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

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ISSN: 2056-9890

4-(2-Hy­dr­oxy­phen­yl)-3,5-di­thia­hepta­ne­dioic acid

aDepartment of Physics, Kandaswami Kandar's College, Velur, Namakkal 638 182, India, bInstitute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentska 573, 532 10 Pardubice, Czech Republic, cDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and dCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 6 May 2013; accepted 9 May 2013; online 15 May 2013)

In the crystal of the title compound, C11H12O5S2, mol­ecules are linked by O—H⋯O hydrogen bonds and C—H⋯O inter­actions, forming a three-dimensional network.

Related literature

For related structures, see: Guo et al. (2010[Guo, Y.-N., Xu, G.-F., Gamez, P., Zhao, L., Lin, S.-Y., Deng, R., Tang, J.-K. & Zhang, H.-J. (2010). J. Am. Chem. Soc. 132, 8538-8539.]); Yu et al. (2010[Yu, G.-M., Zhao, L., Guo, Y.-N., Xu, G.-F., Zou, L.-F., Tang, J.-K. & Li, Y.-H. (2010). J. Mol. Struct. 982, 139-144.]); Rollas & Kucukguzel (2007[Rollas, S. & Kucukguzel, S. G. (2007). Molecules, 12, 1910-1939.]). 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. 1-19.]). 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
  • C11H12O5S2

  • Mr = 288.33

  • Triclinic, [P \overline 1]

  • a = 7.2465 (1) Å

  • b = 7.6533 (1) Å

  • c = 12.0141 (2) Å

  • α = 101.094 (2)°

  • β = 99.129 (1)°

  • γ = 102.390 (2)°

  • V = 624.57 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.44 mm−1

  • T = 293 K

  • 0.20 × 0.18 × 0.17 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.916, Tmax = 0.929

  • 2746 measured reflections

  • 2180 independent reflections

  • 1918 reflections with I > 2σ(I)

  • Rint = 0.008

Refinement
  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.073

  • S = 1.06

  • 2180 reflections

  • 175 parameters

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

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯O3i 0.93 2.58 3.395 (2) 146
O1—H1⋯O4ii 0.75 (2) 1.97 (2) 2.7143 (19) 173 (3)
C8—H8B⋯O5iii 0.97 2.53 3.429 (2) 154
O2—H2A⋯O1iv 0.81 (3) 1.92 (3) 2.706 (2) 163 (2)
O5—H5A⋯O3v 0.79 (3) 1.97 (3) 2.7459 (19) 165 (3)
Symmetry codes: (i) x+1, y+1, z; (ii) -x+2, -y+1, -z; (iii) x, y+1, z; (iv) -x+1, -y+1, -z; (v) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

In coordination chemistry, the acylhydrazone ligands attracted the chemists due to their potential behaviour in magnetochemistry (Yu et al., 2010; Guo et al., 2010). The choice of N-acylhydrazonyl derivatives was suggested by publications indicating that compounds with such groups might have anti-tumoural activities (Rollas & Kucukguzel 2007). Against this background and to ascertain the molecular structure of title compound, the crystallographic study has been carried out.

The ORTEP plot of the molecule is shown in Fig. 1. The bond lengths involving the sulfur atoms in methyl sulfanyl groups [S1—C7=] 1.821 (2) Å, [S1—C10=] 1.799 (2) Å, [S2—C7=] 1.830 (2) Å and [S2—C8=] 1.794 (2) Å are comparable with the standard values of 1.82 Å reported in the literature (Allen et al., 1987).

The crystal structure is stabilized by C—H···O and O—H···O types of intra and intermolecular interactions which form a three demensional network shown in Fig. 2. The intermolecular O1—H1···O4 and O2—H2A···O1 hydrogen bonds form two different R22(18) dimers. The molecules at O5 (x, y, z) and O3 (-x + 1, -y, -z) are linked through an intermolecular O5—H5A···O3 hydrogen bond into cyclic centrosymmetric R22(20) dimer (Bernstein et al., 1995).

Related literature top

For related structures, see: Guo et al. (2010); Yu et al. (2010); Rollas & Kucukguzel (2007). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of salicylaldehyde and freshly distilled thioglycollic acid in 1:1.2 mole ratio was dissolved by heating on a water bath and let stand two days. The product was washed with water and recrystallized.

Refinement top

H atoms bonded to O were isotropically refined and the other H atoms were positioned geometrically (C—H=0.93–0.98 Å) and allowed to ride on their parent atoms, with 1.2 Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atomic numbering and displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The packing of the molecules viewed down c axis.
4-(2-Hydroxyphenyl)-3,5-dithiaheptanedioic acid top
Crystal data top
C11H12O5S2Z = 2
Mr = 288.33F(000) = 300
Triclinic, P1Dx = 1.533 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2465 (1) ÅCell parameters from 1918 reflections
b = 7.6533 (1) Åθ = 2.8–25.0°
c = 12.0141 (2) ŵ = 0.44 mm1
α = 101.094 (2)°T = 293 K
β = 99.129 (1)°Block, white
γ = 102.390 (2)°0.20 × 0.18 × 0.17 mm
V = 624.57 (2) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
2180 independent reflections
Radiation source: fine-focus sealed tube1918 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.008
ω and ϕ scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 18
Tmin = 0.916, Tmax = 0.929k = 99
2746 measured reflectionsl = 1414
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0361P)2 + 0.2534P]
where P = (Fo2 + 2Fc2)/3
2180 reflections(Δ/σ)max < 0.001
175 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C11H12O5S2γ = 102.390 (2)°
Mr = 288.33V = 624.57 (2) Å3
Triclinic, P1Z = 2
a = 7.2465 (1) ÅMo Kα radiation
b = 7.6533 (1) ŵ = 0.44 mm1
c = 12.0141 (2) ÅT = 293 K
α = 101.094 (2)°0.20 × 0.18 × 0.17 mm
β = 99.129 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
2180 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
1918 reflections with I > 2σ(I)
Tmin = 0.916, Tmax = 0.929Rint = 0.008
2746 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.073H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.24 e Å3
2180 reflectionsΔρmin = 0.21 e Å3
175 parameters
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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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
S11.00303 (6)0.36671 (6)0.31104 (4)0.03515 (13)
S20.67356 (6)0.52625 (6)0.35266 (4)0.03286 (13)
O10.9831 (2)0.7027 (2)0.09620 (11)0.0426 (3)
H11.038 (4)0.747 (3)0.057 (2)0.056 (7)*
O20.3103 (2)0.5269 (2)0.07080 (14)0.0557 (4)
H2A0.241 (4)0.450 (3)0.016 (2)0.059 (7)*
O30.4267 (2)0.29754 (18)0.11941 (11)0.0462 (3)
O40.8498 (3)0.1453 (2)0.06126 (12)0.0639 (5)
O50.6463 (2)0.08304 (19)0.10180 (13)0.0520 (4)
H5A0.628 (4)0.128 (3)0.035 (2)0.066 (8)*
C11.0698 (2)0.7921 (2)0.20917 (14)0.0303 (4)
C21.2097 (3)0.9569 (2)0.23501 (17)0.0395 (4)
H21.24771.00760.17530.047*
C31.2930 (3)1.0461 (3)0.34859 (18)0.0443 (5)
H31.38691.15690.36550.053*
C41.2370 (3)0.9711 (3)0.43746 (17)0.0476 (5)
H41.29251.03130.51430.057*
C51.0979 (3)0.8059 (3)0.41159 (16)0.0411 (4)
H51.06120.75570.47170.049*
C61.0119 (2)0.7133 (2)0.29760 (14)0.0281 (3)
C70.8675 (2)0.5283 (2)0.27182 (14)0.0278 (3)
H70.81090.49010.18850.033*
C80.5047 (2)0.5942 (2)0.25420 (16)0.0373 (4)
H8A0.40380.62290.29320.045*
H8B0.57100.70630.23620.045*
C90.4115 (2)0.4540 (2)0.14220 (16)0.0354 (4)
C100.8202 (3)0.1531 (2)0.25863 (14)0.0335 (4)
H10A0.86000.06270.29710.040*
H10B0.70170.17140.28110.040*
C110.7775 (3)0.0751 (2)0.12984 (15)0.0357 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0314 (2)0.0288 (2)0.0430 (3)0.00619 (17)0.00384 (18)0.00810 (18)
S20.0303 (2)0.0346 (2)0.0324 (2)0.00405 (17)0.00923 (17)0.00719 (17)
O10.0395 (7)0.0544 (8)0.0304 (7)0.0001 (6)0.0077 (6)0.0144 (6)
O20.0534 (9)0.0514 (9)0.0531 (9)0.0128 (7)0.0113 (7)0.0093 (7)
O30.0524 (8)0.0349 (7)0.0429 (7)0.0075 (6)0.0017 (6)0.0002 (6)
O40.0885 (12)0.0598 (9)0.0378 (8)0.0036 (8)0.0236 (8)0.0149 (7)
O50.0655 (10)0.0373 (8)0.0396 (8)0.0047 (7)0.0083 (7)0.0009 (6)
C10.0290 (8)0.0311 (8)0.0333 (9)0.0102 (7)0.0081 (7)0.0091 (7)
C20.0379 (10)0.0351 (9)0.0494 (11)0.0060 (8)0.0153 (8)0.0174 (8)
C30.0370 (10)0.0299 (9)0.0593 (12)0.0030 (8)0.0113 (9)0.0062 (8)
C40.0450 (11)0.0421 (11)0.0408 (10)0.0055 (9)0.0040 (9)0.0027 (8)
C50.0449 (10)0.0406 (10)0.0315 (9)0.0016 (8)0.0081 (8)0.0070 (8)
C60.0253 (8)0.0258 (8)0.0324 (8)0.0047 (6)0.0067 (6)0.0065 (6)
C70.0283 (8)0.0261 (8)0.0276 (8)0.0039 (7)0.0059 (6)0.0063 (6)
C80.0313 (9)0.0318 (9)0.0459 (10)0.0087 (7)0.0050 (8)0.0038 (8)
C90.0272 (8)0.0358 (10)0.0405 (9)0.0028 (7)0.0070 (7)0.0086 (8)
C100.0400 (10)0.0255 (8)0.0346 (9)0.0043 (7)0.0115 (7)0.0079 (7)
C110.0422 (10)0.0296 (9)0.0369 (9)0.0107 (8)0.0103 (8)0.0085 (7)
Geometric parameters (Å, º) top
S1—C101.7984 (17)C2—H20.9300
S1—C71.8207 (16)C3—C41.382 (3)
S2—C81.7940 (18)C3—H30.9300
S2—C71.8296 (16)C4—C51.383 (3)
O1—C11.376 (2)C4—H40.9300
O1—H10.75 (2)C5—C61.390 (2)
O2—C91.321 (2)C5—H50.9300
O2—H2A0.81 (3)C6—C71.513 (2)
O3—C91.209 (2)C7—H70.9800
O4—C111.195 (2)C8—C91.504 (2)
O5—C111.315 (2)C8—H8A0.9700
O5—H5A0.79 (3)C8—H8B0.9700
C1—C21.384 (2)C10—C111.503 (2)
C1—C61.396 (2)C10—H10A0.9700
C2—C31.377 (3)C10—H10B0.9700
C10—S1—C7100.79 (8)C6—C7—S2113.81 (11)
C8—S2—C799.46 (8)S1—C7—S2109.04 (8)
C1—O1—H1108.6 (19)C6—C7—H7109.2
C9—O2—H2A112.0 (18)S1—C7—H7109.2
C11—O5—H5A110.7 (19)S2—C7—H7109.2
O1—C1—C2121.08 (15)C9—C8—S2115.36 (12)
O1—C1—C6118.31 (15)C9—C8—H8A108.4
C2—C1—C6120.61 (16)S2—C8—H8A108.4
C3—C2—C1120.38 (17)C9—C8—H8B108.4
C3—C2—H2119.8S2—C8—H8B108.4
C1—C2—H2119.8H8A—C8—H8B107.5
C2—C3—C4119.95 (17)O3—C9—O2124.33 (17)
C2—C3—H3120.0O3—C9—C8125.59 (17)
C4—C3—H3120.0O2—C9—C8110.08 (16)
C3—C4—C5119.65 (18)C11—C10—S1115.58 (12)
C3—C4—H4120.2C11—C10—H10A108.4
C5—C4—H4120.2S1—C10—H10A108.4
C4—C5—C6121.41 (17)C11—C10—H10B108.4
C4—C5—H5119.3S1—C10—H10B108.4
C6—C5—H5119.3H10A—C10—H10B107.4
C5—C6—C1117.99 (15)O4—C11—O5123.98 (18)
C5—C6—C7120.20 (15)O4—C11—C10125.68 (17)
C1—C6—C7121.74 (14)O5—C11—C10110.34 (15)
C6—C7—S1106.43 (11)
O1—C1—C2—C3178.98 (17)C5—C6—C7—S251.35 (19)
C6—C1—C2—C30.4 (3)C1—C6—C7—S2131.74 (14)
C1—C2—C3—C40.0 (3)C10—S1—C7—C6172.98 (11)
C2—C3—C4—C50.3 (3)C10—S1—C7—S263.85 (9)
C3—C4—C5—C60.3 (3)C8—S2—C7—C688.30 (13)
C4—C5—C6—C10.1 (3)C8—S2—C7—S1153.06 (9)
C4—C5—C6—C7176.96 (17)C7—S2—C8—C969.48 (14)
O1—C1—C6—C5178.99 (16)S2—C8—C9—O37.7 (2)
C2—C1—C6—C50.4 (2)S2—C8—C9—O2171.86 (13)
O1—C1—C6—C74.0 (2)C7—S1—C10—C1177.55 (14)
C2—C1—C6—C7176.55 (15)S1—C10—C11—O42.3 (3)
C5—C6—C7—S168.78 (18)S1—C10—C11—O5178.19 (13)
C1—C6—C7—S1108.13 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O10.982.392.846 (2)108
C2—H2···O3i0.932.583.395 (2)146
O1—H1···O4ii0.75 (2)1.97 (2)2.7143 (19)173 (3)
C8—H8B···O5iii0.972.533.429 (2)154
O2—H2A···O1iv0.81 (3)1.92 (3)2.706 (2)163 (2)
O5—H5A···O3v0.79 (3)1.97 (3)2.7459 (19)165 (3)
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y+1, z; (iii) x, y+1, z; (iv) x+1, y+1, z; (v) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC11H12O5S2
Mr288.33
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.2465 (1), 7.6533 (1), 12.0141 (2)
α, β, γ (°)101.094 (2), 99.129 (1), 102.390 (2)
V3)624.57 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.44
Crystal size (mm)0.20 × 0.18 × 0.17
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.916, 0.929
No. of measured, independent and
observed [I > 2σ(I)] reflections
2746, 2180, 1918
Rint0.008
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.073, 1.06
No. of reflections2180
No. of parameters175
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.24, 0.21

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O3i0.932.583.395 (2)146.1
O1—H1···O4ii0.75 (2)1.97 (2)2.7143 (19)173 (3)
C8—H8B···O5iii0.972.533.429 (2)153.8
O2—H2A···O1iv0.81 (3)1.92 (3)2.706 (2)163 (2)
O5—H5A···O3v0.79 (3)1.97 (3)2.7459 (19)165 (3)
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y+1, z; (iii) x, y+1, z; (iv) x+1, y+1, z; (v) x+1, y, z.
 

Acknowledgements

The authors thank the TBI Consultancy, University of Madras, India, for the data collection. KR also thanks the management of Kandaswami Kandars College, Velur, Namakkal, Tamilnadu, India.

References

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