5-{[(E)-2-(4-Iodo-phen-yl)hydrazinyl-idene]meth-yl}thio-phene-2-carbaldehyde.

The title compound, C(12)H(9)IN(2)OS, has an overall U-shape, with a dihedral angle of 21.4 (3)° between the thio-phene and benzene rings. In the crystal, supra-molecular chains mediated by N-H⋯O hydrogen bonds are formed along the b-axis direction.

Related literature

For background to 2-substituted thio­phenes, see: Campaigne (1984 ▶); Kleemann et al. (2006 ▶). For the anti­mycobacterial activity of 2-substituted thio­phenes, see: Lourenço et al. (2007 ▶). For a related structure, see: Ferreira et al. (2009 ▶). For background to the production of mono-hydrazones by the reaction of aryl­hydrazines with arenedicarbaldehydes, see: Reuch & Heflet (1956 ▶); Vaysse & Pastour (1964 ▶); Butler et al. (1990 ▶); Glidewell et al. (2005 ▶); Low et al. (2006 ▶); Wardell et al. (2006 ▶).

Experimental

Crystal data

C12H9IN2OS

M = 356.17

Orthorhombic,

a = 6.9291 (9) Å

b = 11.7602 (10) Å

c = 30.958 (4) Å

V = 2522.7 (5) Å3

Z = 8

Mo Kα radiation

μ = 2.69 mm−1

T = 120 K

0.16 × 0.08 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.616, T max = 0.746

15735 measured reflections

2614 independent reflections

1674 reflections with I > 2σ(I)

R int = 0.095

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.113

S = 1.04

2614 reflections

157 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.08 e Å−3

Δρmin = −0.60 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809055172/hb5284sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055172/hb5284Isup2.hkl

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

C12H9IN2OS	F(000) = 1376
Mr = 356.17	Dx = 1.876 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 16555 reflections
a = 6.9291 (9) Å	θ = 2.9–27.5°
b = 11.7602 (10) Å	µ = 2.69 mm−1
c = 30.958 (4) Å	T = 120 K
V = 2522.7 (5) Å3	Prism, colourless
Z = 8	0.16 × 0.08 × 0.05 mm

Nonius KappaCCD diffractometer	2614 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1674 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.095
Detector resolution: 9.091 pixels mm-1	θmax = 26.5°, θmin = 3.2°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −14→14
Tmin = 0.616, Tmax = 0.746	l = −38→37
15735 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0257P)2 + 17.1487P] where P = (Fo2 + 2Fc2)/3
2614 reflections	(Δ/σ)max = 0.001
157 parameters	Δρmax = 1.08 e Å−3
1 restraint	Δρmin = −0.60 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
I1	−0.01127 (8)	0.34335 (4)	0.487908 (18)	0.04277 (19)
S1	0.1013 (3)	0.10271 (14)	0.21597 (6)	0.0261 (4)
N1	0.0936 (8)	−0.0324 (5)	0.3466 (2)	0.0282 (14)
H1N	0.039 (9)	−0.099 (3)	0.350 (2)	0.034*
N2	0.1043 (8)	0.0033 (5)	0.3048 (2)	0.0266 (13)
O1	0.1012 (7)	0.2541 (4)	0.13359 (16)	0.0336 (12)
C1	0.0410 (10)	0.2143 (6)	0.4423 (2)	0.0323 (18)
C2	0.1194 (10)	0.2425 (6)	0.4030 (2)	0.0322 (18)
H2	0.1610	0.3182	0.3976	0.039*
C3	0.1374 (9)	0.1609 (6)	0.3714 (2)	0.0278 (16)
H3	0.1900	0.1808	0.3441	0.033*
C4	0.0794 (9)	0.0499 (6)	0.3792 (2)	0.0231 (15)
C5	0.0110 (10)	0.0198 (5)	0.4197 (2)	0.0284 (16)
H5	−0.0202	−0.0573	0.4257	0.034*
C6	−0.0121 (10)	0.1017 (6)	0.4514 (2)	0.0332 (17)
H6	−0.0631	0.0820	0.4789	0.040*
C7	0.0949 (10)	−0.0729 (6)	0.2752 (2)	0.0275 (17)
H7	0.0837	−0.1509	0.2827	0.033*
C8	0.1016 (9)	−0.0394 (5)	0.2306 (2)	0.0249 (16)
C9	0.1085 (9)	0.0672 (6)	0.1616 (2)	0.0239 (15)
C10	0.1118 (10)	−0.0491 (6)	0.1562 (2)	0.0291 (17)
H10	0.1177	−0.0849	0.1288	0.035*
C11	0.1057 (10)	−0.1090 (6)	0.1951 (2)	0.0292 (16)
H11	0.1046	−0.1897	0.1968	0.035*
C12	0.1088 (9)	0.1509 (6)	0.1282 (2)	0.0288 (16)
H12	0.1156	0.1243	0.0993	0.035*

	U11	U22	U33	U12	U13	U23
I1	0.0425 (3)	0.0365 (3)	0.0493 (3)	−0.0005 (3)	0.0024 (3)	−0.0128 (3)
S1	0.0228 (9)	0.0219 (8)	0.0336 (10)	−0.0006 (8)	0.0004 (8)	−0.0049 (8)
N1	0.023 (3)	0.020 (3)	0.042 (4)	−0.002 (3)	0.004 (3)	0.001 (3)
N2	0.020 (3)	0.030 (3)	0.030 (4)	0.001 (3)	0.005 (3)	0.003 (3)
O1	0.027 (3)	0.025 (3)	0.049 (3)	−0.003 (2)	−0.004 (3)	−0.001 (2)
C1	0.029 (4)	0.033 (4)	0.035 (4)	0.001 (3)	−0.007 (3)	−0.003 (3)
C2	0.025 (4)	0.027 (4)	0.045 (5)	−0.005 (3)	−0.005 (4)	−0.002 (3)
C3	0.018 (3)	0.026 (4)	0.039 (4)	−0.002 (3)	−0.002 (3)	−0.001 (3)
C4	0.018 (3)	0.024 (4)	0.027 (4)	0.001 (3)	−0.002 (3)	−0.001 (3)
C5	0.027 (4)	0.020 (3)	0.038 (4)	0.001 (3)	−0.003 (4)	0.003 (3)
C6	0.034 (4)	0.032 (4)	0.034 (4)	0.002 (4)	0.001 (4)	−0.001 (3)
C7	0.021 (4)	0.022 (4)	0.040 (5)	0.000 (3)	0.000 (4)	0.001 (3)
C8	0.017 (3)	0.018 (3)	0.039 (4)	−0.002 (3)	0.001 (3)	−0.005 (3)
C9	0.012 (3)	0.031 (4)	0.029 (4)	0.002 (3)	0.001 (3)	−0.006 (3)
C10	0.023 (4)	0.025 (4)	0.039 (5)	0.001 (3)	−0.002 (3)	−0.011 (3)
C11	0.026 (4)	0.018 (3)	0.044 (5)	0.000 (3)	0.010 (4)	−0.006 (3)
C12	0.020 (3)	0.027 (4)	0.040 (5)	0.005 (4)	−0.002 (3)	−0.007 (3)

I1—C1	2.103 (7)	C4—C5	1.387 (9)
S1—C8	1.732 (7)	C5—C6	1.386 (9)
S1—C9	1.734 (7)	C5—H5	0.9500
N1—N2	1.362 (8)	C6—H6	0.9500
N1—C4	1.402 (8)	C7—C8	1.436 (9)
N1—H1N	0.876 (10)	C7—H7	0.9500
N2—C7	1.284 (8)	C8—C11	1.371 (9)
O1—C12	1.227 (8)	C9—C10	1.378 (9)
C1—C2	1.374 (10)	C9—C12	1.429 (9)
C1—C6	1.403 (10)	C10—C11	1.395 (10)
C2—C3	1.376 (9)	C10—H10	0.9500
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.388 (9)	C12—H12	0.9500
C3—H3	0.9500
C8—S1—C9	91.2 (3)	C5—C6—H6	120.5
N2—N1—C4	118.3 (6)	C1—C6—H6	120.5
N2—N1—H1N	114 (5)	N2—C7—C8	119.6 (6)
C4—N1—H1N	120 (5)	N2—C7—H7	120.2
C7—N2—N1	117.4 (6)	C8—C7—H7	120.2
C2—C1—C6	120.6 (7)	C11—C8—C7	127.4 (6)
C2—C1—I1	119.2 (5)	C11—C8—S1	111.5 (5)
C6—C1—I1	120.1 (5)	C7—C8—S1	121.1 (5)
C1—C2—C3	119.8 (7)	C10—C9—C12	126.6 (6)
C1—C2—H2	120.1	C10—C9—S1	110.9 (5)
C3—C2—H2	120.1	C12—C9—S1	122.5 (5)
C2—C3—C4	120.5 (7)	C9—C10—C11	113.3 (6)
C2—C3—H3	119.8	C9—C10—H10	123.3
C4—C3—H3	119.8	C11—C10—H10	123.3
C3—C4—C5	119.7 (6)	C8—C11—C10	113.0 (6)
C3—C4—N1	120.4 (6)	C8—C11—H11	123.5
C5—C4—N1	119.9 (6)	C10—C11—H11	123.5
C6—C5—C4	120.2 (6)	O1—C12—C9	125.7 (7)
C6—C5—H5	119.9	O1—C12—H12	117.2
C4—C5—H5	119.9	C9—C12—H12	117.2
C5—C6—C1	118.9 (7)
C4—N1—N2—C7	−172.2 (6)	N2—C7—C8—C11	175.5 (7)
C6—C1—C2—C3	3.2 (11)	N2—C7—C8—S1	−5.6 (9)
I1—C1—C2—C3	−173.9 (5)	C9—S1—C8—C11	−0.4 (5)
C1—C2—C3—C4	−0.9 (10)	C9—S1—C8—C7	−179.4 (6)
C2—C3—C4—C5	−3.0 (10)	C8—S1—C9—C10	−0.3 (5)
C2—C3—C4—N1	178.4 (6)	C8—S1—C9—C12	179.2 (6)
N2—N1—C4—C3	−20.8 (9)	C12—C9—C10—C11	−178.5 (6)
N2—N1—C4—C5	160.6 (6)	S1—C9—C10—C11	0.9 (8)
C3—C4—C5—C6	4.5 (10)	C7—C8—C11—C10	180.0 (7)
N1—C4—C5—C6	−176.9 (6)	S1—C8—C11—C10	1.0 (8)
C4—C5—C6—C1	−2.1 (11)	C9—C10—C11—C8	−1.2 (9)
C2—C1—C6—C5	−1.7 (11)	C10—C9—C12—O1	178.2 (7)
I1—C1—C6—C5	175.4 (5)	S1—C9—C12—O1	−1.2 (10)
N1—N2—C7—C8	178.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1i	0.88 (4)	2.05 (5)	2.916 (8)	172 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O1i	0.88 (4)	2.05 (5)	2.916 (8)	172 (5)

Symmetry code: (i) .