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

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

doi:10.1107/S1600536811030704

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2254

doi:10.1107/S1600536811030704

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2-[(4-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 23 July 2011; accepted 30 July 2011; online 6 August 2011)

In the title compound, C₁₆H₁₃ClN₂S, the dihedral angle between the 4-chlorobenzaldehyde moiety and the heterocyclic five-membered ring is 7.21 (17)°. In the crystal, molecules are linked by weak C—H⋯π interactions, generating [100] chains.

Related literature

For a related structure, see: Asiri et al. (2011 ).

Experimental

Crystal data

C₁₆H₁₃ClN₂S
M_r = 300.79
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.7815 (3) Å
b = 16.5670 (13) Å
c = 18.1658 (14) Å
V = 1439.01 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 296 K
0.35 × 0.15 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.931, T_max = 0.951
11075 measured reflections
2607 independent reflections
1821 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.099
S = 1.02
2607 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ), 1053 Friedel pairs
Flack parameter: 0.03 (10)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C8–C11/S1 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Cgⁱ	0.97	2.99	3.841 (6)	147
Symmetry code: (i) x+1, y, 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/S1600536811030704/hb6331sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811030704/hb6331Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811030704/hb6331Isup3.cml

checkCIF report

Comment top

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., 2011) which is related to the title compound, (I), Fig. 1.

In (I), the group A (C1–C7/CL1) of 4-chlorobenzaldehyde and the five membered ring B (C8—C11/S1) of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3- carbonitrile group are almost planar with r. m. s. deviation of 0.0150 and 0.0110 Å, respectively. The dihedral angle between A/B is 7.21 (17)°. A C—H···π interaction (Table 1) occurs in the crystal.

Related literature top

For a related structure, see: Asiri et al. (2011).

Experimental top

A mixture of 4-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). Yield: 82%, m.p. 504–505 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. View of (I) showing 50% displacement ellipsoids.

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

Crystal data top

C₁₆H₁₃ClN₂S	F(000) = 624
M_r = 300.79	D_x = 1.388 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1821 reflections
a = 4.7815 (3) Å	θ = 3.3–25.2°
b = 16.5670 (13) Å	µ = 0.40 mm⁻¹
c = 18.1658 (14) Å	T = 296 K
V = 1439.01 (18) Å³	Needle, yellow
Z = 4	0.35 × 0.15 × 0.12 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2607 independent reflections
Radiation source: fine-focus sealed tube	1821 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
Detector resolution: 8.20 pixels mm^-1	θ_max = 25.2°, θ_min = 3.3°
ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −19→17
T_min = 0.931, T_max = 0.951	l = −21→21
11075 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.0416P)² + 0.1311P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2607 reflections	Δρ_max = 0.26 e Å⁻³
181 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1053 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (10)

Crystal data top

C₁₆H₁₃ClN₂S	V = 1439.01 (18) Å³
M_r = 300.79	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.7815 (3) Å	µ = 0.40 mm⁻¹
b = 16.5670 (13) Å	T = 296 K
c = 18.1658 (14) Å	0.35 × 0.15 × 0.12 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2607 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1821 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.951	R_int = 0.055
11075 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.099	Δρ_max = 0.26 e Å⁻³
S = 1.02	Δρ_min = −0.19 e Å⁻³
2607 reflections	Absolute structure: Flack (1983), 1053 Friedel pairs
181 parameters	Absolute structure parameter: 0.03 (10)
0 restraints

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	−0.7805 (2)	−0.17259 (7)	−0.04726 (7)	0.0797 (4)
S1	0.4743 (2)	0.20961 (5)	0.08062 (4)	0.0506 (3)
N1	0.1842 (6)	0.06647 (16)	0.10865 (15)	0.0453 (10)
N2	0.4578 (9)	0.0048 (2)	0.28643 (17)	0.0787 (14)
C1	−0.1473 (7)	0.0110 (2)	0.02527 (17)	0.0406 (11)
C2	−0.2345 (8)	−0.0493 (2)	0.07260 (19)	0.0503 (12)
C3	−0.4313 (7)	−0.1048 (2)	0.0506 (2)	0.0547 (12)
C4	−0.5384 (7)	−0.1013 (2)	−0.01982 (19)	0.0513 (12)
C5	−0.4597 (8)	−0.0416 (2)	−0.06685 (19)	0.0560 (12)
C6	−0.2640 (7)	0.0135 (2)	−0.04455 (18)	0.0510 (12)
C7	0.0619 (7)	0.06949 (19)	0.04718 (19)	0.0445 (11)
C8	0.3759 (7)	0.1241 (2)	0.12951 (18)	0.0443 (12)
C9	0.5135 (8)	0.12209 (18)	0.19578 (15)	0.0393 (10)
C10	0.6876 (6)	0.19068 (19)	0.20924 (17)	0.0403 (11)
C11	0.6880 (7)	0.24227 (19)	0.15209 (17)	0.0417 (12)
C12	0.8316 (8)	0.3222 (2)	0.15026 (19)	0.0540 (12)
C13	1.0043 (12)	0.3330 (3)	0.2182 (3)	0.0947 (19)
C14	0.9144 (12)	0.2949 (3)	0.2830 (2)	0.103 (2)
C15	0.8375 (7)	0.2073 (2)	0.27953 (18)	0.0527 (12)
C16	0.4818 (9)	0.0573 (2)	0.24609 (17)	0.0484 (11)
H2	−0.15934	−0.05237	0.11974	0.0602*
H3	−0.49192	−0.14449	0.08309	0.0652*
H5	−0.53781	−0.03830	−0.11363	0.0670*
H6	−0.20794	0.05376	−0.07708	0.0609*
H7	0.10771	0.11083	0.01472	0.0534*
H12A	0.69350	0.36500	0.14716	0.0649*
H12B	0.95053	0.32546	0.10711	0.0649*
H13A	1.19183	0.31404	0.20749	0.1138*
H13B	1.01751	0.39043	0.22811	0.1138*
H14A	0.75291	0.32421	0.30118	0.1240*
H14B	1.06135	0.30081	0.31940	0.1240*
H15A	1.00517	0.17449	0.28231	0.0631*
H15B	0.71853	0.19360	0.32092	0.0631*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0610 (7)	0.0690 (7)	0.1092 (9)	−0.0156 (6)	−0.0022 (6)	−0.0261 (6)
S1	0.0612 (6)	0.0437 (5)	0.0469 (4)	−0.0018 (5)	−0.0048 (5)	0.0056 (4)
N1	0.0506 (18)	0.0409 (18)	0.0444 (16)	0.0006 (16)	−0.0036 (14)	−0.0047 (13)
N2	0.105 (3)	0.069 (2)	0.062 (2)	−0.014 (2)	−0.007 (2)	0.0196 (19)
C1	0.0409 (19)	0.036 (2)	0.045 (2)	0.0070 (17)	0.0009 (15)	−0.0040 (16)
C2	0.057 (2)	0.046 (2)	0.048 (2)	0.0009 (19)	−0.0022 (19)	−0.0042 (18)
C3	0.058 (2)	0.044 (2)	0.062 (2)	0.005 (2)	0.011 (2)	0.0012 (19)
C4	0.040 (2)	0.046 (2)	0.068 (2)	0.002 (2)	0.001 (2)	−0.0177 (19)
C5	0.054 (2)	0.060 (2)	0.054 (2)	−0.004 (2)	−0.009 (2)	−0.0066 (19)
C6	0.056 (2)	0.048 (2)	0.049 (2)	−0.001 (2)	0.001 (2)	0.0010 (18)
C7	0.050 (2)	0.038 (2)	0.0454 (18)	−0.0005 (18)	0.0050 (19)	0.0018 (16)
C8	0.046 (2)	0.040 (2)	0.047 (2)	0.0011 (18)	0.0043 (16)	−0.0030 (16)
C9	0.0423 (19)	0.0362 (18)	0.0394 (17)	0.0020 (18)	0.0040 (17)	0.0007 (14)
C10	0.0350 (18)	0.040 (2)	0.0459 (19)	0.0040 (18)	0.0049 (15)	−0.0024 (17)
C11	0.040 (2)	0.036 (2)	0.049 (2)	0.0008 (17)	0.0045 (16)	−0.0023 (17)
C12	0.056 (2)	0.042 (2)	0.064 (2)	−0.001 (2)	0.0060 (19)	0.0011 (18)
C13	0.112 (4)	0.070 (3)	0.102 (3)	−0.044 (3)	−0.038 (4)	0.007 (3)
C14	0.154 (5)	0.092 (4)	0.064 (3)	−0.063 (4)	−0.007 (3)	−0.012 (3)
C15	0.051 (2)	0.056 (2)	0.051 (2)	−0.005 (2)	−0.0019 (17)	−0.0042 (19)
C16	0.055 (2)	0.050 (2)	0.0403 (18)	−0.005 (2)	−0.0030 (19)	−0.0001 (17)

Geometric parameters (Å, º) top

Cl1—C4	1.727 (4)	C11—C12	1.492 (5)
S1—C8	1.737 (3)	C12—C13	1.496 (7)
S1—C11	1.739 (3)	C13—C14	1.403 (7)
N1—C7	1.262 (4)	C14—C15	1.499 (6)
N1—C8	1.377 (4)	C2—H2	0.9300
N2—C16	1.143 (5)	C3—H3	0.9300
C1—C2	1.382 (5)	C5—H5	0.9300
C1—C6	1.386 (5)	C6—H6	0.9300
C1—C7	1.448 (5)	C7—H7	0.9300
C2—C3	1.375 (5)	C12—H12A	0.9700
C3—C4	1.379 (5)	C12—H12B	0.9700
C4—C5	1.360 (5)	C13—H13A	0.9700
C5—C6	1.369 (5)	C13—H13B	0.9700
C8—C9	1.372 (4)	C14—H14A	0.9700
C9—C10	1.430 (4)	C14—H14B	0.9700
C9—C16	1.418 (4)	C15—H15A	0.9700
C10—C11	1.345 (4)	C15—H15B	0.9700
C10—C15	1.490 (4)

C8—S1—C11	91.79 (15)	C1—C2—H2	120.00
C7—N1—C8	121.7 (3)	C3—C2—H2	120.00
C2—C1—C6	118.0 (3)	C2—C3—H3	120.00
C2—C1—C7	121.4 (3)	C4—C3—H3	120.00
C6—C1—C7	120.6 (3)	C4—C5—H5	120.00
C1—C2—C3	120.6 (3)	C6—C5—H5	120.00
C2—C3—C4	119.7 (3)	C1—C6—H6	119.00
Cl1—C4—C3	119.2 (3)	C5—C6—H6	119.00
Cl1—C4—C5	120.1 (3)	N1—C7—H7	119.00
C3—C4—C5	120.7 (3)	C1—C7—H7	119.00
C4—C5—C6	119.2 (3)	C11—C12—H12A	110.00
C1—C6—C5	121.7 (3)	C11—C12—H12B	110.00
N1—C7—C1	122.5 (3)	C13—C12—H12A	110.00
S1—C8—N1	127.3 (2)	C13—C12—H12B	110.00
S1—C8—C9	109.8 (2)	H12A—C12—H12B	108.00
N1—C8—C9	123.0 (3)	C12—C13—H13A	108.00
C8—C9—C10	114.2 (3)	C12—C13—H13B	108.00
C8—C9—C16	122.2 (3)	C14—C13—H13A	108.00
C10—C9—C16	123.6 (3)	C14—C13—H13B	108.00
C9—C10—C11	112.0 (3)	H13A—C13—H13B	107.00
C9—C10—C15	125.0 (3)	C13—C14—H14A	108.00
C11—C10—C15	122.9 (3)	C13—C14—H14B	108.00
S1—C11—C10	112.2 (2)	C15—C14—H14A	108.00
S1—C11—C12	122.0 (2)	C15—C14—H14B	108.00
C10—C11—C12	125.6 (3)	H14A—C14—H14B	107.00
C11—C12—C13	110.0 (3)	C10—C15—H15A	110.00
C12—C13—C14	118.0 (5)	C10—C15—H15B	110.00
C13—C14—C15	118.4 (4)	C14—C15—H15A	110.00
C10—C15—C14	109.5 (3)	C14—C15—H15B	110.00
N2—C16—C9	179.5 (4)	H15A—C15—H15B	108.00

C11—S1—C8—N1	176.1 (3)	S1—C8—C9—C10	2.8 (4)
C11—S1—C8—C9	−2.1 (3)	S1—C8—C9—C16	−177.6 (3)
C8—S1—C11—C10	0.8 (3)	N1—C8—C9—C10	−175.4 (3)
C8—S1—C11—C12	−174.3 (3)	N1—C8—C9—C16	4.2 (5)
C8—N1—C7—C1	−177.9 (3)	C8—C9—C10—C11	−2.3 (4)
C7—N1—C8—S1	2.5 (5)	C8—C9—C10—C15	173.8 (3)
C7—N1—C8—C9	−179.6 (3)	C16—C9—C10—C11	178.1 (3)
C6—C1—C2—C3	−0.1 (5)	C16—C9—C10—C15	−5.8 (5)
C7—C1—C2—C3	−179.3 (3)	C9—C10—C11—S1	0.6 (4)
C2—C1—C6—C5	0.0 (5)	C9—C10—C11—C12	175.6 (3)
C7—C1—C6—C5	179.3 (3)	C15—C10—C11—S1	−175.6 (2)
C2—C1—C7—N1	3.4 (5)	C15—C10—C11—C12	−0.6 (5)
C6—C1—C7—N1	−175.9 (3)	C9—C10—C15—C14	−160.7 (3)
C1—C2—C3—C4	1.4 (5)	C11—C10—C15—C14	15.0 (5)
C2—C3—C4—Cl1	178.8 (3)	S1—C11—C12—C13	−178.9 (3)
C2—C3—C4—C5	−2.6 (5)	C10—C11—C12—C13	6.6 (5)
Cl1—C4—C5—C6	−178.9 (3)	C11—C12—C13—C14	−29.9 (6)
C3—C4—C5—C6	2.5 (5)	C12—C13—C14—C15	49.0 (7)
C4—C5—C6—C1	−1.2 (5)	C13—C14—C15—C10	−38.8 (6)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C8–C11/S1 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cgⁱ	0.97	2.99	3.841 (6)	147

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃ClN₂S
M_r	300.79
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	4.7815 (3), 16.5670 (13), 18.1658 (14)
V (Å³)	1439.01 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.35 × 0.15 × 0.12

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	11075, 2607, 1821
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.099, 1.02
No. of reflections	2607
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.19
Absolute structure	Flack (1983), 1053 Friedel pairs
Absolute structure parameter	0.03 (10)

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 C8–C11/S1 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cgⁱ	0.97	2.99	3.841 (6)	147

Symmetry code: (i) x+1, y, z.

Acknowledgements

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

References

Asiri, A. M., Khan, S. A. & Tahir, M. N. (2011). Acta Cryst. E67, o2162. CrossRef IUCr Journals Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2254

doi:10.1107/S1600536811030704

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

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