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

Ravichandran, K.; Manikannan, R.; Muthusubramanian, S.; Ramesh, P.; Ponnuswamy, M.N.

doi:10.1107/S1600536813012737

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o893

doi:10.1107/S1600536813012737

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

K. Ravichandran,^a R. Manikannan,^b S. Muthusubramanian,^c P. Ramesh ^d and M. N. Ponnuswamy ^d ^*

^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 ); 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

Crystal data

C₁₁H₁₂O₅S₂
M_r = 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 ) T_min = 0.916, T_max = 0.929
2746 measured reflections
2180 independent reflections
1918 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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⋯O1^iv	0.81 (3)	1.92 (3)	2.706 (2)	163 (2)
O5—H5A⋯O3^v	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); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813012737/bt6906sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813012737/bt6906Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813012737/bt6906Isup3.cml

checkCIF report

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.

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

	Fig. 1. The molecular structure of the title compound, showing the atomic numbering and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The packing of the molecules viewed down c axis.

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

Crystal data top

C₁₁H₁₂O₅S₂	Z = 2
M_r = 288.33	F(000) = 300
Triclinic, P1	D_x = 1.533 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2465 (1) Å	Cell parameters from 1918 reflections
b = 7.6533 (1) Å	θ = 2.8–25.0°
c = 12.0141 (2) Å	µ = 0.44 mm⁻¹
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 tube	1918 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.008
ω and ϕ scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −1→8
T_min = 0.916, T_max = 0.929	k = −9→9
2746 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0361P)² + 0.2534P] where P = (F_o² + 2F_c²)/3
2180 reflections	(Δ/σ)_max < 0.001
175 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₁H₁₂O₅S₂	γ = 102.390 (2)°
M_r = 288.33	V = 624.57 (2) Å³
Triclinic, P1	Z = 2
a = 7.2465 (1) Å	Mo Kα radiation
b = 7.6533 (1) Å	µ = 0.44 mm⁻¹
c = 12.0141 (2) Å	T = 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)
T_min = 0.916, T_max = 0.929	R_int = 0.008
2746 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.24 e Å⁻³
2180 reflections	Δρ_min = −0.21 e Å⁻³
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

	x	y	z	U_iso*/U_eq
S1	1.00303 (6)	0.36671 (6)	0.31104 (4)	0.03515 (13)
S2	0.67356 (6)	0.52625 (6)	0.35266 (4)	0.03286 (13)
O1	0.9831 (2)	0.7027 (2)	0.09620 (11)	0.0426 (3)
H1	1.038 (4)	0.747 (3)	0.057 (2)	0.056 (7)*
O2	0.3103 (2)	0.5269 (2)	0.07080 (14)	0.0557 (4)
H2A	0.241 (4)	0.450 (3)	0.016 (2)	0.059 (7)*
O3	0.4267 (2)	0.29754 (18)	0.11941 (11)	0.0462 (3)
O4	0.8498 (3)	0.1453 (2)	0.06126 (12)	0.0639 (5)
O5	0.6463 (2)	−0.08304 (19)	0.10180 (13)	0.0520 (4)
H5A	0.628 (4)	−0.128 (3)	0.035 (2)	0.066 (8)*
C1	1.0698 (2)	0.7921 (2)	0.20917 (14)	0.0303 (4)
C2	1.2097 (3)	0.9569 (2)	0.23501 (17)	0.0395 (4)
H2	1.2477	1.0076	0.1753	0.047*
C3	1.2930 (3)	1.0461 (3)	0.34859 (18)	0.0443 (5)
H3	1.3869	1.1569	0.3655	0.053*
C4	1.2370 (3)	0.9711 (3)	0.43746 (17)	0.0476 (5)
H4	1.2925	1.0313	0.5143	0.057*
C5	1.0979 (3)	0.8059 (3)	0.41159 (16)	0.0411 (4)
H5	1.0612	0.7557	0.4717	0.049*
C6	1.0119 (2)	0.7133 (2)	0.29760 (14)	0.0281 (3)
C7	0.8675 (2)	0.5283 (2)	0.27182 (14)	0.0278 (3)
H7	0.8109	0.4901	0.1885	0.033*
C8	0.5047 (2)	0.5942 (2)	0.25420 (16)	0.0373 (4)
H8A	0.4038	0.6229	0.2932	0.045*
H8B	0.5710	0.7063	0.2362	0.045*
C9	0.4115 (2)	0.4540 (2)	0.14220 (16)	0.0354 (4)
C10	0.8202 (3)	0.1531 (2)	0.25863 (14)	0.0335 (4)
H10A	0.8600	0.0627	0.2971	0.040*
H10B	0.7017	0.1714	0.2811	0.040*
C11	0.7775 (3)	0.0751 (2)	0.12984 (15)	0.0357 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0314 (2)	0.0288 (2)	0.0430 (3)	0.00619 (17)	0.00384 (18)	0.00810 (18)
S2	0.0303 (2)	0.0346 (2)	0.0324 (2)	0.00405 (17)	0.00923 (17)	0.00719 (17)
O1	0.0395 (7)	0.0544 (8)	0.0304 (7)	0.0001 (6)	0.0077 (6)	0.0144 (6)
O2	0.0534 (9)	0.0514 (9)	0.0531 (9)	0.0128 (7)	−0.0113 (7)	0.0093 (7)
O3	0.0524 (8)	0.0349 (7)	0.0429 (7)	0.0075 (6)	0.0017 (6)	0.0002 (6)
O4	0.0885 (12)	0.0598 (9)	0.0378 (8)	−0.0036 (8)	0.0236 (8)	0.0149 (7)
O5	0.0655 (10)	0.0373 (8)	0.0396 (8)	−0.0047 (7)	0.0083 (7)	−0.0009 (6)
C1	0.0290 (8)	0.0311 (8)	0.0333 (9)	0.0102 (7)	0.0081 (7)	0.0091 (7)
C2	0.0379 (10)	0.0351 (9)	0.0494 (11)	0.0060 (8)	0.0153 (8)	0.0174 (8)
C3	0.0370 (10)	0.0299 (9)	0.0593 (12)	−0.0030 (8)	0.0113 (9)	0.0062 (8)
C4	0.0450 (11)	0.0421 (11)	0.0408 (10)	−0.0055 (9)	0.0040 (9)	−0.0027 (8)
C5	0.0449 (10)	0.0406 (10)	0.0315 (9)	−0.0016 (8)	0.0081 (8)	0.0070 (8)
C6	0.0253 (8)	0.0258 (8)	0.0324 (8)	0.0047 (6)	0.0067 (6)	0.0065 (6)
C7	0.0283 (8)	0.0261 (8)	0.0276 (8)	0.0039 (7)	0.0059 (6)	0.0063 (6)
C8	0.0313 (9)	0.0318 (9)	0.0459 (10)	0.0087 (7)	0.0050 (8)	0.0038 (8)
C9	0.0272 (8)	0.0358 (10)	0.0405 (9)	0.0028 (7)	0.0070 (7)	0.0086 (8)
C10	0.0400 (10)	0.0255 (8)	0.0346 (9)	0.0043 (7)	0.0115 (7)	0.0079 (7)
C11	0.0422 (10)	0.0296 (9)	0.0369 (9)	0.0107 (8)	0.0103 (8)	0.0085 (7)

Geometric parameters (Å, º) top

S1—C10	1.7984 (17)	C2—H2	0.9300
S1—C7	1.8207 (16)	C3—C4	1.382 (3)
S2—C8	1.7940 (18)	C3—H3	0.9300
S2—C7	1.8296 (16)	C4—C5	1.383 (3)
O1—C1	1.376 (2)	C4—H4	0.9300
O1—H1	0.75 (2)	C5—C6	1.390 (2)
O2—C9	1.321 (2)	C5—H5	0.9300
O2—H2A	0.81 (3)	C6—C7	1.513 (2)
O3—C9	1.209 (2)	C7—H7	0.9800
O4—C11	1.195 (2)	C8—C9	1.504 (2)
O5—C11	1.315 (2)	C8—H8A	0.9700
O5—H5A	0.79 (3)	C8—H8B	0.9700
C1—C2	1.384 (2)	C10—C11	1.503 (2)
C1—C6	1.396 (2)	C10—H10A	0.9700
C2—C3	1.377 (3)	C10—H10B	0.9700

C10—S1—C7	100.79 (8)	C6—C7—S2	113.81 (11)
C8—S2—C7	99.46 (8)	S1—C7—S2	109.04 (8)
C1—O1—H1	108.6 (19)	C6—C7—H7	109.2
C9—O2—H2A	112.0 (18)	S1—C7—H7	109.2
C11—O5—H5A	110.7 (19)	S2—C7—H7	109.2
O1—C1—C2	121.08 (15)	C9—C8—S2	115.36 (12)
O1—C1—C6	118.31 (15)	C9—C8—H8A	108.4
C2—C1—C6	120.61 (16)	S2—C8—H8A	108.4
C3—C2—C1	120.38 (17)	C9—C8—H8B	108.4
C3—C2—H2	119.8	S2—C8—H8B	108.4
C1—C2—H2	119.8	H8A—C8—H8B	107.5
C2—C3—C4	119.95 (17)	O3—C9—O2	124.33 (17)
C2—C3—H3	120.0	O3—C9—C8	125.59 (17)
C4—C3—H3	120.0	O2—C9—C8	110.08 (16)
C3—C4—C5	119.65 (18)	C11—C10—S1	115.58 (12)
C3—C4—H4	120.2	C11—C10—H10A	108.4
C5—C4—H4	120.2	S1—C10—H10A	108.4
C4—C5—C6	121.41 (17)	C11—C10—H10B	108.4
C4—C5—H5	119.3	S1—C10—H10B	108.4
C6—C5—H5	119.3	H10A—C10—H10B	107.4
C5—C6—C1	117.99 (15)	O4—C11—O5	123.98 (18)
C5—C6—C7	120.20 (15)	O4—C11—C10	125.68 (17)
C1—C6—C7	121.74 (14)	O5—C11—C10	110.34 (15)
C6—C7—S1	106.43 (11)

O1—C1—C2—C3	178.98 (17)	C5—C6—C7—S2	51.35 (19)
C6—C1—C2—C3	−0.4 (3)	C1—C6—C7—S2	−131.74 (14)
C1—C2—C3—C4	0.0 (3)	C10—S1—C7—C6	−172.98 (11)
C2—C3—C4—C5	0.3 (3)	C10—S1—C7—S2	63.85 (9)
C3—C4—C5—C6	−0.3 (3)	C8—S2—C7—C6	88.30 (13)
C4—C5—C6—C1	−0.1 (3)	C8—S2—C7—S1	−153.06 (9)
C4—C5—C6—C7	176.96 (17)	C7—S2—C8—C9	69.48 (14)
O1—C1—C6—C5	−178.99 (16)	S2—C8—C9—O3	7.7 (2)
C2—C1—C6—C5	0.4 (2)	S2—C8—C9—O2	−171.86 (13)
O1—C1—C6—C7	4.0 (2)	C7—S1—C10—C11	77.55 (14)
C2—C1—C6—C7	−176.55 (15)	S1—C10—C11—O4	−2.3 (3)
C5—C6—C7—S1	−68.78 (18)	S1—C10—C11—O5	178.19 (13)
C1—C6—C7—S1	108.13 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.98	2.39	2.846 (2)	108
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···O1^iv	0.81 (3)	1.92 (3)	2.706 (2)	163 (2)
O5—H5A···O3^v	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.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂O₅S₂
M_r	288.33
Crystal system, space group	Triclinic, 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)
V (Å³)	624.57 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.916, 0.929
No. of measured, independent and observed [I > 2σ(I)] reflections	2746, 2180, 1918
R_int	0.008
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.073, 1.06
No. of reflections	2180
No. of parameters	175
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱ	0.93	2.58	3.395 (2)	146.1
O1—H1···O4ⁱⁱ	0.75 (2)	1.97 (2)	2.7143 (19)	173 (3)
C8—H8B···O5ⁱⁱⁱ	0.97	2.53	3.429 (2)	153.8
O2—H2A···O1^iv	0.81 (3)	1.92 (3)	2.706 (2)	163 (2)
O5—H5A···O3^v	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.

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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