(E)-[2-(1,3-Dithio­lan-2-yl­idene)hydrazinyl­idene](3-fluoro­phen­yl)methyl 3-fluoro­benzoate

Yin, L.

doi:10.1107/S1600536813007319

organic compounds

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Volume 69| Part 4| April 2013| Page o571

doi:10.1107/S1600536813007319

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(E)-[2-(1,3-Dithiolan-2-ylidene)hydrazinylidene](3-fluorophenyl)methyl 3-fluorobenzoate

Ling Yin ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Jining University, Qufu 273155, People's Republic of China
^*Correspondence e-mail: yinling_1109@163.com

(Received 13 March 2013; accepted 17 March 2013; online 23 March 2013)

In the title compound, C₁₇H₁₂F₂N₂O₂S₂, the conformation of the dithiacyclopentane ring is a half-chair, with a total puckering amplitude Q_T = 0.460 (1) Å. π–π interactions [centroid–centroid distance = 3.585 (9) Å between the fluorophenyl rings of neighbouring molecules] and C—H⋯N and C—H⋯O interactions help to stabilize the crystal structure and form ladders along the c axis.

Related literature

For the use of dithiolan heterocyclic compounds as broad-spectrum fungicides, see: Tanaka et al. (1976 ); Wang et al. (1994 ).

Experimental

Crystal data

C₁₇H₁₂F₂N₂O₂S₂
M_r = 378.41
Triclinic, $[P \overline 1]$
a = 9.124 (4) Å
b = 9.757 (4) Å
c = 10.738 (4) Å
α = 104.592 (3)°
β = 110.326 (5)°
γ = 101.194 (4)°
V = 824.6 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 113 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009) T_min = 0.932, T_max = 0.932
7057 measured reflections
2896 independent reflections
2098 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.076
S = 0.96
2896 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O2ⁱ	0.97	2.49	3.280 (2)	138
C10—H10B⋯O2ⁱⁱ	0.97	2.46	3.248 (2)	138
C13—H13A⋯N1ⁱⁱⁱ	0.93	2.50	3.424 (3)	176
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x+1, y, z; (iii) -x, -y+2, -z+2.

Data collection: CrystalClear-SM Expert (Rigaku/MSC, 2009); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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 I, global. DOI: 10.1107/S1600536813007319/hg5300sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813007319/hg5300Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813007319/hg5300Isup3.cml

checkCIF report

Comment top

Many dithiolan heterocyclic compounds have been widely used as potent and broad-spectrum fungicides (Tanaka et al., 1976; Wang et al., 1994). In order to search for new heterocylic compounds with higher biological activities, we synthesized the (E)-((1,3-dithiolan-2-yl)diazenyl)(3-fluorophenyl)methyl 3-fluorobenzoate and describe its structure here.

In the title compound, C₁₇H₁₂F₂N₂O₂S₂, the conformation of the dithiacyclopentane ring (C8—C10/S1—S2) is halfchair, with a total puckering amplitude Q_T = 0.460 (1) Å. π-π interactions (centroid-to-centroid distances 3.585 (9) Å between the fluorophenyl rings (C12—C17) of neighbouring molecules) and intermolecular C—H···N and C—H···O interactions help to stabilize the crystal structure (Table 1).

Related literature top

For the use of dithiolan heterocyclic compounds as broad-spectrum fungicides, see: Tanaka et al. (1976); Wang et al. (1994).

Experimental top

1.34 g (10 mmol) of (1,3-dithiolan-2-ylidene)hydrazine and 20 mmol triethylamine was dissolved in 15 ml of dichloromethane and stirred at room temperature, 3.17 g (20 mmol) 3-fluorobenzoyl chloride was added dropwise to the mixture. The reaction mixture was stirred vigorously at 273 K for 3 h. The reaction mixture was poured into 200 ml of water and extracted with three 50-ml portions of dichloromethane. The combined extracts were washed with saturated brine, dried over anhydrous sodium sulfate and evaporated on a rotary evaporator to afford the crude product, which was purified by column chromatography to yield the pure product as colorless crystals. Single crystals suitable for X-ray diffraction were obtained through slow evaporation of a solution of the pure title compound in ethanol.

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku/MSC, 2009); cell refinement: CrystalClear-SM Expert (Rigaku/MSC, 2009); data reduction: CrystalClear-SM Expert (Rigaku/MSC, 2009); 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. View of the title compound showing the atomic numbering and 40% probability displacement ellipsoids.

(E)-[2-(1,3-Dithiolan-2-ylidene)hydrazinylidene](3-fluorophenyl)methyl 3-fluorobenzoate top

Crystal data top

C₁₇H₁₂F₂N₂O₂S₂	Z = 2
M_r = 378.41	F(000) = 388
Triclinic, P1	D_x = 1.524 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.124 (4) Å	Cell parameters from 2617 reflections
b = 9.757 (4) Å	θ = 2.2–27.9°
c = 10.738 (4) Å	µ = 0.36 mm⁻¹
α = 104.592 (3)°	T = 113 K
β = 110.326 (5)°	Block, colorless
γ = 101.194 (4)°	0.20 × 0.20 × 0.20 mm
V = 824.6 (6) Å³

Data collection top

Rigaku Saturn724 CCD diffractometer	2896 independent reflections
Radiation source: rotating anode	2098 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.036
Detector resolution: 14.22 pixels mm^-1	θ_max = 25.0°, θ_min = 2.2°
ω and ϕ scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009)	k = −11→11
T_min = 0.932, T_max = 0.932	l = −12→12
7057 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: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0322P)²] where P = (F_o² + 2F_c²)/3
2896 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₇H₁₂F₂N₂O₂S₂	γ = 101.194 (4)°
M_r = 378.41	V = 824.6 (6) Å³
Triclinic, P1	Z = 2
a = 9.124 (4) Å	Mo Kα radiation
b = 9.757 (4) Å	µ = 0.36 mm⁻¹
c = 10.738 (4) Å	T = 113 K
α = 104.592 (3)°	0.20 × 0.20 × 0.20 mm
β = 110.326 (5)°

Data collection top

Rigaku Saturn724 CCD diffractometer	2896 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009)	2098 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.932	R_int = 0.036
7057 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 0.96	Δρ_max = 0.39 e Å⁻³
2896 reflections	Δρ_min = −0.20 e Å⁻³
226 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	0.10124 (6)	0.83442 (5)	0.59445 (5)	0.02517 (15)
O1	−0.12238 (14)	1.08666 (13)	0.92674 (12)	0.0209 (3)
N1	−0.06721 (17)	0.92577 (15)	0.75780 (14)	0.0183 (4)
F1	−0.49133 (14)	0.43408 (13)	0.61224 (12)	0.0447 (4)
C1	−0.3309 (2)	0.6858 (2)	0.71390 (18)	0.0234 (5)
H1B	−0.2714	0.6668	0.6602	0.028*
S2	0.31536 (6)	1.14801 (5)	0.73274 (5)	0.02773 (15)
F2	0.06577 (13)	1.50851 (11)	1.36811 (11)	0.0320 (3)
O2	−0.27848 (15)	1.15266 (14)	0.75200 (12)	0.0241 (3)
N2	0.05995 (17)	1.05067 (16)	0.78311 (15)	0.0205 (4)
C2	−0.4583 (2)	0.5746 (2)	0.7016 (2)	0.0300 (5)
C3	−0.5519 (2)	0.5965 (2)	0.7762 (2)	0.0378 (6)
H3A	−0.6389	0.5187	0.7637	0.045*
C4	−0.5130 (2)	0.7376 (3)	0.8706 (2)	0.0375 (6)
H4A	−0.5742	0.7552	0.9231	0.045*
C5	−0.3846 (2)	0.8530 (2)	0.88806 (19)	0.0277 (5)
H5A	−0.3591	0.9474	0.9524	0.033*
C6	−0.2929 (2)	0.8280 (2)	0.80908 (18)	0.0194 (4)
C7	−0.1555 (2)	0.94860 (19)	0.82551 (17)	0.0177 (4)
C8	0.1433 (2)	1.01277 (19)	0.71174 (18)	0.0196 (4)
C9	0.2838 (2)	0.8807 (2)	0.56131 (19)	0.0281 (5)
H9A	0.3748	0.8649	0.6302	0.034*
H9B	0.2634	0.8176	0.4675	0.034*
C10	0.3251 (2)	1.0425 (2)	0.57270 (19)	0.0273 (5)
H10A	0.2471	1.0544	0.4909	0.033*
H10B	0.4345	1.0771	0.5771	0.033*
C11	−0.1953 (2)	1.18274 (19)	0.87559 (19)	0.0183 (4)
C12	−0.1586 (2)	1.32341 (19)	0.99052 (18)	0.0176 (4)
C13	−0.0640 (2)	1.3463 (2)	1.13176 (18)	0.0193 (4)
H13A	−0.0256	1.2719	1.1584	0.023*
C14	−0.0294 (2)	1.4828 (2)	1.23034 (18)	0.0214 (4)
C15	−0.0852 (2)	1.5955 (2)	1.19552 (19)	0.0219 (4)
H15A	−0.0584	1.6869	1.2650	0.026*
C16	−0.1816 (2)	1.5698 (2)	1.05533 (19)	0.0235 (5)
H16A	−0.2215	1.6441	1.0299	0.028*
C17	−0.2192 (2)	1.4342 (2)	0.95261 (19)	0.0211 (4)
H17A	−0.2847	1.4171	0.8584	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0288 (3)	0.0228 (3)	0.0234 (3)	0.0054 (2)	0.0145 (2)	0.0038 (2)
O1	0.0265 (7)	0.0204 (7)	0.0161 (7)	0.0112 (6)	0.0082 (6)	0.0048 (6)
N1	0.0181 (8)	0.0184 (8)	0.0171 (8)	0.0044 (7)	0.0065 (7)	0.0062 (7)
F1	0.0460 (8)	0.0304 (7)	0.0372 (7)	−0.0090 (6)	0.0073 (6)	0.0089 (6)
C1	0.0196 (10)	0.0296 (11)	0.0191 (10)	0.0050 (9)	0.0059 (9)	0.0106 (9)
S2	0.0240 (3)	0.0262 (3)	0.0290 (3)	0.0009 (2)	0.0132 (2)	0.0055 (2)
F2	0.0423 (7)	0.0278 (6)	0.0184 (6)	0.0112 (5)	0.0067 (5)	0.0041 (5)
O2	0.0255 (7)	0.0278 (7)	0.0168 (7)	0.0102 (6)	0.0054 (6)	0.0076 (6)
N2	0.0213 (9)	0.0163 (8)	0.0221 (8)	0.0036 (7)	0.0093 (7)	0.0052 (7)
C2	0.0285 (12)	0.0274 (11)	0.0230 (11)	0.0003 (9)	0.0028 (10)	0.0088 (10)
C3	0.0219 (12)	0.0488 (15)	0.0404 (13)	−0.0011 (11)	0.0090 (11)	0.0265 (12)
C4	0.0287 (12)	0.0591 (16)	0.0381 (13)	0.0155 (11)	0.0211 (11)	0.0265 (12)
C5	0.0259 (11)	0.0374 (12)	0.0253 (11)	0.0146 (10)	0.0111 (10)	0.0156 (10)
C6	0.0178 (10)	0.0271 (11)	0.0146 (10)	0.0087 (8)	0.0051 (8)	0.0101 (9)
C7	0.0204 (10)	0.0196 (10)	0.0119 (9)	0.0090 (8)	0.0040 (8)	0.0056 (8)
C8	0.0211 (10)	0.0195 (10)	0.0166 (10)	0.0067 (8)	0.0050 (9)	0.0074 (8)
C9	0.0277 (12)	0.0366 (12)	0.0230 (11)	0.0118 (10)	0.0136 (10)	0.0092 (10)
C10	0.0207 (10)	0.0397 (12)	0.0225 (11)	0.0069 (9)	0.0100 (9)	0.0130 (10)
C11	0.0157 (10)	0.0218 (10)	0.0224 (11)	0.0063 (8)	0.0110 (9)	0.0111 (9)
C12	0.0149 (10)	0.0203 (10)	0.0200 (10)	0.0037 (8)	0.0102 (8)	0.0080 (8)
C13	0.0195 (10)	0.0205 (10)	0.0227 (10)	0.0079 (8)	0.0110 (9)	0.0106 (9)
C14	0.0228 (11)	0.0244 (11)	0.0169 (10)	0.0065 (9)	0.0090 (9)	0.0065 (9)
C15	0.0238 (11)	0.0172 (10)	0.0254 (11)	0.0050 (8)	0.0141 (9)	0.0041 (9)
C16	0.0245 (11)	0.0217 (10)	0.0301 (11)	0.0103 (9)	0.0150 (10)	0.0110 (9)
C17	0.0204 (10)	0.0242 (10)	0.0222 (10)	0.0073 (8)	0.0102 (9)	0.0114 (9)

Geometric parameters (Å, º) top

S1—C8	1.7499 (19)	C5—C6	1.395 (2)
S1—C9	1.8178 (18)	C5—H5A	0.9300
O1—C11	1.368 (2)	C6—C7	1.469 (2)
O1—C7	1.401 (2)	C9—C10	1.513 (3)
N1—C7	1.274 (2)	C9—H9A	0.9700
N1—N2	1.4036 (19)	C9—H9B	0.9700
F1—C2	1.366 (2)	C10—H10A	0.9700
C1—C2	1.370 (2)	C10—H10B	0.9700
C1—C6	1.394 (2)	C11—C12	1.483 (2)
C1—H1B	0.9300	C12—C17	1.392 (3)
S2—C8	1.7480 (18)	C12—C13	1.393 (2)
S2—C10	1.8088 (19)	C13—C14	1.374 (2)
F2—C14	1.357 (2)	C13—H13A	0.9300
O2—C11	1.200 (2)	C14—C15	1.378 (3)
N2—C8	1.294 (2)	C15—C16	1.381 (2)
C2—C3	1.370 (3)	C15—H15A	0.9300
C3—C4	1.381 (3)	C16—C17	1.382 (2)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.380 (3)	C17—H17A	0.9300
C4—H4A	0.9300

C8—S1—C9	95.19 (8)	S1—C9—H9A	110.1
C11—O1—C7	115.41 (14)	C10—C9—H9B	110.1
C7—N1—N2	115.89 (14)	S1—C9—H9B	110.1
C2—C1—C6	118.25 (17)	H9A—C9—H9B	108.4
C2—C1—H1B	120.9	C9—C10—S2	107.36 (12)
C6—C1—H1B	120.9	C9—C10—H10A	110.2
C8—S2—C10	94.44 (8)	S2—C10—H10A	110.2
C8—N2—N1	110.12 (14)	C9—C10—H10B	110.2
F1—C2—C1	118.15 (17)	S2—C10—H10B	110.2
F1—C2—C3	118.45 (17)	H10A—C10—H10B	108.5
C1—C2—C3	123.39 (19)	O2—C11—O1	122.43 (17)
C2—C3—C4	117.95 (18)	O2—C11—C12	125.87 (18)
C2—C3—H3A	121.0	O1—C11—C12	111.70 (15)
C4—C3—H3A	121.0	C17—C12—C13	120.61 (17)
C5—C4—C3	120.84 (18)	C17—C12—C11	117.79 (17)
C5—C4—H4A	119.6	C13—C12—C11	121.59 (18)
C3—C4—H4A	119.6	C14—C13—C12	117.59 (18)
C4—C5—C6	119.96 (18)	C14—C13—H13A	121.2
C4—C5—H5A	120.0	C12—C13—H13A	121.2
C6—C5—H5A	120.0	F2—C14—C13	118.49 (18)
C1—C6—C5	119.59 (17)	F2—C14—C15	118.47 (16)
C1—C6—C7	119.26 (15)	C13—C14—C15	123.03 (18)
C5—C6—C7	121.15 (16)	C14—C15—C16	118.59 (17)
N1—C7—O1	122.72 (15)	C14—C15—H15A	120.7
N1—C7—C6	121.68 (16)	C16—C15—H15A	120.7
O1—C7—C6	115.47 (14)	C15—C16—C17	120.32 (19)
N2—C8—S2	118.67 (14)	C15—C16—H16A	119.8
N2—C8—S1	125.76 (13)	C17—C16—H16A	119.8
S2—C8—S1	115.57 (10)	C16—C17—C12	119.84 (18)
C10—C9—S1	108.17 (13)	C16—C17—H17A	120.1
C10—C9—H9A	110.1	C12—C17—H17A	120.1

C7—N1—N2—C8	178.22 (16)	C10—S2—C8—S1	17.80 (12)
C6—C1—C2—F1	−177.56 (17)	C9—S1—C8—N2	−174.67 (17)
C6—C1—C2—C3	1.1 (3)	C9—S1—C8—S2	4.65 (12)
F1—C2—C3—C4	177.36 (18)	C8—S1—C9—C10	−31.34 (14)
C1—C2—C3—C4	−1.3 (3)	S1—C9—C10—S2	46.97 (15)
C2—C3—C4—C5	0.5 (3)	C8—S2—C10—C9	−38.84 (15)
C3—C4—C5—C6	0.4 (3)	C7—O1—C11—O2	−1.9 (2)
C2—C1—C6—C5	−0.1 (3)	C7—O1—C11—C12	177.88 (12)
C2—C1—C6—C7	179.21 (16)	O2—C11—C12—C17	−3.1 (3)
C4—C5—C6—C1	−0.6 (3)	O1—C11—C12—C17	177.18 (14)
C4—C5—C6—C7	−179.95 (17)	O2—C11—C12—C13	178.22 (16)
N2—N1—C7—O1	−4.3 (2)	O1—C11—C12—C13	−1.5 (2)
N2—N1—C7—C6	179.92 (15)	C17—C12—C13—C14	−1.8 (2)
C11—O1—C7—N1	89.6 (2)	C11—C12—C13—C14	176.82 (14)
C11—O1—C7—C6	−94.45 (18)	C12—C13—C14—F2	−178.49 (14)
C1—C6—C7—N1	−1.9 (3)	C12—C13—C14—C15	0.6 (3)
C5—C6—C7—N1	177.38 (17)	F2—C14—C15—C16	179.79 (15)
C1—C6—C7—O1	−177.96 (16)	C13—C14—C15—C16	0.7 (3)
C5—C6—C7—O1	1.4 (2)	C14—C15—C16—C17	−0.8 (3)
N1—N2—C8—S2	−176.83 (12)	C15—C16—C17—C12	−0.4 (3)
N1—N2—C8—S1	2.5 (2)	C13—C12—C17—C16	1.8 (2)
C10—S2—C8—N2	−162.83 (16)	C11—C12—C17—C16	−176.95 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O2ⁱ	0.97	2.49	3.280 (2)	138
C10—H10B···O2ⁱⁱ	0.97	2.46	3.248 (2)	138
C13—H13A···N1ⁱⁱⁱ	0.93	2.50	3.424 (3)	176

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₂F₂N₂O₂S₂
M_r	378.41
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	9.124 (4), 9.757 (4), 10.738 (4)
α, β, γ (°)	104.592 (3), 110.326 (5), 101.194 (4)
V (Å³)	824.6 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2009)
T_min, T_max	0.932, 0.932
No. of measured, independent and observed [I > 2σ(I)] reflections	7057, 2896, 2098
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.076, 0.96
No. of reflections	2896
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.20

Computer programs: CrystalClear-SM Expert (Rigaku/MSC, 2009), 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
C9—H9B···O2ⁱ	0.97	2.49	3.280 (2)	138.1
C10—H10B···O2ⁱⁱ	0.97	2.46	3.248 (2)	137.9
C13—H13A···N1ⁱⁱⁱ	0.93	2.50	3.424 (3)	175.7

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

Acknowledgements

The author thanks the Jining University Foundation (No. 2012YYJJ07) for financial support of this work.

References

Rigaku/MSC (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tanaka, H., Araki, F., Harada, T. & Kurono, H. (1976). Jpn Patent No. 51151326A. Google Scholar
Wang, Y., Li, Z. H. & Gao, N. (1994). Yaoxue Xuebao, 29, 78–80. Google Scholar

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Volume 69| Part 4| April 2013| Page o571

doi:10.1107/S1600536813007319

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

(E)-[2-(1,3-Di­thio­lan-2-yl­­idene)hydrazinyl­­idene](3-fluoro­phen­yl)methyl 3-fluoro­benzoate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-[2-(1,3-Dithiolan-2-ylidene)hydrazinylidene](3-fluorophenyl)methyl 3-fluorobenzoate