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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2578.
Published online 2009 September 30. doi:  10.1107/S1600536809038902
PMCID: PMC2970267

(E)-2-(Isonicotinoylhydrazonometh­yl)benzoic acid methanol monosolvate

Abstract

The title compound, C14H11N3O3·CH4O, was synthesized by the condensation reaction of isonicotinohydrazide with an equimolar quantity of 2-formyl­benzoic acid in methanol. The hydrazone mol­ecule displays an E configuration about the C=N bond. The dihedral angel between the pyridine and the benzene rings is 12.04 (5)°. In the crystal structure, mol­ecules are linked by O—H(...)N, O—H(...)O and N—H(...)O hydrogen-bonding inter­actions.

Related literature

For general background to hydrazones, see: Dhande et al. (2007 [triangle]). For a related structure, see: Zhang et al. (2009 [triangle]).

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Object name is e-65-o2578-scheme1.jpg

Experimental

Crystal data

  • C14H11N3O3·CH4O
  • M r = 301.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2578-efi1.jpg
  • a = 6.9768 (11) Å
  • b = 12.2103 (13) Å
  • c = 17.2650 (19) Å
  • β = 95.497 (1)°
  • V = 1464.0 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 K
  • 0.43 × 0.19 × 0.15 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.958, T max = 0.985
  • 7290 measured reflections
  • 2508 independent reflections
  • 1233 reflections with I > 2σ(I)
  • R int = 0.076

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.141
  • S = 0.99
  • 2508 reflections
  • 199 parameters
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038902/bq2160sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038902/bq2160Isup2.hkl

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

Acknowledgments

We acknowledge the financial support of the Natural Science Foundation of China (No. 20771053) and the Natural Science Foundation of Shandong Province (Y2008B48). This work was also supported by the ‘Shangdong Tai-Shan Scholar Research Fund’.

supplementary crystallographic information

Comment

Hydrazones have been attracted significant attention because of their physiological activity, coordinative capability, and applications in analytical chemistry (Dhande et al. 2007). Recently, a large number of hydrazone compounds have been reported (Zhang et al. 2009). As a contribution to the chemistry of hydrazone, we report here the synthesis and crystal structure of the title compound (I).

The crystal structure of (I) is built up of hydrazone and methanol molecules (Fig.1). The dihedral angel between the pyridine and the benzene rings is 12.04 (5) °. The hydrazone molecule crystallizes in E conformation. In the crystal structure, three kinds of intermolecular O—H···N, O—H···O and N—H···O hydrogen bonding interactions are observed and the crystal packing is stabilized by these intermolecular interactions. (Table 1. and Fig. 2).

Experimental

Isonicotinohydrazide (10 mmol) was dissolved in ethanol (40 ml), then 2-formylbenzoic acid (10 mmol) was added into the solution. The reaction mixture was heated under reflux for 2 h. After the solution had cooled to room white sediment appeared. The product was crystallized from methanol. Anal. Calcd (%) for [(C14H11N3O3).(C1H4O1)] (Mr = 301.30): C, 59.79; H, 5.02; N, 13.95; O, 21.24 Found (%): C, 59.83; H, 5.00; N, 13.92; O, 21.25

Refinement

The imino H atom was located in a difference Fourier map and refined isotropically, with the N—H distance restrained to 0.86 Å. Other H atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H = 0.93 (aromatic and methylene) and 0.96(methyl), O—H = 0.82, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(C15 and O).

Figures

Fig. 1.
The molecular structure (I) with 50% probability displacement ellipsoids. O—H···O hydrogen bond is shown in dashed line.
Fig. 2.
The molecular packing of the title compound. Hydrogen bonding is shown in dashed lines.

Crystal data

C14H11N3O3·CH4OF(000) = 632
Mr = 301.30Dx = 1.367 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1170 reflections
a = 6.9768 (11) Åθ = 2.4–21.5°
b = 12.2103 (13) ŵ = 0.10 mm1
c = 17.2650 (19) ÅT = 298 K
β = 95.497 (1)°Block, yellow
V = 1464.0 (3) Å30.43 × 0.19 × 0.15 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer2508 independent reflections
Radiation source: fine-focus sealed tube1233 reflections with I > 2σ(I)
graphiteRint = 0.076
[var phi] and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −8→8
Tmin = 0.958, Tmax = 0.985k = −12→14
7290 measured reflectionsl = −19→20

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.0559P)2] where P = (Fo2 + 2Fc2)/3
2508 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = −0.19 e Å3

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

xyzUiso*/Ueq
N10.2762 (4)0.52906 (18)0.52873 (12)0.0371 (7)
H10.30760.58540.55700.045*
N20.2993 (4)0.42528 (18)0.55868 (14)0.0390 (7)
N30.1111 (4)0.8638 (2)0.36585 (14)0.0438 (7)
O10.1643 (3)0.46359 (16)0.41058 (12)0.0537 (7)
O20.5588 (3)0.46550 (16)0.77984 (11)0.0523 (7)
H20.57520.51250.81370.078*
O30.4040 (4)0.38081 (18)0.86917 (13)0.0654 (8)
O40.4701 (4)0.3132 (2)0.38940 (15)0.0876 (10)
H40.36970.34670.37750.131*
C10.2034 (5)0.5407 (2)0.45415 (17)0.0361 (8)
C20.1221 (5)0.8462 (3)0.44169 (18)0.0474 (9)
H2A0.11030.90570.47450.057*
C30.1501 (5)0.7440 (2)0.47459 (17)0.0406 (9)
H30.15510.73470.52820.049*
C40.1704 (4)0.6558 (2)0.42630 (15)0.0312 (7)
C50.1561 (5)0.6736 (2)0.34726 (16)0.0380 (8)
H50.16600.61550.31310.046*
C60.1271 (5)0.7785 (3)0.31942 (18)0.0429 (9)
H60.11830.79000.26590.052*
C70.3532 (4)0.4180 (2)0.63048 (16)0.0347 (8)
H70.37680.48090.66020.042*
C80.3783 (4)0.3093 (2)0.66650 (17)0.0322 (8)
C90.4202 (5)0.2943 (2)0.74724 (17)0.0353 (8)
C100.4338 (5)0.1888 (2)0.77718 (19)0.0456 (9)
H100.45720.17860.83060.055*
C110.4133 (5)0.0993 (3)0.7289 (2)0.0548 (10)
H110.42550.02900.74960.066*
C120.3750 (5)0.1135 (3)0.6503 (2)0.0551 (10)
H120.36240.05300.61750.066*
C130.3551 (5)0.2177 (2)0.61980 (18)0.0434 (9)
H130.32540.22640.56650.052*
C140.4585 (5)0.3846 (3)0.80510 (18)0.0416 (9)
C150.4316 (6)0.2034 (3)0.3937 (2)0.0742 (13)
H15A0.42640.18280.44710.111*
H15B0.53140.16260.37200.111*
H15C0.31010.18790.36480.111*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0488 (19)0.0284 (14)0.0325 (15)0.0004 (13)−0.0045 (13)0.0009 (11)
N20.0479 (19)0.0308 (14)0.0365 (15)−0.0022 (13)−0.0049 (13)0.0049 (12)
N30.046 (2)0.0452 (16)0.0389 (16)0.0059 (14)−0.0003 (13)0.0045 (13)
O10.076 (2)0.0369 (12)0.0436 (13)0.0013 (12)−0.0172 (12)−0.0072 (11)
O20.078 (2)0.0419 (13)0.0375 (13)−0.0119 (13)0.0066 (12)−0.0091 (10)
O30.099 (2)0.0622 (16)0.0371 (14)0.0029 (15)0.0188 (14)0.0043 (12)
O40.091 (3)0.0691 (19)0.096 (2)−0.0088 (17)−0.0259 (17)−0.0136 (15)
C10.041 (2)0.0362 (18)0.0302 (17)0.0006 (16)−0.0025 (15)−0.0011 (14)
C20.063 (3)0.045 (2)0.0339 (19)0.0114 (18)0.0027 (16)−0.0026 (15)
C30.055 (3)0.0425 (19)0.0232 (17)0.0076 (17)0.0002 (16)0.0029 (14)
C40.030 (2)0.0366 (17)0.0266 (16)0.0033 (14)0.0013 (13)−0.0005 (13)
C50.041 (2)0.0438 (19)0.0284 (17)0.0048 (16)0.0018 (15)−0.0019 (14)
C60.046 (2)0.054 (2)0.0286 (18)0.0026 (18)−0.0005 (16)0.0094 (16)
C70.041 (2)0.0315 (17)0.0309 (17)−0.0005 (15)−0.0007 (14)0.0031 (13)
C80.028 (2)0.0290 (17)0.0388 (18)−0.0009 (14)0.0007 (14)0.0024 (14)
C90.034 (2)0.0332 (17)0.0374 (18)0.0021 (15)−0.0006 (15)0.0079 (14)
C100.051 (2)0.041 (2)0.044 (2)0.0005 (17)0.0033 (17)0.0115 (16)
C110.061 (3)0.0333 (19)0.069 (3)−0.0039 (18)0.001 (2)0.0131 (18)
C120.067 (3)0.032 (2)0.066 (2)−0.0038 (18)0.001 (2)−0.0039 (18)
C130.048 (3)0.0372 (19)0.0430 (19)−0.0029 (17)−0.0059 (17)−0.0002 (15)
C140.050 (2)0.0410 (19)0.0329 (18)0.0089 (18)0.0001 (16)0.0054 (15)
C150.085 (4)0.058 (3)0.077 (3)−0.005 (2)−0.004 (2)−0.007 (2)

Geometric parameters (Å, °)

N1—C11.346 (3)C5—C61.376 (4)
N1—N21.372 (3)C5—H50.9300
N1—H10.8600C6—H60.9300
N2—C71.264 (3)C7—C81.469 (4)
N3—C21.322 (4)C7—H70.9300
N3—C61.325 (4)C8—C131.380 (4)
O1—C11.219 (3)C8—C91.409 (4)
O2—C141.309 (4)C9—C101.388 (4)
O2—H20.8200C9—C141.495 (4)
O3—C141.205 (3)C10—C111.374 (4)
O4—C151.371 (4)C10—H100.9300
O4—H40.8200C11—C121.369 (4)
C1—O11.219 (3)C11—H110.9300
C1—C41.496 (4)C12—C131.378 (4)
C2—C31.377 (4)C12—H120.9300
C2—H2A0.9300C13—H130.9300
C3—C41.377 (4)C15—H15A0.9600
C3—H30.9300C15—H15B0.9600
C4—C51.376 (4)C15—H15C0.9600
C1—N1—N2118.6 (2)C8—C7—H7120.3
C1—N1—H1120.7C13—C8—C9118.3 (3)
N2—N1—H1120.7C13—C8—C7118.9 (3)
C7—N2—N1116.6 (2)C9—C8—C7122.8 (3)
C2—N3—C6118.1 (3)C10—C9—C8119.3 (3)
C14—O2—H2109.5C10—C9—C14115.7 (3)
C15—O4—H4109.5C8—C9—C14124.9 (3)
O1—C1—N1123.4 (3)C11—C10—C9120.9 (3)
O1—C1—N1123.4 (3)C11—C10—H10119.6
O1—C1—C4120.6 (3)C9—C10—H10119.6
O1—C1—C4120.6 (3)C12—C11—C10120.0 (3)
N1—C1—C4116.0 (3)C12—C11—H11120.0
N3—C2—C3123.3 (3)C10—C11—H11120.0
N3—C2—H2A118.4C11—C12—C13119.9 (3)
C3—C2—H2A118.4C11—C12—H12120.0
C2—C3—C4118.5 (3)C13—C12—H12120.0
C2—C3—H3120.7C12—C13—C8121.6 (3)
C4—C3—H3120.7C12—C13—H13119.2
C5—C4—C3118.3 (3)C8—C13—H13119.2
C5—C4—C1117.5 (2)O3—C14—O2124.1 (3)
C3—C4—C1124.2 (2)O3—C14—C9122.2 (3)
C6—C5—C4119.2 (3)O2—C14—C9113.7 (3)
C6—C5—H5120.4O4—C15—H15A109.5
C4—C5—H5120.4O4—C15—H15B109.5
N3—C6—C5122.5 (3)H15A—C15—H15B109.5
N3—C6—H6118.7O4—C15—H15C109.5
C5—C6—H6118.7H15A—C15—H15C109.5
N2—C7—C8119.4 (3)H15B—C15—H15C109.5
N2—C7—H7120.3

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.862.132.891 (3)148
O4—H4···O10.822.142.864 (4)148
O2—H2···N3ii0.821.762.565 (3)165

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, −y+3/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2160).

References

  • Dhande, V. V., Badwaik, V. B. & Aswar, A. S. (2007). Russ. J. Inorg. Chem.52, 1206–1210.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Zhang, Q.-L., Yin, L.-Z., Deng, X.-M., Liu, S.-C. & Song, D.-G. (2009). Acta Cryst. E65, o2392–o2393. [PMC free article] [PubMed]

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