4-Hy-droxy-N'-[1-(2-hy-droxy-phen-yl)ethyl-idene]benzohydrazide.

In the title compound, C(15)H(14)N(2)O(3), there is an intra-molecular O-H⋯N hydrogen bond and the dihedral angle between the two aromatic rings is 13.9 (3)°. In the crystal structure, mol-ecules are stabilized by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For related structures, see: Lu et al. (2008a ▶,b ▶,c ▶); Xiao & Wei (2009 ▶); He (2008 ▶); Shi et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H14N2O3

M = 270.28

Monoclinic,

a = 4.926 (2) Å

b = 31.06 (2) Å

c = 8.473 (3) Å

β = 93.852 (3)°

V = 1293.5 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.21 × 0.20 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.980, T max = 0.984

8965 measured reflections

2770 independent reflections

1569 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.172

S = 1.05

2770 reflections

188 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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/S1600536810019914/su2181sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019914/su2181Isup2.hkl

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

C15H14N2O3	F(000) = 568
Mr = 270.28	Dx = 1.388 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 957 reflections
a = 4.926 (2) Å	θ = 2.5–24.5°
b = 31.06 (2) Å	µ = 0.10 mm−1
c = 8.473 (3) Å	T = 298 K
β = 93.852 (3)°	Block, colourless
V = 1293.5 (11) Å3	0.21 × 0.20 × 0.17 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2770 independent reflections
Radiation source: fine-focus sealed tube	1569 reflections with I > 2σ(I)
graphite	Rint = 0.064
ω scans	θmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −6→6
Tmin = 0.980, Tmax = 0.984	k = −39→34
8965 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.069	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.172	w = 1/[σ2(Fo2) + (0.0649P)2 + 0.4306P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2770 reflections	Δρmax = 0.26 e Å−3
188 parameters	Δρmin = −0.21 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0057 (18)

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	0.9548 (5)	0.64659 (7)	0.6666 (3)	0.0384 (6)
N2	0.8786 (5)	0.68800 (7)	0.6186 (3)	0.0389 (6)
O1	1.2807 (5)	0.60332 (7)	0.8408 (3)	0.0581 (7)
H1	1.2112	0.6252	0.8021	0.087*
O2	1.3097 (4)	0.71011 (6)	0.6779 (3)	0.0510 (6)
O3	0.7088 (5)	0.89007 (6)	0.5716 (3)	0.0593 (7)
H3	0.5810	0.8920	0.5048	0.089*
C1	0.9088 (6)	0.57209 (9)	0.6782 (3)	0.0377 (7)
C2	1.1338 (6)	0.56842 (9)	0.7889 (3)	0.0413 (8)
C3	1.2167 (7)	0.52855 (10)	0.8469 (4)	0.0530 (9)
H3A	1.3668	0.5266	0.9192	0.064*
C4	1.0804 (8)	0.49197 (10)	0.7992 (4)	0.0603 (10)
H4	1.1375	0.4653	0.8389	0.072*
C5	0.8616 (8)	0.49468 (11)	0.6938 (5)	0.0644 (11)
H5	0.7681	0.4698	0.6618	0.077*
C6	0.7776 (7)	0.53373 (10)	0.6342 (4)	0.0544 (9)
H6	0.6274	0.5348	0.5617	0.065*
C7	0.8165 (6)	0.61399 (9)	0.6136 (3)	0.0366 (7)
C8	1.0701 (6)	0.71922 (9)	0.6405 (3)	0.0374 (7)
C9	0.9732 (6)	0.76376 (9)	0.6167 (3)	0.0346 (7)
C10	0.7529 (6)	0.77407 (9)	0.5133 (3)	0.0394 (7)
H10	0.6639	0.7523	0.4547	0.047*
C11	0.6634 (6)	0.81585 (9)	0.4958 (3)	0.0411 (8)
H11	0.5158	0.8222	0.4254	0.049*
C12	0.7927 (6)	0.84846 (9)	0.5827 (3)	0.0392 (7)
C13	1.0155 (6)	0.83870 (10)	0.6841 (4)	0.0477 (8)
H13	1.1056	0.8605	0.7415	0.057*
C14	1.1051 (6)	0.79695 (10)	0.7005 (4)	0.0446 (8)
H14	1.2560	0.7908	0.7687	0.054*
C15	0.5813 (7)	0.61695 (11)	0.4922 (4)	0.0541 (9)
H15A	0.4183	0.6075	0.5378	0.081*
H15B	0.6154	0.5990	0.4035	0.081*
H15C	0.5595	0.6463	0.4575	0.081*
H2	0.710 (3)	0.6991 (11)	0.622 (4)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0324 (14)	0.0301 (14)	0.0522 (15)	0.0026 (11)	0.0000 (11)	0.0024 (11)
N2	0.0325 (14)	0.0302 (14)	0.0531 (15)	0.0022 (11)	−0.0030 (12)	0.0062 (11)
O1	0.0596 (15)	0.0364 (13)	0.0744 (16)	−0.0035 (11)	−0.0252 (12)	0.0046 (11)
O2	0.0294 (12)	0.0443 (13)	0.0784 (16)	0.0045 (10)	−0.0033 (11)	0.0088 (11)
O3	0.0686 (18)	0.0336 (13)	0.0721 (17)	0.0086 (11)	−0.0224 (13)	−0.0024 (10)
C1	0.0364 (17)	0.0327 (16)	0.0439 (16)	−0.0017 (13)	0.0030 (13)	−0.0025 (13)
C2	0.0458 (19)	0.0313 (17)	0.0464 (17)	−0.0017 (14)	0.0001 (14)	−0.0005 (13)
C3	0.062 (2)	0.0367 (19)	0.060 (2)	0.0050 (16)	−0.0040 (17)	0.0084 (15)
C4	0.077 (3)	0.0292 (19)	0.076 (2)	0.0094 (17)	0.013 (2)	0.0120 (16)
C5	0.072 (3)	0.0326 (19)	0.088 (3)	−0.0091 (18)	0.000 (2)	−0.0022 (17)
C6	0.055 (2)	0.041 (2)	0.066 (2)	−0.0074 (16)	−0.0070 (17)	−0.0049 (16)
C7	0.0340 (17)	0.0351 (16)	0.0405 (16)	0.0006 (13)	−0.0001 (13)	−0.0023 (12)
C8	0.0338 (17)	0.0386 (17)	0.0397 (16)	0.0010 (14)	0.0017 (13)	0.0043 (13)
C9	0.0314 (16)	0.0334 (16)	0.0388 (15)	0.0013 (13)	0.0017 (12)	0.0036 (12)
C10	0.0415 (18)	0.0313 (16)	0.0438 (17)	−0.0016 (13)	−0.0080 (13)	−0.0003 (13)
C11	0.0426 (18)	0.0367 (17)	0.0419 (17)	0.0008 (14)	−0.0125 (14)	0.0048 (13)
C12	0.0450 (18)	0.0277 (16)	0.0445 (17)	0.0026 (13)	−0.0013 (14)	0.0032 (13)
C13	0.046 (2)	0.0353 (18)	0.0588 (19)	−0.0043 (14)	−0.0146 (16)	−0.0076 (15)
C14	0.0380 (18)	0.0428 (18)	0.0509 (19)	0.0019 (15)	−0.0127 (14)	0.0019 (14)
C15	0.049 (2)	0.053 (2)	0.058 (2)	−0.0024 (17)	−0.0111 (16)	0.0030 (16)

N1—C7	1.284 (3)	C5—H5	0.9300
N1—N2	1.393 (3)	C6—H6	0.9300
N2—C8	1.357 (4)	C7—C15	1.500 (4)
N2—H2	0.900 (10)	C8—C9	1.473 (4)
O1—C2	1.360 (3)	C9—C10	1.385 (4)
O1—H1	0.8200	C9—C14	1.388 (4)
O2—C8	1.234 (3)	C10—C11	1.375 (4)
O3—C12	1.358 (3)	C10—H10	0.9300
O3—H3	0.8200	C11—C12	1.382 (4)
C1—C6	1.394 (4)	C11—H11	0.9300
C1—C2	1.407 (4)	C12—C13	1.381 (4)
C1—C7	1.472 (4)	C13—C14	1.374 (4)
C2—C3	1.384 (4)	C13—H13	0.9300
C3—C4	1.367 (4)	C14—H14	0.9300
C3—H3A	0.9300	C15—H15A	0.9600
C4—C5	1.356 (5)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C5—C6	1.367 (5)
C7—N1—N2	120.0 (2)	O2—C8—N2	121.0 (3)
C8—N2—N1	116.7 (2)	O2—C8—C9	123.1 (3)
C8—N2—H2	111 (2)	N2—C8—C9	115.9 (2)
N1—N2—H2	125 (2)	C10—C9—C14	118.1 (3)
C2—O1—H1	109.5	C10—C9—C8	122.5 (3)
C12—O3—H3	109.5	C14—C9—C8	119.4 (2)
C6—C1—C2	116.1 (3)	C11—C10—C9	121.2 (3)
C6—C1—C7	122.0 (3)	C11—C10—H10	119.4
C2—C1—C7	121.9 (2)	C9—C10—H10	119.4
O1—C2—C3	117.4 (3)	C10—C11—C12	120.1 (3)
O1—C2—C1	122.0 (2)	C10—C11—H11	120.0
C3—C2—C1	120.6 (3)	C12—C11—H11	120.0
C4—C3—C2	120.7 (3)	O3—C12—C13	118.5 (3)
C4—C3—H3A	119.6	O3—C12—C11	122.2 (3)
C2—C3—H3A	119.6	C13—C12—C11	119.3 (3)
C5—C4—C3	119.8 (3)	C14—C13—C12	120.4 (3)
C5—C4—H4	120.1	C14—C13—H13	119.8
C3—C4—H4	120.1	C12—C13—H13	119.8
C4—C5—C6	120.4 (3)	C13—C14—C9	120.9 (3)
C4—C5—H5	119.8	C13—C14—H14	119.6
C6—C5—H5	119.8	C9—C14—H14	119.6
C5—C6—C1	122.4 (3)	C7—C15—H15A	109.5
C5—C6—H6	118.8	C7—C15—H15B	109.5
C1—C6—H6	118.8	H15A—C15—H15B	109.5
N1—C7—C1	115.0 (2)	C7—C15—H15C	109.5
N1—C7—C15	124.0 (3)	H15A—C15—H15C	109.5
C1—C7—C15	121.0 (3)	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.78	2.499 (3)	146
O3—H3···O1i	0.82	1.97	2.786 (3)	179
N2—H2···O2ii	0.90 (1)	2.09 (2)	2.961 (4)	163 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.78	2.499 (3)	146
O3—H3⋯O1i	0.82	1.97	2.786 (3)	179
N2—H2⋯O2ii	0.90 (1)	2.09 (2)	2.961 (4)	163 (3)

Symmetry codes: (i) ; (ii) .