PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2968.
Published online 2010 October 30. doi:  10.1107/S1600536810043151
PMCID: PMC3009339

1,5-Bis[1-(2,4-dihy­droxy­phen­yl)ethyl­idene]carbonohydrazide dimethyl­formamide disolvate

Abstract

In the title compound, C17H18N4O5·2C3H7NO, two solvent mol­ecules are linked to the main mol­ecule via N—H(...)O and O—H(...)O hydrogen bonds, forming a hydrogen-bonded trimer. Intra­molecular O—H(...)N hydrogen bonds influence the mol­ecular conformation of the main mol­ecule, and the two benzene rings form a dihedral angle of 10.55 (18)°. In the crystal, inter­molecular O—H(...)O hydrogen bonds link hydrogen-bonded trimers into ribbons extending along the b axis.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-66-o2968-scheme1.jpg

Experimental

Crystal data

  • C17H18N4O5·2C3H7NO
  • M r = 504.55
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2968-efi1.jpg
  • a = 11.3506 (11) Å
  • b = 9.0160 (7) Å
  • c = 24.953 (3) Å
  • β = 97.546 (1)°
  • V = 2531.5 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 K
  • 0.50 × 0.37 × 0.35 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.952, T max = 0.966
  • 12361 measured reflections
  • 4466 independent reflections
  • 2158 reflections with I > 2σ(I)
  • R int = 0.055

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.152
  • S = 1.03
  • 4466 reflections
  • 331 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.27 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/S1600536810043151/cv2779sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043151/cv2779Isup2.hkl

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

Acknowledgments

This project was supported by the University Student Science and Technology Culture Foundation of Liaocheng University (grant No. SRT10056HX2) and the Foundation of Liaocheng University (grant No. X09010).

supplementary crystallographic information

Comment

Carbonohydrazide Schiff base derivatives are known to exhibit a wide range of interesting biological activities, including antibacterial antifungal, anticonvulsant, anticancer activities as well as herbicidal and fungicidal activity (Loncle et al., 2004; Li et al., 2004). Herewith we present the crystal structure of the title compound (I) - a new carbonohydrazide derivative.

In (I) (Fig. 1), the bond lengths and angles of the main molecule 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 intramolecular O—H···N hydrogen bonds (Table 1) influence the molecular conformation. Two DMF solvent molecules are linked to the main molecule via N—H···O and O—H···O hydrogen bonds (Table 1) forming a hydrogen-bonded trimer (Fig. 1). Intermolecular O—H···O hydrogen bonds (Table 1) link hydrogen-bonded trimers into ribbons extended along the b axis.

Experimental

2, 4-Dihydroxylacetophenone (10.0 mmol) and carbohydrazide (5.0 mmol) were mixed in 50 ml flash. After 3h stirring at 373 K, the resulting mixture was cooled to room temperature, and recrystalized from DMF, and afforded the title compound as a crystalline solid.

Refinement

All H atoms were placed in idealized positions (C—H 0.93–0.96 Å, N—H 0.86 Å, O—H 0.82 Å) and constrained to ride on their parent atoms, with Uiso(H) = 1.2–1.5 Ueq(parent atom).

Figures

Fig. 1.
The content of asymmetric unit of the title compound showing the atomic numbering scheme and 30% probability displacement ellipsoids. Dashed lines denote intermolecular hydrogen bonds.

Crystal data

C17H18N4O5·2C3H7NOF(000) = 1072
Mr = 504.55Dx = 1.324 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.3506 (11) ÅCell parameters from 2127 reflections
b = 9.0160 (7) Åθ = 2.9–23.9°
c = 24.953 (3) ŵ = 0.10 mm1
β = 97.546 (1)°T = 298 K
V = 2531.5 (4) Å3Block, colourless
Z = 40.50 × 0.37 × 0.35 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer4466 independent reflections
Radiation source: fine-focus sealed tube2158 reflections with I > 2σ(I)
graphiteRint = 0.055
[var phi] and ω scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→13
Tmin = 0.952, Tmax = 0.966k = −10→10
12361 measured reflectionsl = −29→27

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0565P)2 + 0.4683P] where P = (Fo2 + 2Fc2)/3
4466 reflections(Δ/σ)max = 0.009
331 parametersΔρmax = 0.30 e Å3
1 restraintΔρmin = −0.27 e Å3

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
N30.5482 (2)1.0132 (3)0.38574 (9)0.0413 (7)
H3'0.62331.02030.39610.050*
N40.4960 (2)1.0910 (3)0.34129 (9)0.0379 (7)
N10.4829 (2)0.7684 (3)0.48746 (9)0.0362 (7)
N20.5404 (2)0.8673 (3)0.45843 (9)0.0375 (7)
H2'0.61310.89210.46870.045*
C10.4790 (3)0.9250 (4)0.41282 (12)0.0352 (8)
C20.5629 (3)1.1733 (4)0.31528 (12)0.0371 (8)
O10.29729 (18)0.6107 (3)0.49012 (9)0.0542 (7)
H10.34140.66800.47670.081*
O40.34283 (19)1.5034 (3)0.13770 (9)0.0537 (7)
H40.27431.47580.12860.081*
C40.5033 (3)1.2567 (4)0.26924 (11)0.0346 (8)
C120.4686 (3)0.6037 (3)0.55900 (11)0.0348 (8)
O50.37418 (19)0.8984 (3)0.39800 (9)0.0519 (7)
C100.5368 (3)0.7104 (3)0.53123 (12)0.0353 (8)
C70.3926 (3)1.4211 (4)0.18086 (12)0.0405 (8)
C60.3283 (3)1.3208 (4)0.20663 (12)0.0406 (8)
H140.24801.30680.19460.049*
O30.31113 (19)1.1458 (3)0.27370 (9)0.0607 (7)
H30.35051.10270.29890.091*
C140.2910 (3)0.4568 (4)0.56516 (13)0.0465 (9)
H160.21400.43070.55090.056*
C130.3532 (3)0.5593 (4)0.53799 (12)0.0391 (8)
C90.5651 (3)1.3599 (4)0.24144 (13)0.0476 (9)
H180.64571.37380.25260.057*
C50.3820 (3)1.2408 (4)0.25034 (12)0.0378 (8)
C170.5158 (3)0.5373 (4)0.60781 (13)0.0472 (9)
H200.59230.56340.62280.057*
C150.3419 (3)0.3934 (4)0.61297 (14)0.0460 (9)
C160.4555 (3)0.4360 (4)0.63457 (13)0.0500 (9)
H220.49060.39580.66710.060*
O20.2771 (2)0.2926 (3)0.63652 (10)0.0647 (7)
H20.31370.26670.66550.097*
C80.5119 (3)1.4409 (4)0.19856 (13)0.0482 (9)
H240.55601.50900.18150.058*
C110.6630 (3)0.7461 (4)0.55445 (13)0.0512 (9)
H26A0.67540.85120.55300.077*
H26B0.71680.69640.53380.077*
H26C0.67710.71330.59130.077*
C30.6951 (3)1.1842 (4)0.33107 (14)0.0601 (11)
H32A0.71171.24730.36210.090*
H32B0.73101.22500.30160.090*
H32C0.72711.08720.33960.090*
O60.7696 (2)1.0156 (3)0.46093 (10)0.0652 (8)
C180.8226 (3)1.0859 (4)0.49864 (15)0.0531 (10)
H18A0.79161.08230.53130.064*
N50.9189 (2)1.1658 (3)0.49747 (12)0.0555 (8)
C200.9664 (4)1.1869 (5)0.44770 (17)0.0911 (15)
H20A0.92351.12620.42010.137*
H20B1.04881.15940.45230.137*
H20C0.95871.28930.43720.137*
C190.9714 (4)1.2474 (5)0.54508 (17)0.0898 (15)
H19A0.93111.22170.57530.135*
H19B0.96361.35190.53830.135*
H19C1.05401.22220.55300.135*
N60.5058 (3)0.0928 (4)0.80215 (12)0.0562 (8)
C230.4210 (3)−0.0012 (4)0.82410 (14)0.0664 (11)
H23A0.34540.00590.80190.100*
H23B0.41300.03020.86020.100*
H23C0.4482−0.10200.82470.100*
C220.4740 (4)0.1708 (5)0.75761 (18)0.0661 (11)
H22A0.53260.22780.74480.079*
C210.6253 (3)0.0985 (5)0.83068 (17)0.0882 (14)
H21A0.67260.16500.81230.132*
H21B0.65980.00110.83180.132*
H21C0.62280.13320.86690.132*
O70.3748 (2)0.1750 (3)0.73179 (11)0.0717 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N30.0364 (15)0.0483 (19)0.0378 (15)0.0007 (14)−0.0007 (12)0.0098 (14)
N40.0402 (15)0.0406 (18)0.0319 (15)0.0063 (14)0.0004 (12)0.0065 (13)
N10.0425 (16)0.0320 (17)0.0338 (15)0.0011 (13)0.0043 (13)0.0017 (13)
N20.0347 (14)0.0403 (18)0.0360 (15)−0.0025 (13)−0.0015 (12)0.0051 (13)
C10.040 (2)0.032 (2)0.0328 (18)0.0046 (16)0.0008 (16)−0.0022 (16)
C20.0377 (18)0.042 (2)0.0318 (18)−0.0001 (17)0.0061 (15)−0.0038 (16)
O10.0406 (13)0.0608 (19)0.0587 (16)−0.0030 (12)−0.0026 (12)0.0149 (13)
O40.0482 (14)0.0626 (18)0.0477 (14)0.0000 (13)−0.0038 (11)0.0189 (13)
C40.0378 (18)0.037 (2)0.0282 (17)0.0016 (16)0.0029 (14)−0.0016 (15)
C120.0416 (19)0.030 (2)0.0327 (18)0.0023 (16)0.0054 (15)−0.0018 (15)
O50.0396 (13)0.0582 (17)0.0542 (14)−0.0065 (12)−0.0077 (11)0.0107 (12)
C100.0405 (18)0.030 (2)0.0348 (18)0.0011 (16)0.0024 (15)−0.0051 (16)
C70.0394 (19)0.047 (2)0.0347 (18)0.0055 (17)0.0017 (15)0.0038 (17)
C60.0298 (17)0.048 (2)0.0434 (19)−0.0005 (17)0.0016 (15)0.0085 (18)
O30.0432 (14)0.072 (2)0.0669 (18)−0.0047 (14)0.0067 (12)0.0319 (14)
C140.042 (2)0.042 (2)0.057 (2)−0.0006 (17)0.0128 (17)0.0010 (19)
C130.0417 (19)0.036 (2)0.0395 (19)0.0052 (17)0.0044 (16)−0.0005 (16)
C90.0382 (19)0.059 (3)0.044 (2)−0.0081 (18)−0.0004 (16)0.0053 (19)
C50.0373 (19)0.041 (2)0.0373 (18)0.0001 (17)0.0119 (15)0.0050 (16)
C170.051 (2)0.045 (2)0.045 (2)−0.0019 (18)0.0012 (17)−0.0013 (18)
C150.056 (2)0.038 (2)0.049 (2)0.0041 (19)0.0249 (19)0.0009 (18)
C160.065 (2)0.047 (2)0.039 (2)0.000 (2)0.0053 (18)0.0057 (18)
O20.0669 (17)0.0618 (19)0.0703 (19)−0.0031 (15)0.0271 (13)0.0148 (15)
C80.042 (2)0.054 (3)0.047 (2)−0.0096 (18)0.0022 (16)0.0161 (19)
C110.049 (2)0.051 (2)0.050 (2)−0.0088 (18)−0.0045 (16)0.0054 (18)
C30.043 (2)0.080 (3)0.055 (2)−0.005 (2)−0.0022 (17)0.019 (2)
O60.0573 (16)0.076 (2)0.0581 (16)−0.0114 (15)−0.0095 (13)−0.0035 (15)
C180.047 (2)0.061 (3)0.051 (2)−0.001 (2)0.0053 (18)0.008 (2)
N50.0405 (17)0.061 (2)0.065 (2)−0.0069 (16)0.0060 (15)0.0056 (18)
C200.069 (3)0.113 (4)0.096 (3)−0.006 (3)0.025 (3)0.036 (3)
C190.079 (3)0.084 (4)0.099 (3)−0.032 (3)−0.016 (3)−0.016 (3)
N60.054 (2)0.055 (2)0.060 (2)−0.0052 (17)0.0098 (16)−0.0024 (18)
C230.079 (3)0.063 (3)0.061 (2)−0.005 (2)0.025 (2)0.005 (2)
C220.073 (3)0.055 (3)0.076 (3)−0.007 (2)0.033 (2)0.000 (2)
C210.072 (3)0.099 (4)0.089 (3)−0.017 (3)−0.004 (2)−0.012 (3)
O70.0652 (18)0.078 (2)0.0736 (19)0.0075 (16)0.0137 (15)0.0123 (16)

Geometric parameters (Å, °)

N3—C11.358 (4)C15—O21.352 (4)
N3—N41.379 (3)C15—C161.385 (4)
N3—H3'0.8600C16—H220.9300
N4—C21.295 (4)O2—H20.8200
N1—C101.291 (3)C8—H240.9300
N1—N21.368 (3)C11—H26A0.9600
N2—C11.358 (3)C11—H26B0.9600
N2—H2'0.8600C11—H26C0.9600
C1—O51.223 (3)C3—H32A0.9600
C2—C41.462 (4)C3—H32B0.9600
C2—C31.504 (4)C3—H32C0.9600
O1—C131.359 (3)O6—C181.225 (4)
O1—H10.8200C18—N51.312 (4)
O4—C71.367 (3)C18—H18A0.9300
O4—H40.8200N5—C201.430 (4)
C4—C91.402 (4)N5—C191.456 (4)
C4—C51.403 (4)C20—H20A0.9600
C12—C171.400 (4)C20—H20B0.9600
C12—C131.403 (4)C20—H20C0.9600
C12—C101.465 (4)C19—H19A0.9600
C10—C111.507 (4)C19—H19B0.9600
C7—C61.374 (4)C19—H19C0.9600
C7—C81.380 (4)N6—C221.325 (5)
C6—C51.381 (4)N6—C231.443 (4)
C6—H140.9300N6—C211.447 (4)
O3—C51.358 (3)C23—H23A0.9600
O3—H30.8200C23—H23B0.9600
C14—C151.380 (4)C23—H23C0.9600
C14—C131.392 (4)C22—O71.222 (4)
C14—H160.9300C22—H22A0.9300
C9—C81.369 (4)C21—H21A0.9600
C9—H180.9300C21—H21B0.9600
C17—C161.367 (4)C21—H21C0.9600
C17—H200.9300
C1—N3—N4118.9 (2)C15—O2—H2109.5
C1—N3—H3'120.6C9—C8—C7119.6 (3)
N4—N3—H3'120.6C9—C8—H24120.2
C2—N4—N3118.5 (3)C7—C8—H24120.2
C10—N1—N2120.4 (2)C10—C11—H26A109.5
C1—N2—N1117.7 (3)C10—C11—H26B109.5
C1—N2—H2'121.1H26A—C11—H26B109.5
N1—N2—H2'121.1C10—C11—H26C109.5
O5—C1—N3124.6 (3)H26A—C11—H26C109.5
O5—C1—N2123.4 (3)H26B—C11—H26C109.5
N3—C1—N2112.0 (3)C2—C3—H32A109.5
N4—C2—C4116.5 (3)C2—C3—H32B109.5
N4—C2—C3122.5 (3)H32A—C3—H32B109.5
C4—C2—C3121.0 (3)C2—C3—H32C109.5
C13—O1—H1109.5H32A—C3—H32C109.5
C7—O4—H4109.5H32B—C3—H32C109.5
C9—C4—C5115.7 (3)O6—C18—N5126.4 (4)
C9—C4—C2121.3 (3)O6—C18—H18A116.8
C5—C4—C2123.0 (3)N5—C18—H18A116.8
C17—C12—C13115.8 (3)C18—N5—C20120.1 (3)
C17—C12—C10121.8 (3)C18—N5—C19120.8 (3)
C13—C12—C10122.4 (3)C20—N5—C19118.7 (3)
N1—C10—C12116.4 (3)N5—C20—H20A109.5
N1—C10—C11124.1 (3)N5—C20—H20B109.5
C12—C10—C11119.6 (3)H20A—C20—H20B109.5
C6—C7—O4122.4 (3)N5—C20—H20C109.5
C6—C7—C8119.7 (3)H20A—C20—H20C109.5
O4—C7—C8117.9 (3)H20B—C20—H20C109.5
C7—C6—C5120.4 (3)N5—C19—H19A109.5
C7—C6—H14119.8N5—C19—H19B109.5
C5—C6—H14119.8H19A—C19—H19B109.5
C5—O3—H3109.5N5—C19—H19C109.5
C15—C14—C13121.0 (3)H19A—C19—H19C109.5
C15—C14—H16119.5H19B—C19—H19C109.5
C13—C14—H16119.5C22—N6—C23120.5 (3)
O1—C13—C14116.5 (3)C22—N6—C21121.9 (4)
O1—C13—C12122.4 (3)C23—N6—C21117.6 (3)
C14—C13—C12121.1 (3)N6—C23—H23A109.5
C8—C9—C4122.9 (3)N6—C23—H23B109.5
C8—C9—H18118.5H23A—C23—H23B109.5
C4—C9—H18118.5N6—C23—H23C109.5
O3—C5—C6116.3 (3)H23A—C23—H23C109.5
O3—C5—C4122.1 (3)H23B—C23—H23C109.5
C6—C5—C4121.6 (3)O7—C22—N6126.1 (4)
C16—C17—C12123.5 (3)O7—C22—H22A116.9
C16—C17—H20118.2N6—C22—H22A116.9
C12—C17—H20118.2N6—C21—H21A109.5
O2—C15—C14117.7 (3)N6—C21—H21B109.5
O2—C15—C16123.3 (3)H21A—C21—H21B109.5
C14—C15—C16119.0 (3)N6—C21—H21C109.5
C17—C16—C15119.7 (3)H21A—C21—H21C109.5
C17—C16—H22120.2H21B—C21—H21C109.5
C15—C16—H22120.2

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.832.549 (3)145
O3—H3···N40.821.842.562 (3)146
O2—H2···O70.821.902.704 (4)168
N2—H2'···O60.862.132.918 (3)153
N3—H3'···O60.862.162.932 (3)149
O4—H4···O5i0.821.862.680 (3)173

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2779).

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]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography