organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 15 December 2008; accepted 15 December 2008; online 20 December 2008)

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[Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008). Acta Cryst. E64, o2108.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12ClN3O4

  • Mr = 345.74

  • Monoclinic, P 21 /n

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.914, Tmax = 0.966

  • 10185 measured reflections

  • 3389 independent reflections

  • 2907 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2o⋯O3 0.84 2.20 2.6726 (14) 116
O3—H3o⋯O1i 0.84 1.74 2.5818 (14) 175
O4—H4o⋯N2i 0.84 2.01 2.7668 (15) 149
N1—H1n⋯O2ii 0.88 2.23 3.0875 (16) 163
N3—H3n⋯O4iii 0.88 2.15 2.9518 (15) 152
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C16H12ClN3O4 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
N'-[(5-Chloro-1H-indol-3-yl)methylene]-3,4,5-trihydroxybenzohydrazide top
Crystal data top
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 top
Bruker SMART APEX
diffractometer
3389 independent reflections
Radiation source: fine-focus sealed tube2907 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1112
Tmin = 0.914, Tmax = 0.966k = 1919
10185 measured reflectionsl = 1313
Refinement top
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 = 1.06 w = 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
Crystal data top
C16H12ClN3O4V = 1477.64 (5) Å3
Mr = 345.74Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.6481 (2) ŵ = 0.29 mm1
b = 15.1408 (3) ÅT = 100 K
c = 10.2206 (2) Å0.32 × 0.22 × 0.12 mm
β = 98.232 (1)°
Data collection top
Bruker SMART APEX
diffractometer
3389 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2907 reflections with I > 2σ(I)
Tmin = 0.914, Tmax = 0.966Rint = 0.025
10185 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.093H-atom parameters constrained
S = 1.06Δρmax = 0.34 e Å3
3389 reflectionsΔρmin = 0.33 e Å3
220 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H3N0.35441.13610.03690.019*
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)
H150.62351.18230.07270.021*
C160.54321 (16)1.10616 (9)0.06539 (13)0.0146 (3)
Atomic displacement parameters (Å2) top
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, º) top
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—C8175.96 (12)N2—C8—C9—C10166.52 (13)
C6—C1—C2—C31.2 (2)N2—C8—C9—C1110.3 (2)
C7—C1—C2—C3178.31 (12)C16—N3—C10—C90.12 (16)
C1—C2—C3—O2179.47 (12)C8—C9—C10—N3177.25 (12)
C1—C2—C3—C40.5 (2)C11—C9—C10—N30.18 (15)
O2—C3—C4—O31.36 (18)C10—C9—C11—C12177.59 (15)
C2—C3—C4—O3179.69 (12)C8—C9—C11—C125.2 (3)
O2—C3—C4—C5178.98 (12)C10—C9—C11—C160.17 (15)
C2—C3—C4—C52.1 (2)C8—C9—C11—C16177.04 (14)
O3—C4—C5—O40.2 (2)C16—C11—C12—C131.65 (19)
C3—C4—C5—O4177.70 (12)C9—C11—C12—C13179.19 (14)
O3—C4—C5—C6179.32 (12)C11—C12—C13—C140.7 (2)
C3—C4—C5—C61.9 (2)C11—C12—C13—Cl1178.50 (10)
O4—C5—C6—C1179.44 (12)C12—C13—C14—C150.8 (2)
C4—C5—C6—C10.2 (2)Cl1—C13—C14—C15176.97 (11)
C2—C1—C6—C51.4 (2)C13—C14—C15—C161.3 (2)
C7—C1—C6—C5178.09 (12)C10—N3—C16—C15179.12 (14)
N2—N1—C7—O12.73 (19)C10—N3—C16—C110.00 (15)
N2—N1—C7—C1176.29 (11)C14—C15—C16—N3179.40 (14)
C6—C1—C7—O1173.65 (13)C14—C15—C16—C110.4 (2)
C2—C1—C7—O16.83 (19)C12—C11—C16—N3178.05 (12)
C6—C1—C7—N15.39 (19)C9—C11—C16—N30.11 (15)
C2—C1—C7—N1174.13 (12)C12—C11—C16—C151.1 (2)
N1—N2—C8—C9178.92 (12)C9—C11—C16—C15179.30 (13)
Hydrogen-bond geometry (Å, º) top
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) x1/2, y+3/2, z+1/2; (ii) x1/2, y+3/2, z1/2; (iii) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC16H12ClN3O4
Mr345.74
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)9.6481 (2), 15.1408 (3), 10.2206 (2)
β (°) 98.232 (1)
V3)1477.64 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.29
Crystal size (mm)0.32 × 0.22 × 0.12
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.914, 0.966
No. of measured, independent and
observed [I > 2σ(I)] reflections
10185, 3389, 2907
Rint0.025
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.093, 1.06
No. of reflections3389
No. of parameters220
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.33

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
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) x1/2, y+3/2, z+1/2; (ii) x1/2, y+3/2, z1/2; (iii) x+1/2, y+1/2, z+1/2.
 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKhaledi, H., Mohd Ali, H. & Ng, S. W. (2008). Acta Cryst. E64, o2108.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds