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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2357.
Published online 2008 November 13. doi:  10.1107/S1600536808035757
PMCID: PMC2960057

N 2-[1-(2-Hydroxy­phen­yl)ethyl­idene]-N 2′-(1H-indol-3-ylmethyl­ene)carbonic dihydrazide

Abstract

In the crystal structure of the title compound {alternative name: 1-[1-(2-hydroxy­phen­yl)ethyl­ideneamino]-3-(1H-indol-3-ylmethyl­eneamino)urea}, C18H17N5O2, the planar indole component is twisted at an angle of 63.7 (10)° with respect to the rest of the mol­ecule. This compound is one of a series being studied for biological activity. The hydr­oxy groups are involved in both intra­molecular (O—H(...)N) and inter­molecular (N—H(...)O) hydrogen bonds.

Related literature

For a related compound, see: Dan et al. (1987 [triangle]).

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Object name is e-64-o2357-scheme1.jpg

Experimental

Crystal data

  • C18H17N5O2
  • M r = 335.37
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2357-efi1.jpg
  • a = 7.0802 (8) Å
  • b = 9.5335 (11) Å
  • c = 25.110 (3) Å
  • β = 97.295 (2)°
  • V = 1681.2 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 (2) K
  • 0.42 × 0.42 × 0.16 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.821, T max = 0.986
  • 11912 measured reflections
  • 4740 independent reflections
  • 4145 reflections with I > 2σ(I)
  • R int = 0.014

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.122
  • S = 1.03
  • 4740 reflections
  • 228 parameters
  • H-atom parameters constrained
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.32 e Å−3

Data collection: APEX2 (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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035757/hg2434sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035757/hg2434Isup2.hkl

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

Acknowledgments

The authors thank the University of Malaya for funding this study (Science Fund Grants 12–02-03–2031, 12–02-03–2051 and PJP FS350–2008 A).

supplementary crystallographic information

Comment

X-ray structures, of Schiff bases derived from condensation of indole-3-carboxaldehyde and 2-hydroxyacetophenone, have not been investigated. The title compound (Fig. 1) appears to be the first example with the planar indole component is twisted at an angle of 116.3 (10)° with respect to the rest of the molecule. However, compound bis(salicylidene)carbonohydrazide (Dan et al.1987), which was reported previously shows planarity for the whole molecule.

Experimental

Indole-3-carboxaldehyde (0.30 g, 2.07 mmol), carbohydrazide (0.187 g, 2.07 mmol), and 2-Hydroxyacetophenone (0.24 ml, 2.07 mmol) were heated in acidified ethanol (20 ml) for 2 h. The solvent was removed and the product recrystallized from DMSO.

Refinement

Hydrogen atoms were placed at calculated positions (C—H 0.95, N—H 0.88 and O—H 0.84 Å), with U(H) set to 1.2–1.5 times Ueq(C,N,O).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C18H17N5O2 at 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius

Crystal data

C18H17N5O2F000 = 704
Mr = 335.37Dx = 1.325 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6889 reflections
a = 7.0802 (8) Åθ = 2.3–30.5º
b = 9.5335 (11) ŵ = 0.09 mm1
c = 25.110 (3) ÅT = 100 (2) K
β = 97.295 (2)ºIrregular, colourless
V = 1681.2 (3) Å30.42 × 0.42 × 0.16 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer4740 independent reflections
Radiation source: fine-focus sealed tube4145 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.014
T = 100(2) Kθmax = 30.6º
ω scansθmin = 2.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −10→4
Tmin = 0.821, Tmax = 0.986k = −13→12
11912 measured reflectionsl = −34→35

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.122  w = 1/[σ2(Fo2) + (0.0656P)2 + 0.7125P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4740 reflectionsΔρmax = 0.43 e Å3
228 parametersΔρmin = −0.32 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
N20.47231 (13)0.13948 (10)0.11232 (3)0.01593 (18)
O20.38944 (12)0.16315 (8)−0.02799 (3)0.01958 (18)
O10.22435 (14)0.47449 (9)−0.09575 (3)0.0246 (2)
H1A0.25980.4252−0.06860.037*
N50.28865 (13)0.41919 (9)0.00270 (3)0.01540 (18)
N30.45872 (14)0.09630 (10)0.05941 (4)0.01774 (19)
H3B0.48780.00990.05130.021*
C130.17966 (15)0.64221 (11)−0.02541 (4)0.0159 (2)
N40.35380 (14)0.31965 (9)0.03933 (3)0.01631 (19)
H4B0.36630.33740.07400.020*
C110.25266 (15)0.54484 (11)0.01820 (4)0.0150 (2)
C100.39925 (15)0.19077 (11)0.02031 (4)0.0155 (2)
C90.57339 (15)0.06194 (11)0.14689 (4)0.0160 (2)
H90.6346−0.01930.13540.019*
C80.59385 (15)0.09842 (11)0.20307 (4)0.0153 (2)
N10.69458 (15)0.09189 (10)0.29159 (4)0.0203 (2)
H1B0.75900.06760.32250.024*
C120.28004 (18)0.59167 (13)0.07571 (5)0.0224 (2)
H12A0.15930.58330.09070.034*
H12B0.32230.68960.07770.034*
H12C0.37640.53260.09630.034*
C140.16631 (16)0.60243 (11)−0.07989 (4)0.0180 (2)
C150.09241 (18)0.69504 (13)−0.12025 (5)0.0237 (2)
H150.08130.6664−0.15680.028*
C70.71448 (17)0.03294 (12)0.24298 (4)0.0192 (2)
H70.7986−0.04180.23750.023*
C50.49227 (15)0.20425 (11)0.22913 (4)0.0147 (2)
C180.12097 (18)0.77799 (12)−0.01393 (5)0.0240 (2)
H180.12940.80760.02240.029*
C30.48431 (17)0.27906 (12)0.32274 (5)0.0208 (2)
H30.53030.27210.35990.025*
C10.27606 (18)0.38481 (13)0.24917 (5)0.0255 (3)
H10.17910.45090.23760.031*
C40.55764 (16)0.19532 (11)0.28456 (4)0.0164 (2)
C20.34160 (18)0.37266 (13)0.30407 (5)0.0247 (2)
H20.28680.42990.32900.030*
C170.05073 (19)0.87046 (13)−0.05440 (6)0.0283 (3)
H170.01340.9625−0.04570.034*
C60.35025 (16)0.30202 (12)0.21144 (5)0.0200 (2)
H60.30560.31140.17430.024*
C160.03524 (18)0.82812 (13)−0.10749 (5)0.0264 (3)
H16−0.01480.8907−0.13520.032*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N20.0201 (4)0.0163 (4)0.0114 (4)0.0015 (3)0.0021 (3)−0.0005 (3)
O20.0286 (4)0.0170 (4)0.0127 (3)0.0047 (3)0.0009 (3)−0.0006 (3)
O10.0389 (5)0.0196 (4)0.0140 (4)0.0084 (4)−0.0020 (3)−0.0002 (3)
N50.0172 (4)0.0140 (4)0.0148 (4)0.0021 (3)0.0012 (3)0.0020 (3)
N30.0264 (5)0.0145 (4)0.0121 (4)0.0054 (3)0.0016 (3)−0.0001 (3)
C130.0141 (4)0.0142 (4)0.0192 (5)0.0006 (4)0.0015 (4)0.0011 (4)
N40.0228 (5)0.0140 (4)0.0118 (4)0.0046 (3)0.0008 (3)0.0009 (3)
C110.0144 (4)0.0146 (4)0.0162 (4)0.0004 (4)0.0027 (3)−0.0004 (4)
C100.0175 (5)0.0144 (4)0.0143 (4)0.0017 (4)0.0013 (4)0.0002 (3)
C90.0180 (5)0.0149 (4)0.0153 (4)0.0021 (4)0.0033 (4)0.0004 (4)
C80.0172 (5)0.0148 (4)0.0139 (4)0.0013 (4)0.0024 (4)0.0012 (3)
N10.0262 (5)0.0209 (5)0.0128 (4)0.0031 (4)−0.0008 (3)0.0018 (3)
C120.0300 (6)0.0201 (5)0.0173 (5)0.0019 (4)0.0036 (4)−0.0036 (4)
C140.0173 (5)0.0162 (5)0.0197 (5)0.0010 (4)−0.0007 (4)0.0018 (4)
C150.0235 (6)0.0242 (6)0.0221 (5)0.0013 (4)−0.0028 (4)0.0061 (4)
C70.0232 (5)0.0187 (5)0.0157 (5)0.0044 (4)0.0016 (4)0.0015 (4)
C50.0161 (5)0.0138 (4)0.0143 (4)−0.0022 (4)0.0027 (3)−0.0007 (3)
C180.0265 (6)0.0172 (5)0.0281 (6)0.0045 (4)0.0033 (5)−0.0003 (4)
C30.0244 (6)0.0212 (5)0.0176 (5)−0.0058 (4)0.0052 (4)−0.0048 (4)
C10.0210 (6)0.0239 (6)0.0310 (6)0.0058 (4)0.0013 (5)−0.0083 (5)
C40.0188 (5)0.0151 (5)0.0156 (5)−0.0030 (4)0.0030 (4)−0.0003 (4)
C20.0240 (6)0.0244 (6)0.0269 (6)−0.0022 (5)0.0076 (5)−0.0108 (5)
C170.0284 (6)0.0161 (5)0.0402 (7)0.0068 (4)0.0034 (5)0.0046 (5)
C60.0189 (5)0.0199 (5)0.0208 (5)0.0031 (4)0.0002 (4)−0.0029 (4)
C160.0219 (6)0.0218 (6)0.0343 (6)0.0021 (4)−0.0013 (5)0.0116 (5)

Geometric parameters (Å, °)

N2—C91.2862 (14)C12—H12A0.9800
N2—N31.3824 (12)C12—H12B0.9800
O2—C101.2344 (13)C12—H12C0.9800
O1—C141.3626 (13)C14—C151.3949 (15)
O1—H1A0.8400C15—C161.3816 (18)
N5—C111.2948 (13)C15—H150.9500
N5—N41.3608 (12)C7—H70.9500
N3—C101.3591 (13)C5—C61.4013 (15)
N3—H3B0.8800C5—C41.4125 (14)
C13—C181.4007 (15)C18—C171.3887 (17)
C13—C141.4111 (15)C18—H180.9500
C13—C111.4779 (14)C3—C21.3844 (18)
N4—C101.3712 (13)C3—C41.3973 (15)
N4—H4B0.8800C3—H30.9500
C11—C121.5003 (15)C1—C61.3866 (16)
C9—C81.4424 (14)C1—C21.4024 (18)
C9—H90.9500C1—H10.9500
C8—C71.3807 (14)C2—H20.9500
C8—C51.4431 (14)C17—C161.384 (2)
N1—C71.3672 (14)C17—H170.9500
N1—C41.3784 (14)C6—H60.9500
N1—H1B0.8800C16—H160.9500
C9—N2—N3116.25 (9)C15—C14—C13120.46 (10)
C14—O1—H1A109.5C16—C15—C14120.45 (11)
C11—N5—N4120.31 (9)C16—C15—H15119.8
C10—N3—N2118.31 (9)C14—C15—H15119.8
C10—N3—H3B120.8N1—C7—C8109.75 (10)
N2—N3—H3B120.8N1—C7—H7125.1
C18—C13—C14117.56 (10)C8—C7—H7125.1
C18—C13—C11120.87 (10)C6—C5—C4118.98 (10)
C14—C13—C11121.57 (9)C6—C5—C8134.45 (10)
N5—N4—C10117.64 (9)C4—C5—C8106.55 (9)
N5—N4—H4B121.2C17—C18—C13121.61 (12)
C10—N4—H4B121.2C17—C18—H18119.2
N5—C11—C13114.95 (9)C13—C18—H18119.2
N5—C11—C12123.94 (10)C2—C3—C4117.05 (10)
C13—C11—C12121.10 (9)C2—C3—H3121.5
O2—C10—N3122.82 (10)C4—C3—H3121.5
O2—C10—N4123.15 (9)C6—C1—C2121.18 (11)
N3—C10—N4114.02 (9)C6—C1—H1119.4
N2—C9—C8119.98 (10)C2—C1—H1119.4
N2—C9—H9120.0N1—C4—C3129.59 (10)
C8—C9—H9120.0N1—C4—C5107.85 (9)
C7—C8—C9125.24 (10)C3—C4—C5122.54 (10)
C7—C8—C5106.56 (9)C3—C2—C1121.48 (11)
C9—C8—C5128.18 (9)C3—C2—H2119.3
C7—N1—C4109.28 (9)C1—C2—H2119.3
C7—N1—H1B125.4C16—C17—C18119.80 (11)
C4—N1—H1B125.4C16—C17—H17120.1
C11—C12—H12A109.5C18—C17—H17120.1
C11—C12—H12B109.5C1—C6—C5118.75 (11)
H12A—C12—H12B109.5C1—C6—H6120.6
C11—C12—H12C109.5C5—C6—H6120.6
H12A—C12—H12C109.5C15—C16—C17120.09 (11)
H12B—C12—H12C109.5C15—C16—H16120.0
O1—C14—C15116.97 (10)C17—C16—H16120.0
O1—C14—C13122.57 (9)
C9—N2—N3—C10−162.57 (10)C5—C8—C7—N1−0.35 (13)
C11—N5—N4—C10−176.52 (10)C7—C8—C5—C6−178.47 (12)
N4—N5—C11—C13−179.00 (9)C9—C8—C5—C6−0.3 (2)
N4—N5—C11—C120.64 (16)C7—C8—C5—C4−0.58 (12)
C18—C13—C11—N5174.99 (10)C9—C8—C5—C4177.62 (10)
C14—C13—C11—N5−5.00 (15)C14—C13—C18—C170.46 (18)
C18—C13—C11—C12−4.66 (16)C11—C13—C18—C17−179.52 (11)
C14—C13—C11—C12175.35 (10)C7—N1—C4—C3177.00 (11)
N2—N3—C10—O2177.29 (10)C7—N1—C4—C5−1.54 (13)
N2—N3—C10—N4−1.86 (15)C2—C3—C4—N1−178.03 (11)
N5—N4—C10—O22.37 (16)C2—C3—C4—C50.33 (17)
N5—N4—C10—N3−178.48 (9)C6—C5—C4—N1179.57 (10)
N3—N2—C9—C8−179.42 (9)C8—C5—C4—N11.29 (12)
N2—C9—C8—C7−172.45 (11)C6—C5—C4—C30.90 (16)
N2—C9—C8—C59.66 (17)C8—C5—C4—C3−177.38 (10)
C18—C13—C14—O1178.09 (11)C4—C3—C2—C1−1.19 (18)
C11—C13—C14—O1−1.93 (17)C6—C1—C2—C30.8 (2)
C18—C13—C14—C15−1.62 (16)C13—C18—C17—C160.9 (2)
C11—C13—C14—C15178.37 (10)C2—C1—C6—C50.44 (18)
O1—C14—C15—C16−178.26 (11)C4—C5—C6—C1−1.26 (16)
C13—C14—C15—C161.46 (18)C8—C5—C6—C1176.42 (12)
C4—N1—C7—C81.19 (13)C14—C15—C16—C17−0.10 (19)
C9—C8—C7—N1−178.62 (10)C18—C17—C16—C15−1.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1A···N50.841.782.5121 (11)145
N3—H3B···O2i0.881.992.8481 (13)166
N1—H1B···O1ii0.882.142.8803 (13)142

Symmetry codes: (i) −x+1, −y, −z; (ii) 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: HG2434).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dan, J., Seth, S. & Chakraborty, S. (1987). Acta Cryst. C43, 1114–1116.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2008). publCIF. In preparation.

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