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

The title compound C₉H₈N₄OS, crystallizes with two mol­ecules in the asymmetric unit. The crystal structure is stabilized by inter­molecular hydrogen bonds between the protonated N atom of the triazine ring and the carbonyl O atom of an adjacent triazine ring, forming chains running parallel to the a axis.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.143
• Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level C
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         16
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C9 H8 N4 O S

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: APEX2 (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

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

Crystal data

C9H8N4OS	Z = 4
Mr = 220.25	F(000) = 456
Triclinic, P1	Dx = 1.548 Mg m^−3
a = 6.5965 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.0573 (12) Å	Cell parameters from 3497 reflections
c = 21.238 (4) Å	θ = 3.0–30.2°
α = 81.061 (3)°	µ = 0.32 mm^−1
β = 89.307 (4)°	T = 273 K
γ = 75.444 (3)°	Plate, clear colorless?
V = 945.0 (3) Å^3	0.55 × 0.27 × 0.10 mm

Data collection

Bruker Apex II CCD area-detector diffractometer	5336 independent reflections
Radiation source: fine-focus sealed tube	3757 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 30.8°, θmin = 1.9°
Absorption correction: multi-scan Sadabs (Sheldrick, 1996)	h = −7→9
Tmin = 0.845, Tmax = 0.970	k = −10→9
10897 measured reflections	l = −28→29

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.071P)^2 + 0.1411P] where P = (Fo^2 + 2Fc^2)/3
5336 reflections	(Δ/σ)max = 0.002
289 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.26 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
S1A	0.94788 (8)	−0.07777 (9)	0.70696 (2)	0.05222 (17)
S1B	−0.10922 (8)	0.67908 (10)	0.21738 (2)	0.05537 (18)
O1A	0.28032 (19)	0.1681 (2)	0.58355 (6)	0.0465 (3)
O1B	−0.7434 (2)	0.7999 (2)	0.08135 (6)	0.0490 (4)
N1A	0.8927 (2)	0.0702 (3)	0.58453 (7)	0.0399 (4)
H1AA	1.028 (4)	0.060 (3)	0.5833 (10)	0.048*
N2A	0.7922 (2)	0.1589 (2)	0.52907 (7)	0.0385 (3)
N3A	0.5920 (2)	0.0572 (2)	0.63638 (6)	0.0319 (3)
N4A	0.4866 (3)	0.0198 (3)	0.69333 (7)	0.0453 (4)
H4A1	0.561 (4)	−0.119 (4)	0.7083 (11)	0.054*
H4A2	0.368 (4)	0.019 (4)	0.6831 (11)	0.054*
N1B	−0.1327 (2)	0.7066 (3)	0.09250 (7)	0.0423 (4)
H1BA	−0.007 (4)	0.702 (3)	0.0928 (10)	0.051*
N2B	−0.2150 (2)	0.7221 (3)	0.03395 (7)	0.0397 (4)
N3B	−0.4464 (2)	0.7432 (2)	0.14045 (6)	0.0353 (3)
N4B	−0.5668 (3)	0.7405 (3)	0.19564 (8)	0.0467 (4)
H4B1	−0.530 (4)	0.807 (4)	0.2206 (12)	0.056*
H4B2	−0.697 (4)	0.785 (4)	0.1844 (11)	0.056*
C1A	0.8059 (3)	0.0206 (3)	0.64079 (8)	0.0342 (4)
C2A	0.4704 (2)	0.1436 (2)	0.58175 (7)	0.0306 (3)
C3A	0.5893 (2)	0.1971 (2)	0.52563 (7)	0.0293 (3)
C4A	0.4878 (3)	0.2980 (2)	0.46306 (7)	0.0314 (3)
C5A	0.6170 (3)	0.3432 (3)	0.41301 (8)	0.0414 (4)
H5AA	0.7615	0.3082	0.4199	0.050*
C6A	0.5337 (4)	0.4387 (3)	0.35383 (9)	0.0494 (5)
H6AA	0.6219	0.4681	0.3213	0.059*
C7A	0.3192 (4)	0.4908 (3)	0.34283 (10)	0.0503 (5)
H7AA	0.2629	0.5533	0.3028	0.060*
C8A	0.1891 (3)	0.4494 (3)	0.39155 (10)	0.0504 (5)
H8AA	0.0448	0.4859	0.3843	0.060*
C9A	0.2715 (3)	0.3537 (3)	0.45139 (9)	0.0427 (4)
H9AA	0.1820	0.3267	0.4838	0.051*
C1B	−0.2342 (3)	0.7099 (3)	0.14814 (8)	0.0370 (4)
C2B	−0.5526 (3)	0.7648 (3)	0.08255 (8)	0.0333 (3)
C3B	−0.4154 (3)	0.7449 (2)	0.02751 (7)	0.0320 (3)
C4B	−0.4966 (3)	0.7502 (3)	−0.03795 (8)	0.0340 (4)
C5B	−0.7082 (3)	0.7935 (3)	−0.05496 (9)	0.0464 (5)
H5BA	−0.8087	0.8237	−0.0245	0.056*
C6B	−0.7703 (4)	0.7919 (4)	−0.11713 (10)	0.0543 (6)
H6BA	−0.9122	0.8207	−0.1278	0.065*
C7B	−0.6244 (4)	0.7482 (3)	−0.16296 (9)	0.0540 (5)
H7BA	−0.6674	0.7471	−0.2044	0.065*
C8B	−0.4138 (4)	0.7062 (4)	−0.14706 (9)	0.0552 (6)
H8BA	−0.3144	0.6767	−0.1779	0.066*
C9B	−0.3504 (3)	0.7077 (3)	−0.08541 (9)	0.0467 (5)
H9BA	−0.2081	0.6800	−0.0753	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0345 (3)	0.0800 (4)	0.0382 (2)	−0.0130 (2)	−0.00828 (18)	0.0011 (2)
S1B	0.0323 (3)	0.0948 (5)	0.0387 (3)	−0.0158 (3)	−0.00522 (19)	−0.0092 (2)
O1A	0.0223 (6)	0.0718 (10)	0.0449 (7)	−0.0160 (6)	0.0024 (5)	−0.0012 (6)
O1B	0.0235 (6)	0.0817 (11)	0.0441 (7)	−0.0187 (6)	0.0032 (5)	−0.0083 (7)
N1A	0.0193 (7)	0.0591 (10)	0.0382 (7)	−0.0096 (6)	0.0004 (5)	0.0018 (7)
N2A	0.0241 (7)	0.0526 (9)	0.0364 (7)	−0.0095 (6)	0.0021 (5)	−0.0001 (6)
N3A	0.0248 (7)	0.0446 (8)	0.0286 (6)	−0.0118 (6)	0.0039 (5)	−0.0078 (5)
N4A	0.0307 (8)	0.0742 (12)	0.0319 (7)	−0.0170 (8)	0.0074 (6)	−0.0053 (7)
N1B	0.0222 (7)	0.0688 (11)	0.0392 (8)	−0.0165 (7)	0.0028 (6)	−0.0105 (7)
N2B	0.0262 (7)	0.0575 (10)	0.0376 (7)	−0.0139 (7)	0.0039 (6)	−0.0087 (6)
N3B	0.0266 (7)	0.0496 (9)	0.0322 (7)	−0.0149 (6)	0.0044 (5)	−0.0056 (6)
N4B	0.0301 (8)	0.0808 (13)	0.0340 (8)	−0.0212 (8)	0.0086 (6)	−0.0121 (8)
C1A	0.0263 (8)	0.0418 (9)	0.0361 (8)	−0.0107 (7)	0.0002 (6)	−0.0075 (7)
C2A	0.0230 (8)	0.0375 (9)	0.0342 (8)	−0.0114 (6)	0.0018 (6)	−0.0082 (6)
C3A	0.0216 (7)	0.0341 (8)	0.0340 (7)	−0.0092 (6)	0.0021 (6)	−0.0072 (6)
C4A	0.0284 (8)	0.0333 (8)	0.0344 (8)	−0.0102 (6)	0.0005 (6)	−0.0069 (6)
C5A	0.0321 (9)	0.0520 (11)	0.0394 (9)	−0.0124 (8)	0.0021 (7)	−0.0026 (8)
C6A	0.0504 (12)	0.0594 (13)	0.0374 (9)	−0.0163 (10)	0.0024 (8)	−0.0007 (8)
C7A	0.0554 (13)	0.0523 (12)	0.0418 (10)	−0.0149 (10)	−0.0126 (9)	0.0005 (8)
C8A	0.0362 (11)	0.0563 (12)	0.0557 (12)	−0.0119 (9)	−0.0135 (9)	0.0013 (9)
C9A	0.0293 (9)	0.0515 (11)	0.0458 (10)	−0.0115 (8)	−0.0023 (7)	−0.0009 (8)
C1B	0.0269 (8)	0.0485 (10)	0.0373 (8)	−0.0131 (7)	−0.0005 (6)	−0.0062 (7)
C2B	0.0245 (8)	0.0427 (9)	0.0349 (8)	−0.0141 (7)	0.0017 (6)	−0.0035 (6)
C3B	0.0269 (8)	0.0360 (9)	0.0351 (8)	−0.0119 (7)	0.0037 (6)	−0.0048 (6)
C4B	0.0325 (9)	0.0350 (9)	0.0357 (8)	−0.0124 (7)	0.0013 (6)	−0.0029 (6)
C5B	0.0365 (10)	0.0646 (13)	0.0385 (9)	−0.0160 (9)	−0.0007 (7)	−0.0034 (8)
C6B	0.0462 (12)	0.0734 (15)	0.0443 (10)	−0.0230 (11)	−0.0090 (9)	0.0018 (10)
C7B	0.0672 (15)	0.0615 (14)	0.0355 (9)	−0.0240 (11)	−0.0079 (9)	−0.0011 (8)
C8B	0.0593 (14)	0.0695 (14)	0.0371 (10)	−0.0158 (11)	0.0079 (9)	−0.0106 (9)
C9B	0.0387 (11)	0.0609 (13)	0.0410 (9)	−0.0123 (9)	0.0046 (8)	−0.0103 (8)

Geometric parameters (Å, º)

S1A—C1A	1.6541 (17)	C4A—C9A	1.396 (2)
S1B—C1B	1.6520 (18)	C4A—C5A	1.403 (2)
O1A—C2A	1.223 (2)	C5A—C6A	1.380 (3)
O1B—C2B	1.220 (2)	C5A—H5AA	0.9300
N1A—N2A	1.342 (2)	C6A—C7A	1.383 (3)
N1A—C1A	1.353 (2)	C6A—H6AA	0.9300
N1A—H1AA	0.88 (2)	C7A—C8A	1.379 (3)
N2A—C3A	1.298 (2)	C7A—H7AA	0.9300
N3A—C1A	1.371 (2)	C8A—C9A	1.390 (3)
N3A—C2A	1.385 (2)	C8A—H8AA	0.9300
N3A—N4A	1.4102 (19)	C9A—H9AA	0.9300
N4A—H4A1	0.99 (2)	C2B—C3B	1.472 (2)
N4A—H4A2	0.81 (3)	C3B—C4B	1.487 (2)
N1B—N2B	1.341 (2)	C4B—C5B	1.391 (3)
N1B—C1B	1.352 (2)	C4B—C9B	1.401 (3)
N1B—H1BA	0.82 (2)	C5B—C6B	1.390 (3)
N2B—C3B	1.298 (2)	C5B—H5BA	0.9300
N3B—C1B	1.367 (2)	C6B—C7B	1.375 (3)
N3B—C2B	1.391 (2)	C6B—H6BA	0.9300
N3B—N4B	1.408 (2)	C7B—C8B	1.381 (3)
N4B—H4B1	0.84 (3)	C7B—H7BA	0.9300
N4B—H4B2	0.86 (3)	C8B—C9B	1.382 (3)
C2A—C3A	1.471 (2)	C8B—H8BA	0.9300
C3A—C4A	1.486 (2)	C9B—H9BA	0.9300
N2A—N1A—C1A	127.28 (15)	C7A—C6A—H6AA	120.0
N2A—N1A—H1AA	112.8 (14)	C8A—C7A—C6A	119.68 (18)
C1A—N1A—H1AA	119.4 (14)	C8A—C7A—H7AA	120.2
C3A—N2A—N1A	119.21 (15)	C6A—C7A—H7AA	120.2
C1A—N3A—C2A	125.20 (14)	C7A—C8A—C9A	120.72 (19)
C1A—N3A—N4A	117.10 (14)	C7A—C8A—H8AA	119.6
C2A—N3A—N4A	117.45 (14)	C9A—C8A—H8AA	119.6
N3A—N4A—H4A1	100.4 (13)	C8A—C9A—C4A	120.32 (18)
N3A—N4A—H4A2	106.8 (16)	C8A—C9A—H9AA	119.8
H4A1—N4A—H4A2	106 (2)	C4A—C9A—H9AA	119.8
N2B—N1B—C1B	127.67 (16)	N1B—C1B—N3B	113.13 (15)
N2B—N1B—H1BA	113.5 (15)	N1B—C1B—S1B	122.13 (14)
C1B—N1B—H1BA	118.7 (15)	N3B—C1B—S1B	124.74 (13)
C3B—N2B—N1B	118.66 (15)	O1B—C2B—N3B	119.30 (15)
C1B—N3B—C2B	125.18 (14)	O1B—C2B—C3B	126.57 (15)
C1B—N3B—N4B	117.89 (14)	N3B—C2B—C3B	114.12 (14)
C2B—N3B—N4B	116.73 (14)	N2B—C3B—C2B	121.05 (15)
N3B—N4B—H4B1	110.2 (18)	N2B—C3B—C4B	116.39 (15)
N3B—N4B—H4B2	108.5 (15)	C2B—C3B—C4B	122.56 (15)
H4B1—N4B—H4B2	112 (2)	C5B—C4B—C9B	117.93 (17)
N1A—C1A—N3A	113.03 (14)	C5B—C4B—C3B	124.25 (16)
N1A—C1A—S1A	122.47 (13)	C9B—C4B—C3B	117.81 (16)
N3A—C1A—S1A	124.49 (13)	C6B—C5B—C4B	120.46 (19)
O1A—C2A—N3A	119.31 (15)	C6B—C5B—H5BA	119.8
O1A—C2A—C3A	126.09 (15)	C4B—C5B—H5BA	119.8
N3A—C2A—C3A	114.60 (14)	C7B—C6B—C5B	120.8 (2)
N2A—C3A—C2A	120.54 (14)	C7B—C6B—H6BA	119.6
N2A—C3A—C4A	116.44 (14)	C5B—C6B—H6BA	119.6
C2A—C3A—C4A	123.02 (14)	C6B—C7B—C8B	119.58 (19)
C9A—C4A—C5A	117.99 (16)	C6B—C7B—H7BA	120.2
C9A—C4A—C3A	123.98 (15)	C8B—C7B—H7BA	120.2
C5A—C4A—C3A	118.01 (15)	C7B—C8B—C9B	120.1 (2)
C6A—C5A—C4A	121.25 (18)	C7B—C8B—H8BA	120.0
C6A—C5A—H5AA	119.4	C9B—C8B—H8BA	120.0
C4A—C5A—H5AA	119.4	C8B—C9B—C4B	121.2 (2)
C5A—C6A—C7A	120.03 (19)	C8B—C9B—H9BA	119.4
C5A—C6A—H6AA	120.0	C4B—C9B—H9BA	119.4
C1A—N1A—N2A—C3A	−3.3 (3)	C3A—C4A—C9A—C8A	179.37 (18)
C1B—N1B—N2B—C3B	0.7 (3)	N2B—N1B—C1B—N3B	−3.5 (3)
N2A—N1A—C1A—N3A	4.5 (3)	N2B—N1B—C1B—S1B	177.25 (16)
N2A—N1A—C1A—S1A	−176.55 (16)	C2B—N3B—C1B—N1B	2.3 (3)
C2A—N3A—C1A—N1A	−2.7 (3)	N4B—N3B—C1B—N1B	177.11 (17)
N4A—N3A—C1A—N1A	−176.79 (16)	C2B—N3B—C1B—S1B	−178.46 (14)
C2A—N3A—C1A—S1A	178.43 (14)	N4B—N3B—C1B—S1B	−3.7 (3)
N4A—N3A—C1A—S1A	4.3 (2)	C1B—N3B—C2B—O1B	−177.89 (18)
C1A—N3A—C2A—O1A	179.71 (17)	N4B—N3B—C2B—O1B	7.3 (3)
N4A—N3A—C2A—O1A	−6.2 (2)	C1B—N3B—C2B—C3B	1.1 (3)
C1A—N3A—C2A—C3A	−0.1 (2)	N4B—N3B—C2B—C3B	−173.69 (16)
N4A—N3A—C2A—C3A	174.03 (15)	N1B—N2B—C3B—C2B	3.4 (3)
N1A—N2A—C3A—C2A	−0.1 (3)	N1B—N2B—C3B—C4B	−176.77 (16)
N1A—N2A—C3A—C4A	179.21 (16)	O1B—C2B—C3B—N2B	174.76 (19)
O1A—C2A—C3A—N2A	−178.16 (18)	N3B—C2B—C3B—N2B	−4.2 (2)
N3A—C2A—C3A—N2A	1.6 (2)	O1B—C2B—C3B—C4B	−5.0 (3)
O1A—C2A—C3A—C4A	2.6 (3)	N3B—C2B—C3B—C4B	176.01 (15)
N3A—C2A—C3A—C4A	−177.69 (15)	N2B—C3B—C4B—C5B	−173.19 (18)
N2A—C3A—C4A—C9A	−178.59 (17)	C2B—C3B—C4B—C5B	6.6 (3)
C2A—C3A—C4A—C9A	0.7 (3)	N2B—C3B—C4B—C9B	7.2 (2)
N2A—C3A—C4A—C5A	0.2 (2)	C2B—C3B—C4B—C9B	−172.97 (17)
C2A—C3A—C4A—C5A	179.53 (16)	C9B—C4B—C5B—C6B	0.7 (3)
C9A—C4A—C5A—C6A	−0.4 (3)	C3B—C4B—C5B—C6B	−178.89 (18)
C3A—C4A—C5A—C6A	−179.27 (18)	C4B—C5B—C6B—C7B	−0.2 (3)
C4A—C5A—C6A—C7A	−0.4 (3)	C5B—C6B—C7B—C8B	−0.2 (4)
C5A—C6A—C7A—C8A	1.0 (3)	C6B—C7B—C8B—C9B	0.1 (4)
C6A—C7A—C8A—C9A	−0.8 (3)	C7B—C8B—C9B—C4B	0.4 (3)
C7A—C8A—C9A—C4A	0.0 (3)	C5B—C4B—C9B—C8B	−0.8 (3)
C5A—C4A—C9A—C8A	0.6 (3)	C3B—C4B—C9B—C8B	178.80 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AA···O1A^i	0.88 (2)	2.00 (2)	2.810 (2)	153 (2)
N4A—H4A2···O1A	0.81 (3)	2.22 (2)	2.643 (2)	112 (2)
N1B—H1BA···O1B^i	0.82 (2)	2.02 (2)	2.806 (2)	158 (2)
N4B—H4B1···N4A^ii	0.84 (3)	2.41 (3)	3.228 (3)	167 (2)
N4B—H4B2···O1B	0.86 (3)	2.20 (2)	2.633 (2)	111.3 (19)

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