PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2108.
Published online 2008 October 11. doi:  10.1107/S1600536808031991
PMCID: PMC2959687

N′-(5-Bromo-1H-indol-3-ylmethyl­idene)-3,4,5-trihydroxy­benzohydrazide

Abstract

The two aromatic parts of the title mol­ecule, C16H12BrN3O4, are connected through a conjugated –CH=N—NH—C(O)– fragment to furnish an almost planar mol­ecule. Adjacent mol­ecules are linked by N—H(...)O and O—H(...)O hydrogen bonds into a three-dimensional network. An intramolecular O—H(...)O link also occurs.

Related literature

For other Schiff bases derived by condensing 5-bromo-1H-indole-3-carbaldehyde with aroylhydrazines, see: Ali et al. (2005a [triangle],b [triangle],c [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2108-scheme1.jpg

Experimental

Crystal data

  • C16H12BrN3O4
  • M r = 390.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2108-efi1.jpg
  • a = 9.6454 (2) Å
  • b = 14.9694 (4) Å
  • c = 10.3845 (2) Å
  • β = 97.390 (1)°
  • V = 1486.92 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.79 mm−1
  • T = 100 (2) K
  • 0.40 × 0.25 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.401, T max = 0.768
  • 10182 measured reflections
  • 3403 independent reflections
  • 2786 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.029
  • wR(F 2) = 0.078
  • S = 1.02
  • 3403 reflections
  • 220 parameters
  • H-atom parameters constrained
  • Δρmax = 0.62 e Å−3
  • Δρmin = −0.36 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 global, I. DOI: 10.1107/S1600536808031991/tk2310sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031991/tk2310Isup2.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).

supplementary crystallographic information

Comment

The molecule of (I), Fig. 1, is almost planar with the aromatic groups connected via a conjugated –CH═N–NH–C(O)– fragment. Molecules are connected into a 3-D network via N—H···O and O—H···O hydrogen bonds, Table 1.

Experimental

5-Bromoindole-3-carbaldehyde (0.34 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 solution was set aside for the growth of crystals.

Refinement

Hydrogen atoms were placed at calculated positions (C—H 0.95, N—H 0.88 and O—H 0.84 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2–1.5 times Ueq(C,N,O). For the hydroxy groups, an sp2 type of hybridization was assumed.

Figures

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

Crystal data

C16H12BrN3O4F(000) = 784
Mr = 390.20Dx = 1.743 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3960 reflections
a = 9.6454 (2) Åθ = 2.4–28.2°
b = 14.9694 (4) ŵ = 2.79 mm1
c = 10.3845 (2) ÅT = 100 K
β = 97.390 (1)°Block, orange
V = 1486.92 (6) Å30.40 × 0.25 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer3403 independent reflections
Radiation source: fine-focus sealed tube2786 reflections with I > 2σ(I)
graphiteRint = 0.024
ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→11
Tmin = 0.401, Tmax = 0.768k = −19→19
10182 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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0419P)2 + 0.9663P] where P = (Fo2 + 2Fc2)/3
3403 reflections(Δ/σ)max = 0.003
220 parametersΔρmax = 0.62 e Å3
0 restraintsΔρmin = −0.36 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.

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

xyzUiso*/Ueq
Br11.00401 (2)1.090710 (16)0.25205 (2)0.02243 (8)
O10.69032 (15)0.83598 (10)0.56939 (13)0.0157 (3)
O20.64359 (15)0.62930 (10)0.94165 (13)0.0163 (3)
H2O0.59870.59990.99140.024*
O30.37031 (15)0.59355 (9)0.93388 (13)0.0133 (3)
H3O0.30850.61780.97210.020*
O40.17544 (15)0.67374 (10)0.73325 (13)0.0141 (3)
H4O0.15690.64210.79560.021*
N10.46882 (18)0.86863 (11)0.48158 (15)0.0134 (3)
H1N0.37880.86190.48520.016*
N20.51457 (18)0.92346 (11)0.38712 (16)0.0129 (3)
N30.40143 (19)1.10565 (11)0.03097 (16)0.0151 (4)
H3N0.35571.1326−0.03690.018*
C10.5056 (2)0.76400 (13)0.66032 (18)0.0123 (4)
C20.6012 (2)0.72451 (13)0.75620 (18)0.0129 (4)
H20.69840.73610.75980.016*
C30.5519 (2)0.66829 (13)0.84567 (18)0.0128 (4)
C40.4097 (2)0.65084 (13)0.84261 (18)0.0116 (4)
C50.3160 (2)0.68919 (13)0.74520 (18)0.0122 (4)
C60.3639 (2)0.74523 (13)0.65414 (18)0.0124 (4)
H60.29960.77090.58730.015*
C70.5628 (2)0.82603 (13)0.56719 (18)0.0128 (4)
C80.4168 (2)0.96589 (13)0.31563 (19)0.0133 (4)
H80.32290.95870.33240.016*
C90.4446 (2)1.02350 (13)0.21187 (19)0.0125 (4)
C100.3424 (2)1.05580 (14)0.11812 (19)0.0150 (4)
H100.24511.04470.11520.018*
C110.5760 (2)1.05663 (13)0.17868 (18)0.0121 (4)
C120.7151 (2)1.05011 (13)0.23622 (18)0.0135 (4)
H120.73991.01770.31440.016*
C130.8147 (2)1.09278 (13)0.1744 (2)0.0152 (4)
C140.7829 (2)1.14153 (14)0.0594 (2)0.0172 (4)
H140.85581.16850.01950.021*
C150.6456 (2)1.15045 (14)0.00394 (19)0.0158 (4)
H150.62151.1845−0.07280.019*
C160.5443 (2)1.10761 (13)0.06493 (19)0.0138 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.01187 (12)0.03131 (14)0.02403 (13)−0.00169 (9)0.00198 (8)0.00285 (9)
O10.0119 (7)0.0181 (7)0.0178 (7)−0.0008 (6)0.0047 (6)0.0012 (6)
O20.0100 (7)0.0235 (8)0.0151 (7)−0.0005 (6)0.0010 (6)0.0048 (6)
O30.0120 (7)0.0162 (7)0.0122 (6)0.0003 (6)0.0039 (5)0.0011 (5)
O40.0101 (7)0.0174 (7)0.0145 (7)−0.0035 (6)0.0005 (5)0.0038 (5)
N10.0114 (9)0.0144 (8)0.0152 (8)−0.0019 (7)0.0050 (7)0.0021 (7)
N20.0149 (9)0.0123 (8)0.0125 (7)−0.0020 (7)0.0051 (7)−0.0006 (6)
N30.0158 (9)0.0156 (9)0.0133 (8)0.0028 (7)−0.0004 (7)−0.0001 (6)
C10.0123 (10)0.0122 (9)0.0133 (9)−0.0012 (8)0.0044 (7)−0.0035 (7)
C20.0093 (9)0.0150 (9)0.0150 (9)0.0001 (8)0.0031 (7)−0.0024 (8)
C30.0116 (10)0.0149 (10)0.0116 (8)0.0016 (8)−0.0002 (7)−0.0027 (7)
C40.0133 (10)0.0111 (9)0.0109 (8)−0.0017 (7)0.0035 (7)−0.0017 (7)
C50.0101 (9)0.0126 (9)0.0143 (9)−0.0010 (8)0.0025 (7)−0.0042 (7)
C60.0119 (10)0.0124 (9)0.0127 (9)0.0006 (8)0.0009 (7)0.0003 (7)
C70.0148 (10)0.0114 (9)0.0131 (9)−0.0005 (8)0.0046 (8)−0.0044 (7)
C80.0117 (10)0.0133 (9)0.0155 (9)−0.0012 (8)0.0042 (7)−0.0031 (8)
C90.0131 (10)0.0104 (9)0.0141 (9)0.0005 (8)0.0018 (8)−0.0029 (7)
C100.0144 (10)0.0146 (9)0.0162 (9)0.0008 (8)0.0027 (8)−0.0021 (8)
C110.0148 (10)0.0099 (9)0.0119 (8)0.0009 (8)0.0032 (7)−0.0025 (7)
C120.0165 (10)0.0125 (9)0.0116 (9)0.0023 (8)0.0028 (7)−0.0013 (7)
C130.0132 (10)0.0146 (10)0.0176 (9)0.0000 (8)0.0017 (8)−0.0028 (8)
C140.0194 (11)0.0149 (10)0.0185 (10)−0.0026 (9)0.0072 (8)−0.0002 (8)
C150.0233 (11)0.0116 (9)0.0128 (9)0.0002 (8)0.0035 (8)0.0004 (7)
C160.0166 (10)0.0117 (9)0.0126 (9)0.0021 (8)0.0005 (8)−0.0024 (7)

Geometric parameters (Å, °)

Br1—C131.899 (2)C2—H20.9500
O1—C71.236 (3)C3—C41.392 (3)
O2—C31.375 (2)C4—C51.391 (3)
O2—H2O0.8400C5—C61.387 (3)
O3—C41.368 (2)C6—H60.9500
O3—H3O0.8400C8—C91.432 (3)
O4—C51.365 (2)C8—H80.9500
O4—H4O0.8400C9—C101.381 (3)
N1—C71.346 (3)C9—C111.443 (3)
N1—N21.394 (2)C10—H100.9500
N1—H1N0.8800C11—C121.401 (3)
N2—C81.290 (3)C11—C161.406 (3)
N3—C101.354 (3)C12—C131.379 (3)
N3—C161.378 (3)C12—H120.9500
N3—H3N0.8800C13—C141.400 (3)
C1—C61.388 (3)C14—C151.381 (3)
C1—C21.398 (3)C14—H140.9500
C1—C71.497 (3)C15—C161.388 (3)
C2—C31.382 (3)C15—H150.9500
C3—O2—H2O109.5O1—C7—C1120.77 (18)
C4—O3—H3O109.5N1—C7—C1116.61 (18)
C5—O4—H4O109.5N2—C8—C9122.40 (19)
C7—N1—N2119.79 (17)N2—C8—H8118.8
C7—N1—H1N120.1C9—C8—H8118.8
N2—N1—H1N120.1C10—C9—C8123.76 (19)
C8—N2—N1114.89 (17)C10—C9—C11106.28 (17)
C10—N3—C16109.48 (17)C8—C9—C11129.92 (19)
C10—N3—H3N125.3N3—C10—C9109.93 (19)
C16—N3—H3N125.3N3—C10—H10125.0
C6—C1—C2120.15 (18)C9—C10—H10125.0
C6—C1—C7122.57 (18)C12—C11—C16119.25 (18)
C2—C1—C7117.28 (18)C12—C11—C9134.17 (18)
C3—C2—C1118.93 (18)C16—C11—C9106.54 (18)
C3—C2—H2120.5C13—C12—C11117.12 (18)
C1—C2—H2120.5C13—C12—H12121.4
O2—C3—C2120.06 (18)C11—C12—H12121.4
O2—C3—C4118.49 (17)C12—C13—C14123.3 (2)
C2—C3—C4121.44 (18)C12—C13—Br1118.96 (15)
O3—C4—C3117.54 (18)C14—C13—Br1117.63 (16)
O3—C4—C5123.37 (18)C15—C14—C13119.95 (19)
C3—C4—C5119.04 (18)C15—C14—H14120.0
O4—C5—C6117.06 (17)C13—C14—H14120.0
O4—C5—C4122.77 (17)C14—C15—C16117.31 (19)
C6—C5—C4120.17 (19)C14—C15—H15121.3
C1—C6—C5120.23 (18)C16—C15—H15121.3
C1—C6—H6119.9N3—C16—C15129.25 (19)
C5—C6—H6119.9N3—C16—C11107.77 (18)
O1—C7—N1122.61 (18)C15—C16—C11122.99 (19)
C7—N1—N2—C8−175.49 (18)N2—C8—C9—C10166.76 (19)
C6—C1—C2—C3−1.3 (3)N2—C8—C9—C11−10.6 (3)
C7—C1—C2—C3178.65 (17)C16—N3—C10—C90.0 (2)
C1—C2—C3—O2−179.39 (17)C8—C9—C10—N3−177.81 (18)
C1—C2—C3—C4−0.4 (3)C11—C9—C10—N30.1 (2)
O2—C3—C4—O3−1.8 (3)C10—C9—C11—C12177.6 (2)
C2—C3—C4—O3179.23 (17)C8—C9—C11—C12−4.7 (4)
O2—C3—C4—C5−179.37 (17)C10—C9—C11—C16−0.1 (2)
C2—C3—C4—C51.7 (3)C8—C9—C11—C16177.60 (19)
O3—C4—C5—O40.9 (3)C16—C11—C12—C13−1.9 (3)
C3—C4—C5—O4178.29 (17)C9—C11—C12—C13−179.3 (2)
O3—C4—C5—C6−178.58 (18)C11—C12—C13—C140.2 (3)
C3—C4—C5—C6−1.2 (3)C11—C12—C13—Br1177.22 (14)
C2—C1—C6—C51.8 (3)C12—C13—C14—C151.6 (3)
C7—C1—C6—C5−178.16 (18)Br1—C13—C14—C15−175.44 (15)
O4—C5—C6—C1179.97 (17)C13—C14—C15—C16−1.7 (3)
C4—C5—C6—C1−0.6 (3)C10—N3—C16—C15−179.9 (2)
N2—N1—C7—O12.9 (3)C10—N3—C16—C110.0 (2)
N2—N1—C7—C1−176.32 (16)C14—C15—C16—N3179.8 (2)
C6—C1—C7—O1−174.49 (18)C14—C15—C16—C110.0 (3)
C2—C1—C7—O15.5 (3)C12—C11—C16—N3−178.04 (17)
C6—C1—C7—N14.7 (3)C9—C11—C16—N30.1 (2)
C2—C1—C7—N1−175.23 (17)C12—C11—C16—C151.8 (3)
N1—N2—C8—C9−178.50 (17)C9—C11—C16—C15179.91 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2O···O30.842.212.681 (2)116
O3—H3O···O1i0.841.762.595 (2)173
O4—H4O···N2i0.842.022.778 (2)150
N1—H1N···O2ii0.882.263.111 (2)163
N3—H3N···O4iii0.882.112.932 (2)154

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: TK2310).

References

  • Ali, H. M., Abdul Halim, S. N., Lajis, N. H., Basirun, W. J., Zain, S. M. & Ng, S. W. (2005a). Acta Cryst. E61, o914–o915.
  • Ali, H. M., Abdul Halim, S. N. & Ng, S. W. (2005b). Acta Cryst. E61, o2308–o2309.
  • Ali, H. M., Abdul Halim, S. N. & Ng, S. W. (2005c). Acta Cryst. E61, o2417–o2418.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • 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