N′-[1-(2-Hydroxy­phen­yl)ethyl­idene]benzene­sulfonohydrazide

In the title compound, C₁₄H₁₄N₂O₃S, the conformation is stabilized by an intra­moleclar O—H...N hydrogen bond and the dihedral angle between the aromatic ring planes is 79.55 (18)°. In the crystal structure, inter­molecular N—H...O hydrogen bonds lead to [100] chains of mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.048
• wR factor = 0.132
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

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Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.83 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

As part of our ongoing studies of the coordination chemistry of aroylhydrazones as potential ligands (Tai et al., 2003), we now report the synthesis and structure of the title compound, (I), (Fig. 1).

The molecular conformation is stabilised by an intramoleclar O-H···N hydrogen bond (Table 1) and the dihedral angle between the aromatic ring planes is 79.55 (18)°. In the crystal, an intermolecular N-H···O hydrogen bond lead to [100] chains of molecules.

Related literature

For related literature, see: Tai et al. (2003).

S2. Experimental

3 mmol of 2'-hydroxyacetophenone (3 mmol) was added to a solution of benzenesulfonyl hydrazide (3 mmol) in 10 ml of 95% ethanol. The mixture was continuously stirred for 3 h at refluxing temperature, evaporating some ethanol, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 68%). Colourless blocks of (I) were obtained by evaporation from a methanol solution after 3 days.

S3. Refinement

The H atoms were placed geometrically (C—H = 0.93–0.96 Å, O—H = 0.82Å, N—H = 0.90 Å) and refined as riding with U_iso(H) = 1.2U_eq(carrier) or 1.5U_eq(methyl C).

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008).

Figures

Fig. 1. The molecular structure of (I) showing 40% displacement ellipsoids (arbitrary spheres for the H atoms). The hydrogen bond is indicated by a double-dashed line.

N'-[1-(2-Hydroxyphenyl)ethylidene]benzenesulfonohydrazide

Crystal data

C14H14N2O3S	F(000) = 608
Mr = 290.33	Dx = 1.362 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2187 reflections
a = 5.2435 (9) Å	θ = 2.5–26.2°
b = 13.2515 (18) Å	µ = 0.24 mm^−1
c = 20.375 (2) Å	T = 298 K
β = 90.531 (2)°	Block, colourless
V = 1415.7 (3) Å^3	0.50 × 0.40 × 0.37 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	2484 independent reflections
Radiation source: fine-focus sealed tube	1755 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −6→6
Tmin = 0.891, Tmax = 0.918	k = −15→15
7165 measured reflections	l = −20→24

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.0428P)^2 + 0.8643P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2484 reflections	Δρmax = 0.26 e Å^−3
182 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.3921 (4)	0.13317 (15)	0.94596 (10)	0.0397 (6)
H1	0.5569	0.1345	0.9587	0.048*
N2	0.3516 (4)	0.21056 (16)	0.90070 (10)	0.0378 (5)
O1	0.2888 (4)	0.06000 (14)	1.05125 (9)	0.0589 (6)
O2	−0.0427 (4)	0.15363 (16)	0.98874 (10)	0.0560 (6)
O3	0.0643 (4)	0.35673 (15)	0.86405 (10)	0.0590 (6)
H3	0.1123	0.3112	0.8884	0.089*
S1	0.21361 (14)	0.14329 (5)	1.01133 (3)	0.0403 (3)
C1	0.2935 (5)	0.2560 (2)	1.05229 (13)	0.0414 (7)
C2	0.1465 (7)	0.3404 (2)	1.04223 (18)	0.0659 (10)
H2	0.0090	0.3388	1.0131	0.079*
C3	0.2063 (10)	0.4282 (3)	1.0763 (2)	0.0931 (14)
H3A	0.1108	0.4864	1.0694	0.112*
C4	0.4057 (10)	0.4288 (4)	1.1200 (3)	0.1013 (16)
H4	0.4428	0.4871	1.1436	0.122*
C5	0.5504 (8)	0.3446 (4)	1.1293 (2)	0.0922 (14)
H5	0.6876	0.3463	1.1586	0.111*
C6	0.4952 (6)	0.2567 (3)	1.09574 (17)	0.0651 (9)
H6	0.5928	0.1990	1.1024	0.078*
C7	0.6988 (6)	0.1407 (2)	0.83455 (14)	0.0472 (7)
H7A	0.8593	0.1693	0.8479	0.071*
H7B	0.7018	0.1265	0.7884	0.071*
H7C	0.6699	0.0793	0.8584	0.071*
C8	0.4892 (5)	0.21397 (19)	0.84856 (12)	0.0357 (6)
C9	0.4232 (5)	0.29502 (19)	0.80152 (12)	0.0381 (6)
C10	0.2176 (5)	0.3608 (2)	0.81077 (13)	0.0421 (7)
C11	0.1611 (6)	0.4351 (2)	0.76493 (15)	0.0553 (8)
H11	0.0230	0.4779	0.7716	0.066*
C12	0.3072 (7)	0.4462 (3)	0.70987 (16)	0.0619 (9)
H12	0.2675	0.4960	0.6793	0.074*
C13	0.5109 (7)	0.3840 (3)	0.70007 (15)	0.0631 (9)
H13	0.6118	0.3920	0.6631	0.076*
C14	0.5665 (6)	0.3096 (2)	0.74492 (14)	0.0524 (8)
H14	0.7047	0.2673	0.7373	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0424 (14)	0.0379 (12)	0.0388 (12)	0.0084 (10)	0.0018 (10)	0.0056 (10)
N2	0.0423 (13)	0.0336 (12)	0.0374 (12)	0.0046 (10)	−0.0001 (10)	0.0029 (10)
O1	0.0933 (17)	0.0375 (11)	0.0461 (12)	0.0088 (11)	0.0154 (11)	0.0074 (9)
O2	0.0413 (13)	0.0634 (14)	0.0636 (13)	−0.0068 (10)	0.0049 (10)	−0.0136 (11)
O3	0.0633 (15)	0.0536 (13)	0.0605 (13)	0.0217 (11)	0.0148 (11)	0.0146 (10)
S1	0.0473 (5)	0.0335 (4)	0.0402 (4)	0.0002 (3)	0.0065 (3)	−0.0006 (3)
C1	0.0423 (17)	0.0383 (15)	0.0436 (16)	−0.0023 (12)	0.0051 (13)	−0.0047 (12)
C2	0.081 (3)	0.0445 (19)	0.073 (2)	0.0108 (17)	−0.0073 (19)	−0.0115 (16)
C3	0.123 (4)	0.046 (2)	0.111 (3)	0.009 (2)	0.011 (3)	−0.022 (2)
C4	0.102 (4)	0.084 (3)	0.118 (4)	−0.034 (3)	0.012 (3)	−0.050 (3)
C5	0.069 (3)	0.114 (4)	0.094 (3)	−0.019 (3)	−0.012 (2)	−0.045 (3)
C6	0.048 (2)	0.074 (2)	0.073 (2)	0.0026 (17)	−0.0069 (18)	−0.0137 (18)
C7	0.0505 (19)	0.0457 (16)	0.0457 (16)	0.0071 (14)	0.0069 (14)	−0.0027 (13)
C8	0.0362 (15)	0.0342 (14)	0.0366 (14)	−0.0051 (12)	−0.0013 (12)	−0.0055 (11)
C9	0.0418 (17)	0.0361 (14)	0.0363 (14)	−0.0049 (12)	−0.0048 (12)	−0.0004 (11)
C10	0.0421 (17)	0.0400 (15)	0.0442 (16)	−0.0037 (13)	−0.0021 (13)	0.0025 (13)
C11	0.056 (2)	0.0466 (18)	0.063 (2)	0.0022 (15)	−0.0082 (16)	0.0154 (15)
C12	0.071 (2)	0.059 (2)	0.055 (2)	−0.0072 (18)	−0.0139 (18)	0.0214 (16)
C13	0.076 (3)	0.069 (2)	0.0450 (18)	−0.0073 (19)	0.0049 (17)	0.0140 (16)
C14	0.056 (2)	0.0562 (19)	0.0448 (17)	0.0011 (15)	0.0025 (15)	0.0065 (14)

Geometric parameters (Å, º)

N1—N2	1.394 (3)	C5—H5	0.9300
N1—S1	1.641 (2)	C6—H6	0.9300
N1—H1	0.9000	C7—C8	1.496 (4)
N2—C8	1.291 (3)	C7—H7A	0.9600
O1—S1	1.4246 (19)	C7—H7B	0.9600
O2—S1	1.423 (2)	C7—H7C	0.9600
O3—C10	1.358 (3)	C8—C9	1.478 (4)
O3—H3	0.8200	C9—C14	1.395 (4)
S1—C1	1.760 (3)	C9—C10	1.401 (4)
C1—C2	1.372 (4)	C10—C11	1.387 (4)
C1—C6	1.373 (4)	C11—C12	1.372 (4)
C2—C3	1.390 (5)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.366 (5)
C3—C4	1.367 (6)	C12—H12	0.9300
C3—H3A	0.9300	C13—C14	1.374 (4)
C4—C5	1.361 (6)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.380 (5)
N2—N1—S1	113.09 (16)	C5—C6—H6	120.6
N2—N1—H1	108.5	C8—C7—H7A	109.5
S1—N1—H1	108.5	C8—C7—H7B	109.5
C8—N2—N1	119.2 (2)	H7A—C7—H7B	109.5
C10—O3—H3	109.5	C8—C7—H7C	109.5
O2—S1—O1	120.99 (14)	H7A—C7—H7C	109.5
O2—S1—N1	106.82 (12)	H7B—C7—H7C	109.5
O1—S1—N1	104.08 (11)	N2—C8—C9	115.5 (2)
O2—S1—C1	106.95 (13)	N2—C8—C7	123.5 (2)
O1—S1—C1	108.88 (13)	C9—C8—C7	121.0 (2)
N1—S1—C1	108.63 (12)	C14—C9—C10	116.5 (2)
C2—C1—C6	121.3 (3)	C14—C9—C8	120.8 (2)
C2—C1—S1	119.3 (2)	C10—C9—C8	122.7 (2)
C6—C1—S1	119.3 (2)	O3—C10—C11	116.3 (3)
C1—C2—C3	118.9 (4)	O3—C10—C9	123.0 (2)
C1—C2—H2	120.5	C11—C10—C9	120.7 (3)
C3—C2—H2	120.5	C12—C11—C10	120.6 (3)
C4—C3—C2	119.9 (4)	C12—C11—H11	119.7
C4—C3—H3A	120.1	C10—C11—H11	119.7
C2—C3—H3A	120.1	C13—C12—C11	119.9 (3)
C5—C4—C3	120.5 (4)	C13—C12—H12	120.1
C5—C4—H4	119.7	C11—C12—H12	120.1
C3—C4—H4	119.7	C12—C13—C14	119.8 (3)
C4—C5—C6	120.6 (4)	C12—C13—H13	120.1
C4—C5—H5	119.7	C14—C13—H13	120.1
C6—C5—H5	119.7	C13—C14—C9	122.4 (3)
C1—C6—C5	118.8 (4)	C13—C14—H14	118.8
C1—C6—H6	120.6	C9—C14—H14	118.8
S1—N1—N2—C8	176.68 (19)	N1—N2—C8—C9	176.6 (2)
N2—N1—S1—O2	52.5 (2)	N1—N2—C8—C7	−2.1 (4)
N2—N1—S1—O1	−178.43 (18)	N2—C8—C9—C14	176.8 (2)
N2—N1—S1—C1	−62.5 (2)	C7—C8—C9—C14	−4.5 (4)
O2—S1—C1—C2	−17.1 (3)	N2—C8—C9—C10	−3.1 (4)
O1—S1—C1—C2	−149.4 (3)	C7—C8—C9—C10	175.6 (3)
N1—S1—C1—C2	97.9 (3)	C14—C9—C10—O3	−178.9 (3)
O2—S1—C1—C6	160.2 (2)	C8—C9—C10—O3	1.0 (4)
O1—S1—C1—C6	27.9 (3)	C14—C9—C10—C11	0.8 (4)
N1—S1—C1—C6	−84.8 (3)	C8—C9—C10—C11	−179.3 (3)
C6—C1—C2—C3	0.8 (5)	O3—C10—C11—C12	179.1 (3)
S1—C1—C2—C3	178.0 (3)	C9—C10—C11—C12	−0.6 (5)
C1—C2—C3—C4	−1.3 (6)	C10—C11—C12—C13	−0.3 (5)
C2—C3—C4—C5	1.6 (7)	C11—C12—C13—C14	1.0 (5)
C3—C4—C5—C6	−1.3 (7)	C12—C13—C14—C9	−0.7 (5)
C2—C1—C6—C5	−0.5 (5)	C10—C9—C14—C13	−0.2 (4)
S1—C1—C6—C5	−177.7 (3)	C8—C9—C14—C13	180.0 (3)
C4—C5—C6—C1	0.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.82	1.85	2.561 (3)	145
N1—H1···O2^i	0.90	2.20	3.093 (3)	174

Symmetry code: (i) x+1, y, z.