Crystal structure of (Z)-2-hy­droxy-4-methyl-N′-(4-oxo-1,3-thia­zolidin-2-yl­idene)benzohydrazide trihydrate

Li, P.; Kang, Z.; Fan, X.; Jin, L.

doi:10.1107/S1600536814023356

organic compounds

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Volume 70| Part 11| November 2014| Page o1199

doi:10.1107/S1600536814023356

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Crystal structure of (Z)-2-hydroxy-4-methyl-N′-(4-oxo-1,3-thiazolidin-2-ylidene)benzohydrazide trihydrate

Peijuan Li,^a Zizhen Kang,^a Xin Fan ^a and Longfei Jin ^a ^*

^aCollege of Chemistry and Material Science, South-Central University for Nationalities, Wuhan 430074, People's Republic of China
^*Correspondence e-mail: longfei.jin@yahoo.com

Edited by A. J. Lough, University of Toronto, Canada (Received 8 October 2014; accepted 23 October 2014; online 29 October 2014)

In the title compound, C₁₁H₁₁N₃O₃S·3H₂O, the non-H atoms of the main molecule are approximately planar, with an r.m.s. deviation of 0.030 Å. There is a bifurcated intramolecular N—H⋯(O,S) hydrogen bond present forming S(6) and S(5) ring motifs. In the crystal, O—H⋯O and N—H⋯O hydrogen bonds link the molecules into a three-dimensional network.

Keywords: crystal structure; benzohydrazide; 1,3-thiazolidene; hydrogen bonding; biological activity.

CCDC reference: 1030606

1. Related literature

For the biological activities of thiazolidin-4-one compounds, see: Jain et al. (2012 ); Verma & Saraf (2008 ); Singh et al. (1981 ). For the synthesis, see: Brown (1961 ).

2. Experimental

2.1. Crystal data

C₁₁H₁₁N₃O₃S·3H₂O
M_r = 319.33
Triclinic, $[P \overline 1]$
a = 7.3739 (12) Å
b = 8.5110 (13) Å
c = 12.493 (2) Å
α = 103.047 (2)°
β = 101.385 (2)°
γ = 92.532 (2)°
V = 745.5 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.21 × 0.20 × 0.18 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.950, T_max = 0.957
5460 measured reflections
2731 independent reflections
2266 reflections with I > 2σ(I)
R_int = 0.020

2.3. Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.154
S = 1.10
2731 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O5ⁱ	0.84	1.83	2.655 (3)	167
N1—H1A⋯S1	0.86	2.51	2.941 (2)	112
N1—H1A⋯O1	0.86	1.92	2.609 (3)	137
N3—H3B⋯O4	0.86	1.89	2.739 (4)	170
O4—H4OA⋯O3ⁱⁱ	0.84	2.10	2.813 (4)	143
O4—H4OB⋯O6	0.81	1.81	2.587 (4)	161
O5—H5OA⋯O2ⁱⁱⁱ	0.84	2.02	2.864 (3)	178
O5—H5OB⋯O4	0.84	2.40	3.239 (6)	180
O6—H6OA⋯O2^iv	0.84	2.11	2.947 (4)	180
O6—H6OB⋯O2	0.84	2.02	2.862 (3)	180
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y+1, -z; (iv) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1030606

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814023356/lh5733sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814023356/lh5733Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814023356/lh5733Isup3.cml

checkCIF report

Comment top

4-Thiazolidinones are compounds which have a sulfur atom at position 1, a nitrogen atom at position 3 and a carbonyl group at position 4. Derivatives of 4-thiazolidinone exhibit prominent biological activites such as antibacterial, antifungal, antitubercular, anticancer, antiinflammtory, analgesic, anticonvulsant, antidepressant, antiviral/anti-HIV, antidiabetic, muscarinic receptor 1 agonist, FSH receptor agonist, trypanocidal (anti-epimastigote) and antiarrhythmic activity (Jain, et al., 2012; Verma & Saraf, 2008; Singh et al., 1981). Several hydrogen bond acceptor sites exist in these compounds, which could potentially lead to the formation of supermolecular structures. As part of our ongoing studies, the preparation and X-ray structure determination of the title compound, (I), was undertaken.

In the title molecule (Fig. 1) the bond lengths show normal ranges of values. The non-hydrogen atoms of the main molecule are approximately planar with an r.m.s. deviation of 0.030Å. There is a bifurcated intramolecular N—H···(O,S) hydrogen bond present forming S(6) and S(5) ring motifs. In the crystal, O—H···O and N—H···O hydrogen bonds form a three-dimensional network (Fig. 2).

Related literature top

For the biological activities of thiazolidin-4-one compounds, see: Jain et al. (2012); Verma & Saraf (2008); Singh et al. (1981). For the synthesis, see: Brown (1961).

Experimental top

The synthesis followed the prodecures of Brown (1961). 4-(4-Methyl salicyloyl) thiosemicarbazide (2.25 g, 0.01 mol), ethyl bromoacetate (3.34 g, 0.02 mol) and 50 ml of ethyl alcohol were added to a round-bottom flask. The mixture was stirred for 10 minutes, then slowly warmed to boiling and stirred for 8 h. After cooling to room temperature, 40 ml of water were added and the reaction mixture was left for 12 h. The resulting precipitate was filtered and recrystallized with ethyl alcohol to give 2.30 g of the title compound. Single crystals suitable for X-ray diffraction analysis were growned by slow evaporation of a solution of the title compound in methanol/water/ether (20:7:5) at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Figure 1 The molecular structure of (I), showing 30% probability displacement ellipsoids. The solvent water molecules have been omitted for clarity. Dashed lines indicate hydrogen bonds.

Figure 2 Part of the crystal structure of (I) showing hydrogen bonds as dashed lines.

(Z)-2-Hydroxy-4-methyl-N'-(4-oxo-1,3-thiazolidin-2-ylidene)benzohydrazide trihydrate top

Crystal data top

C₁₁H₁₁N₃O₃S·3H₂O	Z = 2
M_r = 319.33	F(000) = 336
Triclinic, P1	D_x = 1.423 Mg m⁻³
a = 7.3739 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5110 (13) Å	Cell parameters from 2596 reflections
c = 12.493 (2) Å	θ = 2.5–31.1°
α = 103.047 (2)°	µ = 0.25 mm⁻¹
β = 101.385 (2)°	T = 296 K
γ = 92.532 (2)°	Block, yellow
V = 745.5 (2) Å³	0.21 × 0.20 × 0.18 mm

Data collection top

Bruker APEXII CCD diffractometer	2266 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.950, T_max = 0.957	k = −10→10
5460 measured reflections	l = −14→15
2731 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.052	H-atom parameters constrained
wR(F²) = 0.154	w = 1/[σ²(F_o²) + (0.0721P)² + 0.5146P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
2731 reflections	Δρ_max = 0.53 e Å⁻³
191 parameters	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₁H₁₁N₃O₃S·3H₂O	γ = 92.532 (2)°
M_r = 319.33	V = 745.5 (2) Å³
Triclinic, P1	Z = 2
a = 7.3739 (12) Å	Mo Kα radiation
b = 8.5110 (13) Å	µ = 0.25 mm⁻¹
c = 12.493 (2) Å	T = 296 K
α = 103.047 (2)°	0.21 × 0.20 × 0.18 mm
β = 101.385 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2731 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2266 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.957	R_int = 0.020
5460 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.10	Δρ_max = 0.53 e Å⁻³
2731 reflections	Δρ_min = −0.44 e Å⁻³
191 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
S1	0.43631 (10)	−0.07307 (8)	0.18232 (6)	0.0437 (2)
O1	0.2052 (3)	−0.2057 (2)	−0.11504 (16)	0.0516 (5)
H1O	0.2170	−0.3043	−0.1393	0.077*
O2	0.1220 (3)	0.2836 (2)	−0.06337 (16)	0.0554 (6)
O3	0.6060 (3)	0.2112 (3)	0.47760 (17)	0.0650 (6)
N1	0.2365 (3)	0.0858 (3)	0.01408 (17)	0.0383 (5)
H1A	0.2525	−0.0154	0.0060	0.046*
N2	0.3037 (3)	0.1936 (2)	0.11730 (17)	0.0394 (5)
N3	0.4615 (3)	0.2237 (3)	0.30031 (18)	0.0424 (5)
H3B	0.4541	0.3266	0.3168	0.051*
C1	0.0805 (3)	0.0165 (3)	−0.1811 (2)	0.0348 (5)
C2	0.1095 (4)	−0.1485 (3)	−0.2005 (2)	0.0385 (6)
C3	0.0424 (4)	−0.2507 (3)	−0.3061 (2)	0.0459 (7)
H3A	0.0628	−0.3597	−0.3176	0.055*
C4	−0.0540 (4)	−0.1944 (3)	−0.3946 (2)	0.0444 (6)
C5	−0.0822 (4)	−0.0295 (3)	−0.3762 (2)	0.0436 (6)
H5A	−0.1456	0.0114	−0.4345	0.052*
C6	−0.0159 (4)	0.0715 (3)	−0.2714 (2)	0.0394 (6)
H6A	−0.0360	0.1806	−0.2603	0.047*
C7	−0.1260 (5)	−0.3079 (4)	−0.5088 (3)	0.0658 (9)
H7A	−0.1713	−0.4104	−0.4996	0.099*
H7B	−0.0272	−0.3230	−0.5489	0.099*
H7C	−0.2251	−0.2622	−0.5504	0.099*
C8	0.1471 (4)	0.1390 (3)	−0.0727 (2)	0.0365 (6)
C9	0.3903 (3)	0.1303 (3)	0.1930 (2)	0.0361 (6)
C10	0.5429 (4)	0.1475 (4)	0.3782 (2)	0.0450 (6)
C11	0.5482 (4)	−0.0303 (4)	0.3291 (2)	0.0484 (7)
H11A	0.4837	−0.0940	0.3678	0.058*
H11B	0.6758	−0.0574	0.3373	0.058*
O4	0.4027 (6)	0.5448 (4)	0.3300 (3)	0.1451 (18)
H4OA	0.3560	0.5885	0.3846	0.218*
H4OB	0.3221	0.5540	0.2778	0.218*
O5	0.7047 (5)	0.5074 (3)	0.1718 (3)	0.1071 (12)
H5OA	0.7543	0.5677	0.1388	0.161*
H5OB	0.6264	0.5168	0.2128	0.161*
O6	0.1984 (7)	0.5417 (4)	0.1356 (3)	0.160 (2)
H6OA	0.1074	0.5918	0.1148	0.241*
H6OB	0.1766	0.4661	0.0771	0.241*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0523 (4)	0.0375 (4)	0.0412 (4)	0.0101 (3)	0.0083 (3)	0.0095 (3)
O1	0.0767 (14)	0.0345 (10)	0.0386 (10)	0.0106 (9)	−0.0014 (9)	0.0093 (8)
O2	0.0862 (15)	0.0350 (10)	0.0397 (11)	0.0137 (10)	0.0006 (10)	0.0076 (8)
O3	0.0801 (15)	0.0747 (15)	0.0328 (11)	0.0121 (12)	−0.0027 (10)	0.0094 (10)
N1	0.0508 (13)	0.0315 (10)	0.0296 (11)	0.0045 (9)	0.0029 (9)	0.0056 (8)
N2	0.0496 (13)	0.0344 (11)	0.0309 (11)	0.0037 (9)	0.0039 (9)	0.0050 (9)
N3	0.0535 (13)	0.0363 (11)	0.0323 (11)	0.0036 (10)	0.0002 (10)	0.0058 (9)
C1	0.0363 (13)	0.0376 (13)	0.0311 (12)	0.0036 (10)	0.0081 (10)	0.0083 (10)
C2	0.0431 (14)	0.0394 (14)	0.0330 (13)	0.0032 (11)	0.0072 (11)	0.0098 (10)
C3	0.0568 (17)	0.0372 (14)	0.0395 (15)	0.0060 (12)	0.0054 (12)	0.0046 (11)
C4	0.0447 (15)	0.0492 (15)	0.0341 (14)	0.0044 (12)	0.0026 (11)	0.0044 (12)
C5	0.0424 (14)	0.0534 (16)	0.0342 (13)	0.0114 (12)	0.0046 (11)	0.0105 (12)
C6	0.0419 (14)	0.0410 (14)	0.0356 (13)	0.0098 (11)	0.0074 (11)	0.0094 (11)
C7	0.080 (2)	0.059 (2)	0.0419 (17)	0.0092 (17)	−0.0070 (15)	−0.0042 (14)
C8	0.0416 (13)	0.0350 (13)	0.0330 (13)	0.0040 (10)	0.0073 (10)	0.0089 (10)
C9	0.0383 (13)	0.0352 (13)	0.0343 (13)	0.0014 (10)	0.0081 (10)	0.0079 (10)
C10	0.0467 (15)	0.0555 (16)	0.0342 (14)	0.0067 (12)	0.0068 (12)	0.0149 (12)
C11	0.0536 (17)	0.0538 (17)	0.0426 (15)	0.0139 (13)	0.0107 (13)	0.0194 (13)
O4	0.216 (4)	0.0616 (18)	0.097 (2)	0.052 (2)	−0.072 (2)	−0.0211 (16)
O5	0.162 (3)	0.0516 (15)	0.139 (3)	0.0217 (17)	0.088 (3)	0.0362 (17)
O6	0.285 (5)	0.0653 (19)	0.073 (2)	0.074 (3)	−0.067 (3)	−0.0197 (15)

Geometric parameters (Å, º) top

S1—C9	1.759 (3)	C3—H3A	0.9300
S1—C11	1.803 (3)	C4—C5	1.401 (4)
O1—C2	1.357 (3)	C4—C7	1.511 (4)
O1—H1O	0.8400	C5—C6	1.376 (4)
O2—C8	1.236 (3)	C5—H5A	0.9300
O3—C10	1.224 (3)	C6—H6A	0.9300
N1—C8	1.334 (3)	C7—H7A	0.9600
N1—N2	1.387 (3)	C7—H7B	0.9600
N1—H1A	0.8600	C7—H7C	0.9600
N2—C9	1.271 (3)	C10—C11	1.504 (4)
N3—C10	1.349 (3)	C11—H11A	0.9700
N3—C9	1.382 (3)	C11—H11B	0.9700
N3—H3B	0.8600	O4—H4OA	0.8430
C1—C6	1.396 (4)	O4—H4OB	0.8119
C1—C2	1.404 (4)	O5—H5OA	0.8400
C1—C8	1.489 (3)	O5—H5OB	0.8399
C2—C3	1.388 (4)	O6—H6OA	0.8400
C3—C4	1.385 (4)	O6—H6OB	0.8400

C9—S1—C11	91.62 (12)	C1—C6—H6A	118.8
C2—O1—H1O	108.8	C4—C7—H7A	109.5
C8—N1—N2	120.0 (2)	C4—C7—H7B	109.5
C8—N1—H1A	120.0	H7A—C7—H7B	109.5
N2—N1—H1A	120.0	C4—C7—H7C	109.5
C9—N2—N1	114.6 (2)	H7A—C7—H7C	109.5
C10—N3—C9	117.5 (2)	H7B—C7—H7C	109.5
C10—N3—H3B	121.2	O2—C8—N1	121.3 (2)
C9—N3—H3B	121.2	O2—C8—C1	121.7 (2)
C6—C1—C2	117.5 (2)	N1—C8—C1	117.0 (2)
C6—C1—C8	117.0 (2)	N2—C9—N3	120.5 (2)
C2—C1—C8	125.5 (2)	N2—C9—S1	128.4 (2)
O1—C2—C3	120.8 (2)	N3—C9—S1	111.13 (18)
O1—C2—C1	119.0 (2)	O3—C10—N3	125.6 (3)
C3—C2—C1	120.1 (2)	O3—C10—C11	122.5 (3)
C4—C3—C2	121.7 (3)	N3—C10—C11	111.9 (2)
C4—C3—H3A	119.2	C10—C11—S1	107.76 (18)
C2—C3—H3A	119.2	C10—C11—H11A	110.2
C3—C4—C5	118.5 (2)	S1—C11—H11A	110.2
C3—C4—C7	120.8 (3)	C10—C11—H11B	110.2
C5—C4—C7	120.7 (3)	S1—C11—H11B	110.2
C6—C5—C4	119.7 (2)	H11A—C11—H11B	108.5
C6—C5—H5A	120.1	H4OA—O4—H4OB	100.2
C4—C5—H5A	120.1	H5OA—O5—H5OB	135.7
C5—C6—C1	122.5 (2)	H6OA—O6—H6OB	95.3
C5—C6—H6A	118.8

C8—N1—N2—C9	−178.4 (2)	C6—C1—C8—O2	−1.6 (4)
C6—C1—C2—O1	179.0 (2)	C2—C1—C8—O2	177.2 (3)
C8—C1—C2—O1	0.2 (4)	C6—C1—C8—N1	178.9 (2)
C6—C1—C2—C3	−0.4 (4)	C2—C1—C8—N1	−2.3 (4)
C8—C1—C2—C3	−179.2 (2)	N1—N2—C9—N3	−178.8 (2)
O1—C2—C3—C4	−179.4 (3)	N1—N2—C9—S1	0.7 (4)
C1—C2—C3—C4	0.0 (4)	C10—N3—C9—N2	176.4 (2)
C2—C3—C4—C5	0.5 (4)	C10—N3—C9—S1	−3.1 (3)
C2—C3—C4—C7	−180.0 (3)	C11—S1—C9—N2	−177.6 (3)
C3—C4—C5—C6	−0.6 (4)	C11—S1—C9—N3	1.9 (2)
C7—C4—C5—C6	179.9 (3)	C9—N3—C10—O3	−177.0 (3)
C4—C5—C6—C1	0.2 (4)	C9—N3—C10—C11	2.8 (4)
C2—C1—C6—C5	0.3 (4)	O3—C10—C11—S1	178.6 (2)
C8—C1—C6—C5	179.2 (2)	N3—C10—C11—S1	−1.2 (3)
N2—N1—C8—O2	−0.1 (4)	C9—S1—C11—C10	−0.4 (2)
N2—N1—C8—C1	179.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O5ⁱ	0.84	1.83	2.655 (3)	167
N1—H1A···S1	0.86	2.51	2.941 (2)	112
N1—H1A···O1	0.86	1.92	2.609 (3)	137
N3—H3B···O4	0.86	1.89	2.739 (4)	170
O4—H4OA···O3ⁱⁱ	0.84	2.10	2.813 (4)	143
O4—H4OB···O6	0.81	1.81	2.587 (4)	161
O5—H5OA···O2ⁱⁱⁱ	0.84	2.02	2.864 (3)	178
O5—H5OB···O4	0.84	2.40	3.239 (6)	180
O6—H6OA···O2^iv	0.84	2.11	2.947 (4)	180
O6—H6OB···O2	0.84	2.02	2.862 (3)	180

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z; (iv) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O5ⁱ	0.84	1.83	2.655 (3)	167.0
N1—H1A···S1	0.86	2.51	2.941 (2)	112.0
N1—H1A···O1	0.86	1.92	2.609 (3)	136.7
N3—H3B···O4	0.86	1.89	2.739 (4)	169.7
O4—H4OA···O3ⁱⁱ	0.84	2.10	2.813 (4)	142.7
O4—H4OB···O6	0.81	1.81	2.587 (4)	160.5
O5—H5OA···O2ⁱⁱⁱ	0.84	2.02	2.864 (3)	178.4
O5—H5OB···O4	0.84	2.40	3.239 (6)	179.8
O6—H6OA···O2^iv	0.84	2.11	2.947 (4)	179.6
O6—H6OB···O2	0.84	2.02	2.862 (3)	179.5

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z; (iv) −x, −y+1, −z.

Acknowledgements

This work was supported by the Key Project of the Natural Science Foundation of Hubei Province, China (grant No. 2008CDA067) and the Students Science and Technology Innovation Funds of the South-Central University for Nationalities.

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

Crystal structure of (Z)-2-hy­dr­oxy-4-methyl-N′-(4-oxo-1,3-thia­zolidin-2-yl­­idene)benzohydrazide trihydrate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (Z)-2-hydroxy-4-methyl-N′-(4-oxo-1,3-thiazolidin-2-ylidene)benzohydrazide trihydrate