Crystal structure, thermal behaviour and detonation characterization of bis­(4,5-di­amino-1,2,4-tria­zol-3-yl)methane monohydrate

Bis(4,5-di­amino-1,2,4-triazol-3-yl)methane monohydrate (BDATZM·H₂O or C₅H₁₀N₁₀·H₂O) was synthesized and its crystal structure characterized by single-crystal X-ray diffraction; it belongs to the space group P (triclinic) with Z = 2. The structure of BDATZM·H₂O can be described as a two-dimensional ladder plane with extensive hydrogen bonding and no disorder. The thermal behaviour was studied under non-isothermal conditions by differential scanning calorimetry (DSC) and thermogravimetric/differential thermogravimetric (TG/DTG) methods. The detonation velocity (D) and detonation pressure (P) of BDATZM were estimated using the nitro­gen equivalent equation according to the experimental density. A com­parison between BDATZM·H₂O and bis­(5-amino-1,2,4-triazol-3-yl)methane (BATZM) was made to determine the effect of the amino group; the results suggest that the amino group increases the hydro­philicity, space utilization and energy, and decreases the thermal stability and symmetry of the resulting com­pound.

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Bis(4,5-diamino-1,2,4-triazol-3-yl)methane monohydrate

Crystal data

C5H10N10·H2O	Z = 2
Mr = 228.25	F(000) = 240
Triclinic, P1	Dx = 1.580 Mg m^−3
a = 5.4364 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 5.6202 (11) Å	Cell parameters from 1383 reflections
c = 15.844 (3) Å	θ = 2.6–28.0°
α = 83.623 (3)°	µ = 0.12 mm^−1
β = 87.617 (3)°	T = 296 K
γ = 86.146 (3)°	Rodlike, colourless
V = 479.71 (16) Å^3	0.34 × 0.28 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer	1522 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.011
Absorption correction: multi-scan (SADABS; Bruker, 2009)	θmax = 25.1°, θmin = 2.6°
Tmin = 0.960, Tmax = 0.982	h = −5→6
2421 measured reflections	k = −6→6
1698 independent reflections	l = −18→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	All H-atom parameters refined
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.0439P)^2 + 0.179P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1698 reflections	Δρmax = 0.17 e Å^−3
194 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.107 (8)

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
N3	0.4877 (2)	0.6949 (2)	0.37479 (8)	0.0284 (3)
N8	0.4006 (2)	0.4532 (2)	0.12692 (8)	0.0292 (3)
N1	0.1762 (3)	0.4668 (3)	0.40038 (9)	0.0411 (4)
N7	0.7210 (3)	0.2065 (2)	0.15392 (9)	0.0388 (4)
N10	0.2307 (3)	0.6532 (3)	0.12384 (11)	0.0408 (4)
N5	0.6456 (3)	0.8754 (3)	0.38523 (11)	0.0448 (4)
N6	0.5896 (3)	0.1227 (2)	0.08966 (9)	0.0383 (4)
N2	0.3076 (3)	0.4056 (3)	0.32649 (8)	0.0390 (4)
C5	0.3981 (3)	0.2755 (3)	0.07553 (9)	0.0308 (4)
C2	0.4888 (3)	0.5453 (3)	0.31288 (9)	0.0293 (4)
N9	0.2256 (3)	0.2702 (3)	0.01670 (10)	0.0425 (4)
C4	0.6046 (3)	0.4023 (3)	0.17430 (9)	0.0305 (4)
N4	0.2268 (3)	0.7560 (3)	0.49553 (10)	0.0484 (4)
C1	0.2906 (3)	0.6410 (3)	0.42740 (9)	0.0318 (4)
C3	0.6737 (3)	0.5516 (3)	0.24052 (10)	0.0339 (4)
O1	0.1062 (3)	−0.0044 (2)	0.26006 (9)	0.0502 (4)
H3A	0.832 (3)	0.492 (3)	0.2612 (10)	0.032 (4)*
H3B	0.685 (3)	0.718 (4)	0.2154 (12)	0.045 (5)*
H4A	0.103 (4)	0.708 (4)	0.5279 (13)	0.050 (6)*
H9A	0.248 (4)	0.148 (4)	−0.0139 (13)	0.051 (6)*
H10B	0.187 (4)	0.683 (4)	0.1761 (16)	0.074 (7)*
H4B	0.308 (4)	0.875 (4)	0.5077 (14)	0.063 (6)*
H1A	0.171 (5)	0.122 (5)	0.2784 (15)	0.075 (7)*
H1B	−0.012 (5)	0.059 (4)	0.2209 (16)	0.079 (8)*
H9B	0.079 (5)	0.327 (4)	0.0279 (15)	0.070 (7)*
H10A	0.316 (5)	0.782 (5)	0.1007 (16)	0.081 (8)*
H5B	0.797 (5)	0.819 (4)	0.3807 (15)	0.075 (8)*
H5A	0.622 (6)	0.995 (6)	0.344 (2)	0.122 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N3	0.0293 (6)	0.0291 (7)	0.0289 (6)	−0.0081 (5)	0.0001 (5)	−0.0088 (5)
N8	0.0327 (7)	0.0264 (6)	0.0292 (7)	−0.0026 (5)	0.0021 (5)	−0.0070 (5)
N1	0.0460 (8)	0.0476 (8)	0.0336 (7)	−0.0205 (7)	0.0095 (6)	−0.0153 (6)
N7	0.0399 (8)	0.0411 (8)	0.0379 (8)	0.0022 (6)	−0.0061 (6)	−0.0166 (6)
N10	0.0445 (9)	0.0331 (8)	0.0450 (9)	0.0048 (7)	−0.0003 (7)	−0.0094 (7)
N5	0.0426 (9)	0.0477 (9)	0.0502 (10)	−0.0233 (7)	0.0070 (7)	−0.0232 (8)
N6	0.0431 (8)	0.0372 (8)	0.0372 (8)	0.0018 (6)	−0.0056 (6)	−0.0163 (6)
N2	0.0453 (8)	0.0417 (8)	0.0336 (7)	−0.0189 (6)	0.0074 (6)	−0.0142 (6)
C5	0.0361 (8)	0.0307 (8)	0.0262 (8)	−0.0049 (7)	0.0020 (6)	−0.0059 (6)
C2	0.0332 (8)	0.0278 (7)	0.0284 (8)	−0.0059 (6)	−0.0022 (6)	−0.0070 (6)
N9	0.0435 (9)	0.0482 (9)	0.0385 (8)	−0.0007 (7)	−0.0063 (7)	−0.0162 (7)
C4	0.0317 (8)	0.0318 (8)	0.0289 (8)	−0.0053 (6)	0.0030 (6)	−0.0070 (6)
N4	0.0509 (9)	0.0557 (10)	0.0444 (9)	−0.0241 (8)	0.0177 (7)	−0.0265 (7)
C1	0.0330 (8)	0.0347 (8)	0.0289 (8)	−0.0075 (7)	0.0016 (6)	−0.0066 (6)
C3	0.0335 (9)	0.0372 (9)	0.0336 (8)	−0.0089 (7)	0.0019 (7)	−0.0118 (7)
O1	0.0561 (8)	0.0355 (7)	0.0608 (9)	−0.0017 (6)	−0.0169 (7)	−0.0092 (6)

Geometric parameters (Å, º)

N3—C1	1.3593 (19)	N6—C5	1.314 (2)
N3—C2	1.3607 (18)	N2—C2	1.2966 (19)
N3—N5	1.3997 (18)	C5—N9	1.354 (2)
N8—C5	1.3576 (19)	C2—C3	1.492 (2)
N8—C4	1.362 (2)	N9—H9A	0.88 (2)
N8—N10	1.4040 (19)	N9—H9B	0.86 (3)
N1—C1	1.314 (2)	C4—C3	1.489 (2)
N1—N2	1.4094 (19)	N4—C1	1.341 (2)
N7—C4	1.297 (2)	N4—H4A	0.87 (2)
N7—N6	1.4078 (19)	N4—H4B	0.87 (2)
N10—H10B	0.88 (3)	C3—H3A	0.957 (18)
N10—H10A	0.92 (3)	C3—H3B	0.982 (19)
N5—H5B	0.86 (3)	O1—H1A	0.89 (3)
N5—H5A	0.89 (3)	O1—H1B	0.94 (3)
C1—N3—C2	105.99 (12)	N3—C2—C3	122.99 (13)
C1—N3—N5	124.19 (12)	C5—N9—H9A	114.2 (13)
C2—N3—N5	129.80 (13)	C5—N9—H9B	117.9 (16)
C5—N8—C4	106.00 (12)	H9A—N9—H9B	120 (2)
C5—N8—N10	124.31 (13)	N7—C4—N8	109.98 (13)
C4—N8—N10	129.53 (13)	N7—C4—C3	126.62 (14)
C1—N1—N2	106.37 (13)	N8—C4—C3	123.39 (13)
C4—N7—N6	107.58 (13)	C1—N4—H4A	118.4 (13)
N8—N10—H10B	109.4 (16)	C1—N4—H4B	121.1 (15)
N8—N10—H10A	106.1 (16)	H4A—N4—H4B	121 (2)
H10B—N10—H10A	106 (2)	N1—C1—N4	126.74 (15)
N3—N5—H5B	109.2 (16)	N1—C1—N3	110.01 (13)
N3—N5—H5A	109 (2)	N4—C1—N3	123.25 (14)
H5B—N5—H5A	108 (3)	C4—C3—C2	111.50 (13)
C5—N6—N7	106.44 (12)	C4—C3—H3A	108.8 (10)
C2—N2—N1	107.62 (12)	C2—C3—H3A	109.3 (10)
N6—C5—N9	126.88 (15)	C4—C3—H3B	109.5 (11)
N6—C5—N8	109.99 (13)	C2—C3—H3B	108.9 (11)
N9—C5—N8	123.07 (15)	H3A—C3—H3B	108.8 (14)
N2—C2—N3	110.01 (13)	H1A—O1—H1B	106 (2)
N2—C2—C3	126.99 (13)
C4—N7—N6—C5	−0.31 (18)	N6—N7—C4—C3	178.91 (14)
C1—N1—N2—C2	−0.66 (18)	C5—N8—C4—N7	−0.05 (17)
N7—N6—C5—N9	177.54 (16)	N10—N8—C4—N7	−175.58 (15)
N7—N6—C5—N8	0.29 (17)	C5—N8—C4—C3	−178.79 (14)
C4—N8—C5—N6	−0.16 (17)	N10—N8—C4—C3	5.7 (2)
N10—N8—C5—N6	175.67 (14)	N2—N1—C1—N4	179.14 (17)
C4—N8—C5—N9	−177.53 (15)	N2—N1—C1—N3	0.13 (18)
N10—N8—C5—N9	−1.7 (2)	C2—N3—C1—N1	0.41 (18)
N1—N2—C2—N3	0.93 (18)	N5—N3—C1—N1	178.92 (16)
N1—N2—C2—C3	−178.11 (16)	C2—N3—C1—N4	−178.64 (16)
C1—N3—C2—N2	−0.85 (17)	N5—N3—C1—N4	−0.1 (3)
N5—N3—C2—N2	−179.24 (17)	N7—C4—C3—C2	−113.06 (18)
C1—N3—C2—C3	178.24 (14)	N8—C4—C3—C2	65.5 (2)
N5—N3—C2—C3	−0.1 (3)	N2—C2—C3—C4	9.6 (2)
N6—N7—C4—N8	0.22 (18)	N3—C2—C3—C4	−169.34 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2	0.89 (3)	2.04 (3)	2.9308 (19)	177 (2)
O1—H1B···N7^i	0.94 (3)	1.92 (3)	2.852 (2)	172 (2)
N4—H4A···N1^ii	0.87 (2)	2.09 (2)	2.949 (2)	170.1 (18)
N9—H9A···N6^iii	0.88 (2)	2.16 (2)	3.018 (2)	163.6 (18)
N4—H4B···N5^iv	0.87 (2)	2.35 (2)	3.084 (2)	142.4 (19)
N10—H10A···N6^v	0.92 (3)	2.49 (3)	3.369 (2)	160 (2)
N10—H10B···O1^v	0.88 (3)	2.33 (2)	3.073 (2)	142 (2)

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