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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 9| September 2010| Page o2205
https://doi.org/10.1107/S1600536810029983

3-Eth­­oxy-2-hy­dr­oxy­benzaldehyde 2,4-di­nitro­phenylhydrazone N,N-di­methyl­formamide monosolvate

Lin-xiu Zhao,a* Jian-lan Cuia and Duan-lin Caoa

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 of the title compound, C15H14N4O6·C3H7NO, was obtained from the condensation reaction of 3-eth­oxy-2-hy­droxy­benzaldehyde and 2,4-dinitro­phenyl­hydrazine. The dihedral angle between the benzene rings is 3.05 (10)° and intra­molecular N—H⋯O and O—H⋯O hydrogen bonds generate S(6) and S(5) ring motifs, respectively. In the crystal, the Schiff base and dimethyl­formamide solvent mol­ecules are linked by an O—H⋯O hydrogen bond.

Related literature

For a related structure and background references, see: Zhao et al. (2010[Zhao, L., Cao, D. & Cui, J. (2010). Acta Cryst. E66, o2204.]).

[Scheme 1]

Experimental

Crystal data

  • C15H14N4O6·C3N7NO

  • Mr = 419.40

  • Triclinic, [P \overline 1]

  • a = 7.1070 (6) Å

  • b = 7.7200 (7) Å

  • c = 19.4790 (19) Å

  • α = 84.677 (7)°

  • β = 81.562 (7)°

  • γ = 68.707 (8)°

  • V = 984.10 (16) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 293 K

  • 0.20 × 0.18 × 0.17 mm
Data collection

  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.974, Tmax = 0.978

  • 6788 measured reflections

  • 4011 independent reflections

  • 1655 reflections with I > 2σ(I)

  • Rint = 0.028
Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.076

  • S = 0.74

  • 4011 reflections

  • 271 parameters

  • H-atom parameters constrained

  • Δρmax = 0.12 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2A⋯O3 0.86 2.01 2.6349 (19) 128
O1—H1B⋯O2 0.82 2.21 2.6581 (15) 115
O1—H1B⋯O7i 0.82 1.98 2.726 (2) 150
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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/S1600536810029983/hb5578sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810029983/hb5578Isup2.hkl

checkCIF report


Comment top

As part of our ongoing studies of Schiff bases (Zhao et al., 2010), we have 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 is nearly planar, making a dihedral angle of 3.05 (10)°.

Intramolecular N—H···O and O—H···O hydrogen bonds (Table 2) help to establish the planar conformation of the molecule.

Related literature top

For a related structure and background references, see: Zhao et al. (2010).

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 351k, 3-Ethoxy-2-hydroxybenzaldehyde (1 mmol, 0.166 g) in ethanol (8 mm l) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized from DMF, red blocks of (I) were obtained after one week.

Refinement top

All H atoms were positioned geometrically and refined as riding with C—H = 0.93 (aromatic), 0.97 (methylene), 0.96 Å (methyl) and N—H = 0.86 Å, with Uiso(H) = 1.2Ueq(CH, CH2 or NH) and Uiso(H) = 1.5Ueq(C).

Structure description top

As part of our ongoing studies of Schiff bases (Zhao et al., 2010), we have 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 is nearly planar, making a dihedral angle of 3.05 (10)°.

Intramolecular N—H···O and O—H···O hydrogen bonds (Table 2) help to establish the planar conformation of the molecule.

For a related structure and background references, see: Zhao et al. (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: 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
[Figure 1] Fig. 1. : the molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. Intramolecular hydrogen bonds are shown as dashed lines.
3-Ethoxy-2-hydroxybenzaldehyde 2,4-dinitrophenylhydrazone N,N-dimethylformamide monosolvate top
Crystal data top
C15H14N4O6·C3N7NOZ = 2
Mr = 419.40F(000) = 440
Triclinic, P1Dx = 1.415 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1070 (6) ÅCell parameters from 1739 reflections
b = 7.7200 (7) Åθ = 3.1–26.4°
c = 19.4790 (19) ŵ = 0.11 mm−1
α = 84.677 (7)°T = 293 K
β = 81.562 (7)°Block, red
γ = 68.707 (8)°0.20 × 0.18 × 0.17 mm
V = 984.10 (16) Å3
Data collection top
Bruker SMART CCD
diffractometer		4011 independent reflections
Radiation source: fine-focus sealed tube1655 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω scansθmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		h = −8→8
Tmin = 0.974, Tmax = 0.978k = −9→9
6788 measured reflectionsl = −14→24
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H-atom parameters constrained
S = 0.74 w = 1/[σ2(Fo2) + (0.0323P)2]
where P = (Fo2 + 2Fc2)/3
4011 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.12 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
Crystal data top
C15H14N4O6·C3N7NOγ = 68.707 (8)°
Mr = 419.40V = 984.10 (16) Å3
Triclinic, P1Z = 2
a = 7.1070 (6) ÅMo Kα radiation
b = 7.7200 (7) ŵ = 0.11 mm−1
c = 19.4790 (19) ÅT = 293 K
α = 84.677 (7)°0.20 × 0.18 × 0.17 mm
β = 81.562 (7)°
Data collection top
Bruker SMART CCD
diffractometer		4011 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		1655 reflections with I > 2σ(I)
Tmin = 0.974, Tmax = 0.978Rint = 0.028
6788 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.076H-atom parameters constrained
S = 0.74Δρmax = 0.12 e Å−3
4011 reflectionsΔρmin = −0.23 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
xyzUiso*/Ueq
N20.7004 (2)0.1384 (2)0.44923 (8)0.0440 (4)
H2A0.67980.23860.46990.053*
N10.7508 (2)−0.02993 (19)0.48584 (9)0.0428 (4)
O10.82321 (18)−0.01826 (15)0.68544 (7)0.0526 (4)
H1B0.8425−0.03010.72640.079*
O20.8899 (2)−0.31145 (17)0.77409 (7)0.0581 (4)
N30.6101 (2)0.4898 (2)0.36575 (11)0.0510 (5)
C10.8135 (3)−0.1943 (2)0.59413 (10)0.0375 (5)
C100.6832 (3)0.1462 (2)0.38088 (10)0.0350 (5)
C150.7047 (3)−0.0166 (2)0.34804 (10)0.0412 (5)
H15A0.7291−0.12780.37430.049*
O30.6142 (2)0.49976 (17)0.42849 (8)0.0680 (5)
C30.8759 (3)−0.3431 (3)0.70742 (11)0.0429 (5)
C130.6554 (3)0.1492 (3)0.23938 (10)0.0442 (5)
O40.5797 (2)0.62599 (17)0.32584 (8)0.0748 (5)
C60.8332 (2)−0.3652 (2)0.56975 (10)0.0435 (5)
H6A0.8181−0.37350.52370.052*
C110.6432 (3)0.3112 (2)0.33864 (11)0.0380 (5)
C120.6307 (3)0.3106 (3)0.26862 (11)0.0455 (5)
H12A0.60540.42040.24150.055*
C20.8389 (3)−0.1847 (2)0.66297 (11)0.0390 (5)
C90.7639 (2)−0.0246 (2)0.54994 (11)0.0428 (5)
H9A0.74160.08850.56880.051*
O50.6626 (2)0.0037 (2)0.14012 (8)0.0852 (5)
C140.6907 (3)−0.0156 (2)0.27938 (10)0.0448 (5)
H14A0.7046−0.12470.25910.054*
O70.1362 (3)−0.0784 (2)0.18791 (8)0.0778 (5)
N40.6425 (3)0.1503 (3)0.16536 (10)0.0631 (5)
C40.8958 (3)−0.5105 (3)0.68260 (11)0.0491 (6)
H4A0.9233−0.61650.71200.059*
C50.8748 (3)−0.5210 (3)0.61339 (11)0.0494 (5)
H5A0.8890−0.63450.59660.059*
N50.3469 (3)−0.1964 (2)0.09163 (11)0.0652 (5)
O60.6127 (3)0.2979 (2)0.13149 (8)0.0938 (6)
C160.3049 (4)−0.1592 (3)0.15849 (13)0.0624 (6)
H16A0.4130−0.19800.18490.075*
C80.9158 (4)−0.3863 (3)0.89285 (12)0.0870 (8)
H8A0.9375−0.48490.92800.131*
H8B0.7849−0.29190.90410.131*
H8C1.0198−0.33330.89050.131*
C70.9238 (3)−0.4618 (3)0.82428 (11)0.0698 (7)
H7A1.0557−0.55700.81220.084*
H7B0.8201−0.51670.82610.084*
C180.5516 (4)−0.2863 (3)0.05946 (14)0.1133 (10)
H18A0.6435−0.31920.09410.170*
H18B0.5874−0.20300.02480.170*
H18C0.5606−0.39660.03810.170*
C170.1878 (4)−0.1365 (4)0.04773 (13)0.1068 (9)
H17A0.0594−0.07900.07510.160*
H17B0.1852−0.24200.02590.160*
H17C0.2122−0.04850.01270.160*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0558 (12)0.0373 (9)0.0405 (12)−0.0173 (8)−0.0075 (9)−0.0046 (8)
N10.0468 (11)0.0406 (10)0.0394 (11)−0.0138 (8)−0.0066 (9)0.0001 (9)
O10.0710 (10)0.0503 (8)0.0399 (9)−0.0223 (7)−0.0123 (8)−0.0057 (7)
O20.0787 (11)0.0601 (9)0.0364 (10)−0.0255 (7)−0.0109 (8)0.0032 (8)
N30.0521 (12)0.0397 (10)0.0646 (15)−0.0199 (8)−0.0064 (11)−0.0046 (11)
C10.0310 (12)0.0441 (12)0.0357 (13)−0.0121 (9)−0.0008 (10)−0.0038 (10)
C100.0318 (12)0.0361 (11)0.0369 (13)−0.0127 (9)−0.0012 (10)−0.0031 (10)
C150.0444 (13)0.0343 (11)0.0435 (14)−0.0127 (9)−0.0045 (11)−0.0017 (10)
O30.0994 (13)0.0524 (8)0.0593 (12)−0.0308 (8)−0.0135 (10)−0.0145 (8)
C30.0377 (13)0.0500 (12)0.0391 (14)−0.0127 (10)−0.0051 (11)−0.0033 (12)
C130.0430 (13)0.0568 (13)0.0356 (14)−0.0222 (10)−0.0019 (11)−0.0014 (12)
O40.1047 (12)0.0379 (8)0.0859 (13)−0.0298 (8)−0.0211 (10)0.0116 (9)
C60.0410 (13)0.0485 (11)0.0371 (13)−0.0104 (9)0.0009 (10)−0.0142 (11)
C110.0361 (12)0.0322 (10)0.0451 (14)−0.0125 (9)−0.0001 (11)−0.0042 (10)
C120.0416 (13)0.0453 (12)0.0495 (15)−0.0186 (10)−0.0032 (11)0.0081 (12)
C20.0339 (12)0.0384 (11)0.0436 (14)−0.0112 (9)−0.0023 (10)−0.0076 (11)
C90.0412 (13)0.0473 (12)0.0415 (14)−0.0173 (10)−0.0017 (11)−0.0086 (11)
O50.1203 (15)0.1035 (12)0.0488 (11)−0.0576 (11)−0.0052 (10)−0.0211 (10)
C140.0449 (13)0.0449 (12)0.0431 (14)−0.0143 (9)0.0006 (11)−0.0114 (11)
O70.0783 (12)0.1091 (13)0.0495 (11)−0.0368 (10)0.0068 (10)−0.0288 (10)
N40.0707 (14)0.0849 (14)0.0423 (13)−0.0399 (12)−0.0008 (10)−0.0045 (12)
C40.0444 (14)0.0444 (12)0.0520 (16)−0.0096 (10)−0.0038 (12)0.0008 (11)
C50.0497 (14)0.0396 (11)0.0552 (16)−0.0109 (9)−0.0013 (12)−0.0120 (11)
N50.0778 (16)0.0675 (12)0.0480 (14)−0.0255 (11)0.0068 (12)−0.0146 (11)
O60.1387 (16)0.1069 (13)0.0483 (12)−0.0604 (11)−0.0215 (11)0.0212 (10)
C160.079 (2)0.0626 (15)0.0550 (18)−0.0345 (14)−0.0119 (15)−0.0054 (13)
C80.106 (2)0.1054 (19)0.0458 (18)−0.0343 (16)−0.0143 (16)0.0096 (16)
C70.0826 (18)0.0732 (15)0.0496 (16)−0.0253 (12)−0.0120 (14)0.0128 (14)
C180.104 (2)0.097 (2)0.125 (3)−0.0310 (18)0.041 (2)−0.0406 (19)
C170.135 (3)0.130 (2)0.0534 (19)−0.0400 (19)−0.0210 (18)−0.0117 (16)
Geometric parameters (Å, º) top
N2—C101.348 (2)C12—H12A0.9300
N2—N11.3751 (17)C9—H9A0.9300
N2—H2A0.8600O5—N41.228 (2)
N1—C91.271 (2)C14—H14A0.9300
O1—C21.3569 (19)O7—C161.215 (2)
O1—H1B0.8200N4—O61.2263 (18)
O2—C31.368 (2)C4—C51.391 (3)
O2—C71.4200 (19)C4—H4A0.9300
N3—O41.2204 (16)C5—H5A0.9300
N3—O31.2369 (19)N5—C161.327 (3)
N3—C111.448 (2)N5—C171.433 (3)
C1—C21.391 (2)N5—C181.439 (3)
C1—C61.395 (2)C16—H16A0.9300
C1—C91.458 (2)C8—C71.492 (3)
C10—C111.411 (2)C8—H8A0.9600
C10—C151.412 (2)C8—H8B0.9600
C15—C141.355 (2)C8—H8C0.9600
C15—H15A0.9300C7—H7A0.9700
C3—C41.374 (2)C7—H7B0.9700
C3—C21.397 (2)C18—H18A0.9600
C13—C121.361 (2)C18—H18B0.9600
C13—C141.389 (2)C18—H18C0.9600
C13—N41.457 (2)C17—H17A0.9600
C6—C51.372 (2)C17—H17B0.9600
C6—H6A0.9300C17—H17C0.9600
C11—C121.380 (3)
C10—N2—N1119.90 (16)C13—C14—H14A120.2
C10—N2—H2A120.1O6—N4—O5123.4 (2)
N1—N2—H2A120.1O6—N4—C13118.2 (2)
C9—N1—N2115.76 (16)O5—N4—C13118.40 (19)
C2—O1—H1B109.5C3—C4—C5119.78 (18)
C3—O2—C7118.68 (16)C3—C4—H4A120.1
O4—N3—O3121.94 (17)C5—C4—H4A120.1
O4—N3—C11118.91 (18)C6—C5—C4120.52 (19)
O3—N3—C11119.16 (16)C6—C5—H5A119.7
C2—C1—C6119.10 (17)C4—C5—H5A119.7
C2—C1—C9118.88 (18)C16—N5—C17120.2 (2)
C6—C1—C9122.02 (19)C16—N5—C18122.2 (2)
N2—C10—C11123.56 (18)C17—N5—C18117.5 (2)
N2—C10—C15119.93 (16)O7—C16—N5125.1 (2)
C11—C10—C15116.50 (19)O7—C16—H16A117.4
C14—C15—C10121.93 (17)N5—C16—H16A117.4
C14—C15—H15A119.0C7—C8—H8A109.5
C10—C15—H15A119.0C7—C8—H8B109.5
O2—C3—C4126.23 (18)H8A—C8—H8B109.5
O2—C3—C2113.64 (18)C7—C8—H8C109.5
C4—C3—C2120.1 (2)H8A—C8—H8C109.5
C12—C13—C14120.79 (19)H8B—C8—H8C109.5
C12—C13—N4119.36 (18)O2—C7—C8107.53 (18)
C14—C13—N4119.8 (2)O2—C7—H7A110.2
C5—C6—C1120.36 (19)C8—C7—H7A110.2
C5—C6—H6A119.8O2—C7—H7B110.2
C1—C6—H6A119.8C8—C7—H7B110.2
C12—C11—C10121.16 (19)H7A—C7—H7B108.5
C12—C11—N3116.24 (17)N5—C18—H18A109.5
C10—C11—N3122.59 (19)N5—C18—H18B109.5
C13—C12—C11119.91 (18)H18A—C18—H18B109.5
C13—C12—H12A120.0N5—C18—H18C109.5
C11—C12—H12A120.0H18A—C18—H18C109.5
O1—C2—C1118.32 (16)H18B—C18—H18C109.5
O1—C2—C3121.61 (19)N5—C17—H17A109.5
C1—C2—C3120.06 (18)N5—C17—H17B109.5
N1—C9—C1120.57 (19)H17A—C17—H17B109.5
N1—C9—H9A119.7N5—C17—H17C109.5
C1—C9—H9A119.7H17A—C17—H17C109.5
C15—C14—C13119.69 (19)H17B—C17—H17C109.5
C15—C14—H14A120.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O30.862.012.6349 (19)128
O1—H1B···O20.822.212.6581 (15)115
O1—H1B···O7i0.821.982.726 (2)150
Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formulaC15H14N4O6·C3N7NO
Mr419.40
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.1070 (6), 7.7200 (7), 19.4790 (19)
α, β, γ (°)84.677 (7), 81.562 (7), 68.707 (8)
V (Å3)984.10 (16)
Z2
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.20 × 0.18 × 0.17
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax0.974, 0.978
No. of measured, independent and
observed [I > 2σ(I)] reflections		6788, 4011, 1655
Rint0.028
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.076, 0.74
No. of reflections4011
No. of parameters271
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.12, −0.23

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O30.862.012.6349 (19)128
O1—H1B···O20.822.212.6581 (15)115
O1—H1B···O7i0.821.982.726 (2)150
Symmetry code: (i) −x+1, −y, −z+1.
 

References

First citationBruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationZhao, L., Cao, D. & Cui, J. (2010). Acta Cryst. E66, o2204.  Web of Science CSD CrossRef 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
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ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2205
https://doi.org/10.1107/S1600536810029983
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