2-[(2-Chloro­benzyl­idene)amino]-4,5,6,7-tetra­hydro-1-benzothio­phene-3-carbonitrile

Asiri, A.M.; Khan, S.A.; Tahir, M.N.

doi:10.1107/S1600536811032302

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2355

doi:10.1107/S1600536811032302

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2-[(2-Chlorobenzylidene)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile

Abdullah M. Asiri,^a,^b Salman A. Khan ^b and M. Nawaz Tahir ^c ^*

^aThe Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah 21589, PO Box 80203, Saudi Arabia, ^bDepartment of Chemistry, Faculty of Science, King Abduaziz University, Jeddah 21589, PO Box 80203, Saudi Arabia, and ^cUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 24 July 2011; accepted 9 August 2011; online 17 August 2011)

In the title compound, C₁₆H₁₃ClN₂S, the mean planes fitted through all non-H atoms of the heterocyclic five-membered and the benzene rings are oriented at a dihedral angle of 5.19 (7)°. In the crystal, a weak C—H⋯π interaction occurs, along with weak π–π interactions [cenroid–centroid distance = 3.7698 (11) Å].

Related literature

For information on the use of Schiff bases in pharmaceutical chemistry, see: Lewinski et al. (2005 ). For related structures, see: Asiri et al. (2011a ,b ).

Experimental

Crystal data

C₁₆H₁₃ClN₂S
M_r = 300.79
Triclinic, $[P \overline 1]$
a = 8.3383 (4) Å
b = 8.6885 (4) Å
c = 10.5746 (5) Å
α = 85.975 (2)°
β = 80.806 (2)°
γ = 73.003 (2)°
V = 723.00 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 296 K
0.40 × 0.25 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.931, T_max = 0.951
10003 measured reflections
2600 independent reflections
2308 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.105
S = 1.03
2600 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯Cgⁱ	0.97	2.87	3.744 (3)	151
Symmetry code: (i) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811032302/nk2106sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032302/nk2106Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811032302/nk2106Isup3.cml

checkCIF report

Comment top

Schiff-base compounds have been used as intermediate for various reactions (Lewinski, et al., 2005) and medical substrates. The title compound (I), (Fig. 1) has been prepared as a Pharmaceutical intermediate.

We have reported the crystal structure of 2-[(benzo[1,3]dioxol-5-ylmethylene)-amino]-4,5,6,7-tetrahydro-benzo[b]thiophene -3-carbonitrile (Asiri et al., 2011a) and 2-[(4-Chloro-benzylidene)-amino]-4,5,6,7-tetrahydro-benzo[b]thiophene -3-carbonitrile (Asiri et al., 2011b) which are related to the title compound.

In (I), the five membered ring A (C1/C2/C3/C8/S1) of 2-amino-4,5,6,7- tetrahydro-1-benzothiophene-3-carbonitrile and the group B (C10–C16/CL1) of 2-chlorobenzaldehyde are planar with r. m. s. deviation of 0.0097 and 0.0020 Å, respectively. The dihedral angle between A/B is 5.19 (7)°. A C—H···π interaction between the six membered rings of 2-amino-4,5,6,7-tetrahydro-1- benzothiophene-3-carbonitrile and the 2-chlorobenzaldehyde group is present (Table 1). π–π interactions [separation: 3.7698 (11) Å] between the heterocyclic five membered and benzene rings are also present.

Related literature top

For information on the use of Schiff bases in pharmaceutical chemistry, see: Lewinski et al. (2005). For related structures, see: Asiri et al. (2011a,b).

Experimental top

A mixture of 2-chloro benzaldehyde (0.46 g, 2.4 mmol) and 2-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-carbonitrile (0.32 g, 3.3 mmol) in ethanol (15 ml) was heated for 3 h. The progress of the reaction was monitored by TLC. The solid that separated from the cooled mixture was collected and recrystallized from a methanol-chloroform mixture (8:2) to give yellow needles of the title compound (I).

Yellow solid: Yield: 82%, m.p. 450 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The title compounds with displacement ellipsoids at the 50% probability level. H-atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that C—H···π interactions are present. Only the H-atom involved in π-interaction is present.

2-[(2-Chlorobenzylidene)amino]-4,5,6,7-tetrahydro-1-benzothiophene- 3-carbonitrile top

Crystal data top

C₁₆H₁₃ClN₂S	Z = 2
M_r = 300.79	F(000) = 312
Triclinic, P1	D_x = 1.382 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3383 (4) Å	Cell parameters from 2308 reflections
b = 8.6885 (4) Å	θ = 3.0–25.3°
c = 10.5746 (5) Å	µ = 0.40 mm⁻¹
α = 85.975 (2)°	T = 296 K
β = 80.806 (2)°	Rod, yellow
γ = 73.003 (2)°	0.40 × 0.25 × 0.25 mm
V = 723.00 (6) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	2600 independent reflections
Radiation source: fine-focus sealed tube	2308 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 8.20 pixels mm^-1	θ_max = 25.3°, θ_min = 3.0°
ω scans	h = −9→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
T_min = 0.931, T_max = 0.951	l = −12→12
10003 measured reflections

Refinement top

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0542P)² + 0.253P] where P = (F_o² + 2F_c²)/3
2600 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₆H₁₃ClN₂S	γ = 73.003 (2)°
M_r = 300.79	V = 723.00 (6) Å³
Triclinic, P1	Z = 2
a = 8.3383 (4) Å	Mo Kα radiation
b = 8.6885 (4) Å	µ = 0.40 mm⁻¹
c = 10.5746 (5) Å	T = 296 K
α = 85.975 (2)°	0.40 × 0.25 × 0.25 mm
β = 80.806 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2600 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2308 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.951	R_int = 0.019
10003 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
2600 reflections	Δρ_min = −0.34 e Å⁻³
181 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Cl1	0.51410 (9)	0.59840 (7)	−0.31788 (6)	0.0866 (2)
S1	0.05883 (6)	0.76273 (6)	0.05536 (4)	0.0534 (2)
N1	0.0435 (3)	0.2524 (2)	0.3132 (2)	0.0764 (7)
N2	0.24264 (18)	0.44103 (18)	0.02432 (13)	0.0474 (5)
C1	0.1187 (2)	0.5590 (2)	0.09452 (16)	0.0444 (5)
C2	0.0275 (2)	0.53040 (19)	0.20896 (15)	0.0409 (5)
C3	−0.0859 (2)	0.67215 (19)	0.26797 (15)	0.0402 (5)
C4	−0.1898 (2)	0.6775 (2)	0.39739 (16)	0.0481 (6)
C5	−0.3072 (3)	0.8451 (2)	0.42743 (19)	0.0596 (6)
C6	−0.2276 (3)	0.9751 (2)	0.3795 (2)	0.0639 (7)
C7	−0.1776 (3)	0.9748 (2)	0.23394 (18)	0.0563 (6)
C8	−0.0812 (2)	0.8060 (2)	0.19563 (16)	0.0450 (5)
C9	0.0415 (2)	0.3740 (2)	0.26452 (17)	0.0490 (6)
C10	0.3285 (2)	0.4785 (2)	−0.07655 (17)	0.0515 (6)
C11	0.4641 (2)	0.3591 (2)	−0.15131 (16)	0.0467 (5)
C12	0.5574 (2)	0.4006 (2)	−0.26298 (18)	0.0505 (6)
C13	0.6858 (2)	0.2868 (3)	−0.33329 (18)	0.0553 (6)
C14	0.7236 (2)	0.1295 (3)	−0.29270 (19)	0.0581 (6)
C15	0.6354 (3)	0.0838 (3)	−0.1829 (2)	0.0631 (7)
C16	0.5064 (3)	0.1976 (2)	−0.11318 (19)	0.0580 (6)
H4A	−0.11493	0.64359	0.46182	0.0577*
H4B	−0.25684	0.60246	0.40122	0.0577*
H5A	−0.40913	0.86058	0.38900	0.0715*
H5B	−0.34027	0.85337	0.51947	0.0715*
H6A	−0.12747	0.96148	0.41971	0.0766*
H6B	−0.30654	1.07855	0.40410	0.0766*
H7A	−0.27819	1.01182	0.19234	0.0676*
H7B	−0.10754	1.04641	0.20812	0.0676*
H10	0.30434	0.58581	−0.10391	0.0618*
H13	0.74600	0.31718	−0.40782	0.0664*
H14	0.80998	0.05264	−0.33990	0.0697*
H15	0.66233	−0.02358	−0.15544	0.0757*
H16	0.44656	0.16560	−0.03915	0.0696*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0933 (4)	0.0609 (3)	0.0809 (4)	−0.0090 (3)	0.0284 (3)	0.0135 (3)
S1	0.0620 (3)	0.0531 (3)	0.0391 (3)	−0.0172 (2)	0.0119 (2)	−0.0022 (2)
N1	0.0988 (15)	0.0503 (10)	0.0746 (12)	−0.0181 (10)	−0.0035 (11)	0.0008 (9)
N2	0.0421 (8)	0.0579 (9)	0.0393 (8)	−0.0130 (7)	0.0043 (6)	−0.0117 (6)
C1	0.0419 (9)	0.0528 (10)	0.0373 (8)	−0.0138 (7)	0.0020 (7)	−0.0100 (7)
C2	0.0393 (8)	0.0441 (9)	0.0375 (8)	−0.0108 (7)	−0.0007 (7)	−0.0052 (7)
C3	0.0376 (8)	0.0446 (9)	0.0365 (8)	−0.0113 (7)	0.0013 (6)	−0.0051 (7)
C4	0.0494 (10)	0.0483 (10)	0.0400 (9)	−0.0107 (8)	0.0082 (7)	−0.0042 (7)
C5	0.0584 (11)	0.0571 (11)	0.0507 (11)	−0.0076 (9)	0.0146 (9)	−0.0069 (9)
C6	0.0718 (13)	0.0486 (10)	0.0587 (12)	−0.0092 (9)	0.0165 (10)	−0.0123 (9)
C7	0.0635 (12)	0.0425 (10)	0.0542 (11)	−0.0095 (8)	0.0064 (9)	−0.0009 (8)
C8	0.0466 (9)	0.0467 (9)	0.0384 (8)	−0.0130 (7)	0.0044 (7)	−0.0044 (7)
C9	0.0521 (10)	0.0460 (10)	0.0447 (9)	−0.0099 (8)	0.0009 (8)	−0.0091 (8)
C10	0.0462 (10)	0.0592 (11)	0.0445 (10)	−0.0129 (8)	0.0065 (8)	−0.0092 (8)
C11	0.0413 (9)	0.0547 (10)	0.0413 (9)	−0.0130 (8)	0.0040 (7)	−0.0077 (7)
C12	0.0461 (10)	0.0547 (10)	0.0462 (10)	−0.0130 (8)	0.0041 (8)	−0.0027 (8)
C13	0.0453 (10)	0.0701 (12)	0.0447 (10)	−0.0151 (9)	0.0099 (8)	−0.0062 (9)
C14	0.0477 (10)	0.0625 (12)	0.0548 (11)	−0.0054 (9)	0.0064 (8)	−0.0156 (9)
C15	0.0634 (12)	0.0543 (11)	0.0604 (12)	−0.0074 (9)	0.0070 (10)	−0.0042 (9)
C16	0.0578 (11)	0.0596 (12)	0.0486 (10)	−0.0146 (9)	0.0120 (9)	−0.0018 (9)

Geometric parameters (Å, º) top

Cl1—C12	1.7277 (18)	C12—C13	1.381 (3)
S1—C1	1.7322 (17)	C13—C14	1.364 (3)
S1—C8	1.7243 (18)	C14—C15	1.371 (3)
N1—C9	1.139 (2)	C15—C16	1.380 (3)
N2—C1	1.383 (2)	C4—H4A	0.9700
N2—C10	1.265 (2)	C4—H4B	0.9700
C1—C2	1.371 (2)	C5—H5A	0.9700
C2—C3	1.428 (2)	C5—H5B	0.9700
C2—C9	1.422 (2)	C6—H6A	0.9700
C3—C4	1.494 (2)	C6—H6B	0.9700
C3—C8	1.353 (2)	C7—H7A	0.9700
C4—C5	1.521 (2)	C7—H7B	0.9700
C5—C6	1.491 (3)	C10—H10	0.9300
C6—C7	1.529 (3)	C13—H13	0.9300
C7—C8	1.500 (2)	C14—H14	0.9300
C10—C11	1.457 (2)	C15—H15	0.9300
C11—C12	1.393 (3)	C16—H16	0.9300
C11—C16	1.390 (2)

C1—S1—C8	92.06 (8)	C3—C4—H4A	109.00
C1—N2—C10	120.23 (15)	C3—C4—H4B	109.00
S1—C1—N2	126.07 (13)	C5—C4—H4A	109.00
S1—C1—C2	109.88 (12)	C5—C4—H4B	109.00
N2—C1—C2	124.04 (15)	H4A—C4—H4B	108.00
C1—C2—C3	114.07 (14)	C4—C5—H5A	109.00
C1—C2—C9	123.61 (15)	C4—C5—H5B	109.00
C3—C2—C9	122.32 (15)	C6—C5—H5A	109.00
C2—C3—C4	125.31 (14)	C6—C5—H5B	109.00
C2—C3—C8	111.71 (15)	H5A—C5—H5B	108.00
C4—C3—C8	122.86 (15)	C5—C6—H6A	109.00
C3—C4—C5	112.01 (14)	C5—C6—H6B	109.00
C4—C5—C6	112.83 (19)	C7—C6—H6A	109.00
C5—C6—C7	112.49 (17)	C7—C6—H6B	109.00
C6—C7—C8	108.21 (14)	H6A—C6—H6B	108.00
S1—C8—C3	112.24 (13)	C6—C7—H7A	110.00
S1—C8—C7	122.74 (13)	C6—C7—H7B	110.00
C3—C8—C7	124.94 (16)	C8—C7—H7A	110.00
N1—C9—C2	175.9 (2)	C8—C7—H7B	110.00
N2—C10—C11	122.19 (16)	H7A—C7—H7B	108.00
C10—C11—C12	122.04 (15)	N2—C10—H10	119.00
C10—C11—C16	120.95 (16)	C11—C10—H10	119.00
C12—C11—C16	117.01 (16)	C12—C13—H13	120.00
Cl1—C12—C11	120.35 (13)	C14—C13—H13	120.00
Cl1—C12—C13	117.94 (15)	C13—C14—H14	120.00
C11—C12—C13	121.71 (17)	C15—C14—H14	120.00
C12—C13—C14	119.53 (18)	C14—C15—H15	120.00
C13—C14—C15	120.6 (2)	C16—C15—H15	120.00
C14—C15—C16	119.8 (2)	C11—C16—H16	119.00
C11—C16—C15	121.36 (19)	C15—C16—H16	119.00

C8—S1—C1—N2	−176.35 (16)	C4—C3—C8—C7	−0.2 (3)
C8—S1—C1—C2	2.04 (14)	C3—C4—C5—C6	−38.3 (2)
C1—S1—C8—C7	175.39 (17)	C4—C5—C6—C7	60.9 (2)
C1—S1—C8—C3	−1.37 (15)	C5—C6—C7—C8	−48.8 (3)
C10—N2—C1—C2	−175.64 (17)	C6—C7—C8—S1	−156.62 (16)
C1—N2—C10—C11	177.94 (16)	C6—C7—C8—C3	19.7 (3)
C10—N2—C1—S1	2.5 (3)	N2—C10—C11—C12	179.42 (17)
S1—C1—C2—C3	−2.3 (2)	N2—C10—C11—C16	−0.9 (3)
S1—C1—C2—C9	176.99 (14)	C10—C11—C12—Cl1	−0.3 (2)
N2—C1—C2—C3	176.19 (16)	C10—C11—C12—C13	179.96 (17)
N2—C1—C2—C9	−4.6 (3)	C16—C11—C12—Cl1	−179.97 (15)
C9—C2—C3—C8	−177.98 (16)	C16—C11—C12—C13	0.3 (3)
C9—C2—C3—C4	5.9 (3)	C10—C11—C16—C15	−179.6 (2)
C1—C2—C3—C4	−174.81 (16)	C12—C11—C16—C15	0.1 (3)
C1—C2—C3—C8	1.3 (2)	Cl1—C12—C13—C14	179.92 (15)
C2—C3—C4—C5	−175.60 (17)	C11—C12—C13—C14	−0.3 (3)
C8—C3—C4—C5	8.7 (2)	C12—C13—C14—C15	−0.1 (3)
C2—C3—C8—S1	0.3 (2)	C13—C14—C15—C16	0.5 (3)
C2—C3—C8—C7	−176.34 (18)	C14—C15—C16—C11	−0.5 (4)
C4—C3—C8—S1	176.53 (13)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cgⁱ	0.97	2.87	3.744 (3)	151

Symmetry code: (i) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃ClN₂S
M_r	300.79
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.3383 (4), 8.6885 (4), 10.5746 (5)
α, β, γ (°)	85.975 (2), 80.806 (2), 73.003 (2)
V (Å³)	723.00 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.40 × 0.25 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.931, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	10003, 2600, 2308
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.105, 1.03
No. of reflections	2600
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.34

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cgⁱ	0.97	2.87	3.744 (3)	151

Symmetry code: (i) −x, −y+1, −z.

Acknowledgements

The authors would like to thank the Chemistry Department, King Abdul Aziz University, Jeddah, Saudi Arabia, for providing research facilities and for the financial support of this work via grant No. 3–045/430.

References

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Volume 67| Part 9| September 2011| Page o2355

doi:10.1107/S1600536811032302

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

2-[(2-Chloro­benzyl­­idene)amino]-4,5,6,7-tetra­hydro-1-benzo­thio­phene-3-carbo­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[(2-Chlorobenzylidene)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile