2-Hydroxy-3-methoxybenzaldehyde 2,4-dinitrophenylhydrazone pyridine monosolvate

Zhao, L.; Cao, D.; Cui, J.

doi:10.1107/S1600536810029971

organic compounds

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Volume 66| Part 9| September 2010| Page o2204

https://doi.org/10.1107/S1600536810029971

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2-Hydroxy-3-methoxybenzaldehyde 2,4-dinitrophenylhydrazone pyridine monosolvate

Lin-xiu Zhao,^a ^* Duan-lin Cao ^a and Jian-lan Cui ^a

^aCollege of Chemical Engineering and Environment, North University of China, Taiyuan 030051, People's Republic of China
^*Correspondence e-mail: zhaolinxiu126@126.com

(Received 25 July 2010; accepted 28 July 2010; online 4 August 2010)

The Schiff base molecule of the title compound, C₁₄H₁₂N₄O₆·C₅H₅N, was obtained from the condensation reaction of 2-hydroxy-3-methoxybenzaldehyde and 2,4-dinitrophenylhydrazine. The C=N bond of the Schiff base has a trans arrangement and the dihedral angle between the two benzene rings is 3.49 (10)°. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring. In the crystal, O—H⋯O hydrogen bonds link the Schiff base molecules.

Related literature

For background to Schiff bases, see: Kahwa et al. (1986 ); Santos et al. (2001 ). For a related structure, see: Ohba (1996 ).

Experimental

Crystal data

C₁₄H₁₂N₄O₆·C₅H₅N
M_r = 411.38
Triclinic, $[P \overline 1]$
a = 6.9020 (18) Å
b = 7.6240 (12) Å
c = 19.073 (3) Å
α = 95.112 (13)°
β = 91.199 (17)°
γ = 107.024 (19)°
V = 954.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.21 × 0.19 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.973, T_max = 0.978
7517 measured reflections
4401 independent reflections
1852 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.143
S = 0.82
4401 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯O4ⁱ	0.82	2.53	3.319 (2)	162
N2—H2A⋯O3	0.86	2.03	2.635 (2)	126
Symmetry code: (i) -x+1, -y-1, -z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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/S1600536810029971/hb5577sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810029971/hb5577Isup2.hkl

checkCIF report

Comment top

The chemistry of Schiff base has attracted a great deal of interest in recent years. These compounds play an important role in the development of various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of our in the study of the coordination chemistry of Schiff bases, we synthesized the title compound, (I), and determined its crystal structure.

The molecular structure of (I) is shown in Fig.1. The benzene ring and the 2,4-dinitro benzene ring are nearly coplanar, making a dihedral angle of 3.49 (10)°. The dinitro group is coplanar with C9-benzene ring with a dihedral angle of 0.58 (8). Bond lengths and bond angles agree with those of other dinitrophenylhydrazone derivatives (Ohba, 1996).

Intramolecular N—H···O and intermolecular O—H···O hydrogen bonds are certainly responsible for the planar conformation of the molecule.

Related literature top

For background to Schiff bases, see: Kahwa et al. (1986); Santos et al. (2001). For a related structure, see: Ohba (1996).

Experimental top

2,4-Dinitrophenylhydrazine (1 mmol, 0.198 g) was dissolved in anhydrous ethanol (15 ml), H₂SO₄(98%, 0.5 ml) was then added and the mixture was stirred for several minitutes at 351 K. Then, 2-hydroxy-3-methoxybenzaldehyde (1 mmol, 0.152 g) in ethanol (8 mm l) was added dropwise and the mixture was stirred at refluxing temperature for 3 h. The product was isolated and recrystallized from pyridine, red blocks of (I) were obtained after two weeks.

Structure description top

Intramolecular N—H···O and intermolecular O—H···O hydrogen bonds are certainly responsible for the planar conformation of the molecule.

For background to Schiff bases, see: Kahwa et al. (1986); Santos et al. (2001). For a related structure, see: Ohba (1996).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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. : The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. The intramolecular hydrogen bond is indicatd with dashed lines.
	Fig. 2. The partial packing of (I).

2-Hydroxy-3-methoxybenzaldehyde 2,4-dinitrophenylhydrazone pyridine monosolvate top

Crystal data top

C₁₄H₁₂N₄O₆·C₅H₅N	Z = 2
M_r = 411.38	F(000) = 418
Triclinic, P1	D_x = 1.431 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9020 (18) Å	Cell parameters from 1741 reflections
b = 7.6240 (12) Å	θ = 3.2–29.3°
c = 19.073 (3) Å	µ = 0.11 mm⁻¹
α = 95.112 (13)°	T = 293 K
β = 91.199 (17)°	Block, red
γ = 107.024 (19)°	0.21 × 0.19 × 0.17 mm
V = 954.7 (3) Å³

Data collection top

Bruker SMART CCD diffractometer	4401 independent reflections
Radiation source: fine-focus sealed tube	1852 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 29.3°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −8→9
T_min = 0.973, T_max = 0.978	k = −10→8
7517 measured reflections	l = −23→25

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 0.82	w = 1/[σ²(F_o²) + (0.078P)²] where P = (F_o² + 2F_c²)/3
4401 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₄H₁₂N₄O₆·C₅H₅N	γ = 107.024 (19)°
M_r = 411.38	V = 954.7 (3) Å³
Triclinic, P1	Z = 2
a = 6.9020 (18) Å	Mo Kα radiation
b = 7.6240 (12) Å	µ = 0.11 mm⁻¹
c = 19.073 (3) Å	T = 293 K
α = 95.112 (13)°	0.21 × 0.19 × 0.17 mm
β = 91.199 (17)°

Data collection top

Bruker SMART CCD diffractometer	4401 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1852 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.978	R_int = 0.020
7517 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 0.82	Δρ_max = 0.31 e Å⁻³
4401 reflections	Δρ_min = −0.38 e Å⁻³
271 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
N1	0.7466 (3)	0.0112 (2)	0.01896 (10)	0.0424 (5)
N3	0.6500 (3)	−0.4948 (2)	−0.11703 (12)	0.0485 (5)
O1	0.7209 (2)	0.00916 (18)	0.23110 (8)	0.0549 (5)
H1B	0.6315	−0.0690	0.2069	0.082*
C1	0.7623 (3)	0.1767 (3)	0.13134 (12)	0.0390 (5)
N2	0.7090 (3)	−0.1535 (2)	−0.02176 (10)	0.0429 (5)
H2A	0.6742	−0.2561	−0.0030	0.051*
C2	0.7567 (3)	0.1720 (3)	0.20412 (13)	0.0412 (6)
O3	0.6370 (3)	−0.5111 (2)	−0.05341 (11)	0.0677 (5)
C12	0.7671 (3)	−0.1328 (3)	−0.23637 (12)	0.0386 (5)
O2	0.7845 (3)	0.3159 (2)	0.31832 (9)	0.0670 (5)
C8	0.7250 (3)	0.0051 (3)	0.08483 (13)	0.0399 (5)
H8A	0.6856	−0.1080	0.1035	0.048*
C10	0.7001 (3)	−0.3115 (2)	−0.13946 (12)	0.0367 (5)
C3	0.7921 (3)	0.3370 (3)	0.24820 (13)	0.0476 (6)
C6	0.8044 (3)	0.3474 (3)	0.10356 (13)	0.0477 (6)
H6A	0.8102	0.3526	0.0551	0.057*
C14	0.7760 (3)	0.0185 (3)	−0.12116 (12)	0.0400 (5)
H14A	0.7952	0.1268	−0.0918	0.048*
C11	0.7186 (3)	−0.3009 (3)	−0.21097 (12)	0.0399 (6)
H11A	0.6983	−0.4075	−0.2415	0.048*
O4	0.6221 (3)	−0.6271 (2)	−0.16096 (10)	0.0679 (6)
N4	0.7912 (3)	−0.1221 (3)	−0.31121 (11)	0.0534 (5)
C5	0.8368 (3)	0.5061 (3)	0.14741 (15)	0.0549 (7)
H5A	0.8634	0.6184	0.1284	0.066*
C13	0.7946 (3)	0.0271 (3)	−0.19136 (12)	0.0407 (6)
H13A	0.8261	0.1407	−0.2096	0.049*
O5	0.8451 (3)	0.0308 (2)	−0.33278 (10)	0.0713 (6)
C9	0.7280 (3)	−0.1511 (3)	−0.09170 (12)	0.0354 (5)
C4	0.8307 (3)	0.5021 (3)	0.21998 (15)	0.0533 (7)
H4A	0.8528	0.6111	0.2493	0.064*
O6	0.7599 (3)	−0.2658 (3)	−0.35043 (10)	0.0813 (6)
C18	0.3624 (4)	0.0818 (3)	−0.36369 (12)	0.0432 (6)
H18A	0.3344	0.0297	−0.3214	0.052*
C7	0.8415 (5)	0.4749 (4)	0.36657 (16)	0.0861 (10)
H7A	0.8292	0.4398	0.4138	0.129*
H7B	0.7546	0.5500	0.3588	0.129*
H7C	0.9796	0.5435	0.3601	0.129*
N5	0.2789 (4)	0.0847 (4)	−0.48479 (16)	0.0962 (9)
C19	0.2479 (4)	0.0124 (4)	−0.42066 (17)	0.0663 (8)
H19A	0.1386	−0.0923	−0.4179	0.080*
C17	0.5183 (5)	0.2274 (4)	−0.36801 (16)	0.0732 (9)
H17A	0.6012	0.2766	−0.3277	0.088*
C15	0.4455 (5)	0.2404 (4)	−0.48748 (17)	0.0736 (8)
H15A	0.4736	0.2948	−0.5293	0.088*
C16	0.5660 (5)	0.3114 (4)	−0.42861 (18)	0.0760 (9)
H16A	0.6783	0.4146	−0.4293	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0478 (11)	0.0423 (10)	0.0358 (13)	0.0098 (8)	0.0002 (9)	0.0099 (9)
N3	0.0542 (13)	0.0366 (11)	0.0584 (16)	0.0161 (9)	0.0098 (11)	0.0130 (11)
O1	0.0749 (11)	0.0411 (9)	0.0432 (11)	0.0083 (7)	−0.0017 (9)	0.0069 (7)
C1	0.0306 (11)	0.0417 (12)	0.0435 (16)	0.0081 (9)	−0.0015 (10)	0.0074 (10)
N2	0.0563 (12)	0.0342 (9)	0.0379 (12)	0.0107 (8)	0.0036 (10)	0.0109 (8)
C2	0.0362 (12)	0.0440 (12)	0.0425 (16)	0.0099 (9)	−0.0003 (11)	0.0060 (11)
O3	0.1054 (15)	0.0491 (10)	0.0544 (14)	0.0253 (9)	0.0186 (11)	0.0247 (9)
C12	0.0393 (12)	0.0444 (12)	0.0343 (14)	0.0142 (9)	0.0037 (10)	0.0097 (10)
O2	0.0895 (13)	0.0634 (10)	0.0400 (12)	0.0122 (9)	0.0021 (10)	−0.0021 (9)
C8	0.0380 (13)	0.0438 (12)	0.0390 (15)	0.0116 (9)	−0.0002 (11)	0.0123 (10)
C10	0.0346 (12)	0.0317 (11)	0.0448 (15)	0.0093 (9)	0.0043 (10)	0.0104 (10)
C3	0.0421 (13)	0.0523 (14)	0.0452 (17)	0.0094 (10)	0.0008 (12)	0.0036 (12)
C6	0.0434 (13)	0.0469 (13)	0.0480 (16)	0.0039 (10)	−0.0011 (12)	0.0123 (11)
C14	0.0472 (13)	0.0343 (11)	0.0377 (15)	0.0100 (9)	0.0037 (11)	0.0070 (10)
C11	0.0398 (13)	0.0358 (11)	0.0430 (16)	0.0102 (9)	0.0029 (11)	0.0016 (10)
O4	0.0970 (14)	0.0336 (9)	0.0729 (14)	0.0187 (9)	0.0124 (11)	0.0037 (9)
N4	0.0635 (14)	0.0614 (13)	0.0397 (14)	0.0235 (11)	0.0074 (10)	0.0110 (11)
C5	0.0510 (15)	0.0418 (13)	0.069 (2)	0.0058 (11)	0.0002 (13)	0.0178 (12)
C13	0.0457 (13)	0.0338 (11)	0.0427 (15)	0.0083 (9)	0.0071 (11)	0.0150 (10)
O5	0.1020 (15)	0.0721 (12)	0.0476 (13)	0.0311 (10)	0.0184 (10)	0.0256 (9)
C9	0.0302 (11)	0.0384 (11)	0.0376 (15)	0.0082 (9)	0.0039 (10)	0.0101 (10)
C4	0.0508 (15)	0.0434 (13)	0.060 (2)	0.0067 (11)	−0.0025 (13)	−0.0023 (12)
O6	0.1247 (17)	0.0754 (12)	0.0429 (12)	0.0308 (11)	0.0063 (11)	−0.0032 (10)
C18	0.0617 (15)	0.0504 (13)	0.0200 (13)	0.0172 (12)	0.0036 (11)	0.0137 (10)
C7	0.115 (3)	0.084 (2)	0.053 (2)	0.0256 (18)	0.0025 (18)	−0.0192 (16)
N5	0.102 (2)	0.120 (2)	0.080 (2)	0.0501 (18)	0.0147 (17)	0.0221 (18)
C19	0.0695 (19)	0.0749 (17)	0.058 (2)	0.0208 (14)	0.0169 (16)	0.0237 (15)
C17	0.099 (2)	0.0744 (19)	0.054 (2)	0.0404 (17)	−0.0206 (18)	0.0007 (16)
C15	0.084 (2)	0.0792 (19)	0.067 (2)	0.0295 (17)	0.0219 (18)	0.0330 (17)
C16	0.081 (2)	0.0683 (17)	0.079 (3)	0.0186 (15)	−0.0033 (19)	0.0186 (17)

Geometric parameters (Å, º) top

N1—C8	1.272 (3)	C14—C13	1.353 (3)
N1—N2	1.369 (2)	C14—C9	1.408 (3)
N3—O4	1.219 (2)	C14—H14A	0.9300
N3—O3	1.233 (2)	C11—H11A	0.9300
N3—C10	1.444 (3)	N4—O5	1.227 (2)
O1—C2	1.344 (2)	N4—O6	1.231 (2)
O1—H1B	0.8200	C5—C4	1.388 (4)
C1—C2	1.393 (3)	C5—H5A	0.9300
C1—C6	1.402 (3)	C13—H13A	0.9300
C1—C8	1.467 (3)	C4—H4A	0.9300
N2—C9	1.344 (3)	C18—C19	1.305 (3)
N2—H2A	0.8600	C18—C17	1.310 (3)
C2—C3	1.405 (3)	C18—H18A	0.9300
C12—C11	1.362 (3)	C7—H7A	0.9600
C12—C13	1.389 (3)	C7—H7B	0.9600
C12—N4	1.447 (3)	C7—H7C	0.9600
O2—C3	1.362 (3)	N5—C19	1.381 (4)
O2—C7	1.407 (3)	N5—C15	1.396 (4)
C8—H8A	0.9300	C19—H19A	0.9300
C10—C11	1.380 (3)	C17—C16	1.371 (4)
C10—C9	1.421 (3)	C17—H17A	0.9300
C3—C4	1.370 (3)	C15—C16	1.354 (4)
C6—C5	1.366 (3)	C15—H15A	0.9300
C6—H6A	0.9300	C16—H16A	0.9300

C8—N1—N2	117.18 (18)	O5—N4—C12	118.34 (19)
O4—N3—O3	122.35 (19)	O6—N4—C12	119.0 (2)
O4—N3—C10	119.5 (2)	C6—C5—C4	121.0 (2)
O3—N3—C10	118.15 (19)	C6—C5—H5A	119.5
C2—O1—H1B	109.5	C4—C5—H5A	119.5
C2—C1—C6	119.0 (2)	C14—C13—C12	120.38 (19)
C2—C1—C8	120.1 (2)	C14—C13—H13A	119.8
C6—C1—C8	120.8 (2)	C12—C13—H13A	119.8
C9—N2—N1	118.40 (17)	N2—C9—C14	119.45 (18)
C9—N2—H2A	120.8	N2—C9—C10	124.01 (19)
N1—N2—H2A	120.8	C14—C9—C10	116.5 (2)
O1—C2—C1	119.27 (19)	C3—C4—C5	119.7 (2)
O1—C2—C3	121.0 (2)	C3—C4—H4A	120.2
C1—C2—C3	119.7 (2)	C5—C4—H4A	120.2
C11—C12—C13	120.8 (2)	C19—C18—C17	117.8 (3)
C11—C12—N4	119.12 (19)	C19—C18—H18A	121.1
C13—C12—N4	120.05 (19)	C17—C18—H18A	121.1
C3—O2—C7	118.4 (2)	O2—C7—H7A	109.5
N1—C8—C1	119.9 (2)	O2—C7—H7B	109.5
N1—C8—H8A	120.1	H7A—C7—H7B	109.5
C1—C8—H8A	120.1	O2—C7—H7C	109.5
C11—C10—C9	121.50 (19)	H7A—C7—H7C	109.5
C11—C10—N3	115.69 (19)	H7B—C7—H7C	109.5
C9—C10—N3	122.8 (2)	C19—N5—C15	116.6 (3)
O2—C3—C4	125.1 (2)	C18—C19—N5	124.1 (3)
O2—C3—C2	114.6 (2)	C18—C19—H19A	118.0
C4—C3—C2	120.4 (2)	N5—C19—H19A	118.0
C5—C6—C1	120.3 (2)	C18—C17—C16	123.7 (3)
C5—C6—H6A	119.9	C18—C17—H17A	118.1
C1—C6—H6A	119.9	C16—C17—H17A	118.1
C13—C14—C9	121.41 (19)	C16—C15—N5	119.4 (3)
C13—C14—H14A	119.3	C16—C15—H15A	120.3
C9—C14—H14A	119.3	N5—C15—H15A	120.3
C12—C11—C10	119.34 (19)	C15—C16—C17	118.3 (3)
C12—C11—H11A	120.3	C15—C16—H16A	120.8
C10—C11—H11A	120.3	C17—C16—H16A	120.8
O5—N4—O6	122.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O4ⁱ	0.82	2.53	3.319 (2)	162
N2—H2A···O3	0.86	2.03	2.635 (2)	126

Symmetry code: (i) −x+1, −y−1, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂N₄O₆·C₅H₅N
M_r	411.38
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.9020 (18), 7.6240 (12), 19.073 (3)
α, β, γ (°)	95.112 (13), 91.199 (17), 107.024 (19)
V (Å³)	954.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.21 × 0.19 × 0.17

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.973, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	7517, 4401, 1852
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.689

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.143, 0.82
No. of reflections	4401
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.38

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O4ⁱ	0.82	2.53	3.319 (2)	161.8
N2—H2A···O3	0.86	2.03	2.635 (2)	126.3

Symmetry code: (i) −x+1, −y−1, −z.

References

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kahwa, I. A., Selbin, I., Hsieh, T. C. Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179–185. CrossRef CAS Web of Science Google Scholar
Ohba, S. (1996). Acta Cryst. C52, 2118–2119. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838–844. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 9| September 2010| Page o2204

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

2-Hy­droxy-3-methoxybenzaldehyde 2,4-di­nitro­phenylhydrazone pyridine monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

2-Hydroxy-3-methoxybenzaldehyde 2,4-dinitrophenylhydrazone pyridine monosolvate