N'-[(E)-4-Benz-yloxy-2-hy-droxy-benzyl-idene]benzohydrazide.

The title compound, C(21)H(18)N(2)O(3), exists in the E conformation with respect to the azomethane C=N double bond. The central benzene ring is almost coplanar with one of the substituent benzene rings [dihedral angle = 1.74 (5)°] and is approximately orthogonal to the other benzene ring of the mol-ecule [dihedral angle = 86.61 (7)°]. An intra-molecular O-H⋯N hydrogen bond occurs. The crystal packing is dominated by N-H⋯O hydrogen bonds, which lead to an infinite chain running parallel to [010].

Related literature

For the biological activity of hydrazones, see: Patil et al. (2010 ▶); Zhang et al. (2010 ▶). For the synthesis of related compounds, see: Emmanuel et al. (2011 ▶); Mangalam & Kurup (2011 ▶). For related structures, see: Lin & Sang (2009 ▶); Mohd Lair et al. (2009 ▶).

Experimental

Crystal data

C21H18N2O3

M = 346.37

Monoclinic,

a = 10.8053 (6) Å

b = 4.8952 (2) Å

c = 16.3601 (10) Å

β = 95.813 (2)°

V = 860.90 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.969, T max = 0.978

9033 measured reflections

1705 independent reflections

1593 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.082

S = 1.12

1705 reflections

243 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036306/fj2591sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036306/fj2591Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036306/fj2591Isup3.cml

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

C21H18N2O3	F(000) = 364
Mr = 346.37	Dx = 1.336 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5951 reflections
a = 10.8053 (6) Å	θ = 2.4–28.1°
b = 4.8952 (2) Å	µ = 0.09 mm−1
c = 16.3601 (10) Å	T = 296 K
β = 95.813 (2)°	Block, colorless
V = 860.90 (8) Å3	0.35 × 0.30 × 0.25 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	1705 independent reflections
Radiation source: fine-focus sealed tube	1593 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 8.33 pixels mm-1	θmax = 25.0°, θmin = 3.0°
ω and φ scan	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −5→5
Tmin = 0.969, Tmax = 0.978	l = −19→19
9033 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0492P)2 + 0.0573P] where P = (Fo2 + 2Fc2)/3
1705 reflections	(Δ/σ)max = 0.005
243 parameters	Δρmax = 0.12 e Å−3
3 restraints	Δρmin = −0.14 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
O1	0.08187 (12)	0.6299 (3)	1.18699 (7)	0.0525 (4)
O2	0.19313 (15)	0.4504 (4)	0.91841 (8)	0.0610 (4)
O3	0.43474 (14)	0.3828 (3)	0.76116 (9)	0.0575 (4)
N1	0.37436 (15)	0.7368 (4)	0.87075 (9)	0.0471 (4)
N2	0.44743 (17)	0.8127 (3)	0.81016 (10)	0.0458 (4)
C1	−0.1620 (2)	0.5457 (6)	1.27899 (13)	0.0681 (7)
H1	−0.1984	0.6716	1.2413	0.082*
C2	−0.2072 (2)	0.5169 (8)	1.35467 (15)	0.0812 (9)
H2A	−0.2737	0.6235	1.3677	0.097*
C3	−0.1550 (3)	0.3347 (7)	1.40967 (15)	0.0779 (8)
H3	−0.1853	0.3174	1.4607	0.093*
C4	−0.0583 (3)	0.1761 (8)	1.39081 (16)	0.0890 (9)
H4	−0.0228	0.0501	1.4288	0.107*
C5	−0.0126 (2)	0.2025 (7)	1.31467 (15)	0.0750 (7)
H5	0.0528	0.0928	1.3015	0.090*
C6	−0.06386 (17)	0.3899 (5)	1.25910 (11)	0.0500 (5)
C7	−0.01383 (18)	0.4243 (5)	1.17735 (11)	0.0531 (5)
H7A	0.0203	0.2531	1.1600	0.064*
H7B	−0.0798	0.4808	1.1361	0.064*
C8	0.14629 (15)	0.6828 (4)	1.12181 (10)	0.0424 (4)
C9	0.13243 (17)	0.5416 (4)	1.04847 (11)	0.0464 (5)
H9	0.0725	0.4054	1.0401	0.056*
C10	0.20779 (17)	0.6026 (4)	0.98724 (10)	0.0431 (4)
C11	0.29517 (17)	0.8163 (4)	0.99739 (10)	0.0421 (4)
C12	0.30438 (17)	0.9593 (5)	1.07174 (11)	0.0501 (5)
H12	0.3604	1.1034	1.0794	0.060*
C13	0.23345 (17)	0.8937 (5)	1.13355 (11)	0.0493 (5)
H13	0.2431	0.9886	1.1830	0.059*
C14	0.37200 (17)	0.8897 (5)	0.93334 (11)	0.0470 (4)
H14	0.4195	1.0484	0.9380	0.056*
C15	0.47098 (17)	0.6182 (4)	0.75527 (11)	0.0427 (4)
C16	0.54733 (16)	0.7030 (4)	0.68911 (11)	0.0433 (4)
C17	0.5333 (2)	0.5618 (5)	0.61561 (12)	0.0565 (6)
H17	0.4738	0.4244	0.6077	0.068*
C18	0.6065 (2)	0.6223 (6)	0.55402 (13)	0.0671 (6)
H18	0.5957	0.5273	0.5046	0.080*
C19	0.6950 (2)	0.8216 (6)	0.56521 (14)	0.0673 (7)
H19	0.7449	0.8610	0.5236	0.081*
C20	0.7105 (2)	0.9643 (6)	0.63802 (14)	0.0655 (6)
H20	0.7709	1.0998	0.6455	0.079*
C21	0.63653 (18)	0.9069 (5)	0.70001 (13)	0.0532 (5)
H21	0.6466	1.0048	0.7489	0.064*
H2'	0.4593 (19)	0.9831 (9)	0.8048 (13)	0.047 (6)*
H2''	0.249 (2)	0.514 (7)	0.8883 (16)	0.100 (10)*

	U11	U22	U33	U12	U13	U23
O1	0.0541 (7)	0.0627 (10)	0.0425 (6)	−0.0105 (7)	0.0144 (5)	−0.0043 (7)
O2	0.0859 (10)	0.0528 (10)	0.0474 (7)	−0.0177 (8)	0.0207 (7)	−0.0110 (7)
O3	0.0747 (9)	0.0345 (8)	0.0668 (9)	−0.0058 (7)	0.0238 (7)	0.0026 (7)
N1	0.0560 (9)	0.0423 (10)	0.0454 (8)	0.0030 (8)	0.0161 (7)	0.0061 (8)
N2	0.0602 (9)	0.0320 (9)	0.0478 (8)	0.0002 (7)	0.0184 (7)	0.0059 (7)
C1	0.0652 (12)	0.0807 (18)	0.0605 (12)	0.0120 (13)	0.0162 (10)	0.0076 (13)
C2	0.0728 (15)	0.103 (2)	0.0724 (15)	0.0086 (16)	0.0311 (12)	−0.0023 (17)
C3	0.0884 (17)	0.090 (2)	0.0604 (13)	−0.0181 (17)	0.0300 (12)	0.0016 (15)
C4	0.106 (2)	0.094 (2)	0.0688 (15)	0.0056 (19)	0.0186 (14)	0.0313 (17)
C5	0.0768 (15)	0.0803 (19)	0.0712 (14)	0.0118 (14)	0.0235 (12)	0.0150 (14)
C6	0.0466 (10)	0.0556 (12)	0.0488 (9)	−0.0096 (10)	0.0094 (8)	−0.0032 (10)
C7	0.0530 (10)	0.0581 (14)	0.0497 (10)	−0.0071 (11)	0.0115 (8)	−0.0053 (10)
C8	0.0418 (9)	0.0464 (12)	0.0396 (9)	0.0028 (8)	0.0060 (7)	0.0006 (9)
C9	0.0505 (10)	0.0439 (11)	0.0454 (10)	−0.0058 (9)	0.0078 (8)	0.0003 (9)
C10	0.0536 (10)	0.0382 (10)	0.0377 (8)	0.0020 (9)	0.0059 (7)	0.0002 (8)
C11	0.0447 (9)	0.0407 (11)	0.0414 (9)	0.0028 (8)	0.0061 (7)	0.0016 (8)
C12	0.0504 (10)	0.0492 (13)	0.0508 (10)	−0.0105 (10)	0.0055 (8)	−0.0052 (9)
C13	0.0542 (10)	0.0547 (12)	0.0391 (9)	−0.0051 (10)	0.0055 (7)	−0.0061 (10)
C14	0.0487 (9)	0.0425 (11)	0.0507 (10)	−0.0011 (9)	0.0091 (8)	0.0022 (10)
C15	0.0482 (10)	0.0349 (10)	0.0460 (9)	0.0024 (9)	0.0089 (7)	0.0057 (9)
C16	0.0482 (10)	0.0364 (10)	0.0465 (9)	0.0053 (8)	0.0097 (8)	0.0052 (8)
C17	0.0673 (12)	0.0523 (14)	0.0515 (11)	−0.0063 (11)	0.0139 (9)	−0.0026 (10)
C18	0.0844 (15)	0.0710 (17)	0.0487 (11)	−0.0028 (15)	0.0210 (10)	−0.0012 (12)
C19	0.0731 (14)	0.0721 (17)	0.0613 (13)	0.0023 (13)	0.0296 (11)	0.0135 (13)
C20	0.0601 (12)	0.0620 (16)	0.0779 (15)	−0.0129 (12)	0.0245 (10)	0.0058 (13)
C21	0.0565 (10)	0.0488 (12)	0.0558 (10)	−0.0040 (10)	0.0131 (8)	0.0003 (10)

O1—C8	1.356 (2)	C8—C9	1.380 (3)
O1—C7	1.440 (3)	C8—C13	1.397 (3)
O2—C10	1.346 (2)	C9—C10	1.386 (3)
O2—H2''	0.871 (18)	C9—H9	0.9300
O3—C15	1.224 (3)	C10—C11	1.407 (3)
N1—C14	1.271 (2)	C11—C12	1.398 (3)
N1—N2	1.379 (2)	C11—C14	1.447 (2)
N2—C15	1.350 (3)	C12—C13	1.367 (3)
N2—H2'	0.8500 (11)	C12—H12	0.9300
C1—C6	1.372 (3)	C13—H13	0.9300
C1—C2	1.383 (3)	C14—H14	0.9300
C1—H1	0.9300	C15—C16	1.485 (2)
C2—C3	1.349 (4)	C16—C17	1.382 (3)
C2—H2A	0.9300	C16—C21	1.386 (3)
C3—C4	1.363 (4)	C17—C18	1.375 (3)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.392 (3)	C18—C19	1.365 (4)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.369 (4)	C19—C20	1.376 (3)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.502 (2)	C20—C21	1.382 (3)
C7—H7A	0.9700	C20—H20	0.9300
C7—H7B	0.9700	C21—H21	0.9300
C8—O1—C7	117.87 (14)	O2—C10—C9	117.22 (18)
C10—O2—H2''	104 (2)	O2—C10—C11	122.05 (16)
C14—N1—N2	118.70 (17)	C9—C10—C11	120.73 (17)
C15—N2—N1	116.64 (16)	C12—C11—C10	117.55 (16)
C15—N2—H2'	125.7 (15)	C12—C11—C14	120.68 (18)
N1—N2—H2'	116.2 (15)	C10—C11—C14	121.77 (17)
C6—C1—C2	120.5 (2)	C13—C12—C11	121.99 (19)
C6—C1—H1	119.8	C13—C12—H12	119.0
C2—C1—H1	119.8	C11—C12—H12	119.0
C3—C2—C1	120.2 (3)	C12—C13—C8	119.49 (17)
C3—C2—H2A	119.9	C12—C13—H13	120.3
C1—C2—H2A	119.9	C8—C13—H13	120.3
C2—C3—C4	120.3 (2)	N1—C14—C11	119.8 (2)
C2—C3—H3	119.9	N1—C14—H14	120.1
C4—C3—H3	119.9	C11—C14—H14	120.1
C3—C4—C5	120.0 (3)	O3—C15—N2	121.87 (17)
C3—C4—H4	120.0	O3—C15—C16	121.75 (18)
C5—C4—H4	120.0	N2—C15—C16	116.34 (18)
C6—C5—C4	120.0 (3)	C17—C16—C21	119.04 (17)
C6—C5—H5	120.0	C17—C16—C15	118.32 (18)
C4—C5—H5	120.0	C21—C16—C15	122.54 (18)
C5—C6—C1	119.1 (2)	C18—C17—C16	120.6 (2)
C5—C6—C7	120.6 (2)	C18—C17—H17	119.7
C1—C6—C7	120.4 (2)	C16—C17—H17	119.7
O1—C7—C6	107.46 (16)	C19—C18—C17	120.2 (2)
O1—C7—H7A	110.2	C19—C18—H18	119.9
C6—C7—H7A	110.2	C17—C18—H18	119.9
O1—C7—H7B	110.2	C18—C19—C20	120.06 (19)
C6—C7—H7B	110.2	C18—C19—H19	120.0
H7A—C7—H7B	108.5	C20—C19—H19	120.0
O1—C8—C9	124.68 (17)	C19—C20—C21	120.2 (2)
O1—C8—C13	115.18 (16)	C19—C20—H20	119.9
C9—C8—C13	120.13 (16)	C21—C20—H20	119.9
C8—C9—C10	120.04 (18)	C20—C21—C16	119.9 (2)
C8—C9—H9	120.0	C20—C21—H21	120.1
C10—C9—H9	120.0	C16—C21—H21	120.1
C14—N1—N2—C15	164.71 (18)	C10—C11—C12—C13	1.2 (3)
C6—C1—C2—C3	−0.1 (4)	C14—C11—C12—C13	−179.66 (19)
C1—C2—C3—C4	−0.6 (5)	C11—C12—C13—C8	−1.9 (3)
C2—C3—C4—C5	0.3 (5)	O1—C8—C13—C12	178.99 (18)
C3—C4—C5—C6	0.7 (5)	C9—C8—C13—C12	0.2 (3)
C4—C5—C6—C1	−1.4 (4)	N2—N1—C14—C11	179.39 (16)
C4—C5—C6—C7	178.8 (3)	C12—C11—C14—N1	170.89 (18)
C2—C1—C6—C5	1.0 (4)	C10—C11—C14—N1	−10.0 (3)
C2—C1—C6—C7	−179.1 (3)	N1—N2—C15—O3	−3.6 (3)
C8—O1—C7—C6	175.83 (17)	N1—N2—C15—C16	178.67 (15)
C5—C6—C7—O1	−90.4 (3)	O3—C15—C16—C17	28.2 (3)
C1—C6—C7—O1	89.8 (2)	N2—C15—C16—C17	−154.05 (19)
C7—O1—C8—C9	−4.4 (3)	O3—C15—C16—C21	−148.1 (2)
C7—O1—C8—C13	176.89 (17)	N2—C15—C16—C21	29.7 (3)
O1—C8—C9—C10	−176.51 (17)	C21—C16—C17—C18	−0.1 (3)
C13—C8—C9—C10	2.1 (3)	C15—C16—C17—C18	−176.5 (2)
C8—C9—C10—O2	177.42 (18)	C16—C17—C18—C19	0.7 (4)
C8—C9—C10—C11	−2.9 (3)	C17—C18—C19—C20	−0.6 (4)
O2—C10—C11—C12	−179.1 (2)	C18—C19—C20—C21	−0.1 (4)
C9—C10—C11—C12	1.2 (3)	C19—C20—C21—C16	0.6 (4)
O2—C10—C11—C14	1.8 (3)	C17—C16—C21—C20	−0.5 (3)
C9—C10—C11—C14	−177.93 (18)	C15—C16—C21—C20	175.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2′···O3i	0.85 (1)	2.09 (1)	2.903 (2)	160 (2)
O2—H2′′···N1	0.87 (2)	1.79 (2)	2.592 (2)	152 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2′⋯O3i	0.85 (1)	2.09 (1)	2.903 (2)	160 (2)
O2—H2′′⋯N1	0.87 (2)	1.79 (2)	2.592 (2)	152 (3)

Symmetry code: (i) .