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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2999
https://doi.org/10.1107/S1600536810043357

5-Bromo-2-hy­dr­oxy­benzaldehyde thio­semicarbazone

Hadi Kargar,a Reza Kia,b Mehmet Akkurtc* and Orhan Büyükgüngörd

aDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran, bDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, cDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, and dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 24 October 2010; accepted 24 October 2010; online 31 October 2010)

The mol­ecule of the title compound, C8H8BrN3OS, is close to being planar, with maximum deviations of −0.127 (3) and 0.135 (5) Å for the N atoms of the –NH– and NH2– groups, respectively. Intra­molecular N—H⋯N and O—H⋯N hydrogen bonds to the same acceptor N atom generate S(5) and S(6) ring motifs. In the crystal structure, mol­ecules are connected into [010] chains by pairs of N—H⋯S hydrogen bonds with R22(8) graph-set motifs. The crystal used for data collection was found to be an inversion twin.

Related literature

For background on the biological activities and pharmaceutical properties of thio­semicarbazones and their derivatives, see: Casas et al. (2000[Casas, J. S., Garcia-Tasende, M. S. & Sordo, J. (2000). Coord. Chem. Rev. 209, 197-261.]); Ferrari et al. (2000[Ferrari, M. B., Capacchi, S., Reffo, G., Pelosi, G., Tarasconi, P., Albertini, R., Pinelli, S. & Lunghi, P. (2000). J. Inorg. Biochem. 81, 89-97.]); Maccioni et al. (2003[Maccioni, E., Cardia, M. C., Distinto, S., Bonsignore, L. & De Logu, A. (2003). Il Farmaco, 58, 951-959.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C8H8BrN3OS

  • Mr = 274.14

  • Orthorhombic, P 21 21 21

  • a = 4.4564 (2) Å

  • b = 8.3515 (3) Å

  • c = 27.7153 (14) Å

  • V = 1031.50 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 4.16 mm−1

  • T = 296 K

  • 0.13 × 0.09 × 0.05 mm
Data collection

  • Stoe IPDS II diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.614, Tmax = 0.819

  • 9532 measured reflections

  • 1934 independent reflections

  • 1782 reflections with I > 2σ(I)

  • Rint = 0.037
Refinement

  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.063

  • S = 1.04

  • 1934 reflections

  • 144 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.54 e Å−3

  • Δρmin = −0.29 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), with 744 Freidel pairs

  • Flack parameter: 0.477 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—HO1⋯N1 0.81 (3) 1.97 (4) 2.685 (4) 149 (5)
N3—HN3⋯N1 0.87 (4) 2.30 (4) 2.688 (5) 107 (3)
N2—HN1⋯S1i 0.84 (3) 2.55 (3) 3.373 (3) 168 (3)
N3—HN2⋯S1ii 0.86 (3) 2.50 (3) 3.363 (4) 176 (6)
Symmetry codes: (i) [-x-1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x-1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810043357/hb5704sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043357/hb5704Isup2.hkl

checkCIF report


Comment top

Thiosemicarbazones constitute an important class of N,S donor ligands due to their propensity to react with a wide range of metals (Casas et al., 2000). Thiosemicarbazones exhibit various biological activities and have therefore attracted considerable pharmaceutical interest (Maccioni et al., 2003; Ferrari et al., 2000). We here report the crystal structure of the title compound (I).

The title molecule (I) shown in Fig. 1 is almost planar with the maximum deviations of -0.127 (3) Å for N2 and 0.135 (5) Å for N3. All bond lengths and angles are normal (Allen et al., 1987). In each independent molecule, there are intramolecular N—H···N and O—H···N hydrogen bonds, generating the S(5) and S(6) ring motifs, respectively (Table 1, Fig. 2).

In the crystal structure, adjacent molecules are linked by N—H···S hydrogen bonds, forming R22(8) dimers (Bernstein et al., 1995) (Table 1, Fig. 2).

Related literature top

For background on the biological activities and pharmaceutical properties of thiosemicarbazones and their derivatives, see: Casas et al. (2000); Ferrari et al. (2000); Maccioni et al. (2003). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 5-bromosalicylalehyde (0.01 mol) and hydrazinecarbothioamide (0.01 mol) in 20 ml of ethanol was refluxed for about 2 h. On cooling, the solid separated was filtered and recrystallized from ethanol to yield colourless prisms of (I).

Refinement top

The H atoms of the O—H, N—H and NH2 groups were found from a difference Fourier map and their positional parameters were constrained [O1—H1 = 0.81 (3) and N2—HN1 = 0.84 (3), N3—HN2 = 0.86 (3) and N3—HN3 = 0.87 (4) Å]. Their isotropic displacement parameters were refined with Uiso(H) = 1.2Ueq(N) for the NH and NH2 groups and Uiso(H) = 1.5Ueq(O) for hydroxyl group. The remaining H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C—H = 0.93 Å, and Uiso(H) = 1.2Ueq(C).

Structure description top

Thiosemicarbazones constitute an important class of N,S donor ligands due to their propensity to react with a wide range of metals (Casas et al., 2000). Thiosemicarbazones exhibit various biological activities and have therefore attracted considerable pharmaceutical interest (Maccioni et al., 2003; Ferrari et al., 2000). We here report the crystal structure of the title compound (I).

The title molecule (I) shown in Fig. 1 is almost planar with the maximum deviations of -0.127 (3) Å for N2 and 0.135 (5) Å for N3. All bond lengths and angles are normal (Allen et al., 1987). In each independent molecule, there are intramolecular N—H···N and O—H···N hydrogen bonds, generating the S(5) and S(6) ring motifs, respectively (Table 1, Fig. 2).

In the crystal structure, adjacent molecules are linked by N—H···S hydrogen bonds, forming R22(8) dimers (Bernstein et al., 1995) (Table 1, Fig. 2).

For background on the biological activities and pharmaceutical properties of thiosemicarbazones and their derivatives, see: Casas et al. (2000); Ferrari et al. (2000); Maccioni et al. (2003). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. View of the title molecule, showing displacement ellipsoids for non-H atoms drawn at the 50% probability level.
[Figure 2] Fig. 2. View of the hydrogen bonding interactions of (I), showing dimer formation by R22(8) ring motif within chains.
5-Bromo-2-hydroxybenzaldehyde thiosemicarbazone top
Crystal data top
C8H8BrN3OSF(000) = 544
Mr = 274.14Dx = 1.765 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 17874 reflections
a = 4.4564 (2) Åθ = 1.5–26.1°
b = 8.3515 (3) ŵ = 4.16 mm−1
c = 27.7153 (14) ÅT = 296 K
V = 1031.50 (8) Å3Prism, colourless
Z = 40.13 × 0.09 × 0.05 mm
Data collection top
Stoe IPDS II
diffractometer		1934 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1782 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.037
Detector resolution: 6.67 pixels mm-1θmax = 25.6°, θmin = 2.6°
ω scansh = −5→5
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		k = −10→10
Tmin = 0.614, Tmax = 0.819l = −33→33
9532 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.063 w = 1/[σ2(Fo2) + (0.0281P)2 + 0.5533P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
1934 reflectionsΔρmax = 0.54 e Å−3
144 parametersΔρmin = −0.29 e Å−3
4 restraintsAbsolute structure: Flack (1983), with 744 Freidel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.477 (11)
Crystal data top
C8H8BrN3OSV = 1031.50 (8) Å3
Mr = 274.14Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 4.4564 (2) ŵ = 4.16 mm−1
b = 8.3515 (3) ÅT = 296 K
c = 27.7153 (14) Å0.13 × 0.09 × 0.05 mm
Data collection top
Stoe IPDS II
diffractometer		1934 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		1782 reflections with I > 2σ(I)
Tmin = 0.614, Tmax = 0.819Rint = 0.037
9532 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.063Δρmax = 0.54 e Å−3
S = 1.04Δρmin = −0.29 e Å−3
1934 reflectionsAbsolute structure: Flack (1983), with 744 Freidel pairs
144 parametersAbsolute structure parameter: 0.477 (11)
4 restraints
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.80875 (10)−0.32853 (5)0.06313 (1)0.0606 (1)
S1−0.5577 (2)0.35791 (11)0.26412 (3)0.0517 (3)
O10.2883 (6)0.3331 (3)0.08454 (10)0.0596 (9)
N1−0.0227 (7)0.2201 (3)0.16022 (10)0.0407 (9)
N2−0.2226 (8)0.2237 (3)0.19824 (9)0.0408 (9)
N3−0.2703 (13)0.4940 (4)0.19194 (14)0.0786 (16)
C10.4380 (8)−0.0920 (4)0.10693 (12)0.0416 (10)
C20.6401 (7)−0.1207 (4)0.07038 (11)0.0420 (10)
C30.7260 (8)0.0001 (5)0.03956 (13)0.0486 (11)
C40.6033 (8)0.1505 (5)0.04464 (12)0.0485 (11)
C50.3981 (7)0.1819 (5)0.08111 (11)0.0418 (10)
C60.3119 (8)0.0589 (4)0.11293 (11)0.0382 (9)
C70.0966 (8)0.0836 (4)0.15148 (11)0.0389 (10)
C8−0.3365 (8)0.3610 (4)0.21496 (11)0.0416 (10)
H10.38530−0.174500.127800.0500*
HN2−0.323 (12)0.587 (3)0.2025 (16)0.089 (16)*
HN1−0.260 (9)0.135 (3)0.2114 (12)0.050 (11)*
H30.86620−0.019800.015400.0580*
HO10.169 (8)0.334 (6)0.1064 (12)0.071 (14)*
H40.658400.231800.023500.0580*
HN3−0.144 (9)0.486 (5)0.1681 (12)0.071 (14)*
H70.04290−0.003200.170600.0470*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0606 (2)0.0575 (2)0.0638 (2)0.0057 (2)0.0074 (2)−0.0153 (2)
S10.0657 (6)0.0400 (5)0.0495 (5)−0.0007 (5)0.0199 (4)−0.0055 (4)
O10.0646 (16)0.0493 (14)0.0649 (15)0.007 (2)0.0180 (14)0.0102 (14)
N10.0400 (16)0.0458 (16)0.0364 (13)−0.0052 (13)0.0067 (12)−0.0039 (11)
N20.0436 (18)0.0372 (14)0.0415 (14)−0.0028 (13)0.0117 (13)−0.0030 (11)
N30.122 (4)0.0397 (17)0.074 (2)0.011 (2)0.051 (3)0.0063 (17)
C10.0408 (17)0.0454 (19)0.0387 (17)−0.0065 (16)0.0004 (15)−0.0037 (15)
C20.0341 (18)0.0532 (19)0.0386 (16)−0.0029 (14)0.0002 (13)−0.0098 (14)
C30.038 (2)0.065 (2)0.0428 (17)−0.0032 (18)0.0111 (15)0.0010 (16)
C40.0427 (19)0.062 (2)0.0407 (16)−0.0058 (19)0.0012 (13)0.0095 (17)
C50.0368 (17)0.0475 (19)0.0411 (15)−0.0069 (17)0.0005 (12)0.0020 (15)
C60.0320 (14)0.0477 (18)0.0350 (15)−0.0045 (17)−0.0008 (15)−0.0019 (13)
C70.0374 (19)0.0462 (18)0.0332 (15)−0.0033 (15)0.0027 (13)−0.0010 (14)
C80.0465 (18)0.0381 (18)0.0402 (15)−0.0006 (17)0.0002 (15)−0.0030 (13)
Geometric parameters (Å, º) top
Br1—C21.902 (3)C1—C21.377 (5)
S1—C81.682 (3)C1—C61.390 (5)
O1—C51.358 (5)C2—C31.376 (5)
O1—HO10.81 (3)C3—C41.377 (6)
N1—N21.380 (4)C4—C51.388 (5)
N1—C71.281 (4)C5—C61.407 (5)
N2—C81.337 (4)C6—C71.451 (5)
N3—C81.315 (5)C1—H10.9300
N2—HN10.84 (3)C3—H30.9300
N3—HN20.86 (3)C4—H40.9300
N3—HN30.87 (4)C7—H70.9300
C5—O1—HO1107 (4)O1—C5—C4117.7 (3)
N2—N1—C7115.6 (3)C5—C6—C7122.6 (3)
N1—N2—C8121.9 (3)C1—C6—C5118.5 (3)
C8—N2—HN1122 (2)C1—C6—C7119.0 (3)
N1—N2—HN1116 (2)N1—C7—C6122.7 (3)
HN2—N3—HN3120 (4)N2—C8—N3118.1 (3)
C8—N3—HN2122 (3)S1—C8—N2119.4 (3)
C8—N3—HN3117 (3)S1—C8—N3122.5 (3)
C2—C1—C6120.7 (3)C2—C1—H1120.00
Br1—C2—C3119.6 (3)C6—C1—H1120.00
C1—C2—C3120.7 (3)C2—C3—H3120.00
Br1—C2—C1119.7 (2)C4—C3—H3120.00
C2—C3—C4119.7 (3)C3—C4—H4120.00
C3—C4—C5120.6 (4)C5—C4—H4120.00
C4—C5—C6119.9 (4)N1—C7—H7119.00
O1—C5—C6122.5 (3)C6—C7—H7119.00
C7—N1—N2—C8172.0 (3)C2—C3—C4—C51.2 (5)
N2—N1—C7—C6−179.8 (3)C3—C4—C5—O1179.2 (3)
N1—N2—C8—S1−175.2 (3)C3—C4—C5—C6−0.6 (5)
N1—N2—C8—N34.9 (5)C4—C5—C6—C10.4 (5)
C2—C1—C6—C7179.1 (3)O1—C5—C6—C1−179.5 (3)
C2—C1—C6—C5−0.7 (5)O1—C5—C6—C70.7 (5)
C6—C1—C2—Br1180.0 (3)C4—C5—C6—C7−179.4 (3)
C6—C1—C2—C31.2 (5)C1—C6—C7—N1177.9 (3)
Br1—C2—C3—C4179.8 (3)C5—C6—C7—N1−2.3 (5)
C1—C2—C3—C4−1.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—HO1···N10.81 (3)1.97 (4)2.685 (4)149 (5)
N3—HN3···N10.87 (4)2.30 (4)2.688 (5)107 (3)
N2—HN1···S1i0.84 (3)2.55 (3)3.373 (3)168 (3)
N3—HN2···S1ii0.86 (3)2.50 (3)3.363 (4)176 (6)
Symmetry codes: (i) −x−1, y−1/2, −z+1/2; (ii) −x−1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC8H8BrN3OS
Mr274.14
Crystal system, space groupOrthorhombic, P212121
Temperature (K)296
a, b, c (Å)4.4564 (2), 8.3515 (3), 27.7153 (14)
V (Å3)1031.50 (8)
Z4
Radiation typeMo Kα
µ (mm−1)4.16
Crystal size (mm)0.13 × 0.09 × 0.05
Data collection
DiffractometerStoe IPDS II
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.614, 0.819
No. of measured, independent and
observed [I > 2σ(I)] reflections		9532, 1934, 1782
Rint0.037
(sin θ/λ)max (Å−1)0.608
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.063, 1.04
No. of reflections1934
No. of parameters144
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.54, −0.29
Absolute structureFlack (1983), with 744 Freidel pairs
Absolute structure parameter0.477 (11)

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—HO1···N10.81 (3)1.97 (4)2.685 (4)149 (5)
N3—HN3···N10.87 (4)2.30 (4)2.688 (5)107 (3)
N2—HN1···S1i0.84 (3)2.55 (3)3.373 (3)168 (3)
N3—HN2···S1ii0.86 (3)2.50 (3)3.363 (4)176 (6)
Symmetry codes: (i) −x−1, y−1/2, −z+1/2; (ii) −x−1, y+1/2, −z+1/2.
 

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant F.279 of the University Research Fund). HK thanks Payame Noor University (PNU) for financial support of this work. RK thanks the Science and Research Branch of Islamic Azad University of Tehran.

References

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ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2999
https://doi.org/10.1107/S1600536810043357
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