(2E)-2-[2-(Cyclo-hexyl-carbamothio-yl)hydrazinylidene]-propanoic acid.

In the title thio-urea derivative, C(10)H(17)N(3)O(2)S, the carboxyl group and the least-squares plane through the cyclo-hexyl ring are twisted out of the plane through the central CN(3)S residue; the respective dihedral angles are 7.18 (8) and 62.29 (4)°. The conformation about the azomethine bond [1.275 (2) Å] is E. The NH groups are anti, with one forming an intra-molecular N-H⋯N hydrogen bond. The main feature of the crystal structure is the formation of linear supra-molecular chains along [110] mediated by alternating pairs of O-H⋯O and pairs of N-H⋯S hydrogen bonds.

Related literature

For related thio­urea structures, see: Normaya et al. (2011 ▶); n class="Species">Salam et al. (2011 ▶).

Experimental

Crystal data

C10H17N3O2S

M = 243.33

Monoclinic,

a = 8.9204 (2) Å

b = 6.0350 (2) Å

c = 22.4750 (6) Å

β = 90.051 (3)°

V = 1209.93 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 100 K

0.30 × 0.20 × 0.10 mm

Data collection

Agilent Supernova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.687, T max = 1.000

7394 measured reflections

2723 independent reflections

2251 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.143

S = 0.98

2723 reflections

158 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014449/hb5851sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014449/hb5851Isup2.hkl

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

C10H17N3O2S	F(000) = 520
Mr = 243.33	Dx = 1.336 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3312 reflections
a = 8.9204 (2) Å	θ = 2.3–29.1°
b = 6.0350 (2) Å	µ = 0.26 mm−1
c = 22.4750 (6) Å	T = 100 K
β = 90.051 (3)°	Prism, colourless
V = 1209.93 (6) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Agilent Supernova Dual diffractometer with an Atlas detector	2723 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2251 reflections with I > 2σ(I)
Mirror	Rint = 0.036
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −6→7
Tmin = 0.687, Tmax = 1.000	l = −29→29
7394 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2723 reflections	(Δ/σ)max = 0.001
158 parameters	Δρmax = 0.36 e Å−3
3 restraints	Δρmin = −0.32 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.

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	1.07001 (5)	1.46426 (7)	0.59008 (2)	0.01940 (18)
O1	0.65476 (14)	0.6300 (2)	0.54143 (6)	0.0209 (3)
O2	0.53180 (13)	0.7099 (2)	0.45694 (6)	0.0196 (3)
N1	0.80028 (16)	1.0010 (2)	0.53480 (7)	0.0156 (3)
N2	0.88614 (16)	1.1878 (2)	0.53543 (7)	0.0170 (3)
N3	0.94326 (16)	1.0938 (3)	0.63114 (7)	0.0169 (3)
C1	0.62814 (18)	0.7522 (3)	0.49413 (8)	0.0164 (4)
C2	0.72145 (19)	0.9564 (3)	0.48899 (8)	0.0162 (4)
C3	0.7098 (2)	1.0904 (3)	0.43363 (8)	0.0211 (4)
H3A	0.6904	1.2455	0.4440	0.032*
H3B	0.6273	1.0339	0.4091	0.032*
H3C	0.8039	1.0800	0.4113	0.032*
C4	0.96146 (18)	1.2376 (3)	0.58689 (8)	0.0156 (4)
C5	1.00682 (18)	1.1176 (3)	0.69060 (7)	0.0157 (4)
H5	1.1055	1.1951	0.6871	0.019*
C6	1.0336 (2)	0.8900 (3)	0.71759 (9)	0.0210 (4)
H6A	1.1037	0.8054	0.6921	0.025*
H6B	0.9377	0.8076	0.7194	0.025*
C7	1.0991 (2)	0.9113 (3)	0.78024 (8)	0.0221 (4)
H7A	1.1116	0.7618	0.7977	0.026*
H7B	1.1994	0.9811	0.7779	0.026*
C8	0.9984 (2)	1.0501 (3)	0.82063 (9)	0.0235 (4)
H8A	0.9019	0.9725	0.8267	0.028*
H8B	1.0471	1.0689	0.8599	0.028*
C9	0.9696 (2)	1.2771 (3)	0.79289 (9)	0.0250 (4)
H9A	0.8988	1.3610	0.8182	0.030*
H9B	1.0648	1.3611	0.7912	0.030*
C10	0.9048 (2)	1.2561 (3)	0.73033 (8)	0.0212 (4)
H10A	0.8046	1.1858	0.7325	0.025*
H10B	0.8924	1.4055	0.7128	0.025*
H1	0.602 (2)	0.514 (3)	0.5431 (12)	0.040 (7)*
H2	0.892 (2)	1.275 (3)	0.5035 (6)	0.026 (6)*
H3	0.888 (2)	0.976 (2)	0.6260 (11)	0.029 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0251 (3)	0.0177 (3)	0.0154 (3)	−0.00825 (16)	−0.0030 (2)	0.00088 (18)
O1	0.0233 (6)	0.0208 (7)	0.0185 (7)	−0.0089 (5)	−0.0048 (5)	0.0055 (6)
O2	0.0200 (6)	0.0205 (7)	0.0182 (7)	−0.0064 (5)	−0.0030 (5)	0.0018 (5)
N1	0.0148 (7)	0.0144 (7)	0.0178 (8)	−0.0030 (5)	0.0009 (6)	−0.0010 (6)
N2	0.0214 (7)	0.0140 (7)	0.0157 (8)	−0.0039 (6)	−0.0007 (6)	0.0036 (6)
N3	0.0196 (7)	0.0172 (7)	0.0140 (8)	−0.0068 (6)	−0.0047 (6)	0.0006 (6)
C1	0.0159 (8)	0.0178 (9)	0.0155 (9)	0.0010 (7)	0.0000 (7)	−0.0017 (7)
C2	0.0153 (8)	0.0168 (9)	0.0166 (9)	−0.0015 (6)	0.0005 (7)	0.0006 (7)
C3	0.0247 (9)	0.0215 (9)	0.0169 (9)	−0.0069 (7)	−0.0040 (7)	0.0022 (8)
C4	0.0154 (8)	0.0160 (8)	0.0155 (8)	−0.0002 (6)	0.0004 (7)	−0.0008 (7)
C5	0.0173 (8)	0.0184 (9)	0.0112 (8)	−0.0030 (7)	−0.0038 (6)	−0.0006 (7)
C6	0.0255 (9)	0.0168 (9)	0.0208 (9)	0.0006 (7)	0.0006 (8)	−0.0003 (8)
C7	0.0266 (9)	0.0186 (9)	0.0210 (10)	0.0007 (7)	−0.0032 (8)	0.0036 (8)
C8	0.0301 (10)	0.0263 (10)	0.0141 (9)	−0.0050 (8)	−0.0001 (8)	−0.0016 (8)
C9	0.0318 (10)	0.0241 (10)	0.0191 (9)	0.0032 (8)	−0.0004 (8)	−0.0057 (8)
C10	0.0255 (9)	0.0197 (9)	0.0185 (9)	0.0037 (7)	−0.0007 (8)	−0.0011 (8)

S1—C4	1.6774 (18)	C5—C10	1.525 (2)
O1—C1	1.315 (2)	C5—H5	1.0000
O1—H1	0.845 (10)	C6—C7	1.530 (3)
O2—C1	1.225 (2)	C6—H6A	0.9900
N1—C2	1.275 (2)	C6—H6B	0.9900
N1—N2	1.363 (2)	C7—C8	1.528 (3)
N2—C4	1.370 (2)	C7—H7A	0.9900
N2—H2	0.892 (9)	C7—H7B	0.9900
N3—C4	1.330 (2)	C8—C9	1.527 (3)
N3—C5	1.458 (2)	C8—H8A	0.9900
N3—H3	0.870 (9)	C8—H8B	0.9900
C1—C2	1.491 (2)	C9—C10	1.525 (3)
C2—C3	1.488 (3)	C9—H9A	0.9900
C3—H3A	0.9800	C9—H9B	0.9900
C3—H3B	0.9800	C10—H10A	0.9900
C3—H3C	0.9800	C10—H10B	0.9900
C5—C6	1.520 (3)
C1—O1—H1	113.7 (18)	C5—C6—H6A	109.5
C2—N1—N2	119.52 (15)	C7—C6—H6A	109.5
N1—N2—C4	117.71 (14)	C5—C6—H6B	109.5
N1—N2—H2	121.1 (14)	C7—C6—H6B	109.5
C4—N2—H2	121.2 (14)	H6A—C6—H6B	108.1
C4—N3—C5	124.97 (14)	C8—C7—C6	111.63 (15)
C4—N3—H3	120.2 (16)	C8—C7—H7A	109.3
C5—N3—H3	114.8 (16)	C6—C7—H7A	109.3
O2—C1—O1	124.08 (15)	C8—C7—H7B	109.3
O2—C1—C2	120.71 (15)	C6—C7—H7B	109.3
O1—C1—C2	115.18 (15)	H7A—C7—H7B	108.0
N1—C2—C3	126.77 (15)	C9—C8—C7	110.38 (16)
N1—C2—C1	114.80 (15)	C9—C8—H8A	109.6
C3—C2—C1	118.38 (15)	C7—C8—H8A	109.6
C2—C3—H3A	109.5	C9—C8—H8B	109.6
C2—C3—H3B	109.5	C7—C8—H8B	109.6
H3A—C3—H3B	109.5	H8A—C8—H8B	108.1
C2—C3—H3C	109.5	C10—C9—C8	111.43 (15)
H3A—C3—H3C	109.5	C10—C9—H9A	109.3
H3B—C3—H3C	109.5	C8—C9—H9A	109.3
N3—C4—N2	115.34 (15)	C10—C9—H9B	109.3
N3—C4—S1	124.83 (14)	C8—C9—H9B	109.3
N2—C4—S1	119.82 (13)	H9A—C9—H9B	108.0
N3—C5—C6	109.71 (14)	C5—C10—C9	111.06 (14)
N3—C5—C10	111.03 (14)	C5—C10—H10A	109.4
C6—C5—C10	110.79 (15)	C9—C10—H10A	109.4
N3—C5—H5	108.4	C5—C10—H10B	109.4
C6—C5—H5	108.4	C9—C10—H10B	109.4
C10—C5—H5	108.4	H10A—C10—H10B	108.0
C5—C6—C7	110.56 (15)
C2—N1—N2—C4	175.80 (15)	C4—N3—C5—C6	−151.10 (16)
N2—N1—C2—C3	−0.7 (3)	C4—N3—C5—C10	86.1 (2)
N2—N1—C2—C1	−178.00 (14)	N3—C5—C6—C7	−179.54 (14)
O2—C1—C2—N1	169.21 (15)	C10—C5—C6—C7	−56.59 (19)
O1—C1—C2—N1	−8.9 (2)	C5—C6—C7—C8	56.5 (2)
O2—C1—C2—C3	−8.4 (2)	C6—C7—C8—C9	−55.6 (2)
O1—C1—C2—C3	173.52 (15)	C7—C8—C9—C10	55.2 (2)
C5—N3—C4—N2	−177.12 (15)	N3—C5—C10—C9	178.84 (14)
C5—N3—C4—S1	4.2 (2)	C6—C5—C10—C9	56.7 (2)
N1—N2—C4—N3	0.7 (2)	C8—C9—C10—C5	−56.1 (2)
N1—N2—C4—S1	179.49 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N1	0.87 (1)	2.20 (2)	2.574 (2)	106.(2)
O1—H1···O2i	0.85 (1)	1.80 (1)	2.6416 (17)	172 (3)
N2—H2···S1ii	0.89 (1)	2.65 (1)	3.5384 (15)	176.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N1	0.87 (1)	2.20 (2)	2.574 (2)	106 (2)
O1—H1⋯O2i	0.85 (1)	1.80 (1)	2.6416 (17)	172 (3)
N2—H2⋯S1ii	0.89 (1)	2.65 (1)	3.5384 (15)	176 (2)

Symmetry codes: (i) ; (ii) .