1,2-Bis(p-tolyl-sulfon-yl)hydrazine.

In the title compound, C(14)H(16)N(2)O(4)S(2), the dihedral angle between the aromatic ring planes is 76.8 (3)° and the S-N-N-S torsion angle is 122.5 (3)°. In the crystal structure, mol-ecules form a chain structure by way of N-H⋯O hydrogen bonds.

Related literature

For background on aroylhydrazines, see: Bu et al. (2001 ▶); Ranford et al. (1998 ▶), Agarwal & Sharma (1993 ▶).

Experimental

Crystal data

C14H16N2O4S2

M = 340.41

Monoclinic,

a = 15.7318 (16) Å

b = 10.7016 (12) Å

c = 9.4943 (9) Å

β = 90.102 (2)°

V = 1598.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 298 (2) K

0.33 × 0.11 × 0.04 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.893, T max = 0.986

7984 measured reflections

2808 independent reflections

1132 reflections with I > 2σ(I)

R int = 0.108

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.080

S = 0.97

2808 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034314/hb2824sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034314/hb2824Isup2.hkl

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

C14H16N2O4S2	F(000) = 712
Mr = 340.41	Dx = 1.415 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 586 reflections
a = 15.7318 (16) Å	θ = 2.3–25.0°
b = 10.7016 (12) Å	µ = 0.35 mm−1
c = 9.4943 (9) Å	T = 298 K
β = 90.102 (2)°	Flake, colourless
V = 1598.4 (3) Å3	0.33 × 0.11 × 0.04 mm
Z = 4

Bruker SMART CCD diffractometer	2808 independent reflections
Radiation source: fine-focus sealed tube	1132 reflections with I > 2σ(I)
graphite	Rint = 0.108
ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −18→12
Tmin = 0.893, Tmax = 0.986	k = −12→12
7984 measured reflections	l = −11→11

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0003P)2] where P = (Fo2 + 2Fc2)/3
2808 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.27 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	0.82111 (9)	0.60680 (14)	−0.00482 (14)	0.0542 (4)
S2	0.70156 (9)	0.91574 (15)	−0.01299 (15)	0.0588 (4)
N1	0.7517 (2)	0.7008 (4)	0.0725 (4)	0.0513 (12)
H1	0.7484	0.6794	0.1640	0.062*
N2	0.7743 (2)	0.8278 (4)	0.0630 (4)	0.0535 (12)
H2A	0.7823	0.8571	0.1508	0.064*
O1	0.82411 (18)	0.6447 (3)	−0.1491 (3)	0.0628 (10)
O2	0.7938 (2)	0.4847 (3)	0.0334 (4)	0.0682 (11)
O3	0.6846 (2)	0.8623 (3)	−0.1482 (3)	0.0701 (11)
O4	0.7356 (2)	1.0395 (3)	−0.0015 (4)	0.0771 (13)
C1	0.9213 (3)	0.6382 (5)	0.0667 (5)	0.0446 (14)
C2	0.9673 (4)	0.7381 (5)	0.0188 (6)	0.0602 (17)
H2	0.9458	0.7892	−0.0520	0.072*
C3	1.0465 (4)	0.7620 (5)	0.0775 (6)	0.0634 (17)
H3	1.0772	0.8310	0.0467	0.076*
C4	1.0807 (3)	0.6865 (5)	0.1799 (6)	0.0534 (16)
C5	1.0339 (4)	0.5857 (5)	0.2236 (5)	0.0579 (15)
H5	1.0567	0.5327	0.2915	0.069*
C6	0.9547 (3)	0.5604 (5)	0.1703 (6)	0.0538 (15)
H6	0.9238	0.4923	0.2030	0.065*
C7	1.1679 (3)	0.7141 (5)	0.2376 (6)	0.080 (2)
H7A	1.1862	0.6461	0.2962	0.121*
H7B	1.1661	0.7895	0.2924	0.121*
H7C	1.2071	0.7245	0.1611	0.121*
C8	0.6086 (3)	0.9042 (5)	0.0880 (5)	0.0472 (14)
C9	0.6008 (4)	0.9722 (5)	0.2078 (6)	0.087 (2)
H9	0.6448	1.0240	0.2374	0.104*
C10	0.5265 (4)	0.9636 (6)	0.2860 (6)	0.095 (2)
H10	0.5214	1.0115	0.3673	0.115*
C11	0.4622 (4)	0.8893 (6)	0.2488 (6)	0.0659 (18)
C12	0.4712 (4)	0.8228 (5)	0.1302 (7)	0.087 (2)
H12	0.4274	0.7698	0.1025	0.104*
C13	0.5441 (4)	0.8306 (5)	0.0467 (6)	0.083 (2)
H13	0.5480	0.7851	−0.0365	0.100*
C14	0.3808 (3)	0.8797 (5)	0.3358 (6)	0.091 (2)
H14A	0.3852	0.9327	0.4170	0.136*
H14B	0.3727	0.7947	0.3654	0.136*
H14C	0.3332	0.9055	0.2794	0.136*

	U11	U22	U33	U12	U13	U23
S1	0.0498 (10)	0.0731 (11)	0.0398 (9)	0.0048 (9)	0.0043 (7)	−0.0049 (8)
S2	0.0622 (11)	0.0726 (11)	0.0417 (10)	0.0093 (10)	0.0038 (8)	0.0035 (9)
N1	0.052 (3)	0.068 (3)	0.034 (3)	0.010 (3)	0.004 (2)	0.002 (2)
N2	0.054 (3)	0.068 (3)	0.038 (3)	0.010 (3)	−0.001 (2)	−0.003 (3)
O1	0.058 (2)	0.099 (3)	0.031 (2)	0.011 (2)	0.0041 (17)	−0.007 (2)
O2	0.066 (3)	0.056 (2)	0.083 (3)	−0.009 (2)	0.003 (2)	−0.001 (2)
O3	0.073 (3)	0.104 (3)	0.033 (2)	0.021 (2)	0.0053 (19)	−0.004 (2)
O4	0.087 (3)	0.062 (2)	0.082 (3)	−0.014 (2)	0.012 (2)	0.010 (2)
C1	0.038 (3)	0.051 (4)	0.045 (4)	0.006 (3)	0.006 (3)	−0.005 (3)
C2	0.048 (4)	0.071 (4)	0.061 (4)	0.005 (4)	0.004 (3)	0.022 (3)
C3	0.048 (4)	0.076 (5)	0.066 (5)	−0.007 (4)	0.011 (3)	0.008 (4)
C4	0.051 (4)	0.058 (4)	0.051 (4)	0.007 (4)	−0.003 (3)	−0.013 (3)
C5	0.067 (4)	0.058 (4)	0.049 (4)	0.014 (4)	−0.012 (3)	0.002 (3)
C6	0.058 (4)	0.056 (4)	0.047 (4)	0.004 (3)	0.009 (3)	−0.001 (3)
C7	0.052 (4)	0.096 (5)	0.093 (6)	0.005 (4)	−0.012 (4)	−0.017 (4)
C8	0.049 (4)	0.055 (4)	0.038 (3)	0.006 (3)	−0.002 (3)	−0.003 (3)
C9	0.081 (5)	0.112 (5)	0.067 (5)	−0.030 (4)	0.015 (4)	−0.043 (4)
C10	0.094 (6)	0.124 (6)	0.069 (5)	−0.008 (5)	0.034 (4)	−0.042 (4)
C11	0.057 (4)	0.082 (5)	0.058 (4)	0.020 (4)	0.005 (4)	0.010 (4)
C12	0.057 (5)	0.112 (5)	0.092 (6)	−0.024 (4)	0.007 (4)	−0.029 (5)
C13	0.071 (5)	0.103 (5)	0.075 (5)	−0.003 (4)	0.001 (4)	−0.031 (4)
C14	0.068 (4)	0.132 (5)	0.072 (5)	0.026 (4)	0.017 (3)	0.020 (4)

S1—O2	1.423 (3)	C5—H5	0.9300
S1—O1	1.429 (3)	C6—H6	0.9300
S1—N1	1.657 (3)	C7—H7A	0.9600
S1—C1	1.748 (5)	C7—H7B	0.9600
S2—O3	1.430 (3)	C7—H7C	0.9600
S2—O4	1.433 (3)	C8—C13	1.343 (6)
S2—N2	1.648 (4)	C8—C9	1.356 (6)
S2—C8	1.754 (4)	C9—C10	1.389 (6)
N1—N2	1.407 (4)	C9—H9	0.9300
N1—H1	0.9001	C10—C11	1.333 (7)
N2—H2A	0.8998	C10—H10	0.9300
C1—C2	1.369 (6)	C11—C12	1.340 (7)
C1—C6	1.391 (6)	C11—C14	1.529 (6)
C2—C3	1.387 (7)	C12—C13	1.398 (6)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.373 (7)	C13—H13	0.9300
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.370 (6)	C14—H14B	0.9600
C4—C7	1.507 (6)	C14—H14C	0.9600
C5—C6	1.371 (6)
O2—S1—O1	121.0 (2)	C5—C6—C1	119.0 (5)
O2—S1—N1	104.1 (2)	C5—C6—H6	120.5
O1—S1—N1	106.0 (2)	C1—C6—H6	120.5
O2—S1—C1	110.5 (3)	C4—C7—H7A	109.5
O1—S1—C1	106.6 (2)	C4—C7—H7B	109.5
N1—S1—C1	107.8 (2)	H7A—C7—H7B	109.5
O3—S2—O4	120.5 (2)	C4—C7—H7C	109.5
O3—S2—N2	107.0 (2)	H7A—C7—H7C	109.5
O4—S2—N2	103.6 (2)	H7B—C7—H7C	109.5
O3—S2—C8	107.9 (2)	C13—C8—C9	119.3 (5)
O4—S2—C8	109.6 (2)	C13—C8—S2	120.8 (4)
N2—S2—C8	107.4 (2)	C9—C8—S2	119.8 (5)
N2—N1—S1	113.0 (3)	C8—C9—C10	119.4 (6)
N2—N1—H1	108.8	C8—C9—H9	120.3
S1—N1—H1	108.2	C10—C9—H9	120.3
N1—N2—S2	113.8 (3)	C11—C10—C9	122.5 (6)
N1—N2—H2A	108.2	C11—C10—H10	118.8
S2—N2—H2A	107.5	C9—C10—H10	118.8
C2—C1—C6	120.2 (5)	C10—C11—C12	117.3 (6)
C2—C1—S1	119.9 (5)	C10—C11—C14	122.2 (6)
C6—C1—S1	119.9 (4)	C12—C11—C14	120.5 (7)
C1—C2—C3	119.1 (5)	C11—C12—C13	122.2 (6)
C1—C2—H2	120.5	C11—C12—H12	118.9
C3—C2—H2	120.5	C13—C12—H12	118.9
C4—C3—C2	121.7 (5)	C8—C13—C12	119.3 (6)
C4—C3—H3	119.1	C8—C13—H13	120.3
C2—C3—H3	119.1	C12—C13—H13	120.3
C5—C4—C3	117.9 (6)	C11—C14—H14A	109.5
C5—C4—C7	122.2 (6)	C11—C14—H14B	109.5
C3—C4—C7	119.8 (6)	H14A—C14—H14B	109.5
C4—C5—C6	122.1 (5)	C11—C14—H14C	109.5
C4—C5—H5	119.0	H14A—C14—H14C	109.5
C6—C5—H5	119.0	H14B—C14—H14C	109.5
O2—S1—N1—N2	172.0 (3)	C4—C5—C6—C1	1.3 (8)
O1—S1—N1—N2	−59.3 (4)	C2—C1—C6—C5	0.2 (7)
C1—S1—N1—N2	54.6 (4)	S1—C1—C6—C5	179.1 (4)
S1—N1—N2—S2	122.5 (3)	O3—S2—C8—C13	13.6 (5)
O3—S2—N2—N1	−55.6 (3)	O4—S2—C8—C13	146.6 (4)
O4—S2—N2—N1	176.0 (3)	N2—S2—C8—C13	−101.5 (5)
C8—S2—N2—N1	60.1 (4)	O3—S2—C8—C9	−165.1 (4)
O2—S1—C1—C2	165.9 (4)	O4—S2—C8—C9	−32.1 (5)
O1—S1—C1—C2	32.5 (4)	N2—S2—C8—C9	79.8 (5)
N1—S1—C1—C2	−80.9 (4)	C13—C8—C9—C10	0.4 (9)
O2—S1—C1—C6	−13.1 (4)	S2—C8—C9—C10	179.1 (5)
O1—S1—C1—C6	−146.4 (4)	C8—C9—C10—C11	1.0 (10)
N1—S1—C1—C6	100.2 (4)	C9—C10—C11—C12	−0.9 (10)
C6—C1—C2—C3	−1.5 (8)	C9—C10—C11—C14	179.6 (6)
S1—C1—C2—C3	179.6 (4)	C10—C11—C12—C13	−0.5 (10)
C1—C2—C3—C4	1.5 (9)	C14—C11—C12—C13	179.0 (5)
C2—C3—C4—C5	−0.2 (8)	C9—C8—C13—C12	−1.7 (8)
C2—C3—C4—C7	178.3 (5)	S2—C8—C13—C12	179.5 (4)
C3—C4—C5—C6	−1.2 (8)	C11—C12—C13—C8	1.9 (9)
C7—C4—C5—C6	−179.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.90	2.10	2.935 (5)	155
N2—H2A···O1i	0.90	2.01	2.857 (5)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.90	2.10	2.935 (5)	155
N2—H2A⋯O1i	0.90	2.01	2.857 (5)	157

Symmetry code: (i) .