1-[2-(4-Isobutyl-phen-yl)propano-yl]thiosemicarbazide.

In the title compound, C(14)H(21)N(3)OS, inter-molecular N-H⋯O inter-actions generate ten-membered rings with R(2) (2)(10) ring motifs, whereas N-H⋯S inter-actions generate eight, 14- and 16-membered rings with R(2) (2)(8), R(4) (4)(14) and R(4) (4)(16) ring motifs, respectively. There are weak intra-molecular N-H⋯π inter-actions which might influence the conformation of the mol-ecule. The compound has a stereogenic center but the space group is centrosymmetic so the mol-ecule exists as a racemate.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For biomedical applications of non-steroidal anti-inflammatory drugs, see, for example; Kawail et al. (2005 ▶); Klasser & Epstein (2005 ▶); Kean & Buchanan (2005 ▶); Nielsen & Bundgaard (1988 ▶); Khan & Akhter (2005 ▶); Zhao et al. (2006 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H21N3OS

M = 279.40

Triclinic,

a = 5.5347 (1) Å

b = 10.6209 (3) Å

c = 13.1435 (3) Å

α = 97.935 (1)°

β = 98.418 (1)°

γ = 96.293 (1)°

V = 750.30 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 100 K

0.54 × 0.32 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.894, T max = 0.969

18596 measured reflections

6524 independent reflections

5896 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.096

S = 1.05

6524 reflections

191 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.68 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006527/dn2428sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006527/dn2428Isup2.hkl

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

C14H21N3OS	Z = 2
Mr = 279.40	F(000) = 300
Triclinic, P1	Dx = 1.237 Mg m−3
Hall symbol: -P 1	Melting point: 335 K
a = 5.5347 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6209 (3) Å	Cell parameters from 9906 reflections
c = 13.1435 (3) Å	θ = 2.3–38.2°
α = 97.935 (1)°	µ = 0.21 mm−1
β = 98.418 (1)°	T = 100 K
γ = 96.293 (1)°	Block, colourless
V = 750.30 (3) Å3	0.54 × 0.32 × 0.15 mm

Bruker SMART APEXII CCD area-detector diffractometer	6524 independent reflections
Radiation source: fine-focus sealed tube	5896 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 35.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.894, Tmax = 0.969	k = −16→17
18596 measured reflections	l = −20→21

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.1966P] where P = (Fo2 + 2Fc2)/3
6524 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.68 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
S1	0.30182 (3)	0.806105 (17)	0.407445 (14)	0.01523 (5)
O1	0.65430 (10)	0.57112 (5)	0.62717 (5)	0.01802 (10)
N1	0.87208 (11)	0.64109 (6)	0.50767 (5)	0.01429 (10)
N2	0.66238 (12)	0.66716 (6)	0.44588 (5)	0.01530 (11)
N3	0.74599 (12)	0.87876 (6)	0.52340 (5)	0.01701 (11)
C1	0.95446 (14)	0.81565 (7)	0.78524 (6)	0.01651 (12)
H1A	0.8281	0.7578	0.8019	0.020*
C2	0.96885 (14)	0.94657 (7)	0.82013 (6)	0.01724 (12)
H2A	0.8519	0.9769	0.8604	0.021*
C3	1.15276 (14)	1.03429 (7)	0.79679 (6)	0.01707 (12)
C4	1.32484 (15)	0.98630 (8)	0.73933 (6)	0.01981 (14)
H4A	1.4534	1.0439	0.7239	0.024*
C5	1.31130 (14)	0.85529 (8)	0.70412 (6)	0.01828 (13)
H5A	1.4303	0.8249	0.6650	0.022*
C6	1.12491 (13)	0.76844 (7)	0.72571 (5)	0.01440 (11)
C7	1.09656 (13)	0.62723 (7)	0.67782 (6)	0.01577 (12)
H7A	1.2328	0.6134	0.6369	0.019*
C8	0.85365 (13)	0.60673 (6)	0.60322 (6)	0.01385 (11)
C9	0.58753 (12)	0.78460 (6)	0.46377 (5)	0.01334 (11)
C10	1.16404 (17)	1.17610 (7)	0.83421 (6)	0.02134 (14)
H10A	0.9976	1.2013	0.8173	0.026*
H10B	1.2750	1.2240	0.7960	0.026*
C11	1.25548 (16)	1.21505 (8)	0.95183 (6)	0.02091 (14)
H11A	1.1465	1.1631	0.9893	0.025*
C12	1.5176 (2)	1.18766 (13)	0.98222 (10)	0.0422 (3)
H12A	1.5659	1.2084	1.0580	0.063*
H12B	1.6290	1.2402	0.9485	0.063*
H12C	1.5271	1.0967	0.9598	0.063*
C13	1.2345 (2)	1.35641 (8)	0.98524 (8)	0.02918 (18)
H13A	1.2943	1.3802	1.0601	0.044*
H13B	1.0617	1.3706	0.9700	0.044*
H13C	1.3339	1.4091	0.9470	0.044*
C14	1.09915 (18)	0.53538 (8)	0.75758 (7)	0.02360 (15)
H14A	1.2581	0.5521	0.8044	0.035*
H14B	1.0747	0.4467	0.7214	0.035*
H14C	0.9664	0.5484	0.7982	0.035*
H1N2	0.556 (3)	0.6019 (14)	0.4190 (11)	0.027 (3)*
H1N1	1.013 (2)	0.6698 (13)	0.4891 (10)	0.024 (3)*
H2N3	0.888 (3)	0.8658 (13)	0.5509 (11)	0.029 (3)*
H1N3	0.703 (3)	0.9524 (14)	0.5348 (11)	0.027 (3)*

	U11	U22	U33	U12	U13	U23
S1	0.01232 (8)	0.01386 (8)	0.01930 (9)	0.00173 (5)	0.00039 (6)	0.00418 (6)
O1	0.0155 (2)	0.0151 (2)	0.0225 (3)	−0.00111 (18)	0.00474 (19)	0.00054 (19)
N1	0.0111 (2)	0.0143 (2)	0.0172 (2)	0.00244 (18)	0.00100 (19)	0.00253 (19)
N2	0.0134 (2)	0.0117 (2)	0.0190 (3)	0.00211 (19)	−0.0017 (2)	0.00032 (19)
N3	0.0137 (2)	0.0116 (2)	0.0239 (3)	0.00168 (19)	−0.0009 (2)	0.0003 (2)
C1	0.0146 (3)	0.0140 (3)	0.0202 (3)	0.0002 (2)	0.0040 (2)	0.0003 (2)
C2	0.0164 (3)	0.0145 (3)	0.0197 (3)	0.0017 (2)	0.0028 (2)	−0.0006 (2)
C3	0.0196 (3)	0.0145 (3)	0.0151 (3)	−0.0006 (2)	−0.0012 (2)	0.0020 (2)
C4	0.0206 (3)	0.0196 (3)	0.0175 (3)	−0.0040 (3)	0.0034 (2)	0.0018 (2)
C5	0.0153 (3)	0.0213 (3)	0.0169 (3)	−0.0004 (2)	0.0033 (2)	−0.0002 (2)
C6	0.0127 (3)	0.0145 (3)	0.0149 (3)	0.0020 (2)	0.0002 (2)	0.0005 (2)
C7	0.0147 (3)	0.0148 (3)	0.0173 (3)	0.0043 (2)	0.0008 (2)	0.0007 (2)
C8	0.0141 (3)	0.0098 (2)	0.0168 (3)	0.0020 (2)	0.0019 (2)	−0.0004 (2)
C9	0.0128 (3)	0.0121 (2)	0.0152 (3)	0.0012 (2)	0.0025 (2)	0.0026 (2)
C10	0.0288 (4)	0.0131 (3)	0.0194 (3)	−0.0001 (3)	−0.0021 (3)	0.0019 (2)
C11	0.0263 (4)	0.0156 (3)	0.0185 (3)	−0.0009 (3)	0.0011 (3)	0.0004 (2)
C12	0.0356 (5)	0.0422 (6)	0.0389 (6)	0.0109 (5)	−0.0156 (4)	−0.0103 (5)
C13	0.0385 (5)	0.0165 (3)	0.0286 (4)	−0.0021 (3)	0.0034 (4)	−0.0032 (3)
C14	0.0315 (4)	0.0181 (3)	0.0212 (3)	0.0078 (3)	0.0000 (3)	0.0044 (3)

S1—C9	1.6982 (7)	C5—H5A	0.9500
O1—C8	1.2259 (9)	C6—C7	1.5261 (10)
N1—C8	1.3699 (10)	C7—C8	1.5190 (10)
N1—N2	1.3927 (9)	C7—C14	1.5270 (11)
N1—H1N1	0.884 (14)	C7—H7A	1.0000
N2—C9	1.3578 (9)	C10—C11	1.5381 (12)
N2—H1N2	0.855 (15)	C10—H10A	0.9900
N3—C9	1.3318 (9)	C10—H10B	0.9900
N3—H2N3	0.851 (14)	C11—C12	1.5178 (14)
N3—H1N3	0.843 (14)	C11—C13	1.5269 (12)
C1—C2	1.3925 (10)	C11—H11A	1.0000
C1—C6	1.4019 (10)	C12—H12A	0.9800
C1—H1A	0.9500	C12—H12B	0.9800
C2—C3	1.4002 (11)	C12—H12C	0.9800
C2—H2A	0.9500	C13—H13A	0.9800
C3—C4	1.3957 (12)	C13—H13B	0.9800
C3—C10	1.5100 (11)	C13—H13C	0.9800
C4—C5	1.3947 (11)	C14—H14A	0.9800
C4—H4A	0.9500	C14—H14B	0.9800
C5—C6	1.3946 (11)	C14—H14C	0.9800
C8—N1—N2	119.30 (6)	N1—C8—C7	114.12 (6)
C8—N1—H1N1	123.8 (9)	N3—C9—N2	117.81 (6)
N2—N1—H1N1	114.5 (8)	N3—C9—S1	123.05 (5)
C9—N2—N1	119.39 (6)	N2—C9—S1	119.12 (5)
C9—N2—H1N2	119.6 (9)	C3—C10—C11	113.56 (6)
N1—N2—H1N2	115.4 (9)	C3—C10—H10A	108.9
C9—N3—H2N3	121.5 (10)	C11—C10—H10A	108.9
C9—N3—H1N3	118.9 (10)	C3—C10—H10B	108.9
H2N3—N3—H1N3	119.6 (13)	C11—C10—H10B	108.9
C2—C1—C6	120.56 (7)	H10A—C10—H10B	107.7
C2—C1—H1A	119.7	C12—C11—C13	110.83 (8)
C6—C1—H1A	119.7	C12—C11—C10	111.70 (8)
C1—C2—C3	121.12 (7)	C13—C11—C10	110.21 (7)
C1—C2—H2A	119.4	C12—C11—H11A	108.0
C3—C2—H2A	119.4	C13—C11—H11A	108.0
C4—C3—C2	117.97 (7)	C10—C11—H11A	108.0
C4—C3—C10	121.57 (7)	C11—C12—H12A	109.5
C2—C3—C10	120.45 (7)	C11—C12—H12B	109.5
C5—C4—C3	121.16 (7)	H12A—C12—H12B	109.5
C5—C4—H4A	119.4	C11—C12—H12C	109.5
C3—C4—H4A	119.4	H12A—C12—H12C	109.5
C6—C5—C4	120.71 (7)	H12B—C12—H12C	109.5
C6—C5—H5A	119.6	C11—C13—H13A	109.5
C4—C5—H5A	119.6	C11—C13—H13B	109.5
C5—C6—C1	118.45 (7)	H13A—C13—H13B	109.5
C5—C6—C7	120.22 (6)	C11—C13—H13C	109.5
C1—C6—C7	121.14 (6)	H13A—C13—H13C	109.5
C8—C7—C6	104.02 (5)	H13B—C13—H13C	109.5
C8—C7—C14	112.04 (7)	C7—C14—H14A	109.5
C6—C7—C14	113.91 (6)	C7—C14—H14B	109.5
C8—C7—H7A	108.9	H14A—C14—H14B	109.5
C6—C7—H7A	108.9	C7—C14—H14C	109.5
C14—C7—H7A	108.9	H14A—C14—H14C	109.5
O1—C8—N1	121.87 (7)	H14B—C14—H14C	109.5
O1—C8—C7	123.83 (7)
C8—N1—N2—C9	81.80 (8)	C1—C6—C7—C14	−59.88 (9)
C6—C1—C2—C3	0.06 (12)	N2—N1—C8—O1	16.17 (10)
C1—C2—C3—C4	−1.36 (11)	N2—N1—C8—C7	−159.10 (6)
C1—C2—C3—C10	179.31 (7)	C6—C7—C8—O1	−91.51 (8)
C2—C3—C4—C5	1.40 (12)	C14—C7—C8—O1	31.97 (10)
C10—C3—C4—C5	−179.28 (7)	C6—C7—C8—N1	83.65 (7)
C3—C4—C5—C6	−0.13 (12)	C14—C7—C8—N1	−152.87 (6)
C4—C5—C6—C1	−1.19 (11)	N1—N2—C9—N3	14.79 (10)
C4—C5—C6—C7	173.91 (7)	N1—N2—C9—S1	−166.70 (5)
C2—C1—C6—C5	1.22 (11)	C4—C3—C10—C11	−106.27 (9)
C2—C1—C6—C7	−173.83 (7)	C2—C3—C10—C11	73.03 (10)
C5—C6—C7—C8	−112.59 (7)	C3—C10—C11—C12	62.58 (11)
C1—C6—C7—C8	62.37 (8)	C3—C10—C11—C13	−173.75 (8)
C5—C6—C7—C14	125.16 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1i	0.857 (15)	2.029 (15)	2.8745 (9)	169.0 (14)
N1—H1N1···S1ii	0.886 (12)	2.495 (13)	3.3324 (7)	157.8 (11)
N3—H1N3···S1iii	0.842 (15)	2.577 (15)	3.3945 (7)	164.1 (14)
C7—H7A···O1ii	1.00	2.44	3.3501 (9)	151
N3—H2N3···Cg1	0.850 (16)	2.870 (14)	3.5083 (7)	133.4 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1i	0.857 (15)	2.029 (15)	2.8745 (9)	169.0 (14)
N1—H1N1⋯S1ii	0.886 (12)	2.495 (13)	3.3324 (7)	157.8 (11)
N3—H1N3⋯S1iii	0.842 (15)	2.577 (15)	3.3945 (7)	164.1 (14)
C7—H7A⋯O1ii	1.00	2.44	3.3501 (9)	151
N3—H2N3⋯Cg1	0.850 (16)	2.870 (14)	3.5083 (7)	133.4 (12)

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C1–C6 benzene ring.