1-Benzoyl-3-(naphthalen-1-yl)thio­urea

Saeed, S.; Rashid, N.; Jasinski, J.P.; Golen, J.A.

doi:10.1107/S160053681104582X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3187

https://doi.org/10.1107/S160053681104582X

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1-Benzoyl-3-(naphthalen-1-yl)thiourea

Sohail Saeed,^a ^* Naghmana Rashid,^a Jerry P Jasinski ^b and James A Golen ^b

^aDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad 44000, Pakistan, and ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
^*Correspondence e-mail: sohail262001@yahoo.com

(Received 25 October 2011; accepted 31 October 2011; online 5 November 2011)

In the title compound, C₁₈H₁₄N₂OS, the dihedral angle between the mean planes of the 3-naphthyl and 1-benzoyl rings is 20.7 (1)°. The crystal packing is stabilized by weak N—H⋯S interactions. Intramolecular N—H⋯O and C—H⋯O hydrogen bonding is also observed.

Related literature

For the biological activity of thiourea in medicinal chemistry, see: Saeed et al. (2009 , 2010a ,b ); Maddani & Prabhu (2010 ). For the use of thiourea derivatives in organocatalysis, see: Jung & Kim (2008 ) and for their use as curing agents for epoxy resins, see: Saeed et al. (2011 ). For the use of thioureas as ligands in coordination chemistry, see: Burrows et al. (1999 ); Henderson et al. (2002 ); Schuster et al. (1990 ). For the pesticidal activity of acyl thioureas, see: Che et al. (1999 ). For standard bond lengths, see Allen et al. (1987 ).

Experimental

Crystal data

C₁₈H₁₄N₂OS
M_r = 306.37
Monoclinic, P 2₁ /n
a = 9.7368 (14) Å
b = 5.2256 (10) Å
c = 28.619 (4) Å
β = 92.126 (12)°
V = 1455.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 K
0.35 × 0.08 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.925, T_max = 0.982
12731 measured reflections
3460 independent reflections
2206 reflections with I > 2σ(I)
R_int = 0.082

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.135
S = 1.05
3460 reflections
205 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.36 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 (2)	1.85 (2)	2.600 (3)	144 (2)
N1—H1⋯S1ⁱ	0.86 (2)	2.80 (2)	3.591 (2)	153 (2)
C15—H15A⋯O1	0.95	2.51	3.411 (3)	159
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681104582X/fk2043sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681104582X/fk2043Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681104582X/fk2043Isup3.cml

checkCIF report

Comment top

Thioureas are the subject of significant interest because of their usefulness in medicinal chemistry due to their biological activity as fungicides (Saeed et al., 2010a), anticancer (Saeed et al., 2010b),herbicides, rodenticides and phenoloxidase enzymatic inhibitors (Maddani & Prabhu, 2010). Recently, thiourea derivatives have found use in organocatalysis (Jung & Kim, 2008). Amino-thiourea derivatives (Saeed et al., 2009) and their transition metal complexes are used as curing agents for epoxy resins (Saeed et al., 2011). Thioureas have a long history as a ligand in coordination chemistry and coordinate readily to a metal via sulfur and oxygen (Burrows et al., 1999). These hard and soft donor atoms provide a multitude of bonding possibilities (Henderson et al., 2002). Hydrogen bonding behavior of some thioureas have been investigated and it is found that intramolecular hydrogen bonds between the carbonyl oxygen and a nitrogen atom is common. The complexing capacity of thiourea derivatives has been reported (Schuster et al., 1990). Also, some acyl thioureas have been found to possess pesticidal activities and promote plant growth while others have been shown to have a notable positive effect on the germination of maize seeds and on the chlorophyll contents in seedling leaves (Che et al., 1999). With the simultaneous presence of S, N and O electron donors, the versalitility and behavior of acylthioureas as building blocks in polydentate ligands for metal ions have become a recent topic of interest. Substituted acylthiourea ligands might act as monodentate sulfur donors, bidentate oxygen and nitrogen donors. In continuation of our research program concerned with structural modification of biologically active thiourea derivatives and their transition metal complexes, we aim to incorporate the aliphatic and aromatic moieties in the substituted phenyl nucleus with thiourea functionality to obtain new functions in an attempt to improve the antimicrobial profile of these compounds. In view of the importance of thiourea derivatives, the crystal structure of the title compound, C₁₈H₁₄N₂O_S, (I), is reported.

In the title compound, (I), the dihedral angle between the mean planes of the 3-naphthyl and 1-benzoyl rings is 20.7 (1)° (Fig. 1). Crystal packing is stabilized by weak N1—H1···S1 intermolecular interactions (Table 1, Fig. 2). N2—H2···O1 intramolecular hydrogen bonds are also observed (Table 1).

Related literature top

For the biological activity of thiourea in medicinal chemistry, see: Saeed et al. (2009, 2010a,b); Maddani & Prabhu (2010). For the use of thiourea derivatives in organocatalysis, see: Jung & Kim (2008) and for their use as curing agents for epoxy resins, see: Saeed et al. (2011). For the use of thioureas as a ligand in coordination chemistry, see: Burrows et al. (1999); Henderson et al. (2002); Schuster et al. (1990). For the pesticidal activity of acyl thioureas, see: Che et al. (1999). For standard bond lengths, see Allen et al. (1987).

Experimental top

A solution of benzoyl chloride (0.01 mol) in anhydrous acetone (80 ml) and 3% tetrabutylammonium bromide (TBAB) as a phase-transfer catalyst (PTC) in anhydrous acetone was added dropwise to a suspension of dry ammonium thiocyanate (0.01 mol) in acetone (50 ml) and the reaction mixture was refluxed for 45 min. After cooling to room temperature, a solution of 1-naphthylamine (0.01 mol) in anhydrous acetone (25 ml) was added dropwise and the resulting mixture refluxed for 2.5 h. Hydrochloric acid (0.1 N, 300 ml) was added, and the solution was filtered. The solid product was washed with water and purified by re-crystallization from ethanol.

Structure description top

For the biological activity of thiourea in medicinal chemistry, see: Saeed et al. (2009, 2010a,b); Maddani & Prabhu (2010). For the use of thiourea derivatives in organocatalysis, see: Jung & Kim (2008) and for their use as curing agents for epoxy resins, see: Saeed et al. (2011). For the use of thioureas as a ligand in coordination chemistry, see: Burrows et al. (1999); Henderson et al. (2002); Schuster et al. (1990). For the pesticidal activity of acyl thioureas, see: Che et al. (1999). For standard bond lengths, see Allen et al. (1987).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed along the b axis. Dashed lines indicate weak N1—H1···S1 intermolecular interactions.

1-Benzoyl-3-(naphthalen-1-yl)thiourea top

Crystal data top

C₁₈H₁₄N₂OS	F(000) = 640
M_r = 306.37	D_x = 1.398 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1307 reflections
a = 9.7368 (14) Å	θ = 3.5–32.3°
b = 5.2256 (10) Å	µ = 0.23 mm⁻¹
c = 28.619 (4) Å	T = 173 K
β = 92.126 (12)°	Rod, colourless
V = 1455.2 (4) Å³	0.35 × 0.08 × 0.08 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3460 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2206 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.082
Detector resolution: 16.1500 pixels mm^-1	θ_max = 27.9°, θ_min = 4.0°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −6→6
T_min = 0.925, T_max = 0.982	l = −34→37
12731 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0427P)² + 0.1745P] where P = (F_o² + 2F_c²)/3
3460 reflections	(Δ/σ)_max = 0.001
205 parameters	Δρ_max = 0.25 e Å⁻³
2 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₈H₁₄N₂OS	V = 1455.2 (4) Å³
M_r = 306.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.7368 (14) Å	µ = 0.23 mm⁻¹
b = 5.2256 (10) Å	T = 173 K
c = 28.619 (4) Å	0.35 × 0.08 × 0.08 mm
β = 92.126 (12)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3460 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	2206 reflections with I > 2σ(I)
T_min = 0.925, T_max = 0.982	R_int = 0.082
12731 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	2 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.25 e Å⁻³
3460 reflections	Δρ_min = −0.36 e Å⁻³
205 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..

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

	x	y	z	U_iso*/U_eq
S1	0.63172 (7)	0.32704 (17)	0.54848 (3)	0.0446 (2)
O1	0.28206 (18)	0.5576 (4)	0.63936 (6)	0.0395 (5)
N1	0.4117 (2)	0.5657 (4)	0.57512 (7)	0.0300 (5)
H1	0.423 (3)	0.632 (5)	0.5480 (7)	0.036*
N2	0.4889 (2)	0.2542 (4)	0.62654 (7)	0.0280 (5)
H2	0.421 (2)	0.315 (5)	0.6413 (9)	0.034*
C1	0.2515 (3)	1.0084 (5)	0.54374 (9)	0.0313 (6)
H1A	0.3367	0.9825	0.5293	0.038*
C2	0.1632 (3)	1.1966 (5)	0.52738 (10)	0.0413 (7)
H2A	0.1872	1.2993	0.5016	0.050*
C3	0.0399 (3)	1.2359 (6)	0.54847 (11)	0.0427 (7)
H3A	−0.0216	1.3642	0.5369	0.051*
C4	0.0059 (3)	1.0899 (6)	0.58617 (10)	0.0407 (7)
H4A	−0.0784	1.1195	0.6010	0.049*
C5	0.0929 (3)	0.9015 (5)	0.60260 (10)	0.0364 (7)
H5A	0.0685	0.8010	0.6287	0.044*
C6	0.2167 (2)	0.8566 (5)	0.58122 (8)	0.0257 (5)
C7	0.3049 (2)	0.6496 (5)	0.60124 (8)	0.0272 (6)
C8	0.5082 (2)	0.3745 (5)	0.58638 (9)	0.0292 (6)
C9	0.5611 (2)	0.0543 (5)	0.64982 (9)	0.0268 (6)
C10	0.6612 (2)	−0.0889 (5)	0.62991 (9)	0.0331 (6)
H10A	0.6876	−0.0526	0.5990	0.040*
C11	0.7248 (3)	−0.2889 (6)	0.65515 (10)	0.0395 (7)
H11A	0.7964	−0.3833	0.6415	0.047*
C12	0.6859 (3)	−0.3498 (5)	0.69861 (10)	0.0379 (7)
H12A	0.7289	−0.4890	0.7147	0.046*
C13	0.5827 (2)	−0.2094 (5)	0.72029 (9)	0.0297 (6)
C14	0.5195 (2)	−0.0002 (5)	0.69628 (8)	0.0261 (5)
C15	0.4192 (2)	0.1399 (5)	0.71991 (9)	0.0306 (6)
H15A	0.3758	0.2818	0.7048	0.037*
C16	0.3832 (3)	0.0759 (5)	0.76395 (9)	0.0354 (7)
H16A	0.3159	0.1740	0.7791	0.043*
C17	0.4444 (3)	−0.1323 (5)	0.78703 (9)	0.0371 (7)
H17A	0.4181	−0.1770	0.8176	0.045*
C18	0.5413 (3)	−0.2703 (5)	0.76558 (9)	0.0339 (6)
H18A	0.5826	−0.4119	0.7815	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0376 (4)	0.0694 (6)	0.0275 (4)	0.0166 (4)	0.0126 (3)	0.0087 (4)
O1	0.0407 (11)	0.0504 (12)	0.0283 (11)	0.0153 (10)	0.0124 (8)	0.0099 (9)
N1	0.0283 (11)	0.0381 (13)	0.0239 (12)	0.0030 (10)	0.0044 (9)	0.0055 (10)
N2	0.0248 (11)	0.0373 (13)	0.0223 (11)	0.0044 (10)	0.0066 (9)	0.0002 (9)
C1	0.0320 (14)	0.0316 (15)	0.0304 (15)	−0.0021 (12)	0.0043 (11)	−0.0020 (12)
C2	0.0535 (18)	0.0349 (16)	0.0356 (16)	0.0020 (14)	0.0032 (14)	0.0069 (13)
C3	0.0403 (16)	0.0390 (17)	0.0485 (19)	0.0075 (14)	−0.0042 (14)	0.0044 (14)
C4	0.0312 (15)	0.0450 (18)	0.0460 (18)	0.0060 (14)	0.0049 (13)	0.0053 (14)
C5	0.0315 (14)	0.0396 (17)	0.0384 (16)	0.0038 (13)	0.0063 (12)	0.0069 (13)
C6	0.0249 (13)	0.0277 (14)	0.0245 (13)	−0.0005 (11)	0.0015 (10)	−0.0014 (11)
C7	0.0261 (13)	0.0317 (14)	0.0241 (13)	−0.0010 (11)	0.0055 (10)	−0.0017 (11)
C8	0.0233 (13)	0.0381 (16)	0.0260 (14)	0.0033 (12)	0.0009 (10)	−0.0009 (12)
C9	0.0237 (12)	0.0276 (14)	0.0289 (14)	−0.0001 (11)	0.0003 (10)	−0.0024 (11)
C10	0.0285 (14)	0.0390 (16)	0.0319 (15)	0.0033 (12)	0.0017 (11)	−0.0021 (12)
C11	0.0312 (15)	0.0408 (17)	0.0463 (18)	0.0070 (13)	−0.0002 (13)	−0.0087 (14)
C12	0.0376 (15)	0.0348 (16)	0.0409 (17)	0.0019 (13)	−0.0050 (13)	0.0004 (13)
C13	0.0276 (13)	0.0270 (14)	0.0340 (15)	−0.0040 (11)	−0.0040 (11)	−0.0003 (11)
C14	0.0258 (13)	0.0260 (13)	0.0263 (14)	−0.0058 (11)	−0.0010 (10)	−0.0011 (10)
C15	0.0305 (14)	0.0312 (14)	0.0301 (14)	0.0025 (12)	0.0022 (11)	0.0024 (11)
C16	0.0394 (15)	0.0372 (16)	0.0302 (15)	0.0005 (13)	0.0074 (12)	0.0024 (12)
C17	0.0410 (16)	0.0426 (17)	0.0279 (15)	−0.0078 (14)	0.0029 (12)	0.0076 (13)
C18	0.0381 (15)	0.0286 (14)	0.0342 (15)	−0.0080 (13)	−0.0083 (12)	0.0053 (12)

Geometric parameters (Å, º) top

S1—C8	1.667 (2)	C6—C7	1.483 (3)
O1—C7	1.220 (3)	C9—C10	1.370 (3)
N1—C7	1.375 (3)	C9—C14	1.433 (3)
N1—C8	1.401 (3)	C10—C11	1.401 (4)
N1—H1	0.859 (16)	C10—H10A	0.9500
N2—C8	1.329 (3)	C11—C12	1.351 (4)
N2—C9	1.412 (3)	C11—H11A	0.9500
N2—H2	0.861 (16)	C12—C13	1.407 (4)
C1—C2	1.377 (4)	C12—H12A	0.9500
C1—C6	1.386 (3)	C13—C18	1.408 (4)
C1—H1A	0.9500	C13—C14	1.419 (3)
C2—C3	1.379 (4)	C14—C15	1.413 (3)
C2—H2A	0.9500	C15—C16	1.362 (3)
C3—C4	1.372 (4)	C15—H15A	0.9500
C3—H3A	0.9500	C16—C17	1.395 (4)
C4—C5	1.370 (4)	C16—H16A	0.9500
C4—H4A	0.9500	C17—C18	1.353 (4)
C5—C6	1.392 (3)	C17—H17A	0.9500
C5—H5A	0.9500	C18—H18A	0.9500

C7—N1—C8	128.1 (2)	C10—C9—N2	123.9 (2)
C7—N1—H1	119.1 (18)	C10—C9—C14	120.5 (2)
C8—N1—H1	112.8 (18)	N2—C9—C14	115.6 (2)
C8—N2—C9	132.4 (2)	C9—C10—C11	120.0 (3)
C8—N2—H2	112.6 (18)	C9—C10—H10A	120.0
C9—N2—H2	115.0 (18)	C11—C10—H10A	120.0
C2—C1—C6	120.3 (2)	C12—C11—C10	121.1 (3)
C2—C1—H1A	119.9	C12—C11—H11A	119.5
C6—C1—H1A	119.9	C10—C11—H11A	119.5
C1—C2—C3	120.1 (3)	C11—C12—C13	120.8 (3)
C1—C2—H2A	120.0	C11—C12—H12A	119.6
C3—C2—H2A	120.0	C13—C12—H12A	119.6
C4—C3—C2	120.0 (3)	C12—C13—C18	121.4 (2)
C4—C3—H3A	120.0	C12—C13—C14	119.5 (2)
C2—C3—H3A	120.0	C18—C13—C14	119.1 (2)
C5—C4—C3	120.4 (3)	C15—C14—C13	117.5 (2)
C5—C4—H4A	119.8	C15—C14—C9	124.4 (2)
C3—C4—H4A	119.8	C13—C14—C9	118.1 (2)
C4—C5—C6	120.3 (3)	C16—C15—C14	121.4 (2)
C4—C5—H5A	119.9	C16—C15—H15A	119.3
C6—C5—H5A	119.9	C14—C15—H15A	119.3
C1—C6—C5	119.0 (2)	C15—C16—C17	120.7 (3)
C1—C6—C7	124.2 (2)	C15—C16—H16A	119.7
C5—C6—C7	116.8 (2)	C17—C16—H16A	119.7
O1—C7—N1	121.8 (2)	C18—C17—C16	119.6 (3)
O1—C7—C6	120.7 (2)	C18—C17—H17A	120.2
N1—C7—C6	117.5 (2)	C16—C17—H17A	120.2
N2—C8—N1	114.9 (2)	C17—C18—C13	121.7 (3)
N2—C8—S1	128.4 (2)	C17—C18—H18A	119.2
N1—C8—S1	116.76 (19)	C13—C18—H18A	119.2

C6—C1—C2—C3	0.4 (4)	C14—C9—C10—C11	−0.6 (4)
C1—C2—C3—C4	0.9 (5)	C9—C10—C11—C12	2.2 (4)
C2—C3—C4—C5	−1.1 (5)	C10—C11—C12—C13	−1.7 (4)
C3—C4—C5—C6	0.1 (4)	C11—C12—C13—C18	−179.9 (2)
C2—C1—C6—C5	−1.5 (4)	C11—C12—C13—C14	−0.5 (4)
C2—C1—C6—C7	180.0 (2)	C12—C13—C14—C15	−178.2 (2)
C4—C5—C6—C1	1.2 (4)	C18—C13—C14—C15	1.2 (3)
C4—C5—C6—C7	179.9 (2)	C12—C13—C14—C9	2.0 (3)
C8—N1—C7—O1	−0.4 (4)	C18—C13—C14—C9	−178.6 (2)
C8—N1—C7—C6	180.0 (2)	C10—C9—C14—C15	178.8 (2)
C1—C6—C7—O1	165.4 (3)	N2—C9—C14—C15	−3.5 (4)
C5—C6—C7—O1	−13.2 (4)	C10—C9—C14—C13	−1.5 (3)
C1—C6—C7—N1	−15.0 (4)	N2—C9—C14—C13	176.2 (2)
C5—C6—C7—N1	166.4 (2)	C13—C14—C15—C16	−0.5 (4)
C9—N2—C8—N1	179.7 (2)	C9—C14—C15—C16	179.2 (2)
C9—N2—C8—S1	−0.6 (4)	C14—C15—C16—C17	−0.4 (4)
C7—N1—C8—N2	3.1 (4)	C15—C16—C17—C18	0.7 (4)
C7—N1—C8—S1	−176.7 (2)	C16—C17—C18—C13	0.0 (4)
C8—N2—C9—C10	−10.9 (4)	C12—C13—C18—C17	178.4 (3)
C8—N2—C9—C14	171.5 (3)	C14—C13—C18—C17	−0.9 (4)
N2—C9—C10—C11	−178.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86 (2)	1.85 (2)	2.600 (3)	144 (2)
N1—H1···S1ⁱ	0.86 (2)	2.80 (2)	3.591 (2)	153 (2)
C15—H15A···O1	0.95	2.51	3.411 (3)	159

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄N₂OS
M_r	306.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	9.7368 (14), 5.2256 (10), 28.619 (4)
β (°)	92.126 (12)
V (Å³)	1455.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.35 × 0.08 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.925, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	12731, 3460, 2206
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.135, 1.05
No. of reflections	3460
No. of parameters	205
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.36

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.861 (16)	1.85 (2)	2.600 (3)	144 (2)
N1—H1···S1ⁱ	0.859 (16)	2.80 (2)	3.591 (2)	153 (2)
C15—H15A···O1	0.95	2.51	3.411 (3)	158.9

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

JPJ acknowledges the NSF–MRI program (grant No·CHE1039027) for funds to purchase the X-ray diffractometer.

References

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