1-Furoyl-3-methyl-3-phenyl-thio-urea.

The title compound, C(13)H(12)N(2)O(2)S, crystallizes with two independent mol-ecules in the asymmetric unit. The two mol-ecules differ in the conformation of the thio-carbonyl and carbonyl groups, and show the typical geometric parameters of substituted thio-urea derivatives. The crystal structure is mainly stabilized by inter-molecular N-H⋯O hydrogen bonding.

Related literature

For general background, see: Estévez-Hernández et al. (2007 ▶); Otazo et al. (2001 ▶). For related structures, see: Koch et al. (1995 ▶); Morales et al. (1997 ▶). For synthesis, see: Otazo et al. (2001 ▶).

Experimental

Crystal data

C13H12N2O2S

M = 260.31

Monoclinic,

a = 10.242 (1) Å

b = 13.525 (1) Å

c = 18.432 (2) Å

β = 96.115 (4)°

V = 2538.7 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.25 mm−1

T = 150 (2) K

0.12 × 0.08 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

23939 measured reflections

4440 independent reflections

2828 reflections with I > 2σ(I)

R int = 0.093

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.117

S = 1.01

4440 reflections

327 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.39 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: HKL DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068687/xu2395sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068687/xu2395Isup2.hkl

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

C13H12N2O2S	F000 = 1088
Mr = 260.31	Dx = 1.362 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 17369 reflections
a = 10.242 (1) Å	θ = 2.9–26.0º
b = 13.525 (1) Å	µ = 0.25 mm−1
c = 18.432 (2) Å	T = 150 (2) K
β = 96.115 (4)º	Prism, colourless
V = 2538.7 (4) Å3	0.12 × 0.08 × 0.06 mm
Z = 8

Nonius KappaCCD diffractometer	Rint = 0.093
CCD scans	θmax = 25.0º
Absorption correction: none	θmin = 3.2º
23939 measured reflections	h = −12→12
4440 independent reflections	k = −15→16
2828 reflections with I > 2σ(I)	l = −21→21

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0586P)2 + 0.0231P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.046	(Δ/σ)max = 0.004
wR(F2) = 0.117	Δρmax = 0.26 e Å−3
S = 1.01	Δρmin = −0.39 e Å−3
4440 reflections	Extinction correction: none
327 parameters

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	0.2294 (3)	0.8708 (2)	0.23749 (18)	0.0532 (8)
H1A	0.2926	0.8939	0.2049	0.08*
H1B	0.2749	0.8593	0.2863	0.08*
H1C	0.1611	0.921	0.2403	0.08*
C14	0.2728 (3)	0.3832 (2)	0.26750 (17)	0.0560 (9)
H14A	0.3457	0.4205	0.2506	0.084*
H14B	0.2145	0.4285	0.2903	0.084*
H14C	0.2234	0.3502	0.2259	0.084*
C2	0.1449 (2)	0.76315 (19)	0.13688 (16)	0.0351 (7)
C15	0.3838 (2)	0.22823 (19)	0.29748 (14)	0.0339 (6)
C3	0.1874 (2)	0.58628 (18)	0.12911 (14)	0.0302 (6)
C16	0.3287 (2)	0.10391 (18)	0.38668 (14)	0.0309 (6)
C4	0.1288 (2)	0.49232 (18)	0.10477 (14)	0.0298 (6)
C17	0.3758 (2)	0.00693 (18)	0.41385 (14)	0.0302 (6)
C5	0.0051 (2)	0.4590 (2)	0.09248 (17)	0.0452 (8)
H5	−0.0726	0.4963	0.0957	0.054*
C18	0.4789 (2)	−0.04906 (19)	0.40147 (15)	0.0355 (7)
H18	0.547	−0.0316	0.3727	0.043*
C6	0.0122 (3)	0.3574 (2)	0.07366 (17)	0.0450 (8)
H6	−0.0592	0.3132	0.0626	0.054*
C19	0.4675 (2)	−0.13922 (19)	0.43928 (16)	0.0386 (7)
H19	0.5266	−0.1935	0.4413	0.046*
C7	0.1390 (3)	0.3370 (2)	0.07479 (15)	0.0398 (7)
H7	0.173	0.274	0.0637	0.048*
C20	0.3574 (3)	−0.13276 (19)	0.47157 (16)	0.0396 (7)
H20	0.3249	−0.1833	0.5006	0.047*
C8	0.1275 (2)	0.70935 (19)	0.26202 (15)	0.0341 (6)
C21	0.3303 (2)	0.33719 (18)	0.39653 (15)	0.0341 (6)
C9	0.2181 (2)	0.6730 (2)	0.31625 (16)	0.0389 (7)
H9	0.3079	0.6915	0.3179	0.047*
C22	0.4509 (3)	0.34928 (19)	0.43744 (17)	0.0437 (7)
H22	0.5303	0.3339	0.4175	0.052*
C10	0.1775 (3)	0.6096 (2)	0.36825 (16)	0.0463 (8)
H10	0.2396	0.5842	0.4056	0.056*
C23	0.4529 (4)	0.3848 (2)	0.5091 (2)	0.0604 (10)
H23	0.5343	0.393	0.5384	0.072*
C11	0.0467 (3)	0.5832 (2)	0.36605 (17)	0.0445 (7)
H11	0.0191	0.5394	0.4017	0.053*
C24	0.3370 (4)	0.4078 (2)	0.53737 (19)	0.0632 (10)
H24	0.3388	0.4324	0.5857	0.076*
C12	−0.0436 (3)	0.6203 (2)	0.31213 (18)	0.0451 (8)
H12	−0.1333	0.6017	0.3106	0.054*
C25	0.2198 (4)	0.3950 (2)	0.4957 (2)	0.0555 (9)
H25	0.1403	0.4111	0.5152	0.067*
C13	−0.0042 (2)	0.6846 (2)	0.26012 (16)	0.0415 (7)
H13	−0.0666	0.7113	0.2236	0.05*
C26	0.2157 (3)	0.3593 (2)	0.42587 (17)	0.0428 (7)
H26	0.1335	0.3498	0.3977	0.051*
O1	0.29958 (15)	0.59531 (12)	0.15853 (10)	0.0392 (5)
O3	0.21895 (15)	0.13554 (12)	0.39322 (10)	0.0390 (5)
O2	0.21429 (15)	0.41764 (12)	0.09384 (10)	0.0385 (5)
O4	0.29752 (15)	−0.04324 (13)	0.45720 (10)	0.0399 (5)
N1	0.16896 (19)	0.77824 (15)	0.20905 (13)	0.0362 (5)
N3	0.32476 (19)	0.30851 (16)	0.32120 (12)	0.0370 (6)
N2	0.10521 (19)	0.66592 (15)	0.11680 (12)	0.0352 (6)
H2	0.0251	0.6562	0.0957	0.042*
N4	0.41900 (18)	0.15394 (15)	0.35015 (12)	0.0324 (5)
H4	0.5026	0.139	0.36	0.039*
S1	0.16001 (7)	0.84691 (5)	0.07255 (4)	0.0453 (2)
S2	0.41662 (7)	0.21011 (6)	0.21239 (4)	0.0489 (2)

	U11	U22	U33	U12	U13	U23
C1	0.068 (2)	0.0363 (18)	0.054 (2)	−0.0138 (14)	−0.0010 (16)	−0.0080 (15)
C14	0.077 (2)	0.052 (2)	0.039 (2)	0.0213 (16)	0.0060 (16)	0.0122 (16)
C2	0.0294 (13)	0.0317 (16)	0.044 (2)	0.0030 (11)	0.0016 (12)	0.0027 (14)
C15	0.0277 (13)	0.0402 (17)	0.0344 (17)	0.0004 (11)	0.0063 (11)	0.0031 (14)
C3	0.0323 (15)	0.0325 (16)	0.0268 (16)	0.0011 (11)	0.0080 (11)	−0.0008 (12)
C16	0.0300 (14)	0.0341 (16)	0.0286 (17)	−0.0020 (11)	0.0037 (11)	−0.0026 (12)
C4	0.0317 (14)	0.0283 (15)	0.0295 (16)	0.0059 (11)	0.0031 (11)	0.0014 (12)
C17	0.0274 (13)	0.0321 (15)	0.0308 (17)	−0.0074 (11)	0.0014 (11)	0.0004 (12)
C5	0.0313 (15)	0.0412 (18)	0.062 (2)	0.0021 (12)	0.0024 (13)	−0.0063 (16)
C18	0.0315 (14)	0.0323 (16)	0.0444 (18)	−0.0015 (12)	0.0122 (12)	0.0007 (14)
C6	0.0445 (17)	0.0326 (17)	0.056 (2)	−0.0088 (12)	−0.0020 (14)	−0.0038 (15)
C19	0.0378 (15)	0.0346 (17)	0.0436 (19)	0.0020 (12)	0.0062 (13)	−0.0012 (14)
C7	0.0495 (18)	0.0266 (16)	0.0420 (19)	−0.0019 (13)	−0.0013 (13)	−0.0048 (13)
C20	0.0490 (17)	0.0304 (16)	0.0389 (19)	−0.0007 (12)	0.0028 (13)	0.0062 (13)
C8	0.0402 (15)	0.0288 (15)	0.0334 (17)	−0.0011 (11)	0.0045 (12)	−0.0053 (13)
C21	0.0412 (15)	0.0284 (15)	0.0334 (18)	−0.0001 (11)	0.0070 (12)	0.0053 (13)
C9	0.0358 (15)	0.0438 (17)	0.0376 (18)	−0.0029 (12)	0.0066 (13)	−0.0033 (14)
C22	0.0453 (17)	0.0353 (17)	0.049 (2)	−0.0010 (13)	−0.0010 (14)	0.0050 (15)
C10	0.0451 (17)	0.053 (2)	0.041 (2)	0.0050 (14)	0.0053 (14)	0.0009 (16)
C23	0.084 (3)	0.0342 (19)	0.056 (3)	−0.0078 (16)	−0.0251 (19)	0.0051 (17)
C11	0.0477 (17)	0.0416 (18)	0.047 (2)	0.0020 (13)	0.0177 (14)	−0.0003 (15)
C24	0.123 (3)	0.0331 (19)	0.035 (2)	0.0044 (19)	0.012 (2)	0.0034 (15)
C12	0.0379 (16)	0.0438 (18)	0.055 (2)	−0.0028 (13)	0.0122 (14)	−0.0054 (16)
C25	0.081 (2)	0.0375 (19)	0.052 (2)	0.0048 (16)	0.0279 (19)	0.0048 (17)
C13	0.0358 (15)	0.0379 (17)	0.050 (2)	0.0019 (12)	0.0020 (13)	−0.0054 (15)
C26	0.0473 (16)	0.0383 (18)	0.045 (2)	0.0007 (13)	0.0127 (14)	0.0042 (15)
O1	0.0276 (10)	0.0407 (11)	0.0491 (13)	−0.0014 (8)	0.0033 (8)	−0.0089 (9)
O3	0.0271 (10)	0.0377 (11)	0.0534 (14)	0.0017 (8)	0.0096 (8)	0.0049 (9)
O2	0.0369 (10)	0.0320 (11)	0.0463 (13)	0.0014 (8)	0.0033 (8)	−0.0040 (9)
O4	0.0359 (10)	0.0405 (12)	0.0448 (13)	0.0017 (8)	0.0111 (8)	0.0081 (9)
N1	0.0414 (12)	0.0281 (13)	0.0381 (16)	−0.0031 (9)	−0.0002 (10)	−0.0016 (11)
N3	0.0417 (12)	0.0370 (14)	0.0327 (15)	0.0092 (10)	0.0060 (10)	0.0061 (11)
N2	0.0304 (11)	0.0299 (13)	0.0431 (15)	0.0005 (9)	−0.0060 (9)	−0.0039 (11)
N4	0.0249 (11)	0.0361 (13)	0.0367 (15)	0.0017 (9)	0.0051 (9)	0.0079 (11)
S1	0.0509 (4)	0.0379 (4)	0.0480 (5)	0.0009 (3)	0.0090 (3)	0.0061 (4)
S2	0.0498 (4)	0.0634 (6)	0.0351 (5)	0.0115 (4)	0.0115 (3)	0.0031 (4)

C1—N1	1.468 (3)	C19—H19	0.95
C1—H1A	0.98	C7—O2	1.360 (3)
C1—H1B	0.98	C7—H7	0.95
C1—H1C	0.98	C20—O4	1.370 (3)
C14—N3	1.473 (3)	C20—H20	0.95
C14—H14A	0.98	C8—C9	1.380 (4)
C14—H14B	0.98	C8—C13	1.386 (3)
C14—H14C	0.98	C8—N1	1.446 (3)
C2—N1	1.342 (3)	C21—C26	1.376 (4)
C2—N2	1.414 (3)	C21—C22	1.387 (4)
C2—S1	1.659 (3)	C21—N3	1.437 (3)
C15—N3	1.339 (3)	C9—C10	1.383 (4)
C15—N4	1.417 (3)	C9—H9	0.95
C15—S2	1.657 (3)	C22—C23	1.404 (5)
C3—O1	1.223 (3)	C22—H22	0.95
C3—N2	1.371 (3)	C10—C11	1.383 (4)
C3—C4	1.456 (3)	C10—H10	0.95
C16—O3	1.221 (3)	C23—C24	1.381 (5)
C16—N4	1.378 (3)	C23—H23	0.95
C16—C17	1.467 (3)	C11—C12	1.378 (4)
C4—C5	1.341 (3)	C11—H11	0.95
C4—O2	1.366 (3)	C24—C25	1.365 (5)
C17—C18	1.338 (3)	C24—H24	0.95
C17—O4	1.371 (3)	C12—C13	1.386 (4)
C5—C6	1.421 (4)	C12—H12	0.95
C5—H5	0.95	C25—C26	1.371 (4)
C18—C19	1.416 (4)	C25—H25	0.95
C18—H18	0.95	C13—H13	0.95
C6—C7	1.326 (3)	C26—H26	0.95
C6—H6	0.95	N2—H2	0.88
C19—C20	1.333 (4)	N4—H4	0.88
N1—C1—H1A	109.5	C9—C8—N1	119.7 (2)
N1—C1—H1B	109.5	C13—C8—N1	119.6 (2)
H1A—C1—H1B	109.5	C26—C21—C22	120.5 (3)
N1—C1—H1C	109.5	C26—C21—N3	119.4 (2)
H1A—C1—H1C	109.5	C22—C21—N3	119.9 (2)
H1B—C1—H1C	109.5	C8—C9—C10	119.6 (2)
N3—C14—H14A	109.5	C8—C9—H9	120.2
N3—C14—H14B	109.5	C10—C9—H9	120.2
H14A—C14—H14B	109.5	C21—C22—C23	118.3 (3)
N3—C14—H14C	109.5	C21—C22—H22	120.8
H14A—C14—H14C	109.5	C23—C22—H22	120.8
H14B—C14—H14C	109.5	C9—C10—C11	120.1 (3)
N1—C2—N2	114.7 (2)	C9—C10—H10	119.9
N1—C2—S1	125.7 (2)	C11—C10—H10	119.9
N2—C2—S1	119.6 (2)	C24—C23—C22	120.3 (3)
N3—C15—N4	116.2 (2)	C24—C23—H23	119.8
N3—C15—S2	125.0 (2)	C22—C23—H23	119.8
N4—C15—S2	118.77 (19)	C12—C11—C10	120.0 (3)
O1—C3—N2	121.7 (2)	C12—C11—H11	120
O1—C3—C4	124.1 (2)	C10—C11—H11	120
N2—C3—C4	114.2 (2)	C25—C24—C23	119.9 (3)
O3—C16—N4	123.3 (2)	C25—C24—H24	120
O3—C16—C17	123.5 (2)	C23—C24—H24	120
N4—C16—C17	113.1 (2)	C11—C12—C13	120.3 (3)
C5—C4—O2	109.6 (2)	C11—C12—H12	119.9
C5—C4—C3	134.1 (2)	C13—C12—H12	119.9
O2—C4—C3	116.2 (2)	C24—C25—C26	120.7 (3)
C18—C17—O4	109.9 (2)	C24—C25—H25	119.7
C18—C17—C16	133.2 (2)	C26—C25—H25	119.7
O4—C17—C16	116.7 (2)	C12—C13—C8	119.3 (3)
C4—C5—C6	107.1 (2)	C12—C13—H13	120.4
C4—C5—H5	126.4	C8—C13—H13	120.4
C6—C5—H5	126.4	C25—C26—C21	120.2 (3)
C17—C18—C19	107.2 (2)	C25—C26—H26	119.9
C17—C18—H18	126.4	C21—C26—H26	119.9
C19—C18—H18	126.4	C7—O2—C4	106.06 (19)
C7—C6—C5	105.8 (2)	C20—O4—C17	105.79 (19)
C7—C6—H6	127.1	C2—N1—C8	122.3 (2)
C5—C6—H6	127.1	C2—N1—C1	120.6 (2)
C20—C19—C18	106.3 (2)	C8—N1—C1	116.8 (2)
C20—C19—H19	126.8	C15—N3—C21	124.2 (2)
C18—C19—H19	126.8	C15—N3—C14	118.7 (2)
C6—C7—O2	111.4 (2)	C21—N3—C14	116.0 (2)
C6—C7—H7	124.3	C3—N2—C2	122.2 (2)
O2—C7—H7	124.3	C3—N2—H2	118.9
C19—C20—O4	110.8 (2)	C2—N2—H2	118.9
C19—C20—H20	124.6	C16—N4—C15	123.24 (19)
O4—C20—H20	124.6	C16—N4—H4	118.4
C9—C8—C13	120.6 (3)	C15—N4—H4	118.4
O1—C3—C4—C5	156.2 (3)	N3—C21—C26—C25	−174.3 (2)
N2—C3—C4—C5	−23.3 (4)	C6—C7—O2—C4	−0.3 (3)
O1—C3—C4—O2	−20.7 (4)	C5—C4—O2—C7	−0.3 (3)
N2—C3—C4—O2	159.7 (2)	C3—C4—O2—C7	177.3 (2)
O3—C16—C17—C18	165.5 (3)	C19—C20—O4—C17	0.0 (3)
N4—C16—C17—C18	−11.8 (4)	C18—C17—O4—C20	0.4 (3)
O3—C16—C17—O4	−9.2 (4)	C16—C17—O4—C20	176.3 (2)
N4—C16—C17—O4	173.5 (2)	N2—C2—N1—C8	−14.4 (3)
O2—C4—C5—C6	0.8 (3)	S1—C2—N1—C8	166.46 (18)
C3—C4—C5—C6	−176.3 (3)	N2—C2—N1—C1	170.9 (2)
O4—C17—C18—C19	−0.7 (3)	S1—C2—N1—C1	−8.2 (3)
C16—C17—C18—C19	−175.7 (3)	C9—C8—N1—C2	126.6 (3)
C4—C5—C6—C7	−0.9 (3)	C13—C8—N1—C2	−56.9 (3)
C17—C18—C19—C20	0.7 (3)	C9—C8—N1—C1	−58.6 (3)
C5—C6—C7—O2	0.8 (3)	C13—C8—N1—C1	118.0 (3)
C18—C19—C20—O4	−0.4 (3)	N4—C15—N3—C21	19.3 (3)
C13—C8—C9—C10	1.4 (4)	S2—C15—N3—C21	−161.15 (19)
N1—C8—C9—C10	177.9 (2)	N4—C15—N3—C14	−173.3 (2)
C26—C21—C22—C23	−0.2 (4)	S2—C15—N3—C14	6.2 (3)
N3—C21—C22—C23	175.1 (2)	C26—C21—N3—C15	−129.9 (3)
C8—C9—C10—C11	−0.3 (4)	C22—C21—N3—C15	54.7 (3)
C21—C22—C23—C24	−0.7 (4)	C26—C21—N3—C14	62.4 (3)
C9—C10—C11—C12	−0.2 (4)	C22—C21—N3—C14	−112.9 (3)
C22—C23—C24—C25	0.7 (5)	O1—C3—N2—C2	0.3 (4)
C10—C11—C12—C13	−0.4 (4)	C4—C3—N2—C2	179.9 (2)
C23—C24—C25—C26	0.1 (5)	N1—C2—N2—C3	−66.0 (3)
C11—C12—C13—C8	1.4 (4)	S1—C2—N2—C3	113.1 (2)
C9—C8—C13—C12	−2.0 (4)	O3—C16—N4—C15	−21.2 (4)
N1—C8—C13—C12	−178.5 (2)	C17—C16—N4—C15	156.1 (2)
C24—C25—C26—C21	−1.0 (4)	N3—C15—N4—C16	61.9 (3)
C22—C21—C26—C25	1.0 (4)	S2—C15—N4—C16	−117.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3i	0.88	2.54	3.331 (3)	149
N4—H4···O1ii	0.88	2.17	3.010 (2)	159
C5—H5···O3i	0.95	2.43	3.341 (3)	161
C5—H5···O4i	0.95	2.46	3.137 (3)	128
C14—H14C···O2	0.98	2.59	3.227 (4)	123
C18—H18···O1ii	0.95	2.44	3.274 (3)	147
C18—H18···O2ii	0.95	2.55	3.167 (3)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3i	0.88	2.54	3.331 (3)	149
N4—H4⋯O1ii	0.88	2.17	3.010 (2)	159

Symmetry codes: (i) ; (ii) .