N'-[(1E)-(2,6-Difluoro-phen-yl)methyl-idene]thio-phene-2-carbohydrazide.

In the title compound, C(12)H(8)F(2)N(2)OS, the thienyl ring is disordered over two positions, with the S atom of the major component [occupancy = 75.03 (18)%] oriented away from an ortho-F atom of the benzene ring. The mol-ecule is nearly planar, the dihedral angle between the thio-phene and benzene rings being 6.19 (18) (in the major component) or 3.5 (6)° (in the minor component). The azomethine C=N double-bond in the mol-ecule is of an E configuration. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, generating inversion dimers.

Related literature

For a related structure, see: Alanazi et al. (2012 ▶).

Experimental

Crystal data

C12H8F2N2OS

M = 266.26

Triclinic,

a = 6.5032 (3) Å

b = 7.7516 (4) Å

c = 11.5224 (5) Å

α = 95.184 (4)°

β = 103.344 (4)°

γ = 94.285 (4)°

V = 560.11 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 100 K

0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.888, T max = 0.942

8250 measured reflections

2594 independent reflections

2174 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.108

S = 1.07

2594 reflections

180 parameters

24 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681105611X/xu5416sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681105611X/xu5416Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681105611X/xu5416Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H8F2N2OS	Z = 2
Mr = 266.26	F(000) = 272
Triclinic, P1	Dx = 1.579 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5032 (3) Å	Cell parameters from 3787 reflections
b = 7.7516 (4) Å	θ = 2.7–27.5°
c = 11.5224 (5) Å	µ = 0.30 mm−1
α = 95.184 (4)°	T = 100 K
β = 103.344 (4)°	Wedge, colorless
γ = 94.285 (4)°	0.40 × 0.30 × 0.20 mm
V = 560.11 (5) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	2594 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2174 reflections with I > 2σ(I)
Mirror	Rint = 0.035
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.7°
ω scan	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −10→10
Tmin = 0.888, Tmax = 0.942	l = −15→14
8250 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0585P)2 + 0.1004P] where P = (Fo2 + 2Fc2)/3
2594 reflections	(Δ/σ)max = 0.001
180 parameters	Δρmax = 0.33 e Å−3
24 restraints	Δρmin = −0.28 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.61235 (9)	0.40630 (10)	0.12814 (6)	0.01924 (19)	0.7503 (18)
S1'	0.9967 (5)	0.2911 (5)	0.2831 (4)	0.0226 (7)	0.2497 (18)
F1	1.02233 (15)	0.19692 (13)	0.85830 (8)	0.0285 (3)
F2	1.26733 (15)	0.14995 (13)	0.50356 (8)	0.0270 (3)
O1	0.47384 (17)	0.48037 (15)	0.34181 (10)	0.0228 (3)
N1	0.7178 (2)	0.37086 (17)	0.47830 (12)	0.0188 (3)
N2	0.8961 (2)	0.28597 (16)	0.51113 (11)	0.0178 (3)
C1	0.8196 (10)	0.3496 (7)	0.0668 (6)	0.0214 (8)	0.7503 (18)
H1A	0.8126	0.3501	−0.0165	0.026*	0.7503 (18)
C2	0.9871 (9)	0.3058 (8)	0.1414 (3)	0.0199 (7)	0.7503 (18)
H2	1.1127	0.2725	0.1205	0.024*	0.7503 (18)
C3	0.9481 (7)	0.3168 (7)	0.2667 (5)	0.0226 (7)	0.7503 (18)
H3	1.0483	0.2915	0.3357	0.027*	0.7503 (18)
C1'	0.6702 (15)	0.4020 (15)	0.1526 (9)	0.01924 (19)	0.25
H1'	0.5350	0.4436	0.1277	0.023*	0.2497 (18)
C2'	0.801 (3)	0.371 (2)	0.074 (2)	0.0214 (8)	0.25
H2'	0.7827	0.3824	−0.0092	0.026*	0.2497 (18)
C3'	0.983 (3)	0.314 (3)	0.1659 (13)	0.0199 (7)	0.25
H3'	1.1048	0.2898	0.1375	0.024*	0.2497 (18)
C4	0.7509 (2)	0.36777 (19)	0.26883 (13)	0.0172 (3)
C5	0.6407 (2)	0.40831 (19)	0.36486 (13)	0.0176 (3)
C7	0.9443 (2)	0.26314 (19)	0.62276 (14)	0.0176 (3)
H7	0.8547	0.3020	0.6721	0.021*
C8	1.1326 (2)	0.17935 (19)	0.67688 (13)	0.0167 (3)
C9	1.1710 (2)	0.1525 (2)	0.79783 (13)	0.0190 (3)
C10	1.3490 (3)	0.0862 (2)	0.86064 (14)	0.0225 (4)
H10	1.3680	0.0733	0.9435	0.027*
C11	1.4994 (3)	0.0391 (2)	0.79913 (15)	0.0229 (4)
H11	1.6238	−0.0069	0.8401	0.027*
C12	1.4694 (2)	0.0587 (2)	0.67816 (15)	0.0217 (3)
H12	1.5714	0.0246	0.6356	0.026*
C13	1.2902 (2)	0.1279 (2)	0.62060 (14)	0.0192 (3)
H1	0.656 (3)	0.409 (3)	0.535 (2)	0.040 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0198 (4)	0.0239 (3)	0.0153 (3)	0.0069 (3)	0.0043 (2)	0.0045 (2)
S1'	0.0216 (14)	0.0257 (11)	0.0218 (11)	0.0042 (9)	0.0074 (10)	0.0018 (8)
F1	0.0271 (5)	0.0443 (6)	0.0201 (5)	0.0167 (5)	0.0120 (4)	0.0075 (4)
F2	0.0266 (5)	0.0396 (6)	0.0208 (5)	0.0157 (4)	0.0119 (4)	0.0080 (4)
O1	0.0185 (6)	0.0310 (6)	0.0209 (6)	0.0117 (5)	0.0054 (5)	0.0045 (5)
N1	0.0168 (6)	0.0247 (7)	0.0175 (6)	0.0095 (5)	0.0071 (5)	0.0026 (5)
N2	0.0135 (6)	0.0196 (7)	0.0208 (7)	0.0053 (5)	0.0043 (5)	0.0026 (5)
C1	0.0245 (12)	0.0234 (14)	0.0196 (10)	0.0062 (10)	0.0103 (8)	0.0032 (10)
C2	0.0207 (8)	0.0267 (10)	0.0157 (18)	0.0046 (7)	0.0111 (13)	0.0002 (14)
C3	0.0216 (14)	0.0257 (11)	0.0218 (11)	0.0042 (9)	0.0074 (10)	0.0018 (8)
C1'	0.0198 (4)	0.0239 (3)	0.0153 (3)	0.0069 (3)	0.0043 (2)	0.0045 (2)
C2'	0.0245 (12)	0.0234 (14)	0.0196 (10)	0.0062 (10)	0.0103 (8)	0.0032 (10)
C3'	0.0207 (8)	0.0267 (10)	0.0157 (18)	0.0046 (7)	0.0111 (13)	0.0002 (14)
C4	0.0167 (7)	0.0182 (7)	0.0172 (7)	0.0026 (6)	0.0050 (6)	0.0018 (6)
C5	0.0168 (7)	0.0174 (7)	0.0192 (7)	0.0029 (6)	0.0055 (6)	0.0009 (6)
C7	0.0157 (7)	0.0175 (7)	0.0210 (7)	0.0035 (6)	0.0071 (6)	0.0014 (6)
C8	0.0148 (7)	0.0153 (7)	0.0202 (8)	0.0031 (6)	0.0041 (6)	0.0016 (6)
C9	0.0187 (7)	0.0210 (8)	0.0194 (8)	0.0056 (6)	0.0076 (6)	0.0015 (6)
C10	0.0239 (8)	0.0248 (8)	0.0184 (8)	0.0057 (7)	0.0024 (6)	0.0047 (6)
C11	0.0165 (7)	0.0216 (8)	0.0298 (9)	0.0063 (6)	0.0018 (7)	0.0053 (7)
C12	0.0172 (7)	0.0217 (8)	0.0286 (8)	0.0060 (6)	0.0089 (6)	0.0033 (6)
C13	0.0197 (8)	0.0186 (7)	0.0205 (8)	0.0027 (6)	0.0069 (6)	0.0032 (6)

S1—C4	1.7269 (16)	C1'—C2'	1.40 (2)
S1—C1	1.727 (6)	C1'—H1'	0.9500
S1'—C3'	1.360 (16)	C2'—C3'	1.52 (3)
S1'—C4	1.725 (3)	C2'—H2'	0.9500
F1—C9	1.3624 (17)	C3'—H3'	0.9500
F2—C13	1.3500 (18)	C4—C5	1.474 (2)
O1—C5	1.2425 (18)	C7—C8	1.466 (2)
N1—C5	1.354 (2)	C7—H7	0.9500
N1—N2	1.3702 (18)	C8—C9	1.395 (2)
N1—H1	0.88 (2)	C8—C13	1.397 (2)
N2—C7	1.284 (2)	C9—C10	1.377 (2)
C1—C2	1.311 (8)	C10—C11	1.385 (2)
C1—H1A	0.9500	C10—H10	0.9500
C2—C3	1.519 (7)	C11—C12	1.386 (2)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.374 (5)	C12—C13	1.374 (2)
C3—H3	0.9500	C12—H12	0.9500
C1'—C4	1.378 (10)
C4—S1—C1	91.0 (2)	C5—C4—S1'	127.47 (18)
C3'—S1'—C4	88.3 (9)	C3—C4—S1	111.5 (3)
C5—N1—N2	123.04 (13)	C5—C4—S1	114.07 (11)
C5—N1—H1	118.9 (14)	O1—C5—N1	118.90 (13)
N2—N1—H1	117.9 (14)	O1—C5—C4	119.41 (14)
C7—N2—N1	113.74 (13)	N1—C5—C4	121.68 (14)
C2—C1—S1	116.3 (5)	N2—C7—C8	122.42 (14)
C2—C1—H1A	121.9	N2—C7—H7	118.8
S1—C1—H1A	121.9	C8—C7—H7	118.8
C1—C2—C3	109.0 (5)	C9—C8—C13	114.10 (14)
C1—C2—H2	125.5	C9—C8—C7	119.41 (14)
C3—C2—H2	125.5	C13—C8—C7	126.42 (14)
C4—C3—C2	112.2 (4)	F1—C9—C10	117.74 (14)
C4—C3—H3	123.9	F1—C9—C8	117.47 (14)
C2—C3—H3	123.9	C10—C9—C8	124.78 (14)
C4—C1'—C2'	115.3 (11)	C9—C10—C11	117.90 (15)
C4—C1'—H1'	122.3	C9—C10—H10	121.0
C2'—C1'—H1'	122.3	C11—C10—H10	121.0
C1'—C2'—C3'	96.1 (16)	C10—C11—C12	120.42 (15)
C1'—C2'—H2'	131.9	C10—C11—H11	119.8
C3'—C2'—H2'	131.9	C12—C11—H11	119.8
S1'—C3'—C2'	129.6 (16)	C13—C12—C11	119.10 (15)
S1'—C3'—H3'	115.2	C13—C12—H12	120.5
C2'—C3'—H3'	115.2	C11—C12—H12	120.5
C3—C4—C1'	103.4 (5)	F2—C13—C12	117.98 (14)
C3—C4—C5	134.2 (3)	F2—C13—C8	118.33 (14)
C1'—C4—C5	121.8 (4)	C12—C13—C8	123.67 (15)
C1'—C4—S1'	110.5 (5)
C5—N1—N2—C7	179.73 (14)	C3—C4—C5—O1	167.6 (3)
C4—S1—C1—C2	−0.8 (5)	C1'—C4—C5—O1	−2.3 (6)
S1—C1—C2—C3	0.4 (7)	S1'—C4—C5—O1	172.3 (2)
C1—C2—C3—C4	0.4 (7)	S1—C4—C5—O1	−6.89 (19)
C4—C1'—C2'—C3'	−1.0 (16)	C3—C4—C5—N1	−11.6 (4)
C4—S1'—C3'—C2'	−4.0 (19)	C1'—C4—C5—N1	178.5 (5)
C1'—C2'—C3'—S1'	4(2)	S1'—C4—C5—N1	−6.9 (3)
C2—C3—C4—C1'	−4.4 (7)	S1—C4—C5—N1	173.89 (12)
C2—C3—C4—C5	−175.6 (3)	N1—N2—C7—C8	−178.28 (13)
C2—C3—C4—S1'	155 (3)	N2—C7—C8—C9	−177.48 (14)
C2—C3—C4—S1	−1.0 (5)	N2—C7—C8—C13	5.7 (3)
C2'—C1'—C4—C3	1.9 (12)	C13—C8—C9—F1	−178.95 (13)
C2'—C1'—C4—C5	174.5 (10)	C7—C8—C9—F1	3.9 (2)
C2'—C1'—C4—S1'	−0.9 (13)	C13—C8—C9—C10	1.8 (2)
C2'—C1'—C4—S1	−157 (4)	C7—C8—C9—C10	−175.39 (14)
C3'—S1'—C4—C3	−19 (3)	F1—C9—C10—C11	179.29 (14)
C3'—S1'—C4—C1'	2.6 (10)	C8—C9—C10—C11	−1.4 (2)
C3'—S1'—C4—C5	−172.6 (9)	C9—C10—C11—C12	0.0 (2)
C3'—S1'—C4—S1	6.6 (9)	C10—C11—C12—C13	1.0 (2)
C1—S1—C4—C3	1.0 (3)	C11—C12—C13—F2	178.28 (14)
C1—S1—C4—C1'	23 (3)	C11—C12—C13—C8	−0.6 (2)
C1—S1—C4—C5	176.8 (2)	C9—C8—C13—F2	−179.60 (13)
C1—S1—C4—S1'	−2.4 (3)	C7—C8—C13—F2	−2.7 (2)
N2—N1—C5—O1	177.55 (13)	C9—C8—C13—C12	−0.7 (2)
N2—N1—C5—C4	−3.2 (2)	C7—C8—C13—C12	176.23 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88 (2)	1.97 (2)	2.856 (2)	174 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88 (2)	1.97 (2)	2.856 (2)	174 (2)

Symmetry code: (i) .