(E)-N'-(3,3-Diphenyl-allyl-idene)-p-toluene-sulfonohydrazide.

In the title compound, C(22)H(20)N(2)O(2)S, the mol-ecule adopts a twisted E configuration around the C=N bond. The two phenyl rings are twisted from each other, making a dihedral angle of 78.00 (12)°. The methyl-substituted benzene ring makes dihedral angles of 32.37 (14) and 69.70 (12)° with the two phenyl rings. In the crystal structure, mol-ecules are linked into extended chains along the b axis through inter-molecular N-H⋯O hydrogen bonds.

Related literature

For related compounds and their bioactivities, see; for example, Mehrabi et al. (2008 ▶); Tabatabaee et al. (2007 ▶); Ali et al. (2007 ▶); Tierney et al. 2006 ▶; Krygowski et al. (1998 ▶); Kayser et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C22H20N2O2S

M = 376.46

Monoclinic,

a = 14.785 (3) Å

b = 6.2179 (12) Å

c = 22.519 (5) Å

β = 102.64 (3)°

V = 2020.0 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 294 K

0.50 × 0.28 × 0.12 mm

Data collection

Stoe IPDS-II diffractometer

Absorption correction: numerical (X-RED32; Stoe & Cie, 2005 ▶) T min = 0.940, T max = 0.980

5327 measured reflections

5327 independent reflections

4220 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.156

S = 1.10

5327 reflections

249 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.26 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013269/at2762sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013269/at2762Isup2.hkl

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

C22H20N2O2S	F(000) = 792
Mr = 376.46	Dx = 1.238 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2500 reflections
a = 14.785 (3) Å	θ = 2.3–29.2°
b = 6.2179 (12) Å	µ = 0.18 mm−1
c = 22.519 (5) Å	T = 294 K
β = 102.64 (3)°	Block, colourless
V = 2020.0 (7) Å3	0.50 × 0.28 × 0.12 mm
Z = 4

Stoe IPDS-II diffractometer	5327 independent reflections
Radiation source: fine-focus sealed tube	4220 reflections with I > 2σ(I)
graphite	Rint = 0.0000
Detector resolution: 0.15 pixels mm-1	θmax = 29.0°, θmin = 1.9°
rotation method scans	h = −20→19
Absorption correction: numerical (X-RED32; Stoe & Cie, 2005)	k = 0→8
Tmin = 0.940, Tmax = 0.980	l = 0→30
5327 measured reflections

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0702P)2 + 0.4245P] where P = (Fo2 + 2Fc2)/3
5327 reflections	(Δ/σ)max < 0.001
249 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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
S1	0.36602 (3)	0.58739 (7)	0.24598 (2)	0.05559 (15)
O1	0.39657 (11)	0.7837 (2)	0.22433 (7)	0.0741 (4)
O2	0.30743 (11)	0.5917 (2)	0.28899 (6)	0.0719 (4)
N1	0.35283 (10)	0.4163 (2)	0.14209 (6)	0.0542 (3)
N2	0.30481 (11)	0.4572 (3)	0.18786 (7)	0.0544 (3)
H1N2	0.2757 (15)	0.355 (4)	0.1974 (10)	0.065 (6)*
C1	0.35959 (15)	−0.1126 (3)	−0.08028 (10)	0.0681 (5)
H1	0.3228	−0.2220	−0.0702	0.082*
C2	0.40308 (17)	−0.1410 (4)	−0.12878 (11)	0.0781 (6)
H2	0.3953	−0.2693	−0.1505	0.094*
C3	0.45712 (15)	0.0186 (4)	−0.14457 (9)	0.0722 (6)
H3	0.4856	−0.0004	−0.1772	0.087*
C4	0.46904 (15)	0.2069 (4)	−0.11195 (9)	0.0695 (5)
H4	0.5062	0.3152	−0.1223	0.083*
C5	0.42599 (14)	0.2365 (3)	−0.06367 (9)	0.0616 (4)
H5	0.4344	0.3652	−0.0421	0.074*
C6	0.37052 (12)	0.0769 (3)	−0.04690 (7)	0.0521 (4)
C7	0.32394 (12)	0.1032 (3)	0.00479 (7)	0.0512 (4)
C8	0.23773 (13)	−0.0247 (3)	0.00290 (8)	0.0544 (4)
C9	0.15991 (16)	0.0142 (4)	−0.04264 (10)	0.0781 (6)
H9	0.1624	0.1197	−0.0715	0.094*
C10	0.07956 (19)	−0.0983 (5)	−0.04624 (15)	0.0994 (9)
H10	0.0282	−0.0704	−0.0774	0.119*
C11	0.0753 (2)	−0.2508 (5)	−0.0041 (2)	0.1177 (12)
H11	0.0205	−0.3268	−0.0061	0.141*
C12	0.1509 (3)	−0.2946 (5)	0.04175 (19)	0.1156 (11)
H12	0.1473	−0.4006	0.0703	0.139*
C13	0.23312 (18)	−0.1804 (4)	0.04555 (13)	0.0834 (7)
H13	0.2844	−0.2092	0.0766	0.100*
C14	0.35757 (13)	0.2367 (3)	0.05125 (8)	0.0569 (4)
H14	0.4129	0.3070	0.0508	0.068*
C15	0.31479 (13)	0.2803 (3)	0.10200 (8)	0.0538 (4)
H15	0.2605	0.2104	0.1053	0.065*
C16	0.46334 (13)	0.4280 (3)	0.27515 (8)	0.0570 (4)
C17	0.55009 (15)	0.4897 (5)	0.26802 (10)	0.0759 (6)
H17	0.5581	0.6184	0.2488	0.091*
C18	0.62509 (18)	0.3562 (6)	0.29011 (12)	0.0933 (8)
H18	0.6837	0.3981	0.2858	0.112*
C19	0.6153 (2)	0.1648 (5)	0.31798 (13)	0.0914 (8)
C22	0.6986 (2)	0.0211 (6)	0.3407 (2)	0.1415 (16)
H22A	0.7542	0.0967	0.3381	0.212*
H22B	0.6932	−0.1064	0.3162	0.212*
H22C	0.7010	−0.0179	0.3823	0.212*
C20	0.5286 (2)	0.1072 (4)	0.32492 (14)	0.0966 (9)
H20	0.5210	−0.0213	0.3444	0.116*
C21	0.45251 (17)	0.2363 (4)	0.30362 (12)	0.0786 (6)
H21	0.3942	0.1942	0.3084	0.094*

	U11	U22	U33	U12	U13	U23
S1	0.0643 (3)	0.0552 (2)	0.0519 (2)	−0.00057 (19)	0.02298 (19)	−0.01132 (18)
O1	0.0889 (10)	0.0543 (7)	0.0837 (9)	−0.0098 (7)	0.0286 (8)	−0.0086 (7)
O2	0.0832 (9)	0.0781 (9)	0.0640 (8)	0.0105 (7)	0.0370 (7)	−0.0117 (7)
N1	0.0601 (8)	0.0606 (8)	0.0454 (7)	−0.0058 (7)	0.0190 (6)	−0.0035 (6)
N2	0.0594 (8)	0.0600 (9)	0.0480 (7)	−0.0072 (7)	0.0209 (6)	−0.0032 (6)
C1	0.0765 (13)	0.0665 (11)	0.0675 (11)	−0.0158 (10)	0.0293 (10)	−0.0145 (9)
C2	0.0904 (15)	0.0796 (14)	0.0729 (12)	−0.0118 (12)	0.0365 (11)	−0.0235 (11)
C3	0.0722 (12)	0.0916 (15)	0.0594 (10)	0.0002 (11)	0.0290 (9)	−0.0038 (11)
C4	0.0714 (12)	0.0818 (14)	0.0608 (10)	−0.0133 (10)	0.0265 (9)	0.0047 (10)
C5	0.0723 (11)	0.0609 (10)	0.0549 (9)	−0.0121 (9)	0.0208 (8)	−0.0040 (8)
C6	0.0554 (9)	0.0571 (9)	0.0451 (8)	−0.0038 (7)	0.0137 (7)	−0.0010 (7)
C7	0.0578 (9)	0.0527 (9)	0.0444 (7)	−0.0030 (7)	0.0141 (7)	0.0019 (7)
C8	0.0608 (10)	0.0531 (9)	0.0523 (8)	−0.0054 (8)	0.0191 (7)	−0.0029 (7)
C9	0.0677 (12)	0.0984 (16)	0.0666 (12)	−0.0119 (12)	0.0111 (10)	0.0101 (12)
C10	0.0685 (14)	0.119 (2)	0.107 (2)	−0.0174 (15)	0.0096 (14)	−0.0027 (18)
C11	0.0759 (18)	0.097 (2)	0.186 (4)	−0.0279 (16)	0.041 (2)	−0.009 (2)
C12	0.117 (2)	0.0794 (18)	0.161 (3)	−0.0208 (17)	0.053 (2)	0.0344 (19)
C13	0.0860 (15)	0.0677 (13)	0.0986 (17)	−0.0073 (12)	0.0246 (13)	0.0253 (12)
C14	0.0610 (10)	0.0638 (10)	0.0482 (8)	−0.0086 (8)	0.0173 (7)	−0.0043 (7)
C15	0.0587 (9)	0.0567 (9)	0.0482 (8)	−0.0067 (8)	0.0164 (7)	−0.0020 (7)
C16	0.0616 (10)	0.0639 (10)	0.0457 (8)	−0.0021 (8)	0.0125 (7)	−0.0168 (8)
C17	0.0684 (12)	0.0996 (16)	0.0632 (11)	−0.0024 (12)	0.0217 (10)	−0.0067 (11)
C18	0.0626 (13)	0.138 (3)	0.0785 (15)	0.0057 (15)	0.0146 (11)	−0.0242 (17)
C19	0.0841 (16)	0.0917 (18)	0.0844 (16)	0.0213 (14)	−0.0124 (13)	−0.0338 (14)
C22	0.106 (2)	0.132 (3)	0.160 (3)	0.047 (2)	−0.027 (2)	−0.040 (3)
C20	0.0978 (19)	0.0686 (14)	0.107 (2)	0.0050 (13)	−0.0122 (16)	−0.0069 (13)
C21	0.0753 (13)	0.0665 (13)	0.0893 (15)	−0.0043 (11)	0.0075 (11)	−0.0036 (11)

S1—O1	1.4240 (15)	C10—C11	1.353 (5)
S1—O2	1.4341 (14)	C10—H10	0.9300
S1—N2	1.6336 (17)	C11—C12	1.372 (5)
S1—C16	1.752 (2)	C11—H11	0.9300
N1—C15	1.274 (2)	C12—C13	1.394 (4)
N1—N2	1.3969 (19)	C12—H12	0.9300
N2—H1N2	0.82 (2)	C13—H13	0.9300
C1—C6	1.388 (3)	C14—C15	1.448 (2)
C1—C2	1.395 (3)	C14—H14	0.9300
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.369 (3)	C16—C21	1.380 (3)
C2—H2	0.9300	C16—C17	1.381 (3)
C3—C4	1.373 (3)	C17—C18	1.387 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.387 (3)	C18—C19	1.368 (4)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.391 (2)	C19—C20	1.373 (4)
C5—H5	0.9300	C19—C22	1.516 (4)
C6—C7	1.486 (2)	C22—H22A	0.9600
C7—C14	1.343 (2)	C22—H22B	0.9600
C7—C8	1.495 (2)	C22—H22C	0.9600
C8—C13	1.376 (3)	C20—C21	1.380 (4)
C8—C9	1.385 (3)	C20—H20	0.9300
C9—C10	1.366 (3)	C21—H21	0.9300
C9—H9	0.9300
O1—S1—O2	119.94 (9)	C10—C11—C12	120.8 (3)
O1—S1—N2	108.18 (9)	C10—C11—H11	119.6
O2—S1—N2	103.87 (9)	C12—C11—H11	119.6
O1—S1—C16	108.48 (10)	C11—C12—C13	120.0 (3)
O2—S1—C16	108.97 (9)	C11—C12—H12	120.0
N2—S1—C16	106.60 (8)	C13—C12—H12	120.0
C15—N1—N2	115.26 (15)	C8—C13—C12	119.4 (3)
N1—N2—S1	113.54 (12)	C8—C13—H13	120.3
N1—N2—H1N2	115.6 (15)	C12—C13—H13	120.3
S1—N2—H1N2	113.8 (15)	C7—C14—C15	125.42 (17)
C6—C1—C2	120.84 (19)	C7—C14—H14	117.3
C6—C1—H1	119.6	C15—C14—H14	117.3
C2—C1—H1	119.6	N1—C15—C14	118.83 (16)
C3—C2—C1	120.5 (2)	N1—C15—H15	120.6
C3—C2—H2	119.8	C14—C15—H15	120.6
C1—C2—H2	119.8	C21—C16—C17	120.0 (2)
C2—C3—C4	119.55 (18)	C21—C16—S1	119.57 (16)
C2—C3—H3	120.2	C17—C16—S1	120.44 (18)
C4—C3—H3	120.2	C16—C17—C18	118.8 (3)
C3—C4—C5	120.34 (19)	C16—C17—H17	120.6
C3—C4—H4	119.8	C18—C17—H17	120.6
C5—C4—H4	119.8	C19—C18—C17	121.9 (3)
C4—C5—C6	121.15 (18)	C19—C18—H18	119.0
C4—C5—H5	119.4	C17—C18—H18	119.0
C6—C5—H5	119.4	C18—C19—C20	118.3 (2)
C1—C6—C5	117.65 (16)	C18—C19—C22	120.6 (3)
C1—C6—C7	119.93 (16)	C20—C19—C22	121.1 (3)
C5—C6—C7	122.42 (16)	C19—C22—H22A	109.5
C14—C7—C6	121.50 (16)	C19—C22—H22B	109.5
C14—C7—C8	121.27 (15)	H22A—C22—H22B	109.5
C6—C7—C8	117.23 (14)	C19—C22—H22C	109.5
C13—C8—C9	118.7 (2)	H22A—C22—H22C	109.5
C13—C8—C7	121.79 (19)	H22B—C22—H22C	109.5
C9—C8—C7	119.53 (17)	C19—C20—C21	121.3 (3)
C10—C9—C8	121.7 (2)	C19—C20—H20	119.3
C10—C9—H9	119.2	C21—C20—H20	119.3
C8—C9—H9	119.2	C16—C21—C20	119.7 (2)
C11—C10—C9	119.4 (3)	C16—C21—H21	120.1
C11—C10—H10	120.3	C20—C21—H21	120.1
C9—C10—H10	120.3

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2i	0.82 (2)	2.11 (2)	2.927 (2)	173 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2i	0.82 (2)	2.11 (2)	2.927 (2)	173 (2)

Symmetry code: (i) .