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Acta Cryst. (2008). E64, o2108    [ doi:10.1107/S1600536808031991 ]

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

H. Khaledi, H. Mohd Ali and S. W. Ng

Abstract top

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.

Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (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, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of (I) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
N'-(5-Bromo-1H-indol-3-ylmethylidene)-3,4,5- trihydroxybenzohydrazide top
Crystal data top
C16H12BrN3O4F(000) = 784
Mr = 390.20Dx = 1.743 Mg m−3
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 mm−1
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 top
Bruker SMART APEX
diffractometer		3403 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 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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-atom parameters constrained
S = 1.02 w = 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 Å−3
0 restraintsΔρmin = −0.36 e Å−3
Crystal data top
C16H12BrN3O4V = 1486.92 (6) Å3
Mr = 390.20Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.6454 (2) ŵ = 2.79 mm−1
b = 14.9694 (4) ÅT = 100 K
c = 10.3845 (2) Å0.40 × 0.25 × 0.10 mm
β = 97.390 (1)°
Data collection top
Bruker SMART APEX
diffractometer		3403 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2786 reflections with I > 2σ(I)
Tmin = 0.401, Tmax = 0.768Rint = 0.024
10182 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.078Δρmax = 0.62 e Å−3
S = 1.02Δρmin = −0.36 e Å−3
3403 reflectionsAbsolute structure: ?
220 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

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

references
References top

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.

Westrip, S. P. (2008). publCIF. In preparation.