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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3439
https://doi.org/10.1107/S1600536811049944

N′-(2-Hy­dr­oxy­benzyl­­idene)-3-methyl­benzohydrazide

Zeng-Xin Liua*

aExperimental Center, Linyi University, Linyi 276005, People's Republic of China
*Correspondence e-mail: zengxin_liu@163.com

(Received 21 November 2011; accepted 22 November 2011; online 25 November 2011)

The title compound, C15H14N2O2, is the product of the reaction of 2-hy­droxy­benzaldehyde and 3-methyl­benzo­hydrazide. The dihedral angle between the substituted benzene rings is 19.5 (3)° and an intra­molecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds to generate C(4) chains propagating in [001] and C—H⋯O inter­actions to the same O-atom acceptor reinforce the chains.

Related literature

For reference bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orphen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For related structues, see: Horkaew et al. (2011[Horkaew, J., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o2985.]); Fun et al. (2011[Fun, H.-K., Horkaew, J. & Chantrapromma, S. (2011). Acta Cryst. E67, o2644-o2645.]); Su et al. (2011[Su, F., Gu, Z.-G. & Lin, J. (2011). Acta Cryst. E67, o1634.]); Hashemian et al. (2011[Hashemian, S., Ghaeinee, V. & Notash, B. (2011). Acta Cryst. E67, o171.]); Promdet et al. (2011[Promdet, P., Horkaew, J., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o3224.]).

[Scheme 1]

Experimental

Crystal data

  • C15H14N2O2

  • Mr = 254.28

  • Monoclinic, P 21 /c

  • a = 11.042 (2) Å

  • b = 13.588 (3) Å

  • c = 8.7936 (15) Å

  • β = 94.406 (2)°

  • V = 1315.5 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 K

  • 0.17 × 0.17 × 0.15 mm
Data collection

  • Bruker SMART 1K CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.985, Tmax = 0.987

  • 9633 measured reflections

  • 2686 independent reflections

  • 1528 reflections with I > 2σ(I)

  • Rint = 0.052
Refinement

  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 0.186

  • S = 1.04

  • 2686 reflections

  • 177 parameters

  • 1 restraint

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

  • Δρmax = 0.59 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯N1 0.82 1.91 2.624 (2) 146
N2—H2⋯O2i 0.90 (1) 1.91 (1) 2.793 (3) 168 (3)
C7—H7⋯O2i 0.93 2.49 3.229 (2) 137
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. 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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811049944/hb6528sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049944/hb6528Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811049944/hb6528Isup3.cml

checkCIF report


Comment top

Recently, the compounds derived from the condensation reaction of carbonyl-containing compounds with substituted benzohydrazides have received considerable attention. In this paper, the title new compound, derived from the reaction of 2-hydroxybenzaldehyde with 3-methylbenzohydrazide, is reported.

The molecule of the compound, Fig. 1, displays a trans-configuration about the C7 ═N1 bond. The torsion angle of C7—N1—N2—C8 is 7.0 (3)°. The dihedral angle between the C1—C6 and C9—C14 benzene rings is 19.5 (3)°, indicating the molecule of the compound is twisted. Overall, the bond distances are within normal values (Allen et al., 1987), and are comparable with those reported in similar compounds (Horkaew et al., 2011; Fun et al., 2011; Su et al., 2011; Hashemian et al., 2011; Promdet et al., 2011). In the crystal, molecules are linked by N—H···O intermolecular hydrogen bonds (Table 1) to form one-dimensional chains along the c axis (Fig. 2).

Related literature top

For reference bond lengths, see: Allen et al. (1987). For related structues, see: Horkaew et al. (2011); Fun et al. (2011); Su et al. (2011); Hashemian et al. (2011); Promdet et al. (2011).

Experimental top

The title compound was synthesized by the reaction of 2-hydroxybenzaldehyde (1 mmol, 0.12 g) with 4-methylbenzohydrazide (1 mmol, 0.15 g) in absolute methanol (30 ml) at ambient condition. Colorless prism-shaped single crystals were obtained by slow evaporation of the solution at room temperature after several days.

Refinement top

The amide H atom was located in a difference map and was refined isotropically, with N—H = 0.90 (1) Å. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 Å for aromatic and CH and 0.96 Å for CH3 atoms, and with O—H = 0.82 Å. The Uiso(H) values were constrained to be 1.5Ueq of C15 and O1 atoms, and 1.2Ueq for the remaining C atoms. A rotating group model was used for the methyl group.

Structure description top

Recently, the compounds derived from the condensation reaction of carbonyl-containing compounds with substituted benzohydrazides have received considerable attention. In this paper, the title new compound, derived from the reaction of 2-hydroxybenzaldehyde with 3-methylbenzohydrazide, is reported.

The molecule of the compound, Fig. 1, displays a trans-configuration about the C7 ═N1 bond. The torsion angle of C7—N1—N2—C8 is 7.0 (3)°. The dihedral angle between the C1—C6 and C9—C14 benzene rings is 19.5 (3)°, indicating the molecule of the compound is twisted. Overall, the bond distances are within normal values (Allen et al., 1987), and are comparable with those reported in similar compounds (Horkaew et al., 2011; Fun et al., 2011; Su et al., 2011; Hashemian et al., 2011; Promdet et al., 2011). In the crystal, molecules are linked by N—H···O intermolecular hydrogen bonds (Table 1) to form one-dimensional chains along the c axis (Fig. 2).

For reference bond lengths, see: Allen et al. (1987). For related structues, see: Horkaew et al. (2011); Fun et al. (2011); Su et al. (2011); Hashemian et al. (2011); Promdet et al. (2011).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, showing 30% probability displacement ellipsoids. The intramolecular O—H···N hydrogen bond is shown as a dashed line.
[Figure 2] Fig. 2. The molecular packing of the title compound, showing the N—H···O, O—H···N, and C—H···O hydrogen-bonds (dashed lines).
N'-(2-Hydroxybenzylidene)-3-methylbenzohydrazide top
Crystal data top
C15H14N2O2F(000) = 536
Mr = 254.28Dx = 1.284 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.042 (2) ÅCell parameters from 1290 reflections
b = 13.588 (3) Åθ = 2.4–24.5°
c = 8.7936 (15) ŵ = 0.09 mm−1
β = 94.406 (2)°T = 298 K
V = 1315.5 (4) Å3Prism, colorless
Z = 40.17 × 0.17 × 0.15 mm
Data collection top
Bruker SMART 1K CCD
diffractometer		2686 independent reflections
Radiation source: fine-focus sealed tube1528 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
ω scanθmax = 26.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→13
Tmin = 0.985, Tmax = 0.987k = −17→15
9633 measured reflectionsl = −10→10
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0872P)2 + 0.1389P]
where P = (Fo2 + 2Fc2)/3
2686 reflections(Δ/σ)max < 0.001
177 parametersΔρmax = 0.59 e Å−3
1 restraintΔρmin = −0.24 e Å−3
Crystal data top
C15H14N2O2V = 1315.5 (4) Å3
Mr = 254.28Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.042 (2) ŵ = 0.09 mm−1
b = 13.588 (3) ÅT = 298 K
c = 8.7936 (15) Å0.17 × 0.17 × 0.15 mm
β = 94.406 (2)°
Data collection top
Bruker SMART 1K CCD
diffractometer		2686 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1528 reflections with I > 2σ(I)
Tmin = 0.985, Tmax = 0.987Rint = 0.052
9633 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0621 restraint
wR(F2) = 0.186H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.59 e Å−3
2686 reflectionsΔρmin = −0.24 e Å−3
177 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
N10.28488 (18)0.65695 (15)0.0597 (2)0.0486 (5)
N20.22818 (19)0.72924 (16)−0.0306 (2)0.0521 (6)
O10.42021 (18)0.59365 (14)0.2981 (2)0.0661 (6)
H10.37870.63350.24730.099*
O20.22190 (17)0.83426 (13)0.16687 (18)0.0610 (6)
C10.3578 (2)0.49285 (18)0.0816 (3)0.0463 (6)
C20.4170 (2)0.50626 (19)0.2260 (3)0.0488 (6)
C30.4770 (2)0.4277 (2)0.2997 (3)0.0645 (8)
H30.51760.43670.39530.077*
C40.4765 (3)0.3370 (2)0.2314 (4)0.0701 (9)
H40.51630.28460.28180.084*
C50.4180 (3)0.3224 (2)0.0897 (4)0.0696 (8)
H50.41760.26050.04450.083*
C60.3600 (2)0.39998 (19)0.0152 (3)0.0601 (7)
H60.32140.3903−0.08140.072*
C70.2970 (2)0.57306 (19)−0.0011 (3)0.0508 (6)
H70.26600.5630−0.10130.061*
C80.2014 (2)0.81577 (18)0.0313 (3)0.0457 (6)
C90.1440 (2)0.89021 (19)−0.0753 (3)0.0471 (6)
C100.1681 (2)0.98853 (19)−0.0468 (3)0.0549 (7)
H100.21941.00560.03790.066*
C110.1186 (2)1.0620 (2)−0.1397 (3)0.0634 (8)
C120.0402 (3)1.0358 (3)−0.2601 (3)0.0768 (10)
H120.00481.0844−0.32330.092*
C130.0125 (3)0.9383 (3)−0.2897 (3)0.0796 (10)
H13−0.04180.9219−0.37190.095*
C140.0652 (2)0.8645 (2)−0.1976 (3)0.0617 (8)
H140.04760.7987−0.21830.074*
C150.1510 (3)1.1678 (2)−0.1097 (5)0.1026 (13)
H15A0.17791.1969−0.20060.154*
H15B0.21481.1717−0.02940.154*
H15C0.08091.2025−0.07980.154*
H20.226 (3)0.718 (2)−0.1311 (13)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0553 (12)0.0510 (13)0.0390 (12)0.0021 (10)0.0003 (9)0.0082 (10)
N20.0706 (14)0.0517 (13)0.0332 (11)0.0040 (11)−0.0023 (10)0.0029 (10)
O10.0816 (14)0.0590 (13)0.0556 (12)0.0063 (10)−0.0080 (10)−0.0021 (10)
O20.0881 (13)0.0607 (12)0.0324 (10)0.0018 (9)−0.0064 (9)−0.0003 (8)
C10.0501 (14)0.0469 (15)0.0427 (15)−0.0014 (11)0.0093 (11)0.0031 (11)
C20.0543 (14)0.0473 (16)0.0455 (15)0.0020 (12)0.0085 (11)0.0005 (12)
C30.0666 (18)0.069 (2)0.0576 (18)0.0114 (15)0.0015 (13)0.0035 (15)
C40.0721 (19)0.0573 (19)0.082 (2)0.0160 (15)0.0138 (17)0.0101 (17)
C50.0748 (19)0.0540 (18)0.082 (2)0.0016 (15)0.0173 (17)−0.0099 (16)
C60.0688 (18)0.0511 (17)0.0603 (18)−0.0028 (13)0.0039 (14)−0.0046 (14)
C70.0592 (15)0.0535 (17)0.0396 (14)−0.0043 (12)0.0029 (11)−0.0007 (13)
C80.0514 (14)0.0506 (16)0.0345 (14)−0.0042 (11)−0.0006 (11)0.0025 (12)
C90.0482 (14)0.0589 (17)0.0344 (13)0.0035 (11)0.0038 (10)0.0039 (12)
C100.0514 (14)0.0579 (17)0.0555 (17)0.0001 (12)0.0045 (12)0.0047 (14)
C110.0569 (16)0.0629 (19)0.072 (2)0.0131 (14)0.0162 (15)0.0207 (15)
C120.081 (2)0.090 (3)0.060 (2)0.0348 (19)0.0108 (16)0.0262 (18)
C130.075 (2)0.111 (3)0.0500 (18)0.031 (2)−0.0128 (14)−0.0029 (18)
C140.0644 (17)0.075 (2)0.0441 (16)0.0152 (14)−0.0061 (13)−0.0042 (14)
C150.083 (2)0.064 (2)0.161 (4)0.0066 (18)0.016 (2)0.038 (2)
Geometric parameters (Å, º) top
N1—C71.270 (3)C6—H60.9300
N1—N21.382 (3)C7—H70.9300
N2—C81.338 (3)C8—C91.487 (3)
N2—H20.895 (10)C9—C141.375 (3)
O1—C21.345 (3)C9—C101.381 (4)
O1—H10.8200C10—C111.376 (4)
O2—C81.223 (3)C10—H100.9300
C1—C61.392 (3)C11—C121.362 (4)
C1—C21.395 (3)C11—C151.500 (4)
C1—C71.447 (3)C12—C131.380 (4)
C2—C31.390 (4)C12—H120.9300
C3—C41.371 (4)C13—C141.389 (4)
C3—H30.9300C13—H130.9300
C4—C51.374 (4)C14—H140.9300
C4—H40.9300C15—H15A0.9600
C5—C61.373 (4)C15—H15B0.9600
C5—H50.9300C15—H15C0.9600
C7—N1—N2117.0 (2)O2—C8—C9120.8 (2)
C8—N2—N1119.7 (2)N2—C8—C9116.0 (2)
C8—N2—H2124.0 (19)C14—C9—C10119.3 (2)
N1—N2—H2115.1 (19)C14—C9—C8122.2 (2)
C2—O1—H1109.5C10—C9—C8118.5 (2)
C6—C1—C2118.6 (2)C11—C10—C9122.1 (3)
C6—C1—C7119.6 (2)C11—C10—H10118.9
C2—C1—C7121.8 (2)C9—C10—H10118.9
O1—C2—C3117.6 (2)C12—C11—C10118.1 (3)
O1—C2—C1122.5 (2)C12—C11—C15121.0 (3)
C3—C2—C1119.8 (2)C10—C11—C15120.9 (3)
C4—C3—C2120.0 (3)C11—C12—C13121.1 (3)
C4—C3—H3120.0C11—C12—H12119.5
C2—C3—H3120.0C13—C12—H12119.5
C3—C4—C5120.9 (3)C12—C13—C14120.4 (3)
C3—C4—H4119.6C12—C13—H13119.8
C5—C4—H4119.6C14—C13—H13119.8
C6—C5—C4119.4 (3)C9—C14—C13118.9 (3)
C6—C5—H5120.3C9—C14—H14120.5
C4—C5—H5120.3C13—C14—H14120.5
C5—C6—C1121.3 (3)C11—C15—H15A109.5
C5—C6—H6119.4C11—C15—H15B109.5
C1—C6—H6119.4H15A—C15—H15B109.5
N1—C7—C1121.6 (2)C11—C15—H15C109.5
N1—C7—H7119.2H15A—C15—H15C109.5
C1—C7—H7119.2H15B—C15—H15C109.5
O2—C8—N2123.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.912.624 (2)146
N2—H2···O2i0.90 (1)1.91 (1)2.793 (3)168 (3)
C7—H7···O2i0.932.493.229 (2)137
Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC15H14N2O2
Mr254.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)11.042 (2), 13.588 (3), 8.7936 (15)
β (°) 94.406 (2)
V (Å3)1315.5 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.17 × 0.17 × 0.15
Data collection
DiffractometerBruker SMART 1K CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.985, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections		9633, 2686, 1528
Rint0.052
(sin θ/λ)max (Å−1)0.627
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.186, 1.04
No. of reflections2686
No. of parameters177
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.59, −0.24

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.912.624 (2)146
N2—H2···O2i0.90 (1)1.912 (12)2.793 (3)168 (3)
C7—H7···O2i0.932.493.229 (2)137
Symmetry code: (i) x, −y+3/2, z−1/2.
 

Acknowledgements

The author thanks the Experimental Center of Linyi University for support.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orphen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
 First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFun, H.-K., Horkaew, J. & Chantrapromma, S. (2011). Acta Cryst. E67, o2644–o2645.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationHashemian, S., Ghaeinee, V. & Notash, B. (2011). Acta Cryst. E67, o171.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationHorkaew, J., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o2985.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationPromdet, P., Horkaew, J., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o3224.  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 citationSu, F., Gu, Z.-G. & Lin, J. (2011). Acta Cryst. E67, o1634.  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
Volume 67| Part 12| December 2011| Page o3439
https://doi.org/10.1107/S1600536811049944
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