(E)-4-{[2-(2-Furylcarbon-yl)hydrazinyl-idene]meth-yl}-2-meth-oxy-phenyl acetate.

The mol-ecule of the title Schiff base compound, C(15)H(14)N(2)O(5), was obtained from a condensation reaction of 4-acet-oxy-3-meth-oxy-benzaldehyde and 2-furyl-carbonyl-hydrazide. In the mol-ecule, the furyl ring makes a dihedral angle of 14.63 (10)° with the benzene ring. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains along the b axis. Futhermore, weak C-H⋯O inter-actions connect the chains, forming corrugated layers parallel to (001). The dihedral angle between the rings is 14.63 (10)°.

Related literature

Several phenyl­hydrazone derivatives have been shown to be potentially DNA-damaging and are mutagenic agents, see: Okabe et al. (1993 ▶). For bond lengths and angles in other hydrazone derivatives, see: Bakir & Gyles (2003 ▶); Baughman et al. (2004 ▶); Ohba (1996 ▶); Yao & Jing (2007 ▶).

Experimental

Crystal data

C15H14N2O5

M = 302.28

Orthorhombic,

a = 4.9987 (2) Å

b = 13.4200 (5) Å

c = 21.5876 (8) Å

V = 1448.15 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.21 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.973, T max = 0.977

39211 measured reflections

3626 independent reflections

2988 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.105

S = 1.04

3626 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.12 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL, ORTEPIII (Burnett & Johnson, 1996 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008932/dn2664sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008932/dn2664Isup2.hkl

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

C15H14N2O5	F(000) = 632
Mr = 302.28	Dx = 1.387 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2890 reflections
a = 4.9987 (2) Å	θ = 2.8–25.0°
b = 13.4200 (5) Å	µ = 0.11 mm−1
c = 21.5876 (8) Å	T = 296 K
V = 1448.15 (10) Å3	Block, colorless
Z = 4	0.21 × 0.19 × 0.18 mm

Bruker SMART CCD area-detector diffractometer	3626 independent reflections
Radiation source: fine-focus sealed tube	2988 reflections with I > 2σ(I)
graphite	Rint = 0.037
ω scans	θmax = 28.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −6→6
Tmin = 0.973, Tmax = 0.977	k = −17→17
39211 measured reflections	l = −28→28

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0588P)2 + 0.1124P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3626 reflections	Δρmax = 0.17 e Å−3
200 parameters	Δρmin = −0.12 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (2)

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
N2	0.1299 (3)	0.82093 (8)	0.14030 (6)	0.0421 (3)
N1	0.1018 (3)	0.91747 (9)	0.16153 (6)	0.0457 (3)
H1A	−0.0498	0.9473	0.1583	0.055*
O4	−0.0888 (3)	0.40544 (8)	0.00497 (5)	0.0589 (3)
O1	0.4391 (3)	1.11568 (9)	0.23940 (6)	0.0614 (3)
O3	0.2649 (3)	0.44319 (8)	0.09449 (6)	0.0607 (3)
O2	0.5320 (2)	0.92740 (9)	0.19504 (6)	0.0548 (3)
C5	0.3114 (3)	0.96497 (10)	0.18735 (7)	0.0399 (3)
C9	0.1023 (4)	0.51982 (10)	0.07856 (7)	0.0452 (3)
C8	0.1028 (3)	0.61391 (10)	0.10565 (7)	0.0433 (3)
H8A	0.2245	0.6285	0.1370	0.052*
C6	−0.0733 (3)	0.78742 (11)	0.11141 (7)	0.0432 (3)
H6A	−0.2222	0.8282	0.1063	0.052*
C7	−0.0777 (3)	0.68616 (10)	0.08613 (7)	0.0420 (3)
C10	−0.0806 (4)	0.50087 (11)	0.03118 (7)	0.0474 (4)
C4	0.2508 (3)	1.06823 (10)	0.20534 (7)	0.0428 (3)
O5	0.2054 (4)	0.45208 (11)	−0.06712 (7)	0.0836 (5)
C12	−0.2646 (4)	0.66377 (12)	0.04072 (8)	0.0505 (4)
H12A	−0.3910	0.7111	0.0291	0.061*
C11	−0.2631 (4)	0.57083 (12)	0.01263 (7)	0.0525 (4)
H11A	−0.3851	0.5561	−0.0186	0.063*
C3	0.0474 (4)	1.12983 (14)	0.19440 (10)	0.0670 (5)
H3A	−0.1064	1.1157	0.1718	0.080*
C14	0.0652 (4)	0.38936 (12)	−0.04507 (8)	0.0552 (4)
C2	0.1111 (5)	1.22134 (14)	0.22389 (11)	0.0748 (6)
H2B	0.0064	1.2786	0.2247	0.090*
C15	0.0306 (6)	0.28530 (14)	−0.06886 (9)	0.0775 (6)
H15A	0.1423	0.2757	−0.1045	0.116*
H15B	−0.1531	0.2749	−0.0801	0.116*
H15C	0.0803	0.2387	−0.0372	0.116*
C13	0.4284 (5)	0.45684 (14)	0.14794 (9)	0.0655 (5)
H13A	0.5339	0.3981	0.1547	0.098*
H13B	0.3168	0.4687	0.1834	0.098*
H13C	0.5444	0.5129	0.1417	0.098*
C1	0.3456 (5)	1.20943 (13)	0.24976 (9)	0.0657 (5)
H1B	0.4358	1.2582	0.2721	0.079*

	U11	U22	U33	U12	U13	U23
N2	0.0475 (7)	0.0290 (5)	0.0499 (6)	0.0012 (5)	0.0038 (5)	−0.0045 (5)
N1	0.0406 (6)	0.0314 (6)	0.0650 (8)	0.0019 (5)	−0.0017 (6)	−0.0106 (6)
O4	0.0856 (9)	0.0378 (6)	0.0534 (6)	−0.0175 (6)	0.0034 (6)	−0.0124 (5)
O1	0.0652 (8)	0.0464 (6)	0.0725 (8)	−0.0082 (6)	−0.0158 (7)	−0.0114 (6)
O3	0.0807 (8)	0.0366 (5)	0.0648 (7)	0.0077 (6)	−0.0113 (7)	−0.0101 (5)
O2	0.0457 (6)	0.0441 (6)	0.0746 (8)	0.0061 (5)	−0.0080 (6)	−0.0052 (5)
C5	0.0438 (8)	0.0336 (7)	0.0424 (7)	0.0003 (6)	0.0013 (6)	−0.0016 (5)
C9	0.0554 (9)	0.0327 (7)	0.0474 (8)	−0.0036 (6)	0.0012 (7)	−0.0045 (6)
C8	0.0485 (8)	0.0353 (7)	0.0460 (7)	−0.0037 (6)	−0.0013 (6)	−0.0068 (6)
C6	0.0444 (7)	0.0354 (7)	0.0498 (8)	0.0016 (6)	0.0015 (7)	−0.0050 (6)
C7	0.0469 (8)	0.0353 (7)	0.0439 (7)	−0.0050 (6)	0.0033 (6)	−0.0034 (6)
C10	0.0622 (10)	0.0349 (7)	0.0451 (8)	−0.0106 (7)	0.0036 (7)	−0.0079 (6)
C4	0.0462 (8)	0.0349 (7)	0.0475 (8)	−0.0037 (6)	−0.0005 (6)	−0.0056 (6)
O5	0.1165 (13)	0.0615 (8)	0.0730 (9)	−0.0209 (9)	0.0306 (9)	−0.0194 (7)
C12	0.0532 (9)	0.0444 (8)	0.0539 (9)	−0.0024 (7)	−0.0056 (7)	−0.0015 (7)
C11	0.0616 (10)	0.0474 (8)	0.0483 (8)	−0.0122 (8)	−0.0087 (7)	−0.0041 (7)
C3	0.0597 (10)	0.0470 (9)	0.0944 (14)	0.0113 (8)	−0.0142 (11)	−0.0217 (9)
C14	0.0775 (11)	0.0424 (8)	0.0457 (8)	−0.0024 (8)	−0.0066 (8)	−0.0082 (7)
C2	0.0847 (15)	0.0432 (9)	0.0965 (15)	0.0123 (10)	0.0050 (13)	−0.0206 (10)
C15	0.1201 (18)	0.0464 (9)	0.0660 (11)	−0.0009 (11)	−0.0085 (12)	−0.0196 (9)
C13	0.0848 (13)	0.0467 (9)	0.0648 (11)	0.0133 (9)	−0.0169 (10)	−0.0028 (8)
C1	0.0883 (14)	0.0406 (9)	0.0682 (11)	−0.0136 (9)	0.0057 (11)	−0.0161 (8)

N2—C6	1.2742 (19)	C10—C11	1.369 (3)
N2—N1	1.3814 (16)	C4—C3	1.331 (2)
N1—C5	1.3471 (19)	O5—C14	1.194 (2)
N1—H1A	0.8600	C12—C11	1.387 (2)
O4—C14	1.344 (2)	C12—H12A	0.9300
O4—C10	1.4007 (17)	C11—H11A	0.9300
O1—C4	1.3537 (18)	C3—C2	1.419 (3)
O1—C1	1.361 (2)	C3—H3A	0.9300
O3—C9	1.355 (2)	C14—C15	1.498 (2)
O3—C13	1.426 (2)	C2—C1	1.308 (3)
O2—C5	1.2242 (18)	C2—H2B	0.9300
C5—C4	1.4706 (19)	C15—H15A	0.9600
C9—C8	1.3915 (19)	C15—H15B	0.9600
C9—C10	1.395 (2)	C15—H15C	0.9600
C8—C7	1.390 (2)	C13—H13A	0.9600
C8—H8A	0.9300	C13—H13B	0.9600
C6—C7	1.4644 (19)	C13—H13C	0.9600
C6—H6A	0.9300	C1—H1B	0.9300
C7—C12	1.387 (2)
C6—N2—N1	114.35 (12)	C11—C12—H12A	120.0
C5—N1—N2	120.13 (12)	C7—C12—H12A	120.0
C5—N1—H1A	119.9	C10—C11—C12	119.52 (15)
N2—N1—H1A	119.9	C10—C11—H11A	120.2
C14—O4—C10	117.05 (13)	C12—C11—H11A	120.2
C4—O1—C1	106.58 (15)	C4—C3—C2	106.64 (17)
C9—O3—C13	116.85 (12)	C4—C3—H3A	126.7
O2—C5—N1	124.19 (13)	C2—C3—H3A	126.7
O2—C5—C4	122.54 (14)	O5—C14—O4	122.91 (15)
N1—C5—C4	113.27 (13)	O5—C14—C15	126.03 (19)
O3—C9—C8	125.51 (15)	O4—C14—C15	111.05 (17)
O3—C9—C10	116.14 (13)	C1—C2—C3	106.66 (18)
C8—C9—C10	118.34 (15)	C1—C2—H2B	126.7
C7—C8—C9	120.29 (15)	C3—C2—H2B	126.7
C7—C8—H8A	119.9	C14—C15—H15A	109.5
C9—C8—H8A	119.9	C14—C15—H15B	109.5
N2—C6—C7	121.46 (14)	H15A—C15—H15B	109.5
N2—C6—H6A	119.3	C14—C15—H15C	109.5
C7—C6—H6A	119.3	H15A—C15—H15C	109.5
C12—C7—C8	120.03 (13)	H15B—C15—H15C	109.5
C12—C7—C6	118.33 (14)	O3—C13—H13A	109.5
C8—C7—C6	121.63 (14)	O3—C13—H13B	109.5
C11—C10—C9	121.73 (13)	H13A—C13—H13B	109.5
C11—C10—O4	119.31 (15)	O3—C13—H13C	109.5
C9—C10—O4	118.82 (15)	H13A—C13—H13C	109.5
C3—C4—O1	109.59 (13)	H13B—C13—H13C	109.5
C3—C4—C5	134.06 (15)	C2—C1—O1	110.52 (17)
O1—C4—C5	116.33 (13)	C2—C1—H1B	124.7
C11—C12—C7	120.00 (16)	O1—C1—H1B	124.7

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.25	2.9414 (18)	137
C1—H1B···O2ii	0.93	2.38	3.217 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.25	2.9414 (18)	137
C1—H1B⋯O2ii	0.93	2.38	3.217 (2)	149

Symmetry codes: (i) ; (ii) .