N'-(4-Hy-droxy-benzyl-idene)-2-methyl-benzohydrazide.

The title hydrazone compound, C(15)H(14)N(2)O(2), was prepared by the condensation of 4-hy-droxy-benzaldehyde with 2-methyl-benzohydrazide in methanol. The dihedral angle between the two benzene rings is 42.3 (2)°. In the crystal structure, mol-ecules are linked by inter-molecular O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds, forming a three-dimensional framework.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ▶); Pyta et al. (2010 ▶); Angelusiu et al. (2010 ▶); Fun et al. (2008 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H14N2O2

M = 254.28

Orthorhombic,

a = 7.6900 (15) Å

b = 11.701 (2) Å

c = 14.471 (3) Å

V = 1302.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.983, T max = 0.984

10755 measured reflections

1634 independent reflections

1502 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.101

S = 1.12

1634 reflections

177 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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/S1600536810035063/ci5176sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035063/ci5176Isup2.hkl

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

C15H14N2O2	F(000) = 536
Mr = 254.28	Dx = 1.297 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4917 reflections
a = 7.6900 (15) Å	θ = 2.2–27.1°
b = 11.701 (2) Å	µ = 0.09 mm−1
c = 14.471 (3) Å	T = 298 K
V = 1302.1 (4) Å3	Block, colourless
Z = 4	0.20 × 0.20 × 0.18 mm

Bruker SMART CCD area-detector diffractometer	1634 independent reflections
Radiation source: fine-focus sealed tube	1502 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.983, Tmax = 0.984	k = −14→14
10755 measured reflections	l = −18→18

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) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0604P)2 + 0.1042P] where P = (Fo2 + 2Fc2)/3
1634 reflections	(Δ/σ)max = 0.001
177 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.23 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.1045 (2)	0.76789 (13)	0.47260 (10)	0.0442 (4)
N2	0.1260 (2)	0.70443 (13)	0.55210 (10)	0.0433 (4)
O1	0.1276 (2)	1.15917 (11)	0.16838 (8)	0.0439 (3)
H1	0.0660	1.1323	0.1275	0.066*
O2	0.0277 (2)	0.54745 (11)	0.47842 (8)	0.0480 (4)
C1	0.1310 (2)	0.94736 (15)	0.39752 (11)	0.0369 (4)
C2	0.0694 (2)	0.90743 (16)	0.31255 (12)	0.0397 (4)
H2A	0.0288	0.8328	0.3080	0.048*
C3	0.0675 (2)	0.97611 (15)	0.23590 (12)	0.0391 (4)
H3	0.0264	0.9482	0.1799	0.047*
C4	0.1276 (2)	1.08777 (15)	0.24249 (11)	0.0345 (4)
C5	0.1884 (3)	1.12934 (16)	0.32573 (13)	0.0416 (4)
H5	0.2283	1.2042	0.3300	0.050*
C6	0.1899 (3)	1.05962 (16)	0.40250 (12)	0.0427 (4)
H6	0.2309	1.0880	0.4584	0.051*
C7	0.1410 (3)	0.87360 (15)	0.47796 (12)	0.0402 (4)
H7	0.1747	0.9043	0.5345	0.048*
C8	0.0859 (2)	0.59215 (15)	0.54852 (11)	0.0375 (4)
C9	0.1113 (2)	0.52835 (15)	0.63685 (12)	0.0389 (4)
C10	0.1715 (3)	0.41533 (17)	0.63644 (15)	0.0483 (5)
C11	0.1871 (3)	0.3609 (2)	0.7213 (2)	0.0631 (7)
H11	0.2286	0.2863	0.7229	0.076*
C12	0.1439 (3)	0.4126 (3)	0.80218 (18)	0.0703 (8)
H12	0.1559	0.3732	0.8576	0.084*
C13	0.0828 (3)	0.5227 (2)	0.80235 (14)	0.0649 (7)
H13	0.0519	0.5579	0.8576	0.078*
C14	0.0678 (3)	0.5808 (2)	0.71959 (13)	0.0498 (5)
H14	0.0280	0.6559	0.7194	0.060*
C15	0.2224 (4)	0.3530 (2)	0.5498 (2)	0.0763 (8)
H15A	0.1196	0.3306	0.5167	0.114*
H15B	0.2886	0.2863	0.5656	0.114*
H15C	0.2915	0.4024	0.5116	0.114*
H2	0.190 (3)	0.733 (2)	0.5994 (13)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0618 (10)	0.0404 (8)	0.0303 (7)	−0.0046 (8)	−0.0064 (7)	0.0072 (6)
N2	0.0622 (10)	0.0384 (8)	0.0294 (7)	−0.0076 (8)	−0.0103 (7)	0.0068 (6)
O1	0.0610 (8)	0.0385 (6)	0.0322 (6)	−0.0012 (6)	−0.0033 (6)	0.0082 (5)
O2	0.0697 (9)	0.0413 (7)	0.0329 (6)	−0.0064 (7)	−0.0078 (6)	−0.0010 (6)
C1	0.0426 (9)	0.0353 (8)	0.0327 (8)	0.0014 (8)	−0.0021 (7)	0.0036 (7)
C2	0.0499 (10)	0.0322 (8)	0.0371 (9)	−0.0036 (8)	−0.0030 (8)	0.0023 (7)
C3	0.0485 (10)	0.0373 (9)	0.0316 (8)	0.0001 (8)	−0.0038 (7)	−0.0014 (7)
C4	0.0380 (8)	0.0335 (8)	0.0319 (8)	0.0054 (7)	0.0010 (7)	0.0054 (7)
C5	0.0537 (11)	0.0304 (8)	0.0407 (9)	−0.0019 (8)	−0.0045 (8)	0.0012 (7)
C6	0.0566 (11)	0.0393 (9)	0.0322 (8)	−0.0018 (9)	−0.0088 (8)	−0.0008 (8)
C7	0.0504 (10)	0.0396 (9)	0.0305 (8)	−0.0009 (8)	−0.0039 (8)	0.0016 (8)
C8	0.0437 (9)	0.0370 (8)	0.0317 (8)	−0.0007 (8)	−0.0010 (7)	0.0020 (7)
C9	0.0414 (9)	0.0390 (9)	0.0361 (8)	−0.0069 (8)	−0.0055 (8)	0.0068 (7)
C10	0.0468 (11)	0.0388 (9)	0.0592 (12)	−0.0054 (8)	−0.0076 (9)	0.0087 (9)
C11	0.0553 (13)	0.0510 (12)	0.0831 (17)	−0.0073 (10)	−0.0172 (13)	0.0303 (13)
C12	0.0643 (14)	0.0870 (18)	0.0594 (14)	−0.0195 (15)	−0.0179 (11)	0.0431 (14)
C13	0.0711 (15)	0.0877 (19)	0.0361 (10)	−0.0117 (14)	−0.0034 (10)	0.0141 (11)
C14	0.0590 (12)	0.0541 (11)	0.0364 (9)	−0.0040 (10)	−0.0023 (9)	0.0065 (9)
C15	0.092 (2)	0.0484 (12)	0.0880 (18)	0.0146 (14)	−0.0047 (17)	−0.0092 (14)

N1—C7	1.271 (2)	C6—H6	0.93
N1—N2	1.379 (2)	C7—H7	0.93
N2—C8	1.350 (2)	C8—C9	1.493 (2)
N2—H2	0.907 (10)	C9—C14	1.387 (3)
O1—C4	1.3594 (19)	C9—C10	1.401 (3)
O1—H1	0.82	C10—C11	1.389 (3)
O2—C8	1.226 (2)	C10—C15	1.503 (3)
C1—C6	1.391 (3)	C11—C12	1.358 (4)
C1—C2	1.398 (2)	C11—H11	0.93
C1—C7	1.451 (2)	C12—C13	1.371 (4)
C2—C3	1.370 (2)	C12—H12	0.93
C2—H2A	0.93	C13—C14	1.382 (3)
C3—C4	1.389 (3)	C13—H13	0.93
C3—H3	0.93	C14—H14	0.93
C4—C5	1.381 (2)	C15—H15A	0.96
C5—C6	1.378 (2)	C15—H15B	0.96
C5—H5	0.93	C15—H15C	0.96
C7—N1—N2	116.54 (15)	O2—C8—C9	122.87 (16)
C8—N2—N1	117.68 (14)	N2—C8—C9	115.07 (15)
C8—N2—H2	120.6 (17)	C14—C9—C10	120.08 (17)
N1—N2—H2	119.9 (17)	C14—C9—C8	119.10 (17)
C4—O1—H1	109.5	C10—C9—C8	120.77 (17)
C6—C1—C2	118.12 (15)	C11—C10—C9	117.2 (2)
C6—C1—C7	120.18 (16)	C11—C10—C15	119.6 (2)
C2—C1—C7	121.65 (16)	C9—C10—C15	123.19 (19)
C3—C2—C1	121.31 (16)	C12—C11—C10	122.5 (2)
C3—C2—H2A	119.3	C12—C11—H11	118.8
C1—C2—H2A	119.3	C10—C11—H11	118.8
C2—C3—C4	119.52 (16)	C11—C12—C13	120.2 (2)
C2—C3—H3	120.2	C11—C12—H12	119.9
C4—C3—H3	120.2	C13—C12—H12	119.9
O1—C4—C5	118.15 (16)	C12—C13—C14	119.3 (2)
O1—C4—C3	121.59 (15)	C12—C13—H13	120.3
C5—C4—C3	120.26 (15)	C14—C13—H13	120.3
C6—C5—C4	119.83 (16)	C13—C14—C9	120.7 (2)
C6—C5—H5	120.1	C13—C14—H14	119.7
C4—C5—H5	120.1	C9—C14—H14	119.7
C5—C6—C1	120.96 (16)	C10—C15—H15A	109.5
C5—C6—H6	119.5	C10—C15—H15B	109.5
C1—C6—H6	119.5	H15A—C15—H15B	109.5
N1—C7—C1	121.21 (16)	C10—C15—H15C	109.5
N1—C7—H7	119.4	H15A—C15—H15C	109.5
C1—C7—H7	119.4	H15B—C15—H15C	109.5
O2—C8—N2	122.01 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.96	2.7657 (18)	166
O1—H1···N1i	0.82	2.52	2.995 (2)	118
N2—H2···O1ii	0.91 (1)	2.14 (1)	2.995 (2)	158 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.96	2.7657 (18)	166
O1—H1⋯N1i	0.82	2.52	2.995 (2)	118
N2—H2⋯O1ii	0.91 (1)	2.14 (1)	2.995 (2)	158 (2)

Symmetry codes: (i) ; (ii) .