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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1383.
Published online 2008 July 5. doi:  10.1107/S1600536808019636
PMCID: PMC2962016

N′-(2-Chloro-5-nitro­benzyl­idene)-3-hydroxy­benzohydrazide methanol solvate

Abstract

In the title compound, C14H10ClN3O4·CH3OH, the dihedral angle between the two benzene rings is 33.9 (2)°. In the crystal structure, the methanol solvent mol­ecules are linked to the Schiff base mol­ecules through inter­molecular N—H(...)O and O—H(...)O hydrogen bonds. Mol­ecules are further linked through inter­molecular O—H(...)O and O—H(...)N hydrogen bonds, forming chains running along the b axis.

Related literature

For related structures, see: Zhou & Tang (2007 [triangle]); Zhou & Xiao (2007 [triangle]). For related literature, see: Ali et al. (2007 [triangle]); Butcher et al. (2007 [triangle]); He (2008 [triangle]); Jing & Yu (2007 [triangle]); Nie (2008 [triangle]).

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Object name is e-64-o1383-scheme1.jpg

Experimental

Crystal data

  • C14H10ClN3O4·CH4O
  • M r = 351.74
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1383-efi1.jpg
  • a = 7.716 (3) Å
  • b = 11.945 (2) Å
  • c = 17.650 (3) Å
  • β = 99.886 (2)°
  • V = 1602.6 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 298 (2) K
  • 0.27 × 0.23 × 0.22 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.931, T max = 0.943
  • 12656 measured reflections
  • 3316 independent reflections
  • 2396 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.121
  • S = 1.01
  • 3316 reflections
  • 223 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019636/rz2226sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019636/rz2226Isup2.hkl

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

Acknowledgments

The author thanks Kaili College for financial support.

supplementary crystallographic information

Comment

Recently, we have reported two metal complexes with Schiff base ligands (Zhou & Tang, 2007; Zhou & Xiao, 2007). We report herein the crystal structure of the title Schiff base compound (Fig. 1).

The title compound consists of a Schiff base molecule and a methanol molecule of crystallization. The dihedral angle between the two benzene rings is 33.9 (2)°. All bond lengths are comparable to those found in similar compounds (Ali et al., 2007; Nie, 2008; He, 2008; Butcher et al., 2007; Jing & Yu, 2007). In the crystal structure, the methanol molecules are linked to the Schiff base molecules through intermolecular N–H···O and O–H···O hydrogen bonds (Table 1). Molecules are further linked through intermolecular O—H···O and O—H···N hydrogen bonds to form chains running along the b axis (Fig. 2).

Experimental

2-Chloro-5-nitrobenzaldehyde (1.0 mmol, 167.1 mg) and 3-hydroxybenzohydrazide (1.0 mmol, 152.1 mg) were dissolved in methanol (30 ml). The mixture was stirred at reflux for 30 min to give a colourless solution. After keeping the solution in air for a few days, colourless block-shaped crystals were formed.

Refinement

H3B was located in a difference Fourier map and refined isotropically, with Uiso(H) fixed at 0.08 Å2. Other H atoms were positioned geometrically and refined using a riding model with O–H = 0.92 Å, C–H = 0.93-0.96 Å, and with Uiso(H) = 1.2 or 1.5Ueq(C, O).

Figures

Fig. 1.
The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. Hydrogen bond is shown as a dashed line.
Fig. 2.
The crystal packing of the title copound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C14H10ClN3O4·CH4OF000 = 728
Mr = 351.74Dx = 1.458 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2947 reflections
a = 7.716 (3) Åθ = 2.3–24.5º
b = 11.945 (2) ŵ = 0.27 mm1
c = 17.650 (3) ÅT = 298 (2) K
β = 99.886 (2)ºBlock, colourless
V = 1602.6 (7) Å30.27 × 0.23 × 0.22 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer3316 independent reflections
Radiation source: fine-focus sealed tube2396 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.034
T = 298(2) Kθmax = 26.5º
ω scansθmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −9→9
Tmin = 0.931, Tmax = 0.943k = −14→14
12656 measured reflectionsl = −21→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121  w = 1/[σ2(Fo2) + (0.0596P)2 + 0.2859P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
3316 reflectionsΔρmax = 0.18 e Å3
223 parametersΔρmin = −0.22 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
Cl10.27705 (9)0.68944 (5)0.42450 (4)0.0774 (2)
O1−0.1188 (3)1.16001 (18)0.30340 (10)0.0978 (7)
O20.0033 (3)1.21390 (16)0.41618 (12)0.0859 (6)
O30.4707 (2)1.09327 (11)0.70885 (8)0.0623 (4)
O40.6995 (2)0.71117 (11)0.91382 (8)0.0607 (4)
H40.64790.66900.88080.091*
O50.6192 (3)0.69826 (13)0.66034 (11)0.0897 (6)
H50.59070.66450.69680.135*
N1−0.0240 (3)1.14400 (19)0.36561 (12)0.0652 (5)
N20.3857 (2)0.95587 (12)0.58923 (8)0.0428 (4)
N30.4964 (2)0.92397 (13)0.65533 (9)0.0424 (4)
C10.2405 (2)0.90699 (16)0.46380 (10)0.0439 (5)
C20.1934 (3)0.82357 (18)0.40857 (12)0.0534 (5)
C30.0788 (3)0.8448 (2)0.34054 (13)0.0684 (7)
H30.05020.78800.30450.082*
C40.0082 (3)0.9485 (2)0.32639 (12)0.0663 (7)
H4A−0.06900.96330.28100.080*
C50.0531 (3)1.03136 (19)0.38052 (11)0.0533 (5)
C60.1661 (3)1.01296 (17)0.44857 (10)0.0468 (5)
H60.19271.07050.48410.056*
C70.3601 (3)0.88397 (16)0.53602 (11)0.0460 (5)
H70.41790.81540.54280.055*
C80.5280 (2)0.99647 (15)0.71415 (10)0.0429 (4)
C90.6354 (2)0.95567 (15)0.78653 (10)0.0409 (4)
C100.6158 (2)0.84831 (15)0.81342 (10)0.0414 (4)
H100.53660.79920.78490.050*
C110.7141 (3)0.81385 (16)0.88285 (11)0.0451 (5)
C120.8325 (3)0.88781 (18)0.92424 (11)0.0536 (5)
H120.90030.86520.97040.064*
C130.8499 (3)0.99430 (19)0.89738 (12)0.0591 (6)
H130.92951.04320.92590.071*
C140.7518 (3)1.03021 (17)0.82898 (11)0.0511 (5)
H140.76331.10290.81160.061*
C150.6536 (4)0.6218 (2)0.60542 (17)0.0899 (9)
H15A0.67690.66130.56090.135*
H15B0.55350.57390.59110.135*
H15C0.75420.57750.62630.135*
H3B0.538 (3)0.862 (2)0.6593 (14)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0721 (4)0.0661 (4)0.0918 (5)0.0006 (3)0.0077 (3)−0.0362 (3)
O10.1037 (15)0.1191 (16)0.0612 (11)0.0065 (12)−0.0124 (10)0.0357 (11)
O20.0977 (14)0.0643 (11)0.0857 (13)0.0020 (10)−0.0123 (11)0.0069 (10)
O30.0989 (12)0.0348 (8)0.0464 (8)0.0086 (7)−0.0068 (8)−0.0028 (6)
O40.0881 (12)0.0414 (8)0.0441 (8)−0.0011 (7)−0.0130 (7)0.0061 (6)
O50.1570 (19)0.0489 (10)0.0750 (12)0.0195 (10)0.0527 (12)0.0041 (8)
N10.0607 (12)0.0783 (14)0.0543 (12)−0.0043 (10)0.0038 (10)0.0231 (11)
N20.0519 (10)0.0387 (8)0.0355 (8)−0.0009 (7)0.0013 (7)−0.0009 (7)
N30.0523 (10)0.0363 (8)0.0357 (8)0.0010 (7)−0.0005 (7)−0.0004 (7)
C10.0437 (11)0.0531 (12)0.0356 (10)−0.0079 (8)0.0087 (8)−0.0059 (8)
C20.0507 (12)0.0624 (13)0.0489 (12)−0.0078 (10)0.0132 (10)−0.0157 (10)
C30.0644 (15)0.0928 (19)0.0463 (13)−0.0128 (14)0.0050 (11)−0.0305 (13)
C40.0610 (14)0.097 (2)0.0378 (11)−0.0051 (13)0.0000 (10)−0.0035 (12)
C50.0506 (12)0.0699 (14)0.0396 (11)−0.0102 (10)0.0080 (9)0.0053 (10)
C60.0508 (11)0.0549 (12)0.0343 (10)−0.0117 (9)0.0061 (8)−0.0001 (8)
C70.0541 (12)0.0415 (10)0.0413 (10)−0.0005 (9)0.0054 (9)−0.0035 (8)
C80.0526 (11)0.0343 (10)0.0403 (10)−0.0041 (8)0.0041 (9)−0.0002 (8)
C90.0476 (11)0.0382 (10)0.0359 (9)−0.0012 (8)0.0041 (8)−0.0030 (7)
C100.0477 (11)0.0377 (10)0.0359 (10)−0.0013 (8)−0.0012 (8)−0.0065 (8)
C110.0540 (12)0.0415 (11)0.0376 (10)0.0039 (8)0.0020 (9)−0.0016 (8)
C120.0553 (13)0.0621 (13)0.0379 (10)−0.0032 (10)−0.0075 (9)−0.0019 (9)
C130.0626 (14)0.0634 (14)0.0462 (12)−0.0232 (11)−0.0049 (10)−0.0094 (10)
C140.0627 (13)0.0434 (11)0.0449 (11)−0.0141 (9)0.0026 (10)−0.0020 (9)
C150.109 (2)0.0755 (18)0.095 (2)0.0083 (16)0.0456 (18)−0.0195 (16)

Geometric parameters (Å, °)

Cl1—C21.732 (2)C4—C51.378 (3)
O1—N11.225 (2)C4—H4A0.9300
O2—N11.214 (3)C5—C61.375 (3)
O3—C81.236 (2)C6—H60.9300
O4—C111.355 (2)C7—H70.9300
O4—H40.8200C8—C91.481 (2)
O5—C151.390 (3)C9—C101.385 (3)
O5—H50.8200C9—C141.389 (3)
N1—C51.477 (3)C10—C111.388 (3)
N2—C71.263 (2)C10—H100.9300
N2—N31.376 (2)C11—C121.385 (3)
N3—C81.342 (2)C12—C131.372 (3)
N3—H3B0.81 (3)C12—H120.9300
C1—C61.397 (3)C13—C141.379 (3)
C1—C21.398 (3)C13—H130.9300
C1—C71.466 (3)C14—H140.9300
C2—C31.387 (3)C15—H15A0.9600
C3—C41.358 (4)C15—H15B0.9600
C3—H30.9300C15—H15C0.9600
C11—O4—H4109.5C1—C7—H7119.5
C15—O5—H5109.5O3—C8—N3122.02 (17)
O2—N1—O1123.6 (2)O3—C8—C9120.89 (16)
O2—N1—C5118.83 (18)N3—C8—C9117.09 (16)
O1—N1—C5117.5 (2)C10—C9—C14120.50 (17)
C7—N2—N3115.93 (16)C10—C9—C8121.50 (16)
C8—N3—N2118.75 (15)C14—C9—C8117.94 (17)
C8—N3—H3B120.6 (18)C9—C10—C11120.11 (17)
N2—N3—H3B120.6 (18)C9—C10—H10119.9
C6—C1—C2117.57 (18)C11—C10—H10119.9
C6—C1—C7120.92 (17)O4—C11—C12117.23 (17)
C2—C1—C7121.49 (18)O4—C11—C10123.60 (17)
C3—C2—C1121.6 (2)C12—C11—C10119.16 (18)
C3—C2—Cl1118.32 (17)C13—C12—C11120.26 (18)
C1—C2—Cl1120.09 (16)C13—C12—H12119.9
C4—C3—C2120.1 (2)C11—C12—H12119.9
C4—C3—H3119.9C12—C13—C14121.29 (18)
C2—C3—H3119.9C12—C13—H13119.4
C3—C4—C5118.8 (2)C14—C13—H13119.4
C3—C4—H4A120.6C13—C14—C9118.66 (19)
C5—C4—H4A120.6C13—C14—H14120.7
C6—C5—C4122.5 (2)C9—C14—H14120.7
C6—C5—N1118.48 (19)O5—C15—H15A109.5
C4—C5—N1119.0 (2)O5—C15—H15B109.5
C5—C6—C1119.39 (19)H15A—C15—H15B109.5
C5—C6—H6120.3O5—C15—H15C109.5
C1—C6—H6120.3H15A—C15—H15C109.5
N2—C7—C1120.94 (18)H15B—C15—H15C109.5
N2—C7—H7119.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H4···O3i0.821.912.7237 (19)169
O4—H4···N2i0.822.623.118 (2)120
O5—H5···O3i0.822.002.817 (2)175
N3—H3B···O50.81 (3)2.05 (3)2.854 (2)173 (3)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2226).

References

  • Ali, H. M., Zuraini, K., Wan Jefrey, B. & Ng, S. W. (2007). Acta Cryst. E63, o1729–o1730.
  • Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Butcher, R. J., Jasinski, J. P., Narayana, B., Sunil, K. & Yathirajan, H. S. (2007). Acta Cryst. E63, o3652.
  • He, L. (2008). Acta Cryst. E64, o82. [PMC free article] [PubMed]
  • Jing, Z.-L. & Yu, M. (2007). Acta Cryst. E63, o509–o510.
  • Nie, Y. (2008). Acta Cryst. E64, o471. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhou, Z. & Tang, R.-R. (2007). Acta Cryst. E63, m2960.
  • Zhou, Z. & Xiao, Z.-H. (2007). Acta Cryst. E63, m2012.

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