(E)-4-{[2-(2-Furylcarbon­yl)hydrazinyl­idene]meth­yl}-2-meth­oxy­phenyl acetate

Xu, J.; Yue, X.

doi:10.1107/S1600536811008932

organic compounds

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doi:10.1107/S1600536811008932

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(E)-4-{[2-(2-Furylcarbonyl)hydrazinylidene]methyl}-2-methoxyphenyl acetate

Jun Xu ^a ^* and Xiao-yu Yue ^a

^aDepartment of Quality Detection and Management, Zhengzhou College of Animal Husbandry Engineering, Zhengzhou 450011, People's Republic of China
^*Correspondence e-mail: xujun20101996@yahoo.com.cn

(Received 4 March 2011; accepted 9 March 2011; online 15 March 2011)

The molecule of the title Schiff base compound, C₁₅H₁₄N₂O₅, was obtained from a condensation reaction of 4-acetoxy-3-methoxybenzaldehyde and 2-furylcarbonylhydrazide. In the molecule, the furyl ring makes a dihedral angle of 14.63 (10)° with the benzene ring. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains along the b axis. Futhermore, weak C—H⋯O interactions 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_r = 302.28
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.105
S = 1.04
3626 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.12 e Å⁻³

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) x-1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Several phenylhydrazone derivatives have been shown to be potentially DNA-damaging and are mutagenic agents (Okabe et al. 1993). As part of our ongoing studies of Schiff bases, in this paper, we have synthesized the title compound and report the crystal structure.

The molecule adopts an E geometry with respect to the C=N bond (Fig. 1). The molecule is not planar, the dihedral angle between the furyl ring and the benzene ring is 14.63 (10)°, Bond lengths and bond angles agree with those of other hydrazone derivatives (Ohba, 1996; Baughman et al., 2004; Yao & Jing et al., 2007; Bakir & Gyles, 2003)

In the Crystal, Intermolecular N—H···O hydrogen bond link the molecules to form chains along the b axis. The chains are further connected to form corrugated layers parallel to the (0 0 1) plane (Table 1, Fig. 2).

Related literature top

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 top

Furan-2-carbohydrazine (1 mmol, 0.126 g) was dissolved in anhydrous ethanol (10 ml), The mixture was stirred for several minitutes at 351k, 4-acetoxy-3-methoxybenzaldehyde (1 mmol, 0.194 g) in ethanol (10 mm l) was added dropwise and the mixture was stirred at refluxing temperature for 3 h. The product was isolated and recrystallized from DMF, single crystals of (I) was obtained after one month.

Computing details top

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

Figures top

	Fig. 1. Molecular view of (I) with the atom labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Packing view of (I) projected down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity.

(E)-4-{[2-(2-Furylcarbonyl)hydrazinylidene]methyl}-2-methoxyphenyl acetate top

Crystal data top

C₁₅H₁₄N₂O₅	F(000) = 632
M_r = 302.28	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0588P)² + 0.1124P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3626 reflections	Δρ_max = 0.17 e Å⁻³
200 parameters	Δρ_min = −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)

Crystal data top

C₁₅H₁₄N₂O₅	V = 1448.15 (10) Å³
M_r = 302.28	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.9987 (2) Å	µ = 0.11 mm⁻¹
b = 13.4200 (5) Å	T = 296 K
c = 21.5876 (8) Å	0.21 × 0.19 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3626 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2988 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.977	R_int = 0.037
39211 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.04	Δρ_max = 0.17 e Å⁻³
3626 reflections	Δρ_min = −0.12 e Å⁻³
200 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z; (ii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₅
M_r	302.28
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	4.9987 (2), 13.4200 (5), 21.5876 (8)
V (Å³)	1448.15 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.21 × 0.19 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.973, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	39211, 3626, 2988
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.105, 1.04
No. of reflections	3626
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.12

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), XP in SHELXTL (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z; (ii) −x+1, y+1/2, −z+1/2.

References

Bakir, M. & Gyles, C. (2003). J. Mol. Struct. 649, 133–135. Web of Science CSD CrossRef CAS Google Scholar
Baughman, R. G., Martin, K. L., Singh, R. K. & Stoffer, J. O. (2004). Acta Cryst. C60, o103–o106. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Ohba, S. (1996). Acta Cryst. C52, 2118–2119. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678–1680. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yao, X.-L. & Jing, Z.-L. (2007). Acta Cryst. E63, o3900. Web of Science CSD CrossRef IUCr Journals Google Scholar

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(E)-4-{[2-(2-Furylcarbon­yl)hydrazinyl­­idene]meth­yl}-2-meth­­oxy­phenyl acetate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(E)-4-{[2-(2-Furylcarbonyl)hydrazinylidene]methyl}-2-methoxyphenyl acetate