(E)-N'-Benzyl-idene-p-toluene-sulfono-hydrazide.

In the title compound, C(14)H(14)N(2)O(2)S, a novel sulfonamide derivative, an intra-molecular C-H⋯O hydrogen bond generates an S(5) ring motif. The mol-ecule adopts a twisted E configuration around the C=N bond. An inter-molecular N-H⋯O hydrogen bond generates an R(2) (2)(8) ring motif. The dihedral angle between the rings is 85.37 (9)°. The H atoms of the methyl group have rotational disorder with refined site occupancies of ca 0.63/0.37. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link neighbouring mol-ecules into dimers which stack along the a axis with a centroid-centroid distance of 3.8856 (10) Å.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures and applications, see, for example: Tabatabaee et al. (2007 ▶); Ali et al. (2007 ▶); Tierney et al. (2006 ▶); Krygowski et al. (1998 ▶); Kayser et al. (2004 ▶).

Experimental

Crystal data

C14H14N2O2S

M = 274.33

Monoclinic,

a = 5.9593 (7) Å

b = 9.6592 (7) Å

c = 23.712 (3) Å

β = 91.533 (9)°

V = 1364.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 293 (2) K

0.50 × 0.40 × 0.03 mm

Data collection

STOE IPDSII diffractometer

Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2004 ▶) T min = 0.879, T max = 0.993

8939 measured reflections

3573 independent reflections

3008 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.110

S = 1.10

3573 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.25 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; 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,2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027219/at2617sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027219/at2617Isup2.hkl

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

C14H14N2O2S	F000 = 576
Mr = 274.33	Dx = 1.336 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2500 reflections
a = 5.9593 (7) Å	θ = 2.3–29.2º
b = 9.6592 (7) Å	µ = 0.24 mm−1
c = 23.712 (3) Å	T = 293 (2) K
β = 91.533 (9)º	Plate, colourless
V = 1364.4 (3) Å3	0.50 × 0.40 × 0.03 mm
Z = 4

STOE IPDSII diffractometer	3573 independent reflections
Radiation source: fine-focus sealed tube	3008 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
Detector resolution: 0.15 pixels mm-1	θmax = 29.0º
T = 293(2) K	θmin = 2.3º
φ scans	h = −8→6
Absorption correction: numerical(X-SHAPE; Stoe & Cie, 2004)	k = −12→13
Tmin = 0.879, Tmax = 0.993	l = −32→32
8939 measured reflections

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0507P)2 + 0.2385P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
3573 reflections	Δρmax = 0.23 e Å−3
195 parameters	Δρmin = −0.25 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.24869 (6)	0.18884 (4)	0.001194 (15)	0.04475 (12)
O1	0.39754 (19)	0.13796 (12)	−0.04087 (4)	0.0555 (3)
O2	0.03368 (18)	0.24148 (12)	−0.01555 (5)	0.0572 (3)
N1	0.2191 (2)	0.05429 (14)	0.04190 (6)	0.0531 (3)
H1N1	0.328 (3)	−0.004 (2)	0.0425 (8)	0.063 (5)*
N2	0.0856 (2)	0.06535 (13)	0.08855 (6)	0.0500 (3)
C1	0.6026 (2)	0.28675 (16)	0.06340 (7)	0.0504 (3)
H1A	0.6706	0.2023	0.0558	0.060*
C2	0.7124 (3)	0.38438 (18)	0.09592 (7)	0.0565 (4)
H2A	0.8548	0.3648	0.1108	0.068*
C3	0.6147 (3)	0.51220 (17)	0.10705 (6)	0.0542 (4)
C4	0.4028 (3)	0.53993 (16)	0.08404 (7)	0.0551 (4)
H4A	0.3367	0.6255	0.0905	0.066*
C5	0.2883 (2)	0.44255 (15)	0.05169 (6)	0.0480 (3)
H5A	0.1460	0.4619	0.0367	0.058*
C6	0.3884 (2)	0.31589 (14)	0.04191 (6)	0.0418 (3)
C7	0.1133 (3)	−0.03135 (15)	0.12464 (7)	0.0509 (3)
H7A	0.2260	−0.0962	0.1192	0.061*
C8	−0.0264 (3)	−0.04390 (16)	0.17434 (6)	0.0516 (3)
C9	0.0359 (3)	−0.1379 (2)	0.21640 (7)	0.0655 (4)
H9A	0.1678	−0.1885	0.2134	0.079*
C10	−0.0980 (5)	−0.1566 (3)	0.26284 (8)	0.0807 (6)
H10A	−0.0555	−0.2196	0.2908	0.097*
C11	−0.2921 (5)	−0.0825 (3)	0.26759 (9)	0.0884 (7)
H11A	−0.3815	−0.0953	0.2987	0.106*
C12	−0.3558 (4)	0.0115 (3)	0.22621 (10)	0.0858 (6)
H12A	−0.4876	0.0620	0.2296	0.103*
C13	−0.2239 (3)	0.0303 (2)	0.17986 (8)	0.0677 (5)
H13A	−0.2679	0.0933	0.1521	0.081*
C14	0.7396 (5)	0.6169 (3)	0.14314 (10)	0.0776 (6)
H14A	0.651 (10)	0.695 (7)	0.147 (3)	0.116*	0.63 (4)
H14B	0.855 (10)	0.656 (7)	0.124 (2)	0.116*	0.63 (4)
H14C	0.789 (11)	0.581 (6)	0.177 (2)	0.116*	0.63 (4)
H14D	0.73 (2)	0.714 (12)	0.128 (4)	0.116*	0.37 (4)
H14E	0.920 (16)	0.579 (9)	0.151 (4)	0.116*	0.37 (4)
H14F	0.648 (17)	0.625 (10)	0.185 (4)	0.116*	0.37 (4)

	U11	U22	U33	U12	U13	U23
S1	0.04108 (18)	0.04409 (19)	0.04919 (19)	0.00320 (13)	0.00301 (13)	−0.00108 (14)
O1	0.0593 (6)	0.0565 (6)	0.0512 (5)	0.0086 (5)	0.0097 (5)	−0.0032 (5)
O2	0.0440 (6)	0.0602 (6)	0.0668 (7)	0.0048 (5)	−0.0070 (5)	−0.0030 (5)
N1	0.0518 (7)	0.0427 (6)	0.0656 (8)	0.0037 (5)	0.0150 (6)	0.0018 (6)
N2	0.0461 (6)	0.0451 (6)	0.0592 (7)	−0.0026 (5)	0.0096 (5)	−0.0020 (5)
C1	0.0421 (7)	0.0527 (8)	0.0564 (8)	0.0078 (6)	0.0017 (6)	0.0020 (6)
C2	0.0445 (7)	0.0672 (10)	0.0573 (8)	−0.0030 (7)	−0.0046 (6)	0.0058 (7)
C3	0.0606 (9)	0.0558 (8)	0.0463 (7)	−0.0140 (7)	0.0025 (6)	0.0044 (6)
C4	0.0635 (9)	0.0421 (7)	0.0600 (8)	0.0010 (6)	0.0065 (7)	0.0005 (6)
C5	0.0424 (7)	0.0448 (7)	0.0568 (8)	0.0051 (5)	0.0011 (6)	0.0043 (6)
C6	0.0376 (6)	0.0437 (7)	0.0442 (6)	0.0017 (5)	0.0049 (5)	0.0045 (5)
C7	0.0494 (8)	0.0433 (7)	0.0601 (8)	−0.0005 (6)	0.0041 (6)	−0.0039 (6)
C8	0.0559 (8)	0.0472 (7)	0.0515 (7)	−0.0083 (6)	0.0007 (6)	−0.0062 (6)
C9	0.0745 (11)	0.0648 (10)	0.0568 (9)	−0.0035 (9)	−0.0053 (8)	−0.0001 (8)
C10	0.1072 (17)	0.0847 (14)	0.0501 (9)	−0.0107 (12)	−0.0013 (10)	0.0050 (9)
C11	0.1082 (18)	0.1013 (17)	0.0570 (10)	−0.0159 (14)	0.0253 (11)	−0.0081 (11)
C12	0.0802 (14)	0.0963 (16)	0.0823 (13)	0.0054 (12)	0.0281 (11)	−0.0057 (12)
C13	0.0655 (11)	0.0687 (11)	0.0695 (10)	0.0047 (8)	0.0135 (8)	0.0040 (9)
C14	0.0961 (17)	0.0716 (13)	0.0646 (11)	−0.0275 (12)	−0.0085 (11)	−0.0039 (10)

S1—O2	1.4250 (11)	C7—H7A	0.9300
S1—O1	1.4389 (11)	C8—C13	1.387 (3)
S1—N1	1.6313 (14)	C8—C9	1.392 (2)
S1—C6	1.7573 (14)	C9—C10	1.389 (3)
N1—N2	1.3840 (18)	C9—H9A	0.9300
N1—H1N1	0.86 (2)	C10—C11	1.368 (4)
N2—C7	1.274 (2)	C10—H10A	0.9300
C1—C2	1.373 (2)	C11—C12	1.382 (3)
C1—C6	1.3908 (19)	C11—H11A	0.9300
C1—H1A	0.9300	C12—C13	1.380 (3)
C2—C3	1.393 (2)	C12—H12A	0.9300
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.388 (2)	C14—H14A	0.93 (7)
C3—C14	1.509 (2)	C14—H14B	0.92 (6)
C4—C5	1.382 (2)	C14—H14C	0.92 (6)
C4—H4A	0.9300	C14—H14D	1.00 (11)
C5—C6	1.3832 (19)	C14—H14E	1.15 (10)
C5—H5A	0.9300	C14—H14F	1.15 (10)
C7—C8	1.466 (2)
O2—S1—O1	119.68 (7)	C10—C9—H9A	119.8
O2—S1—N1	109.79 (7)	C8—C9—H9A	119.8
O1—S1—N1	102.50 (7)	C11—C10—C9	120.2 (2)
O2—S1—C6	108.24 (7)	C11—C10—H10A	119.9
O1—S1—C6	109.13 (7)	C9—C10—H10A	119.9
N1—S1—C6	106.76 (7)	C10—C11—C12	120.1 (2)
N2—N1—S1	119.01 (10)	C10—C11—H11A	119.9
N2—N1—H1N1	119.1 (13)	C12—C11—H11A	119.9
S1—N1—H1N1	116.1 (13)	C13—C12—C11	120.0 (2)
C7—N2—N1	114.41 (13)	C13—C12—H12A	120.0
C2—C1—C6	119.05 (14)	C11—C12—H12A	120.0
C2—C1—H1A	120.5	C12—C13—C8	120.64 (19)
C6—C1—H1A	120.5	C12—C13—H13A	119.7
C1—C2—C3	121.33 (14)	C8—C13—H13A	119.7
C1—C2—H2A	119.3	C3—C14—H14A	109 (4)
C3—C2—H2A	119.3	C3—C14—H14B	111 (3)
C4—C3—C2	118.47 (14)	H14A—C14—H14B	99 (4)
C4—C3—C14	121.57 (19)	C3—C14—H14C	113 (3)
C2—C3—C14	119.96 (19)	H14A—C14—H14C	112 (5)
C5—C4—C3	121.13 (15)	H14B—C14—H14C	112 (5)
C5—C4—H4A	119.4	C3—C14—H14D	113 (5)
C3—C4—H4A	119.4	H14A—C14—H14D	41 (6)
C4—C5—C6	119.10 (14)	H14B—C14—H14D	59 (5)
C4—C5—H5A	120.4	H14C—C14—H14D	133 (6)
C6—C5—H5A	120.4	C3—C14—H14E	109 (4)
C5—C6—C1	120.88 (14)	H14A—C14—H14E	141 (5)
C5—C6—S1	120.65 (11)	H14B—C14—H14E	60 (4)
C1—C6—S1	118.47 (11)	H14C—C14—H14E	58 (4)
N2—C7—C8	122.31 (14)	H14D—C14—H14E	114 (7)
N2—C7—H7A	118.8	C3—C14—H14F	108 (4)
C8—C7—H7A	118.8	H14A—C14—H14F	64 (5)
C13—C8—C9	118.70 (16)	H14B—C14—H14F	141 (5)
C13—C8—C7	122.31 (15)	H14C—C14—H14F	54 (4)
C9—C8—C7	118.94 (16)	H14D—C14—H14F	102 (7)
C10—C9—C8	120.3 (2)	H14E—C14—H14F	110 (6)
O2—S1—N1—N2	−52.51 (14)	N1—S1—C6—C5	−119.42 (12)
O1—S1—N1—N2	179.27 (11)	O2—S1—C6—C1	179.55 (11)
C6—S1—N1—N2	64.61 (13)	O1—S1—C6—C1	−48.69 (13)
S1—N1—N2—C7	−164.31 (11)	N1—S1—C6—C1	61.41 (13)
C6—C1—C2—C3	−0.9 (2)	N1—N2—C7—C8	−174.66 (13)
C1—C2—C3—C4	−0.5 (2)	N2—C7—C8—C13	13.1 (2)
C1—C2—C3—C14	179.77 (17)	N2—C7—C8—C9	−169.75 (15)
C2—C3—C4—C5	1.2 (2)	C13—C8—C9—C10	0.0 (3)
C14—C3—C4—C5	−179.06 (17)	C7—C8—C9—C10	−177.21 (16)
C3—C4—C5—C6	−0.5 (2)	C8—C9—C10—C11	−0.1 (3)
C4—C5—C6—C1	−1.0 (2)	C9—C10—C11—C12	−0.1 (4)
C4—C5—C6—S1	179.82 (11)	C10—C11—C12—C13	0.3 (4)
C2—C1—C6—C5	1.7 (2)	C11—C12—C13—C8	−0.3 (3)
C2—C1—C6—S1	−179.11 (12)	C9—C8—C13—C12	0.1 (3)
O2—S1—C6—C5	−1.28 (14)	C7—C8—C13—C12	177.28 (18)
O1—S1—C6—C5	130.48 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.863 (19)	2.082 (19)	2.9446 (17)	177.0 (18)
C5—H5A···O2	0.93	2.54	2.9133 (18)	104

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.863 (19)	2.082 (19)	2.9446 (17)	177.0 (18)
C5—H5A⋯O2	0.93	2.54	2.9133 (18)	104

Symmetry code: (i) .