Crystal structure of 3-(prop-2-en-1-yl)-1-{[(1E)-1,2,3,4-tetra­hydro­naphthalen-1-yl­idene]amino}­thio­urea

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Hassan, A.A.; Abdel-Aziz, A.T.; Albayati, M.R.

doi:10.1107/S2056989015021076

organic compounds

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Volume 71| Part 12| December 2015| Pages o976-o977

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Crystal structure of 3-(prop-2-en-1-yl)-1-{[(1E)-1,2,3,4-tetrahydronaphthalen-1-ylidene]amino}thiourea

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Alaa A Hassan,^c Ahmed T. Abdel-Aziz ^c and Mustafa R. Albayati ^e ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bFaculty of Science & Engineering, School of Healthcare Science, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^eKirkuk University, College of Education, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 5 November 2015; accepted 5 November 2015; online 21 November 2015)

In the title compound, C₁₄H₁₇N₃S, the dihedral angle between the planes of the benzene ring and the thiosemicarbazone group (r.m.s. deviation = 0.031 Å) is 8.45 (4)°. A short intramolcular N—H⋯N contact is seen. In the crystal, weak N—H⋯S hydrogen bonds connect the molecules into C(4) chains propagating in the [010] direction, with adjacent molecules in the chain related by 2₁ screw-axis symmetry.

Keywords: thiosemicarbazone; crystal structure; N—H⋯S hydrogen bond.

CCDC reference: 1435398

1. Related literature

For a related structure and background to thiosemicarbazones, see: Mohamed et al. (2015 ). For further synthetic details, see: Mague et al. (2014 ).

2. Experimental

2.1. Crystal data

C₁₄H₁₇N₃S
M_r = 259.36
Monoclinic, P 2₁ /n
a = 7.6665 (2) Å
b = 8.5788 (2) Å
c = 20.4072 (5) Å
β = 91.794 (1)°
V = 1341.51 (6) Å³
Z = 4
Cu Kα radiation
μ = 2.02 mm⁻¹
T = 150 K
0.20 × 0.19 × 0.16 mm

2.2. Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ) T_min = 0.68, T_max = 0.73
10141 measured reflections
2687 independent reflections
2486 reflections with I > 2σ(I)
R_int = 0.022

2.3. Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.084
S = 1.07
2687 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N3	0.91	2.17	2.6146 (13)	109
N1—H1N⋯S1ⁱ	0.91	2.82	3.4642 (11)	129
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT; program(s) used to solve structure: SHELXT (Bruker, 2014); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: SHELXTL (Bruker, 2014).

Supporting information

CCDC reference: 1435398

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015021076/hb7539sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015021076/hb7539Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015021076/hb7539Isup3.cml

checkCIF report

Related literature top

For a related structure and background to thiosemicarbazones, see: Mohamed et al. (2015). For further synthetic details, see: (Mague et al. (2014).

Experimental top

The title compound was prepared according to our recently reported method (Mague et al., 2014). Colourless blocks were recrystallised from ethanol solution. M.p. 393–394 K, 92% yield.

Structure description top

For a related structure and background to thiosemicarbazones, see: Mohamed et al. (2015). For further synthetic details, see: (Mague et al. (2014).

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Bruker, 2014); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Bruker, 2014).

Figures top

	Fig. 1. The title molecule with 50% probability displacement ellipsoids.
	Fig. 2. Packing viewed down the a axis.

3-(Prop-2-en-1-yl)-1-{[(1E)-1,2,3,4-tetrahydronaphthalen-1-ylidene]amino}thiourea top

Crystal data top

C₁₄H₁₇N₃S	F(000) = 552
M_r = 259.36	D_x = 1.284 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 7.6665 (2) Å	Cell parameters from 8207 reflections
b = 8.5788 (2) Å	θ = 4.3–74.5°
c = 20.4072 (5) Å	µ = 2.02 mm⁻¹
β = 91.794 (1)°	T = 150 K
V = 1341.51 (6) Å³	Block, colourless
Z = 4	0.20 × 0.19 × 0.16 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2687 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2486 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.022
Detector resolution: 10.4167 pixels mm^-1	θ_max = 74.5°, θ_min = 4.3°
ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −10→10
T_min = 0.68, T_max = 0.73	l = −21→25
10141 measured reflections

Refinement top

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)] = 0.031	Hydrogen site location: mixed
wR(F²) = 0.084	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0458P)² + 0.3454P] where P = (F_o² + 2F_c²)/3
2687 reflections	(Δ/σ)_max = 0.001
163 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₁₇N₃S	V = 1341.51 (6) Å³
M_r = 259.36	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 7.6665 (2) Å	µ = 2.02 mm⁻¹
b = 8.5788 (2) Å	T = 150 K
c = 20.4072 (5) Å	0.20 × 0.19 × 0.16 mm
β = 91.794 (1)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2687 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	2486 reflections with I > 2σ(I)
T_min = 0.68, T_max = 0.73	R_int = 0.022
10141 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.07	Δρ_max = 0.25 e Å⁻³
2687 reflections	Δρ_min = −0.24 e Å⁻³
163 parameters

Special details top

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å) while those attached to nitrogen were placed in locations derived from a difference map and their parameters adjusted to give N—H = 0.91 Å. All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.48923 (4)	0.32351 (4)	0.80129 (2)	0.03037 (11)
N1	0.24491 (13)	0.48661 (13)	0.73353 (5)	0.0280 (2)
H1N	0.2236	0.5554	0.7003	0.034*
N2	0.51325 (12)	0.47130 (12)	0.68903 (5)	0.0239 (2)
H2N	0.6272	0.4415	0.6911	0.029*
N3	0.44987 (12)	0.56539 (11)	0.63901 (4)	0.0220 (2)
C1	−0.0358 (2)	0.27861 (18)	0.69916 (8)	0.0472 (4)
H1A	0.0572	0.2901	0.6699	0.057*
H1B	−0.1320	0.2131	0.6878	0.057*
C2	−0.03150 (17)	0.35274 (17)	0.75504 (7)	0.0348 (3)
H2	−0.1277	0.3373	0.7826	0.042*
C3	0.10929 (16)	0.45938 (16)	0.78005 (6)	0.0299 (3)
H3A	0.0565	0.5606	0.7917	0.036*
H3B	0.1628	0.4143	0.8206	0.036*
C4	0.40678 (15)	0.43269 (13)	0.73855 (5)	0.0234 (2)
C5	0.55646 (14)	0.60710 (13)	0.59461 (5)	0.0203 (2)
C6	0.74503 (15)	0.55855 (14)	0.59361 (6)	0.0249 (2)
H6A	0.7515	0.4483	0.5795	0.030*
H6B	0.7964	0.5655	0.6386	0.030*
C7	0.85274 (15)	0.65815 (15)	0.54803 (6)	0.0265 (3)
H7A	0.8674	0.7639	0.5669	0.032*
H7B	0.9700	0.6114	0.5440	0.032*
C8	0.76392 (16)	0.66981 (15)	0.48046 (6)	0.0279 (3)
H8A	0.8331	0.7386	0.4522	0.033*
H8B	0.7588	0.5652	0.4600	0.033*
C9	0.58186 (15)	0.73399 (13)	0.48518 (5)	0.0235 (2)
C10	0.50909 (18)	0.82536 (14)	0.43472 (6)	0.0293 (3)
H10	0.5748	0.8447	0.3969	0.035*
C11	0.34410 (18)	0.88813 (14)	0.43851 (6)	0.0323 (3)
H11	0.2971	0.9499	0.4036	0.039*
C12	0.24694 (17)	0.86062 (14)	0.49371 (6)	0.0299 (3)
H12	0.1333	0.9037	0.4966	0.036*
C13	0.31603 (15)	0.77037 (13)	0.54449 (6)	0.0244 (2)
H13	0.2494	0.7522	0.5822	0.029*
C14	0.48339 (15)	0.70551 (13)	0.54080 (5)	0.0208 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02807 (18)	0.03706 (19)	0.02591 (18)	−0.00248 (11)	−0.00050 (12)	0.01231 (11)
N1	0.0248 (5)	0.0385 (6)	0.0208 (5)	−0.0010 (4)	0.0016 (4)	0.0074 (4)
N2	0.0233 (5)	0.0280 (5)	0.0204 (5)	−0.0003 (4)	0.0011 (4)	0.0048 (4)
N3	0.0247 (5)	0.0240 (5)	0.0173 (4)	−0.0012 (4)	−0.0001 (4)	0.0013 (3)
C1	0.0498 (9)	0.0378 (8)	0.0528 (9)	−0.0060 (7)	−0.0182 (7)	0.0063 (7)
C2	0.0252 (6)	0.0413 (7)	0.0378 (7)	−0.0005 (5)	−0.0005 (5)	0.0176 (6)
C3	0.0288 (6)	0.0410 (7)	0.0203 (6)	0.0011 (5)	0.0056 (5)	0.0035 (5)
C4	0.0259 (6)	0.0247 (6)	0.0196 (5)	−0.0047 (4)	0.0001 (4)	−0.0001 (4)
C5	0.0228 (5)	0.0206 (5)	0.0176 (5)	−0.0034 (4)	−0.0004 (4)	−0.0024 (4)
C6	0.0223 (5)	0.0273 (6)	0.0249 (6)	−0.0018 (4)	0.0000 (4)	0.0021 (4)
C7	0.0216 (6)	0.0329 (6)	0.0250 (6)	−0.0057 (5)	0.0012 (5)	−0.0015 (5)
C8	0.0267 (6)	0.0362 (7)	0.0209 (6)	−0.0066 (5)	0.0043 (5)	−0.0025 (4)
C9	0.0278 (6)	0.0230 (5)	0.0198 (5)	−0.0077 (4)	0.0001 (4)	−0.0018 (4)
C10	0.0389 (7)	0.0298 (6)	0.0192 (6)	−0.0094 (5)	−0.0003 (5)	0.0019 (4)
C11	0.0450 (7)	0.0239 (6)	0.0272 (6)	−0.0038 (5)	−0.0098 (5)	0.0041 (5)
C12	0.0315 (6)	0.0237 (6)	0.0339 (7)	0.0025 (5)	−0.0068 (5)	−0.0013 (5)
C13	0.0263 (6)	0.0233 (5)	0.0235 (6)	−0.0024 (4)	0.0005 (4)	−0.0016 (4)
C14	0.0238 (5)	0.0198 (5)	0.0186 (5)	−0.0039 (4)	−0.0014 (4)	−0.0018 (4)

Geometric parameters (Å, º) top

S1—C4	1.6928 (12)	C6—H6A	0.9900
N1—C4	1.3254 (16)	C6—H6B	0.9900
N1—C3	1.4487 (16)	C7—C8	1.5220 (16)
N1—H1N	0.9098	C7—H7A	0.9900
N2—C4	1.3597 (15)	C7—H7B	0.9900
N2—N3	1.3778 (13)	C8—C9	1.5063 (17)
N2—H2N	0.9098	C8—H8A	0.9900
N3—C5	1.2897 (15)	C8—H8B	0.9900
C1—C2	1.305 (2)	C9—C10	1.3964 (17)
C1—H1A	0.9500	C9—C14	1.4042 (16)
C1—H1B	0.9500	C10—C11	1.379 (2)
C2—C3	1.4926 (19)	C10—H10	0.9500
C2—H2	0.9500	C11—C12	1.390 (2)
C3—H3A	0.9900	C11—H11	0.9500
C3—H3B	0.9900	C12—C13	1.3854 (17)
C5—C14	1.4811 (15)	C12—H12	0.9500
C5—C6	1.5052 (16)	C13—C14	1.4027 (16)
C6—C7	1.5249 (16)	C13—H13	0.9500

C4—N1—C3	125.63 (10)	C8—C7—C6	110.73 (10)
C4—N1—H1N	115.4	C8—C7—H7A	109.5
C3—N1—H1N	118.5	C6—C7—H7A	109.5
C4—N2—N3	119.17 (10)	C8—C7—H7B	109.5
C4—N2—H2N	119.7	C6—C7—H7B	109.5
N3—N2—H2N	121.0	H7A—C7—H7B	108.1
C5—N3—N2	117.81 (10)	C9—C8—C7	110.81 (10)
C2—C1—H1A	120.0	C9—C8—H8A	109.5
C2—C1—H1B	120.0	C7—C8—H8A	109.5
H1A—C1—H1B	120.0	C9—C8—H8B	109.5
C1—C2—C3	126.56 (14)	C7—C8—H8B	109.5
C1—C2—H2	116.7	H8A—C8—H8B	108.1
C3—C2—H2	116.7	C10—C9—C14	118.77 (11)
N1—C3—C2	113.63 (11)	C10—C9—C8	120.51 (11)
N1—C3—H3A	108.8	C14—C9—C8	120.71 (10)
C2—C3—H3A	108.8	C11—C10—C9	121.58 (12)
N1—C3—H3B	108.8	C11—C10—H10	119.2
C2—C3—H3B	108.8	C9—C10—H10	119.2
H3A—C3—H3B	107.7	C10—C11—C12	119.66 (11)
N1—C4—N2	116.10 (10)	C10—C11—H11	120.2
N1—C4—S1	125.31 (9)	C12—C11—H11	120.2
N2—C4—S1	118.58 (9)	C13—C12—C11	119.94 (12)
N3—C5—C14	116.47 (10)	C13—C12—H12	120.0
N3—C5—C6	124.24 (10)	C11—C12—H12	120.0
C14—C5—C6	119.26 (10)	C12—C13—C14	120.69 (11)
C5—C6—C7	113.07 (10)	C12—C13—H13	119.7
C5—C6—H6A	109.0	C14—C13—H13	119.7
C7—C6—H6A	109.0	C13—C14—C9	119.35 (10)
C5—C6—H6B	109.0	C13—C14—C5	120.78 (10)
C7—C6—H6B	109.0	C9—C14—C5	119.87 (10)
H6A—C6—H6B	107.8

C4—N2—N3—C5	176.28 (10)	C14—C9—C10—C11	0.25 (17)
C4—N1—C3—C2	−109.16 (14)	C8—C9—C10—C11	−178.62 (11)
C1—C2—C3—N1	4.4 (2)	C9—C10—C11—C12	0.07 (18)
C3—N1—C4—N2	179.56 (11)	C10—C11—C12—C13	−0.07 (18)
C3—N1—C4—S1	−1.23 (18)	C11—C12—C13—C14	−0.26 (18)
N3—N2—C4—N1	1.89 (16)	C12—C13—C14—C9	0.58 (17)
N3—N2—C4—S1	−177.38 (8)	C12—C13—C14—C5	−179.10 (10)
N2—N3—C5—C14	178.78 (9)	C10—C9—C14—C13	−0.57 (16)
N2—N3—C5—C6	0.54 (16)	C8—C9—C14—C13	178.30 (10)
N3—C5—C6—C7	−163.89 (11)	C10—C9—C14—C5	179.12 (10)
C14—C5—C6—C7	17.91 (14)	C8—C9—C14—C5	−2.02 (16)
C5—C6—C7—C8	−50.50 (14)	N3—C5—C14—C13	10.37 (15)
C6—C7—C8—C9	56.66 (13)	C6—C5—C14—C13	−171.29 (10)
C7—C8—C9—C10	147.83 (11)	N3—C5—C14—C9	−169.31 (10)
C7—C8—C9—C14	−31.02 (15)	C6—C5—C14—C9	9.03 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N3	0.91	2.17	2.6146 (13)	109
N1—H1N···S1ⁱ	0.91	2.82	3.4642 (11)	129

Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N3	0.91	2.17	2.6146 (13)	109
N1—H1N···S1ⁱ	0.91	2.82	3.4642 (11)	129

Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.

Acknowledgements

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2014). APEX2, SAINT, SADABS, SHELXT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Mague, J. T., Mohamed, S. K., Akkurt, M., Hassan, A. A. & Albayati, M. R. (2014). Acta Cryst. E70, o515. CSD CrossRef IUCr Journals Google Scholar
Mohamed, S. K., Mague, J. T., Akkurt, M., Hassan, A. A., Abdel-Aziz, A. T. & Albayati, M. R. (2015). Acta Cryst. E71, o974–o975. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 3-(prop-2-en-1-yl)-1-{[(1E)-1,2,3,4-tetra­hydro­naphthalen-1-yl­­idene]amino}­thio­urea

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 3-(prop-2-en-1-yl)-1-{[(1E)-1,2,3,4-tetrahydronaphthalen-1-ylidene]amino}thiourea