N′-(4-Chloro­benzyl­idene)-2-[4-(methyl­sulfan­yl)phen­yl]acetohydrazide

Fun, H.-K.; Hemamalini, M.; Sumangala, V.; Prasad, D.J.; Poojary, B.

doi:10.1107/S1600536811039857

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2847

doi:10.1107/S1600536811039857

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N′-(4-Chlorobenzylidene)-2-[4-(methylsulfanyl)phenyl]acetohydrazide

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^a V. Sumangala,^b D. Jagadeesh Prasad ^b and Boja Poojary ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Mangalore University, Mangalagangothri 574 199, Mangalore, Karnataka, India
^*Correspondence e-mail: hkfun@usm.my

(Received 26 September 2011; accepted 28 September 2011; online 5 October 2011)

In the title compound, C₁₆H₁₅ClN₂OS, the hydrazine group is twisted slightly: the C—N—N—C torsion angle is 175.46 (13)°. The dihedral angle between the two terminal aromatic rings is 87.01 (8)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R₂²(8) loops. The dimers are further linked by weak C—H⋯π interactions.

Related literature

For further details of aroylhydrozones, see: Li & Qu (2011 ); Zhang (2011 ); Fan et al. (2010 ). Ajani et al. (2010 ); Avaji et al. (2009 ); Rasras et al. (2010 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₅ClN₂OS
M_r = 318.81
Monoclinic, P 2₁ /c
a = 17.0923 (13) Å
b = 9.6719 (7) Å
c = 9.5592 (7) Å
β = 92.399 (1)°
V = 1578.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 296 K
0.91 × 0.49 × 0.09 mm

Data collection

Bruker APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.728, T_max = 0.967
17083 measured reflections
4748 independent reflections
3306 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.122
S = 1.04
4748 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1ⁱ	0.95	2.03	2.9784 (17)	176
C14—H14A⋯Cg1ⁱⁱ	0.93	2.89	3.7627 (17)	156
C5—H5A⋯Cg2ⁱⁱⁱ	0.93	2.98	3.4638 (17)	114
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811039857/hb6422sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811039857/hb6422Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811039857/hb6422Isup3.cml

checkCIF report

Comment top

Large number of aroylhydrozones have been synthesized in the recent years (Li & Qu, 2011; Zhang, 2011; Fan et al., 2010) which can serve as intermediates in synthesizing biologically active compounds (Ajani et al., 2010; Avaji et al., 2009; Rasras et al., 2010).

The asymmetric unit of the title compound is shown in Fig. 1. The hydrazine group is twisted slightly, with C7-N1-N2-C8, N1-N2-C8-C9 and N2-N1-C7-C6 torsion angles of 175.46 (13)°, 5.6 (2)° and -177.96 (12)°, respectively. The dihedral angle between the two terminal (C1–C6/C10–C15) phenyl rings is 87.01 (8)°.

In the crystal structure, (Fig. 2), centrosymmetrically related molecules are linked into dimers via pairs of intermolecular N2—H1N2···O1 (Table 1) hydrogen bonds, generating R₂²(8) ring motifs (Bernstein et al., 1995). The crystal structure is further stabilized by C—H···π interactions involving the centroids of the C1–C6 (Cg1) and C10–C15 (Cg2) rings.

Related literature top

For further details of aroylhydrozones, see: Li & Qu (2011); Zhang (2011); Fan et al. (2010). Ajani et al. (2010); Avaji et al. (2009); Rasras et al. (2010). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

An equimolar mixture of 2-(4-methylsulfanylphenyl)acetohydrazide and 4-chlorobenzaldehyde was refluxed for four hours in the presence of few drops of acid catalyst and ethanol as solvent.The compound obtained was filtered, washed, dried and recrystalised from ethanol to yield colourless plates.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound (I). H atoms not involved in hydrogen bonding are omitted.

N'-(4-Chlorobenzylidene)-2-[4-(methylsulfanyl)phenyl]acetohydrazide top

Crystal data top

C₁₆H₁₅ClN₂OS	F(000) = 664
M_r = 318.81	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4828 reflections
a = 17.0923 (13) Å	θ = 3.0–29.5°
b = 9.6719 (7) Å	µ = 0.37 mm⁻¹
c = 9.5592 (7) Å	T = 296 K
β = 92.399 (1)°	Plate, colourless
V = 1578.9 (2) Å³	0.91 × 0.49 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD diffractometer	4748 independent reflections
Radiation source: fine-focus sealed tube	3306 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 30.3°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −24→24
T_min = 0.728, T_max = 0.967	k = −13→13
17083 measured reflections	l = −9→13

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0504P)² + 0.3224P] where P = (F_o² + 2F_c²)/3
4748 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₆H₁₅ClN₂OS	V = 1578.9 (2) Å³
M_r = 318.81	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.0923 (13) Å	µ = 0.37 mm⁻¹
b = 9.6719 (7) Å	T = 296 K
c = 9.5592 (7) Å	0.91 × 0.49 × 0.09 mm
β = 92.399 (1)°

Data collection top

Bruker APEXII DUO CCD diffractometer	4748 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3306 reflections with I > 2σ(I)
T_min = 0.728, T_max = 0.967	R_int = 0.025
17083 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.04	Δρ_max = 0.41 e Å⁻³
4748 reflections	Δρ_min = −0.41 e Å⁻³
191 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.89531 (3)	0.48335 (6)	0.00009 (6)	0.0873 (2)
S1	0.08573 (3)	0.40633 (6)	0.47773 (6)	0.07612 (17)
O1	0.42041 (6)	0.12422 (11)	0.50622 (11)	0.0523 (3)
N1	0.57757 (7)	0.23664 (12)	0.31358 (13)	0.0471 (3)
N2	0.52912 (7)	0.15328 (13)	0.38944 (14)	0.0509 (3)
H1N2	0.5458	0.0642	0.4186	0.061*
C1	0.68893 (8)	0.38659 (15)	0.15181 (15)	0.0457 (3)
H1A	0.6393	0.4255	0.1543	0.055*
C2	0.74751 (9)	0.45572 (16)	0.08466 (16)	0.0525 (3)
H2A	0.7375	0.5404	0.0414	0.063*
C3	0.82114 (8)	0.39671 (17)	0.08305 (17)	0.0534 (4)
C4	0.83721 (9)	0.27056 (18)	0.14429 (18)	0.0574 (4)
H4A	0.8869	0.2318	0.1409	0.069*
C5	0.77820 (8)	0.20250 (16)	0.21090 (17)	0.0509 (3)
H5A	0.7885	0.1174	0.2531	0.061*
C6	0.70357 (7)	0.25944 (14)	0.21570 (14)	0.0409 (3)
C7	0.64405 (8)	0.18409 (14)	0.29029 (15)	0.0448 (3)
H7A	0.6551	0.0949	0.3217	0.054*
C8	0.45912 (7)	0.19818 (14)	0.43038 (15)	0.0429 (3)
C9	0.43186 (8)	0.33897 (16)	0.37856 (19)	0.0542 (4)
H9A	0.4615	0.4101	0.4289	0.065*
H9B	0.4423	0.3476	0.2800	0.065*
C10	0.34576 (8)	0.36138 (14)	0.39812 (16)	0.0468 (3)
C11	0.29124 (9)	0.30706 (16)	0.30280 (18)	0.0566 (4)
H11A	0.3085	0.2621	0.2238	0.068*
C12	0.21138 (9)	0.31748 (17)	0.32120 (19)	0.0570 (4)
H12A	0.1759	0.2789	0.2559	0.068*
C13	0.18467 (8)	0.38616 (16)	0.43821 (17)	0.0508 (3)
C14	0.23916 (9)	0.44558 (18)	0.53125 (16)	0.0557 (4)
H14A	0.2221	0.4946	0.6079	0.067*
C15	0.31841 (9)	0.43303 (17)	0.51179 (16)	0.0527 (3)
H15A	0.3540	0.4732	0.5759	0.063*
C16	0.03229 (11)	0.3267 (3)	0.3351 (3)	0.0869 (6)
H16A	−0.0227	0.3311	0.3511	0.130*
H16B	0.0480	0.2318	0.3277	0.130*
H16C	0.0428	0.3744	0.2499	0.130*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0641 (3)	0.1044 (4)	0.0953 (4)	−0.0326 (3)	0.0244 (3)	0.0087 (3)
S1	0.0464 (2)	0.0932 (4)	0.0895 (4)	0.0137 (2)	0.0113 (2)	−0.0114 (3)
O1	0.0428 (5)	0.0508 (6)	0.0643 (7)	−0.0037 (4)	0.0130 (5)	0.0114 (5)
N1	0.0419 (6)	0.0468 (6)	0.0534 (7)	−0.0020 (5)	0.0129 (5)	0.0063 (5)
N2	0.0442 (6)	0.0456 (6)	0.0642 (8)	0.0015 (5)	0.0160 (5)	0.0132 (6)
C1	0.0417 (6)	0.0492 (8)	0.0466 (7)	0.0028 (5)	0.0053 (5)	0.0008 (6)
C2	0.0561 (8)	0.0507 (8)	0.0511 (8)	−0.0055 (7)	0.0068 (6)	0.0041 (6)
C3	0.0450 (7)	0.0645 (9)	0.0513 (8)	−0.0145 (7)	0.0091 (6)	−0.0050 (7)
C4	0.0384 (7)	0.0679 (10)	0.0665 (10)	0.0024 (7)	0.0094 (6)	−0.0055 (8)
C5	0.0453 (7)	0.0493 (8)	0.0587 (9)	0.0054 (6)	0.0099 (6)	0.0006 (7)
C6	0.0396 (6)	0.0431 (7)	0.0402 (7)	−0.0001 (5)	0.0061 (5)	−0.0034 (5)
C7	0.0445 (7)	0.0419 (7)	0.0486 (8)	0.0006 (5)	0.0076 (6)	0.0021 (6)
C8	0.0384 (6)	0.0435 (7)	0.0472 (7)	−0.0051 (5)	0.0064 (5)	0.0006 (6)
C9	0.0457 (7)	0.0458 (8)	0.0722 (10)	−0.0010 (6)	0.0166 (7)	0.0080 (7)
C10	0.0454 (7)	0.0394 (7)	0.0563 (8)	0.0023 (5)	0.0108 (6)	0.0070 (6)
C11	0.0557 (8)	0.0532 (8)	0.0619 (10)	0.0023 (7)	0.0143 (7)	−0.0126 (7)
C12	0.0505 (8)	0.0545 (9)	0.0659 (10)	0.0017 (7)	0.0031 (7)	−0.0119 (7)
C13	0.0457 (7)	0.0502 (8)	0.0569 (9)	0.0093 (6)	0.0067 (6)	0.0044 (7)
C14	0.0541 (8)	0.0666 (10)	0.0468 (8)	0.0132 (7)	0.0065 (6)	−0.0047 (7)
C15	0.0504 (8)	0.0575 (9)	0.0501 (8)	0.0046 (6)	0.0007 (6)	−0.0003 (7)
C16	0.0516 (10)	0.1089 (18)	0.0998 (16)	−0.0040 (10)	−0.0003 (10)	−0.0019 (13)

Geometric parameters (Å, º) top

Cl1—C3	1.7386 (15)	C7—H7A	0.9300
S1—C13	1.7590 (15)	C8—C9	1.516 (2)
S1—C16	1.783 (2)	C9—C10	1.5069 (19)
O1—C8	1.2310 (16)	C9—H9A	0.9700
N1—C7	1.2728 (17)	C9—H9B	0.9700
N1—N2	1.3828 (15)	C10—C11	1.380 (2)
N2—C8	1.3462 (17)	C10—C15	1.386 (2)
N2—H1N2	0.9458	C11—C12	1.387 (2)
C1—C2	1.3840 (19)	C11—H11A	0.9300
C1—C6	1.391 (2)	C12—C13	1.394 (2)
C1—H1A	0.9300	C12—H12A	0.9300
C2—C3	1.383 (2)	C13—C14	1.385 (2)
C2—H2A	0.9300	C14—C15	1.380 (2)
C3—C4	1.376 (2)	C14—H14A	0.9300
C4—C5	1.382 (2)	C15—H15A	0.9300
C4—H4A	0.9300	C16—H16A	0.9600
C5—C6	1.3920 (18)	C16—H16B	0.9600
C5—H5A	0.9300	C16—H16C	0.9600
C6—C7	1.4612 (18)

C13—S1—C16	104.73 (9)	C10—C9—H9A	109.2
C7—N1—N2	114.68 (12)	C8—C9—H9A	109.2
C8—N2—N1	121.57 (12)	C10—C9—H9B	109.2
C8—N2—H1N2	117.9	C8—C9—H9B	109.2
N1—N2—H1N2	120.4	H9A—C9—H9B	107.9
C2—C1—C6	120.69 (13)	C11—C10—C15	117.86 (13)
C2—C1—H1A	119.7	C11—C10—C9	119.97 (14)
C6—C1—H1A	119.7	C15—C10—C9	122.16 (14)
C3—C2—C1	118.83 (14)	C10—C11—C12	121.98 (14)
C3—C2—H2A	120.6	C10—C11—H11A	119.0
C1—C2—H2A	120.6	C12—C11—H11A	119.0
C4—C3—C2	121.80 (14)	C11—C12—C13	119.56 (15)
C4—C3—Cl1	119.02 (12)	C11—C12—H12A	120.2
C2—C3—Cl1	119.18 (13)	C13—C12—H12A	120.2
C3—C4—C5	118.81 (14)	C14—C13—C12	118.61 (14)
C3—C4—H4A	120.6	C14—C13—S1	116.28 (12)
C5—C4—H4A	120.6	C12—C13—S1	125.11 (13)
C4—C5—C6	120.94 (14)	C15—C14—C13	120.94 (14)
C4—C5—H5A	119.5	C15—C14—H14A	119.5
C6—C5—H5A	119.5	C13—C14—H14A	119.5
C1—C6—C5	118.92 (13)	C14—C15—C10	120.97 (15)
C1—C6—C7	122.62 (12)	C14—C15—H15A	119.5
C5—C6—C7	118.45 (13)	C10—C15—H15A	119.5
N1—C7—C6	122.07 (13)	S1—C16—H16A	109.5
N1—C7—H7A	119.0	S1—C16—H16B	109.5
C6—C7—H7A	119.0	H16A—C16—H16B	109.5
O1—C8—N2	119.34 (13)	S1—C16—H16C	109.5
O1—C8—C9	123.30 (12)	H16A—C16—H16C	109.5
N2—C8—C9	117.36 (12)	H16B—C16—H16C	109.5
C10—C9—C8	112.16 (11)

C7—N1—N2—C8	175.46 (13)	O1—C8—C9—C10	−14.8 (2)
C6—C1—C2—C3	−0.5 (2)	N2—C8—C9—C10	164.74 (14)
C1—C2—C3—C4	1.1 (2)	C8—C9—C10—C11	−81.06 (19)
C1—C2—C3—Cl1	−179.53 (11)	C8—C9—C10—C15	97.43 (17)
C2—C3—C4—C5	−1.0 (2)	C15—C10—C11—C12	−2.7 (2)
Cl1—C3—C4—C5	179.58 (12)	C9—C10—C11—C12	175.83 (15)
C3—C4—C5—C6	0.4 (2)	C10—C11—C12—C13	0.8 (3)
C2—C1—C6—C5	−0.1 (2)	C11—C12—C13—C14	1.7 (2)
C2—C1—C6—C7	178.68 (14)	C11—C12—C13—S1	−179.14 (13)
C4—C5—C6—C1	0.1 (2)	C16—S1—C13—C14	177.21 (14)
C4—C5—C6—C7	−178.68 (14)	C16—S1—C13—C12	−1.93 (18)
N2—N1—C7—C6	−177.96 (12)	C12—C13—C14—C15	−2.3 (2)
C1—C6—C7—N1	−7.3 (2)	S1—C13—C14—C15	178.46 (13)
C5—C6—C7—N1	171.47 (14)	C13—C14—C15—C10	0.4 (2)
N1—N2—C8—O1	−174.81 (13)	C11—C10—C15—C14	2.1 (2)
N1—N2—C8—C9	5.6 (2)	C9—C10—C15—C14	−176.42 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1ⁱ	0.95	2.03	2.9784 (17)	176
C14—H14A···Cg1ⁱⁱ	0.93	2.89	3.7627 (17)	156
C5—H5A···Cg2ⁱⁱⁱ	0.93	2.98	3.4638 (17)	114

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅ClN₂OS
M_r	318.81
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	17.0923 (13), 9.6719 (7), 9.5592 (7)
β (°)	92.399 (1)
V (Å³)	1578.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.91 × 0.49 × 0.09

Data collection
Diffractometer	Bruker APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.728, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	17083, 4748, 3306
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.711

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.122, 1.04
No. of reflections	4748
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.41

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1ⁱ	0.95	2.03	2.9784 (17)	176
C14—H14A···Cg1ⁱⁱ	0.93	2.89	3.7627 (17)	156
C5—H5A···Cg2ⁱⁱⁱ	0.93	2.98	3.4638 (17)	114

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y−1/2, −z+1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

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