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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2481.
Published online 2008 November 29. doi:  10.1107/S1600536808039342
PMCID: PMC2959793

3,4,5-Trihydr­oxy-N′-(1H-indol-3-yl­methyl­idene)benzohydrazide penta­hydrate

Abstract

The two aromatic parts of the title compound, C16H13N3O4·5H2O, are connected through a conjugated –CH=N–NH–C(O)– fragment, giving an almost planar mol­ecule. The organic mol­ecules and uncoordinated water mol­ecules are linked by N—H(...)O and O—H(...)O hydrogen bonds into a three-dimensional network.

Related literature

For the structure of anhydrous N′-(1H-indol-3-ylmethyl­idene)-3,4,5-trihydroxy­benzohydrazide, see: Khaledi et al. (2008 [triangle]).

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Object name is e-64-o2481-scheme1.jpg

Experimental

Crystal data

  • C16H13N3O4·5H2O
  • M r = 401.37
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2481-efi1.jpg
  • a = 7.4379 (2) Å
  • b = 9.1178 (2) Å
  • c = 14.1966 (3) Å
  • α = 103.814 (1)°
  • β = 103.716 (1)°
  • γ = 90.613 (2)°
  • V = 905.95 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.12 mm−1
  • T = 100 (2) K
  • 0.30 × 0.25 × 0.04 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 7524 measured reflections
  • 4096 independent reflections
  • 3285 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.115
  • S = 1.05
  • 4096 reflections
  • 313 parameters
  • 15 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 [triangle]); 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: pubCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039342/tk2335sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039342/tk2335Isup2.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 and 12–02-03–2051).

supplementary crystallographic information

Comment

(type here to add)

Experimental

Indole-3-carbaldehyde (1.0 g, 7 mmol) and 3,4,5-trihydroxybenzoylhydrazine (1.29 g, 7 mmol) were heated in ethanol (60 ml) for 6 h. About 1 ml of acetic acid also added. The solution was set aside for the growth of crystals.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.95 Å), and were treated as riding on their parent carbon atoms, with U(H) set to 1.2Ueq(C). The nitrogen- and oxygen-bound H atoms were located in a difference Fourier map, and were refined with distance restraints of N–H 0.88±0.01 and O–H 0.84±0.01 Å.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C16H13N3O4.5H2O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C16H13N3O4·5H2OZ = 2
Mr = 401.37F000 = 424
Triclinic, P1Dx = 1.471 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 7.4379 (2) ÅCell parameters from 2461 reflections
b = 9.1178 (2) Åθ = 2.3–28.0º
c = 14.1966 (3) ŵ = 0.12 mm1
α = 103.814 (1)ºT = 100 (2) K
β = 103.716 (1)ºPlate, pale-yellow
γ = 90.613 (2)º0.30 × 0.25 × 0.04 mm
V = 905.95 (4) Å3

Data collection

Bruker SMART APEX diffractometer3285 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Monochromator: graphiteθmax = 27.5º
T = 100(2) Kθmin = 2.3º
ω scansh = −9→9
Absorption correction: Nonek = −11→11
7524 measured reflectionsl = −18→18
4096 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115  w = 1/[σ2(Fo2) + (0.0613P)2 + 0.1789P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
4096 reflectionsΔρmax = 0.35 e Å3
313 parametersΔρmin = −0.25 e Å3
15 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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

xyzUiso*/Ueq
O10.59471 (16)0.40029 (12)0.72041 (8)0.0184 (2)
O20.51512 (17)0.56940 (13)0.89648 (8)0.0217 (3)
O30.35915 (16)0.82334 (12)0.90287 (8)0.0180 (2)
O40.31349 (16)0.68239 (12)0.45992 (8)0.0197 (3)
O1w0.35758 (17)0.17412 (13)0.73409 (8)0.0200 (3)
O2w0.75855 (17)0.38643 (13)0.97416 (9)0.0221 (3)
O3w0.34432 (17)1.12598 (13)0.91713 (8)0.0213 (3)
O4w0.01511 (18)0.30256 (13)0.69710 (9)0.0231 (3)
O5w1.07168 (17)0.33392 (13)0.90316 (9)0.0232 (3)
N10.29295 (19)0.91884 (14)0.55157 (9)0.0162 (3)
N20.24067 (18)0.97264 (14)0.46592 (9)0.0165 (3)
N30.08352 (19)1.39294 (15)0.34212 (10)0.0183 (3)
C10.4530 (2)0.58425 (16)0.63391 (11)0.0147 (3)
H10.47530.52740.57290.018*
C20.5040 (2)0.53102 (16)0.71918 (11)0.0146 (3)
C30.4698 (2)0.61229 (17)0.80875 (11)0.0151 (3)
C40.3855 (2)0.74827 (16)0.81103 (11)0.0147 (3)
C50.3332 (2)0.80233 (16)0.72644 (11)0.0148 (3)
H50.27330.89420.72900.018*
C60.3693 (2)0.72070 (16)0.63685 (10)0.0140 (3)
C70.3236 (2)0.77172 (16)0.54225 (11)0.0144 (3)
C80.2179 (2)1.11562 (17)0.48486 (11)0.0168 (3)
H80.23541.17000.55280.020*
C90.1240 (2)1.34618 (17)0.42795 (11)0.0175 (3)
H90.12261.40730.49210.021*
C100.1675 (2)1.19684 (17)0.40875 (11)0.0158 (3)
C110.1553 (2)1.14989 (17)0.30295 (11)0.0154 (3)
C120.1934 (2)1.01736 (17)0.23897 (11)0.0194 (3)
H12A0.22990.93100.26320.023*
C130.1763 (2)1.01605 (19)0.13982 (12)0.0229 (4)
H130.20230.92750.09560.028*
C140.1213 (2)1.1422 (2)0.10270 (12)0.0241 (4)
H140.10931.13670.03380.029*
C150.0845 (2)1.27369 (19)0.16400 (12)0.0212 (3)
H150.04781.35940.13900.025*
C160.1033 (2)1.27600 (17)0.26438 (11)0.0169 (3)
H1o0.616 (3)0.370 (2)0.6634 (10)0.046 (7)*
H2o0.584 (3)0.4971 (18)0.8974 (16)0.039 (6)*
H3o0.333 (3)0.9129 (14)0.8998 (16)0.038 (6)*
H1n0.314 (3)0.9850 (17)0.6102 (9)0.025 (5)*
H3n0.052 (3)1.4844 (15)0.3374 (17)0.046 (6)*
H110.438 (3)0.235 (2)0.7274 (19)0.060 (8)*
H120.380 (4)0.163 (3)0.7939 (10)0.059 (8)*
H210.719 (3)0.336 (2)1.0090 (16)0.055 (7)*
H220.848 (3)0.349 (4)0.952 (2)0.112 (13)*
H310.255 (3)1.184 (3)0.915 (2)0.067 (9)*
H320.425 (2)1.158 (2)0.9721 (10)0.037 (6)*
H410.117 (2)0.260 (3)0.7001 (18)0.055 (8)*
H42−0.066 (3)0.242 (2)0.6537 (15)0.063 (8)*
H511.039 (3)0.331 (3)0.8414 (8)0.055 (8)*
H521.124 (4)0.4219 (19)0.932 (2)0.101 (12)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0248 (6)0.0168 (5)0.0172 (6)0.0079 (5)0.0091 (5)0.0068 (4)
O20.0281 (7)0.0247 (6)0.0164 (6)0.0119 (5)0.0081 (5)0.0099 (5)
O30.0241 (6)0.0179 (6)0.0123 (5)0.0060 (5)0.0060 (4)0.0026 (4)
O40.0282 (6)0.0169 (5)0.0131 (5)0.0037 (5)0.0051 (5)0.0021 (4)
O1w0.0247 (6)0.0202 (6)0.0156 (6)0.0008 (5)0.0053 (5)0.0051 (4)
O2w0.0242 (7)0.0240 (6)0.0223 (6)0.0054 (5)0.0101 (5)0.0094 (5)
O3w0.0235 (6)0.0233 (6)0.0155 (6)0.0042 (5)0.0031 (5)0.0032 (4)
O4w0.0217 (6)0.0249 (6)0.0217 (6)0.0056 (5)0.0035 (5)0.0057 (5)
O5w0.0249 (7)0.0234 (6)0.0203 (6)0.0028 (5)0.0070 (5)0.0023 (5)
N10.0228 (7)0.0147 (6)0.0106 (6)0.0027 (5)0.0029 (5)0.0037 (5)
N20.0201 (7)0.0179 (6)0.0127 (6)0.0027 (5)0.0041 (5)0.0063 (5)
N30.0196 (7)0.0150 (6)0.0212 (7)0.0033 (5)0.0041 (5)0.0069 (5)
C10.0158 (7)0.0148 (7)0.0129 (7)0.0006 (6)0.0040 (6)0.0019 (5)
C20.0143 (7)0.0127 (7)0.0176 (7)0.0014 (6)0.0046 (6)0.0043 (6)
C30.0144 (7)0.0181 (7)0.0138 (7)0.0005 (6)0.0034 (6)0.0060 (6)
C40.0140 (7)0.0166 (7)0.0126 (7)−0.0003 (6)0.0046 (6)0.0009 (5)
C50.0158 (7)0.0131 (7)0.0152 (7)0.0019 (6)0.0040 (6)0.0028 (5)
C60.0136 (7)0.0148 (7)0.0125 (7)−0.0014 (6)0.0019 (5)0.0030 (5)
C70.0142 (7)0.0159 (7)0.0132 (7)0.0002 (6)0.0033 (6)0.0037 (5)
C80.0191 (8)0.0175 (7)0.0136 (7)0.0022 (6)0.0041 (6)0.0032 (6)
C90.0177 (8)0.0176 (7)0.0169 (7)0.0013 (6)0.0038 (6)0.0043 (6)
C100.0164 (7)0.0154 (7)0.0155 (7)0.0012 (6)0.0035 (6)0.0042 (6)
C110.0153 (7)0.0175 (7)0.0134 (7)−0.0011 (6)0.0027 (6)0.0046 (6)
C120.0202 (8)0.0174 (7)0.0194 (8)−0.0010 (6)0.0042 (6)0.0031 (6)
C130.0249 (9)0.0226 (8)0.0191 (8)−0.0037 (7)0.0070 (7)−0.0005 (6)
C140.0242 (9)0.0322 (9)0.0145 (7)−0.0084 (7)0.0028 (6)0.0054 (6)
C150.0185 (8)0.0264 (8)0.0191 (8)−0.0041 (7)0.0002 (6)0.0109 (6)
C160.0137 (7)0.0184 (7)0.0178 (7)−0.0017 (6)0.0016 (6)0.0054 (6)

Geometric parameters (Å, °)

O1—C21.3777 (18)C1—C21.383 (2)
O1—H1o0.845 (9)C1—C61.393 (2)
O2—C31.3615 (18)C1—H10.9500
O2—H2o0.839 (10)C2—C31.392 (2)
O3—C41.3801 (17)C3—C41.392 (2)
O3—H3o0.851 (10)C4—C51.379 (2)
O4—C71.2400 (17)C5—C61.399 (2)
O1w—H110.850 (10)C5—H50.9500
O1w—H120.855 (10)C6—C71.490 (2)
O2w—H210.843 (10)C8—C101.433 (2)
O2w—H220.846 (10)C8—H80.9500
O3w—H310.854 (10)C9—C101.381 (2)
O3w—H320.848 (10)C9—H90.9500
O4w—H410.848 (10)C10—C111.441 (2)
O4w—H420.839 (10)C11—C121.404 (2)
O5w—H510.847 (10)C11—C161.408 (2)
O5w—H520.850 (10)C12—C131.380 (2)
N1—C71.3434 (19)C12—H12A0.9500
N1—N21.3910 (17)C13—C141.402 (2)
N1—H1n0.882 (9)C13—H130.9500
N2—C81.288 (2)C14—C151.375 (2)
N3—C91.354 (2)C14—H140.9500
N3—C161.376 (2)C15—C161.394 (2)
N3—H3n0.882 (10)C15—H150.9500
C2—O1—H1o106.5 (16)C5—C6—C7123.54 (13)
C3—O2—H2o115.8 (15)O4—C7—N1122.36 (13)
C4—O3—H3o107.5 (14)O4—C7—C6121.46 (13)
H11—O1w—H12112 (2)N1—C7—C6116.18 (13)
H21—O2w—H22114 (3)N2—C8—C10123.34 (14)
H31—O3w—H32109 (2)N2—C8—H8118.3
H41—O4w—H42107 (2)C10—C8—H8118.3
H51—O5w—H52106 (3)N3—C9—C10110.20 (14)
C7—N1—N2119.24 (12)N3—C9—H9124.9
C7—N1—H1n122.5 (12)C10—C9—H9124.9
N2—N1—H1n118.0 (12)C9—C10—C8123.34 (14)
C8—N2—N1113.26 (12)C9—C10—C11106.25 (13)
C9—N3—C16109.03 (13)C8—C10—C11130.40 (14)
C9—N3—H3n125.2 (15)C12—C11—C16119.25 (14)
C16—N3—H3n125.7 (15)C12—C11—C10134.26 (14)
C2—C1—C6120.49 (13)C16—C11—C10106.36 (13)
C2—C1—H1119.8C13—C12—C11118.14 (15)
C6—C1—H1119.8C13—C12—H12A120.9
O1—C2—C1122.20 (13)C11—C12—H12A120.9
O1—C2—C3117.48 (13)C12—C13—C14121.62 (15)
C1—C2—C3120.29 (14)C12—C13—H13119.2
O2—C3—C4116.52 (13)C14—C13—H13119.2
O2—C3—C2124.59 (14)C15—C14—C13121.35 (15)
C4—C3—C2118.89 (13)C15—C14—H14119.3
O3—C4—C5123.17 (14)C13—C14—H14119.3
O3—C4—C3115.42 (13)C14—C15—C16117.23 (15)
C5—C4—C3121.41 (13)C14—C15—H15121.4
C4—C5—C6119.40 (14)C16—C15—H15121.4
C4—C5—H5120.3N3—C16—C15129.42 (14)
C6—C5—H5120.3N3—C16—C11108.14 (13)
C1—C6—C5119.50 (13)C15—C16—C11122.40 (15)
C1—C6—C7116.96 (13)
C7—N1—N2—C8−179.15 (14)N1—N2—C8—C10178.78 (14)
C6—C1—C2—O1−176.94 (13)C16—N3—C9—C10−1.24 (18)
C6—C1—C2—C30.9 (2)N3—C9—C10—C8179.52 (14)
O1—C2—C3—O2−1.9 (2)N3—C9—C10—C110.96 (18)
C1—C2—C3—O2−179.82 (14)N2—C8—C10—C9172.92 (15)
O1—C2—C3—C4177.27 (13)N2—C8—C10—C11−8.9 (3)
C1—C2—C3—C4−0.7 (2)C9—C10—C11—C12175.33 (17)
O2—C3—C4—O30.3 (2)C8—C10—C11—C12−3.1 (3)
C2—C3—C4—O3−178.94 (13)C9—C10—C11—C16−0.34 (17)
O2—C3—C4—C5−179.82 (13)C8—C10—C11—C16−178.76 (16)
C2—C3—C4—C51.0 (2)C16—C11—C12—C13−0.6 (2)
O3—C4—C5—C6178.43 (13)C10—C11—C12—C13−175.81 (16)
C3—C4—C5—C6−1.5 (2)C11—C12—C13—C14−0.4 (2)
C2—C1—C6—C5−1.4 (2)C12—C13—C14—C150.9 (3)
C2—C1—C6—C7178.38 (13)C13—C14—C15—C16−0.3 (2)
C4—C5—C6—C11.7 (2)C9—N3—C16—C15−176.86 (16)
C4—C5—C6—C7−178.10 (13)C9—N3—C16—C110.99 (17)
N2—N1—C7—O42.7 (2)C14—C15—C16—N3176.83 (16)
N2—N1—C7—C6−176.87 (12)C14—C15—C16—C11−0.8 (2)
C1—C6—C7—O418.6 (2)C12—C11—C16—N3−176.83 (14)
C5—C6—C7—O4−161.64 (14)C10—C11—C16—N3−0.38 (17)
C1—C6—C7—N1−161.86 (13)C12—C11—C16—C151.2 (2)
C5—C6—C7—N117.9 (2)C10—C11—C16—C15177.65 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1o···O4i0.85 (1)1.90 (1)2.740 (2)174 (2)
O2—H2o···O2w0.84 (1)1.94 (1)2.697 (2)149 (2)
O3—H3o···O3w0.85 (1)1.90 (1)2.724 (2)164 (2)
N1—H1n···O1wii0.88 (1)2.11 (1)2.978 (2)169 (2)
N3—H3n···O4wiii0.88 (1)2.15 (1)3.024 (2)171 (2)
O1w—H11···O10.85 (1)1.93 (1)2.771 (2)170 (3)
O1w—H12···O3wiv0.86 (1)1.94 (1)2.760 (2)161 (3)
O2w—H21···O3v0.84 (1)2.29 (1)3.123 (2)172 (2)
O2w—H22···O5w0.85 (1)1.94 (2)2.753 (2)161 (3)
O3w—H31···O5wvi0.85 (1)1.95 (1)2.796 (2)172 (3)
O3w—H32···O3vii0.85 (1)2.06 (1)2.890 (2)165 (2)
O4w—H41···O1w0.85 (1)1.97 (1)2.803 (2)169 (2)
O4w—H42···O4viii0.84 (1)2.37 (2)2.921 (2)124 (2)
O4w—H42···N2viii0.84 (1)2.39 (1)3.211 (2)166 (2)
O5w—H51···O4wix0.85 (1)1.97 (1)2.798 (2)167 (2)
O5w—H52···O2wx0.85 (1)1.97 (1)2.810 (2)168 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z; (iii) −x, −y+2, −z+1; (iv) x, y−1, z; (v) −x+1, −y+1, −z+2; (vi) x−1, y+1, z; (vii) −x+1, −y+2, −z+2; (viii) −x, −y+1, −z+1; (ix) x+1, y, z; (x) −x+2, −y+1, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2335).

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. (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