3-Acetyl-1-phenyl-thio-urea.

In the crystal structure of title compound, C(9)H(10)N(2)OS, there are two symmetry-independent mol-ecules, each having an intra-molecular N-H⋯O hydrogen bond generating an S(6) ring motif. The benzene rings and the virtually planar acetyl-thoiurea fragments [r.m.s. deviations = 0.0045 and 0.0341 Å] are oriented at dihedral angles of 50.71 (6) and 62.79 (6)° in the two mol-ecules. In the crystal, N-H⋯S and N-H⋯O hydrogen bonds link mol-ecules via cyclic R(2) (2)(8) and R(2) (2)(12) motifs into a one-dimensional polymeric network extending along [101]. The intra- and inter-molecular N-H⋯O inter-actions are part of a three-center hydrogen bond. A C-H⋯S inter-action also occurs.

Related literature

For related structures, see: Othman et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H10N2OS

M = 194.25

Monoclinic,

a = 10.1911 (2) Å

b = 22.5480 (4) Å

c = 8.9736 (2) Å

β = 112.449 (1)°

V = 1905.77 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.35 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.915, T max = 0.938

16643 measured reflections

4679 independent reflections

3626 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.129

S = 1.05

4679 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812002371/gk2451sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002371/gk2451Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002371/gk2451Isup3.cml

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

C9H10N2OS	F(000) = 816
Mr = 194.25	Dx = 1.354 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3626 reflections
a = 10.1911 (2) Å	θ = 2.2–28.3°
b = 22.5480 (4) Å	µ = 0.30 mm−1
c = 8.9736 (2) Å	T = 296 K
β = 112.449 (1)°	Prism, light green
V = 1905.77 (7) Å3	0.35 × 0.25 × 0.22 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	4679 independent reflections
Radiation source: fine-focus sealed tube	3626 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 8.00 pixels mm-1	θmax = 28.3°, θmin = 2.2°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −23→29
Tmin = 0.915, Tmax = 0.938	l = −11→11
16643 measured 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0574P)2 + 0.6731P] where P = (Fo2 + 2Fc2)/3
4679 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
S1	−0.19196 (6)	0.05015 (3)	0.17599 (8)	0.0666 (2)
O1	0.22186 (16)	−0.05280 (6)	0.3471 (2)	0.0647 (5)
N1	0.08613 (17)	0.04741 (6)	0.35398 (19)	0.0455 (5)
N2	−0.01041 (17)	−0.03499 (6)	0.19702 (19)	0.0463 (5)
C1	0.09330 (18)	0.10632 (7)	0.4158 (2)	0.0388 (5)
C2	0.1603 (2)	0.11483 (8)	0.5792 (2)	0.0455 (6)
C3	0.1800 (2)	0.17188 (9)	0.6419 (3)	0.0548 (7)
C4	0.1317 (2)	0.21994 (8)	0.5415 (3)	0.0546 (7)
C5	0.0635 (3)	0.21096 (8)	0.3790 (3)	0.0575 (7)
C6	0.0449 (2)	0.15463 (8)	0.3146 (2)	0.0532 (7)
C7	−0.0283 (2)	0.02154 (8)	0.2479 (2)	0.0428 (5)
C8	0.1098 (2)	−0.06975 (8)	0.2494 (2)	0.0449 (6)
C9	0.08992 (12)	−0.13043 (2)	0.17563 (12)	0.0596 (7)
S2	0.29361 (6)	0.11538 (2)	0.07535 (6)	0.0571 (2)
O2	0.59666 (10)	−0.02218 (2)	0.39879 (7)	0.0624 (5)
N3	0.52470 (6)	0.09140 (2)	0.33705 (7)	0.0456 (5)
N4	0.41578 (16)	0.01207 (6)	0.1764 (2)	0.0463 (5)
C10	0.5529 (2)	0.15166 (7)	0.3895 (2)	0.0419 (5)
C11	0.4580 (2)	0.18411 (10)	0.4315 (3)	0.0569 (7)
C12	0.4945 (3)	0.24100 (10)	0.4927 (3)	0.0692 (9)
C13	0.6232 (3)	0.26489 (9)	0.5078 (3)	0.0669 (8)
C14	0.7165 (3)	0.23256 (10)	0.4653 (3)	0.0641 (8)
C15	0.6826 (2)	0.17540 (9)	0.4056 (3)	0.0523 (6)
C16	0.41954 (19)	0.07247 (7)	0.2070 (2)	0.0405 (5)
C17	0.5029 (2)	−0.03202 (8)	0.2695 (2)	0.0459 (6)
C18	0.4715 (2)	−0.09258 (9)	0.1962 (3)	0.0590 (7)
H1	0.16310	0.02690	0.38876	0.0545*
H2	0.19244	0.08241	0.64760	0.0546*
H2A	−0.08394	−0.05025	0.12321	0.0555*
H3	0.22598	0.17763	0.75237	0.0658*
H4	0.14526	0.25818	0.58346	0.0655*
H5	0.02914	0.24337	0.31114	0.0690*
H6	0.00015	0.14915	0.20379	0.0639*
H9A	0.15836	−0.15710	0.24765	0.0894*
H9B	0.10276	−0.12869	0.07516	0.0894*
H9C	−0.00410	−0.14434	0.15685	0.0894*
H3A	0.58190	0.06497	0.39608	0.0548*
H4A	0.35054	0.00054	0.08761	0.0556*
H11	0.37031	0.16814	0.41908	0.0682*
H12	0.43186	0.26299	0.52351	0.0830*
H13	0.64664	0.30324	0.54715	0.0803*
H14	0.80349	0.24893	0.47639	0.0769*
H15	0.74639	0.15337	0.37671	0.0627*
H18A	0.52816	−0.09968	0.13370	0.0886*
H18B	0.37273	−0.09519	0.12774	0.0886*
H18C	0.49338	−0.12174	0.28022	0.0886*

	U11	U22	U33	U12	U13	U23
S1	0.0461 (3)	0.0524 (3)	0.0799 (4)	0.0084 (2)	0.0003 (3)	−0.0220 (3)
O1	0.0495 (8)	0.0449 (8)	0.0774 (10)	0.0053 (6)	−0.0008 (8)	−0.0177 (7)
N1	0.0430 (8)	0.0309 (8)	0.0525 (9)	0.0012 (6)	0.0071 (7)	−0.0056 (6)
N2	0.0436 (8)	0.0339 (8)	0.0500 (9)	−0.0021 (6)	0.0053 (7)	−0.0088 (6)
C1	0.0400 (9)	0.0290 (8)	0.0459 (9)	−0.0014 (7)	0.0147 (8)	−0.0031 (7)
C2	0.0501 (10)	0.0370 (9)	0.0446 (10)	0.0048 (8)	0.0128 (8)	0.0013 (7)
C3	0.0629 (12)	0.0491 (11)	0.0465 (11)	0.0021 (9)	0.0143 (9)	−0.0117 (9)
C4	0.0709 (13)	0.0340 (10)	0.0654 (13)	−0.0038 (9)	0.0332 (11)	−0.0104 (9)
C5	0.0835 (15)	0.0314 (10)	0.0602 (12)	0.0039 (9)	0.0302 (12)	0.0064 (8)
C6	0.0739 (14)	0.0386 (10)	0.0422 (10)	0.0001 (9)	0.0166 (10)	0.0025 (8)
C7	0.0470 (10)	0.0336 (9)	0.0431 (9)	−0.0001 (7)	0.0121 (8)	−0.0024 (7)
C8	0.0472 (10)	0.0342 (9)	0.0475 (10)	0.0001 (7)	0.0115 (8)	−0.0036 (7)
C9	0.0599 (12)	0.0392 (10)	0.0691 (14)	0.0009 (9)	0.0128 (11)	−0.0143 (10)
S2	0.0581 (3)	0.0369 (3)	0.0535 (3)	0.0050 (2)	−0.0041 (2)	0.0012 (2)
O2	0.0595 (9)	0.0436 (8)	0.0599 (9)	0.0107 (7)	−0.0041 (7)	−0.0056 (7)
N3	0.0441 (8)	0.0323 (7)	0.0481 (9)	0.0042 (6)	0.0037 (7)	−0.0030 (6)
N4	0.0443 (8)	0.0328 (8)	0.0485 (9)	−0.0012 (6)	0.0029 (7)	−0.0049 (6)
C10	0.0478 (10)	0.0309 (8)	0.0381 (9)	0.0018 (7)	0.0063 (8)	−0.0013 (7)
C11	0.0540 (12)	0.0503 (12)	0.0620 (13)	0.0037 (9)	0.0174 (10)	−0.0091 (9)
C12	0.0836 (17)	0.0504 (13)	0.0657 (14)	0.0180 (12)	0.0197 (13)	−0.0105 (10)
C13	0.0972 (19)	0.0329 (10)	0.0563 (13)	−0.0030 (11)	0.0134 (12)	−0.0048 (9)
C14	0.0773 (15)	0.0446 (12)	0.0647 (14)	−0.0174 (11)	0.0206 (12)	−0.0023 (10)
C15	0.0573 (12)	0.0424 (10)	0.0543 (11)	−0.0020 (9)	0.0182 (10)	−0.0015 (8)
C16	0.0394 (9)	0.0337 (9)	0.0443 (9)	−0.0012 (7)	0.0114 (8)	−0.0004 (7)
C17	0.0412 (9)	0.0357 (9)	0.0532 (11)	0.0031 (7)	0.0095 (8)	−0.0017 (8)
C18	0.0563 (12)	0.0348 (10)	0.0703 (14)	0.0060 (9)	0.0067 (10)	−0.0063 (9)

S1—C7	1.671 (2)	C2—H2	0.9300
S2—C16	1.6796 (18)	C3—H3	0.9300
O1—C8	1.206 (3)	C4—H4	0.9300
O2—C17	1.2090 (19)	C5—H5	0.9300
N1—C7	1.326 (2)	C6—H6	0.9300
N1—C1	1.431 (2)	C9—H9A	0.9600
N2—C7	1.389 (2)	C9—H9B	0.9600
N2—C8	1.377 (3)	C9—H9C	0.9600
N1—H1	0.8600	C10—C15	1.382 (3)
N2—H2A	0.8600	C10—C11	1.375 (3)
N3—C10	1.4307 (17)	C11—C12	1.389 (3)
N3—C16	1.3181 (18)	C12—C13	1.376 (4)
N4—C16	1.387 (2)	C13—C14	1.363 (4)
N4—C17	1.381 (2)	C14—C15	1.388 (3)
N3—H3A	0.8600	C17—C18	1.496 (3)
N4—H4A	0.8600	C11—H11	0.9300
C1—C6	1.383 (2)	C12—H12	0.9300
C1—C2	1.374 (2)	C13—H13	0.9300
C2—C3	1.388 (3)	C14—H14	0.9300
C3—C4	1.375 (3)	C15—H15	0.9300
C4—C5	1.370 (4)	C18—H18A	0.9600
C5—C6	1.378 (3)	C18—H18B	0.9600
C8—C9	1.4996 (19)	C18—H18C	0.9600
C1—N1—C7	125.98 (17)	H9A—C9—H9C	109.00
C7—N2—C8	128.41 (16)	C8—C9—H9A	109.00
C7—N1—H1	117.00	H9B—C9—H9C	109.00
C1—N1—H1	117.00	C8—C9—H9C	109.00
C8—N2—H2A	116.00	H9A—C9—H9B	109.00
C7—N2—H2A	116.00	C8—C9—H9B	109.00
C10—N3—C16	126.30 (11)	C11—C10—C15	120.67 (17)
C16—N4—C17	128.62 (16)	N3—C10—C11	121.43 (18)
C16—N3—H3A	117.00	N3—C10—C15	117.80 (17)
C10—N3—H3A	117.00	C10—C11—C12	119.3 (2)
C17—N4—H4A	116.00	C11—C12—C13	120.1 (2)
C16—N4—H4A	116.00	C12—C13—C14	120.2 (2)
C2—C1—C6	119.87 (15)	C13—C14—C15	120.5 (3)
N1—C1—C2	118.32 (15)	C10—C15—C14	119.2 (2)
N1—C1—C6	121.61 (15)	S2—C16—N3	125.50 (11)
C1—C2—C3	119.88 (17)	S2—C16—N4	118.07 (13)
C2—C3—C4	120.3 (2)	N3—C16—N4	116.42 (14)
C3—C4—C5	119.36 (19)	O2—C17—C18	123.18 (17)
C4—C5—C6	121.01 (18)	N4—C17—C18	114.25 (16)
C1—C6—C5	119.54 (17)	O2—C17—N4	122.57 (16)
N1—C7—N2	116.73 (18)	C10—C11—H11	120.00
S1—C7—N2	117.66 (14)	C12—C11—H11	120.00
S1—C7—N1	125.58 (14)	C11—C12—H12	120.00
O1—C8—N2	122.67 (17)	C13—C12—H12	120.00
N2—C8—C9	114.58 (15)	C12—C13—H13	120.00
O1—C8—C9	122.74 (17)	C14—C13—H13	120.00
C3—C2—H2	120.00	C13—C14—H14	120.00
C1—C2—H2	120.00	C15—C14—H14	120.00
C4—C3—H3	120.00	C10—C15—H15	120.00
C2—C3—H3	120.00	C14—C15—H15	120.00
C3—C4—H4	120.00	C17—C18—H18A	109.00
C5—C4—H4	120.00	C17—C18—H18B	109.00
C6—C5—H5	120.00	C17—C18—H18C	109.00
C4—C5—H5	119.00	H18A—C18—H18B	109.00
C1—C6—H6	120.00	H18A—C18—H18C	109.00
C5—C6—H6	120.00	H18B—C18—H18C	109.00
C7—N1—C1—C2	133.6 (2)	C6—C1—C2—C3	−0.4 (3)
C7—N1—C1—C6	−51.6 (3)	N1—C1—C6—C5	−175.2 (2)
C1—N1—C7—S1	−5.7 (3)	C2—C1—C6—C5	−0.5 (3)
C1—N1—C7—N2	176.57 (16)	N1—C1—C2—C3	174.48 (19)
C8—N2—C7—S1	−173.67 (16)	C1—C2—C3—C4	0.6 (3)
C8—N2—C7—N1	4.2 (3)	C2—C3—C4—C5	0.2 (4)
C7—N2—C8—O1	−3.3 (3)	C3—C4—C5—C6	−1.2 (4)
C7—N2—C8—C9	176.44 (16)	C4—C5—C6—C1	1.3 (4)
C10—N3—C16—S2	−1.0 (2)	N3—C10—C11—C12	175.39 (18)
C16—N3—C10—C11	62.9 (2)	C15—C10—C11—C12	−0.9 (3)
C16—N3—C10—C15	−120.69 (19)	N3—C10—C15—C14	−176.23 (18)
C10—N3—C16—N4	177.67 (15)	C11—C10—C15—C14	0.2 (3)
C16—N4—C17—C18	−177.93 (19)	C10—C11—C12—C13	1.3 (4)
C17—N4—C16—S2	−176.84 (17)	C11—C12—C13—C14	−1.1 (4)
C17—N4—C16—N3	4.4 (3)	C12—C13—C14—C15	0.4 (4)
C16—N4—C17—O2	1.8 (3)	C13—C14—C15—C10	0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.97	2.662 (2)	136
N1—H1···O2i	0.86	2.46	3.1967 (19)	143
N2—H2A···S2ii	0.86	2.64	3.4931 (17)	170
N3—H3A···O2	0.86	1.97	2.6633 (7)	137
N3—H3A···O1i	0.86	2.42	3.1418 (18)	142
N4—H4A···S1ii	0.86	2.57	3.4150 (18)	168
C18—H18B···S1ii	0.96	2.83	3.594 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.97	2.662 (2)	136
N1—H1⋯O2i	0.86	2.46	3.1967 (19)	143
N2—H2A⋯S2ii	0.86	2.64	3.4931 (17)	170
N3—H3A⋯O2	0.86	1.97	2.6633 (7)	137
N3—H3A⋯O1i	0.86	2.42	3.1418 (18)	142
N4—H4A⋯S1ii	0.86	2.57	3.4150 (18)	168
C18—H18B⋯S1ii	0.96	2.83	3.594 (3)	137

Symmetry codes: (i) ; (ii) .