2-{2-[(E)-(2-Benzoyl-hydrazin-1-yl-idene)meth-yl]phen-oxy}acetic acid.

In the title compound, C(16)H(14)N(2)O(4), the dihedral angle between the aromatic rings is 12.45 (6)°. The central C(=O)-N-N=C bridge is roughly planar (r.m.s. deviation = 0.0346 Å) and makes dihedral angles of 13.01 (7) and 0.56 (7)° with the attached phenyl and benzene rings, respectively. The acetic acid unit (r.m.s. deviation = 0.0066 Å) is twisted from its attached benzene ring [dihedral angle = 19.48 (6)°]. In the crystal, mol-ecules are linked by O-H⋯(O,N), N-H⋯O and C-H⋯O hydrogen bonds into sheets lying parallel to the bc plane. A weak aromatic π-π stacking inter-action is also observed [centroid-centroid distance = 3.7330 (7) Å].

Related literature

For background to the biological activity of hydrazones, see: Abdel-Aziz & Mekawey (2009 ▶). For a related structure, see: Rassem et al. (2012 ▶). For further synthetic details, see: Desai et al. (2000 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H14N2O4

M = 298.29

Monoclinic,

a = 12.2173 (7) Å

b = 7.8523 (5) Å

c = 15.6025 (9) Å

β = 108.577 (1)°

V = 1418.82 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.32 × 0.21 × 0.14 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.969, T max = 0.986

14301 measured reflections

4122 independent reflections

3463 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.124

S = 1.07

4122 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028735/hb6868sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028735/hb6868Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028735/hb6868Isup3.cml

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

C16H14N2O4	F(000) = 624
Mr = 298.29	Dx = 1.396 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5671 reflections
a = 12.2173 (7) Å	θ = 2.8–30.1°
b = 7.8523 (5) Å	µ = 0.10 mm−1
c = 15.6025 (9) Å	T = 100 K
β = 108.577 (1)°	Block, colourless
V = 1418.82 (15) Å3	0.32 × 0.21 × 0.14 mm
Z = 4

Bruker APEX DUO CCD diffractometer	4122 independent reflections
Radiation source: fine-focus sealed tube	3463 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 30.1°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→16
Tmin = 0.969, Tmax = 0.986	k = −11→10
14301 measured reflections	l = −22→22

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0673P)2 + 0.394P] where P = (Fo2 + 2Fc2)/3
4122 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.70132 (7)	0.06520 (12)	0.21655 (5)	0.0260 (2)
O2	0.35596 (7)	0.38508 (10)	−0.16701 (5)	0.01834 (17)
O3	0.48909 (8)	0.40025 (12)	−0.26386 (6)	0.0273 (2)
H1O3	0.5341	0.4088	−0.2982	0.033*
O4	0.35806 (9)	0.53387 (12)	−0.37939 (6)	0.0305 (2)
N1	0.64695 (7)	0.09189 (11)	0.06501 (6)	0.01427 (18)
N2	0.55352 (7)	0.18816 (11)	0.06821 (6)	0.01471 (18)
C1	0.88465 (10)	−0.14596 (14)	0.22331 (7)	0.0202 (2)
H1A	0.8587	−0.1404	0.2732	0.024*
C2	0.98417 (10)	−0.23668 (15)	0.22871 (9)	0.0262 (2)
H2A	1.0239	−0.2935	0.2818	0.031*
C3	1.02450 (10)	−0.24288 (17)	0.15531 (10)	0.0304 (3)
H3A	1.0920	−0.3018	0.1594	0.036*
C4	0.96375 (11)	−0.16065 (17)	0.07552 (10)	0.0299 (3)
H4A	0.9907	−0.1654	0.0261	0.036*
C5	0.86271 (10)	−0.07092 (15)	0.06869 (8)	0.0221 (2)
H5A	0.8220	−0.0170	0.0149	0.027*
C6	0.82339 (9)	−0.06286 (13)	0.14308 (7)	0.0162 (2)
C7	0.71940 (9)	0.03547 (13)	0.14467 (7)	0.01526 (19)
C8	0.49302 (8)	0.25514 (13)	−0.00687 (6)	0.01392 (19)
H8A	0.5128	0.2371	−0.0590	0.017*
C9	0.39275 (8)	0.36004 (13)	−0.01025 (6)	0.01350 (19)
C10	0.36525 (9)	0.40247 (14)	0.06745 (7)	0.0177 (2)
H10A	0.4114	0.3619	0.1233	0.021*
C11	0.27065 (10)	0.50378 (15)	0.06311 (7)	0.0220 (2)
H11A	0.2542	0.5322	0.1156	0.026*
C12	0.20069 (10)	0.56235 (15)	−0.02047 (7)	0.0206 (2)
H12A	0.1360	0.6278	−0.0239	0.025*
C13	0.22630 (9)	0.52432 (14)	−0.09895 (7)	0.0169 (2)
H13A	0.1793	0.5643	−0.1546	0.020*
C14	0.32297 (8)	0.42582 (13)	−0.09354 (6)	0.01383 (19)
C15	0.31286 (9)	0.48856 (14)	−0.24511 (7)	0.0180 (2)
H15A	0.3096	0.6062	−0.2272	0.022*
H15B	0.2352	0.4528	−0.2792	0.022*
C16	0.38970 (10)	0.47431 (14)	−0.30367 (7)	0.0196 (2)
H1N1	0.6582 (14)	0.066 (2)	0.0106 (11)	0.030 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0283 (4)	0.0379 (5)	0.0125 (3)	0.0126 (4)	0.0072 (3)	0.0028 (3)
O2	0.0218 (4)	0.0241 (4)	0.0112 (3)	0.0062 (3)	0.0082 (3)	0.0036 (3)
O3	0.0275 (4)	0.0309 (5)	0.0311 (4)	0.0042 (4)	0.0200 (4)	0.0053 (4)
O4	0.0533 (6)	0.0261 (4)	0.0172 (4)	0.0037 (4)	0.0184 (4)	0.0046 (3)
N1	0.0150 (4)	0.0165 (4)	0.0117 (4)	0.0012 (3)	0.0048 (3)	−0.0007 (3)
N2	0.0143 (4)	0.0158 (4)	0.0141 (4)	0.0005 (3)	0.0046 (3)	−0.0013 (3)
C1	0.0198 (5)	0.0167 (5)	0.0203 (5)	0.0007 (4)	0.0010 (4)	−0.0014 (4)
C2	0.0198 (5)	0.0185 (5)	0.0328 (6)	0.0023 (4)	−0.0023 (4)	−0.0009 (4)
C3	0.0182 (5)	0.0232 (6)	0.0491 (8)	0.0042 (4)	0.0097 (5)	−0.0008 (5)
C4	0.0269 (6)	0.0282 (6)	0.0414 (7)	0.0040 (5)	0.0202 (5)	−0.0003 (5)
C5	0.0216 (5)	0.0227 (5)	0.0247 (5)	0.0018 (4)	0.0111 (4)	0.0008 (4)
C6	0.0143 (4)	0.0145 (4)	0.0187 (5)	−0.0008 (4)	0.0037 (4)	−0.0016 (4)
C7	0.0160 (4)	0.0160 (4)	0.0138 (4)	−0.0006 (4)	0.0047 (3)	−0.0003 (3)
C8	0.0153 (4)	0.0142 (4)	0.0128 (4)	−0.0021 (3)	0.0051 (3)	−0.0007 (3)
C9	0.0147 (4)	0.0133 (4)	0.0127 (4)	−0.0022 (3)	0.0047 (3)	−0.0007 (3)
C10	0.0218 (5)	0.0194 (5)	0.0122 (4)	0.0003 (4)	0.0055 (4)	0.0000 (4)
C11	0.0273 (5)	0.0247 (5)	0.0170 (5)	0.0037 (4)	0.0114 (4)	−0.0021 (4)
C12	0.0206 (5)	0.0225 (5)	0.0214 (5)	0.0044 (4)	0.0103 (4)	−0.0003 (4)
C13	0.0164 (4)	0.0188 (5)	0.0157 (4)	0.0015 (4)	0.0051 (4)	0.0018 (4)
C14	0.0159 (4)	0.0152 (4)	0.0115 (4)	−0.0017 (3)	0.0059 (3)	−0.0007 (3)
C15	0.0187 (5)	0.0234 (5)	0.0120 (4)	0.0017 (4)	0.0050 (4)	0.0040 (4)
C16	0.0289 (6)	0.0170 (5)	0.0160 (4)	−0.0020 (4)	0.0117 (4)	−0.0007 (4)

O1—C7	1.2325 (12)	C5—C6	1.3918 (15)
O2—C14	1.3686 (11)	C5—H5A	0.9300
O2—C15	1.4191 (12)	C6—C7	1.4936 (14)
O3—C16	1.3107 (15)	C8—C9	1.4631 (14)
O3—H1O3	0.8843	C8—H8A	0.9300
O4—C16	1.2136 (13)	C9—C10	1.3975 (13)
N1—C7	1.3504 (13)	C9—C14	1.4059 (13)
N1—N2	1.3831 (11)	C10—C11	1.3869 (15)
N1—H1N1	0.924 (17)	C10—H10A	0.9300
N2—C8	1.2821 (13)	C11—C12	1.3901 (16)
C1—C2	1.3884 (16)	C11—H11A	0.9300
C1—C6	1.3985 (15)	C12—C13	1.3895 (14)
C1—H1A	0.9300	C12—H12A	0.9300
C2—C3	1.3843 (19)	C13—C14	1.3916 (14)
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.389 (2)	C15—C16	1.5084 (14)
C3—H3A	0.9300	C15—H15A	0.9700
C4—C5	1.3956 (16)	C15—H15B	0.9700
C4—H4A	0.9300
C14—O2—C15	117.23 (8)	C9—C8—H8A	120.1
C16—O3—H1O3	109.9	C10—C9—C14	118.14 (9)
C7—N1—N2	116.90 (8)	C10—C9—C8	122.20 (9)
C7—N1—H1N1	121.8 (10)	C14—C9—C8	119.62 (8)
N2—N1—H1N1	121.3 (10)	C11—C10—C9	121.42 (9)
C8—N2—N1	115.68 (8)	C11—C10—H10A	119.3
C2—C1—C6	120.16 (11)	C9—C10—H10A	119.3
C2—C1—H1A	119.9	C10—C11—C12	119.29 (9)
C6—C1—H1A	119.9	C10—C11—H11A	120.4
C3—C2—C1	120.23 (11)	C12—C11—H11A	120.4
C3—C2—H2A	119.9	C13—C12—C11	120.79 (10)
C1—C2—H2A	119.9	C13—C12—H12A	119.6
C2—C3—C4	119.72 (11)	C11—C12—H12A	119.6
C2—C3—H3A	120.1	C12—C13—C14	119.41 (9)
C4—C3—H3A	120.1	C12—C13—H13A	120.3
C3—C4—C5	120.67 (12)	C14—C13—H13A	120.3
C3—C4—H4A	119.7	O2—C14—C13	123.35 (9)
C5—C4—H4A	119.7	O2—C14—C9	115.76 (9)
C6—C5—C4	119.43 (11)	C13—C14—C9	120.88 (9)
C6—C5—H5A	120.3	O2—C15—C16	110.21 (9)
C4—C5—H5A	120.3	O2—C15—H15A	109.6
C5—C6—C1	119.78 (10)	C16—C15—H15A	109.6
C5—C6—C7	123.97 (9)	O2—C15—H15B	109.6
C1—C6—C7	116.22 (9)	C16—C15—H15B	109.6
O1—C7—N1	121.36 (9)	H15A—C15—H15B	108.1
O1—C7—C6	120.86 (9)	O4—C16—O3	126.30 (10)
N1—C7—C6	117.77 (9)	O4—C16—C15	119.63 (11)
N2—C8—C9	119.75 (8)	O3—C16—C15	114.03 (9)
N2—C8—H8A	120.1
C7—N1—N2—C8	172.93 (9)	N2—C8—C9—C14	−176.62 (9)
C6—C1—C2—C3	1.17 (17)	C14—C9—C10—C11	1.25 (16)
C1—C2—C3—C4	−1.25 (19)	C8—C9—C10—C11	179.21 (10)
C2—C3—C4—C5	0.4 (2)	C9—C10—C11—C12	0.95 (17)
C3—C4—C5—C6	0.59 (19)	C10—C11—C12—C13	−1.72 (18)
C4—C5—C6—C1	−0.67 (17)	C11—C12—C13—C14	0.25 (17)
C4—C5—C6—C7	177.28 (11)	C15—O2—C14—C13	20.08 (14)
C2—C1—C6—C5	−0.20 (16)	C15—O2—C14—C9	−160.56 (9)
C2—C1—C6—C7	−178.31 (10)	C12—C13—C14—O2	−178.65 (10)
N2—N1—C7—O1	1.68 (15)	C12—C13—C14—C9	2.02 (16)
N2—N1—C7—C6	−177.63 (8)	C10—C9—C14—O2	177.88 (9)
C5—C6—C7—O1	−165.87 (11)	C8—C9—C14—O2	−0.13 (14)
C1—C6—C7—O1	12.14 (15)	C10—C9—C14—C13	−2.74 (15)
C5—C6—C7—N1	13.44 (16)	C8—C9—C14—C13	179.25 (9)
C1—C6—C7—N1	−168.54 (9)	C14—O2—C15—C16	157.84 (9)
N1—N2—C8—C9	−179.66 (8)	O2—C15—C16—O4	169.40 (10)
N2—C8—C9—C10	5.46 (15)	O2—C15—C16—O3	−12.74 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O1i	0.88	1.99	2.7194 (14)	139
O3—H1O3···N2i	0.88	2.30	3.0464 (12)	142
N1—H1N1···O4ii	0.925 (17)	2.009 (16)	2.9131 (13)	165.4 (16)
C5—H5A···O4ii	0.93	2.55	3.4058 (16)	153
C11—H11A···O1iii	0.93	2.51	3.3791 (13)	155
C15—H15A···O1iv	0.97	2.59	3.5434 (15)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯O1i	0.88	1.99	2.7194 (14)	139
O3—H1O3⋯N2i	0.88	2.30	3.0464 (12)	142
N1—H1N1⋯O4ii	0.925 (17)	2.009 (16)	2.9131 (13)	165.4 (16)
C5—H5A⋯O4ii	0.93	2.55	3.4058 (16)	153
C11—H11A⋯O1iii	0.93	2.51	3.3791 (13)	155
C15—H15A⋯O1iv	0.97	2.59	3.5434 (15)	167

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .