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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

4-Meth­­oxy-N′-(2-meth­oxy­benzyl­­idene)benzohydrazide

aDepartment of Chemistry, Baicheng Normal College, Baicheng 137000, People's Republic of China
*Correspondence e-mail: xinyou_zhang@126.com

(Received 10 May 2009; accepted 20 May 2009; online 23 May 2009)

In the title compound, C16H16N2O3, the two benzene rings are inclined to one another by 75.4 (2)°, and the mol­ecule adopts an E configuration about the C=N bond. In the crystal structure, symmetry-related mol­ecules are linked via inter­molecular N—H⋯O hydrogen bonds, forming chains running parallel to the c axis.

Related literature

For related structures, see: Alhadi et al. (2008[Alhadi, A. A., Ali, H. M., Puvaneswary, S., Robinson, W. T. & Ng, S. W. (2008). Acta Cryst. E64, o1584.]), Küçükgüzel et al. (2003[Küçükgüzel, S. G., Mazi, A., Sahin, F., Öztürk, S. & Stables, J. (2003). Eur. J. Med. Chem. 38, 1005-1013.]); Mohd Lair et al. (2009a[Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009a). Acta Cryst. E65, o189.],b[Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009b). Acta Cryst. E65, o190.]); Li et al. (2009[Li, M.-L., Huang, X. & Feng, R.-K. (2009). Acta Cryst. E65, o369.]); Zhang et al. (2009[Zhang, M.-J., Yin, L.-Z., Wang, D.-C., Deng, X.-M. & Liu, J.-B. (2009). Acta Cryst. E65, o508.]). For reference structural data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16N2O3

  • Mr = 284.31

  • Monoclinic, P 21 /c

  • a = 12.705 (1) Å

  • b = 16.053 (2) Å

  • c = 7.718 (1) Å

  • β = 107.233 (2)°

  • V = 1503.5 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 K

  • 0.20 × 0.20 × 0.18 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.983, Tmax = 0.984

  • 8570 measured reflections

  • 3007 independent reflections

  • 1574 reflections with I > 2σ(I)

  • Rint = 0.050

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.123

  • S = 0.98

  • 3007 reflections

  • 195 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.13 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯O2i 0.898 (9) 1.985 (11) 2.859 (2) 164 (2)
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Hydrazone compounds are readily synthesized by the reaction of aldehydes with hydrazides. Recently, a large number of such compounds have been reported on (Alhadi et al., 2008; Küçükgüzel et al., 2003; Li et al., 2009; Zhang et al., 2009). In continuation of work in this area we report herein on the crystal structure of the title compound, a new hydrazone compound synthesized from the reaction of equimolar quantities of 2-methoxybenzaldehyde with 4-methoxybenzohydrazide in methanol.

The molecule structure of the title compound is illustrated in Fig. 1. The molecule adopts an E configuration about the CN bond. The dihedral angle involving the two benzene rings is 75.4 (2)°. All the bond lengths are within normal values (Allen et al., 1987) and are comparable with those observed in the similar compounds (Mohd Lair et al., 2009a,b).

In the crystal structure of the compound, symmetry related molecules are linked through intermolecular N–H···O and N–H···N hydrogen bonds, forming chains running along the c axis (Table 1 and Fig. 2).

Related literature top

For related structures, see: Alhadi et al. (2008), Küçükgüzel et al. (2003); Mohd Lair et al. (2009a,b); Li et al. (2009); Zhang et al. (2009). For reference structural data, see: Allen et al. (1987).

Experimental top

2-Methoxybenzaldehyde (1.0 mmol, 136.2 mg) and 4-methoxybenzohydrazide (1.0 mmol, 166.2 mg) were mixed in a methanol solution, and the mixture was refluxed for 1 h. Colorless block-shaped crystals of the title compound were formed by slow evaporation of the solution in air.

Refinement top

Atom H2 attached to N2 was located from a difference Fourier map and freely refined with Uiso(H) restrained to 0.08 Å2. The C-bound H-atoms were included in calculated positions and refined as riding atoms: d(C–H) = 0.93–0.96 Å, with Uiso(H) = 1.2Ueq(C), or 1.5Ueq(Cmethyl).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probabilty level.
[Figure 2] Fig. 2. A view along the b axis of the crystal packing of the title compound, with hydrogen bonds shown as dashed lines (see Table 1 for details). H-atoms not involved in hydrogen bonding have been omitted for clarity.
4-Methoxy-N'-(2-methoxybenzylidene)benzohydrazide top
Crystal data top
C16H16N2O3F(000) = 600
Mr = 284.31Dx = 1.256 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1023 reflections
a = 12.705 (1) Åθ = 2.5–24.6°
b = 16.053 (2) ŵ = 0.09 mm1
c = 7.718 (1) ÅT = 298 K
β = 107.233 (2)°Block, colorless
V = 1503.5 (3) Å30.20 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3007 independent reflections
Radiation source: fine-focus sealed tube1574 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
ω scansθmax = 26.2°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1513
Tmin = 0.983, Tmax = 0.984k = 1917
8570 measured reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 0.98 w = 1/[σ2(Fo2) + (0.0515P)2]
where P = (Fo2 + 2Fc2)/3
3007 reflections(Δ/σ)max < 0.001
195 parametersΔρmax = 0.13 e Å3
1 restraintΔρmin = 0.19 e Å3
Crystal data top
C16H16N2O3V = 1503.5 (3) Å3
Mr = 284.31Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.705 (1) ŵ = 0.09 mm1
b = 16.053 (2) ÅT = 298 K
c = 7.718 (1) Å0.20 × 0.20 × 0.18 mm
β = 107.233 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3007 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1574 reflections with I > 2σ(I)
Tmin = 0.983, Tmax = 0.984Rint = 0.050
8570 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0491 restraint
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 0.98Δρmax = 0.13 e Å3
3007 reflectionsΔρmin = 0.19 e Å3
195 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
N10.11626 (13)0.25479 (11)0.8800 (2)0.0459 (5)
N20.20751 (14)0.23123 (11)0.8290 (2)0.0464 (5)
O10.00123 (13)0.47737 (10)0.7280 (2)0.0698 (5)
O20.27806 (12)0.16021 (9)1.0915 (2)0.0572 (4)
O30.62405 (13)0.06696 (12)0.6746 (2)0.0832 (6)
C10.03802 (17)0.34548 (14)0.8236 (3)0.0484 (6)
C20.07099 (18)0.42835 (15)0.7881 (3)0.0532 (6)
C30.1678 (2)0.45577 (18)0.8150 (3)0.0689 (8)
H30.19000.51080.79060.083*
C40.2316 (2)0.4011 (2)0.8783 (3)0.0777 (8)
H40.29700.41990.89580.093*
C50.2007 (2)0.3201 (2)0.9158 (4)0.0782 (8)
H50.24400.28380.95930.094*
C60.10359 (18)0.29291 (16)0.8878 (3)0.0629 (7)
H60.08210.23780.91300.075*
C70.06430 (17)0.31710 (14)0.7935 (3)0.0477 (6)
H70.09180.34480.71030.057*
C80.28308 (17)0.18075 (13)0.9401 (3)0.0456 (5)
C90.37276 (17)0.15184 (13)0.8685 (3)0.0467 (6)
C100.47380 (19)0.13301 (16)0.9881 (3)0.0693 (7)
H100.48440.13931.11190.083*
C110.5597 (2)0.10505 (18)0.9289 (4)0.0772 (8)
H110.62760.09321.01210.093*
C120.54480 (19)0.09484 (15)0.7470 (3)0.0598 (7)
C130.44375 (19)0.11214 (15)0.6249 (3)0.0620 (7)
H130.43300.10450.50140.074*
C140.35890 (17)0.14068 (13)0.6849 (3)0.0527 (6)
H140.29120.15270.60130.063*
C150.7272 (2)0.04266 (18)0.7970 (4)0.0888 (9)
H15A0.76090.08970.86890.133*
H15B0.77450.02260.72950.133*
H15C0.71570.00070.87500.133*
C160.0288 (2)0.56282 (15)0.6910 (4)0.0780 (8)
H16A0.09980.56700.60220.117*
H16B0.02550.58900.64540.117*
H16C0.03090.59020.80060.117*
H20.2197 (19)0.2603 (13)0.737 (2)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0431 (10)0.0511 (12)0.0482 (11)0.0074 (9)0.0208 (9)0.0010 (9)
N20.0464 (10)0.0510 (12)0.0481 (12)0.0108 (9)0.0236 (9)0.0054 (9)
O10.0741 (11)0.0536 (11)0.0878 (13)0.0155 (9)0.0333 (10)0.0116 (9)
O20.0637 (10)0.0662 (10)0.0492 (9)0.0145 (8)0.0284 (8)0.0100 (8)
O30.0635 (11)0.1180 (15)0.0804 (13)0.0380 (10)0.0401 (11)0.0142 (11)
C10.0489 (13)0.0565 (15)0.0416 (13)0.0076 (11)0.0162 (11)0.0018 (11)
C20.0526 (14)0.0630 (16)0.0447 (14)0.0127 (13)0.0154 (11)0.0016 (11)
C30.0665 (17)0.085 (2)0.0557 (16)0.0325 (15)0.0195 (14)0.0003 (13)
C40.0543 (16)0.121 (3)0.0627 (18)0.0267 (17)0.0252 (14)0.0017 (17)
C50.0587 (16)0.106 (2)0.080 (2)0.0090 (16)0.0360 (15)0.0130 (17)
C60.0578 (15)0.0715 (17)0.0648 (17)0.0077 (13)0.0266 (13)0.0044 (13)
C70.0484 (13)0.0530 (14)0.0458 (13)0.0035 (11)0.0202 (11)0.0012 (11)
C80.0450 (13)0.0454 (13)0.0493 (14)0.0025 (11)0.0182 (11)0.0011 (11)
C90.0451 (13)0.0513 (14)0.0454 (13)0.0055 (10)0.0162 (11)0.0009 (10)
C100.0563 (15)0.106 (2)0.0462 (15)0.0222 (15)0.0168 (13)0.0041 (14)
C110.0512 (15)0.120 (2)0.0616 (18)0.0299 (15)0.0180 (13)0.0122 (16)
C120.0540 (15)0.0704 (17)0.0627 (17)0.0178 (12)0.0292 (14)0.0071 (13)
C130.0608 (15)0.0799 (18)0.0499 (15)0.0157 (13)0.0235 (13)0.0013 (12)
C140.0433 (13)0.0639 (15)0.0520 (15)0.0104 (11)0.0157 (11)0.0005 (12)
C150.0634 (18)0.112 (2)0.102 (2)0.0400 (16)0.0407 (17)0.0286 (18)
C160.094 (2)0.0503 (17)0.085 (2)0.0136 (14)0.0189 (17)0.0054 (14)
Geometric parameters (Å, º) top
N1—C71.273 (2)C6—H60.9300
N1—N21.383 (2)C7—H70.9300
N2—C81.351 (3)C8—C91.481 (3)
N2—H20.898 (9)C9—C101.375 (3)
O1—C21.365 (3)C9—C141.387 (3)
O1—C161.424 (3)C10—C111.378 (3)
O2—C81.234 (2)C10—H100.9300
O3—C121.364 (2)C11—C121.369 (3)
O3—C151.424 (3)C11—H110.9300
C1—C61.377 (3)C12—C131.377 (3)
C1—C21.397 (3)C13—C141.372 (3)
C1—C71.460 (3)C13—H130.9300
C2—C31.379 (3)C14—H140.9300
C3—C41.378 (3)C15—H15A0.9600
C3—H30.9300C15—H15B0.9600
C4—C51.366 (4)C15—H15C0.9600
C4—H40.9300C16—H16A0.9600
C5—C61.384 (3)C16—H16B0.9600
C5—H50.9300C16—H16C0.9600
C7—N1—N2114.46 (17)C10—C9—C14117.94 (19)
C8—N2—N1118.77 (17)C10—C9—C8119.13 (19)
C8—N2—H2123.7 (15)C14—C9—C8122.9 (2)
N1—N2—H2115.9 (15)C9—C10—C11121.5 (2)
C2—O1—C16118.51 (18)C9—C10—H10119.2
C12—O3—C15117.7 (2)C11—C10—H10119.2
C6—C1—C2118.4 (2)C12—C11—C10119.8 (2)
C6—C1—C7121.9 (2)C12—C11—H11120.1
C2—C1—C7119.7 (2)C10—C11—H11120.1
O1—C2—C3124.4 (2)O3—C12—C11124.4 (2)
O1—C2—C1115.38 (19)O3—C12—C13115.9 (2)
C3—C2—C1120.2 (2)C11—C12—C13119.7 (2)
C4—C3—C2119.6 (3)C14—C13—C12120.2 (2)
C4—C3—H3120.2C14—C13—H13119.9
C2—C3—H3120.2C12—C13—H13119.9
C5—C4—C3121.3 (2)C13—C14—C9120.9 (2)
C5—C4—H4119.4C13—C14—H14119.6
C3—C4—H4119.4C9—C14—H14119.6
C4—C5—C6118.7 (3)O3—C15—H15A109.5
C4—C5—H5120.6O3—C15—H15B109.5
C6—C5—H5120.6H15A—C15—H15B109.5
C1—C6—C5121.7 (2)O3—C15—H15C109.5
C1—C6—H6119.2H15A—C15—H15C109.5
C5—C6—H6119.2H15B—C15—H15C109.5
N1—C7—C1120.65 (19)O1—C16—H16A109.5
N1—C7—H7119.7O1—C16—H16B109.5
C1—C7—H7119.7H16A—C16—H16B109.5
O2—C8—N2122.35 (19)O1—C16—H16C109.5
O2—C8—C9122.1 (2)H16A—C16—H16C109.5
N2—C8—C9115.56 (19)H16B—C16—H16C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.90 (1)1.99 (1)2.859 (2)164 (2)
Symmetry code: (i) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC16H16N2O3
Mr284.31
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)12.705 (1), 16.053 (2), 7.718 (1)
β (°) 107.233 (2)
V3)1503.5 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.983, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
8570, 3007, 1574
Rint0.050
(sin θ/λ)max1)0.622
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.123, 0.98
No. of reflections3007
No. of parameters195
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.13, 0.19

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.898 (9)1.985 (11)2.859 (2)164 (2)
Symmetry code: (i) x, y+1/2, z1/2.
 

References

First citationAlhadi, A. A., Ali, H. M., Puvaneswary, S., Robinson, W. T. & Ng, S. W. (2008). Acta Cryst. E64, o1584.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKüçükgüzel, S. G., Mazi, A., Sahin, F., Öztürk, S. & Stables, J. (2003). Eur. J. Med. Chem. 38, 1005–1013.  Web of Science PubMed Google Scholar
First citationMohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009a). Acta Cryst. E65, o189.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationMohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009b). Acta Cryst. E65, o190.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLi, M.-L., Huang, X. & Feng, R.-K. (2009). Acta Cryst. E65, o369.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhang, M.-J., Yin, L.-Z., Wang, D.-C., Deng, X.-M. & Liu, J.-B. (2009). Acta Cryst. E65, o508.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds