1-(2-Furo­yl)-3-(1-naphth­yl)thio­urea

Duque, J.; Estevez-Hernandez, O.; Reguera, E.; Corrêa, R.S.; Gutierrez Maria, P.

doi:10.1107/S1600536808012208

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1068

doi:10.1107/S1600536808012208

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1-(2-Furoyl)-3-(1-naphthyl)thiourea

J. Duque,^a ^* Osvaldo Estevez-Hernandez,^a Edilso Reguera,^a Rodrigo S. Corrêa ^b and P. Gutierrez Maria ^c

^aDepartment of Structure Analysis, Institute of Materials, University of Havana, Cuba, ^bGrupo de Cristalografía, Instituto de Física de São Carlos, Universidade de São Paulo, São Carlos, Brazil, and ^cInstitute of Materials, UNAM, Av. Universidad No 3000 Col. Copilco el Alto, DF, Mexico
^*Correspondence e-mail: duque@imre.oc.uh.cu

(Received 24 April 2008; accepted 27 April 2008; online 14 May 2008)

In the title compound, C₁₆H₁₂N₂O₂S, the carbonylthiourea group forms dihedral angles of 75.4 (1) and 13.1 (2)°, respectively, with the naphthalene ring system and furan ring. The molecule adopts a trans–cis configuration with respect to the positions of the furoyl and naphthyl groups relative to the S atom across the thiourea C—N bonds. This geometry is stabilized by an N—H⋯·O intramolecular hydrogen bond. In the crystal structure, molecules are linked by N—H⋯S hydrogen bonds, forming centrosymmetric dimers which are interlinked through C—H⋯π interactions.

Related literature

For general background, see: Ashraf et al. (2007 ); Koch (2001 ). For related structures, see: Dago et al. (1987 ); Cao et al. (1996 ); Yuan et al. (1997 ); Kaminsky et al. (2002 ); Weiqun et al. (2003 ); Yamin & Hassan (2004 ). For the synthesis, see: Otazo et al. (2001 ).

Experimental

Crystal data

C₁₆H₁₂N₂O₂S
M_r = 296.34
Monoclinic, P 2₁ /c
a = 9.402 (2) Å
b = 19.082 (4) Å
c = 7.880 (2) Å
β = 94.94 (1)°
V = 1408.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 294 (2) K
0.50 × 0.25 × 0.05 mm

Data collection

Siemens P4 diffractometer
Absorption correction: none
3603 measured reflections
2771 independent reflections
1521 reflections with I > 2σ(I)
R_int = 0.043
3 standard reflections every 97 reflections intensity decay: 2.6%

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.131
S = 1.02
2771 reflections
239 parameters
All H-atom parameters refined
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86 (4)	2.00 (4)	2.698 (3)	138 (3)
N1—H1⋯S1ⁱ	0.91 (5)	2.57 (5)	3.455 (3)	164 (4)
C5—H5⋯Cg1ⁱⁱ	0.96 (4)	2.85 (4)	3.654 (4)	143 (3)
Symmetry codes: (i) -x+1, -y, -z+2; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ . Cg1 is the centroid of the C7–C11/C16 ring.

Data collection: XSCANS (Siemens, 1996 ); cell refinement: XSCANS; data reduction: XSCANS; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012208/ci2591sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012208/ci2591Isup2.hkl

checkCIF report

Comment top

The subject of aroylsubstituted thioureas is considered as a very interesting topic due to their remarkable optical and electronic properties (Ashraf et al.,2007). Substitutions that reduce the symmetry of the thiourea molecule enhance the non-linear optical properties. A variety of crystals of this class has been reported (Dago et al., 1987; Cao et al., 1996; Yuan et al., 1997; Kaminsky et al., 2002; Weiqun et al., 2003). The title compound (Fig.1) is another example of a newly synthesized furoylthiourea derivative.

The bond lengths and angles are comparable with those observed in other thiourea derivatives (Koch et al., 2001). The α-naphtalene ring system attached to N2 is essentially planar and inclined at an angle of 75.4 (1)° with respect to the plane of carbonylthiourea group. The dihedral angle between the carbonylthiourea group and furan ring is 13.1 (2)°. The molecule adopts a trans-cis configuration with respect to the position of the furoyl and naphthyl groups relative to the S atom across the thiourea C—N bonds. This geometry is stabilized by the N2—H2···.O1 intramolecular hydrogen bond (Fig.1).

In the crystal structure, molecules are linked by N1—H1···.S1 hydrogen bonds (Table 1) forming a centrosymmetric dimer (Fig. 2). The dimers are arranged along the c axis. In addition, the crystal packing is stabilized by C—H···π interactions involving the C7-C11/C16 ring.

Related literature top

For general background, see: Ashraf et al. (2007); Koch (2001). For related structures, see: Dago et al. (1987); Cao et al. (1996); Yuan et al. (1997); Kaminsky et al. (2002); Weiqun et al. (2003); Yamin & Hassan (2004). For the synthesis, see: Otazo et al. (2001). Cg1 is the centroid of the C7–C11/C16 ring.

Experimental top

The title compound was synthesized according to a previous report (Otazo et al., 2001), by converting furoyl choride into furoyl isothiocyanate and then condensing with α-naphtylamine. The resulting solid product was crystallized from ethanol yielding X-ray quality single crystals (m.p 186–187°). Elemental analysis for C₁₆H₁₂N₂O₂S calculated: C 64.86, H 4.05, N 9.46, S 10.81%; found: C 64.70, H 4.10, N 9.54, S 10.41%.

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS (Siemens, 1996); data reduction: XSCANS (Siemens, 1996); 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).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular N—H···O hydrogen bond is shown as a dashed line.
	Fig. 2. View of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

1-(2-Furoyl)-3-(1-naphthyl)thiourea top

Crystal data top

C₁₆H₁₂N₂O₂S	F(000) = 616
M_r = 296.34	D_x = 1.397 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 37 reflections
a = 9.402 (2) Å	θ = 9.9–23.4°
b = 19.082 (4) Å	µ = 0.24 mm⁻¹
c = 7.880 (2) Å	T = 294 K
β = 94.94 (1)°	Plate, white
V = 1408.5 (6) Å³	0.50 × 0.25 × 0.05 mm
Z = 4

Data collection top

Siemens P4 diffractometer	R_int = 0.043
Radiation source: fine-focus sealed tube	θ_max = 26.0°, θ_min = 2.1°
Graphite monochromator	h = −11→11
2θ/ω scans	k = −23→1
3603 measured reflections	l = −1→9
2771 independent reflections	3 standard reflections every 97 reflections
1521 reflections with I > 2σ(I)	intensity decay: 2.6%

Refinement top

Refinement on F²	All H-atom parameters refined
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0395P)² + 0.2114P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.058	(Δ/σ)_max < 0.001
wR(F²) = 0.131	Δρ_max = 0.37 e Å⁻³
S = 1.02	Δρ_min = −0.22 e Å⁻³
2771 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
239 parameters	Extinction coefficient: none
0 restraints

Crystal data top

C₁₆H₁₂N₂O₂S	V = 1408.5 (6) Å³
M_r = 296.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.402 (2) Å	µ = 0.24 mm⁻¹
b = 19.082 (4) Å	T = 294 K
c = 7.880 (2) Å	0.50 × 0.25 × 0.05 mm
β = 94.94 (1)°

Data collection top

Siemens P4 diffractometer	R_int = 0.043
3603 measured reflections	3 standard reflections every 97 reflections
2771 independent reflections	intensity decay: 2.6%
1521 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.131	All H-atom parameters refined
S = 1.02	Δρ_max = 0.37 e Å⁻³
2771 reflections	Δρ_min = −0.22 e Å⁻³
239 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.

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

	x	y	z	U_iso*/U_eq
S1	0.57874 (10)	−0.05278 (4)	0.80311 (14)	0.0521 (3)
O1	0.7296 (2)	0.17234 (11)	0.7355 (3)	0.0472 (7)
O2	0.4090 (2)	0.17986 (11)	0.9419 (3)	0.0505 (7)
N1	0.5895 (3)	0.08508 (13)	0.8319 (4)	0.0404 (8)
N2	0.7522 (3)	0.03510 (14)	0.6602 (4)	0.0382 (7)
C7	0.8101 (3)	−0.02051 (16)	0.5647 (4)	0.0334 (8)
C11	0.9652 (3)	−0.12250 (17)	0.5475 (5)	0.0378 (9)
C2	0.6455 (3)	0.02544 (15)	0.7612 (4)	0.0355 (8)
C8	0.7742 (4)	−0.0249 (2)	0.3936 (5)	0.0439 (9)
C16	0.9075 (3)	−0.06863 (15)	0.6463 (4)	0.0334 (8)
C1	0.6256 (3)	0.15409 (16)	0.8096 (4)	0.0345 (8)
C3	0.5298 (3)	0.20467 (16)	0.8776 (4)	0.0343 (8)
C10	0.9242 (4)	−0.1259 (2)	0.3713 (5)	0.0468 (10)
C15	0.9520 (4)	−0.06626 (19)	0.8244 (5)	0.0399 (9)
C6	0.3331 (4)	0.2368 (2)	0.9858 (5)	0.0538 (11)
C5	0.4016 (4)	0.2956 (2)	0.9518 (5)	0.0492 (10)
C4	0.5283 (4)	0.27538 (18)	0.8823 (5)	0.0453 (9)
C12	1.0639 (4)	−0.1706 (2)	0.6295 (6)	0.0521 (11)
C9	0.8308 (4)	−0.0782 (2)	0.2963 (6)	0.0530 (11)
C14	1.0479 (4)	−0.1136 (2)	0.8953 (6)	0.0526 (11)
C13	1.1034 (4)	−0.1664 (2)	0.7981 (6)	0.0564 (11)
H15	0.918 (3)	−0.0323 (14)	0.890 (4)	0.024 (8)*
H4	0.602 (3)	0.3026 (16)	0.844 (4)	0.040 (9)*
H10	0.963 (3)	−0.1650 (19)	0.306 (5)	0.055 (10)*
H12	1.106 (3)	−0.2074 (18)	0.560 (4)	0.055 (10)*
H6	0.242 (4)	0.228 (2)	1.031 (5)	0.072 (13)*
H8	0.709 (3)	0.0104 (16)	0.340 (4)	0.039 (9)*
H9	0.810 (3)	−0.0785 (16)	0.182 (5)	0.039 (10)*
H2	0.775 (4)	0.078 (2)	0.645 (5)	0.063 (12)*
H13	1.175 (4)	−0.197 (2)	0.860 (5)	0.081 (14)*
H14	1.073 (4)	−0.1106 (19)	1.015 (5)	0.062 (12)*
H1	0.531 (5)	0.072 (2)	0.913 (6)	0.092 (16)*
H5	0.374 (4)	0.342 (2)	0.977 (6)	0.090 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0644 (6)	0.0296 (4)	0.0675 (8)	−0.0031 (4)	0.0355 (5)	−0.0018 (5)
O1	0.0483 (14)	0.0326 (12)	0.0632 (18)	−0.0007 (10)	0.0198 (13)	0.0038 (12)
O2	0.0541 (14)	0.0330 (12)	0.067 (2)	0.0051 (11)	0.0224 (14)	0.0050 (13)
N1	0.0461 (17)	0.0264 (14)	0.051 (2)	0.0024 (13)	0.0188 (16)	0.0012 (14)
N2	0.0428 (16)	0.0303 (16)	0.0431 (19)	0.0004 (13)	0.0125 (14)	0.0014 (14)
C7	0.0360 (17)	0.0391 (18)	0.027 (2)	−0.0058 (15)	0.0110 (15)	−0.0021 (16)
C11	0.0380 (17)	0.0396 (19)	0.038 (2)	−0.0075 (15)	0.0171 (17)	−0.0070 (17)
C2	0.0413 (18)	0.0301 (17)	0.036 (2)	0.0038 (14)	0.0104 (16)	0.0026 (16)
C8	0.041 (2)	0.055 (2)	0.037 (2)	−0.0042 (18)	0.0065 (18)	0.010 (2)
C16	0.0343 (17)	0.0330 (18)	0.035 (2)	−0.0036 (14)	0.0121 (16)	−0.0021 (15)
C1	0.0386 (18)	0.0311 (17)	0.033 (2)	0.0011 (14)	0.0004 (17)	0.0025 (16)
C3	0.0398 (18)	0.0315 (17)	0.032 (2)	0.0021 (14)	0.0036 (16)	0.0020 (16)
C10	0.050 (2)	0.048 (2)	0.045 (3)	−0.0065 (19)	0.022 (2)	−0.012 (2)
C15	0.045 (2)	0.043 (2)	0.033 (2)	0.0055 (17)	0.0101 (17)	−0.0038 (18)
C6	0.057 (2)	0.052 (2)	0.055 (3)	0.017 (2)	0.021 (2)	0.003 (2)
C5	0.070 (3)	0.037 (2)	0.042 (3)	0.015 (2)	0.009 (2)	−0.0001 (19)
C4	0.054 (2)	0.036 (2)	0.047 (3)	0.0026 (17)	0.009 (2)	0.0019 (19)
C12	0.053 (2)	0.042 (2)	0.064 (3)	0.0095 (18)	0.021 (2)	−0.009 (2)
C9	0.060 (3)	0.076 (3)	0.025 (2)	−0.021 (2)	0.014 (2)	−0.012 (2)
C14	0.057 (2)	0.066 (3)	0.035 (3)	0.009 (2)	0.004 (2)	0.004 (2)
C13	0.060 (3)	0.057 (2)	0.053 (3)	0.016 (2)	0.007 (2)	0.007 (2)

Geometric parameters (Å, º) top

S1—C2	1.663 (3)	C1—C3	1.453 (4)
O1—C1	1.232 (4)	C3—C4	1.350 (4)
O2—C6	1.362 (4)	C10—C9	1.364 (6)
O2—C3	1.368 (4)	C10—H10	0.99 (4)
N1—C1	1.375 (4)	C15—C14	1.362 (5)
N1—C2	1.391 (4)	C15—H15	0.90 (3)
N1—H1	0.91 (4)	C6—C5	1.331 (5)
N2—C2	1.346 (4)	C6—H6	0.97 (4)
N2—C7	1.435 (4)	C5—C4	1.408 (5)
N2—H2	0.86 (4)	C5—H5	0.96 (4)
C7—C8	1.364 (5)	C4—H4	0.93 (3)
C7—C16	1.412 (4)	C12—C13	1.351 (6)
C11—C10	1.410 (5)	C12—H12	1.00 (3)
C11—C12	1.420 (5)	C9—H9	0.90 (3)
C11—C16	1.424 (4)	C14—C13	1.393 (6)
C8—C9	1.406 (5)	C14—H14	0.95 (4)
C8—H8	0.98 (3)	C13—H13	0.99 (4)
C16—C15	1.430 (5)

C6—O2—C3	106.8 (3)	C9—C10—C11	120.5 (4)
C1—N1—C2	128.8 (3)	C9—C10—H10	122 (2)
C1—N1—H1	122 (3)	C11—C10—H10	118 (2)
C2—N1—H1	109 (3)	C14—C15—C16	120.6 (4)
C2—N2—C7	123.0 (3)	C14—C15—H15	119.9 (18)
C2—N2—H2	115 (2)	C16—C15—H15	119.5 (18)
C7—N2—H2	121 (3)	C5—C6—O2	110.3 (3)
C8—C7—C16	120.4 (3)	C5—C6—H6	133 (2)
C8—C7—N2	119.4 (3)	O2—C6—H6	117 (2)
C16—C7—N2	120.1 (3)	C6—C5—C4	106.7 (3)
C10—C11—C12	122.0 (3)	C6—C5—H5	127 (3)
C10—C11—C16	119.2 (3)	C4—C5—H5	126 (3)
C12—C11—C16	118.8 (3)	C3—C4—C5	107.2 (3)
N2—C2—N1	116.9 (3)	C3—C4—H4	122.5 (19)
N2—C2—S1	123.6 (2)	C5—C4—H4	130.3 (19)
N1—C2—S1	119.5 (2)	C13—C12—C11	121.5 (4)
C7—C8—C9	120.7 (4)	C13—C12—H12	119.6 (19)
C7—C8—H8	118.4 (19)	C11—C12—H12	119 (2)
C9—C8—H8	120.9 (19)	C10—C9—C8	120.4 (4)
C7—C16—C11	118.9 (3)	C10—C9—H9	120 (2)
C7—C16—C15	123.4 (3)	C8—C9—H9	119 (2)
C11—C16—C15	117.8 (3)	C15—C14—C13	121.3 (4)
O1—C1—N1	123.1 (3)	C15—C14—H14	118 (2)
O1—C1—C3	122.0 (3)	C13—C14—H14	121 (2)
N1—C1—C3	114.9 (3)	C12—C13—C14	120.0 (4)
C4—C3—O2	108.9 (3)	C12—C13—H13	125 (2)
C4—C3—C1	133.0 (3)	C14—C13—H13	115 (2)
O2—C3—C1	117.9 (3)

C2—N2—C7—C8	103.8 (4)	O1—C1—C3—C4	−1.5 (6)
C2—N2—C7—C16	−78.5 (4)	N1—C1—C3—C4	179.6 (4)
C7—N2—C2—N1	−173.3 (3)	O1—C1—C3—O2	173.3 (3)
C7—N2—C2—S1	6.3 (5)	N1—C1—C3—O2	−5.6 (5)
C1—N1—C2—N2	1.9 (5)	C12—C11—C10—C9	−179.0 (3)
C1—N1—C2—S1	−177.8 (3)	C16—C11—C10—C9	0.1 (5)
C16—C7—C8—C9	1.5 (5)	C7—C16—C15—C14	−179.1 (3)
N2—C7—C8—C9	179.1 (3)	C11—C16—C15—C14	0.8 (5)
C8—C7—C16—C11	−1.2 (4)	C3—O2—C6—C5	−0.1 (4)
N2—C7—C16—C11	−178.9 (3)	O2—C6—C5—C4	0.0 (5)
C8—C7—C16—C15	178.7 (3)	O2—C3—C4—C5	−0.2 (4)
N2—C7—C16—C15	1.1 (4)	C1—C3—C4—C5	174.9 (4)
C10—C11—C16—C7	0.4 (4)	C6—C5—C4—C3	0.1 (5)
C12—C11—C16—C7	179.6 (3)	C10—C11—C12—C13	179.4 (3)
C10—C11—C16—C15	−179.5 (3)	C16—C11—C12—C13	0.3 (5)
C12—C11—C16—C15	−0.4 (4)	C11—C10—C9—C8	0.1 (5)
C2—N1—C1—O1	−9.3 (6)	C7—C8—C9—C10	−0.9 (5)
C2—N1—C1—C3	169.6 (3)	C16—C15—C14—C13	−1.2 (6)
C6—O2—C3—C4	0.2 (4)	C11—C12—C13—C14	−0.5 (6)
C6—O2—C3—C1	−175.8 (3)	C15—C14—C13—C12	1.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86 (4)	2.00 (4)	2.698 (3)	138 (3)
N1—H1···S1ⁱ	0.91 (5)	2.57 (5)	3.455 (3)	164 (4)
C5—H5···Cg1ⁱⁱ	0.96 (4)	2.85 (4)	3.654 (4)	143 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₂O₂S
M_r	296.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	9.402 (2), 19.082 (4), 7.880 (2)
β (°)	94.94 (1)
V (Å³)	1408.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.50 × 0.25 × 0.05

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3603, 2771, 1521
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.131, 1.02
No. of reflections	2771
No. of parameters	239
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.22

Computer programs: XSCANS (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86 (4)	2.00 (4)	2.698 (3)	138 (3)
N1—H1···S1ⁱ	0.91 (5)	2.57 (5)	3.455 (3)	164 (4)
C5—H5···Cg1ⁱⁱ	0.96 (4)	2.85 (4)	3.654 (4)	143 (3)

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

Acknowledgements

The authors thank the Crystallography Group, São Carlos Physics Institute, USP, Brazil, for allowing the X-ray data collection. The authors acknowledge financial support from the Brazilian agency CNPq.

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