6-Methyl-7H-1,2,4-triazolo[4,3-b][1,2,4]triazepin-8(9H)-thione

In the mol­ecule of the title compound, C₆H₇N₅S, the triazole ring is planar, while the triazepine ring displays a boat conformation. The dihedral angle between the mean plane through the triazole and triazepine rings is 18.48 (8)°. In the crystal, mol­ecules are linked into centrosymmetric dimers by N—H...N hydrogen bonds via eight-membered {...HNCN}₂ synthons. Supra­molecular layers in the ab plane are sustained by C—H...N and π–π inter­actions [inter-centroid separation between triazole rings = 3.2880 (16) Å]. Connections along the c axis occur between S atoms [S...S = 3.5972 (16) Å].

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.119
• Data-to-parameter ratio = 20.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full value Low .      0.951 Note

Alert level C
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         44 Ang3
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         76 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         60 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT933_ALERT_2_G Number of OMIT records in Embedded RES .........          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           3 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2008) and publCIF (Westrip, 2010).

6-Methyl-7H-1,2,4-triazolo[4,3-b][1,2,4]triazepin-8(9H)-thione

Crystal data

C6H7N5S	Z = 2
Mr = 181.23	F(000) = 188
Triclinic, P1	Dx = 1.392 Mg m^−3
a = 6.238 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.234 (3) Å	Cell parameters from 2287 reflections
c = 10.887 (4) Å	θ = 3.2–29.6°
α = 103.331 (15)°	µ = 0.33 mm^−1
β = 92.329 (16)°	T = 296 K
γ = 113.846 (15)°	Block, colourless
V = 432.3 (3) Å^3	0.35 × 0.30 × 0.26 mm

Data collection

Bruker X8 APEX diffractometer	2287 independent reflections
Radiation source: fine-focus sealed tube	2038 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 29.6°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −8→8
Tmin = 0.644, Tmax = 0.747	k = −10→10
10195 measured reflections	l = −14→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.119	w = 1/[σ^2(Fo^2) + (0.0613P)^2 + 0.1769P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2287 reflections	Δρmax = 0.47 e Å^−3
110 parameters	Δρmin = −0.38 e Å^−3

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	0.5444 (3)	0.3425 (2)	0.76025 (13)	0.0284 (3)
C2	0.3456 (3)	0.4034 (2)	0.79409 (13)	0.0306 (3)
H2A	0.1951	0.2807	0.7656	0.037*
H2B	0.3627	0.4553	0.8861	0.037*
C3	0.3466 (3)	0.5699 (2)	0.73291 (14)	0.0318 (3)
C4	0.4105 (4)	0.7857 (3)	0.81648 (19)	0.0507 (5)
H4A	0.5692	0.8425	0.8607	0.076*
H4B	0.3025	0.7790	0.8775	0.076*
H4C	0.4007	0.8741	0.7650	0.076*
C5	0.1097 (3)	0.2566 (2)	0.41943 (15)	0.0344 (3)
H5	0.0219	0.3170	0.3869	0.041*
C6	0.3465 (2)	0.2043 (2)	0.54244 (13)	0.0253 (3)
N1	0.2954 (2)	0.54000 (18)	0.61292 (13)	0.0324 (3)
N2	0.2479 (2)	0.33992 (17)	0.53619 (11)	0.0275 (2)
N3	0.1165 (2)	0.0823 (2)	0.35948 (12)	0.0345 (3)
N4	0.2688 (2)	0.04725 (18)	0.43825 (11)	0.0295 (3)
N5	0.5193 (2)	0.23657 (19)	0.63695 (11)	0.0290 (3)
H5N	0.6036	0.1688	0.6148	0.035*
S1	0.77311 (8)	0.39546 (8)	0.86328 (4)	0.04839 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0301 (7)	0.0290 (6)	0.0273 (6)	0.0153 (5)	0.0046 (5)	0.0045 (5)
C2	0.0326 (7)	0.0352 (7)	0.0271 (6)	0.0192 (6)	0.0079 (5)	0.0045 (5)
C3	0.0310 (7)	0.0285 (6)	0.0360 (7)	0.0160 (5)	0.0074 (6)	0.0020 (5)
C4	0.0658 (12)	0.0320 (8)	0.0477 (10)	0.0219 (8)	0.0097 (9)	−0.0037 (7)
C5	0.0345 (7)	0.0372 (7)	0.0336 (7)	0.0197 (6)	−0.0010 (6)	0.0059 (6)
C6	0.0259 (6)	0.0253 (6)	0.0271 (6)	0.0140 (5)	0.0056 (5)	0.0051 (5)
N1	0.0369 (6)	0.0246 (5)	0.0380 (7)	0.0176 (5)	0.0062 (5)	0.0042 (4)
N2	0.0292 (6)	0.0257 (5)	0.0294 (6)	0.0155 (4)	0.0027 (4)	0.0041 (4)
N3	0.0334 (6)	0.0378 (6)	0.0308 (6)	0.0178 (5)	−0.0017 (5)	0.0024 (5)
N4	0.0314 (6)	0.0287 (5)	0.0280 (6)	0.0158 (5)	0.0022 (4)	0.0017 (4)
N5	0.0317 (6)	0.0332 (6)	0.0261 (5)	0.0212 (5)	0.0029 (4)	0.0015 (4)
S1	0.0423 (3)	0.0695 (3)	0.0326 (2)	0.0328 (2)	−0.00534 (17)	−0.00263 (19)

Geometric parameters (Å, º)

C1—N5	1.3509 (18)	C4—H4C	0.9600
C1—C2	1.5072 (19)	C5—N3	1.298 (2)
C1—S1	1.6343 (16)	C5—N2	1.3636 (19)
C2—C3	1.503 (2)	C5—H5	0.9300
C2—H2A	0.9700	C6—N4	1.3144 (17)
C2—H2B	0.9700	C6—N2	1.3647 (17)
C3—N1	1.279 (2)	C6—N5	1.3675 (18)
C3—C4	1.495 (2)	N1—N2	1.3986 (16)
C4—H4A	0.9600	N3—N4	1.3898 (18)
C4—H4B	0.9600	N5—H5N	0.8599
N5—C1—C2	114.93 (12)	H4B—C4—H4C	109.5
N5—C1—S1	121.53 (11)	N3—C5—N2	111.33 (13)
C2—C1—S1	123.54 (10)	N3—C5—H5	124.3
C3—C2—C1	111.00 (12)	N2—C5—H5	124.3
C3—C2—H2A	109.4	N4—C6—N2	110.24 (12)
C1—C2—H2A	109.4	N4—C6—N5	124.33 (12)
C3—C2—H2B	109.4	N2—C6—N5	125.12 (12)
C1—C2—H2B	109.4	C3—N1—N2	115.92 (12)
H2A—C2—H2B	108.0	C5—N2—C6	104.35 (11)
N1—C3—C4	117.00 (15)	C5—N2—N1	122.64 (12)
N1—C3—C2	124.37 (12)	C6—N2—N1	132.08 (12)
C4—C3—C2	118.62 (15)	C5—N3—N4	106.88 (12)
C3—C4—H4A	109.5	C6—N4—N3	107.19 (12)
C3—C4—H4B	109.5	C1—N5—C6	125.05 (12)
H4A—C4—H4B	109.5	C1—N5—H5N	120.1
C3—C4—H4C	109.5	C6—N5—H5N	114.4
H4A—C4—H4C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···N4^i	0.86	2.01	2.8530 (18)	167
C2—H2A···N3^ii	0.97	2.56	3.487 (2)	161
C5—H5···N1^iii	0.93	2.58	3.442 (2)	155

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