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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o169.
Published online 2008 December 20. doi:  10.1107/S160053680804258X
PMCID: PMC2968080

N′-[(5-Chloro-1H-indol-3-yl)methyl­ene]-3,4,5-trihydroxy­benzohydrazide

Abstract

The two aromatic parts of the title compound, C16H13ClN3O4, are connected through a conjugated –CH=N–NH–C(O)– fragment, giving an almost planar mol­ecule (r.m.s. deviation 0.08 Å). In the crystal structure, adjacent mol­ecules are linked by N—H(...)O and O—H(...)O hydrogen bonds into a three-dimensional network.

Related literature

For the isostructural C16H13BrN3O4 analog, see: Khaledi et al. (2008 [triangle]).

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Object name is e-65-0o169-scheme1.jpg

Experimental

Crystal data

  • C16H12ClN3O4
  • M r = 345.74
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o169-efi1.jpg
  • a = 9.6481 (2) Å
  • b = 15.1408 (3) Å
  • c = 10.2206 (2) Å
  • β = 98.232 (1)°
  • V = 1477.64 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.29 mm−1
  • T = 100 (2) K
  • 0.32 × 0.22 × 0.12 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.914, T max = 0.966
  • 10185 measured reflections
  • 3389 independent reflections
  • 2907 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.093
  • S = 1.06
  • 3389 reflections
  • 220 parameters
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.33 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, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680804258X/xu2471sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680804258X/xu2471Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for funding this study (Science Fund grants 12–02-03–2031, 12–02-03–2051).

supplementary crystallographic information

Experimental

5-Chloroindole-3-carbaldehyde (0.27 g, 1.5 mmol) and 3,4,5-trihydroxybenzoylhydrazine (0.27 g, 1.5 mmol) were heated in ethanol (20 ml) for 3 h. About 1 ml of acetic acid also added. The solid that separated out was collected, washed with water and then recrystallized from DMSO.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.95, N–H 0.88, O–H 0.84 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times Ueq(C,N,O). The hydroxy groups were rotated to fit the electron density.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C16H12ClN3O4 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C16H12ClN3O4F(000) = 712
Mr = 345.74Dx = 1.554 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4113 reflections
a = 9.6481 (2) Åθ = 2.4–28.2°
b = 15.1408 (3) ŵ = 0.29 mm1
c = 10.2206 (2) ÅT = 100 K
β = 98.232 (1)°Prism, orange
V = 1477.64 (5) Å30.32 × 0.22 × 0.12 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer3389 independent reflections
Radiation source: fine-focus sealed tube2907 reflections with I > 2σ(I)
graphiteRint = 0.025
ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→12
Tmin = 0.914, Tmax = 0.966k = −19→19
10185 measured reflectionsl = −13→13

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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0452P)2 + 0.6635P] where P = (Fo2 + 2Fc2)/3
3389 reflections(Δ/σ)max = 0.001
220 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = −0.33 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl10.99034 (4)1.07558 (3)0.24671 (4)0.02606 (12)
O10.68592 (10)0.82901 (7)0.56884 (10)0.0165 (2)
O20.64086 (10)0.62519 (7)0.94667 (10)0.0172 (2)
H2O0.59620.59610.99680.026*
O30.36728 (11)0.59550 (6)0.94304 (9)0.0140 (2)
H3O0.30470.61950.98010.021*
O40.16964 (10)0.67781 (7)0.73963 (10)0.0149 (2)
H4O0.15210.64140.79710.022*
N10.46397 (12)0.86816 (8)0.48430 (11)0.0138 (2)
H1N0.37400.86380.48950.017*
N20.51003 (13)0.92205 (7)0.38882 (11)0.0137 (2)
N30.39990 (13)1.10793 (8)0.03144 (12)0.0162 (3)
H3N0.35441.1361−0.03690.019*
C10.50119 (15)0.76183 (9)0.66318 (13)0.0130 (3)
C20.59758 (15)0.72084 (9)0.75913 (13)0.0141 (3)
H20.69520.73050.76160.017*
C30.54846 (15)0.66576 (9)0.85061 (13)0.0131 (3)
C40.40551 (15)0.65121 (9)0.84928 (13)0.0123 (3)
C50.31087 (14)0.69082 (9)0.75114 (13)0.0125 (3)
C60.35827 (15)0.74599 (9)0.65851 (13)0.0133 (3)
H60.29320.77300.59190.016*
C70.55811 (15)0.82260 (9)0.56894 (13)0.0131 (3)
C80.41317 (15)0.96681 (9)0.31823 (13)0.0142 (3)
H80.31950.96150.33580.017*
C90.44207 (15)1.02444 (9)0.21398 (13)0.0142 (3)
C100.33977 (16)1.05950 (9)0.11972 (14)0.0162 (3)
H100.24191.05090.11720.019*
C110.57451 (15)1.05429 (9)0.18016 (13)0.0133 (3)
C120.71420 (15)1.04422 (9)0.23767 (13)0.0147 (3)
H120.73861.01090.31640.018*
C130.81494 (16)1.08455 (10)0.17549 (14)0.0169 (3)
C140.78385 (16)1.13505 (10)0.06023 (14)0.0187 (3)
H140.85741.16090.02060.022*
C150.64682 (16)1.14724 (9)0.00445 (14)0.0172 (3)
H150.62351.1823−0.07270.021*
C160.54321 (16)1.10616 (9)0.06539 (13)0.0146 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.01421 (19)0.0351 (2)0.0286 (2)−0.00330 (15)0.00218 (15)0.00450 (16)
O10.0125 (5)0.0194 (5)0.0187 (5)−0.0004 (4)0.0054 (4)0.0023 (4)
O20.0113 (5)0.0246 (6)0.0156 (5)0.0001 (4)0.0013 (4)0.0057 (4)
O30.0132 (5)0.0167 (5)0.0131 (5)0.0012 (4)0.0055 (4)0.0018 (4)
O40.0101 (5)0.0191 (5)0.0155 (5)−0.0022 (4)0.0017 (4)0.0035 (4)
N10.0124 (6)0.0149 (6)0.0152 (6)−0.0011 (5)0.0059 (4)0.0021 (4)
N20.0159 (6)0.0135 (6)0.0129 (5)−0.0014 (5)0.0060 (4)−0.0005 (4)
N30.0185 (6)0.0160 (6)0.0135 (5)0.0028 (5)0.0003 (5)0.0009 (4)
C10.0145 (7)0.0119 (6)0.0134 (6)−0.0007 (5)0.0050 (5)−0.0029 (5)
C20.0110 (7)0.0166 (7)0.0154 (6)−0.0016 (5)0.0039 (5)−0.0022 (5)
C30.0122 (7)0.0143 (6)0.0125 (6)0.0024 (5)0.0009 (5)−0.0020 (5)
C40.0140 (7)0.0126 (6)0.0110 (6)−0.0013 (5)0.0038 (5)−0.0024 (5)
C50.0109 (6)0.0137 (6)0.0135 (6)−0.0009 (5)0.0034 (5)−0.0038 (5)
C60.0134 (7)0.0137 (6)0.0125 (6)0.0010 (5)0.0014 (5)−0.0007 (5)
C70.0151 (7)0.0121 (6)0.0131 (6)−0.0004 (5)0.0049 (5)−0.0040 (5)
C80.0132 (7)0.0149 (6)0.0153 (6)−0.0012 (5)0.0046 (5)−0.0039 (5)
C90.0153 (7)0.0136 (6)0.0139 (6)0.0004 (5)0.0029 (5)−0.0029 (5)
C100.0164 (7)0.0155 (7)0.0167 (7)0.0003 (6)0.0020 (5)−0.0032 (5)
C110.0173 (7)0.0102 (6)0.0130 (6)−0.0005 (5)0.0041 (5)−0.0028 (5)
C120.0167 (7)0.0134 (7)0.0139 (6)−0.0003 (5)0.0024 (5)−0.0005 (5)
C130.0143 (7)0.0173 (7)0.0193 (7)−0.0007 (6)0.0024 (6)−0.0022 (5)
C140.0224 (8)0.0159 (7)0.0192 (7)−0.0037 (6)0.0082 (6)−0.0005 (5)
C150.0255 (8)0.0133 (6)0.0137 (6)−0.0004 (6)0.0058 (6)−0.0002 (5)
C160.0191 (7)0.0122 (6)0.0125 (6)0.0003 (5)0.0022 (5)−0.0028 (5)

Geometric parameters (Å, °)

Cl1—C131.7491 (15)C2—H20.9500
O1—C71.2371 (17)C3—C41.3948 (19)
O2—C31.3731 (16)C4—C51.3919 (19)
O2—H2O0.8400C5—C61.3883 (19)
O3—C41.3664 (16)C6—H60.9500
O3—H3O0.8400C8—C91.4350 (19)
O4—C51.3650 (16)C8—H80.9500
O4—H4O0.8400C9—C101.383 (2)
N1—C71.3506 (18)C9—C111.443 (2)
N1—N21.3927 (16)C10—H100.9500
N1—H1N0.8800C11—C121.399 (2)
N2—C81.2884 (19)C11—C161.4080 (19)
N3—C101.3558 (19)C12—C131.378 (2)
N3—C161.3768 (19)C12—H120.9500
N3—H3N0.8800C13—C141.400 (2)
C1—C61.3936 (19)C14—C151.375 (2)
C1—C21.397 (2)C14—H140.9500
C1—C71.4925 (19)C15—C161.397 (2)
C2—C31.3860 (19)C15—H150.9500
C3—O2—H2O109.5O1—C7—C1120.52 (13)
C4—O3—H3O109.5N1—C7—C1116.90 (12)
C5—O4—H4O109.5N2—C8—C9122.22 (13)
C7—N1—N2119.69 (12)N2—C8—H8118.9
C7—N1—H1N120.2C9—C8—H8118.9
N2—N1—H1N120.2C10—C9—C8123.75 (14)
C8—N2—N1114.96 (12)C10—C9—C11106.32 (12)
C10—N3—C16109.38 (12)C8—C9—C11129.87 (13)
C10—N3—H3N125.3N3—C10—C9109.91 (13)
C16—N3—H3N125.3N3—C10—H10125.0
C6—C1—C2120.24 (13)C9—C10—H10125.0
C6—C1—C7122.53 (13)C12—C11—C16119.31 (13)
C2—C1—C7117.23 (13)C12—C11—C9134.24 (13)
C3—C2—C1118.90 (13)C16—C11—C9106.41 (13)
C3—C2—H2120.5C13—C12—C11117.29 (13)
C1—C2—H2120.5C13—C12—H12121.4
O2—C3—C2120.11 (12)C11—C12—H12121.4
O2—C3—C4118.44 (12)C12—C13—C14123.35 (14)
C2—C3—C4121.44 (13)C12—C13—Cl1118.55 (11)
O3—C4—C5123.80 (13)C14—C13—Cl1118.07 (11)
O3—C4—C3117.16 (12)C15—C14—C13119.96 (14)
C5—C4—C3118.99 (12)C15—C14—H14120.0
O4—C5—C6116.76 (12)C13—C14—H14120.0
O4—C5—C4122.94 (12)C14—C15—C16117.53 (13)
C6—C5—C4120.30 (13)C14—C15—H15121.2
C5—C6—C1120.07 (13)C16—C15—H15121.2
C5—C6—H6120.0N3—C16—C15129.48 (13)
C1—C6—H6120.0N3—C16—C11107.98 (12)
O1—C7—N1122.58 (13)C15—C16—C11122.54 (14)
C7—N1—N2—C8−175.96 (12)N2—C8—C9—C10166.52 (13)
C6—C1—C2—C3−1.2 (2)N2—C8—C9—C11−10.3 (2)
C7—C1—C2—C3178.31 (12)C16—N3—C10—C9−0.12 (16)
C1—C2—C3—O2−179.47 (12)C8—C9—C10—N3−177.25 (12)
C1—C2—C3—C4−0.5 (2)C11—C9—C10—N30.18 (15)
O2—C3—C4—O3−1.36 (18)C10—C9—C11—C12177.59 (15)
C2—C3—C4—O3179.69 (12)C8—C9—C11—C12−5.2 (3)
O2—C3—C4—C5−178.98 (12)C10—C9—C11—C16−0.17 (15)
C2—C3—C4—C52.1 (2)C8—C9—C11—C16177.04 (14)
O3—C4—C5—O40.2 (2)C16—C11—C12—C13−1.65 (19)
C3—C4—C5—O4177.70 (12)C9—C11—C12—C13−179.19 (14)
O3—C4—C5—C6−179.32 (12)C11—C12—C13—C140.7 (2)
C3—C4—C5—C6−1.9 (2)C11—C12—C13—Cl1178.50 (10)
O4—C5—C6—C1−179.44 (12)C12—C13—C14—C150.8 (2)
C4—C5—C6—C10.2 (2)Cl1—C13—C14—C15−176.97 (11)
C2—C1—C6—C51.4 (2)C13—C14—C15—C16−1.3 (2)
C7—C1—C6—C5−178.09 (12)C10—N3—C16—C15−179.12 (14)
N2—N1—C7—O12.73 (19)C10—N3—C16—C110.00 (15)
N2—N1—C7—C1−176.29 (11)C14—C15—C16—N3179.40 (14)
C6—C1—C7—O1−173.65 (13)C14—C15—C16—C110.4 (2)
C2—C1—C7—O16.83 (19)C12—C11—C16—N3−178.05 (12)
C6—C1—C7—N15.39 (19)C9—C11—C16—N30.11 (15)
C2—C1—C7—N1−174.13 (12)C12—C11—C16—C151.1 (2)
N1—N2—C8—C9−178.92 (12)C9—C11—C16—C15179.30 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2o···O30.842.202.6726 (14)116
O3—H3o···O1i0.841.742.5818 (14)175
O4—H4o···N2i0.842.012.7668 (15)149
N1—H1n···O2ii0.882.233.0875 (16)163
N3—H3n···O4iii0.882.152.9518 (15)152

Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) −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: XU2471).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008). Acta Cryst. E64, o2108. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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