(E)-4-Nitro-N′-(3-nitro­benzyl­idene)benzohydrazide

Li, X.-Y.

doi:10.1107/S1600536812004540

organic compounds

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Volume 68| Part 3| March 2012| Page o655

doi:10.1107/S1600536812004540

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(E)-4-Nitro-N′-(3-nitrobenzylidene)benzohydrazide

Xiao-Yan Li ^a ^*

^aZibo Vocational Institute, Zibo 255314, People's Republic of China
^*Correspondence e-mail: lixiaoyan_zb@126.com

(Received 2 February 2012; accepted 2 February 2012; online 10 February 2012)

The title compound, C₁₄H₁₀N₄O₅, has an E conformation with respect to the C=N bond. The dihedral angle between the benzene rings is 2.41 (14)°. In the crystal, molecules are linked through N—H⋯O hydrogen bonds to form chains along the c axis. C—H⋯O interactions are also present, linking the chains to form a three-dimensional network.

Related literature

For the syntheses and crystal structures of hydrazone compounds, see: Hashemian et al. (2011 ); Lei (2011 ); Shalash et al. (2010 ). For the crystal structures of similar compounds, reported on by the author, see: Li (2011a ,b , 2012 ).

Experimental

Crystal data

C₁₄H₁₀N₄O₅
M_r = 314.26
Monoclinic, P 2₁ /c
a = 11.856 (2) Å
b = 14.116 (3) Å
c = 8.6263 (19) Å
β = 95.193 (2)°
V = 1437.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.17 × 0.13 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.981, T_max = 0.987
10319 measured reflections
2671 independent reflections
1288 reflections with I > 2σ(I)
R_int = 0.104

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.123
S = 0.84
2671 reflections
211 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3ⁱ	0.91 (2)	1.99 (2)	2.853 (3)	158 (2)
C6—H6⋯O1ⁱⁱ	0.93	2.57	3.369 (4)	145
C7—H7⋯O5ⁱⁱⁱ	0.93	2.56	3.287 (4)	135
C7—H7⋯O3ⁱ	0.93	2.53	3.271 (3)	137
C14—H14⋯O4ⁱⁱⁱ	0.93	2.40	3.246 (4)	151
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812004540/su2375sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812004540/su2375Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812004540/su2375Isup3.cml

checkCIF report

Comment top

In recent years, hydrazone compounds have attracted much attention due to their syntheses and crystal structures (Hashemian et al., 2011; Lei, 2011; Shalash et al., 2010). As a continuation of our work on such compounds (Li, 2011a,b; Li, 2012), the author reports herein on the crystal structure of the new title hydrazone compound.

The title compound (Fig. 1) exists in an E conformation with respect to the C7═N1 bond. The dihedral angle between the (C1–C6) and (C9–C14) benzene rings is 2.41 (14) °.

In the crystal, molecules are linked through N–H···O hydrogen bonds to form chains along the c axis (Fig. 2 and Table 1). There are also C-H···O interactions present that link the chains to form a three-dimensional network (Table 1).

Related literature top

For the syntheses and crystal structures of hydrazone compounds, see: Hashemian et al. (2011); Lei (2011); Shalash et al. (2010). For the crystal structures of similar compounds, reported recently by the author, see: Li (2011a,b, 2012).

Experimental top

A mixture of 3-nitrobenzaldehyde (0.151 g, 1 mmol) and 4-nitrobenzohydrazide (0.181 g, 1 mmol) in 30 ml of ethanol containing few drops of acetic acid was refluxed for about 1 h. On cooling to room temperature, a solid precipitate was formed. The solid was filtered and then recrystallized from methanol. Yellow crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of a solution of the title compound in methanol.

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

	Fig. 1. The molecular structure of the title compound, showing the atom labelling scheme. The displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view along the b axis of the crystal packing of the title compound. The N-H···O hydrogen bonds are indicated by dashed lines (see Table 1 for details). The C-bound H-atoms have been omitted for clarity.

(E)-4-Nitro-N'-(3-nitrobenzylidene)benzohydrazide top

Crystal data top

C₁₄H₁₀N₄O₅	F(000) = 648
M_r = 314.26	D_x = 1.452 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 979 reflections
a = 11.856 (2) Å	θ = 2.3–26.3°
b = 14.116 (3) Å	µ = 0.11 mm⁻¹
c = 8.6263 (19) Å	T = 298 K
β = 95.193 (2)°	Block, yellow
V = 1437.8 (5) Å³	0.17 × 0.13 × 0.12 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2671 independent reflections
Radiation source: fine-focus sealed tube	1288 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.104
ω scans	θ_max = 25.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.981, T_max = 0.987	k = −17→16
10319 measured reflections	l = −10→10

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 0.84	w = 1/[σ²(F_o²) + (0.0424P)²] where P = (F_o² + 2F_c²)/3
2671 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.18 e Å⁻³
1 restraint	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₄H₁₀N₄O₅	V = 1437.8 (5) Å³
M_r = 314.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.856 (2) Å	µ = 0.11 mm⁻¹
b = 14.116 (3) Å	T = 298 K
c = 8.6263 (19) Å	0.17 × 0.13 × 0.12 mm
β = 95.193 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2671 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1288 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.987	R_int = 0.104
10319 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	1 restraint
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 0.84	Δρ_max = 0.18 e Å⁻³
2671 reflections	Δρ_min = −0.16 e Å⁻³
211 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	U_iso*/U_eq
O1	0.1287 (3)	1.33204 (17)	0.1686 (3)	0.1354 (15)
O2	0.2448 (3)	1.26884 (18)	0.0245 (4)	0.1188 (15)
O3	0.23263 (15)	0.65945 (12)	0.1876 (2)	0.0537 (7)
O4	0.4769 (3)	0.3590 (2)	−0.3204 (4)	0.1556 (18)
O5	0.5842 (3)	0.4737 (2)	−0.3733 (3)	0.1211 (14)
N1	0.17622 (18)	0.83659 (16)	0.0848 (2)	0.0491 (8)
N2	0.22711 (19)	0.76953 (16)	−0.0036 (2)	0.0483 (9)
N3	0.1702 (3)	1.2632 (2)	0.1105 (4)	0.0899 (16)
N4	0.5047 (3)	0.4393 (3)	−0.3104 (4)	0.0936 (16)
C1	0.1348 (2)	1.00191 (19)	0.1080 (3)	0.0425 (10)
C2	0.1696 (2)	1.0919 (2)	0.0706 (3)	0.0522 (11)
C3	0.1282 (3)	1.1686 (2)	0.1461 (4)	0.0581 (12)
C4	0.0505 (3)	1.1592 (2)	0.2540 (4)	0.0726 (14)
C5	0.0174 (3)	1.0690 (2)	0.2908 (4)	0.0689 (12)
C6	0.0592 (2)	0.9917 (2)	0.2202 (3)	0.0544 (11)
C7	0.1814 (2)	0.9203 (2)	0.0303 (3)	0.0486 (10)
C8	0.2553 (2)	0.68447 (18)	0.0579 (3)	0.0405 (10)
C9	0.3200 (2)	0.62217 (18)	−0.0417 (3)	0.0387 (9)
C10	0.3076 (2)	0.52468 (18)	−0.0295 (3)	0.0478 (10)
C11	0.3684 (3)	0.4655 (2)	−0.1197 (4)	0.0605 (11)
C12	0.4412 (3)	0.5048 (2)	−0.2157 (3)	0.0608 (11)
C13	0.4570 (2)	0.5997 (2)	−0.2249 (3)	0.0623 (12)
C14	0.3961 (2)	0.6581 (2)	−0.1383 (3)	0.0524 (11)
H2	0.22020	1.10040	−0.00440	0.0630*
H2A	0.245 (2)	0.7813 (19)	−0.1021 (16)	0.0800*
H4	0.02120	1.21200	0.30070	0.0870*
H5	−0.03420	1.06070	0.36470	0.0820*
H6	0.03660	0.93130	0.24770	0.0650*
H7	0.21570	0.92980	−0.06130	0.0580*
H10	0.25910	0.49930	0.03850	0.0570*
H11	0.35970	0.40020	−0.11490	0.0720*
H13	0.50850	0.62460	−0.28920	0.0750*
H14	0.40610	0.72330	−0.14440	0.0630*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.204 (3)	0.0522 (16)	0.154 (3)	0.0280 (19)	0.039 (2)	−0.0131 (18)
O2	0.128 (3)	0.0639 (18)	0.169 (3)	−0.0092 (17)	0.039 (2)	0.0148 (18)
O3	0.0739 (14)	0.0488 (12)	0.0407 (11)	−0.0012 (10)	0.0178 (10)	0.0052 (10)
O4	0.157 (3)	0.110 (2)	0.196 (4)	0.058 (2)	−0.004 (2)	−0.077 (3)
O5	0.108 (2)	0.174 (3)	0.083 (2)	0.079 (2)	0.0178 (17)	−0.0014 (19)
N1	0.0579 (15)	0.0459 (15)	0.0454 (14)	0.0112 (12)	0.0145 (12)	−0.0004 (12)
N2	0.0655 (17)	0.0451 (14)	0.0371 (14)	0.0116 (12)	0.0198 (12)	0.0010 (12)
N3	0.116 (3)	0.051 (2)	0.101 (3)	0.012 (2)	0.000 (2)	0.0029 (19)
N4	0.080 (3)	0.125 (3)	0.072 (2)	0.054 (3)	−0.0140 (19)	−0.019 (2)
C1	0.0389 (16)	0.0469 (18)	0.0411 (16)	0.0061 (14)	0.0011 (13)	−0.0036 (14)
C2	0.0483 (19)	0.0519 (19)	0.0563 (19)	0.0063 (15)	0.0035 (15)	0.0006 (15)
C3	0.067 (2)	0.045 (2)	0.061 (2)	0.0126 (17)	−0.0010 (17)	−0.0018 (16)
C4	0.082 (3)	0.062 (2)	0.073 (2)	0.022 (2)	0.002 (2)	−0.0110 (19)
C5	0.061 (2)	0.079 (2)	0.068 (2)	0.022 (2)	0.0138 (17)	−0.005 (2)
C6	0.0494 (18)	0.058 (2)	0.0562 (19)	0.0044 (15)	0.0064 (15)	−0.0017 (16)
C7	0.0488 (18)	0.0550 (19)	0.0426 (17)	0.0011 (15)	0.0078 (14)	−0.0057 (15)
C8	0.0452 (17)	0.0394 (17)	0.0374 (16)	−0.0084 (13)	0.0061 (13)	0.0025 (13)
C9	0.0395 (16)	0.0402 (16)	0.0365 (15)	0.0007 (13)	0.0038 (13)	0.0013 (13)
C10	0.0509 (18)	0.0423 (17)	0.0494 (18)	−0.0025 (15)	0.0000 (14)	0.0004 (14)
C11	0.066 (2)	0.0439 (18)	0.067 (2)	0.0093 (17)	−0.0183 (18)	−0.0127 (17)
C12	0.059 (2)	0.074 (2)	0.0479 (19)	0.0325 (19)	−0.0027 (16)	−0.0147 (18)
C13	0.059 (2)	0.076 (2)	0.054 (2)	0.0204 (18)	0.0167 (17)	0.0064 (18)
C14	0.0540 (19)	0.0489 (18)	0.0566 (19)	0.0053 (15)	0.0176 (15)	0.0063 (15)

Geometric parameters (Å, º) top

O1—N3	1.218 (4)	C5—C6	1.365 (4)
O2—N3	1.207 (5)	C8—C9	1.490 (4)
O3—C8	1.226 (3)	C9—C14	1.379 (4)
O4—N4	1.181 (5)	C9—C10	1.389 (4)
O5—N4	1.229 (5)	C10—C11	1.387 (4)
N1—N2	1.387 (3)	C11—C12	1.367 (5)
N1—C7	1.275 (4)	C12—C13	1.356 (4)
N2—C8	1.343 (3)	C13—C14	1.363 (4)
N3—C3	1.467 (4)	C2—H2	0.9300
N4—C12	1.483 (5)	C4—H4	0.9300
N2—H2A	0.910 (16)	C5—H5	0.9300
C1—C6	1.385 (4)	C6—H6	0.9300
C1—C7	1.466 (4)	C7—H7	0.9300
C1—C2	1.383 (4)	C10—H10	0.9300
C2—C3	1.377 (4)	C11—H11	0.9300
C3—C4	1.374 (5)	C13—H13	0.9300
C4—C5	1.378 (4)	C14—H14	0.9300

N2—N1—C7	113.1 (2)	C8—C9—C14	122.0 (2)
N1—N2—C8	119.87 (19)	C9—C10—C11	119.4 (2)
O1—N3—O2	123.1 (3)	C10—C11—C12	119.0 (3)
O1—N3—C3	118.9 (3)	N4—C12—C13	120.3 (3)
O2—N3—C3	118.0 (3)	N4—C12—C11	117.4 (3)
O4—N4—O5	124.5 (4)	C11—C12—C13	122.3 (3)
O4—N4—C12	119.1 (3)	C12—C13—C14	118.9 (3)
O5—N4—C12	116.4 (4)	C9—C14—C13	121.1 (3)
C8—N2—H2A	117.5 (17)	C1—C2—H2	120.00
N1—N2—H2A	122.6 (17)	C3—C2—H2	121.00
C2—C1—C7	118.9 (2)	C3—C4—H4	121.00
C2—C1—C6	119.0 (2)	C5—C4—H4	121.00
C6—C1—C7	122.2 (2)	C4—C5—H5	120.00
C1—C2—C3	119.0 (2)	C6—C5—H5	120.00
N3—C3—C4	119.4 (3)	C1—C6—H6	120.00
N3—C3—C2	118.3 (3)	C5—C6—H6	120.00
C2—C3—C4	122.3 (3)	N1—C7—H7	119.00
C3—C4—C5	117.9 (3)	C1—C7—H7	119.00
C4—C5—C6	120.9 (3)	C9—C10—H10	120.00
C1—C6—C5	120.9 (3)	C11—C10—H10	120.00
N1—C7—C1	121.8 (2)	C10—C11—H11	120.00
O3—C8—C9	121.5 (2)	C12—C11—H11	121.00
N2—C8—C9	115.0 (2)	C12—C13—H13	121.00
O3—C8—N2	123.4 (2)	C14—C13—H13	120.00
C10—C9—C14	119.3 (2)	C9—C14—H14	119.00
C8—C9—C10	118.5 (2)	C13—C14—H14	119.00

C7—N1—N2—C8	162.4 (2)	C1—C2—C3—C4	−2.2 (5)
N2—N1—C7—C1	−178.7 (2)	N3—C3—C4—C5	−176.6 (3)
N1—N2—C8—O3	4.4 (4)	C2—C3—C4—C5	2.6 (5)
N1—N2—C8—C9	−173.9 (2)	C3—C4—C5—C6	−1.1 (5)
O1—N3—C3—C2	175.1 (3)	C4—C5—C6—C1	−0.9 (5)
O1—N3—C3—C4	−5.6 (5)	O3—C8—C9—C10	31.6 (4)
O2—N3—C3—C2	−4.9 (5)	O3—C8—C9—C14	−144.7 (3)
O2—N3—C3—C4	174.3 (4)	N2—C8—C9—C10	−150.0 (2)
O4—N4—C12—C11	12.8 (5)	N2—C8—C9—C14	33.7 (3)
O4—N4—C12—C13	−167.8 (3)	C8—C9—C10—C11	−179.1 (3)
O5—N4—C12—C11	−166.9 (3)	C14—C9—C10—C11	−2.7 (4)
O5—N4—C12—C13	12.5 (5)	C8—C9—C14—C13	178.0 (2)
C6—C1—C2—C3	0.1 (4)	C10—C9—C14—C13	1.8 (4)
C7—C1—C2—C3	−178.4 (3)	C9—C10—C11—C12	1.6 (4)
C2—C1—C6—C5	1.4 (4)	C10—C11—C12—N4	−180.0 (3)
C7—C1—C6—C5	179.9 (3)	C10—C11—C12—C13	0.7 (5)
C2—C1—C7—N1	162.1 (2)	N4—C12—C13—C14	179.0 (3)
C6—C1—C7—N1	−16.4 (4)	C11—C12—C13—C14	−1.7 (4)
C1—C2—C3—N3	177.1 (3)	C12—C13—C14—C9	0.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3ⁱ	0.91 (2)	1.99 (2)	2.853 (3)	158 (2)
C6—H6···O1ⁱⁱ	0.93	2.57	3.369 (4)	145
C7—H7···O5ⁱⁱⁱ	0.93	2.56	3.287 (4)	135
C7—H7···O3ⁱ	0.93	2.53	3.271 (3)	137
C14—H14···O4ⁱⁱⁱ	0.93	2.40	3.246 (4)	151

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀N₄O₅
M_r	314.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.856 (2), 14.116 (3), 8.6263 (19)
β (°)	95.193 (2)
V (Å³)	1437.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.17 × 0.13 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	10319, 2671, 1288
R_int	0.104
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.123, 0.84
No. of reflections	2671
No. of parameters	211
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.16

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···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3ⁱ	0.910 (16)	1.991 (17)	2.853 (3)	158 (2)
C6—H6···O1ⁱⁱ	0.93	2.57	3.369 (4)	145
C7—H7···O5ⁱⁱⁱ	0.93	2.56	3.287 (4)	135
C7—H7···O3ⁱ	0.93	2.53	3.271 (3)	137
C14—H14···O4ⁱⁱⁱ	0.93	2.40	3.246 (4)	151

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

Acknowledgements

The author is grateful to the Zibo Vocational Institute for supporting this work.

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