2-(4-Fluoro­benzyl­idene)-N-(4-meth­oxy­benzylidene)-1,3,4-thia­diazol-2-amine

He, Q.; An, K.; Wang, P.; Yu, P.; Wan, R.

doi:10.1107/S160053681002221X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1716

doi:10.1107/S160053681002221X

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2-(4-Fluorobenzylidene)-N-(4-methoxybenzylidene)-1,3,4-thiadiazol-2-amine

Qiu He,^a Kang An,^a Peng Wang,^a Peng Yu ^a and Rong Wan ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: rwan@njut.edu.cn

(Received 22 May 2010; accepted 10 June 2010; online 18 June 2010)

The title compound, C₁₆H₁₂FN₃OS, was synthesized by the reaction of 5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-amine and 4-fluorobenzaldehyde. An intramolecular C—H⋯S hydrogen bond results in the formation of two five-membered rings. In the crystal structure, intermolecular C—H⋯N hydrogen bonding links the molecules, forming a two-dimensional network.

Related literature

For the biological activity of 1,3,4-thiadiazole derivatives, see: Nakagawa et al. (1996 ); Wang et al. (1999 ).

Experimental

Crystal data

C₁₆H₁₂FN₃OS
M_r = 313.35
Orthorhombic, P c a 2₁
a = 7.4580 (15) Å
b = 17.821 (4) Å
c = 10.891 (2) Å
V = 1447.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.932, T_max = 0.977
2617 measured reflections
2617 independent reflections
1965 reflections with I > 2σ(I)
R_int = 0.045
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.132
S = 1.01
2617 reflections
199 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ), 1062 Friedel pairs
Flack parameter: −0.11 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯S	0.93	2.59	3.043 (5)	110
C12—H12A⋯S	0.93	2.75	3.138 (4)	106
C12—H12A⋯N3ⁱ	0.93	2.62	3.451 (6)	148
Symmetry code: (i) $[-x+2, -y+1, z-{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002221X/hg2691sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681002221X/hg2691Isup2.hkl

checkCIF report

Comment top

1,3,4-Thiadiazole derivatives represent an interesting class of compounds possessing broad spectrum biological activities (Nakagawa et al., 1996; Wang et al., 1999). These compounds are known to exhibit diverse biological effects, such as insecticidal, fungicidal activities (Wang et al., 1999).

We report herein the crystal structure of the title compound,(I). In the molecule of the title compound (Fig. 1), bond lengths are within normal ranges. Rings A(C2—C7), B(S/C9/N2/N3/C10) and C(C11—C16) are planar. The dihedral angle between them is A/B = 21.4 (1) Å, A/C=29.6 (3)Å and B/C= 10.7 (4) Å. The intramolecular C—H···S hydrogen bonds (Table 1) result in the formation of two planar five-membered rings D(H8A/C8/N1/C9/S) and E(S/H12A/C12/C11/C10). They are oriented with respect to the adjacent rings at dihedral angles of A/D= 11.6 (4) Å, B/D= 14.1 (4) Å, C/D= 24.5 (1) Å, A/E= 27.4 (1) Å, B/E= 6.1 (1) Å, C/E= 8.2 (1)Å and D/E= 19.5 (1) Å. In the crystal structure, intermolecular C—H···S hydrogen bond (Table 1) links the molecules to form a two-dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For related literature, see: Nakagawa et al. (1996); Wang et al. (1999).

Experimental top

5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-amine(5 mmol) and 4-fluorobenzaldehyde(5 mmol) were added in toluene (50 ml). The water was removed by distillation for 5 h. The reaction mixture was left to cool to room temperature, filtered, and the filter cake was crystallized from acetone to give pure compound (I) (m.p. 412–414 K). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an acetone solution.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed line.
	Fig. 2. A partial packing diagram of(I). Hydrogen bonds are shown as dashed lines.

2-(4-Fluorobenzylidene)-N-(4-methoxybenzylidene)-1,3,4-thiadiazol-2-amine top

Crystal data top

C₁₆H₁₂FN₃OS	D_x = 1.438 Mg m⁻³
M_r = 313.35	Melting point = 412–414 K
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac -2ac	Cell parameters from 25 reflections
a = 7.4580 (15) Å	θ = 9–13°
b = 17.821 (4) Å	µ = 0.24 mm⁻¹
c = 10.891 (2) Å	T = 293 K
V = 1447.5 (5) Å³	Block, colourless
Z = 4	0.30 × 0.30 × 0.10 mm
F(000) = 648

Data collection top

Enraf–Nonius CAD-4 diffractometer	1965 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.045
Graphite monochromator	θ_max = 25.3°, θ_min = 1.1°
ω/2θ scans	h = −8→0
Absorption correction: ψ scan (North et al., 1968)	k = 0→21
T_min = 0.932, T_max = 0.977	l = −13→13
2617 measured reflections	3 standard reflections every 200 reflections
2617 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.078P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2617 reflections	Δρ_max = 0.33 e Å⁻³
199 parameters	Δρ_min = −0.17 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1062 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.11 (13)

Crystal data top

C₁₆H₁₂FN₃OS	V = 1447.5 (5) Å³
M_r = 313.35	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 7.4580 (15) Å	µ = 0.24 mm⁻¹
b = 17.821 (4) Å	T = 293 K
c = 10.891 (2) Å	0.30 × 0.30 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1965 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.045
T_min = 0.932, T_max = 0.977	3 standard reflections every 200 reflections
2617 measured reflections	intensity decay: 1%
2617 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.132	Δρ_max = 0.33 e Å⁻³
S = 1.01	Δρ_min = −0.17 e Å⁻³
2617 reflections	Absolute structure: Flack (1983), 1062 Friedel pairs
199 parameters	Absolute structure parameter: −0.11 (13)
1 restraint

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
S	0.92308 (13)	0.41730 (5)	0.79211 (10)	0.0604 (3)
O	0.9032 (5)	−0.04222 (18)	0.5620 (3)	0.0858 (10)
F	0.8635 (5)	0.78682 (14)	0.8637 (3)	0.0990 (9)
N1	0.8911 (5)	0.2684 (2)	0.8632 (3)	0.0645 (10)
N2	0.8471 (5)	0.3651 (2)	1.0054 (3)	0.0687 (9)
N3	0.8461 (5)	0.4421 (2)	1.0171 (3)	0.0654 (9)
C1	0.9071 (7)	−0.1065 (3)	0.6422 (6)	0.0918 (16)
H1B	0.9074	−0.1516	0.5940	0.138*
H1C	0.8031	−0.1060	0.6942	0.138*
H1D	1.0132	−0.1048	0.6920	0.138*
C2	0.9047 (6)	0.0268 (3)	0.6164 (4)	0.0678 (12)
C3	0.8810 (6)	0.0860 (2)	0.5372 (4)	0.0739 (12)
H3B	0.8684	0.0770	0.4535	0.089*
C4	0.8755 (6)	0.1585 (3)	0.5806 (4)	0.0687 (11)
H4A	0.8579	0.1981	0.5262	0.082*
C5	0.8963 (5)	0.1733 (2)	0.7064 (4)	0.0603 (10)
C6	0.9228 (5)	0.1129 (2)	0.7838 (5)	0.0657 (10)
H6A	0.9388	0.1217	0.8673	0.079*
C7	0.9261 (6)	0.0401 (3)	0.7411 (4)	0.0715 (13)
H7A	0.9425	0.0003	0.7952	0.086*
C8	0.8852 (6)	0.2493 (3)	0.7494 (4)	0.0643 (11)
H8A	0.8730	0.2871	0.6912	0.077*
C9	0.8836 (5)	0.3439 (2)	0.8931 (4)	0.0574 (10)
C10	0.8857 (5)	0.4763 (2)	0.9128 (3)	0.0542 (9)
C11	0.8879 (5)	0.5579 (2)	0.9023 (3)	0.0512 (9)
C12	0.9457 (5)	0.5931 (2)	0.7942 (5)	0.0611 (9)
H12A	0.9893	0.5640	0.7298	0.073*
C13	0.9392 (5)	0.6695 (2)	0.7818 (5)	0.0661 (10)
H13A	0.9787	0.6924	0.7099	0.079*
C14	0.8735 (6)	0.7118 (2)	0.8768 (4)	0.0673 (11)
C15	0.8172 (6)	0.6802 (3)	0.9853 (4)	0.0709 (12)
H15A	0.7758	0.7101	1.0492	0.085*
C16	0.8234 (5)	0.6033 (2)	0.9975 (3)	0.0606 (10)
H16A	0.7841	0.5813	1.0701	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0706 (6)	0.0737 (6)	0.0370 (4)	−0.0041 (5)	0.0021 (5)	0.0022 (6)
O	0.120 (3)	0.064 (2)	0.073 (2)	0.0014 (18)	0.0043 (19)	0.0027 (16)
F	0.140 (2)	0.0664 (16)	0.091 (2)	−0.0069 (16)	−0.0093 (18)	0.0074 (14)
N1	0.064 (2)	0.077 (3)	0.052 (2)	−0.0011 (18)	−0.0054 (17)	0.0085 (18)
N2	0.082 (2)	0.084 (2)	0.0407 (18)	−0.0013 (19)	−0.0027 (17)	0.0109 (16)
N3	0.086 (2)	0.076 (2)	0.0349 (17)	−0.0007 (19)	0.0027 (16)	0.0037 (15)
C1	0.106 (4)	0.065 (3)	0.104 (4)	−0.001 (3)	0.014 (3)	0.013 (3)
C2	0.071 (3)	0.074 (3)	0.059 (3)	0.002 (2)	0.002 (2)	0.004 (2)
C3	0.094 (3)	0.079 (3)	0.049 (2)	0.005 (2)	−0.002 (2)	0.005 (2)
C4	0.085 (3)	0.070 (3)	0.051 (2)	0.002 (2)	0.000 (2)	0.0147 (19)
C5	0.061 (2)	0.070 (3)	0.050 (2)	−0.003 (2)	0.0007 (18)	0.0064 (19)
C6	0.075 (2)	0.074 (2)	0.048 (2)	0.0045 (19)	0.003 (2)	0.009 (3)
C7	0.080 (3)	0.071 (3)	0.063 (3)	0.012 (2)	0.000 (2)	0.014 (2)
C8	0.067 (2)	0.077 (3)	0.050 (2)	0.000 (2)	0.0010 (18)	0.0091 (19)
C9	0.057 (2)	0.073 (3)	0.0419 (19)	−0.0012 (19)	−0.0034 (16)	0.0054 (18)
C10	0.0435 (18)	0.085 (3)	0.0337 (18)	0.0011 (18)	−0.0032 (14)	0.0043 (17)
C11	0.0456 (19)	0.075 (3)	0.0328 (17)	−0.0029 (17)	−0.0051 (13)	0.0045 (18)
C12	0.059 (2)	0.086 (3)	0.0384 (16)	−0.0027 (18)	−0.003 (2)	0.003 (3)
C13	0.065 (2)	0.085 (3)	0.049 (2)	−0.010 (2)	−0.0044 (19)	0.006 (2)
C14	0.075 (3)	0.070 (3)	0.057 (3)	−0.004 (2)	−0.009 (2)	0.007 (2)
C15	0.081 (3)	0.082 (3)	0.049 (2)	0.005 (2)	−0.003 (2)	−0.007 (2)
C16	0.060 (2)	0.083 (3)	0.0388 (18)	0.001 (2)	0.0008 (18)	−0.0020 (18)

Geometric parameters (Å, º) top

S—C10	1.706 (4)	C4—H4A	0.9300
S—C9	1.734 (4)	C5—C6	1.381 (5)
O—C2	1.365 (6)	C5—C8	1.436 (6)
O—C1	1.441 (6)	C6—C7	1.379 (6)
F—C14	1.347 (5)	C6—H6A	0.9300
N1—C8	1.287 (6)	C7—H7A	0.9300
N1—C9	1.385 (5)	C8—H8A	0.9300
N2—C9	1.309 (5)	C10—C11	1.459 (6)
N2—N3	1.379 (5)	C11—C16	1.401 (5)
N3—C10	1.323 (5)	C11—C12	1.402 (7)
C1—H1B	0.9600	C12—C13	1.370 (5)
C1—H1C	0.9600	C12—H12A	0.9300
C1—H1D	0.9600	C13—C14	1.370 (7)
C2—C3	1.374 (6)	C13—H13A	0.9300
C2—C7	1.388 (6)	C14—C15	1.375 (6)
C3—C4	1.377 (6)	C15—C16	1.376 (6)
C3—H3B	0.9300	C15—H15A	0.9300
C4—C5	1.403 (6)	C16—H16A	0.9300

C10—S—C9	87.1 (2)	C2—C7—H7A	120.4
C2—O—C1	117.0 (4)	N1—C8—C5	124.2 (4)
C8—N1—C9	118.8 (4)	N1—C8—H8A	117.9
C9—N2—N3	112.0 (3)	C5—C8—H8A	117.9
C10—N3—N2	112.2 (3)	N2—C9—N1	120.5 (4)
O—C1—H1B	109.5	N2—C9—S	114.3 (3)
O—C1—H1C	109.5	N1—C9—S	125.2 (3)
H1B—C1—H1C	109.5	N3—C10—C11	122.0 (4)
O—C1—H1D	109.5	N3—C10—S	114.4 (3)
H1B—C1—H1D	109.5	C11—C10—S	123.5 (3)
H1C—C1—H1D	109.5	C16—C11—C12	118.0 (4)
O—C2—C3	114.8 (4)	C16—C11—C10	121.0 (3)
O—C2—C7	125.4 (4)	C12—C11—C10	121.0 (4)
C3—C2—C7	119.9 (4)	C13—C12—C11	121.1 (5)
C2—C3—C4	120.6 (4)	C13—C12—H12A	119.5
C2—C3—H3B	119.7	C11—C12—H12A	119.5
C4—C3—H3B	119.7	C14—C13—C12	119.0 (5)
C3—C4—C5	120.5 (4)	C14—C13—H13A	120.5
C3—C4—H4A	119.7	C12—C13—H13A	120.5
C5—C4—H4A	119.7	F—C14—C13	119.0 (4)
C6—C5—C4	117.8 (4)	F—C14—C15	118.8 (4)
C6—C5—C8	123.0 (4)	C13—C14—C15	122.2 (4)
C4—C5—C8	119.2 (4)	C14—C15—C16	118.7 (4)
C7—C6—C5	122.0 (4)	C14—C15—H15A	120.6
C7—C6—H6A	119.0	C16—C15—H15A	120.6
C5—C6—H6A	119.0	C15—C16—C11	121.0 (4)
C6—C7—C2	119.3 (4)	C15—C16—H16A	119.5
C6—C7—H7A	120.4	C11—C16—H16A	119.5

C9—N2—N3—C10	−1.3 (5)	C10—S—C9—N2	−0.2 (3)
C1—O—C2—C3	−173.1 (4)	C10—S—C9—N1	−179.1 (4)
C1—O—C2—C7	6.2 (7)	N2—N3—C10—C11	178.3 (3)
O—C2—C3—C4	178.5 (4)	N2—N3—C10—S	1.1 (4)
C7—C2—C3—C4	−0.9 (7)	C9—S—C10—N3	−0.5 (3)
C2—C3—C4—C5	0.8 (7)	C9—S—C10—C11	−177.7 (3)
C3—C4—C5—C6	0.2 (6)	N3—C10—C11—C16	−9.2 (6)
C3—C4—C5—C8	−178.3 (4)	S—C10—C11—C16	167.7 (3)
C4—C5—C6—C7	−1.1 (6)	N3—C10—C11—C12	174.2 (4)
C8—C5—C6—C7	177.5 (4)	S—C10—C11—C12	−8.8 (5)
C5—C6—C7—C2	0.9 (7)	C16—C11—C12—C13	−0.1 (6)
O—C2—C7—C6	−179.2 (4)	C10—C11—C12—C13	176.6 (3)
C3—C2—C7—C6	0.1 (7)	C11—C12—C13—C14	−0.5 (6)
C9—N1—C8—C5	178.4 (3)	C12—C13—C14—F	−178.6 (3)
C6—C5—C8—N1	−3.1 (7)	C12—C13—C14—C15	1.4 (7)
C4—C5—C8—N1	175.4 (4)	F—C14—C15—C16	178.5 (4)
N3—N2—C9—N1	179.8 (3)	C13—C14—C15—C16	−1.5 (7)
N3—N2—C9—S	0.9 (5)	C14—C15—C16—C11	0.9 (6)
C8—N1—C9—N2	164.0 (4)	C12—C11—C16—C15	−0.1 (6)
C8—N1—C9—S	−17.2 (6)	C10—C11—C16—C15	−176.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···S	0.93	2.59	3.043 (5)	110
C12—H12A···S	0.93	2.75	3.138 (4)	106
C12—H12A···N3ⁱ	0.93	2.62	3.451 (6)	148

Symmetry code: (i) −x+2, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂FN₃OS
M_r	313.35
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	7.4580 (15), 17.821 (4), 10.891 (2)
V (Å³)	1447.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.30 × 0.30 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.932, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	2617, 2617, 1965
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.132, 1.01
No. of reflections	2617
No. of parameters	199
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.17
Absolute structure	Flack (1983), 1062 Friedel pairs
Absolute structure parameter	−0.11 (13)

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), 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
C8—H8A···S	0.9300	2.5900	3.043 (5)	110.00
C12—H12A···S	0.9300	2.7500	3.138 (4)	106.00
C12—H12A···N3ⁱ	0.9300	2.6200	3.451 (6)	148.00

Symmetry code: (i) −x+2, −y+1, z−1/2.

Acknowledgements

The authors gratefully acknowledge Professor Hua-Qin Wang of the Analysis Centre, Nanjing University, for providing the Enraf–Nonius CAD-4 diffractometer for this research project.

References

Enraf–Nonius (1989). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
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Volume 66| Part 7| July 2010| Page o1716

doi:10.1107/S160053681002221X

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

2-(4-Fluoro­benzyl­­idene)-N-(4-meth­­oxy­benzyl­idene)-1,3,4-thia­diazol-2-amine

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Experimental

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organic compounds

2-(4-Fluorobenzylidene)-N-(4-methoxybenzylidene)-1,3,4-thiadiazol-2-amine