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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2645.
Published online 2010 September 30. doi:  10.1107/S1600536810037517
PMCID: PMC2983342

1,5-Bis­[1-(2-hy­droxy­phen­yl)ethyl­idene]carbonohydrazide dimethyl­formamide monosolvate

Abstract

In the title compound, C17H18N4O3·C3H7NO, the main disubstituted urea and solvate mol­ecules are linked by pairs of N—H(...)O hydrogen bonds. In the main mol­ecules, the benzene rings form a dihedral angle of 15.59 (13)° a;nd two intra­molecular O—H(...)N hydrogen bonds influence the mol­ecular conformation. In the crystal structure, weak inter­molecular C—H(...)O inter­actions link the hydrogen-bonded pairs into chains along the b axis. The chains associate via C—H(...)π inter­actions.

Related literature

For a related structure, see: Zukerman-Schpector et al. (2009 [triangle]). For the bioactivity of carbonohydrazide derivatives, see: Loncle et al. (2004 [triangle]); Li et al. (2004 [triangle]).

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Object name is e-66-o2645-scheme1.jpg

Experimental

Crystal data

  • C17H18N4O3·C3H7NO
  • M r = 399.45
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2645-efi1.jpg
  • a = 16.6372 (15) Å
  • b = 7.5880 (9) Å
  • c = 16.2967 (14) Å
  • β = 94.472 (1)°
  • V = 2051.1 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 298 K
  • 0.47 × 0.46 × 0.23 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.958, T max = 0.979
  • 10277 measured reflections
  • 3596 independent reflections
  • 1712 reflections with I > 2σ(I)
  • R int = 0.059

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.165
  • S = 1.04
  • 3596 reflections
  • 263 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810037517/cv2762sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037517/cv2762Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge financial support by the Science Foundation of China (grant No. 20877037).

supplementary crystallographic information

Comment

Carbonohydrazide derivatives exhibit various bioactivities such as antibacteriale antifungal, anticonvulsant and anticancer activities (Loncle et al., 2004; Li et al., 2004). Herewith we present the crystal structure of the title compound (I), which is a new carbonohydrazide derivative.

Crystals of (I) comprise equal quantities of a disubstituted urea molecule (M) and a solvent N,N-dimethylformamide molecule (Fig. 1). The bond lengths and angles of the title compound are normal and correspond to those observed in N'',N'''-bis (1-(2-hydroxyphenyl)ethylidene)carbonohydrazide dimethyl sulfoxide solvate (Zukerman-Schpector et al., 2009). The molecular conformation of M is influenced by two intramolecular O—H···N hydrogen bonds (Table 1). Two benzene rings - C4-C9 and C12-C17, respectively - form a dihedral angle of 15.59 (13)°.

In the crystal structure, one M molecule and solvate molecule are paired via N—H···O hydrogen bonds (Table 1). Weak intermolecular C—H···O interactions (Table 1) link hydrogen-bonded pairs into chains along the b axis. The chains associate via C—H···π interactions (Table 1).

Experimental

2-Hydroxylacetophenone (10.0 mmol) and carbohydrazide (5.0 mmol) were mixed in 50 ml flash After stirring 3 h at 373 K, the resulting mixture was cooled to room temperature, and recrystalized from DMF, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C20H25N5O4: C 60.14, H 6.31, N 17.53%; found: C 60.23, H 6.45, N 17.64%.

Refinement

All H atoms were placed in geometrically idealized positions (N—H 0.86 and C—H = 0.93–0.96 Å, O—H= 0.82 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.2–1.5 Ueq of the parent atom.

Figures

Fig. 1.
The content of asymmetric unit of the title compound showing the atomic numbering scheme and 30% probability displacement ellipsoids.

Crystal data

C17H18N4O3·C3H7NOF(000) = 848
Mr = 399.45Dx = 1.294 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.6372 (15) ÅCell parameters from 1764 reflections
b = 7.5880 (9) Åθ = 2.5–21.7°
c = 16.2967 (14) ŵ = 0.09 mm1
β = 94.472 (1)°T = 298 K
V = 2051.1 (4) Å3Block, colourless
Z = 40.47 × 0.46 × 0.23 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer3596 independent reflections
Radiation source: fine-focus sealed tube1712 reflections with I > 2σ(I)
graphiteRint = 0.059
phi and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→19
Tmin = 0.958, Tmax = 0.979k = −9→9
10277 measured reflectionsl = −19→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.165w = 1/[σ2(Fo2) + (0.0542P)2 + 0.8303P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3596 reflectionsΔρmax = 0.22 e Å3
263 parametersΔρmin = −0.17 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0049 (10)

Special details

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)

xyzUiso*/Ueq
N10.15121 (15)0.6195 (3)0.48890 (15)0.0541 (7)
H10.15630.62540.54170.065*
N20.08378 (15)0.6805 (3)0.44431 (15)0.0491 (7)
N30.27455 (15)0.4912 (4)0.49563 (15)0.0555 (8)
H30.27560.50150.54830.067*
N40.33674 (15)0.4171 (3)0.45841 (15)0.0510 (7)
N50.23936 (17)0.5436 (4)0.78637 (16)0.0602 (8)
O10.20609 (13)0.5357 (3)0.37093 (14)0.0717 (8)
O20.02424 (14)0.7754 (4)0.30242 (13)0.0772 (8)
H2A0.05920.73620.33570.116*
O30.38946 (14)0.3282 (4)0.32185 (14)0.0826 (8)
H3A0.35770.37290.35180.124*
O40.22303 (16)0.6047 (4)0.65032 (15)0.0825 (9)
C10.20997 (19)0.5488 (4)0.4450 (2)0.0511 (9)
C20.0191 (2)0.7253 (5)0.57328 (18)0.0606 (10)
H2B0.04830.62430.59500.091*
H2C−0.03610.71720.58630.091*
H2D0.04280.83050.59730.091*
C30.02260 (19)0.7313 (4)0.48137 (18)0.0445 (8)
C4−0.04633 (18)0.7964 (4)0.42688 (19)0.0455 (8)
C5−0.04176 (19)0.8178 (4)0.3417 (2)0.0516 (9)
C6−0.1065 (2)0.8871 (5)0.2935 (2)0.0620 (10)
H6−0.10230.90330.23740.074*
C7−0.1762 (2)0.9319 (5)0.3270 (2)0.0706 (11)
H7−0.21930.97790.29400.085*
C8−0.1824 (2)0.9086 (5)0.4098 (3)0.0792 (12)
H8−0.22990.93810.43300.095*
C9−0.1183 (2)0.8417 (5)0.4584 (2)0.0634 (10)
H9−0.12350.82640.51430.076*
C100.40492 (19)0.3582 (5)0.59426 (19)0.0617 (10)
H10A0.42330.47210.61320.093*
H10B0.44260.26990.61480.093*
H10C0.35310.33460.61390.093*
C110.39830 (18)0.3552 (4)0.50206 (19)0.0470 (8)
C120.46219 (18)0.2798 (4)0.4551 (2)0.0485 (8)
C130.4547 (2)0.2668 (5)0.3684 (2)0.0588 (9)
C140.5149 (2)0.1875 (5)0.3275 (2)0.0756 (12)
H140.50820.17470.27060.091*
C150.5839 (2)0.1277 (5)0.3690 (3)0.0799 (12)
H150.62440.07720.34040.096*
C160.5933 (2)0.1423 (5)0.4528 (3)0.0738 (11)
H160.64040.10210.48130.089*
C170.5336 (2)0.2159 (4)0.4947 (2)0.0610 (10)
H170.54100.22370.55170.073*
C180.1982 (2)0.5477 (5)0.7144 (2)0.0700 (11)
H180.14580.50410.71160.084*
C190.3198 (2)0.6151 (6)0.7959 (2)0.0948 (14)
H19A0.33800.63990.74270.142*
H19B0.35530.53110.82390.142*
H19C0.31950.72180.82750.142*
C200.2055 (2)0.4702 (6)0.8576 (2)0.0931 (14)
H20A0.15030.43810.84360.140*
H20B0.20800.55610.90100.140*
H20C0.23560.36760.87570.140*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0494 (16)0.072 (2)0.0391 (15)0.0127 (15)−0.0055 (13)−0.0015 (14)
N20.0449 (16)0.0560 (18)0.0448 (16)0.0048 (14)−0.0071 (14)−0.0012 (13)
N30.0466 (16)0.077 (2)0.0421 (15)0.0101 (15)−0.0048 (13)−0.0037 (15)
N40.0432 (15)0.0593 (18)0.0493 (17)0.0022 (14)−0.0032 (13)−0.0033 (14)
N50.0661 (19)0.073 (2)0.0406 (17)0.0032 (17)0.0014 (15)0.0090 (15)
O10.0632 (15)0.106 (2)0.0436 (15)0.0167 (14)−0.0101 (12)−0.0117 (14)
O20.0669 (16)0.117 (2)0.0473 (14)0.0275 (15)0.0014 (13)0.0008 (14)
O30.0693 (17)0.125 (2)0.0517 (15)0.0146 (16)−0.0044 (13)−0.0063 (15)
O40.099 (2)0.107 (2)0.0418 (15)0.0096 (17)0.0026 (14)0.0109 (15)
C10.0455 (19)0.058 (2)0.048 (2)−0.0022 (17)−0.0055 (17)−0.0060 (18)
C20.064 (2)0.068 (2)0.049 (2)0.0049 (19)−0.0020 (17)0.0008 (18)
C30.049 (2)0.042 (2)0.0421 (19)−0.0037 (16)−0.0026 (16)−0.0045 (15)
C40.0480 (19)0.0426 (19)0.045 (2)0.0011 (16)−0.0012 (16)−0.0055 (16)
C50.051 (2)0.058 (2)0.044 (2)0.0062 (17)−0.0033 (17)−0.0065 (17)
C60.067 (2)0.068 (3)0.048 (2)0.007 (2)−0.0143 (19)−0.0001 (18)
C70.058 (2)0.081 (3)0.070 (3)0.019 (2)−0.015 (2)−0.005 (2)
C80.053 (2)0.103 (3)0.080 (3)0.022 (2)0.004 (2)−0.006 (3)
C90.057 (2)0.078 (3)0.055 (2)0.011 (2)0.0026 (19)−0.001 (2)
C100.061 (2)0.070 (2)0.053 (2)0.0082 (19)−0.0060 (17)0.0022 (19)
C110.0440 (19)0.047 (2)0.049 (2)−0.0037 (16)−0.0047 (16)−0.0020 (16)
C120.045 (2)0.046 (2)0.054 (2)−0.0063 (16)−0.0020 (17)0.0011 (17)
C130.053 (2)0.065 (2)0.057 (2)−0.0051 (19)−0.0014 (19)−0.0055 (19)
C140.070 (3)0.093 (3)0.066 (3)−0.004 (2)0.017 (2)−0.012 (2)
C150.068 (3)0.074 (3)0.101 (4)0.006 (2)0.028 (3)−0.004 (3)
C160.055 (2)0.072 (3)0.094 (3)0.012 (2)0.004 (2)0.011 (2)
C170.055 (2)0.058 (2)0.070 (2)0.0031 (19)−0.001 (2)0.0056 (19)
C180.070 (3)0.075 (3)0.064 (3)0.000 (2)−0.001 (2)−0.001 (2)
C190.072 (3)0.132 (4)0.078 (3)−0.003 (3)−0.009 (2)0.010 (3)
C200.116 (3)0.100 (3)0.066 (3)0.013 (3)0.024 (3)0.025 (2)

Geometric parameters (Å, °)

N1—C11.365 (4)C7—C81.372 (5)
N1—N21.369 (3)C7—H70.9300
N1—H10.8600C8—C91.375 (5)
N2—C31.283 (4)C8—H80.9302
N3—N41.361 (3)C9—H90.9300
N3—C11.374 (4)C10—C111.498 (4)
N3—H30.8600C10—H10A0.9600
N4—C111.289 (4)C10—H10B0.9600
N5—C181.311 (4)C10—H10C0.9600
N5—C191.440 (4)C11—C121.473 (4)
N5—C201.441 (4)C12—C171.394 (4)
O1—C11.208 (3)C12—C131.411 (4)
O2—C51.352 (3)C13—C141.384 (5)
O2—H2A0.8200C14—C151.364 (5)
O3—C131.358 (4)C14—H140.9300
O3—H3A0.8200C15—C161.367 (5)
O4—C181.232 (4)C15—H150.9299
C2—C31.504 (4)C16—C171.368 (5)
C2—H2B0.9600C16—H160.9300
C2—H2C0.9600C17—H170.9300
C2—H2D0.9600C18—H180.9300
C3—C41.480 (4)C19—H19A0.9600
C4—C91.382 (4)C19—H19B0.9600
C4—C51.405 (4)C19—H19C0.9600
C5—C61.387 (4)C20—H20A0.9600
C6—C71.363 (5)C20—H20B0.9600
C6—H60.9300C20—H20C0.9600
C1—N1—N2116.4 (3)C11—C10—H10A109.5
C1—N1—H1121.8C11—C10—H10B109.5
N2—N1—H1121.8H10A—C10—H10B109.5
C3—N2—N1120.0 (3)C11—C10—H10C109.5
N4—N3—C1116.7 (3)H10A—C10—H10C109.5
N4—N3—H3121.6H10B—C10—H10C109.5
C1—N3—H3121.6N4—C11—C12115.4 (3)
C11—N4—N3120.2 (3)N4—C11—C10122.7 (3)
C18—N5—C19120.2 (3)C12—C11—C10121.8 (3)
C18—N5—C20121.3 (3)C17—C12—C13116.4 (3)
C19—N5—C20118.5 (3)C17—C12—C11121.2 (3)
C5—O2—H2A109.5C13—C12—C11122.4 (3)
C13—O3—H3A109.5O3—C13—C14117.2 (3)
O1—C1—N1124.8 (3)O3—C13—C12122.7 (3)
O1—C1—N3123.5 (3)C14—C13—C12120.1 (3)
N1—C1—N3111.6 (3)C15—C14—C13121.2 (4)
C3—C2—H2B109.5C15—C14—H14119.4
C3—C2—H2C109.5C13—C14—H14119.4
H2B—C2—H2C109.5C14—C15—C16119.7 (4)
C3—C2—H2D109.5C14—C15—CG159.7 (2)
H2B—C2—H2D109.5C14—C15—H15120.2
H2C—C2—H2D109.5C16—C15—H15120.2
N2—C3—C4115.1 (3)C15—C16—C17120.0 (4)
N2—C3—C2123.6 (3)C15—C16—H16120.0
C4—C3—C2121.3 (3)C17—C16—H16120.0
C9—C4—C5116.9 (3)C16—C17—C12122.5 (4)
C9—C4—C3120.9 (3)C16—C17—H17118.8
C5—C4—C3122.2 (3)C12—C17—H17118.8
O2—C5—C6116.4 (3)O4—C18—N5125.4 (4)
O2—C5—C4123.3 (3)O4—C18—H18117.3
C6—C5—C4120.3 (3)N5—C18—H18117.3
C7—C6—C5121.0 (3)N5—C19—H19A109.5
C7—C6—H6119.5N5—C19—H19B109.5
C5—C6—H6119.5H19A—C19—H19B109.5
C6—C7—C8119.6 (3)N5—C19—H19C109.5
C6—C7—H7120.2H19A—C19—H19C109.5
C8—C7—H7120.2H19B—C19—H19C109.5
C7—C8—C9120.0 (4)N5—C20—H20A109.5
C7—C8—H8120.0N5—C20—H20B109.5
C9—C8—H8120.0H20A—C20—H20B109.5
C8—C9—C4122.2 (3)N5—C20—H20C109.5
C8—C9—H9118.9H20A—C20—H20C109.5
C4—C9—H9118.9H20B—C20—H20C109.5

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C12–C17 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1···O40.862.022.805 (3)151
N3—H3···O40.862.092.858 (4)148
O2—H2A···N20.821.832.548 (3)145
O3—H3A···N40.821.832.546 (3)145
C6—H6···O1i0.932.573.241 (4)129
C10—H10A···Cgii0.962.663.536 (4)153

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2762).

References

  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Li, M. X., Cai, P., Duan, C. Y., Lu, F., Xie, J. & Meng, Q. J. (2004). Inorg. Chem.43, 5174–5176. [PubMed]
  • Loncle, C., Brunel, J. M., Vidal, N., Dherbomez, M. & Letourneux, Y. (2004). Eur. J. Med. Chem.39, 1067–1071. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zukerman-Schpector, J., Affan, M. A., Foo, S. W. & Tiekink, E. R. T. (2009). Acta Cryst. E65, o2951. [PMC free article] [PubMed]

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