(E)-3-Chloro-N'-(2-fluoro-benzyl-idene)thio-phene-2-carbohydrazide.

The title compound, C12H8ClFN2OS, is a hydrazide derivative adopting an E conformation with an azomethine N=C double bond length of 1.272 (2) Å. The mol-ecular skeleton is approximately planar; the terminal five- and six-membered rings form a dihedral angle of 5.47 (9)°. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds into zigzag chains propagating in [100].

Related literature

For the applications and biological activity of hydrazones, see: Taha et al. (2013 ▶); Musharraf et al. (2012 ▶); Melnyk et al. (2006 ▶); Terzioglu & Gursoy (2003 ▶). For the crystal structures of related compounds, see: Alanazi et al. (2012a ▶,b ▶).

Experimental

Crystal data

C12H8ClFN2OS

M = 282.71

Orthorhombic,

a = 5.6833 (3) Å

b = 13.0817 (6) Å

c = 16.4001 (8) Å

V = 1219.30 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 302 K

0.55 × 0.46 × 0.03 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.776, T max = 0.985

47474 measured reflections

2255 independent reflections

2210 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.065

S = 1.09

2255 reflections

168 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.12 e Å−3

Absolute structure: Flack (1983 ▶), 916 Friedel pairs

Absolute structure parameter: 0.02 (5)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814011568/cv5453sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814011568/cv5453Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814011568/cv5453Isup3.cml

CCDC reference: 1003818

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H8ClFN2OS	F(000) = 576
Mr = 282.71	Dx = 1.540 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9699 reflections
a = 5.6833 (3) Å	θ = 3.1–25.5°
b = 13.0817 (6) Å	µ = 0.48 mm−1
c = 16.4001 (8) Å	T = 302 K
V = 1219.30 (10) Å3	Slab, colourless
Z = 4	0.55 × 0.46 × 0.03 mm

Bruker SMART APEX CCD area-detector diffractometer	2255 independent reflections
Radiation source: fine-focus sealed tube	2210 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 83.66 pixels mm-1	θmax = 25.5°, θmin = 3.1°
ω scan	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −15→15
Tmin = 0.776, Tmax = 0.985	l = −19→19
47474 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.023	w = 1/[σ2(Fo2) + (0.0388P)2 + 0.1642P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.065	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.15 e Å−3
2255 reflections	Δρmin = −0.12 e Å−3
168 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.021 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 916 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.02 (5)

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.

	x	y	z	Uiso*/Ueq
S1	0.17368 (8)	0.52165 (3)	0.22226 (3)	0.05051 (13)
Cl1	−0.35177 (8)	0.75148 (4)	0.21939 (3)	0.06171 (15)
F1	0.9968 (2)	0.52634 (9)	−0.05506 (7)	0.0641 (3)
O1	−0.0135 (3)	0.75985 (10)	0.08685 (8)	0.0592 (3)
N1	0.2895 (2)	0.65589 (9)	0.06578 (7)	0.0424 (3)
H1A	0.3269	0.6912	0.0235	0.051*
N2	0.4234 (2)	0.57273 (10)	0.08483 (8)	0.0402 (3)
C1	0.7057 (3)	0.39194 (12)	0.10909 (10)	0.0498 (4)
H1B	0.5728	0.3967	0.1420	0.060*
C2	0.8577 (4)	0.31121 (13)	0.11894 (13)	0.0602 (5)
H2B	0.8273	0.2620	0.1584	0.072*
C3	1.0558 (4)	0.30280 (15)	0.07046 (15)	0.0652 (5)
H3A	1.1577	0.2479	0.0776	0.078*
C4	1.1029 (3)	0.37504 (14)	0.01183 (13)	0.0618 (5)
H4A	1.2357	0.3698	−0.0210	0.074*
C5	0.9492 (3)	0.45490 (13)	0.00305 (10)	0.0484 (4)
C6	0.7486 (3)	0.46727 (12)	0.04998 (9)	0.0428 (3)
C7	0.5958 (3)	0.55497 (12)	0.03748 (9)	0.0430 (4)
H7A	0.6247	0.5989	−0.0059	0.052*
C8	0.1010 (3)	0.68555 (11)	0.11008 (9)	0.0396 (3)
C9	0.0325 (3)	0.62923 (11)	0.18418 (9)	0.0392 (3)
C10	−0.1608 (3)	0.65037 (12)	0.23145 (10)	0.0459 (3)
C11	−0.1957 (4)	0.58121 (15)	0.29608 (10)	0.0599 (5)
H11A	−0.3197	0.5852	0.3330	0.072*
C12	−0.0282 (4)	0.50870 (17)	0.29804 (12)	0.0654 (5)
H12A	−0.005 (5)	0.4586 (17)	0.3352 (16)	0.086 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0573 (2)	0.0498 (2)	0.0445 (2)	0.00003 (18)	−0.00151 (19)	0.01644 (17)
Cl1	0.0550 (2)	0.0632 (3)	0.0670 (3)	0.0061 (2)	0.0052 (2)	−0.0115 (2)
F1	0.0649 (6)	0.0732 (7)	0.0542 (6)	−0.0086 (6)	0.0104 (5)	−0.0038 (5)
O1	0.0655 (8)	0.0571 (7)	0.0551 (7)	0.0185 (6)	0.0050 (6)	0.0202 (6)
N1	0.0472 (7)	0.0429 (6)	0.0370 (6)	0.0018 (6)	0.0005 (6)	0.0104 (5)
N2	0.0439 (7)	0.0378 (6)	0.0389 (6)	−0.0010 (5)	−0.0040 (5)	0.0050 (5)
C1	0.0503 (9)	0.0459 (8)	0.0533 (9)	0.0002 (7)	−0.0053 (8)	0.0012 (7)
C2	0.0631 (11)	0.0470 (9)	0.0706 (11)	0.0036 (8)	−0.0161 (10)	0.0002 (8)
C3	0.0560 (11)	0.0507 (10)	0.0889 (15)	0.0117 (8)	−0.0153 (11)	−0.0148 (10)
C4	0.0455 (10)	0.0655 (11)	0.0746 (12)	0.0037 (8)	−0.0020 (9)	−0.0256 (10)
C5	0.0493 (9)	0.0503 (9)	0.0457 (8)	−0.0072 (7)	−0.0041 (7)	−0.0125 (7)
C6	0.0420 (8)	0.0443 (8)	0.0421 (7)	−0.0034 (6)	−0.0059 (6)	−0.0059 (6)
C7	0.0474 (8)	0.0436 (8)	0.0380 (7)	−0.0045 (6)	−0.0026 (6)	0.0026 (6)
C8	0.0437 (8)	0.0395 (7)	0.0355 (7)	−0.0019 (6)	−0.0057 (6)	0.0051 (6)
C9	0.0430 (8)	0.0401 (7)	0.0345 (7)	−0.0050 (6)	−0.0064 (6)	0.0026 (6)
C10	0.0476 (8)	0.0497 (8)	0.0406 (8)	−0.0089 (7)	−0.0018 (7)	−0.0049 (6)
C11	0.0673 (11)	0.0673 (11)	0.0452 (9)	−0.0139 (10)	0.0113 (8)	0.0027 (8)
C12	0.0806 (14)	0.0708 (12)	0.0447 (9)	−0.0108 (11)	0.0056 (9)	0.0191 (9)

S1—C12	1.700 (2)	C3—C4	1.375 (3)
S1—C9	1.7362 (15)	C3—H3A	0.9300
Cl1—C10	1.7224 (18)	C4—C5	1.369 (3)
F1—C5	1.362 (2)	C4—H4A	0.9300
O1—C8	1.2304 (19)	C5—C6	1.385 (2)
N1—C8	1.351 (2)	C6—C7	1.453 (2)
N1—N2	1.3639 (17)	C7—H7A	0.9300
N1—H1A	0.8600	C8—C9	1.474 (2)
N2—C7	1.272 (2)	C9—C10	1.373 (2)
C1—C2	1.374 (2)	C10—C11	1.408 (2)
C1—C6	1.404 (2)	C11—C12	1.344 (3)
C1—H1B	0.9300	C11—H11A	0.9300
C2—C3	1.382 (3)	C12—H12A	0.90 (2)
C2—H2B	0.9300
C12—S1—C9	91.82 (10)	C5—C6—C7	120.37 (15)
C8—N1—N2	123.24 (12)	C1—C6—C7	123.21 (15)
C8—N1—H1A	118.4	N2—C7—C6	121.23 (14)
N2—N1—H1A	118.4	N2—C7—H7A	119.4
C7—N2—N1	115.83 (13)	C6—C7—H7A	119.4
C2—C1—C6	120.76 (17)	O1—C8—N1	118.68 (14)
C2—C1—H1B	119.6	O1—C8—C9	120.69 (14)
C6—C1—H1B	119.6	N1—C8—C9	120.63 (13)
C1—C2—C3	120.37 (18)	C10—C9—C8	125.21 (14)
C1—C2—H2B	119.8	C10—C9—S1	109.27 (11)
C3—C2—H2B	119.8	C8—C9—S1	125.43 (12)
C4—C3—C2	120.41 (18)	C9—C10—C11	114.11 (16)
C4—C3—H3A	119.8	C9—C10—Cl1	126.46 (13)
C2—C3—H3A	119.8	C11—C10—Cl1	119.42 (14)
C5—C4—C3	118.29 (18)	C12—C11—C10	111.83 (17)
C5—C4—H4A	120.9	C12—C11—H11A	124.1
C3—C4—H4A	120.9	C10—C11—H11A	124.1
F1—C5—C4	118.06 (17)	C11—C12—S1	112.96 (14)
F1—C5—C6	118.18 (16)	C11—C12—H12A	129.0 (18)
C4—C5—C6	123.76 (18)	S1—C12—H12A	117.9 (18)
C5—C6—C1	116.41 (16)
C8—N1—N2—C7	−179.62 (14)	N2—N1—C8—C9	1.4 (2)
C6—C1—C2—C3	−0.2 (3)	O1—C8—C9—C10	2.1 (2)
C1—C2—C3—C4	0.0 (3)	N1—C8—C9—C10	−177.17 (14)
C2—C3—C4—C5	0.1 (3)	O1—C8—C9—S1	178.35 (13)
C3—C4—C5—F1	179.92 (17)	N1—C8—C9—S1	−0.9 (2)
C3—C4—C5—C6	0.1 (3)	C12—S1—C9—C10	0.39 (13)
F1—C5—C6—C1	179.91 (14)	C12—S1—C9—C8	−176.37 (14)
C4—C5—C6—C1	−0.2 (2)	C8—C9—C10—C11	176.15 (14)
F1—C5—C6—C7	−0.6 (2)	S1—C9—C10—C11	−0.62 (18)
C4—C5—C6—C7	179.24 (15)	C8—C9—C10—Cl1	−5.0 (2)
C2—C1—C6—C5	0.3 (2)	S1—C9—C10—Cl1	178.22 (10)
C2—C1—C6—C7	−179.19 (15)	C9—C10—C11—C12	0.6 (2)
N1—N2—C7—C6	−178.51 (13)	Cl1—C10—C11—C12	−178.35 (14)
C5—C6—C7—N2	−173.37 (14)	C10—C11—C12—S1	−0.3 (2)
C1—C6—C7—N2	6.1 (2)	C9—S1—C12—C11	−0.07 (17)
N2—N1—C8—O1	−177.85 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.12	2.9552 (18)	163
C7—H7A···O1i	0.93	2.41	3.2268 (19)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.12	2.9552 (18)	163
C7—H7A⋯O1i	0.93	2.41	3.2268 (19)	147

Symmetry code: (i) .