1-Benzoyl-4-thio-biuret.

IN THE TITLE COMPOUND (SYSTEMATIC NAME: {[(phenyl-formamido)-carbon-yl]amino}-methane-thio-amide), C9H9N3O2S, both benzoyl and terminal thio-urea fragments adopt transoid conformations with respect to the central carbonyl O atom. The benzoyl and thio-biuret groups are almost coplanar, making a dihedral angle of 4.40 (8)°. The mol-ecular structure is stabilized by two intra-molecular N-H⋯O hydrogen bonds. In the crystal, N-H⋯O and N-H⋯S hydrogen bonds link the mol-ecules into a tape running along [101].

Related literature

For the structure and reactivity of thia­diazole derivatives, see: Cho, Ra et al. (1996 ▶); Cho, Cho et al. (1996 ▶). For the structure of a thio­biuret isomer, see: Kang et al. (2012 ▶).

Experimental

Crystal data

C9H9N3O2S

M = 223.25

Triclinic,

a = 5.6616 (1) Å

b = 7.8407 (2) Å

c = 11.7631 (3) Å

α = 97.169 (2)°

β = 94.992 (3)°

γ = 101.390 (2)°

V = 504.53 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.2 × 0.15 × 0.07 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.94, T max = 0.97

17356 measured reflections

2516 independent reflections

1485 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 0.87

2516 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2013 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019983/is5292sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019983/is5292Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019983/is5292Isup3.cml

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

C9H9N3O2S	Z = 2
Mr = 223.25	F(000) = 232
Triclinic, P1	Dx = 1.47 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6616 (1) Å	Cell parameters from 3132 reflections
b = 7.8407 (2) Å	θ = 2.7–22.3°
c = 11.7631 (3) Å	µ = 0.30 mm−1
α = 97.169 (2)°	T = 296 K
β = 94.992 (3)°	Block, yellow
γ = 101.390 (2)°	0.2 × 0.15 × 0.07 mm
V = 504.53 (2) Å3

Bruker SMART CCD diffractometer	1485 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
φ and ω scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −7→7
Tmin = 0.94, Tmax = 0.97	k = −10→10
17356 measured reflections	l = −15→15
2516 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.052P)2] where P = (Fo2 + 2Fc2)/3
S = 0.87	(Δ/σ)max < 0.001
2516 reflections	Δρmax = 0.16 e Å−3
152 parameters	Δρmin = −0.20 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.

	x	y	z	Uiso*/Ueq
C1	0.0374 (3)	0.8224 (2)	−0.12506 (14)	0.0447 (4)
C2	0.2488 (3)	0.9206 (2)	−0.15393 (16)	0.0597 (5)
H2	0.3881	0.9477	−0.1014	0.072*
C3	0.2552 (4)	0.9785 (3)	−0.25952 (19)	0.0729 (6)
H3	0.398	1.0453	−0.2778	0.087*
C4	0.0539 (4)	0.9383 (3)	−0.33677 (18)	0.0723 (6)
H4	0.06	0.9763	−0.4085	0.087*
C5	−0.1598 (4)	0.8419 (3)	−0.31035 (18)	0.0753 (6)
H5	−0.2979	0.8154	−0.3636	0.09*
C6	−0.1672 (3)	0.7846 (3)	−0.20373 (16)	0.0615 (5)
H6	−0.3114	0.7203	−0.1851	0.074*
C7	0.0480 (3)	0.7661 (2)	−0.00927 (14)	0.0442 (4)
O8	0.2338 (2)	0.80629 (17)	0.05733 (11)	0.0633 (4)
N9	−0.1594 (2)	0.66558 (19)	0.02071 (12)	0.0467 (4)
H9	−0.284 (3)	0.634 (2)	−0.0281 (16)	0.054 (5)*
C10	−0.1998 (3)	0.6059 (2)	0.12532 (14)	0.0446 (4)
O11	−0.3996 (2)	0.52249 (17)	0.13780 (10)	0.0603 (4)
N12	−0.0057 (2)	0.64570 (19)	0.20766 (11)	0.0467 (4)
H12	0.131 (4)	0.707 (2)	0.1906 (17)	0.067 (6)*
C13	0.0039 (3)	0.6057 (2)	0.31929 (13)	0.0447 (4)
S14	0.27039 (8)	0.66392 (7)	0.40142 (4)	0.05930 (19)
N15	−0.1971 (3)	0.5267 (3)	0.35341 (15)	0.0646 (5)
H15A	−0.336 (4)	0.507 (2)	0.3052 (18)	0.075 (6)*
H15B	−0.199 (3)	0.486 (2)	0.4173 (18)	0.066 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0468 (9)	0.0459 (10)	0.0402 (9)	0.0048 (8)	0.0046 (7)	0.0100 (8)
C2	0.0539 (10)	0.0726 (13)	0.0505 (11)	0.0013 (9)	0.0049 (8)	0.0214 (10)
C3	0.0714 (13)	0.0858 (16)	0.0630 (14)	0.0016 (12)	0.0175 (11)	0.0337 (12)
C4	0.0944 (16)	0.0782 (15)	0.0503 (12)	0.0174 (13)	0.0138 (12)	0.0294 (11)
C5	0.0810 (15)	0.0890 (16)	0.0523 (12)	0.0069 (13)	−0.0107 (11)	0.0263 (11)
C6	0.0564 (11)	0.0714 (13)	0.0518 (12)	−0.0029 (9)	−0.0038 (9)	0.0230 (10)
C7	0.0403 (9)	0.0483 (10)	0.0410 (9)	0.0009 (7)	0.0013 (7)	0.0102 (8)
O8	0.0426 (6)	0.0882 (10)	0.0501 (7)	−0.0140 (6)	−0.0047 (6)	0.0269 (7)
N9	0.0392 (7)	0.0609 (10)	0.0353 (8)	−0.0021 (7)	−0.0023 (6)	0.0141 (7)
C10	0.0411 (9)	0.0546 (11)	0.0349 (9)	0.0016 (8)	0.0012 (7)	0.0099 (8)
O11	0.0397 (6)	0.0898 (10)	0.0432 (7)	−0.0107 (6)	−0.0017 (5)	0.0213 (6)
N12	0.0370 (7)	0.0637 (10)	0.0359 (8)	−0.0022 (7)	0.0008 (6)	0.0165 (7)
C13	0.0401 (8)	0.0588 (11)	0.0355 (9)	0.0069 (8)	0.0047 (7)	0.0129 (8)
S14	0.0402 (2)	0.0911 (4)	0.0424 (3)	0.0002 (2)	−0.00342 (18)	0.0213 (2)
N15	0.0403 (8)	0.1120 (15)	0.0414 (9)	0.0026 (9)	0.0021 (7)	0.0336 (10)

C1—C6	1.377 (2)	C7—O8	1.2181 (18)
C1—C2	1.383 (2)	C7—N9	1.378 (2)
C1—C7	1.483 (2)	N9—C10	1.391 (2)
C2—C3	1.376 (3)	N9—H9	0.843 (18)
C2—H2	0.93	C10—O11	1.2205 (18)
C3—C4	1.353 (3)	C10—N12	1.3591 (19)
C3—H3	0.93	N12—C13	1.387 (2)
C4—C5	1.377 (3)	N12—H12	0.882 (19)
C4—H4	0.93	C13—N15	1.305 (2)
C5—C6	1.385 (3)	C13—S14	1.6679 (16)
C5—H5	0.93	N15—H15A	0.91 (2)
C6—H6	0.93	N15—H15B	0.85 (2)
C6—C1—C2	118.74 (16)	O8—C7—N9	120.79 (15)
C6—C1—C7	124.45 (15)	O8—C7—C1	121.33 (14)
C2—C1—C7	116.81 (15)	N9—C7—C1	117.87 (14)
C3—C2—C1	120.69 (18)	C7—N9—C10	128.80 (14)
C3—C2—H2	119.7	C7—N9—H9	119.4 (12)
C1—C2—H2	119.7	C10—N9—H9	111.8 (12)
C4—C3—C2	120.02 (18)	O11—C10—N12	124.46 (15)
C4—C3—H3	120	O11—C10—N9	119.83 (14)
C2—C3—H3	120	N12—C10—N9	115.71 (14)
C3—C4—C5	120.70 (19)	C10—N12—C13	127.81 (14)
C3—C4—H4	119.7	C10—N12—H12	117.8 (13)
C5—C4—H4	119.7	C13—N12—H12	114.4 (13)
C4—C5—C6	119.38 (19)	N15—C13—N12	117.68 (14)
C4—C5—H5	120.3	N15—C13—S14	124.41 (13)
C6—C5—H5	120.3	N12—C13—S14	117.91 (12)
C1—C6—C5	120.46 (18)	C13—N15—H15A	118.8 (13)
C1—C6—H6	119.8	C13—N15—H15B	121.9 (13)
C5—C6—H6	119.8	H15A—N15—H15B	119.1 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O11i	0.843 (18)	2.172 (18)	2.9891 (18)	163.3 (16)
N12—H12···O8	0.882 (19)	1.919 (19)	2.6171 (17)	135.0 (17)
N15—H15A···O11	0.91 (2)	1.99 (2)	2.684 (2)	132.0 (17)
N15—H15B···S14ii	0.85 (2)	2.58 (2)	3.4295 (17)	171.3 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9⋯O11i	0.843 (18)	2.172 (18)	2.9891 (18)	163.3 (16)
N12—H12⋯O8	0.882 (19)	1.919 (19)	2.6171 (17)	135.0 (17)
N15—H15A⋯O11	0.91 (2)	1.99 (2)	2.684 (2)	132.0 (17)
N15—H15B⋯S14ii	0.85 (2)	2.58 (2)	3.4295 (17)	171.3 (17)

Symmetry codes: (i) ; (ii) .