4-{[2-(2,4-Dinitro­phen­yl)hydrazinyl­idene]meth­yl}phenol ethanol hemisolvate

Zhai, X.-R.

doi:10.1107/S1600536810045782

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3142

https://doi.org/10.1107/S1600536810045782

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4-{[2-(2,4-Dinitrophenyl)hydrazinylidene]methyl}phenol ethanol hemisolvate

Xiu-Rong Zhai ^a ^*

^aDepartment of Chemisry and Chemical Engineering, Jining University, 273155 Qufu, Shandong, People's Republic of China
^*Correspondence e-mail: zhaixiurong@163.com

(Received 26 October 2010; accepted 8 November 2010; online 13 November 2010)

In the title compound, C₁₃H₁₀N₄O₅·0.5C₂H₅OH, the two benzene rings form a dihedral angle of 4.29 (9)°. The ethanol solvent molecule was treated as disordered between two orientations related by symmetry (center of inversion), with occupancies fixed at 0.5. The crystal packing, stabilized by intermolecular O—H⋯O and N—H⋯O hydrogen bonds and π–π interactions [indicated by the short distance of 3.7299 (7) Å between the centroids of benzene rings from neighbouring molecules], exhibits short intermolecular O⋯O contacts of 2.8226 (3) Å.

Related literature

For related structures, see: Baughman et al. (2004 ); Shi et al. (2008 ); Ji & Shi (2008 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₃H₁₀N₄O₅·0.5C₂H₆O
M_r = 325.28
Triclinic, $[P \overline 1]$
a = 7.0935 (16) Å
b = 7.2888 (17) Å
c = 14.458 (3) Å
α = 100.156 (4)°
β = 96.378 (4)°
γ = 100.604 (4)°
V = 715.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 295 K
0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.982, T_max = 0.988
4065 measured reflections
2776 independent reflections
1543 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.230
S = 1.04
2776 reflections
227 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.89	1.97	2.605 (3)	127
O6—H6A⋯O3	0.85	1.86	2.702 (9)	174
O5—H5⋯O6ⁱ	0.85	2.26	2.882 (9)	130
O5—H5⋯O4ⁱⁱ	0.85	2.47	3.116 (4)	133
O5—H5⋯O3ⁱⁱ	0.85	2.60	3.404 (4)	159
N1—H1⋯O2ⁱⁱⁱ	0.89	2.63	3.449 (4)	153
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y-1, z-1; (iii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810045782/cv2785sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045782/cv2785Isup2.hkl

checkCIF report

Comment top

As a contribution to structural studies of 2,4-dinitrophenylhydrazones (Baughman et al., 2004; Shi et al., 2008; Ji et al., 2008;) we present here the crystal structure of the title compound (I).

In (I) (Fig. 1), all bond lengths and angles are normal (Allen et al., 1987). The crystal packing, stabilized by intermolecular O—H···O and N—H···O hydrogen bonds (Table 1) and π–π interactions proved by short distance of 3.7299 (7) Å between the centroids of benzene rings from the neighbouring molecules, exhibits short intermolecular O···O contacts of 2.8226 (3) Å.

Related literature top

For related structures, see: Baughman et al. (2004); Shi et al. (2008); Ji et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was synthesized by the reaction of (2,4-dinitro-phenyl)-hydrazine (1 mmol, 198.1 mg) with 4-hydroxy-benzaldehyde (1 mmol, 122.1 mg) in ethanol (20 ml) under reflux conditions (338 K) for 4 h. The solvent was removed and the solid product recrystallized from ethanol. After five days brown crystals were obtained that were suitable for X-ray diffraction study.

Structure description top

For related structures, see: Baughman et al. (2004); Shi et al. (2008); Ji et al. (2008). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound showing the atomic labeling and 30% probability displacement ellipsoids. Solvent molecule omitted for clarity.

4-{[2-(2,4-Dinitrophenyl)hydrazinylidene]methyl}phenol ethanol hemisolvate top

Crystal data top

C₁₃H₁₀N₄O₅·0.5C₂H₆O	Z = 2
M_r = 325.28	F(000) = 338
Triclinic, P1	D_x = 1.510 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0935 (16) Å	Cell parameters from 748 reflections
b = 7.2888 (17) Å	θ = 2.9–24.3°
c = 14.458 (3) Å	µ = 0.12 mm⁻¹
α = 100.156 (4)°	T = 295 K
β = 96.378 (4)°	Block, brown
γ = 100.604 (4)°	0.15 × 0.12 × 0.10 mm
V = 715.2 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2776 independent reflections
Radiation source: fine-focus sealed tube	1543 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
phi and ω scans	θ_max = 26.1°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→8
T_min = 0.982, T_max = 0.988	k = −8→7
4065 measured reflections	l = −14→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.064	H-atom parameters constrained
wR(F²) = 0.230	w = 1/[σ²(F_o²) + (0.1117P)² + 0.1836P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2776 reflections	Δρ_max = 0.46 e Å⁻³
227 parameters	Δρ_min = −0.25 e Å⁻³
3 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (7)

Crystal data top

C₁₃H₁₀N₄O₅·0.5C₂H₆O	γ = 100.604 (4)°
M_r = 325.28	V = 715.2 (3) Å³
Triclinic, P1	Z = 2
a = 7.0935 (16) Å	Mo Kα radiation
b = 7.2888 (17) Å	µ = 0.12 mm⁻¹
c = 14.458 (3) Å	T = 295 K
α = 100.156 (4)°	0.15 × 0.12 × 0.10 mm
β = 96.378 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2776 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1543 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.988	R_int = 0.020
4065 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	3 restraints
wR(F²) = 0.230	H-atom parameters constrained
S = 1.04	Δρ_max = 0.46 e Å⁻³
2776 reflections	Δρ_min = −0.25 e Å⁻³
227 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.6437 (4)	0.7313 (3)	0.73110 (16)	0.0700 (8)
O2	0.4959 (4)	0.5632 (3)	0.59767 (16)	0.0683 (8)
O3	0.7183 (5)	0.4849 (4)	1.00571 (18)	0.0973 (11)
O4	0.5709 (5)	0.2032 (4)	1.00864 (18)	0.1019 (12)
O5	−0.1603 (4)	−0.6843 (4)	0.20416 (18)	0.0890 (10)
H5	−0.1738	−0.6648	0.1478	0.134*
N1	0.3674 (3)	0.1977 (3)	0.57776 (16)	0.0470 (7)
H1	0.3863	0.2907	0.5452	0.070*
N2	0.2771 (3)	0.0174 (4)	0.53066 (17)	0.0479 (7)
N3	0.5558 (4)	0.5794 (4)	0.68230 (18)	0.0499 (7)
N4	0.6183 (5)	0.3288 (5)	0.9659 (2)	0.0698 (9)
C1	0.4286 (4)	0.2316 (4)	0.6718 (2)	0.0412 (7)
C2	0.5213 (4)	0.4143 (4)	0.7248 (2)	0.0420 (7)
C3	0.5848 (4)	0.4436 (4)	0.8208 (2)	0.0474 (8)
H3	0.6479	0.5642	0.8544	0.057*
C4	0.5548 (5)	0.2961 (4)	0.8656 (2)	0.0493 (8)
C5	0.4642 (5)	0.1133 (4)	0.8163 (2)	0.0511 (8)
H5A	0.4453	0.0131	0.8485	0.061*
C6	0.4040 (4)	0.0821 (4)	0.7223 (2)	0.0467 (8)
H6	0.3450	−0.0405	0.6899	0.056*
C7	0.2242 (4)	0.0014 (4)	0.4422 (2)	0.0473 (8)
H7	0.2487	0.1092	0.4157	0.057*
C8	0.1273 (4)	−0.1784 (5)	0.3812 (2)	0.0464 (8)
C9	0.0970 (5)	−0.3493 (5)	0.4128 (2)	0.0551 (9)
H9	0.1418	−0.3512	0.4755	0.066*
C10	0.0018 (5)	−0.5148 (5)	0.3525 (2)	0.0612 (9)
H10	−0.0189	−0.6280	0.3748	0.073*
C11	−0.0638 (5)	−0.5156 (5)	0.2591 (2)	0.0585 (9)
C12	−0.0313 (5)	−0.3488 (5)	0.2267 (2)	0.0617 (10)
H12	−0.0734	−0.3487	0.1635	0.074*
C13	0.0629 (4)	−0.1817 (5)	0.2868 (2)	0.0530 (8)
H13	0.0838	−0.0693	0.2638	0.064*
O6	1.0107 (12)	0.7495 (11)	0.9734 (7)	0.148 (3)	0.50
H6A	0.9238	0.6597	0.9822	0.222*	0.50
C14	0.9498 (18)	0.9229 (13)	0.9968 (12)	0.115 (5)	0.50
H14A	1.0102	0.9845	1.0602	0.138*	0.50
H14B	0.8128	0.8924	0.9983	0.138*	0.50
C15	0.965 (5)	1.042 (3)	0.9313 (12)	0.259 (14)	0.50
H15A	0.9230	1.1573	0.9555	0.388*	0.50
H15B	1.0979	1.0729	0.9223	0.388*	0.50
H15C	0.8861	0.9802	0.8717	0.388*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1033 (19)	0.0395 (14)	0.0569 (14)	−0.0028 (12)	0.0025 (13)	0.0063 (11)
O2	0.0965 (19)	0.0546 (15)	0.0477 (14)	0.0023 (13)	−0.0027 (13)	0.0160 (11)
O3	0.137 (3)	0.078 (2)	0.0503 (15)	−0.0157 (18)	−0.0210 (16)	0.0019 (14)
O4	0.172 (3)	0.075 (2)	0.0533 (17)	0.008 (2)	−0.0009 (18)	0.0265 (15)
O5	0.111 (2)	0.0689 (18)	0.0581 (15)	−0.0248 (16)	−0.0010 (15)	−0.0114 (13)
N1	0.0544 (15)	0.0402 (14)	0.0404 (14)	0.0029 (11)	−0.0003 (11)	0.0045 (11)
N2	0.0490 (15)	0.0455 (15)	0.0426 (15)	0.0056 (11)	0.0013 (12)	−0.0009 (11)
N3	0.0627 (17)	0.0373 (15)	0.0473 (16)	0.0055 (12)	0.0062 (13)	0.0090 (11)
N4	0.102 (2)	0.057 (2)	0.0451 (17)	0.0100 (17)	−0.0015 (16)	0.0098 (15)
C1	0.0406 (15)	0.0407 (17)	0.0406 (16)	0.0074 (12)	0.0052 (12)	0.0049 (12)
C2	0.0451 (16)	0.0360 (16)	0.0441 (16)	0.0083 (12)	0.0062 (13)	0.0060 (12)
C3	0.0569 (19)	0.0370 (17)	0.0432 (17)	0.0064 (13)	0.0034 (14)	0.0003 (12)
C4	0.062 (2)	0.0447 (18)	0.0381 (16)	0.0085 (15)	0.0016 (14)	0.0058 (13)
C5	0.066 (2)	0.0380 (17)	0.0498 (18)	0.0065 (14)	0.0117 (15)	0.0129 (13)
C6	0.0561 (18)	0.0354 (16)	0.0456 (17)	0.0047 (13)	0.0054 (14)	0.0066 (13)
C7	0.0487 (17)	0.0467 (18)	0.0433 (17)	0.0051 (14)	0.0039 (14)	0.0080 (13)
C8	0.0381 (16)	0.056 (2)	0.0401 (16)	0.0039 (13)	0.0047 (13)	0.0020 (14)
C9	0.065 (2)	0.054 (2)	0.0402 (17)	0.0030 (16)	0.0031 (15)	0.0072 (14)
C10	0.071 (2)	0.054 (2)	0.054 (2)	0.0004 (17)	0.0107 (17)	0.0075 (16)
C11	0.055 (2)	0.058 (2)	0.0478 (19)	−0.0092 (16)	0.0056 (15)	−0.0063 (16)
C12	0.056 (2)	0.075 (3)	0.0406 (17)	−0.0040 (17)	−0.0054 (15)	0.0027 (16)
C13	0.0516 (18)	0.058 (2)	0.0431 (17)	0.0020 (15)	−0.0005 (14)	0.0091 (14)
O6	0.139 (7)	0.123 (7)	0.176 (8)	−0.003 (5)	0.043 (6)	0.034 (6)
C14	0.113 (9)	0.044 (5)	0.197 (16)	0.026 (5)	0.058 (10)	0.015 (7)
C15	0.35 (4)	0.24 (3)	0.20 (3)	0.10 (2)	0.06 (3)	0.01 (2)

Geometric parameters (Å, º) top

O1—N3	1.219 (3)	C7—H7	0.9300
O2—N3	1.227 (3)	C8—C13	1.385 (4)
O3—N4	1.229 (4)	C8—C9	1.390 (5)
O4—N4	1.210 (4)	C9—C10	1.368 (4)
O5—C11	1.356 (4)	C9—H9	0.9300
O5—H5	0.8500	C10—C11	1.376 (5)
N1—C1	1.346 (3)	C10—H10	0.9300
N1—N2	1.370 (3)	C11—C12	1.369 (5)
N1—H1	0.8900	C12—C13	1.372 (4)
N2—C7	1.270 (4)	C12—H12	0.9300
N3—O2	1.227 (3)	C13—H13	0.9300
N3—C2	1.439 (4)	O6—C14	1.407 (8)
N4—O3	1.229 (4)	O6—C15ⁱ	1.827 (19)
N4—C4	1.435 (4)	O6—H6A	0.8500
C1—C6	1.410 (4)	C14—C15ⁱ	1.11 (2)
C1—C2	1.413 (4)	C14—C14ⁱ	1.20 (2)
C2—C3	1.377 (4)	C14—C15	1.394 (9)
C3—C4	1.346 (4)	C14—H14A	0.9600
C3—H3	0.9300	C14—H14B	0.9600
C4—C5	1.394 (4)	C15—C14ⁱ	1.11 (2)
C5—C6	1.344 (4)	C15—O6ⁱ	1.828 (19)
C5—H5A	0.9300	C15—H15A	0.9601
C6—H6	0.9300	C15—H15B	0.9600
C7—C8	1.447 (4)	C15—H15C	0.9600

C11—O5—H5	105.5	C9—C10—C11	120.6 (3)
C1—N1—N2	119.9 (3)	C9—C10—H10	119.7
C1—N1—H1	120.9	C11—C10—H10	119.7
N2—N1—H1	119.2	O5—C11—C12	123.4 (3)
C7—N2—N1	114.8 (3)	O5—C11—C10	117.2 (3)
O1—N3—O2	121.8 (3)	C12—C11—C10	119.3 (3)
O1—N3—O2	121.8 (3)	C11—C12—C13	120.5 (3)
O1—N3—C2	119.3 (3)	C11—C12—H12	119.8
O2—N3—C2	119.0 (2)	C13—C12—H12	119.8
O2—N3—C2	119.0 (2)	C12—C13—C8	120.8 (3)
O4—N4—O3	122.2 (3)	C12—C13—H13	119.6
O4—N4—O3	122.2 (3)	C8—C13—H13	119.6
O4—N4—C4	119.2 (3)	C14—O6—H6A	108.9
O3—N4—C4	118.5 (3)	C15ⁱ—O6—H6A	109.4
O3—N4—C4	118.5 (3)	C15ⁱ—C14—C14ⁱ	74.4 (13)
N1—C1—C6	120.5 (3)	C15ⁱ—C14—C15	124.3 (13)
N1—C1—C2	122.8 (3)	C14ⁱ—C14—C15	49.9 (12)
C6—C1—C2	116.7 (3)	C15ⁱ—C14—O6	92.5 (13)
C3—C2—C1	121.3 (3)	C14ⁱ—C14—O6	124.7 (14)
C3—C2—N3	116.1 (3)	C15—C14—O6	117.0 (10)
C1—C2—N3	122.5 (3)	C14ⁱ—C14—H14A	65.2
C4—C3—C2	119.4 (3)	C15—C14—H14A	113.8
C4—C3—H3	120.3	O6—C14—H14A	108.3
C2—C3—H3	120.3	C15ⁱ—C14—H14B	112.3
C3—C4—C5	121.3 (3)	C14ⁱ—C14—H14B	127.7
C3—C4—N4	119.0 (3)	C15—C14—H14B	102.9
C5—C4—N4	119.7 (3)	O6—C14—H14B	107.2
C6—C5—C4	119.9 (3)	H14A—C14—H14B	106.8
C6—C5—H5A	120.0	C14ⁱ—C15—C14	55.7 (13)
C4—C5—H5A	120.0	C14ⁱ—C15—O6ⁱ	50.3 (8)
C5—C6—C1	121.3 (3)	C14—C15—O6ⁱ	90.5 (11)
C5—C6—H6	119.3	C14ⁱ—C15—H15A	81.5
C1—C6—H6	119.3	C14—C15—H15A	109.7
N2—C7—C8	122.5 (3)	C14ⁱ—C15—H15B	74.1
N2—C7—H7	118.8	C14—C15—H15B	108.2
C8—C7—H7	118.8	O6ⁱ—C15—H15B	93.5
C13—C8—C9	118.2 (3)	H15A—C15—H15B	109.5
C13—C8—C7	118.9 (3)	C14ⁱ—C15—H15C	165.6
C9—C8—C7	122.9 (3)	C14—C15—H15C	110.5
C10—C9—C8	120.5 (3)	O6ⁱ—C15—H15C	140.8
C10—C9—H9	119.7	H15A—C15—H15C	109.5
C8—C9—H9	119.7	H15B—C15—H15C	109.5

Symmetry code: (i) −x+2, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.89	1.97	2.605 (3)	127
O6—H6A···O3	0.85	1.86	2.702 (9)	174
O5—H5···O6ⁱⁱ	0.85	2.26	2.882 (9)	130
O5—H5···O4ⁱⁱⁱ	0.85	2.47	3.116 (4)	133
O5—H5···O3ⁱⁱⁱ	0.85	2.60	3.404 (4)	159
N1—H1···O2^iv	0.89	2.63	3.449 (4)	153

Symmetry codes: (ii) −x+1, −y, −z+1; (iii) x−1, y−1, z−1; (iv) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀N₄O₅·0.5C₂H₆O
M_r	325.28
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.0935 (16), 7.2888 (17), 14.458 (3)
α, β, γ (°)	100.156 (4), 96.378 (4), 100.604 (4)
V (Å³)	715.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.15 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.982, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	4065, 2776, 1543
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.230, 1.04
No. of reflections	2776
No. of parameters	227
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.25

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.89	1.97	2.605 (3)	126.7
O6—H6A···O3	0.85	1.86	2.702 (9)	173.5
O5—H5···O6ⁱ	0.85	2.26	2.882 (9)	129.7
O5—H5···O4ⁱⁱ	0.85	2.47	3.116 (4)	133.0
O5—H5···O3ⁱⁱ	0.85	2.60	3.404 (4)	158.9
N1—H1···O2ⁱⁱⁱ	0.89	2.63	3.449 (4)	152.9

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Baughman, R. G., Martin, K. L., Singh, R. K. & Stoffer, J. O. (2004). Acta Cryst. C60, o103–o106. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ji, N.-N. & Shi, Z.-Q. (2008). Acta Cryst. E64, o2141. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, Z.-Q., Ji, N.-N. & Li, X.-Y. (2008). Acta Cryst. E64, o2135. Web of Science CrossRef IUCr Journals Google Scholar

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Volume 66| Part 12| December 2010| Page o3142

https://doi.org/10.1107/S1600536810045782

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

4-{[2-(2,4-Di­nitro­phen­yl)hydrazinyl­­idene]meth­yl}phenol ethanol hemisolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

4-{[2-(2,4-Dinitrophenyl)hydrazinylidene]methyl}phenol ethanol hemisolvate