4-Amino-6-tert-butyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one

In the title compound, C₇H₁₂N₄OS, the triazine ring is planar. The crystal structure is stabilized by inter­molecular N—H...O hydrogen bonds which link the mol­ecules into chains running along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.115
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   C1      ..       5.59 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

4-amino-6-tert-butyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one

Crystal data

C7H12N4OS	F(000) = 424
Mr = 200.27	Dx = 1.308 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6656 reflections
a = 12.5196 (8) Å	θ = 3.0–27.9°
b = 6.9535 (4) Å	µ = 0.29 mm^−1
c = 12.5987 (8) Å	T = 273 K
β = 112.039 (1)°	Block, colorless
V = 1016.64 (11) Å^3	0.21 × 0.17 × 0.09 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1640 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
Graphite monochromator	θmax = 25.0°, θmin = 3.3°
ω scan	h = −14→14
9276 measured reflections	k = −8→8
1780 independent reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0662P)^2 + 0.2933P] where P = (Fo^2 + 2Fc^2)/3
1780 reflections	(Δ/σ)max < 0.001
121 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
C1	−0.00561 (16)	0.2735 (2)	0.54361 (14)	0.0451 (4)
C2	0.11100 (14)	0.3524 (2)	0.74142 (13)	0.0441 (4)
C3	0.21126 (15)	0.3016 (2)	0.71497 (14)	0.0464 (4)
C4	0.33206 (16)	0.3196 (3)	0.80548 (16)	0.0584 (5)
C5	0.3522 (2)	0.5249 (4)	0.8516 (2)	0.0798 (7)
H5A	0.3327	0.6137	0.7888	0.120*
H5B	0.4318	0.5407	0.9001	0.120*
H5C	0.3048	0.5495	0.8948	0.120*
C6	0.3473 (2)	0.1766 (4)	0.9032 (2)	0.0845 (7)
H6A	0.2939	0.2075	0.9391	0.127*
H6B	0.4246	0.1847	0.9587	0.127*
H6C	0.3327	0.0485	0.8729	0.127*
C7	0.4203 (2)	0.2737 (5)	0.7519 (2)	0.0891 (8)
H7A	0.4077	0.1455	0.7214	0.134*
H7B	0.4966	0.2834	0.8092	0.134*
H7C	0.4119	0.3635	0.6913	0.134*
N1	0.09438 (14)	0.2328 (2)	0.53334 (13)	0.0509 (4)
H1	0.0901	0.1951	0.4668	0.061*
N2	0.00669 (12)	0.33150 (18)	0.65149 (11)	0.0437 (3)
N3	0.20057 (14)	0.2436 (2)	0.61441 (13)	0.0511 (4)
N4	−0.09099 (13)	0.3921 (2)	0.67116 (14)	0.0590 (4)
H4A	−0.1573	0.3925	0.6160	0.071*
H4B	−0.0846	0.4289	0.7384	0.071*
O1	0.11271 (11)	0.40992 (19)	0.83389 (9)	0.0550 (3)
S1	−0.13213 (4)	0.25524 (7)	0.43523 (4)	0.0578 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0621 (11)	0.0325 (8)	0.0396 (9)	−0.0029 (7)	0.0178 (8)	0.0044 (6)
C2	0.0568 (10)	0.0372 (8)	0.0388 (8)	−0.0017 (7)	0.0183 (7)	0.0042 (6)
C3	0.0554 (10)	0.0423 (8)	0.0418 (9)	−0.0011 (7)	0.0188 (7)	0.0015 (7)
C4	0.0539 (10)	0.0671 (12)	0.0500 (10)	−0.0022 (9)	0.0148 (8)	−0.0006 (9)
C5	0.0689 (13)	0.0801 (15)	0.0730 (14)	−0.0160 (12)	0.0067 (11)	−0.0136 (12)
C6	0.0666 (13)	0.0991 (19)	0.0720 (14)	0.0067 (13)	0.0077 (11)	0.0267 (14)
C7	0.0550 (13)	0.124 (2)	0.0869 (18)	0.0003 (13)	0.0249 (12)	−0.0124 (15)
N1	0.0626 (9)	0.0525 (9)	0.0380 (8)	−0.0020 (7)	0.0193 (7)	−0.0071 (6)
N2	0.0530 (8)	0.0396 (7)	0.0401 (7)	0.0003 (6)	0.0194 (6)	0.0037 (6)
N3	0.0577 (9)	0.0502 (8)	0.0459 (8)	−0.0001 (6)	0.0200 (7)	−0.0042 (6)
N4	0.0541 (9)	0.0721 (11)	0.0536 (9)	0.0093 (7)	0.0232 (7)	0.0011 (7)
O1	0.0718 (8)	0.0577 (7)	0.0386 (6)	−0.0011 (6)	0.0242 (6)	−0.0030 (5)
S1	0.0623 (4)	0.0558 (3)	0.0448 (3)	−0.0065 (2)	0.0080 (2)	0.00531 (18)

Geometric parameters (Å, º)

C1—N1	1.336 (3)	C5—H5C	0.9600
C1—N2	1.370 (2)	C6—H6A	0.9600
C1—S1	1.6633 (18)	C6—H6B	0.9600
C2—O1	1.2244 (19)	C6—H6C	0.9600
C2—N2	1.378 (2)	C7—H7A	0.9600
C2—C3	1.458 (2)	C7—H7B	0.9600
C3—N3	1.288 (2)	C7—H7C	0.9600
C3—C4	1.520 (2)	N1—N3	1.341 (2)
C4—C5	1.526 (3)	N1—H1	0.8600
C4—C7	1.529 (3)	N2—N4	1.401 (2)
C4—C6	1.538 (3)	N4—H4A	0.8600
C5—H5A	0.9600	N4—H4B	0.8600
C5—H5B	0.9600
N1—C1—N2	113.45 (15)	C4—C6—H6B	109.5
N1—C1—S1	122.85 (13)	H6A—C6—H6B	109.5
N2—C1—S1	123.70 (14)	C4—C6—H6C	109.5
O1—C2—N2	119.30 (15)	H6A—C6—H6C	109.5
O1—C2—C3	125.98 (15)	H6B—C6—H6C	109.5
N2—C2—C3	114.72 (14)	C4—C7—H7A	109.5
N3—C3—C2	121.34 (16)	C4—C7—H7B	109.5
N3—C3—C4	118.08 (16)	H7A—C7—H7B	109.5
C2—C3—C4	120.56 (14)	C4—C7—H7C	109.5
C3—C4—C5	109.79 (16)	H7A—C7—H7C	109.5
C3—C4—C7	109.38 (16)	H7B—C7—H7C	109.5
C5—C4—C7	108.6 (2)	C1—N1—N3	127.70 (15)
C3—C4—C6	109.68 (17)	C1—N1—H1	116.2
C5—C4—C6	110.31 (19)	N3—N1—H1	116.2
C7—C4—C6	109.0 (2)	C1—N2—C2	124.45 (14)
C4—C5—H5A	109.5	C1—N2—N4	118.92 (14)
C4—C5—H5B	109.5	C2—N2—N4	116.34 (13)
H5A—C5—H5B	109.5	C3—N3—N1	118.32 (15)
C4—C5—H5C	109.5	N2—N4—H4A	120.0
H5A—C5—H5C	109.5	N2—N4—H4B	120.0
H5B—C5—H5C	109.5	H4A—N4—H4B	120.0
C4—C6—H6A	109.5
O1—C2—C3—N3	−179.47 (16)	N1—C1—N2—C2	1.8 (2)
N2—C2—C3—N3	0.5 (2)	S1—C1—N2—C2	−178.18 (12)
O1—C2—C3—C4	−0.6 (3)	N1—C1—N2—N4	175.30 (14)
N2—C2—C3—C4	179.31 (15)	S1—C1—N2—N4	−4.7 (2)
N3—C3—C4—C5	122.77 (19)	O1—C2—N2—C1	178.12 (15)
C2—C3—C4—C5	−56.1 (2)	C3—C2—N2—C1	−1.8 (2)
N3—C3—C4—C7	3.7 (3)	O1—C2—N2—N4	4.4 (2)
C2—C3—C4—C7	−175.22 (18)	C3—C2—N2—N4	−175.51 (14)
N3—C3—C4—C6	−115.9 (2)	C2—C3—N3—N1	0.8 (2)
C2—C3—C4—C6	65.3 (2)	C4—C3—N3—N1	−178.10 (15)
N2—C1—N1—N3	−0.4 (2)	C1—N1—N3—C3	−0.9 (3)
S1—C1—N1—N3	179.58 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.86	1.94	2.790 (2)	168
N4—H4B···O1	0.86	2.31	2.607 (2)	100
N4—H4A···S1	0.86	2.59	2.976 (2)	108

Symmetry code: (i) x, −y+1/2, z−1/2.