(E)-2-Meth-oxy-N'-(2,4,6-trihy-droxy-benzyl-idene)benzohydrazide.

In the title hydrazone derivative, C(15)H(14)N(2)O(5), the benzene rings are twisted by 7.55 (8)° with respect to each other. The azomethine double bond adopts an E conformation. The mol-ecular structure is stabilized by intra-molecular O-H⋯N and N-H⋯O hydrogen bonds, generating S6 ring motifs. In the crystal, mol-ecules are linked into a three-dimensional network by O-H⋯O hydrogen bonds.

Related literature

For applications and biological activity of Schiff bases, see: Khan et al. (2011 ▶, 2012 ▶); Rada & Leto (2008 ▶); Almasirad et al. (2006 ▶). For related structures, see: Taha et al. (2012 ▶); Shen et al. (2012 ▶).

Experimental

Crystal data

C15H14N2O5

M = 302.28

Orthorhombic,

a = 6.4580 (4) Å

b = 13.4772 (8) Å

c = 16.3169 (9) Å

V = 1420.15 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 273 K

0.34 × 0.23 × 0.21 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.964, T max = 0.978

8414 measured reflections

2643 independent reflections

2481 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.080

S = 1.07

2643 reflections

216 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813001748/rz5037sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001748/rz5037Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001748/rz5037Isup3.cml

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

C15H14N2O5	F(000) = 632
Mr = 302.28	Dx = 1.414 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3988 reflections
a = 6.4580 (4) Å	θ = 2.5–27.8°
b = 13.4772 (8) Å	µ = 0.11 mm−1
c = 16.3169 (9) Å	T = 273 K
V = 1420.15 (14) Å3	Block, colourless
Z = 4	0.34 × 0.23 × 0.21 mm

Bruker SMART APEX CCD area-detector diffractometer	2643 independent reflections
Radiation source: fine-focus sealed tube	2481 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
ω scan	θmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −6→7
Tmin = 0.964, Tmax = 0.978	k = −16→16
8414 measured reflections	l = −19→19

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0444P)2 + 0.1141P] where P = (Fo2 + 2Fc2)/3
2643 reflections	(Δ/σ)max < 0.001
216 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.13 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	0.5330 (2)	0.22125 (9)	0.11606 (8)	0.0543 (3)
O2	1.1070 (2)	0.40655 (9)	0.02009 (8)	0.0578 (3)
H3A	1.091 (5)	0.3604 (19)	−0.0222 (16)	0.100 (8)*
O3	0.6905 (2)	0.53380 (9)	0.23545 (7)	0.0511 (3)
H2B	0.785 (3)	0.5781 (16)	0.2396 (12)	0.065 (7)*
O4	0.0021 (2)	0.16307 (8)	0.25569 (7)	0.0518 (3)
O5	−0.0653 (2)	0.42748 (8)	0.38286 (8)	0.0578 (3)
N1	0.2953 (2)	0.30535 (10)	0.22647 (8)	0.0421 (3)
N2	0.1262 (2)	0.31688 (11)	0.27673 (8)	0.0436 (3)
H2A	0.111 (3)	0.3735 (14)	0.2990 (11)	0.054 (5)*
C1	0.6522 (2)	0.30443 (11)	0.12072 (9)	0.0403 (3)
C2	0.8209 (3)	0.31059 (12)	0.06945 (10)	0.0447 (4)
H2C	0.8508	0.2594	0.0331	0.054*
C3	0.9454 (3)	0.39399 (11)	0.07272 (9)	0.0419 (4)
C4	0.9087 (2)	0.46946 (11)	0.12866 (9)	0.0410 (3)
H4A	0.9973	0.5238	0.1318	0.049*
C5	0.7383 (2)	0.46267 (10)	0.17972 (9)	0.0382 (3)
C6	0.6031 (2)	0.38110 (11)	0.17590 (9)	0.0377 (3)
C7	0.4203 (3)	0.37914 (12)	0.22646 (9)	0.0411 (3)
H7A	0.3922	0.4331	0.2602	0.049*
C8	−0.0127 (2)	0.24489 (11)	0.28886 (9)	0.0385 (3)
C9	−0.1900 (2)	0.26844 (11)	0.34441 (9)	0.0376 (3)
C10	−0.3409 (3)	0.19578 (12)	0.35197 (10)	0.0448 (4)
H10A	−0.3256	0.1368	0.3231	0.054*
C11	−0.5130 (3)	0.20830 (14)	0.40098 (10)	0.0521 (4)
H11A	−0.6111	0.1581	0.4055	0.063*
C12	−0.5376 (3)	0.29535 (14)	0.44283 (10)	0.0550 (5)
H12A	−0.6537	0.3043	0.4758	0.066*
C13	−0.3922 (3)	0.37023 (14)	0.43680 (10)	0.0512 (4)
H13A	−0.4119	0.4295	0.4650	0.061*
C14	−0.2165 (3)	0.35718 (12)	0.38868 (9)	0.0431 (4)
C15	−0.0887 (4)	0.52036 (14)	0.42409 (13)	0.0725 (6)
H15A	0.0214	0.5642	0.4082	0.109*
H15B	−0.0837	0.5099	0.4823	0.109*
H15C	−0.2194	0.5494	0.4096	0.109*
H1A	0.432 (4)	0.2267 (18)	0.1484 (15)	0.094 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0576 (8)	0.0517 (7)	0.0535 (7)	−0.0166 (6)	0.0105 (6)	−0.0109 (5)
O2	0.0546 (8)	0.0572 (7)	0.0615 (7)	−0.0047 (6)	0.0220 (7)	−0.0072 (6)
O3	0.0522 (8)	0.0449 (7)	0.0562 (7)	−0.0059 (6)	0.0124 (6)	−0.0104 (5)
O4	0.0498 (7)	0.0414 (6)	0.0640 (7)	0.0035 (5)	0.0084 (6)	−0.0035 (5)
O5	0.0560 (8)	0.0481 (6)	0.0692 (8)	−0.0065 (6)	0.0153 (7)	−0.0140 (6)
N1	0.0348 (7)	0.0485 (7)	0.0429 (7)	0.0014 (6)	0.0043 (6)	0.0031 (6)
N2	0.0360 (7)	0.0438 (7)	0.0509 (8)	0.0004 (6)	0.0083 (6)	−0.0015 (6)
C1	0.0416 (9)	0.0404 (7)	0.0388 (7)	−0.0034 (7)	−0.0035 (7)	0.0019 (6)
C2	0.0500 (10)	0.0429 (8)	0.0411 (8)	0.0020 (8)	0.0065 (7)	−0.0041 (6)
C3	0.0387 (9)	0.0456 (8)	0.0416 (8)	0.0031 (7)	0.0052 (7)	0.0058 (6)
C4	0.0411 (9)	0.0375 (7)	0.0444 (8)	−0.0031 (7)	0.0017 (7)	0.0022 (6)
C5	0.0405 (8)	0.0375 (7)	0.0365 (7)	0.0049 (7)	−0.0005 (7)	0.0021 (6)
C6	0.0362 (8)	0.0416 (8)	0.0354 (7)	0.0020 (7)	−0.0004 (7)	0.0043 (6)
C7	0.0388 (9)	0.0448 (8)	0.0396 (8)	0.0021 (7)	0.0009 (7)	0.0021 (6)
C8	0.0355 (8)	0.0398 (8)	0.0401 (7)	0.0060 (7)	−0.0030 (7)	0.0061 (6)
C9	0.0341 (8)	0.0421 (8)	0.0366 (7)	0.0034 (6)	−0.0015 (6)	0.0057 (6)
C10	0.0418 (9)	0.0471 (8)	0.0453 (8)	−0.0014 (7)	−0.0017 (7)	0.0050 (7)
C11	0.0427 (10)	0.0657 (11)	0.0480 (9)	−0.0100 (9)	0.0030 (8)	0.0080 (8)
C12	0.0410 (10)	0.0777 (12)	0.0462 (9)	0.0026 (9)	0.0109 (8)	0.0080 (8)
C13	0.0520 (11)	0.0583 (10)	0.0433 (8)	0.0049 (9)	0.0070 (8)	−0.0027 (7)
C14	0.0408 (9)	0.0484 (8)	0.0403 (8)	0.0006 (7)	0.0002 (7)	0.0037 (7)
C15	0.0877 (16)	0.0541 (11)	0.0757 (12)	−0.0109 (11)	0.0154 (12)	−0.0200 (9)

O1—C1	1.3622 (18)	C4—H4A	0.9300
O1—H1A	0.84 (3)	C5—C6	1.405 (2)
O2—C3	1.362 (2)	C6—C7	1.440 (2)
O2—H3A	0.93 (3)	C7—H7A	0.9300
O3—C5	1.3569 (18)	C8—C9	1.494 (2)
O3—H2B	0.86 (2)	C9—C10	1.387 (2)
O4—C8	1.2321 (19)	C9—C14	1.408 (2)
O5—C14	1.364 (2)	C10—C11	1.379 (2)
O5—C15	1.429 (2)	C10—H10A	0.9300
N1—C7	1.281 (2)	C11—C12	1.367 (3)
N1—N2	1.3742 (18)	C11—H11A	0.9300
N2—C8	1.336 (2)	C12—C13	1.382 (3)
N2—H2A	0.851 (19)	C12—H12A	0.9300
C1—C2	1.376 (2)	C13—C14	1.391 (2)
C1—C6	1.407 (2)	C13—H13A	0.9300
C2—C3	1.383 (2)	C15—H15A	0.9600
C2—H2C	0.9300	C15—H15B	0.9600
C3—C4	1.387 (2)	C15—H15C	0.9600
C4—C5	1.384 (2)
C1—O1—H1A	109.3 (17)	C6—C7—H7A	119.0
C3—O2—H3A	107.3 (17)	O4—C8—N2	122.19 (14)
C5—O3—H2B	112.6 (14)	O4—C8—C9	121.05 (14)
C14—O5—C15	120.00 (14)	N2—C8—C9	116.75 (13)
C7—N1—N2	114.39 (13)	C10—C9—C14	117.96 (14)
C8—N2—N1	122.66 (13)	C10—C9—C8	116.26 (13)
C8—N2—H2A	120.7 (14)	C14—C9—C8	125.78 (14)
N1—N2—H2A	116.6 (14)	C11—C10—C9	122.09 (16)
O1—C1—C2	117.59 (14)	C11—C10—H10A	119.0
O1—C1—C6	120.85 (14)	C9—C10—H10A	119.0
C2—C1—C6	121.56 (14)	C12—C11—C10	119.24 (16)
C1—C2—C3	119.07 (14)	C12—C11—H11A	120.4
C1—C2—H2C	120.5	C10—C11—H11A	120.4
C3—C2—H2C	120.5	C11—C12—C13	120.80 (16)
O2—C3—C2	121.47 (14)	C11—C12—H12A	119.6
O2—C3—C4	117.05 (14)	C13—C12—H12A	119.6
C2—C3—C4	121.47 (14)	C12—C13—C14	120.14 (16)
C5—C4—C3	118.93 (14)	C12—C13—H13A	119.9
C5—C4—H4A	120.5	C14—C13—H13A	119.9
C3—C4—H4A	120.5	O5—C14—C13	122.37 (15)
O3—C5—C4	122.54 (14)	O5—C14—C9	117.88 (14)
O3—C5—C6	116.16 (13)	C13—C14—C9	119.75 (15)
C4—C5—C6	121.29 (13)	O5—C15—H15A	109.5
C5—C6—C1	117.57 (13)	O5—C15—H15B	109.5
C5—C6—C7	119.87 (13)	H15A—C15—H15B	109.5
C1—C6—C7	122.55 (14)	O5—C15—H15C	109.5
N1—C7—C6	122.06 (14)	H15A—C15—H15C	109.5
N1—C7—H7A	119.0	H15B—C15—H15C	109.5
C7—N1—N2—C8	−175.22 (14)	N1—N2—C8—O4	0.1 (2)
O1—C1—C2—C3	−179.90 (15)	N1—N2—C8—C9	−179.32 (13)
C6—C1—C2—C3	0.4 (2)	O4—C8—C9—C10	−3.9 (2)
C1—C2—C3—O2	−176.07 (15)	N2—C8—C9—C10	175.56 (14)
C1—C2—C3—C4	2.6 (2)	O4—C8—C9—C14	176.47 (15)
O2—C3—C4—C5	175.90 (14)	N2—C8—C9—C14	−4.1 (2)
C2—C3—C4—C5	−2.8 (2)	C14—C9—C10—C11	0.0 (2)
C3—C4—C5—O3	−179.30 (14)	C8—C9—C10—C11	−179.71 (14)
C3—C4—C5—C6	0.1 (2)	C9—C10—C11—C12	0.8 (2)
O3—C5—C6—C1	−177.87 (13)	C10—C11—C12—C13	−0.3 (3)
C4—C5—C6—C1	2.7 (2)	C11—C12—C13—C14	−0.9 (3)
O3—C5—C6—C7	3.1 (2)	C15—O5—C14—C13	−2.9 (2)
C4—C5—C6—C7	−176.29 (13)	C15—O5—C14—C9	177.58 (16)
O1—C1—C6—C5	177.32 (14)	C12—C13—C14—O5	−177.81 (16)
C2—C1—C6—C5	−2.9 (2)	C12—C13—C14—C9	1.7 (2)
O1—C1—C6—C7	−3.7 (2)	C10—C9—C14—O5	178.31 (14)
C2—C1—C6—C7	176.02 (15)	C8—C9—C14—O5	−2.0 (2)
N2—N1—C7—C6	−178.41 (13)	C10—C9—C14—C13	−1.2 (2)
C5—C6—C7—N1	−178.30 (14)	C8—C9—C14—C13	178.45 (14)
C1—C6—C7—N1	2.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.84 (3)	1.88 (2)	2.6243 (18)	147 (2)
N2—H2A···O5	0.851 (19)	1.923 (19)	2.5981 (18)	135.4 (17)
O3—H2B···O4i	0.86 (2)	1.79 (2)	2.6452 (17)	175 (2)
O2—H3A···O1ii	0.93 (3)	1.92 (3)	2.8513 (18)	172 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.84 (3)	1.88 (2)	2.6243 (18)	147 (2)
N2—H2A⋯O5	0.851 (19)	1.923 (19)	2.5981 (18)	135.4 (17)
O3—H2B⋯O4i	0.86 (2)	1.79 (2)	2.6452 (17)	175 (2)
O2—H3A⋯O1ii	0.93 (3)	1.92 (3)	2.8513 (18)	172 (3)

Symmetry codes: (i) ; (ii) .