(E)-N′-[1-(4-Chloro­phen­yl)ethyl­idene]-2-hydroxy­benzohydrazide

Abstract

In the title compound, C₁₅H₁₃ClN₂O₂, the dihedral angle between the two benzene rings is 7.0 (1)°. An intra­molecular N—H⋯O hydrogen bond is present and inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into chains along [001].

Related literature

For related literature, see: Sumita et al. (1999 ▶). For the crystal structure of the closely related compound (E)-2-hydr­oxy-N′-(2-naphthyl­methyl­ene)benzohydrazide, see: Qiu et al. (2006 ▶).

Experimental

Crystal data

• C₁₅H₁₃ClN₂O₂

• M _r = 288.72

• Monoclinic,

• a = 27.900 (3) Å

• b = 7.880 (1) Å

• c = 13.4899 (15) Å

• β = 113.530 (2)°

• V = 2719.2 (5) ų

• Z = 8

• Mo Kα radiation

• μ = 0.28 mm⁻¹

• T = 293 (2) K

• 0.35 × 0.17 × 0.07 mm

Data collection

• Bruker SMART CCD diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.907, T _max = 0.980

• 4744 measured reflections

• 1663 independent reflections

• 901 reflections with I > 2σ(I)

• R _int = 0.082

• θ_max = 22.0°

Refinement

• R[F ² > 2σ(F ²)] = 0.065

• wR(F ²) = 0.266

• S = 0.96

• 1663 reflections

• 182 parameters

• H-atom parameters constrained

• Δρ_max = 0.33 e Å⁻³

• Δρ_min = −0.37 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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.

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	1.96	2.645 (6)	135
O2—H2⋯O1i	0.82	1.92	2.676 (6)	153

Symmetry code: (i) .

supplementary crystallographic information

Comment

Salicyloyl hydrazide is an important organic intermediate, which can act as moulding board in inorganic complexes (Sumita et al., 1999). The title compound was obtained by reaction of salicyloyl hydrazide and 1-(4-chlorophenyl)ethanone. The bond lengths and angles are normal and comparable to those in the previously reported compound (E)-2-hydroxy-N'-(2-naphthylmethylene)-benzohydrazide (Qiu et al., 2006).

In the crystal structure, typical intramolecular N—H···O hydrogen bonds exist, and intermolecular O—H···O hydrogen bonds link the molecules into one-dimensional chains along [001].

Experimental

Salicyloyl hydrazide (0.3 mmol) and freshly prepared 1-(4-chlorophenyl)ethanone (0.3 mmol) were mixed in a 50 ml flask. After stirring for 30 min at 353 K, the mixture was cooled slowly to room temperature and the product was recrystallized from ethanol, affording the title compound as a green crystalline solid. Elemental analysis calculated: C 62.40, H 4.54, N 9.70%; found: C 62.58, H 4.45, N 9.64%.

Refinement

All H atoms were placed in geometrically idealized positions (N—H = 0.86, O—H = 0.82 and C—H = 0.93–0.96 Å) and refined as riding with U_iso(H) = 1.2 U_eq(C,O,N). Diffraction was relatively weak and the data are truncated to 0.95 Å resolution, with 901 of 1663 unique reflections (ca 54%) observed. As a consequence, the refined structure is of relatively low precision.

Figures

Fig. 1.

Molecular structure with displacement ellipsoids drawn at 30% probability for non-H atoms.

Crystal data

C15H13ClN2O2	F(000) = 1200
Mr = 288.72	Dx = 1.411 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 951 reflections
a = 27.900 (3) Å	θ = 2.7–25.1°
b = 7.880 (1) Å	µ = 0.28 mm−1
c = 13.4899 (15) Å	T = 293 K
β = 113.530 (2)°	Block, green
V = 2719.2 (5) Å3	0.35 × 0.17 × 0.07 mm
Z = 8

Data collection

Bruker SMART CCD diffractometer	1663 independent reflections
Radiation source: fine-focus sealed tube	901 reflections with I > 2σ(I)
graphite	Rint = 0.082
φ and ω scans	θmax = 22.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −29→20
Tmin = 0.907, Tmax = 0.980	k = −8→8
4744 measured reflections	l = −14→14

Refinement

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) = 0.266	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.1726P)2] where P = (Fo2 + 2Fc2)/3
1663 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

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
Cl1	−0.16974 (8)	0.5453 (3)	−0.40292 (16)	0.0745 (9)
N1	0.07264 (19)	0.1148 (7)	0.0780 (4)	0.0390 (15)
H1	0.0712	0.1193	0.1404	0.047*
N2	0.0332 (2)	0.1842 (7)	−0.0112 (4)	0.0372 (15)
O1	0.11636 (19)	0.0271 (8)	−0.0221 (4)	0.0714 (19)
O2	0.11905 (18)	0.0618 (6)	0.2888 (3)	0.0531 (15)
H2	0.1252	0.0612	0.3535	0.080*
C1	0.1133 (2)	0.0401 (10)	0.0666 (5)	0.0422 (19)
C2	0.1557 (2)	−0.0358 (9)	0.1654 (5)	0.0400 (18)
C3	0.1585 (2)	−0.0201 (9)	0.2719 (5)	0.0405 (19)
C4	0.2007 (3)	−0.0898 (10)	0.3581 (5)	0.050 (2)
H4	0.2027	−0.0789	0.4283	0.060*
C5	0.2391 (3)	−0.1741 (11)	0.3394 (6)	0.063 (2)
H5	0.2671	−0.2198	0.3975	0.075*
C6	0.2372 (3)	−0.1928 (11)	0.2365 (6)	0.060 (2)
H6	0.2627	−0.2543	0.2242	0.071*
C7	0.1960 (3)	−0.1174 (9)	0.1511 (6)	0.0457 (19)
H7	0.1958	−0.1225	0.0820	0.055*
C8	−0.0107 (3)	0.2598 (11)	0.1122 (5)	0.056 (2)
H8A	−0.0043	0.1505	0.1465	0.084*
H8B	−0.0452	0.2971	0.1005	0.084*
H8C	0.0145	0.3397	0.1578	0.084*
C9	−0.0057 (2)	0.2471 (9)	0.0044 (5)	0.0405 (18)
C10	−0.0473 (3)	0.3259 (9)	−0.0938 (5)	0.0387 (18)
C11	−0.0867 (3)	0.4294 (9)	−0.0915 (5)	0.046 (2)
H11	−0.0883	0.4545	−0.0254	0.055*
C12	−0.1242 (3)	0.4970 (10)	−0.1857 (6)	0.052 (2)
H12	−0.1503	0.5674	−0.1824	0.063*
C13	−0.1227 (3)	0.4592 (9)	−0.2842 (5)	0.0430 (19)
C14	−0.0845 (3)	0.3575 (10)	−0.2901 (5)	0.052 (2)
H14	−0.0827	0.3366	−0.3563	0.062*
C15	−0.0479 (3)	0.2847 (9)	−0.1954 (5)	0.0450 (19)
H15	−0.0236	0.2077	−0.2001	0.054*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Cl1	0.0664 (15)	0.088 (2)	0.0516 (14)	0.0085 (12)	0.0054 (11)	0.0142 (12)
N1	0.039 (3)	0.058 (4)	0.023 (3)	0.000 (3)	0.016 (3)	0.002 (3)
N2	0.038 (3)	0.043 (4)	0.032 (3)	−0.001 (3)	0.016 (3)	0.001 (3)
O1	0.061 (3)	0.136 (6)	0.026 (3)	0.018 (3)	0.027 (3)	0.006 (3)
O2	0.062 (3)	0.078 (4)	0.025 (2)	0.006 (3)	0.023 (2)	0.005 (2)
C1	0.038 (4)	0.065 (5)	0.028 (4)	−0.011 (4)	0.018 (3)	−0.006 (3)
C2	0.036 (4)	0.060 (5)	0.028 (4)	−0.007 (4)	0.016 (3)	0.003 (3)
C3	0.038 (4)	0.053 (5)	0.036 (4)	−0.003 (3)	0.020 (3)	0.002 (3)
C4	0.057 (5)	0.053 (6)	0.034 (4)	−0.007 (4)	0.013 (4)	0.006 (4)
C5	0.045 (5)	0.084 (7)	0.054 (5)	0.009 (4)	0.014 (4)	0.015 (5)
C6	0.040 (5)	0.084 (7)	0.055 (5)	0.006 (4)	0.019 (4)	0.008 (5)
C7	0.051 (5)	0.046 (5)	0.047 (4)	−0.001 (4)	0.027 (4)	−0.004 (4)
C8	0.056 (5)	0.080 (7)	0.037 (4)	−0.001 (4)	0.025 (4)	0.006 (4)
C9	0.042 (4)	0.049 (5)	0.033 (4)	−0.013 (4)	0.018 (3)	−0.007 (3)
C10	0.042 (4)	0.050 (5)	0.028 (4)	−0.008 (4)	0.019 (3)	0.000 (3)
C11	0.044 (4)	0.059 (6)	0.038 (4)	0.001 (4)	0.020 (4)	−0.007 (4)
C12	0.048 (5)	0.057 (6)	0.052 (5)	0.003 (4)	0.021 (4)	0.006 (4)
C13	0.037 (4)	0.041 (5)	0.042 (4)	−0.005 (4)	0.006 (3)	0.006 (4)
C14	0.060 (5)	0.064 (6)	0.033 (4)	−0.003 (4)	0.021 (4)	0.002 (4)
C15	0.042 (4)	0.061 (6)	0.035 (4)	0.008 (4)	0.019 (3)	0.002 (4)

Geometric parameters (Å, °)

Cl1—C13	1.752 (7)	C6—H6	0.930
N1—C1	1.340 (8)	C7—H7	0.930
N1—N2	1.379 (7)	C8—C9	1.518 (8)
N1—H1	0.860	C8—H8A	0.960
N2—C9	1.284 (8)	C8—H8B	0.960
O1—C1	1.237 (7)	C8—H8C	0.960
O2—C3	1.372 (8)	C9—C10	1.503 (9)
O2—H2	0.820	C10—C11	1.380 (9)
C1—C2	1.508 (9)	C10—C15	1.403 (8)
C2—C7	1.374 (9)	C11—C12	1.390 (9)
C2—C3	1.412 (9)	C11—H11	0.930
C3—C4	1.395 (9)	C12—C13	1.379 (10)
C4—C5	1.367 (10)	C12—H12	0.930
C4—H4	0.930	C13—C14	1.361 (10)
C5—C6	1.375 (10)	C14—C15	1.400 (9)
C5—H5	0.930	C14—H14	0.930
C6—C7	1.395 (9)	C15—H15	0.930
C1—N1—N2	119.4 (5)	C9—C8—H8B	109.5
C1—N1—H1	120.3	H8A—C8—H8B	109.5
N2—N1—H1	120.3	C9—C8—H8C	109.5
C9—N2—N1	116.2 (5)	H8A—C8—H8C	109.5
C3—O2—H2	109.5	H8B—C8—H8C	109.5
O1—C1—N1	122.4 (6)	N2—C9—C10	114.8 (5)
O1—C1—C2	119.3 (6)	N2—C9—C8	126.1 (6)
N1—C1—C2	118.3 (5)	C10—C9—C8	118.9 (6)
C7—C2—C3	117.8 (6)	C11—C10—C15	117.4 (6)
C7—C2—C1	117.3 (5)	C11—C10—C9	124.5 (5)
C3—C2—C1	124.8 (6)	C15—C10—C9	118.0 (6)
O2—C3—C4	120.8 (6)	C10—C11—C12	121.4 (6)
O2—C3—C2	119.2 (6)	C10—C11—H11	119.3
C4—C3—C2	120.0 (6)	C12—C11—H11	119.3
C5—C4—C3	120.0 (6)	C13—C12—C11	119.8 (7)
C5—C4—H4	120.0	C13—C12—H12	120.1
C3—C4—H4	120.0	C11—C12—H12	120.1
C4—C5—C6	121.3 (7)	C14—C13—C12	120.7 (6)
C4—C5—H5	119.3	C14—C13—Cl1	119.6 (5)
C6—C5—H5	119.3	C12—C13—Cl1	119.8 (6)
C5—C6—C7	118.4 (7)	C13—C14—C15	119.4 (6)
C5—C6—H6	120.8	C13—C14—H14	120.3
C7—C6—H6	120.8	C15—C14—H14	120.3
C2—C7—C6	122.3 (6)	C14—C15—C10	121.1 (7)
C2—C7—H7	118.8	C14—C15—H15	119.4
C6—C7—H7	118.8	C10—C15—H15	119.4
C9—C8—H8A	109.5

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.96	2.645 (6)	135
O2—H2···O1i	0.82	1.92	2.676 (6)	153

Symmetry codes: (i) x, −y, z+1/2.