A monoclinic polymorph of 1-benzoyl-4-thio-biuret.

The title compound, C9H9N3O2S, is a monoclinic (C2/c) polymorph of the previously reported triclinic structure [Kang (2013 ▶). Acta Cryst. E69, o1327]. The mol-ecule is almost planar with an r.m.s. deviation of 0.069 Å from the mean plane of all non-H atoms. The benzoyl and terminal thio-urea fragments adopt a transoid conformation with respect to the central carbonyl O atom. Two intra-molecular N-H⋯O hydrogen bonds are present. In the crystal, N-H⋯O and N-H⋯S inter-actions link the mol-ecules into zigzag chains extending along the c-axis direction.

Related literature

For the biological activity of thia­diazole derivatives, see: Piskala et al. (2004 ▶); Castro et al. (2008 ▶). For the structure and reactivity of thia­diazole derivatives, see: Cho et al. (1996 ▶). For the structure of a thio­biuret compound, see: Kang et al. (2012 ▶) and of the monoclinic polymorph, see: Kang (2013 ▶).

Experimental

Crystal data

C9H9N3O2S

M = 223.25

Monoclinic,

a = 14.4259 (14) Å

b = 6.6145 (6) Å

c = 21.722 (2) Å

β = 94.166 (3)°

V = 2067.2 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.18 × 0.12 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.96, T max = 0.99

7756 measured reflections

1973 independent reflections

1293 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.115

S = 1.03

1973 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); 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/S1600536813030250/lr2116sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813030250/lr2116Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813030250/lr2116Isup3.cml

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

C9H9N3O2S	F(000) = 928
Mr = 223.25	Dx = 1.435 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 883 reflections
a = 14.4259 (14) Å	θ = 2.8–20.7°
b = 6.6145 (6) Å	µ = 0.30 mm−1
c = 21.722 (2) Å	T = 296 K
β = 94.166 (3)°	Block, yellow
V = 2067.2 (3) Å3	0.18 × 0.12 × 0.04 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	1293 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −14→17
Tmin = 0.96, Tmax = 0.99	k = −8→3
7756 measured reflections	l = −26→14
1973 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0483P)2 + 0.5497P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
1973 reflections	Δρmax = 0.21 e Å−3
152 parameters	Δρmin = −0.23 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	0.33533 (17)	1.0358 (4)	0.65485 (12)	0.0376 (6)
C2	0.3931 (2)	1.1557 (4)	0.69320 (13)	0.0488 (7)
H2	0.4542	1.1162	0.7031	0.059*
C3	0.3604 (2)	1.3340 (4)	0.71691 (15)	0.0589 (9)
H3	0.3994	1.4133	0.7429	0.071*
C4	0.2704 (2)	1.3943 (4)	0.70214 (14)	0.0573 (9)
H4	0.2492	1.5159	0.7174	0.069*
C5	0.2120 (2)	1.2761 (4)	0.66512 (15)	0.0563 (8)
H5	0.1508	1.3161	0.6559	0.068*
C6	0.24417 (19)	1.0959 (4)	0.64118 (13)	0.0486 (7)
H6	0.2043	1.0158	0.616	0.058*
C7	0.37532 (18)	0.8447 (4)	0.63138 (13)	0.0396 (7)
O8	0.44757 (13)	0.7726 (3)	0.65381 (9)	0.0561 (6)
N9	0.32479 (17)	0.7544 (3)	0.58270 (11)	0.0439 (6)
H9	0.2806 (18)	0.812 (4)	0.5652 (12)	0.039 (8)*
C10	0.34054 (18)	0.5751 (4)	0.55260 (13)	0.0384 (6)
O11	0.28343 (12)	0.5116 (3)	0.51289 (9)	0.0472 (5)
N12	0.42172 (15)	0.4788 (3)	0.57068 (11)	0.0393 (6)
H12	0.4561 (17)	0.535 (4)	0.6002 (12)	0.037 (8)*
C13	0.45494 (17)	0.3010 (4)	0.54659 (13)	0.0382 (7)
S14	0.55856 (5)	0.21601 (11)	0.57483 (4)	0.0510 (3)
N15	0.40313 (19)	0.2107 (4)	0.50312 (13)	0.0521 (7)
H15A	0.425 (2)	0.083 (5)	0.4869 (15)	0.086 (11)*
H15B	0.351 (2)	0.248 (5)	0.4927 (15)	0.068 (11)*

	U11	U22	U33	U12	U13	U23
C1	0.0416 (16)	0.0347 (14)	0.0363 (16)	−0.0008 (11)	0.0021 (12)	−0.0012 (12)
C2	0.0482 (18)	0.0489 (17)	0.0488 (19)	−0.0032 (13)	0.0008 (14)	−0.0116 (15)
C3	0.071 (2)	0.0495 (18)	0.056 (2)	−0.0128 (16)	0.0079 (17)	−0.0189 (16)
C4	0.076 (2)	0.0399 (17)	0.057 (2)	0.0053 (15)	0.0172 (17)	−0.0096 (15)
C5	0.058 (2)	0.0545 (19)	0.057 (2)	0.0191 (15)	0.0040 (15)	−0.0054 (16)
C6	0.0497 (18)	0.0467 (17)	0.0487 (19)	0.0032 (13)	−0.0009 (14)	−0.0070 (14)
C7	0.0392 (17)	0.0348 (14)	0.0440 (18)	0.0001 (11)	−0.0025 (13)	−0.0001 (13)
O8	0.0495 (13)	0.0491 (12)	0.0667 (15)	0.0115 (10)	−0.0165 (11)	−0.0113 (10)
N9	0.0457 (15)	0.0362 (13)	0.0476 (16)	0.0126 (11)	−0.0111 (12)	−0.0071 (11)
C10	0.0351 (15)	0.0319 (14)	0.0476 (18)	0.0022 (11)	−0.0005 (13)	−0.0022 (13)
O11	0.0416 (11)	0.0413 (11)	0.0568 (13)	0.0059 (9)	−0.0097 (10)	−0.0098 (10)
N12	0.0349 (13)	0.0330 (12)	0.0488 (16)	0.0047 (10)	−0.0054 (11)	−0.0070 (11)
C13	0.0353 (15)	0.0312 (13)	0.0486 (18)	0.0004 (11)	0.0059 (13)	−0.0012 (13)
S14	0.0368 (4)	0.0439 (4)	0.0713 (6)	0.0082 (3)	−0.0014 (4)	−0.0077 (4)
N15	0.0417 (17)	0.0421 (15)	0.071 (2)	0.0092 (12)	−0.0036 (14)	−0.0195 (13)

C1—C2	1.384 (4)	C7—O8	1.216 (3)
C1—C6	1.385 (3)	C7—N9	1.376 (3)
C1—C7	1.494 (3)	N9—C10	1.381 (3)
C2—C3	1.383 (4)	N9—H9	0.81 (3)
C2—H2	0.93	C10—O11	1.223 (3)
C3—C4	1.373 (4)	C10—N12	1.366 (3)
C3—H3	0.93	N12—C13	1.386 (3)
C4—C5	1.367 (4)	N12—H12	0.86 (3)
C4—H4	0.93	C13—N15	1.306 (4)
C5—C6	1.393 (4)	C13—S14	1.671 (3)
C5—H5	0.93	N15—H15A	0.98 (4)
C6—H6	0.93	N15—H15B	0.81 (3)
C2—C1—C6	119.0 (2)	O8—C7—N9	121.9 (2)
C2—C1—C7	117.4 (2)	O8—C7—C1	122.4 (2)
C6—C1—C7	123.6 (2)	N9—C7—C1	115.7 (2)
C3—C2—C1	120.4 (3)	C7—N9—C10	129.8 (2)
C3—C2—H2	119.8	C7—N9—H9	120.5 (19)
C1—C2—H2	119.8	C10—N9—H9	109.4 (19)
C4—C3—C2	120.2 (3)	O11—C10—N12	124.2 (2)
C4—C3—H3	119.9	O11—C10—N9	120.2 (2)
C2—C3—H3	119.9	N12—C10—N9	115.6 (2)
C5—C4—C3	120.2 (3)	C10—N12—C13	126.9 (2)
C5—C4—H4	119.9	C10—N12—H12	116.6 (17)
C3—C4—H4	119.9	C13—N12—H12	116.5 (17)
C4—C5—C6	120.1 (3)	N15—C13—N12	117.7 (2)
C4—C5—H5	120	N15—C13—S14	124.1 (2)
C6—C5—H5	120	N12—C13—S14	118.1 (2)
C1—C6—C5	120.1 (3)	C13—N15—H15A	118.2 (18)
C1—C6—H6	119.9	C13—N15—H15B	122 (2)
C5—C6—H6	119.9	H15A—N15—H15B	119 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O11i	0.81 (3)	2.20 (3)	2.945 (3)	151 (2)
N12—H12···O8	0.86 (3)	1.97 (3)	2.661 (3)	136 (2)
N15—H15A···S14ii	0.98 (4)	2.41 (4)	3.358 (3)	163 (3)
N15—H15B···O11	0.81 (3)	2.06 (3)	2.653 (3)	130 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9⋯O11i	0.81 (3)	2.20 (3)	2.945 (3)	151 (2)
N12—H12⋯O8	0.86 (3)	1.97 (3)	2.661 (3)	136 (2)
N15—H15A⋯S14ii	0.98 (4)	2.41 (4)	3.358 (3)	163 (3)
N15—H15B⋯O11	0.81 (3)	2.06 (3)	2.653 (3)	130 (3)

Symmetry codes: (i) ; (ii) .