Crystal structure of (E)-N′-(4-chloro­benzyl­idene)-4-methyl­benzene­sulfono­hydrazide: a hexa­gonal polymorph

Balaji, J.; John Francis Xavier, J.; Prabu, S.; Srinivasan, P.

doi:10.1107/S1600536814023721

organic compounds

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ISSN: 2056-9890

Volume 70| Part 12| December 2014| Pages o1250-o1251

doi:10.1107/S1600536814023721

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Crystal structure of (E)-N′-(4-chlorobenzylidene)-4-methylbenzenesulfonohydrazide: a hexagonal polymorph

J. Balaji,^a J. John Francis Xavier,^b S. Prabu ^a and P. Srinivasan ^a ^*

^aDepartment of Physics, University College of Engineering Panruti, Tamil Nadu 607 106, India, and ^bDepartment of Chemistry, University College of Engineering Panruti, Tamil Nadu 607 106, India
^*Correspondence e-mail: sril35@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 14 October 2014; accepted 28 October 2014; online 12 November 2014)

The title compound, C₁₄H₁₃ClN₂O₂S, crystallized in the enantiomorphic defining hexagonal space group P6₁ [Flack parameter = −0.02 (7)]. The partially hydrated form of the same compound, crystallizing in the triclinic space group P-1, has been reported previously [Kia et al. (2009b). Acta Cryst. E65, o1119], as has the crystal structure of the bromo derivative, also crystallizing in the space group P-1 [Kia et al. (2009a). Acta Cryst. E65, o821]. The title molecule is non-planar with the planes of the benzene rings being inclined to one another by 76.62 (13)°, and has an E conformation about the C=N bond. In the crystal, molecules are linked via N—H⋯O hydrogen bonds forming 6₁ helical chains running along [001]. The chains are linked via C—H⋯O hydrogen bonds, C—H⋯π interactions and short Cl⋯O [3.015 (3) Å] interactions, forming a three-dimensional structure.

Keywords: crystal structure; hydrazones; sulfonohydrazide; Schiff base; helical chains; hydrogen bonding..

CCDC reference: 1031289

1. Related literature

For the biological activities of hydrazones, see: Ajani et al. (2010 ). For the crystal structure of the triclinic polymorph, which crystallized with two independent molecules in the asymmetric unit, one of which was disordered, and with 0.15 of a water molecule, see: Kia et al. (2009b ). For the crystal structure of the bromo derivative, also crystallizing in space group P $[\overline{1}]$ , see: Kia et al. (2009a ).

2. Experimental

2.1. Crystal data

C₁₄H₁₃ClN₂O₂S
M_r = 308.77
Hexagonal, P 6₁
a = 10.8907 (3) Å
c = 21.4542 (7) Å
V = 2203.71 (11) Å³
Z = 6
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.25 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.871, T_max = 0.910
22095 measured reflections
2586 independent reflections
2345 reflections with I > 2σ(I)
R_int = 0.027

2.3. Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.072
S = 1.04
2586 reflections
186 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ), 1257 Friedel pairs
Absolute structure parameter: −0.02 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.88 (2)	2.13 (2)	2.952 (3)	156 (2)
C1—H1A⋯O1ⁱⁱ	0.96	2.55	3.496 (5)	169
C13—H13⋯Cgⁱⁱⁱ	0.93	2.94	3.823 (3)	160
Symmetry codes: (i) $[x-y, x, z+{\script{1\over 6}}]$ ; (ii) $[x-y-1, x-1, z+{\script{1\over 6}}]$ ; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1031289

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814023721/su2800sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814023721/su2800Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814023721/su2800Isup3.cml

checkCIF report

Comment top

The title compound was obtained by a Schiff base condensation reaction between 4-chlorobenzaldehyde and tosyl hydrazide. Hydrazones have received much attention recently due to their biological activities (Ajani et al., 2010). The crystal structure of the triclinic polymorph, that crystallized with two independent molecules in the asymmetric unit, one of which was disordered, and with 0.15 of a water molecule, has been reported (Kia et al., 2009b), as has the crystal structure of the bromo derivative, also crystallizing in space group P1 (Kia et al., 2009a).

The hydrazone molecule, Fig. 1, exists in a trans or E confirmation with respect to the C8═N2 bond. The dihedral angle between the (C2—C7) and (C9—C14) benzene rings is 76.62 (13) °. In the triclininc polymorph (Kia et al., 2009b) the same angle is 84.96 (11) ° (and 71.1 (3) ° for the disordered molecule), and 82.39 (13) ° for the bromo derivative (Kia et al., 2009a).

In the crystal, molecules are linked via N—H···O hydrogen bonds forming 6₁ helical chains running along the c axis direction (Table 1 and Fig 2). The chains are linked via C-H···O hydrogen bonds, and a short Cl···O2ⁱ [3.015 (3) Å; symmetry code: (i) x-y+1, x, z+1/6] interaction and a C-H···π interaction, forming a three-dimensional structure (Table 1 and Fig. 2).

Related literature top

For the biological activities of hydrazones, see: Ajani et al. (2010). For the crystal structure of the triclinic polymorph, which crystallized with two independent molecules in the asymmetric unit, one of which was disordered, and with 0.15 of a water molecule, see: Kia et al. (2009b). For the crystal structure of the bromo derivative, also crystallizing in space group P1, see: Kia et al. (2009a).

Experimental top

4-chlorobenzaldehyde (0.140 g, 1 mmol) and tosyl hydrazide (0.186 g, 1 mmol) were dissolved in ethanol and chloroform (4:1). The reaction mixture was heated under reflux for 3 h and cooled gradually to room temperature. Prismatic colourless crystals were obtained by slow evaporation of an ethanol solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

The molecular structure of the title compound, with atom labelling. The displacement ellipsoids are drawn at the 30% probability level.

A view along the c axis of the crystal packing of the title compound. The N—H···O and C—H···O hydrogen bonds are indicated by dashed lines (see Table 1 for details; H atoms not involved in these interactions have been omitted for clarity).

(E)-N'-(4-Chlorobenzylidene)-4-methylbenzenesulfonohydrazide top

Crystal data top

C₁₄H₁₃ClN₂O₂S	D_x = 1.396 Mg m⁻³
M_r = 308.77	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P6₁	Cell parameters from 9375 reflections
Hall symbol: P 61	θ = 2.4–25.8°
a = 10.8907 (3) Å	µ = 0.40 mm⁻¹
c = 21.4542 (7) Å	T = 293 K
V = 2203.71 (11) Å³	Block, yellow
Z = 6	0.35 × 0.30 × 0.25 mm
F(000) = 960

Data collection top

Bruker Kappa APEXII CCD diffractometer	2586 independent reflections
Radiation source: fine-focus sealed tube	2345 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scan	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.871, T_max = 0.910	k = −12→12
22095 measured reflections	l = −25→25

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.029	w = 1/[σ²(F_o²) + (0.0306P)² + 0.7106P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.072	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 0.12 e Å⁻³
2586 reflections	Δρ_min = −0.16 e Å⁻³
186 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0026 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1257 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.02 (7)

Crystal data top

C₁₄H₁₃ClN₂O₂S	Z = 6
M_r = 308.77	Mo Kα radiation
Hexagonal, P6₁	µ = 0.40 mm⁻¹
a = 10.8907 (3) Å	T = 293 K
c = 21.4542 (7) Å	0.35 × 0.30 × 0.25 mm
V = 2203.71 (11) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	2586 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2345 reflections with I > 2σ(I)
T_min = 0.871, T_max = 0.910	R_int = 0.027
22095 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.072	Δρ_max = 0.12 e Å⁻³
S = 1.04	Δρ_min = −0.16 e Å⁻³
2586 reflections	Absolute structure: Flack (1983), 1257 Friedel pairs
186 parameters	Absolute structure parameter: −0.02 (7)
2 restraints

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
C1	−0.1026 (3)	−0.5080 (4)	0.94696 (15)	0.0727 (9)
H1A	−0.2001	−0.5364	0.9392	0.109*
H1B	−0.0699	−0.4482	0.9831	0.109*
H1C	−0.0942	−0.5906	0.9539	0.109*
C2	−0.0151 (3)	−0.4286 (3)	0.89196 (13)	0.0480 (6)
C3	−0.0778 (3)	−0.4059 (3)	0.84061 (13)	0.0507 (6)
H3	−0.1751	−0.4410	0.8405	0.061*
C4	0.0019 (3)	−0.3321 (3)	0.78968 (12)	0.0496 (6)
H4	−0.0415	−0.3180	0.7553	0.060*
C5	0.1458 (2)	−0.2795 (2)	0.79003 (11)	0.0419 (5)
C6	0.2103 (3)	−0.3013 (3)	0.84070 (12)	0.0483 (6)
H6	0.3077	−0.2657	0.8408	0.058*
C7	0.1296 (3)	−0.3758 (3)	0.89098 (13)	0.0514 (6)
H7	0.1730	−0.3911	0.9250	0.062*
C8	0.1633 (3)	0.1027 (3)	0.74279 (11)	0.0426 (5)
H8	0.2543	0.1797	0.7474	0.051*
C9	0.0430 (3)	0.1244 (3)	0.74794 (10)	0.0415 (5)
C10	−0.0947 (3)	0.0146 (3)	0.74508 (13)	0.0520 (6)
H10	−0.1127	−0.0766	0.7367	0.062*
C11	−0.2070 (3)	0.0381 (3)	0.75456 (13)	0.0579 (7)
H11	−0.3000	−0.0366	0.7526	0.069*
C12	−0.1789 (3)	0.1731 (3)	0.76682 (12)	0.0522 (6)
C13	−0.0439 (3)	0.2844 (3)	0.76863 (13)	0.0574 (7)
H13	−0.0266	0.3758	0.7763	0.069*
C14	0.0664 (3)	0.2595 (3)	0.75898 (12)	0.0516 (6)
H14	0.1589	0.3353	0.7599	0.062*
O1	0.3852 (2)	−0.1677 (2)	0.73010 (9)	0.0597 (5)
O2	0.1652 (2)	−0.2455 (2)	0.67125 (8)	0.0605 (5)
S1	0.24764 (7)	−0.18427 (7)	0.72562 (3)	0.04549 (16)
Cl1	−0.31836 (9)	0.20068 (10)	0.78326 (4)	0.0779 (3)
N1	0.2735 (2)	−0.0230 (2)	0.73014 (10)	0.0445 (5)
N2	0.1474 (2)	−0.0187 (2)	0.73212 (9)	0.0424 (5)
H1	0.337 (2)	0.033 (2)	0.7573 (10)	0.050 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0601 (19)	0.084 (2)	0.0681 (19)	0.0315 (17)	0.0065 (15)	0.0170 (17)
C2	0.0489 (14)	0.0454 (14)	0.0498 (13)	0.0237 (12)	−0.0031 (13)	−0.0033 (12)
C3	0.0402 (14)	0.0510 (15)	0.0621 (16)	0.0238 (12)	−0.0056 (12)	−0.0032 (13)
C4	0.0518 (15)	0.0533 (15)	0.0512 (14)	0.0319 (13)	−0.0149 (12)	−0.0028 (13)
C5	0.0472 (14)	0.0423 (13)	0.0434 (13)	0.0278 (12)	−0.0050 (11)	−0.0061 (11)
C6	0.0403 (14)	0.0609 (16)	0.0473 (14)	0.0280 (13)	−0.0056 (11)	−0.0017 (12)
C7	0.0511 (15)	0.0625 (16)	0.0432 (12)	0.0304 (13)	−0.0069 (12)	0.0017 (13)
C8	0.0491 (15)	0.0436 (14)	0.0383 (12)	0.0255 (12)	−0.0016 (10)	−0.0019 (10)
C9	0.0537 (15)	0.0440 (13)	0.0353 (11)	0.0309 (12)	−0.0025 (10)	0.0000 (10)
C10	0.0600 (17)	0.0442 (15)	0.0621 (16)	0.0338 (14)	−0.0055 (13)	−0.0075 (12)
C11	0.0540 (16)	0.0562 (17)	0.0695 (18)	0.0321 (14)	−0.0018 (13)	−0.0022 (14)
C12	0.0623 (17)	0.0643 (18)	0.0480 (14)	0.0452 (15)	−0.0021 (12)	−0.0023 (13)
C13	0.0733 (19)	0.0496 (16)	0.0658 (17)	0.0430 (16)	−0.0017 (14)	−0.0071 (13)
C14	0.0529 (16)	0.0444 (15)	0.0627 (17)	0.0282 (13)	−0.0049 (12)	−0.0057 (12)
O1	0.0637 (12)	0.0735 (13)	0.0631 (11)	0.0502 (11)	0.0132 (9)	0.0121 (10)
O2	0.0933 (15)	0.0647 (12)	0.0418 (9)	0.0533 (12)	−0.0108 (10)	−0.0124 (9)
S1	0.0604 (4)	0.0513 (4)	0.0401 (3)	0.0394 (3)	0.0020 (3)	−0.0015 (3)
Cl1	0.0746 (5)	0.0945 (6)	0.0928 (6)	0.0635 (5)	−0.0005 (5)	−0.0118 (5)
N1	0.0498 (13)	0.0489 (12)	0.0446 (11)	0.0320 (11)	−0.0005 (10)	−0.0030 (10)
N2	0.0511 (12)	0.0469 (12)	0.0400 (11)	0.0327 (10)	−0.0022 (9)	−0.0032 (9)

Geometric parameters (Å, º) top

C1—C2	1.491 (4)	C8—H8	0.9300
C1—H1A	0.9600	C9—C10	1.374 (3)
C1—H1B	0.9600	C9—C14	1.383 (3)
C1—H1C	0.9600	C10—C11	1.384 (4)
C2—C7	1.381 (3)	C10—H10	0.9300
C2—C3	1.382 (4)	C11—C12	1.369 (4)
C3—C4	1.376 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.360 (4)
C4—C5	1.374 (3)	C12—Cl1	1.726 (3)
C4—H4	0.9300	C13—C14	1.373 (4)
C5—C6	1.378 (3)	C13—H13	0.9300
C5—S1	1.751 (3)	C14—H14	0.9300
C6—C7	1.372 (4)	O1—S1	1.4197 (18)
C6—H6	0.9300	O2—S1	1.4189 (19)
C7—H7	0.9300	S1—N1	1.637 (2)
C8—N2	1.265 (3)	N1—N2	1.399 (3)
C8—C9	1.447 (3)	N1—H1	0.875 (17)

C2—C1—H1A	109.5	C10—C9—C8	122.5 (2)
C2—C1—H1B	109.5	C14—C9—C8	119.1 (2)
H1A—C1—H1B	109.5	C9—C10—C11	120.9 (2)
C2—C1—H1C	109.5	C9—C10—H10	119.6
H1A—C1—H1C	109.5	C11—C10—H10	119.6
H1B—C1—H1C	109.5	C12—C11—C10	118.8 (3)
C7—C2—C3	118.4 (2)	C12—C11—H11	120.6
C7—C2—C1	121.2 (3)	C10—C11—H11	120.6
C3—C2—C1	120.3 (2)	C13—C12—C11	121.6 (2)
C4—C3—C2	120.9 (2)	C13—C12—Cl1	119.5 (2)
C4—C3—H3	119.5	C11—C12—Cl1	118.8 (2)
C2—C3—H3	119.5	C12—C13—C14	118.8 (2)
C5—C4—C3	119.6 (2)	C12—C13—H13	120.6
C5—C4—H4	120.2	C14—C13—H13	120.6
C3—C4—H4	120.2	C13—C14—C9	121.5 (3)
C4—C5—C6	120.4 (2)	C13—C14—H14	119.3
C4—C5—S1	119.71 (18)	C9—C14—H14	119.3
C6—C5—S1	119.89 (19)	O2—S1—O1	119.65 (12)
C7—C6—C5	119.4 (2)	O2—S1—N1	106.40 (11)
C7—C6—H6	120.3	O1—S1—N1	104.78 (11)
C5—C6—H6	120.3	O2—S1—C5	107.80 (12)
C6—C7—C2	121.2 (2)	O1—S1—C5	109.72 (11)
C6—C7—H7	119.4	N1—S1—C5	107.91 (11)
C2—C7—H7	119.4	N2—N1—S1	113.13 (16)
N2—C8—C9	121.5 (2)	N2—N1—H1	113.4 (17)
N2—C8—H8	119.3	S1—N1—H1	116.2 (17)
C9—C8—H8	119.3	C8—N2—N1	114.7 (2)
C10—C9—C14	118.3 (2)

C7—C2—C3—C4	−0.2 (4)	C11—C12—C13—C14	−1.2 (4)
C1—C2—C3—C4	179.7 (3)	Cl1—C12—C13—C14	176.3 (2)
C2—C3—C4—C5	−0.4 (4)	C12—C13—C14—C9	−0.4 (4)
C3—C4—C5—C6	0.6 (4)	C10—C9—C14—C13	1.8 (4)
C3—C4—C5—S1	−179.42 (19)	C8—C9—C14—C13	−175.3 (2)
C4—C5—C6—C7	−0.1 (4)	C4—C5—S1—O2	−35.4 (2)
S1—C5—C6—C7	179.9 (2)	C6—C5—S1—O2	144.6 (2)
C5—C6—C7—C2	−0.5 (4)	C4—C5—S1—O1	−167.3 (2)
C3—C2—C7—C6	0.7 (4)	C6—C5—S1—O1	12.8 (2)
C1—C2—C7—C6	−179.2 (3)	C4—C5—S1—N1	79.1 (2)
N2—C8—C9—C10	3.7 (4)	C6—C5—S1—N1	−100.9 (2)
N2—C8—C9—C14	−179.3 (2)	O2—S1—N1—N2	57.70 (19)
C14—C9—C10—C11	−1.6 (4)	O1—S1—N1—N2	−174.64 (16)
C8—C9—C10—C11	175.4 (2)	C5—S1—N1—N2	−57.77 (18)
C9—C10—C11—C12	0.1 (4)	C9—C8—N2—N1	−178.3 (2)
C10—C11—C12—C13	1.3 (4)	S1—N1—N2—C8	172.28 (18)
C10—C11—C12—Cl1	−176.2 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.88 (2)	2.13 (2)	2.952 (3)	156 (2)
C1—H1A···O1ⁱⁱ	0.96	2.55	3.496 (5)	169
C13—H13···Cgⁱⁱⁱ	0.93	2.94	3.823 (3)	160

Symmetry codes: (i) x−y, x, z+1/6; (ii) x−y−1, x−1, z+1/6; (iii) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.875 (17)	2.133 (19)	2.952 (3)	156 (2)
C1—H1A···O1ⁱⁱ	0.96	2.55	3.496 (5)	169
C13—H13···Cgⁱⁱⁱ	0.93	2.94	3.823 (3)	160

Symmetry codes: (i) x−y, x, z+1/6; (ii) x−y−1, x−1, z+1/6; (iii) x, y+1, z.

Acknowledgements

The authors thank the SAIF, IITM, Madras, for help with the XRD studies.

References

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Volume 70| Part 12| December 2014| Pages o1250-o1251

doi:10.1107/S1600536814023721

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

Crystal structure of (E)-N′-(4-chloro­benzyl­­idene)-4-methyl­benzene­sulfono­hydrazide: a hexa­gonal polymorph

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (E)-N′-(4-chlorobenzylidene)-4-methylbenzenesulfonohydrazide: a hexagonal polymorph