1-Benzoyl-2-thio-biuret.

IN THE TITLE COMPOUND [SYSTEMATIC NAME: N-(carbamoyl-carb-a-mo-thio-yl)benzamide], C(9)H(9)N(3)O(2)S, the benzoyl and terminal urea fragments adopt cisoid and transoid conformations, respectively, with respect to the S atom. The benzoyl and thio-biuret groups are almost coplanar, making a dihedral angle of 8.48 (5)°. The mol-ecular structure is stabilized by an intra-molecular N-H⋯O hydrogen bond. In the crystal, N-H⋯O and N-H⋯S hydrogen bonds link the mol-ecules into a sheet parallel to the bc plane.

Related literature

For structures and reactivity of thia­diazole derivatives, see: Cho et al. (1991a ▶,b ▶, 1996 ▶); Parkanyi et al. (1989 ▶). For the biological activity of thia­diazole derivatives, see: Piskala et al. (2004 ▶); Castro et al. (2008 ▶).

Experimental

Crystal data

C9H9N3O2S

M = 223.25

Monoclinic,

a = 10.4583 (3) Å

b = 12.8103 (4) Å

c = 16.1830 (5) Å

β = 106.693 (1)°

V = 2076.73 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.29 × 0.24 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.911, T max = 0.934

7908 measured reflections

1866 independent reflections

1369 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.114

S = 1.09

1866 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.48 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000621/is5045sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000621/is5045Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000621/is5045Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H9N3O2S	F(000) = 928
Mr = 223.25	Dx = 1.428 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2609 reflections
a = 10.4583 (3) Å	θ = 3.2–28.5°
b = 12.8103 (4) Å	µ = 0.30 mm−1
c = 16.1830 (5) Å	T = 296 K
β = 106.693 (1)°	Block, yellow
V = 2076.73 (11) Å3	0.29 × 0.24 × 0.21 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	1369 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→8
Tmin = 0.911, Tmax = 0.934	k = −13→15
7908 measured reflections	l = −19→10
1866 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0586P)2 + 0.3051P] where P = (Fo2 + 2Fc2)/3
1866 reflections	(Δ/σ)max < 0.001
152 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.61686 (19)	0.18189 (16)	0.04253 (11)	0.0448 (5)
C2	0.5827 (2)	0.28638 (18)	0.03339 (13)	0.0552 (6)
H2	0.5944	0.3279	0.0822	0.066*
C3	0.5314 (2)	0.3297 (2)	−0.04751 (14)	0.0660 (7)
H3	0.5089	0.4001	−0.053	0.079*
C4	0.5136 (2)	0.2690 (2)	−0.11972 (13)	0.0667 (7)
H4	0.4788	0.2983	−0.1742	0.08*
C5	0.5469 (2)	0.1655 (2)	−0.11173 (13)	0.0674 (7)
H5	0.5345	0.1247	−0.1609	0.081*
C6	0.5988 (2)	0.12116 (19)	−0.03144 (12)	0.0587 (6)
H6	0.6217	0.0508	−0.0266	0.07*
C7	0.6705 (2)	0.14132 (16)	0.13236 (11)	0.0470 (5)
O8	0.67319 (17)	0.19421 (11)	0.19501 (8)	0.0635 (5)
N9	0.71681 (18)	0.03965 (14)	0.13835 (10)	0.0505 (5)
H9	0.718 (2)	0.0044 (17)	0.0909 (16)	0.069 (7)*
C10	0.7608 (2)	−0.02204 (16)	0.21000 (12)	0.0483 (5)
S11	0.77062 (8)	0.00861 (5)	0.31016 (3)	0.0797 (3)
N12	0.79787 (18)	−0.12067 (14)	0.19313 (10)	0.0521 (5)
H12	0.8182 (19)	−0.1644 (17)	0.2370 (13)	0.048 (6)*
C13	0.7888 (2)	−0.16766 (17)	0.11369 (12)	0.0487 (5)
O14	0.75791 (17)	−0.11737 (11)	0.04566 (8)	0.0623 (5)
N15	0.8183 (2)	−0.26820 (15)	0.11896 (13)	0.0567 (5)
H15A	0.821 (2)	−0.307 (2)	0.1667 (17)	0.079 (8)*
H15B	0.799 (2)	−0.3006 (19)	0.0700 (16)	0.073 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0499 (12)	0.0499 (13)	0.0359 (9)	−0.0032 (9)	0.0143 (8)	−0.0002 (8)
C2	0.0676 (14)	0.0537 (14)	0.0420 (10)	0.0019 (11)	0.0121 (10)	0.0022 (9)
C3	0.0755 (16)	0.0629 (16)	0.0553 (13)	0.0088 (12)	0.0120 (11)	0.0133 (11)
C4	0.0681 (15)	0.089 (2)	0.0405 (11)	0.0116 (14)	0.0108 (10)	0.0141 (11)
C5	0.0719 (15)	0.091 (2)	0.0353 (10)	0.0112 (14)	0.0090 (10)	−0.0051 (11)
C6	0.0728 (14)	0.0609 (14)	0.0390 (10)	0.0069 (11)	0.0106 (10)	−0.0048 (9)
C7	0.0595 (12)	0.0436 (12)	0.0370 (10)	−0.0049 (9)	0.0123 (9)	−0.0008 (8)
O8	0.1056 (13)	0.0474 (9)	0.0352 (7)	0.0069 (8)	0.0168 (7)	−0.0053 (6)
N9	0.0797 (13)	0.0404 (11)	0.0314 (8)	−0.0001 (9)	0.0160 (8)	−0.0016 (7)
C10	0.0670 (13)	0.0382 (12)	0.0379 (10)	−0.0111 (9)	0.0122 (9)	−0.0014 (8)
S11	0.1564 (8)	0.0453 (4)	0.0330 (3)	0.0008 (4)	0.0199 (3)	−0.0030 (2)
N12	0.0813 (13)	0.0401 (10)	0.0338 (8)	−0.0013 (9)	0.0148 (8)	0.0025 (7)
C13	0.0654 (13)	0.0445 (13)	0.0395 (10)	0.0004 (10)	0.0206 (9)	−0.0001 (8)
O14	0.1069 (13)	0.0474 (9)	0.0381 (7)	0.0104 (8)	0.0296 (7)	0.0046 (6)
N15	0.0886 (14)	0.0447 (12)	0.0414 (10)	0.0072 (10)	0.0262 (9)	0.0034 (8)

C1—C2	1.382 (3)	C7—O8	1.213 (2)
C1—C6	1.394 (3)	C7—N9	1.383 (3)
C1—C7	1.493 (2)	N9—C10	1.369 (2)
C2—C3	1.381 (3)	N9—H9	0.89 (2)
C2—H2	0.93	C10—N12	1.372 (3)
C3—C4	1.371 (3)	C10—S11	1.642 (2)
C3—H3	0.93	N12—C13	1.398 (2)
C4—C5	1.368 (3)	N12—H12	0.88 (2)
C4—H4	0.93	C13—O14	1.236 (2)
C5—C6	1.379 (3)	C13—N15	1.321 (3)
C5—H5	0.93	N15—H15A	0.91 (3)
C6—H6	0.93	N15—H15B	0.87 (3)
C2—C1—C6	118.77 (18)	O8—C7—N9	122.94 (17)
C2—C1—C7	117.03 (17)	O8—C7—C1	122.10 (19)
C6—C1—C7	124.20 (19)	N9—C7—C1	114.96 (16)
C3—C2—C1	120.6 (2)	C10—N9—C7	128.94 (17)
C3—C2—H2	119.7	C10—N9—H9	110.5 (15)
C1—C2—H2	119.7	C7—N9—H9	120.5 (14)
C4—C3—C2	120.1 (2)	N9—C10—N12	114.10 (17)
C4—C3—H3	120	N9—C10—S11	127.48 (17)
C2—C3—H3	120	N12—C10—S11	118.40 (15)
C5—C4—C3	120.0 (2)	C10—N12—C13	129.15 (17)
C5—C4—H4	120	C10—N12—H12	116.3 (13)
C3—C4—H4	120	C13—N12—H12	113.8 (13)
C4—C5—C6	120.6 (2)	O14—C13—N15	124.21 (19)
C4—C5—H5	119.7	O14—C13—N12	121.74 (19)
C6—C5—H5	119.7	N15—C13—N12	114.05 (18)
C5—C6—C1	119.9 (2)	C13—N15—H15A	122.3 (16)
C5—C6—H6	120	C13—N15—H15B	114.8 (16)
C1—C6—H6	120	H15A—N15—H15B	117 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O14	0.89 (2)	1.82 (2)	2.617 (2)	147 (2)
N12—H12···O8i	0.88 (2)	2.11 (2)	2.946 (2)	158.7 (18)
N15—H15A···O8i	0.91 (3)	2.22 (3)	3.025 (2)	147 (2)
N15—H15A···S11i	0.91 (3)	2.61 (3)	3.312 (2)	134 (2)
N15—H15B···O14ii	0.87 (3)	2.08 (3)	2.943 (2)	177 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9⋯O14	0.89 (2)	1.82 (2)	2.617 (2)	147 (2)
N12—H12⋯O8i	0.88 (2)	2.11 (2)	2.946 (2)	158.7 (18)
N15—H15A⋯O8i	0.91 (3)	2.22 (3)	3.025 (2)	147 (2)
N15—H15A⋯S11i	0.91 (3)	2.61 (3)	3.312 (2)	134 (2)
N15—H15B⋯O14ii	0.87 (3)	2.08 (3)	2.943 (2)	177 (2)

Symmetry codes: (i) ; (ii) .