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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 66| Part 8| August 2010| Page o2026
https://doi.org/10.1107/S1600536810026723

N′-[(E)-2-Chloro-5-nitro­benzyl­­idene]-2-nitro­benzohydrazide

Huanyu Liua*

aSchool of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Zhongshan 528453, People's Republic of China
*Correspondence e-mail: liuhuanyu03@163.com

(Received 5 July 2010; accepted 6 July 2010; online 14 July 2010)

In the title compound, C14H9ClN4O5, the mol­ecule exists in a trans geometry with respect to the methyl­idene unit. The dihedral angle between the two substituted benzene rings is 62.7 (2)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R22(8) loops.

Related literature

For a related structure and background references, see: Liu (2010[Liu, H. (2010). Acta Cryst. E66, o1582.]).

[Scheme 1]

Experimental

Crystal data

  • C14H9ClN4O5

  • Mr = 348.70

  • Triclinic, [P \overline 1]

  • a = 7.432 (3) Å

  • b = 9.296 (4) Å

  • c = 12.404 (5) Å

  • α = 77.621 (5)°

  • β = 87.674 (6)°

  • γ = 76.271 (5)°

  • V = 813.1 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 298 K

  • 0.20 × 0.18 × 0.17 mm
Data collection

  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.949, Tmax = 0.956

  • 4610 measured reflections

  • 2863 independent reflections

  • 1878 reflections with I > 2σ(I)

  • Rint = 0.018
Refinement

  • R[F2 > 2σ(F2)] = 0.069

  • wR(F2) = 0.207

  • S = 1.00

  • 2863 reflections

  • 220 parameters

  • 1 restraint

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

  • Δρmax = 1.26 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯O3i 0.90 (1) 2.05 (1) 2.937 (3) 170 (4)
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810026723/hb5545sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810026723/hb5545Isup2.hkl

checkCIF report


Comment top

Recently, the author has reported a hydrazone compound (Liu, 2010). As a further study on these compounds, in the present work, a new hydrazone compound is reported.

In the title compound (Fig. 1), the hydrazone molecule exists in a trans geometry with respect to the methylidene unit. The dihedral angle between the two substituted benzene rings is 62.7 (2)°. The O1/N3/O2 nitro plane forms a dihedral angle of 3.7 (2)° with the C1-C6 benzene ring. The O4/N4/O5 nitro plane forms a dihedral angle of 33.9 (2)° with the C9-C14 benzene ring. In the crystal structure, adjacent two molecules are linked through two N—H···O hydrogen bonds (Table 1) to form a dimer (Fig. 2).

Related literature top

For a related structure and background references, see: Liu (2010).

Experimental top

2-Chloro-5-nitrobenzaldehyde (1.0 mmol, 185 mg) and 2-nitrobenzohydrazide (1.0 mmol, 181 mg) were mixed in 50 mL methanol. The mixture was stirred at ambient temperature for 2 h and filtered. Colorless blocks of (I) were formed by slow evaporation of the filtrate for 5 d.

Refinement top

The amino hydrogen atom was located in an electronic density map and refined isotropically, with the N—H distance restrained to 0.90 (1)Å. Other hydrogen atoms were placed in calculated positions, with C—H = 0.93 Å, and refined as riding with Uiso(H) = 1.2Ueq(C). The structure contains solvent accessible VOIDS of 70 Å3, which might accord a disordered water molecule.

Structure description top

Recently, the author has reported a hydrazone compound (Liu, 2010). As a further study on these compounds, in the present work, a new hydrazone compound is reported.

In the title compound (Fig. 1), the hydrazone molecule exists in a trans geometry with respect to the methylidene unit. The dihedral angle between the two substituted benzene rings is 62.7 (2)°. The O1/N3/O2 nitro plane forms a dihedral angle of 3.7 (2)° with the C1-C6 benzene ring. The O4/N4/O5 nitro plane forms a dihedral angle of 33.9 (2)° with the C9-C14 benzene ring. In the crystal structure, adjacent two molecules are linked through two N—H···O hydrogen bonds (Table 1) to form a dimer (Fig. 2).

For a related structure and background references, see: Liu (2010).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) with 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing structure of (I), viewed along the a axis. Hydrogen bonds are shown as dashed lines.
N'-[(E)-2-Chloro-5-nitrobenzylidene]-2-nitrobenzohydrazide top
Crystal data top
C14H9ClN4O5Z = 2
Mr = 348.70F(000) = 356
Triclinic, P1Dx = 1.424 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.432 (3) ÅCell parameters from 1380 reflections
b = 9.296 (4) Åθ = 2.3–25.3°
c = 12.404 (5) ŵ = 0.27 mm−1
α = 77.621 (5)°T = 298 K
β = 87.674 (6)°Block, colorless
γ = 76.271 (5)°0.20 × 0.18 × 0.17 mm
V = 813.1 (6) Å3
Data collection top
Bruker SMART CCD
diffractometer		2863 independent reflections
Radiation source: fine-focus sealed tube1878 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ω scansθmax = 25.5°, θmin = 3.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −8→8
Tmin = 0.949, Tmax = 0.956k = −11→11
4610 measured reflectionsl = −14→15
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)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.207H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.1395P)2]
where P = (Fo2 + 2Fc2)/3
2863 reflections(Δ/σ)max < 0.001
220 parametersΔρmax = 1.26 e Å−3
1 restraintΔρmin = −0.30 e Å−3
Crystal data top
C14H9ClN4O5γ = 76.271 (5)°
Mr = 348.70V = 813.1 (6) Å3
Triclinic, P1Z = 2
a = 7.432 (3) ÅMo Kα radiation
b = 9.296 (4) ŵ = 0.27 mm−1
c = 12.404 (5) ÅT = 298 K
α = 77.621 (5)°0.20 × 0.18 × 0.17 mm
β = 87.674 (6)°
Data collection top
Bruker SMART CCD
diffractometer		2863 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1878 reflections with I > 2σ(I)
Tmin = 0.949, Tmax = 0.956Rint = 0.018
4610 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0691 restraint
wR(F2) = 0.207H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 1.26 e Å−3
2863 reflectionsΔρmin = −0.30 e Å−3
220 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl10.26862 (17)0.10161 (9)0.90359 (9)0.0893 (4)
N10.0650 (3)0.5612 (3)0.73068 (18)0.0489 (6)
N20.0178 (4)0.5714 (3)0.62253 (19)0.0572 (7)
N30.2718 (5)0.6264 (5)1.1036 (3)0.0751 (9)
N40.1665 (4)0.8525 (3)0.6682 (3)0.0640 (8)
O10.3378 (7)0.5946 (5)1.1976 (3)0.1348 (14)
O20.2136 (6)0.7508 (4)1.0530 (3)0.1165 (13)
O3−0.1109 (4)0.7087 (3)0.46232 (17)0.0702 (7)
O40.2419 (4)0.8013 (3)0.5910 (3)0.0858 (8)
O50.2494 (4)0.8607 (3)0.7502 (3)0.0919 (9)
C10.2110 (4)0.4041 (3)0.8957 (2)0.0463 (7)
C20.2716 (5)0.2577 (3)0.9592 (3)0.0577 (8)
C30.3337 (6)0.2313 (4)1.0669 (3)0.0731 (10)
H30.37500.13271.10680.088*
C40.3341 (5)0.3520 (4)1.1146 (3)0.0669 (9)
H40.37370.33631.18720.080*
C50.2751 (4)0.4952 (4)1.0530 (2)0.0534 (7)
C60.2128 (4)0.5243 (3)0.9448 (2)0.0503 (7)
H60.17260.62350.90560.060*
C70.1508 (4)0.4296 (3)0.7812 (2)0.0516 (7)
H70.17520.34940.74480.062*
C8−0.0717 (4)0.7033 (3)0.5596 (2)0.0513 (7)
C9−0.1414 (4)0.8379 (3)0.6106 (2)0.0466 (7)
C10−0.0355 (4)0.9083 (3)0.6632 (2)0.0515 (7)
C11−0.1089 (5)1.0291 (4)0.7086 (3)0.0655 (9)
H11−0.03301.07130.74420.079*
C12−0.3001 (6)1.0897 (4)0.7013 (3)0.0679 (9)
H12−0.35301.17420.73040.081*
C13−0.4087 (5)1.0227 (4)0.6508 (3)0.0640 (9)
H13−0.53621.06150.64650.077*
C14−0.3317 (4)0.8988 (3)0.6062 (2)0.0539 (7)
H14−0.40820.85500.57260.065*
H20.059 (5)0.490 (3)0.593 (3)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1262 (9)0.0423 (5)0.0944 (8)−0.0049 (5)−0.0208 (6)−0.0162 (4)
N10.0592 (14)0.0462 (13)0.0415 (12)−0.0080 (11)−0.0069 (10)−0.0131 (10)
N20.0807 (18)0.0518 (14)0.0384 (13)−0.0060 (13)−0.0138 (12)−0.0157 (11)
N30.085 (2)0.097 (3)0.0616 (18)−0.0388 (19)0.0027 (15)−0.0368 (18)
N40.0637 (18)0.0618 (17)0.0698 (18)−0.0260 (14)−0.0047 (15)−0.0076 (14)
O10.209 (4)0.147 (3)0.076 (2)−0.064 (3)−0.030 (2)−0.052 (2)
O20.184 (4)0.0693 (19)0.104 (2)−0.020 (2)−0.030 (2)−0.0391 (18)
O30.1005 (17)0.0660 (14)0.0406 (12)−0.0051 (12)−0.0208 (11)−0.0157 (10)
O40.0632 (16)0.102 (2)0.0902 (19)−0.0215 (14)0.0062 (14)−0.0149 (16)
O50.0805 (18)0.100 (2)0.103 (2)−0.0297 (15)−0.0357 (15)−0.0219 (16)
C10.0505 (16)0.0424 (15)0.0448 (15)−0.0063 (12)−0.0044 (12)−0.0107 (12)
C20.0676 (19)0.0459 (16)0.0570 (18)−0.0073 (14)−0.0055 (14)−0.0107 (14)
C30.089 (2)0.060 (2)0.0555 (19)−0.0032 (18)−0.0098 (17)0.0065 (16)
C40.077 (2)0.078 (2)0.0410 (16)−0.0118 (18)−0.0085 (15)−0.0075 (16)
C50.0533 (17)0.069 (2)0.0445 (16)−0.0210 (15)0.0005 (12)−0.0176 (14)
C60.0578 (17)0.0491 (16)0.0453 (15)−0.0152 (13)−0.0042 (13)−0.0092 (12)
C70.0641 (18)0.0454 (16)0.0440 (15)−0.0049 (13)−0.0057 (13)−0.0145 (12)
C80.0601 (17)0.0535 (17)0.0407 (15)−0.0123 (14)−0.0090 (13)−0.0099 (13)
C90.0554 (17)0.0442 (15)0.0399 (14)−0.0148 (13)−0.0071 (12)−0.0032 (11)
C100.0583 (18)0.0464 (16)0.0503 (16)−0.0168 (13)−0.0103 (13)−0.0043 (12)
C110.087 (3)0.0514 (18)0.066 (2)−0.0263 (18)−0.0113 (17)−0.0159 (15)
C120.091 (3)0.0481 (18)0.064 (2)−0.0095 (17)−0.0033 (18)−0.0172 (15)
C130.063 (2)0.064 (2)0.0571 (18)−0.0017 (16)−0.0046 (15)−0.0086 (16)
C140.0613 (19)0.0528 (17)0.0459 (15)−0.0110 (14)−0.0114 (13)−0.0073 (13)
Geometric parameters (Å, º) top
Cl1—C21.740 (3)C3—H30.9300
N1—C71.277 (4)C4—C51.364 (5)
N1—N21.378 (3)C4—H40.9300
N2—C81.341 (4)C5—C61.388 (4)
N2—H20.898 (10)C6—H60.9300
N3—O21.180 (5)C7—H70.9300
N3—O11.232 (5)C8—C91.496 (4)
N3—C51.481 (4)C9—C141.392 (4)
N4—O41.217 (4)C9—C101.394 (4)
N4—O51.235 (4)C10—C111.353 (4)
N4—C101.467 (4)C11—C121.398 (5)
O3—C81.241 (3)C11—H110.9300
C1—C61.384 (4)C12—C131.371 (5)
C1—C21.398 (4)C12—H120.9300
C1—C71.460 (4)C13—C141.376 (5)
C2—C31.383 (5)C13—H130.9300
C3—C41.377 (5)C14—H140.9300
C7—N1—N2115.0 (2)C1—C6—H6120.3
C8—N2—N1121.2 (2)C5—C6—H6120.3
C8—N2—H2120 (3)N1—C7—C1120.4 (2)
N1—N2—H2118 (3)N1—C7—H7119.8
O2—N3—O1124.6 (4)C1—C7—H7119.8
O2—N3—C5120.1 (3)O3—C8—N2119.6 (3)
O1—N3—C5115.3 (4)O3—C8—C9120.4 (3)
O4—N4—O5124.2 (3)N2—C8—C9119.7 (2)
O4—N4—C10117.8 (3)C14—C9—C10116.3 (3)
O5—N4—C10118.0 (3)C14—C9—C8117.0 (3)
C6—C1—C2117.7 (3)C10—C9—C8126.7 (3)
C6—C1—C7121.1 (3)C11—C10—C9123.4 (3)
C2—C1—C7121.2 (2)C11—C10—N4117.4 (3)
C3—C2—C1122.0 (3)C9—C10—N4119.2 (3)
C3—C2—Cl1117.9 (2)C10—C11—C12119.1 (3)
C1—C2—Cl1120.0 (2)C10—C11—H11120.5
C4—C3—C2119.6 (3)C12—C11—H11120.5
C4—C3—H3120.2C13—C12—C11119.0 (3)
C2—C3—H3120.2C13—C12—H12120.5
C5—C4—C3118.6 (3)C11—C12—H12120.5
C5—C4—H4120.7C12—C13—C14121.0 (3)
C3—C4—H4120.7C12—C13—H13119.5
C4—C5—C6122.8 (3)C14—C13—H13119.5
C4—C5—N3119.3 (3)C13—C14—C9121.2 (3)
C6—C5—N3117.9 (3)C13—C14—H14119.4
C1—C6—C5119.3 (3)C9—C14—H14119.4
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.90 (1)2.05 (1)2.937 (3)170 (4)
Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC14H9ClN4O5
Mr348.70
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)7.432 (3), 9.296 (4), 12.404 (5)
α, β, γ (°)77.621 (5), 87.674 (6), 76.271 (5)
V (Å3)813.1 (6)
Z2
Radiation typeMo Kα
µ (mm−1)0.27
Crystal size (mm)0.20 × 0.18 × 0.17
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.949, 0.956
No. of measured, independent and
observed [I > 2σ(I)] reflections		4610, 2863, 1878
Rint0.018
(sin θ/λ)max (Å−1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.069, 0.207, 1.00
No. of reflections2863
No. of parameters220
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)1.26, −0.30

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), 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···O3i0.898 (10)2.049 (13)2.937 (3)170 (4)
Symmetry code: (i) −x, −y+1, −z+1.
 

Acknowledgements

The work was supported by the Guangdong Pharmaceutical University Young Teachers' Fund and the Ten Hundred Thousand Project of the Bureau of Education of Guangdong Province, China.

References

First citationBruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationLiu, H. (2010). Acta Cryst. E66, o1582.  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

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 66| Part 8| August 2010| Page o2026
https://doi.org/10.1107/S1600536810026723
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