N'-[3-(Hy-droxy-imino)-butan-2-yl-idene]-4-methyl-benzene-1-sulfono-hydrazide.

In the title compound, C(11)H(15)N(3)O(3)S, the C-S-N(H)-N linkage is nonplanar, the torsion angle being 75.70 (12)°. The compound has two almost planar fragments linked to the S atom: the hydrazone-derivative fragment [(HONC(4)H(6))N-N(H)-] and the tolyl fragment (C(7)H(7)-) have maximum deviations from the mean plane through the non-H atoms of 0.0260 (10) and 0.0148 (14) Å, respectively. The two planar fragments make an inter-planar angle of 79.47 (5)°. In the crystal, mol-ecules are connected through inversion centers via pairs of N-H⋯O and O-H⋯N hydrogen bonds.

Related literature

For the synthesis and application of hy­droxy­imino-tosyl­hydrazones as complexing agents, see: Beger et al. (1991 ▶). For a similar structure with a tosyl­hydrazone derivative, see: Fonseca et al. (2011 ▶).

Experimental

Crystal data

C11H15N3O3S

M = 269.32

Triclinic,

a = 5.5740 (1) Å

b = 10.4354 (2) Å

c = 11.3997 (2) Å

α = 83.586 (1)°

β = 77.453 (1)°

γ = 87.688 (1)°

V = 643.11 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.55 × 0.24 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.872, T max = 0.946

11000 measured reflections

3211 independent reflections

2862 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.112

S = 1.05

3211 reflections

174 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.28 e Å−3

Data collection: COSMO (Bruker, 2005 ▶); cell refinement: SAINT; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812003339/fy2042sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003339/fy2042Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003339/fy2042Isup3.cml

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

C11H15N3O3S	Z = 2
Mr = 269.32	F(000) = 284
Triclinic, P1	Dx = 1.391 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5740 (1) Å	Cell parameters from 6049 reflections
b = 10.4354 (2) Å	θ = 2.6–28.3°
c = 11.3997 (2) Å	µ = 0.26 mm−1
α = 83.586 (1)°	T = 293 K
β = 77.453 (1)°	Block, colourless
γ = 87.688 (1)°	0.55 × 0.24 × 0.22 mm
V = 643.11 (2) Å3

Bruker APEXII CCD diffractometer	3211 independent reflections
Radiation source: fine-focus sealed tube, Bruker X8 APEXII	2862 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
φ and ω scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→6
Tmin = 0.872, Tmax = 0.946	k = −13→13
11000 measured reflections	l = −15→15

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0651P)2 + 0.1526P] where P = (Fo2 + 2Fc2)/3
3211 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.28 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	0.94931 (6)	0.06163 (3)	0.19318 (3)	0.03670 (12)
O3	1.14412 (19)	−0.00383 (11)	0.11725 (10)	0.0465 (3)
O1	0.0184 (2)	0.53370 (13)	0.13328 (14)	0.0599 (3)
O2	1.00547 (19)	0.14436 (11)	0.27426 (10)	0.0474 (3)
N3	0.8101 (2)	0.14880 (12)	0.09796 (12)	0.0410 (3)
N2	0.6390 (2)	0.23836 (11)	0.14677 (11)	0.0383 (3)
N1	0.1759 (2)	0.44076 (12)	0.07432 (12)	0.0446 (3)
C3	0.4937 (2)	0.28939 (12)	0.08064 (12)	0.0361 (3)
C5	0.7414 (2)	−0.05473 (13)	0.27630 (13)	0.0377 (3)
C2	0.3235 (2)	0.38812 (13)	0.13806 (13)	0.0393 (3)
C8	0.4212 (3)	−0.23753 (16)	0.41661 (14)	0.0489 (4)
C6	0.8088 (3)	−0.18421 (15)	0.28051 (16)	0.0493 (4)
H9	0.9602	−0.2102	0.2366	0.059*
C9	0.3564 (3)	−0.10782 (18)	0.40921 (16)	0.0546 (4)
H11	0.2030	−0.0821	0.4513	0.066*
C10	0.5143 (3)	−0.01583 (16)	0.34077 (16)	0.0502 (4)
H12	0.4691	0.0710	0.3379	0.060*
C4	0.4871 (3)	0.25726 (17)	−0.04261 (15)	0.0496 (4)
H5	0.4554	0.1671	−0.0395	0.074*
H6	0.6424	0.2770	−0.0962	0.074*
H7	0.3591	0.3070	−0.0716	0.074*
C7	0.6482 (3)	−0.27425 (16)	0.35074 (17)	0.0554 (4)
H10	0.6934	−0.3611	0.3539	0.066*
C11	0.2476 (4)	−0.3351 (2)	0.49484 (18)	0.0665 (5)
H13	0.0895	−0.3248	0.4741	0.100*
H14	0.2317	−0.3220	0.5782	0.100*
H15	0.3110	−0.4205	0.4820	0.100*
C1	0.3317 (3)	0.41963 (17)	0.26113 (15)	0.0539 (4)
H2	0.1975	0.4771	0.2887	0.081*
H3	0.4844	0.4604	0.2586	0.081*
H4	0.3186	0.3418	0.3155	0.081*
H8	0.794 (4)	0.1114 (19)	0.0409 (19)	0.053 (5)*
H1	−0.061 (5)	0.556 (2)	0.079 (2)	0.082 (8)*

	U11	U22	U33	U12	U13	U23
S1	0.03284 (18)	0.03859 (19)	0.0401 (2)	0.00890 (12)	−0.01154 (13)	−0.00617 (13)
O3	0.0385 (5)	0.0504 (6)	0.0492 (6)	0.0159 (4)	−0.0088 (4)	−0.0071 (5)
O1	0.0532 (7)	0.0575 (7)	0.0732 (8)	0.0290 (6)	−0.0195 (6)	−0.0236 (6)
O2	0.0453 (5)	0.0482 (6)	0.0538 (6)	0.0033 (4)	−0.0191 (5)	−0.0124 (5)
N3	0.0415 (6)	0.0419 (6)	0.0407 (6)	0.0153 (5)	−0.0128 (5)	−0.0067 (5)
N2	0.0352 (5)	0.0364 (6)	0.0425 (6)	0.0083 (4)	−0.0080 (5)	−0.0040 (5)
N1	0.0374 (6)	0.0396 (6)	0.0567 (8)	0.0137 (5)	−0.0106 (5)	−0.0093 (5)
C3	0.0323 (6)	0.0333 (6)	0.0412 (7)	0.0042 (5)	−0.0067 (5)	−0.0015 (5)
C5	0.0373 (6)	0.0396 (7)	0.0382 (7)	0.0059 (5)	−0.0133 (5)	−0.0053 (5)
C2	0.0347 (6)	0.0357 (6)	0.0461 (7)	0.0045 (5)	−0.0064 (5)	−0.0045 (6)
C8	0.0541 (8)	0.0520 (9)	0.0427 (8)	−0.0057 (7)	−0.0148 (6)	−0.0042 (7)
C6	0.0467 (8)	0.0431 (8)	0.0566 (9)	0.0095 (6)	−0.0073 (7)	−0.0096 (7)
C9	0.0450 (8)	0.0599 (10)	0.0548 (9)	0.0056 (7)	−0.0030 (7)	−0.0059 (8)
C10	0.0460 (8)	0.0444 (8)	0.0568 (9)	0.0110 (6)	−0.0060 (7)	−0.0041 (7)
C4	0.0522 (8)	0.0521 (9)	0.0457 (8)	0.0189 (7)	−0.0145 (7)	−0.0094 (7)
C7	0.0620 (10)	0.0392 (8)	0.0640 (10)	0.0038 (7)	−0.0123 (8)	−0.0053 (7)
C11	0.0719 (12)	0.0650 (11)	0.0590 (11)	−0.0142 (9)	−0.0079 (9)	0.0007 (9)
C1	0.0585 (9)	0.0545 (9)	0.0503 (9)	0.0140 (7)	−0.0129 (7)	−0.0153 (7)

S1—O2	1.4225 (11)	C8—C11	1.506 (2)
S1—O3	1.4349 (10)	C6—C7	1.383 (2)
S1—N3	1.6420 (12)	C6—H9	0.9300
S1—C5	1.7591 (14)	C9—C10	1.381 (2)
O1—N1	1.4084 (16)	C9—H11	0.9300
O1—H1	0.84 (3)	C10—H12	0.9300
N3—N2	1.3807 (16)	C4—H5	0.9600
N3—H8	0.82 (2)	C4—H6	0.9600
N2—C3	1.2843 (18)	C4—H7	0.9600
N1—C2	1.2808 (19)	C7—H10	0.9300
C3—C2	1.4806 (18)	C11—H13	0.9600
C3—C4	1.489 (2)	C11—H14	0.9600
C5—C6	1.386 (2)	C11—H15	0.9600
C5—C10	1.389 (2)	C1—H2	0.9600
C2—C1	1.487 (2)	C1—H3	0.9600
C8—C9	1.385 (2)	C1—H4	0.9600
C8—C7	1.387 (2)
O2—S1—O3	119.84 (7)	C10—C9—C8	121.49 (15)
O2—S1—N3	107.87 (7)	C10—C9—H11	119.3
O3—S1—N3	104.20 (6)	C8—C9—H11	119.3
O2—S1—C5	108.48 (7)	C9—C10—C5	119.14 (15)
O3—S1—C5	108.09 (7)	C9—C10—H12	120.4
N3—S1—C5	107.77 (6)	C5—C10—H12	120.4
N1—O1—H1	98.5 (17)	C3—C4—H5	109.5
N2—N3—S1	116.06 (10)	C3—C4—H6	109.5
N2—N3—H8	122.1 (14)	H5—C4—H6	109.5
S1—N3—H8	113.8 (14)	C3—C4—H7	109.5
C3—N2—N3	117.27 (12)	H5—C4—H7	109.5
C2—N1—O1	112.69 (13)	H6—C4—H7	109.5
N2—C3—C2	113.63 (13)	C6—C7—C8	121.31 (15)
N2—C3—C4	125.81 (13)	C6—C7—H10	119.3
C2—C3—C4	120.56 (12)	C8—C7—H10	119.3
C6—C5—C10	120.45 (14)	C8—C11—H13	109.5
C6—C5—S1	119.79 (11)	C8—C11—H14	109.5
C10—C5—S1	119.72 (11)	H13—C11—H14	109.5
N1—C2—C3	115.11 (13)	C8—C11—H15	109.5
N1—C2—C1	124.73 (13)	H13—C11—H15	109.5
C3—C2—C1	120.15 (12)	H14—C11—H15	109.5
C9—C8—C7	118.35 (15)	C2—C1—H2	109.5
C9—C8—C11	120.18 (16)	C2—C1—H3	109.5
C7—C8—C11	121.47 (16)	H2—C1—H3	109.5
C7—C6—C5	119.24 (15)	C2—C1—H4	109.5
C7—C6—H9	120.4	H2—C1—H4	109.5
C5—C6—H9	120.4	H3—C1—H4	109.5
O2—S1—N3—N2	−41.25 (12)	N2—C3—C2—N1	−179.95 (12)
O3—S1—N3—N2	−169.63 (10)	C4—C3—C2—N1	0.2 (2)
C5—S1—N3—N2	75.70 (12)	N2—C3—C2—C1	0.0 (2)
S1—N3—N2—C3	−166.53 (10)	C4—C3—C2—C1	−179.93 (15)
N3—N2—C3—C2	−177.60 (11)	C10—C5—C6—C7	−0.7 (2)
N3—N2—C3—C4	2.3 (2)	S1—C5—C6—C7	176.99 (13)
O2—S1—C5—C6	−117.69 (13)	C7—C8—C9—C10	−1.6 (3)
O3—S1—C5—C6	13.69 (15)	C11—C8—C9—C10	178.28 (17)
N3—S1—C5—C6	125.76 (13)	C8—C9—C10—C5	1.1 (3)
O2—S1—C5—C10	60.01 (14)	C6—C5—C10—C9	0.0 (2)
O3—S1—C5—C10	−168.61 (12)	S1—C5—C10—C9	−177.65 (13)
N3—S1—C5—C10	−56.54 (14)	C5—C6—C7—C8	0.2 (3)
O1—N1—C2—C3	179.96 (12)	C9—C8—C7—C6	0.9 (3)
O1—N1—C2—C1	0.1 (2)	C11—C8—C7—C6	−178.96 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H8···O3i	0.82 (2)	2.19 (2)	2.9830 (18)	165.0 (19)
O1—H1···N1ii	0.84 (3)	1.99 (3)	2.792 (2)	160 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H8⋯O3i	0.82 (2)	2.19 (2)	2.9830 (18)	165.0 (19)
O1—H1⋯N1ii	0.84 (3)	1.99 (3)	2.792 (2)	160 (2)

Symmetry codes: (i) ; (ii) .