N'-[(1E)-(4-Fluoro-phen-yl)methyl-idene]thio-phene-2-carbohydrazide.

In the title compound, C(12)H(9)FN(2)OS, the thienyl ring is disordered over two positions, with the S atom of the major component [occupancy = 87.08 (16)°] oriented towards the ortho-H atom of the benzene ring. The mol-ecule is nearly planar, the dihedral angle between the thio-phene and benzene rings being 13.0 (2)° in the major 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, forming inversion dimers.

Related literature

For the 4-chloro and 4-bromo derivatives, see: Jiang (2010a ▶,b ▶).

Experimental

Crystal data

C12H9FN2OS

M = 248.27

Monoclinic,

a = 13.3076 (11) Å

b = 5.6015 (4) Å

c = 15.3062 (12) Å

β = 104.166 (9)°

V = 1106.27 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 100 K

0.35 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.906, T max = 0.986

4609 measured reflections

2532 independent reflections

1917 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.108

S = 1.06

2532 reflections

171 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 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/S1600536811056121/xu5417sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811056121/xu5417Isup2.hkl

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

C12H9FN2OS	F(000) = 512
Mr = 248.27	Dx = 1.491 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1715 reflections
a = 13.3076 (11) Å	θ = 2.7–27.5°
b = 5.6015 (4) Å	µ = 0.29 mm−1
c = 15.3062 (12) Å	T = 100 K
β = 104.166 (9)°	Prism, colorless
V = 1106.27 (15) Å3	0.35 × 0.15 × 0.05 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	2532 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1917 reflections with I > 2σ(I)
Mirror	Rint = 0.037
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.7°
ω scan	h = −13→17
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −7→4
Tmin = 0.906, Tmax = 0.986	l = −19→11
4609 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0425P)2 + 0.113P] where P = (Fo2 + 2Fc2)/3
2532 reflections	(Δ/σ)max = 0.001
171 parameters	Δρmax = 0.30 e Å−3
5 restraints	Δρmin = −0.28 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.72252 (5)	0.67192 (12)	0.49050 (4)	0.01785 (19)	0.8708 (16)
S1'	0.5631 (6)	0.5848 (19)	0.3160 (5)	0.0218 (7)	0.1292 (16)
F1	1.06801 (9)	0.4889 (2)	0.93514 (8)	0.0291 (3)
O1	0.49118 (10)	0.2092 (2)	0.40405 (9)	0.0203 (3)
N1	0.60280 (12)	0.2114 (3)	0.54014 (11)	0.0181 (4)
N2	0.68783 (12)	0.3050 (3)	0.59944 (11)	0.0164 (4)
C1	0.7215 (3)	0.8617 (10)	0.4025 (4)	0.0181 (7)	0.8708 (16)
H1A	0.7675	0.9928	0.4055	0.022*	0.8708 (16)
C2	0.6467 (8)	0.8018 (16)	0.3276 (5)	0.0203 (9)	0.8708 (16)
H2	0.6347	0.8863	0.2722	0.024*	0.8708 (16)
C3	0.5900 (3)	0.6034 (9)	0.3415 (3)	0.0218 (7)	0.8708 (16)
H3	0.5354	0.5381	0.2958	0.026*	0.8708 (16)
C1'	0.642 (6)	0.827 (12)	0.318 (4)	0.0203 (9)	0.13
H1'	0.6442	0.9298	0.2691	0.024*	0.1292 (16)
C2'	0.702 (3)	0.842 (8)	0.404 (3)	0.0181 (7)	0.13
H2'	0.7500	0.9690	0.4205	0.022*	0.1292 (16)
C3'	0.6923 (14)	0.671 (3)	0.4673 (13)	0.01785 (19)	0.13
H3'	0.7302	0.6679	0.5286	0.021*	0.1292 (16)
C4	0.61940 (14)	0.5099 (3)	0.42645 (12)	0.0166 (4)
C5	0.56736 (14)	0.3024 (3)	0.45575 (13)	0.0165 (4)
C6	0.71912 (15)	0.1929 (3)	0.67428 (13)	0.0169 (4)
H6	0.6836	0.0534	0.6854	0.020*
C7	0.80912 (14)	0.2777 (3)	0.74281 (12)	0.0162 (4)
C8	0.84780 (15)	0.1384 (3)	0.81905 (13)	0.0188 (4)
H8	0.8139	−0.0068	0.8264	0.023*
C9	0.93487 (16)	0.2074 (3)	0.88442 (13)	0.0227 (5)
H9	0.9613	0.1112	0.9360	0.027*
C10	0.98170 (15)	0.4193 (4)	0.87216 (13)	0.0199 (4)
C11	0.94486 (15)	0.5653 (3)	0.79870 (13)	0.0181 (4)
H11	0.9783	0.7121	0.7926	0.022*
C12	0.85802 (14)	0.4930 (3)	0.73393 (12)	0.0166 (4)
H12	0.8316	0.5913	0.6829	0.020*
H1	0.5728 (17)	0.078 (4)	0.5544 (15)	0.035 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0196 (4)	0.0175 (3)	0.0169 (4)	−0.0051 (3)	0.0053 (2)	−0.0012 (2)
S1'	0.010 (2)	0.0290 (13)	0.025 (2)	−0.0022 (16)	0.0011 (14)	0.0011 (18)
F1	0.0230 (6)	0.0378 (7)	0.0222 (7)	−0.0021 (6)	−0.0027 (5)	−0.0023 (6)
O1	0.0173 (7)	0.0236 (7)	0.0197 (7)	−0.0040 (6)	0.0037 (6)	−0.0009 (6)
N1	0.0172 (8)	0.0194 (9)	0.0174 (9)	−0.0056 (7)	0.0035 (7)	−0.0015 (7)
N2	0.0146 (8)	0.0165 (8)	0.0185 (9)	−0.0005 (7)	0.0048 (7)	−0.0025 (6)
C1	0.015 (2)	0.0156 (15)	0.0255 (11)	−0.0038 (15)	0.0096 (15)	0.0012 (9)
C2	0.0175 (15)	0.022 (3)	0.023 (2)	0.004 (2)	0.0069 (15)	0.0076 (13)
C3	0.010 (2)	0.0290 (13)	0.025 (2)	−0.0022 (16)	0.0011 (14)	0.0011 (18)
C1'	0.0175 (15)	0.022 (3)	0.023 (2)	0.004 (2)	0.0069 (15)	0.0076 (13)
C2'	0.015 (2)	0.0156 (15)	0.0255 (11)	−0.0038 (15)	0.0096 (15)	0.0012 (9)
C3'	0.0196 (4)	0.0175 (3)	0.0169 (4)	−0.0051 (3)	0.0053 (2)	−0.0012 (2)
C4	0.0148 (9)	0.0168 (9)	0.0192 (10)	0.0011 (8)	0.0058 (8)	−0.0020 (8)
C5	0.0151 (9)	0.0186 (10)	0.0169 (10)	0.0012 (8)	0.0062 (8)	−0.0030 (8)
C6	0.0176 (10)	0.0153 (9)	0.0195 (10)	−0.0010 (8)	0.0077 (8)	0.0006 (8)
C7	0.0181 (10)	0.0168 (9)	0.0159 (9)	0.0017 (8)	0.0084 (8)	−0.0005 (7)
C8	0.0225 (10)	0.0151 (9)	0.0204 (10)	−0.0016 (8)	0.0082 (9)	0.0013 (8)
C9	0.0280 (11)	0.0218 (10)	0.0174 (10)	0.0058 (9)	0.0036 (9)	0.0040 (8)
C10	0.0161 (9)	0.0268 (11)	0.0162 (10)	0.0004 (9)	0.0030 (8)	−0.0043 (8)
C11	0.0200 (10)	0.0166 (10)	0.0195 (10)	−0.0013 (8)	0.0083 (9)	−0.0014 (8)
C12	0.0177 (10)	0.0177 (9)	0.0151 (9)	0.0034 (8)	0.0055 (8)	0.0013 (8)

S1—C1	1.714 (4)	C2'—C3'	1.389 (11)
S1—C4	1.7346 (19)	C2'—H2'	0.9500
S1'—C1'	1.713 (11)	C3'—C4	1.361 (10)
S1'—C4	1.725 (6)	C3'—H3'	0.9500
F1—C10	1.363 (2)	C4—C5	1.478 (3)
O1—C5	1.238 (2)	C6—C7	1.465 (3)
N1—C5	1.361 (2)	C6—H6	0.9500
N1—N2	1.370 (2)	C7—C12	1.392 (3)
N1—H1	0.90 (2)	C7—C8	1.394 (3)
N2—C6	1.283 (2)	C8—C9	1.388 (3)
C1—C2	1.363 (3)	C8—H8	0.9500
C1—H1A	0.9500	C9—C10	1.374 (3)
C2—C3	1.388 (5)	C9—H9	0.9500
C2—H2	0.9500	C10—C11	1.380 (3)
C3—C4	1.367 (4)	C11—C12	1.386 (3)
C3—H3	0.9500	C11—H11	0.9500
C1'—C2'	1.362 (10)	C12—H12	0.9500
C1'—H1'	0.9500
C1—S1—C4	91.55 (18)	C5—C4—S1'	111.4 (3)
C1'—S1'—C4	93.3 (15)	C3—C4—S1	109.9 (2)
C5—N1—N2	121.58 (17)	C5—C4—S1	127.20 (14)
C5—N1—H1	118.1 (14)	O1—C5—N1	119.21 (18)
N2—N1—H1	120.0 (14)	O1—C5—C4	120.57 (17)
C6—N2—N1	116.04 (16)	N1—C5—C4	120.22 (17)
C2—C1—S1	111.8 (3)	N2—C6—C7	120.68 (17)
C2—C1—H1A	124.1	N2—C6—H6	119.7
S1—C1—H1A	124.1	C7—C6—H6	119.7
C1—C2—C3	112.4 (4)	C12—C7—C8	118.76 (18)
C1—C2—H2	123.8	C12—C7—C6	122.06 (17)
C3—C2—H2	123.8	C8—C7—C6	119.18 (17)
C4—C3—C2	114.3 (3)	C9—C8—C7	121.31 (18)
C4—C3—H3	122.8	C9—C8—H8	119.3
C2—C3—H3	122.8	C7—C8—H8	119.3
C2'—C1'—S1'	106 (3)	C10—C9—C8	117.96 (18)
C2'—C1'—H1'	127.0	C10—C9—H9	121.0
S1'—C1'—H1'	127.0	C8—C9—H9	121.0
C1'—C2'—C3'	120 (4)	F1—C10—C9	118.83 (17)
C1'—C2'—H2'	120.0	F1—C10—C11	118.46 (17)
C3'—C2'—H2'	120.0	C9—C10—C11	122.72 (18)
C4—C3'—C2'	108 (2)	C10—C11—C12	118.51 (18)
C4—C3'—H3'	125.9	C10—C11—H11	120.7
C2'—C3'—H3'	125.9	C12—C11—H11	120.7
C3'—C4—C5	135.8 (9)	C11—C12—C7	120.73 (17)
C3—C4—C5	122.9 (2)	C11—C12—H12	119.6
C3'—C4—S1'	112.3 (9)	C7—C12—H12	119.6
C5—N1—N2—C6	−174.53 (16)	N2—N1—C5—O1	178.84 (15)
C4—S1—C1—C2	−0.7 (8)	N2—N1—C5—C4	−1.2 (3)
S1—C1—C2—C3	0.2 (13)	C3'—C4—C5—O1	168.9 (14)
C1—C2—C3—C4	0.5 (13)	C3—C4—C5—O1	−2.7 (4)
C4—S1'—C1'—C2'	−3(7)	S1'—C4—C5—O1	−2.1 (4)
S1'—C1'—C2'—C3'	2(9)	S1—C4—C5—O1	176.76 (14)
C1'—C2'—C3'—C4	0(7)	C3'—C4—C5—N1	−11.1 (14)
C2'—C3'—C4—C3	−1(3)	C3—C4—C5—N1	177.3 (3)
C2'—C3'—C4—C5	−174 (2)	S1'—C4—C5—N1	177.9 (4)
C2'—C3'—C4—S1'	−3(3)	S1—C4—C5—N1	−3.2 (3)
C2'—C3'—C4—S1	149 (7)	N1—N2—C6—C7	−179.76 (15)
C2—C3—C4—C3'	4.5 (13)	N2—C6—C7—C12	6.3 (3)
C2—C3—C4—C5	178.5 (7)	N2—C6—C7—C8	−173.20 (17)
C2—C3—C4—S1'	176 (3)	C12—C7—C8—C9	−1.6 (3)
C2—C3—C4—S1	−1.0 (8)	C6—C7—C8—C9	177.91 (17)
C1'—S1'—C4—C3'	4(4)	C7—C8—C9—C10	0.5 (3)
C1'—S1'—C4—C3	−5(5)	C8—C9—C10—F1	−179.27 (16)
C1'—S1'—C4—C5	177 (4)	C8—C9—C10—C11	0.9 (3)
C1'—S1'—C4—S1	−2(4)	F1—C10—C11—C12	179.03 (15)
C1—S1—C4—C3'	−30 (5)	C9—C10—C11—C12	−1.1 (3)
C1—S1—C4—C3	1.0 (3)	C10—C11—C12—C7	0.0 (3)
C1—S1—C4—C5	−178.5 (3)	C8—C7—C12—C11	1.3 (3)
C1—S1—C4—S1'	0.3 (5)	C6—C7—C12—C11	−178.15 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.90 (2)	1.99 (3)	2.893 (2)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.90 (2)	1.99 (3)	2.893 (2)	176 (2)

Symmetry code: (i) .