organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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[Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678-1680.]). For bond lengths and angles in other hydrazone derivatives, see: Bakir & Gyles (2003[Bakir, M. & Gyles, C. (2003). J. Mol. Struct. 649, 133-135.]); Baughman et al. (2004[Baughman, R. G., Martin, K. L., Singh, R. K. & Stoffer, J. O. (2004). Acta Cryst. C60, o103-o106.]); Ohba (1996[Ohba, S. (1996). Acta Cryst. C52, 2118-2119.]); Yao & Jing (2007[Yao, X.-L. & Jing, Z.-L. (2007). Acta Cryst. E63, o3900.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14N2O5

  • Mr = 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[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.977

  • 39211 measured reflections

  • 3626 independent reflections

  • 2988 reflections with I > 2σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL, ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

All H atoms were positioned geometrically and refined as riding with C—H=0.93 (aromatic), 0.97(methylene), 0.96 Å(methyl) and N—H=0.86 Å, with Uiso(H)=1.2Ueq(CH, CH2 or NH) and Uiso(H)=1.5Ueq(C).

In the absence of significant anomalous scattering, the absolute structure could not be reliably determined and then any references to the Flack parameter were removed.

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
[Figure 1] 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.
[Figure 2] 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
C15H14N2O5F(000) = 632
Mr = 302.28Dx = 1.387 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2890 reflections
a = 4.9987 (2) Åθ = 2.8–25.0°
b = 13.4200 (5) ŵ = 0.11 mm1
c = 21.5876 (8) ÅT = 296 K
V = 1448.15 (10) Å3Block, colorless
Z = 40.21 × 0.19 × 0.18 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3626 independent reflections
Radiation source: fine-focus sealed tube2988 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω scansθmax = 28.4°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 66
Tmin = 0.973, Tmax = 0.977k = 1717
39211 measured reflectionsl = 2828
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-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 reflectionsΔρmax = 0.17 e Å3
200 parametersΔρmin = 0.12 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.014 (2)
Crystal data top
C15H14N2O5V = 1448.15 (10) Å3
Mr = 302.28Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 4.9987 (2) ŵ = 0.11 mm1
b = 13.4200 (5) ÅT = 296 K
c = 21.5876 (8) Å0.21 × 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)
Tmin = 0.973, Tmax = 0.977Rint = 0.037
39211 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.105H-atom parameters constrained
S = 1.04Δρmax = 0.17 e Å3
3626 reflectionsΔρmin = 0.12 e Å3
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
xyzUiso*/Ueq
N20.1299 (3)0.82093 (8)0.14030 (6)0.0421 (3)
N10.1018 (3)0.91747 (9)0.16153 (6)0.0457 (3)
H1A0.04980.94730.15830.055*
O40.0888 (3)0.40544 (8)0.00497 (5)0.0589 (3)
O10.4391 (3)1.11568 (9)0.23940 (6)0.0614 (3)
O30.2649 (3)0.44319 (8)0.09449 (6)0.0607 (3)
O20.5320 (2)0.92740 (9)0.19504 (6)0.0548 (3)
C50.3114 (3)0.96497 (10)0.18735 (7)0.0399 (3)
C90.1023 (4)0.51982 (10)0.07856 (7)0.0452 (3)
C80.1028 (3)0.61391 (10)0.10565 (7)0.0433 (3)
H8A0.22450.62850.13700.052*
C60.0733 (3)0.78742 (11)0.11141 (7)0.0432 (3)
H6A0.22220.82820.10630.052*
C70.0777 (3)0.68616 (10)0.08613 (7)0.0420 (3)
C100.0806 (4)0.50087 (11)0.03118 (7)0.0474 (4)
C40.2508 (3)1.06823 (10)0.20534 (7)0.0428 (3)
O50.2054 (4)0.45208 (11)0.06712 (7)0.0836 (5)
C120.2646 (4)0.66377 (12)0.04072 (8)0.0505 (4)
H12A0.39100.71110.02910.061*
C110.2631 (4)0.57083 (12)0.01263 (7)0.0525 (4)
H11A0.38510.55610.01860.063*
C30.0474 (4)1.12983 (14)0.19440 (10)0.0670 (5)
H3A0.10641.11570.17180.080*
C140.0652 (4)0.38936 (12)0.04507 (8)0.0552 (4)
C20.1111 (5)1.22134 (14)0.22389 (11)0.0748 (6)
H2B0.00641.27860.22470.090*
C150.0306 (6)0.28530 (14)0.06886 (9)0.0775 (6)
H15A0.14230.27570.10450.116*
H15B0.15310.27490.08010.116*
H15C0.08030.23870.03720.116*
C130.4284 (5)0.45684 (14)0.14794 (9)0.0655 (5)
H13A0.53390.39810.15470.098*
H13B0.31680.46870.18340.098*
H13C0.54440.51290.14170.098*
C10.3456 (5)1.20943 (13)0.24976 (9)0.0657 (5)
H1B0.43581.25820.27210.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0475 (7)0.0290 (5)0.0499 (6)0.0012 (5)0.0038 (5)0.0045 (5)
N10.0406 (6)0.0314 (6)0.0650 (8)0.0019 (5)0.0017 (6)0.0106 (6)
O40.0856 (9)0.0378 (6)0.0534 (6)0.0175 (6)0.0034 (6)0.0124 (5)
O10.0652 (8)0.0464 (6)0.0725 (8)0.0082 (6)0.0158 (7)0.0114 (6)
O30.0807 (8)0.0366 (5)0.0648 (7)0.0077 (6)0.0113 (7)0.0101 (5)
O20.0457 (6)0.0441 (6)0.0746 (8)0.0061 (5)0.0080 (6)0.0052 (5)
C50.0438 (8)0.0336 (7)0.0424 (7)0.0003 (6)0.0013 (6)0.0016 (5)
C90.0554 (9)0.0327 (7)0.0474 (8)0.0036 (6)0.0012 (7)0.0045 (6)
C80.0485 (8)0.0353 (7)0.0460 (7)0.0037 (6)0.0013 (6)0.0068 (6)
C60.0444 (7)0.0354 (7)0.0498 (8)0.0016 (6)0.0015 (7)0.0050 (6)
C70.0469 (8)0.0353 (7)0.0439 (7)0.0050 (6)0.0033 (6)0.0034 (6)
C100.0622 (10)0.0349 (7)0.0451 (8)0.0106 (7)0.0036 (7)0.0079 (6)
C40.0462 (8)0.0349 (7)0.0475 (8)0.0037 (6)0.0005 (6)0.0056 (6)
O50.1165 (13)0.0615 (8)0.0730 (9)0.0209 (9)0.0306 (9)0.0194 (7)
C120.0532 (9)0.0444 (8)0.0539 (9)0.0024 (7)0.0056 (7)0.0015 (7)
C110.0616 (10)0.0474 (8)0.0483 (8)0.0122 (8)0.0087 (7)0.0041 (7)
C30.0597 (10)0.0470 (9)0.0944 (14)0.0113 (8)0.0142 (11)0.0217 (9)
C140.0775 (11)0.0424 (8)0.0457 (8)0.0024 (8)0.0066 (8)0.0082 (7)
C20.0847 (15)0.0432 (9)0.0965 (15)0.0123 (10)0.0050 (13)0.0206 (10)
C150.1201 (18)0.0464 (9)0.0660 (11)0.0009 (11)0.0085 (12)0.0196 (9)
C130.0848 (13)0.0467 (9)0.0648 (11)0.0133 (9)0.0169 (10)0.0028 (8)
C10.0883 (14)0.0406 (9)0.0682 (11)0.0136 (9)0.0057 (11)0.0161 (8)
Geometric parameters (Å, º) top
N2—C61.2742 (19)C10—C111.369 (3)
N2—N11.3814 (16)C4—C31.331 (2)
N1—C51.3471 (19)O5—C141.194 (2)
N1—H1A0.8600C12—C111.387 (2)
O4—C141.344 (2)C12—H12A0.9300
O4—C101.4007 (17)C11—H11A0.9300
O1—C41.3537 (18)C3—C21.419 (3)
O1—C11.361 (2)C3—H3A0.9300
O3—C91.355 (2)C14—C151.498 (2)
O3—C131.426 (2)C2—C11.308 (3)
O2—C51.2242 (18)C2—H2B0.9300
C5—C41.4706 (19)C15—H15A0.9600
C9—C81.3915 (19)C15—H15B0.9600
C9—C101.395 (2)C15—H15C0.9600
C8—C71.390 (2)C13—H13A0.9600
C8—H8A0.9300C13—H13B0.9600
C6—C71.4644 (19)C13—H13C0.9600
C6—H6A0.9300C1—H1B0.9300
C7—C121.387 (2)
C6—N2—N1114.35 (12)C11—C12—H12A120.0
C5—N1—N2120.13 (12)C7—C12—H12A120.0
C5—N1—H1A119.9C10—C11—C12119.52 (15)
N2—N1—H1A119.9C10—C11—H11A120.2
C14—O4—C10117.05 (13)C12—C11—H11A120.2
C4—O1—C1106.58 (15)C4—C3—C2106.64 (17)
C9—O3—C13116.85 (12)C4—C3—H3A126.7
O2—C5—N1124.19 (13)C2—C3—H3A126.7
O2—C5—C4122.54 (14)O5—C14—O4122.91 (15)
N1—C5—C4113.27 (13)O5—C14—C15126.03 (19)
O3—C9—C8125.51 (15)O4—C14—C15111.05 (17)
O3—C9—C10116.14 (13)C1—C2—C3106.66 (18)
C8—C9—C10118.34 (15)C1—C2—H2B126.7
C7—C8—C9120.29 (15)C3—C2—H2B126.7
C7—C8—H8A119.9C14—C15—H15A109.5
C9—C8—H8A119.9C14—C15—H15B109.5
N2—C6—C7121.46 (14)H15A—C15—H15B109.5
N2—C6—H6A119.3C14—C15—H15C109.5
C7—C6—H6A119.3H15A—C15—H15C109.5
C12—C7—C8120.03 (13)H15B—C15—H15C109.5
C12—C7—C6118.33 (14)O3—C13—H13A109.5
C8—C7—C6121.63 (14)O3—C13—H13B109.5
C11—C10—C9121.73 (13)H13A—C13—H13B109.5
C11—C10—O4119.31 (15)O3—C13—H13C109.5
C9—C10—O4118.82 (15)H13A—C13—H13C109.5
C3—C4—O1109.59 (13)H13B—C13—H13C109.5
C3—C4—C5134.06 (15)C2—C1—O1110.52 (17)
O1—C4—C5116.33 (13)C2—C1—H1B124.7
C11—C12—C7120.00 (16)O1—C1—H1B124.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.252.9414 (18)137
C1—H1B···O2ii0.932.383.217 (2)149
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H14N2O5
Mr302.28
Crystal system, space groupOrthorhombic, P212121
Temperature (K)296
a, b, c (Å)4.9987 (2), 13.4200 (5), 21.5876 (8)
V3)1448.15 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.21 × 0.19 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax0.973, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections
39211, 3626, 2988
Rint0.037
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.105, 1.04
No. of reflections3626
No. of parameters200
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.252.9414 (18)137
C1—H1B···O2ii0.932.383.217 (2)149
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1/2, z+1/2.
 

References

First citationBakir, M. & Gyles, C. (2003). J. Mol. Struct. 649, 133–135.  Web of Science CSD CrossRef CAS
First citationBaughman, 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
First citationBruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBurnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
First citationOhba, S. (1996). Acta Cryst. C52, 2118–2119.  CSD CrossRef CAS Web of Science IUCr Journals
First citationOkabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678–1680.  CSD CrossRef CAS Web of Science IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationYao, X.-L. & Jing, Z.-L. (2007). Acta Cryst. E63, o3900.  Web of Science CSD CrossRef IUCr Journals

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