.0170 (7)	0.0187 (5)	0.0158 (6)	−0.0021 (4)	−0.0007 (5)	−0.0010 (4)
O11	0.0174 (6)	0.0199 (5)	0.0251 (6)	0.0019 (4)	−0.0006 (5)	0.0033 (4)
O12	0.0123 (6)	0.0210 (5)	0.0281 (6)	−0.0027 (4)	−0.0007 (4)	−0.0017 (4)
O13	0.0245 (7)	0.0176 (5)	0.0499 (8)	−0.0067 (4)	−0.0113 (6)	0.0051 (4)

Geometric parameters (Å, º)

C11—C12	1.405 (2)	C24—N21	1.3953 (17)
C11—N12	1.3211 (16)	C24—N23	1.3161 (18)
C12—C13	1.362 (2)	C24—N24	1.2951 (18)
C13—N11	1.3828 (17)	N2—O21	1.2587 (16)
C14—N11	1.3889 (17)	N2—O22	1.2576 (16)
C14—N13	1.3118 (18)	N2—O23	1.2412 (13)
C14—N14	1.2988 (18)	N11—N12	1.3683 (17)
C21—C22	1.409 (2)	N21—N22	1.3696 (17)
C21—N22	1.3159 (16)	N1—O11	1.2693 (15)
C22—C23	1.365 (2)	N1—O12	1.2586 (16)
C23—N21	1.3803 (17)	N1—O13	1.2294 (14)
N12—C11—C12	112.61 (13)	O23—N2—O21	119.82 (12)
C13—C12—C11	105.67 (11)	O23—N2—O22	119.92 (13)
C12—C13—N11	105.75 (14)	C13—N11—C14	128.35 (15)
N13—C14—N11	117.36 (15)	N12—N11—C13	112.16 (11)
N14—C14—N11	120.54 (12)	N12—N11—C14	119.33 (11)
N14—C14—N13	122.08 (12)	C11—N12—N11	103.81 (10)
N22—C21—C22	112.78 (12)	C23—N21—C24	128.13 (15)
C23—C22—C21	105.30 (12)	N22—N21—C23	112.12 (11)
C22—C23—N21	105.89 (14)	N22—N21—C24	119.70 (11)
N23—C24—N21	117.23 (14)	C21—N22—N21	103.91 (10)
N24—C24—N21	119.79 (12)	O12—N1—O11	119.68 (11)
N24—C24—N23	122.97 (12)	O13—N1—O11	119.87 (13)
O22—N2—O21	120.26 (11)	O13—N1—O12	120.46 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13A···O12	0.86	1.91	2.7628 (14)	172
N13—H13B···N12^i	0.86	2.23	2.9607 (17)	143
N14—H14A···O11	0.86	2.06	2.9188 (15)	172
N14—H14B···O22	0.86	2.71	3.5663 (15)	177
N14—H14B···O23	0.86	2.19	2.7864 (16)	126
N23—H23A···O21	0.86	1.93	2.7834 (13)	174
N23—H23B···N22^ii	0.86	2.21	2.9493 (18)	144
N24—H24A···O22	0.86	2.07	2.9191 (13)	168
N24—H24B···O11^iii	0.86	2.19	3.0253 (15)	164

Symmetry codes: (i) −x−1, −y+1, −z; (ii) −x+3, −y, −z+1; (iii) x, y−1, z.

(300K)

Crystal data

NO3·C4H7N4	F(000) = 360
Mr = 173.15	Dx = 1.572 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.1532 (2) Å	Cell parameters from 2944 reflections
b = 10.2613 (4) Å	θ = 3.5–28.7°
c = 14.0623 (7) Å	µ = 0.13 mm^−1
β = 100.401 (5)°	T = 300 K
V = 731.38 (6) Å^3	Prism, colourless
Z = 4	0.49 × 0.36 × 0.32 mm

Data collection

Xcalibur, Atlas diffractometer	1792 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	1313 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 10.6249 pixels mm^-1	θmax = 29.2°, θmin = 3.6°
ω scans	h = −7→6
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −14→13
Tmin = 0.820, Tmax = 1.000	l = −19→19
7849 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.0613P)^2 + 0.1088P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1792 reflections	Δρmax = 0.12 e Å^−3
114 parameters	Δρmin = −0.21 e Å^−3
0 restraints

Special details

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5158 (2)	0.67349 (10)	0.14231 (9)	0.0618 (3)
O2	0.8291 (3)	0.53593 (12)	0.17855 (13)	0.0947 (5)
O3	0.9086 (2)	0.73790 (12)	0.20697 (9)	0.0674 (4)
C1	0.8875 (3)	0.78677 (15)	0.46172 (11)	0.0555 (4)
H1	1.035698	0.826486	0.497597	0.068 (5)*
C2	0.6694 (3)	0.85583 (15)	0.41203 (12)	0.0576 (4)
H2	0.646725	0.945745	0.409058	0.062 (5)*
C3	0.5006 (3)	0.76454 (15)	0.36971 (11)	0.0530 (4)
H3	0.336254	0.778945	0.331375	0.074 (5)*
C4	0.5214 (3)	0.52205 (13)	0.37096 (9)	0.0442 (3)
N1	0.6169 (2)	0.64581 (11)	0.39384 (8)	0.0446 (3)
N2	0.8595 (2)	0.66018 (11)	0.45209 (9)	0.0508 (3)
N3	0.6608 (2)	0.42348 (13)	0.40872 (9)	0.0575 (4)
H3A	0.603281	0.345436	0.396687	0.073 (6)*
H3B	0.810606	0.436180	0.445781	0.087*
N4	0.2933 (2)	0.50738 (14)	0.31439 (9)	0.0582 (4)
H4A	0.230762	0.430492	0.301066	0.072 (6)*
H4B	0.205343	0.574588	0.290410	0.086*
N5	0.7515 (2)	0.64833 (12)	0.17554 (9)	0.0524 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0412 (6)	0.0555 (6)	0.0815 (8)	0.0055 (4)	−0.0079 (5)	0.0062 (5)
O2	0.0662 (9)	0.0587 (8)	0.1421 (13)	0.0186 (6)	−0.0270 (8)	0.0041 (8)
O3	0.0500 (6)	0.0748 (8)	0.0723 (7)	−0.0079 (5)	−0.0026 (5)	−0.0112 (6)
C1	0.0565 (8)	0.0478 (8)	0.0591 (9)	−0.0013 (7)	0.0020 (7)	−0.0030 (7)
C2	0.0658 (10)	0.0456 (8)	0.0605 (9)	0.0082 (7)	0.0087 (8)	0.0032 (6)
C3	0.0507 (8)	0.0550 (8)	0.0518 (8)	0.0142 (7)	0.0053 (6)	0.0090 (6)
C4	0.0374 (7)	0.0516 (8)	0.0415 (6)	0.0005 (6)	0.0016 (5)	0.0006 (6)
N1	0.0383 (6)	0.0479 (7)	0.0446 (6)	0.0035 (5)	−0.0003 (5)	0.0035 (5)
N2	0.0429 (6)	0.0485 (7)	0.0554 (7)	0.0013 (5)	−0.0064 (5)	−0.0010 (5)
N3	0.0482 (7)	0.0454 (7)	0.0698 (8)	−0.0023 (5)	−0.0142 (6)	−0.0001 (6)
N4	0.0438 (7)	0.0656 (8)	0.0585 (7)	−0.0012 (6)	−0.0090 (6)	−0.0013 (6)
N5	0.0433 (7)	0.0603 (8)	0.0497 (7)	0.0036 (6)	−0.0017 (5)	0.0039 (5)

Geometric parameters (Å, º)

O1—N5	1.2469 (16)	C3—N1	1.3730 (18)
O2—N5	1.2190 (16)	C4—N1	1.3789 (18)
O3—N5	1.2514 (17)	C4—N3	1.2972 (19)
C1—C2	1.403 (2)	C4—N4	1.3037 (17)
C1—N2	1.3113 (19)	N1—N2	1.3733 (15)
C2—C3	1.342 (2)
N2—C1—C2	112.68 (14)	C3—N1—N2	111.22 (11)
C3—C2—C1	105.36 (14)	N2—N1—C4	119.09 (10)
C2—C3—N1	106.90 (13)	C1—N2—N1	103.84 (11)
N3—C4—N1	118.34 (12)	O1—N5—O3	120.29 (13)
N3—C4—N4	122.09 (14)	O2—N5—O1	120.01 (13)
N4—C4—N1	119.55 (13)	O2—N5—O3	119.70 (13)
C3—N1—C4	129.65 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1^i	0.86	1.92	2.7726 (17)	174
N3—H3B···N2^ii	0.86	2.25	2.9887 (17)	145
N4—H4A···O3^i	0.86	2.10	2.9506 (19)	171
N4—H4B···O3^iii	0.86	2.42	3.2752 (18)	170

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+2, −y+1, −z+1; (iii) x−1, y, z.