N'-(2-Hy-droxy-benzyl-idene)-3-methyl-benzohydrazide.

The title compound, C(15)H(14)N(2)O(2), is the product of the reaction of 2-hy-droxy-benzaldehyde and 3-methyl-benzo-hydrazide. The dihedral angle between the substituted benzene rings is 19.5 (3)° and an intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds to generate C(4) chains propagating in [001] and C-H⋯O inter-actions to the same O-atom acceptor reinforce the chains.

Related literature

For reference bond lengths, see: Allen et al. (1987 ▶). For related structues, see: Horkaew et al. (2011 ▶); Fun et al. (2011 ▶); Su et al. (2011 ▶); Hashemian et al. (2011 ▶); Promdet et al. (2011 ▶).

Experimental

Crystal data

C15H14N2O2

M = 254.28

Monoclinic,

a = 11.042 (2) Å

b = 13.588 (3) Å

c = 8.7936 (15) Å

β = 94.406 (2)°

V = 1315.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.17 × 0.17 × 0.15 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.985, T max = 0.987

9633 measured reflections

2686 independent reflections

1528 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.186

S = 1.04

2686 reflections

177 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811049944/hb6528sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049944/hb6528Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811049944/hb6528Isup3.cml

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

C15H14N2O2	F(000) = 536
Mr = 254.28	Dx = 1.284 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.042 (2) Å	Cell parameters from 1290 reflections
b = 13.588 (3) Å	θ = 2.4–24.5°
c = 8.7936 (15) Å	µ = 0.09 mm−1
β = 94.406 (2)°	T = 298 K
V = 1315.5 (4) Å3	Prism, colorless
Z = 4	0.17 × 0.17 × 0.15 mm

Bruker SMART 1K CCD diffractometer	2686 independent reflections
Radiation source: fine-focus sealed tube	1528 reflections with I > 2σ(I)
graphite	Rint = 0.052
ω scan	θmax = 26.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.985, Tmax = 0.987	k = −17→15
9633 measured reflections	l = −10→10

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0872P)2 + 0.1389P] where P = (Fo2 + 2Fc2)/3
2686 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.59 e Å−3
1 restraint	Δρmin = −0.24 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
N1	0.28488 (18)	0.65695 (15)	0.0597 (2)	0.0486 (5)
N2	0.22818 (19)	0.72924 (16)	−0.0306 (2)	0.0521 (6)
O1	0.42021 (18)	0.59365 (14)	0.2981 (2)	0.0661 (6)
H1	0.3787	0.6335	0.2473	0.099*
O2	0.22190 (17)	0.83426 (13)	0.16687 (18)	0.0610 (6)
C1	0.3578 (2)	0.49285 (18)	0.0816 (3)	0.0463 (6)
C2	0.4170 (2)	0.50626 (19)	0.2260 (3)	0.0488 (6)
C3	0.4770 (2)	0.4277 (2)	0.2997 (3)	0.0645 (8)
H3	0.5176	0.4367	0.3953	0.077*
C4	0.4765 (3)	0.3370 (2)	0.2314 (4)	0.0701 (9)
H4	0.5163	0.2846	0.2818	0.084*
C5	0.4180 (3)	0.3224 (2)	0.0897 (4)	0.0696 (8)
H5	0.4176	0.2605	0.0445	0.083*
C6	0.3600 (2)	0.39998 (19)	0.0152 (3)	0.0601 (7)
H6	0.3214	0.3903	−0.0814	0.072*
C7	0.2970 (2)	0.57306 (19)	−0.0011 (3)	0.0508 (6)
H7	0.2660	0.5630	−0.1013	0.061*
C8	0.2014 (2)	0.81577 (18)	0.0313 (3)	0.0457 (6)
C9	0.1440 (2)	0.89021 (19)	−0.0753 (3)	0.0471 (6)
C10	0.1681 (2)	0.98853 (19)	−0.0468 (3)	0.0549 (7)
H10	0.2194	1.0056	0.0379	0.066*
C11	0.1186 (2)	1.0620 (2)	−0.1397 (3)	0.0634 (8)
C12	0.0402 (3)	1.0358 (3)	−0.2601 (3)	0.0768 (10)
H12	0.0048	1.0844	−0.3233	0.092*
C13	0.0125 (3)	0.9383 (3)	−0.2897 (3)	0.0796 (10)
H13	−0.0418	0.9219	−0.3719	0.095*
C14	0.0652 (2)	0.8645 (2)	−0.1976 (3)	0.0617 (8)
H14	0.0476	0.7987	−0.2183	0.074*
C15	0.1510 (3)	1.1678 (2)	−0.1097 (5)	0.1026 (13)
H15A	0.1779	1.1969	−0.2006	0.154*
H15B	0.2148	1.1717	−0.0294	0.154*
H15C	0.0809	1.2025	−0.0798	0.154*
H2	0.226 (3)	0.718 (2)	−0.1311 (13)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0553 (12)	0.0510 (13)	0.0390 (12)	0.0021 (10)	0.0003 (9)	0.0082 (10)
N2	0.0706 (14)	0.0517 (13)	0.0332 (11)	0.0040 (11)	−0.0023 (10)	0.0029 (10)
O1	0.0816 (14)	0.0590 (13)	0.0556 (12)	0.0063 (10)	−0.0080 (10)	−0.0021 (10)
O2	0.0881 (13)	0.0607 (12)	0.0324 (10)	0.0018 (9)	−0.0064 (9)	−0.0003 (8)
C1	0.0501 (14)	0.0469 (15)	0.0427 (15)	−0.0014 (11)	0.0093 (11)	0.0031 (11)
C2	0.0543 (14)	0.0473 (16)	0.0455 (15)	0.0020 (12)	0.0085 (11)	0.0005 (12)
C3	0.0666 (18)	0.069 (2)	0.0576 (18)	0.0114 (15)	0.0015 (13)	0.0035 (15)
C4	0.0721 (19)	0.0573 (19)	0.082 (2)	0.0160 (15)	0.0138 (17)	0.0101 (17)
C5	0.0748 (19)	0.0540 (18)	0.082 (2)	0.0016 (15)	0.0173 (17)	−0.0099 (16)
C6	0.0688 (18)	0.0511 (17)	0.0603 (18)	−0.0028 (13)	0.0039 (14)	−0.0046 (14)
C7	0.0592 (15)	0.0535 (17)	0.0396 (14)	−0.0043 (12)	0.0029 (11)	−0.0007 (13)
C8	0.0514 (14)	0.0506 (16)	0.0345 (14)	−0.0042 (11)	−0.0006 (11)	0.0025 (12)
C9	0.0482 (14)	0.0589 (17)	0.0344 (13)	0.0035 (11)	0.0038 (10)	0.0039 (12)
C10	0.0514 (14)	0.0579 (17)	0.0555 (17)	0.0001 (12)	0.0045 (12)	0.0047 (14)
C11	0.0569 (16)	0.0629 (19)	0.072 (2)	0.0131 (14)	0.0162 (15)	0.0207 (15)
C12	0.081 (2)	0.090 (3)	0.060 (2)	0.0348 (19)	0.0108 (16)	0.0262 (18)
C13	0.075 (2)	0.111 (3)	0.0500 (18)	0.031 (2)	−0.0128 (14)	−0.0029 (18)
C14	0.0644 (17)	0.075 (2)	0.0441 (16)	0.0152 (14)	−0.0061 (13)	−0.0042 (14)
C15	0.083 (2)	0.064 (2)	0.161 (4)	0.0066 (18)	0.016 (2)	0.038 (2)

N1—C7	1.270 (3)	C6—H6	0.9300
N1—N2	1.382 (3)	C7—H7	0.9300
N2—C8	1.338 (3)	C8—C9	1.487 (3)
N2—H2	0.895 (10)	C9—C14	1.375 (3)
O1—C2	1.345 (3)	C9—C10	1.381 (4)
O1—H1	0.8200	C10—C11	1.376 (4)
O2—C8	1.223 (3)	C10—H10	0.9300
C1—C6	1.392 (3)	C11—C12	1.362 (4)
C1—C2	1.395 (3)	C11—C15	1.500 (4)
C1—C7	1.447 (3)	C12—C13	1.380 (4)
C2—C3	1.390 (4)	C12—H12	0.9300
C3—C4	1.371 (4)	C13—C14	1.389 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.374 (4)	C14—H14	0.9300
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.373 (4)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C7—N1—N2	117.0 (2)	O2—C8—C9	120.8 (2)
C8—N2—N1	119.7 (2)	N2—C8—C9	116.0 (2)
C8—N2—H2	124.0 (19)	C14—C9—C10	119.3 (2)
N1—N2—H2	115.1 (19)	C14—C9—C8	122.2 (2)
C2—O1—H1	109.5	C10—C9—C8	118.5 (2)
C6—C1—C2	118.6 (2)	C11—C10—C9	122.1 (3)
C6—C1—C7	119.6 (2)	C11—C10—H10	118.9
C2—C1—C7	121.8 (2)	C9—C10—H10	118.9
O1—C2—C3	117.6 (2)	C12—C11—C10	118.1 (3)
O1—C2—C1	122.5 (2)	C12—C11—C15	121.0 (3)
C3—C2—C1	119.8 (2)	C10—C11—C15	120.9 (3)
C4—C3—C2	120.0 (3)	C11—C12—C13	121.1 (3)
C4—C3—H3	120.0	C11—C12—H12	119.5
C2—C3—H3	120.0	C13—C12—H12	119.5
C3—C4—C5	120.9 (3)	C12—C13—C14	120.4 (3)
C3—C4—H4	119.6	C12—C13—H13	119.8
C5—C4—H4	119.6	C14—C13—H13	119.8
C6—C5—C4	119.4 (3)	C9—C14—C13	118.9 (3)
C6—C5—H5	120.3	C9—C14—H14	120.5
C4—C5—H5	120.3	C13—C14—H14	120.5
C5—C6—C1	121.3 (3)	C11—C15—H15A	109.5
C5—C6—H6	119.4	C11—C15—H15B	109.5
C1—C6—H6	119.4	H15A—C15—H15B	109.5
N1—C7—C1	121.6 (2)	C11—C15—H15C	109.5
N1—C7—H7	119.2	H15A—C15—H15C	109.5
C1—C7—H7	119.2	H15B—C15—H15C	109.5
O2—C8—N2	123.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.91	2.624 (2)	146
N2—H2···O2i	0.90 (1)	1.91 (1)	2.793 (3)	168 (3)
C7—H7···O2i	0.93	2.49	3.229 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.91	2.624 (2)	146
N2—H2⋯O2i	0.90 (1)	1.91 (1)	2.793 (3)	168 (3)
C7—H7⋯O2i	0.93	2.49	3.229 (2)	137

Symmetry code: (i) .