N-[5-Methyl-2-(2-nitro­phen­yl)-4-oxo-1,3-thia­zolidin-3-yl]pyridine-3-carboxamide monohydrate

Akkurt, M.; Çelik, Í.; Demir, H.; Özkırımlı, S.; Büyükgüngör, O.

doi:10.1107/S1600536811000481

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages o293-o294

doi:10.1107/S1600536811000481

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N-[5-Methyl-2-(2-nitrophenyl)-4-oxo-1,3-thiazolidin-3-yl]pyridine-3-carboxamide monohydrate

Mehmet Akkurt,^a ^* Ísmail Çelik,^b Hale Demir,^c Sumru Özkırımlı ^c and Orhan Büyükgüngör ^d

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Physics, Faculty of Arts and Sciences, Cumhuriyet University, 58140 Sivas, Turkey, ^cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University, 34116 Beyazit, Istanbul, Turkey, and ^dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 2 December 2010; accepted 5 January 2011; online 8 January 2011)

In the title compound, C₁₆H₁₄N₄O₄S·H₂O, the benzene and pyridine rings make a dihedral angle of 85.8 (1)°. Both enantiomers of the chiral title compound are statistically disordered over the same position in the unit cell. The methyl and carbonyl group attached to the stereogenic center (C₅ of the thiazolidine ring) were therefore refined with common site-occupation factors of 0.531 (9) and 0.469 (9), respectively, for each stereoisomer. In the crystal, intermolecular N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds link the molecules, forming a three-dimensional supramolecular network. The crystal structure further shows π–π stacking interactions [centroid–centroid distance = 3.5063 (13) Å] between the pyridine rings.

Related literature

For the biological and pharmacological properties of pyridine-3-carboxamide derivatives, see: Balzarini et al. (2009 ); Baumbach et al. (1995 ); Girgis et al. (2006 ); Guzel & Salman (2009 ); Kuramochi et al. (2005 ); Moëll et al. (2009 ); Slominska et al. (2008 ); Ur et al. (2004 ); Vigorita et al. (1992 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₄N₄O₄S·H₂O
M_r = 376.40
Triclinic, $[P \overline 1]$
a = 8.1399 (4) Å
b = 8.4106 (4) Å
c = 15.0274 (7) Å
α = 92.957 (4)°
β = 104.176 (4)°
γ = 116.792 (4)°
V = 874.66 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.62 × 0.55 × 0.49 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.875, T_max = 0.899
11714 measured reflections
3963 independent reflections
3192 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.121
S = 1.04
3963 reflections
285 parameters
15 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—HN1⋯OW1ⁱ	0.86 (2)	1.96 (2)	2.804 (2)	167 (2)
OW1—HW1⋯O3Aⁱⁱ	0.81 (2)	2.02 (2)	2.806 (1)	163 (4)
OW1—HW2⋯N4ⁱⁱⁱ	0.80 (2)	2.01 (2)	2.803 (2)	173 (3)
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+2; (iii) x-2, y-1, z.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000481/im2255sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000481/im2255Isup2.hkl

checkCIF report

Comment top

Pyridine-3-carboxamide derivatives have gained attention because of their cytoprotective (Slominska et al., 2008), sodium-calcium exchanger (NCX) inhibitory (Kuramochi et al., 2005), vasodilatory (Baumbach et al., 1995), and cytotoxic (Girgis et al., 2006) properties. An inhibitory effect of pyridine-3-carboxamide on enterovirus replication and chemokine secretion has also been recently reported (Moëll et al., 2009). Here, we combine the pyridine-3-carboxamide moiety with a thiazolidinone moiety, which has shown antimycobacterial (Guzel et al., 2009), antimicrobial (Ur et al., 2004), anticancer (Vigorita et al., 1992) and antiviral (Balzarini et al., 2009) activities. Design and synthesis of bioactive molecules bearing both 4-thiazolidinone and pyridine-3-carboxamide groups take advantage of the diverse biological activities of the two scaffolds.

In the title compound (I), (Fig. 1), the bond lengths and bond angles are within normal range (Allen et al., 1987). The benzene (C1–C6) and pyridine (N4/C12–C16) rings in (I) make a dihedral angle of 85.8 (1)° with each other.

Both enantiomers of the chiral title compound are statistically disordered over the same position in the unit cell. The methyl and carbonyl group attached to the stereogenic center (C₍₅₎ of the thiazolidine ring) were therefore refined with common site occupation factors of 0.531 (9) and 0.469 (9), respectively, for each stereoisomer. Atoms C8A and C8B show strange thermal parameters due to the observed disorder.

The molecular packing (Fig. 2), is stabilized by the intermolecular N—H···O, O—H···O and O—H···N hydrogen bonds connecting the molecules to form a three-dimensional supramolecular network (Table 1). Additionally, a π-π stacking interaction in the structure was observed between the pyridine rings of the two adjacent molecules [Cg3···Cg3^iv = 3.5063 (13) Å, symmetry code (iv) 3 - x, 2 - y, 2 - z; Cg3 is a centroid of the pyridine ring (N4/C12—C16)].

Related literature top

For the biological and pharmacological properties of pyridine-3-carboxamide derivatives, see: Balzarini et al. (2009); Baumbach et al. (1995); Girgis et al. (2006); Guzel & Salman (2009); Kuramochi et al. (2005); Moëll et al. (2009); Slominska et al. (2008); Ur et al. (2004); Vigorita et al. (1992). For bond-length data, see: Allen et al. (1987).

Experimental top

0.01 mol of N'-(2-nitrobenzylidine)pyridine-3-carbohydrazide was reacted with 0.028 mol of 2-mercaptopropanoic acid in anhydrous benzene for 18 h using a Dean-Stark trap. Excess benzene was removed under reduced pressure. The residue was triturated with saturated sodium bicarbonate solution. The separated solid was filtered, washed with water and crystallized from methanol to obtain a white crystalline solid. Yield: 70.11%; m.p.: 378.2–382.1 K. UV (EtOH) λ max: 212.2, 220.0, 255.4 nm. IR (KBr) υ: 1681 (amide C=O), 1707 (thia C=O) cm^-1; ¹H-NMR (DMSO-d₆, 500 MHz): 1.48, 1.52 (3H, 2 d, J=7.3 Hz, 6.8 Hz, CH₃-thia.), 4.10 (1H, q, J= 7.0 Hz, H5-thia.), 4.21 (1H, dq, J= 6.8, 1.96 Hz, H5-thia.), 6.22 (1H, d, J=2 Hz, H2-thia), 7.51 (1H, dd, J=4.8 Hz, 4.4 Hz, H5-pyridine), 7.61–7.65 (1H, m, 2-C₆H₄—H4-thia.), 7.85–7.90 (2H, m, 2-C₆H₄-(H5,6)-thia.), 8.04–8.11 (2H, m, 2-C₆H₄—H3-thia. ve H4-pyridine), 8.73 (1H, dd, J=8.3 Hz, 2.0 Hz, H6-pyridine), 8.71, 8.79 (1H, 2 d, J=2.4 Hz, 2.4 Hz, H2-pyridine), 11.04, 11.05 (1H, 2 s, CONH) p.p.m.; ESI– (m/z, relative abundance): 358.13 ([M—H+1]^-, 17.77), 357.13 ([M—H]^-, 100). Analysis calculated for C₁₆H₁₄N₄O₄S.H₂O: C 51.06, H 4.28, N 14.89%. Found: C 51.21, H 3.73, N 14.83%.

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

	Fig. 1. View of the title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. Only the S-enantiomer is shown.
	Fig. 2. Packing diagram of (I) viewed down the a-axis and showing the hydrogen bonding pattern. All hydrogen atoms not involved in hydrogen bonding have been omitted for clarity. Only the S-enantiomers are shown.

N-[5-Methyl-2-(2-nitrophenyl)-4-oxo-1,3-thiazolidin-3-yl]pyridine-3- carboxamide monohydrate top

Crystal data top

C₁₆H₁₄N₄O₄S·H₂O	Z = 2
M_r = 376.40	F(000) = 392
Triclinic, P1	D_x = 1.429 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1399 (4) Å	Cell parameters from 15771 reflections
b = 8.4106 (4) Å	θ = 2.8–28.0°
c = 15.0274 (7) Å	µ = 0.22 mm⁻¹
α = 92.957 (4)°	T = 296 K
β = 104.176 (4)°	Block, colourless
γ = 116.792 (4)°	0.62 × 0.55 × 0.49 mm
V = 874.66 (8) Å³

Data collection top

Stoe IPDS 2 diffractometer	3963 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3192 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.038
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.5°, θ_min = 2.8°
ω scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
T_min = 0.875, T_max = 0.899	l = −19→18
11714 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.057P)² + 0.1358P] where P = (F_o² + 2F_c²)/3
3963 reflections	(Δ/σ)_max = 0.001
285 parameters	Δρ_max = 0.27 e Å⁻³
15 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₆H₁₄N₄O₄S·H₂O	γ = 116.792 (4)°
M_r = 376.40	V = 874.66 (8) Å³
Triclinic, P1	Z = 2
a = 8.1399 (4) Å	Mo Kα radiation
b = 8.4106 (4) Å	µ = 0.22 mm⁻¹
c = 15.0274 (7) Å	T = 296 K
α = 92.957 (4)°	0.62 × 0.55 × 0.49 mm
β = 104.176 (4)°

Data collection top

Stoe IPDS 2 diffractometer	3963 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	3192 reflections with I > 2σ(I)
T_min = 0.875, T_max = 0.899	R_int = 0.038
11714 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	15 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.27 e Å⁻³
3963 reflections	Δρ_min = −0.27 e Å⁻³
285 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.56133 (7)	0.45061 (8)	0.61403 (3)	0.0699 (2)
O1	0.7192 (5)	0.2528 (4)	0.38302 (13)	0.1562 (12)
O2	0.7900 (2)	0.4795 (3)	0.48092 (11)	0.0856 (6)
O3A	0.7493 (19)	0.5809 (14)	0.8800 (8)	0.091 (3)	0.531 (9)
O4	1.1251 (2)	0.84381 (17)	0.77262 (11)	0.0811 (5)
N1	0.7598 (3)	0.3251 (3)	0.46237 (12)	0.0771 (6)
N2	0.84041 (19)	0.50765 (19)	0.76035 (9)	0.0551 (4)
N3	1.0289 (2)	0.56998 (19)	0.81531 (10)	0.0563 (4)
N4	1.6987 (2)	0.9892 (2)	0.90983 (13)	0.0741 (6)
C1	0.7803 (3)	0.2246 (3)	0.53763 (13)	0.0645 (6)
C2	0.7799 (4)	0.0637 (3)	0.5129 (2)	0.0927 (9)
C3	0.7969 (4)	−0.0385 (4)	0.5785 (3)	0.1087 (13)
C4	0.8097 (4)	0.0165 (3)	0.6687 (2)	0.0947 (10)
C5	0.8058 (3)	0.1748 (3)	0.69268 (15)	0.0707 (7)
C6	0.7942 (2)	0.2861 (2)	0.62885 (12)	0.0539 (5)
C7	0.7962 (2)	0.4616 (2)	0.65973 (11)	0.0527 (5)
C8A	0.5297 (5)	0.4937 (9)	0.7236 (2)	0.0587 (13)	0.531 (9)
C9A	0.7153 (13)	0.5370 (11)	0.7958 (6)	0.0610 (19)	0.531 (9)
C10A	0.3540 (12)	0.3317 (16)	0.7341 (6)	0.126 (4)	0.531 (9)
C11	1.1625 (3)	0.7433 (2)	0.81826 (12)	0.0567 (5)
C12	1.3603 (2)	0.7956 (2)	0.87999 (12)	0.0529 (5)
C13	1.3975 (3)	0.7257 (3)	0.95825 (13)	0.0648 (6)
C14	1.5852 (3)	0.7867 (3)	1.01129 (15)	0.0738 (7)
C15	1.7293 (3)	0.9187 (3)	0.98500 (15)	0.0681 (6)
C16	1.5163 (3)	0.9272 (2)	0.85835 (14)	0.0679 (6)
C8B	0.5041 (6)	0.3820 (10)	0.7244 (3)	0.0592 (16)	0.469 (9)
C9B	0.7003 (12)	0.4774 (11)	0.7995 (6)	0.0513 (16)	0.469 (9)
C10B	0.3623 (15)	0.4314 (15)	0.7441 (7)	0.093 (3)	0.469 (9)
O3B	0.7218 (17)	0.5168 (14)	0.8810 (8)	0.076 (2)	0.469 (9)
OW1	0.0315 (2)	0.3195 (2)	0.93103 (12)	0.0931 (6)
H4	0.82100	−0.05310	0.71360	0.1130*
H7	0.89160	0.56040	0.63860	0.0630*
H8A	0.50960	0.60000	0.72670	0.0710*	0.531 (9)
H5	0.81110	0.20840	0.75370	0.0850*
H10B	0.33860	0.35480	0.79400	0.1890*	0.531 (9)
H10C	0.37100	0.22610	0.72940	0.1890*	0.531 (9)
H13	1.29640	0.63760	0.97530	0.0780*
H14	1.61340	0.73910	1.06390	0.0890*
H15	1.85600	0.96150	1.02190	0.0820*
H16	1.49240	0.97470	0.80510	0.0810*
H10A	0.24130	0.31160	0.68570	0.1890*	0.531 (9)
HN1	1.048 (3)	0.499 (2)	0.8508 (13)	0.062 (5)*
H2	0.76800	0.02530	0.45140	0.1110*
H3	0.79980	−0.14520	0.56220	0.1300*
H8B	0.45250	0.25050	0.71860	0.0710*	0.469 (9)
H10D	0.24250	0.36760	0.69470	0.1400*	0.469 (9)
H10E	0.41040	0.55960	0.74800	0.1400*	0.469 (9)
H10F	0.34190	0.39900	0.80230	0.1400*	0.469 (9)
HW1	0.078 (4)	0.355 (4)	0.9872 (13)	0.120 (11)*
HW2	−0.068 (3)	0.230 (3)	0.924 (2)	0.126 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0665 (3)	0.1068 (4)	0.0450 (2)	0.0532 (3)	0.0084 (2)	0.0109 (2)
O1	0.245 (3)	0.159 (2)	0.0532 (10)	0.088 (2)	0.0453 (15)	0.0094 (12)
O2	0.0975 (11)	0.1172 (13)	0.0581 (8)	0.0619 (10)	0.0255 (8)	0.0329 (9)
O3A	0.103 (6)	0.130 (7)	0.046 (3)	0.069 (5)	0.009 (3)	−0.007 (4)
O4	0.0813 (9)	0.0583 (7)	0.0893 (10)	0.0317 (7)	0.0032 (8)	0.0239 (7)
N1	0.0713 (10)	0.1071 (14)	0.0478 (9)	0.0377 (10)	0.0208 (8)	0.0090 (9)
N2	0.0463 (7)	0.0679 (8)	0.0414 (7)	0.0231 (6)	0.0062 (5)	0.0082 (6)
N3	0.0466 (7)	0.0540 (7)	0.0549 (8)	0.0182 (6)	0.0038 (6)	0.0145 (6)
N4	0.0560 (9)	0.0652 (9)	0.0838 (12)	0.0139 (7)	0.0225 (8)	0.0155 (8)
C1	0.0540 (9)	0.0745 (11)	0.0580 (10)	0.0266 (8)	0.0150 (8)	0.0051 (8)
C2	0.0887 (16)	0.0873 (15)	0.0903 (17)	0.0380 (13)	0.0218 (13)	−0.0130 (13)
C3	0.114 (2)	0.0742 (15)	0.131 (3)	0.0498 (15)	0.0206 (19)	−0.0047 (16)
C4	0.0990 (18)	0.0634 (12)	0.107 (2)	0.0358 (12)	0.0121 (15)	0.0204 (12)
C5	0.0716 (12)	0.0611 (10)	0.0665 (12)	0.0247 (9)	0.0125 (9)	0.0166 (9)
C6	0.0446 (8)	0.0596 (9)	0.0512 (9)	0.0209 (7)	0.0117 (7)	0.0111 (7)
C7	0.0508 (8)	0.0626 (9)	0.0425 (8)	0.0253 (7)	0.0131 (6)	0.0155 (7)
C8A	0.061 (2)	0.071 (3)	0.0513 (18)	0.038 (2)	0.0153 (15)	0.0157 (17)
C9A	0.070 (3)	0.069 (4)	0.051 (3)	0.041 (3)	0.014 (2)	0.012 (3)
C10A	0.066 (4)	0.190 (9)	0.077 (5)	0.021 (5)	0.019 (3)	0.056 (6)
C11	0.0582 (9)	0.0502 (8)	0.0557 (9)	0.0233 (7)	0.0124 (8)	0.0097 (7)
C12	0.0519 (8)	0.0440 (7)	0.0542 (9)	0.0174 (6)	0.0135 (7)	0.0069 (6)
C13	0.0504 (9)	0.0669 (10)	0.0607 (10)	0.0152 (8)	0.0138 (8)	0.0192 (8)
C14	0.0571 (10)	0.0843 (13)	0.0658 (11)	0.0242 (9)	0.0118 (9)	0.0250 (10)
C15	0.0485 (9)	0.0713 (11)	0.0739 (12)	0.0220 (8)	0.0151 (9)	0.0082 (9)
C16	0.0628 (11)	0.0543 (9)	0.0709 (12)	0.0160 (8)	0.0168 (9)	0.0182 (8)
C8B	0.051 (2)	0.071 (4)	0.053 (2)	0.027 (2)	0.0144 (16)	0.017 (2)
C9B	0.050 (2)	0.065 (4)	0.039 (2)	0.027 (3)	0.0129 (16)	0.018 (3)
C10B	0.080 (5)	0.150 (8)	0.073 (3)	0.071 (6)	0.031 (3)	0.021 (5)
O3B	0.060 (2)	0.113 (6)	0.043 (3)	0.031 (4)	0.0160 (18)	0.015 (4)
OW1	0.0800 (10)	0.0681 (9)	0.0728 (10)	0.0017 (8)	−0.0099 (8)	0.0323 (8)

Geometric parameters (Å, º) top

S1—C7	1.8238 (19)	C8A—C9A	1.501 (11)
S1—C8A	1.772 (4)	C8A—C10A	1.518 (14)
S1—C8B	1.880 (5)	C8B—C10B	1.476 (15)
O1—N1	1.205 (3)	C8B—C9B	1.529 (11)
O2—N1	1.211 (3)	C11—C12	1.495 (3)
O3A—C9A	1.226 (14)	C12—C16	1.384 (3)
O3B—C9B	1.201 (15)	C12—C13	1.370 (3)
O4—C11	1.211 (2)	C13—C14	1.374 (4)
OW1—HW1	0.813 (19)	C14—C15	1.365 (3)
OW1—HW2	0.80 (2)	C2—H2	0.9300
N1—C1	1.468 (3)	C3—H3	0.9300
N2—N3	1.386 (2)	C4—H4	0.9300
N2—C7	1.454 (2)	C5—H5	0.9300
N2—C9A	1.364 (11)	C7—H7	0.9800
N2—C9B	1.339 (10)	C8A—H8A	0.9800
N3—C11	1.360 (2)	C8B—H8B	0.9800
N4—C16	1.331 (3)	C10A—H10B	0.9600
N4—C15	1.324 (3)	C10A—H10C	0.9600
N3—HN1	0.861 (18)	C10A—H10A	0.9600
C1—C6	1.399 (3)	C10B—H10F	0.9600
C1—C2	1.383 (4)	C10B—H10E	0.9600
C2—C3	1.363 (5)	C10B—H10D	0.9600
C3—C4	1.373 (5)	C13—H13	0.9300
C4—C5	1.378 (4)	C14—H14	0.9300
C5—C6	1.390 (3)	C15—H15	0.9300
C6—C7	1.516 (2)	C16—H16	0.9300

S1···O2	2.999 (2)	C12···C15^ix	3.496 (3)
S1···N1	3.466 (2)	C13···O3B^vi	3.288 (11)
S1···S1ⁱ	3.5774 (7)	C13···OW1^vii	3.286 (3)
S1···O2ⁱ	3.188 (2)	C14···C12^ix	3.586 (3)
O1···O4ⁱⁱ	3.150 (4)	C14···C16^ix	3.523 (3)
O1···C11ⁱⁱ	3.389 (3)	C14···O3A^vii	3.420 (15)
OW1···C13ⁱⁱⁱ	3.286 (3)	C15···C12^ix	3.496 (3)
OW1···N4^iv	2.803 (2)	C15···O3A^vii	3.266 (13)
OW1···O3A^v	2.806 (12)	C16···C14^ix	3.523 (3)
OW1···N3ⁱⁱⁱ	2.804 (2)	C5···HN1	3.026 (17)
OW1···O3B^v	2.870 (12)	C9B···H5	2.9000
O2···C7	2.688 (2)	C10A···H14^vi	3.0900
O2···S1ⁱ	3.188 (2)	C11···H7	2.8500
O2···N1ⁱⁱ	3.123 (3)	C12···H10E^vii	2.9600
O2···S1	2.999 (2)	C13···HN1	2.62 (2)
O2···O2ⁱⁱ	3.177 (3)	C15···H15^x	3.0900
O2···C1ⁱⁱ	3.348 (3)	C15···HW2^viii	2.74 (2)
O3A···C15ⁱⁱⁱ	3.266 (13)	C16···H10E^vii	3.0700
O3A···C11	3.400 (16)	C16···HW2^viii	3.04 (3)
O3A···C14ⁱⁱⁱ	3.420 (15)	HN1···OW1^vii	1.958 (17)
O3A···OW1^v	2.806 (12)	HN1···C5	3.026 (17)
O3A···N3	2.720 (16)	HN1···H5	2.4100
O3B···OW1^v	2.870 (12)	HN1···HW1^vii	2.45 (3)
O3B···C13^vi	3.288 (11)	HN1···HW2^vii	2.46 (3)
O3B···N3	2.769 (15)	HN1···O3B	2.87 (3)
O4···C7	3.136 (2)	HN1···H13	2.1800
O4···C9A	3.288 (10)	HN1···C13	2.62 (2)
O4···O1ⁱⁱ	3.150 (4)	H2···O1	2.3600
O4···N2	2.689 (2)	HW1···H13ⁱⁱⁱ	2.2900
O1···H10Eⁱ	2.8800	HW1···O3B^v	2.09 (2)
O1···H8Aⁱ	2.9200	HW1···O3A^v	2.02 (2)
O1···H2	2.3600	HW1···HN1ⁱⁱⁱ	2.45 (3)
OW1···H5ⁱⁱⁱ	2.6600	HW2···C16^iv	3.04 (3)
OW1···H13ⁱⁱⁱ	2.4800	HW2···N4^iv	2.01 (2)
OW1···HN1ⁱⁱⁱ	1.958 (17)	HW2···C15^iv	2.74 (2)
O2···H7	2.2600	HW2···H5ⁱⁱⁱ	2.4700
O3A···H10B	2.8900	HW2···HN1ⁱⁱⁱ	2.46 (3)
O3A···H13^vi	2.9000	H5···HN1	2.4100
O3A···HW1^v	2.02 (2)	H5···HW2^vii	2.4700
O3B···H10F	2.7000	H5···OW1^vii	2.6600
O3B···HN1	2.87 (3)	H5···N2	2.4100
O3B···H13^vi	2.5800	H5···C9B	2.9000
O3B···HW1^v	2.09 (3)	H5···N3	2.7000
O4···H7	2.6300	H7···O2	2.2600
O4···H16	2.5800	H7···O4	2.6300
N1···S1	3.466 (2)	H7···C11	2.8500
N1···O2ⁱⁱ	3.123 (3)	H7···N1	2.8700
N2···O4	2.689 (2)	H8A···O1ⁱ	2.9200
N3···O3B	2.769 (15)	H10B···O3A	2.8900
N3···OW1^vii	2.804 (2)	H10B···H14^vi	2.3200
N3···O3A	2.720 (16)	H10E···C12ⁱⁱⁱ	2.9600
N3···C5	3.167 (3)	H10E···O1ⁱ	2.8800
N4···OW1^viii	2.803 (2)	H10E···C16ⁱⁱⁱ	3.0700
N1···H7	2.8700	H10F···H14^vi	2.4100
N2···H5	2.4100	H10F···O3B	2.7000
N3···H13	2.6500	H13···OW1^vii	2.4800
N3···H5	2.7000	H13···N3	2.6500
N4···HW2^viii	2.01 (2)	H13···HN1	2.1800
C1···O2ⁱⁱ	3.348 (3)	H13···HW1^vii	2.2900
C5···C9B	3.466 (10)	H13···O3A^vi	2.9000
C5···N3	3.167 (3)	H13···O3B^vi	2.5800
C7···O2	2.688 (2)	H14···C10A^vi	3.0900
C7···O4	3.136 (2)	H14···H10B^vi	2.3200
C9A···O4	3.288 (10)	H14···H10F^vi	2.4100
C9B···C5	3.466 (10)	H15···C15^x	3.0900
C11···O3A	3.400 (16)	H15···H15^x	2.4000
C11···O1ⁱⁱ	3.389 (3)	H16···O4	2.5800
C12···C14^ix	3.586 (3)

C7—S1—C8A	96.72 (17)	C13—C12—C16	117.71 (19)
C7—S1—C8B	89.56 (19)	C11—C12—C13	124.34 (17)
HW1—OW1—HW2	105 (3)	C12—C13—C14	119.5 (2)
O1—N1—C1	118.6 (2)	C13—C14—C15	118.5 (2)
O2—N1—C1	120.00 (17)	N4—C15—C14	123.6 (2)
O1—N1—O2	121.4 (2)	N4—C16—C12	123.38 (17)
N3—N2—C9A	119.9 (4)	C3—C2—H2	120.00
N3—N2—C9B	120.7 (4)	C1—C2—H2	120.00
N3—N2—C7	118.23 (15)	C2—C3—H3	120.00
C7—N2—C9B	120.9 (4)	C4—C3—H3	120.00
C7—N2—C9A	119.4 (4)	C3—C4—H4	120.00
N2—N3—C11	118.67 (16)	C5—C4—H4	120.00
C15—N4—C16	117.28 (18)	C6—C5—H5	119.00
C11—N3—HN1	124.9 (14)	C4—C5—H5	119.00
N2—N3—HN1	115.9 (14)	N2—C7—H7	109.00
N1—C1—C2	116.4 (2)	C6—C7—H7	109.00
N1—C1—C6	121.7 (2)	S1—C7—H7	109.00
C2—C1—C6	121.9 (2)	S1—C8A—H8A	109.00
C1—C2—C3	120.1 (3)	C10A—C8A—H8A	109.00
C2—C3—C4	119.8 (3)	C9A—C8A—H8A	109.00
C3—C4—C5	120.0 (3)	C9B—C8B—H8B	109.00
C4—C5—C6	122.3 (2)	C10B—C8B—H8B	109.00
C5—C6—C7	120.07 (16)	S1—C8B—H8B	109.00
C1—C6—C7	124.04 (16)	H10A—C10A—H10B	109.00
C1—C6—C5	115.89 (18)	C8A—C10A—H10C	109.00
N2—C7—C6	113.13 (13)	C8A—C10A—H10B	110.00
S1—C7—N2	103.61 (12)	H10A—C10A—H10C	109.00
S1—C7—C6	112.56 (12)	H10B—C10A—H10C	109.00
C9A—C8A—C10A	114.1 (6)	C8A—C10A—H10A	110.00
S1—C8A—C9A	106.0 (5)	C8B—C10B—H10D	109.00
S1—C8A—C10A	109.8 (5)	C8B—C10B—H10E	109.00
C9B—C8B—C10B	113.3 (7)	H10D—C10B—H10F	110.00
S1—C8B—C10B	112.3 (5)	H10D—C10B—H10E	109.00
S1—C8B—C9B	104.0 (5)	H10E—C10B—H10F	110.00
N2—C9A—C8A	113.7 (6)	C8B—C10B—H10F	109.00
O3A—C9A—C8A	124.5 (12)	C14—C13—H13	120.00
O3A—C9A—N2	121.6 (11)	C12—C13—H13	120.00
O3B—C9B—C8B	124.1 (11)	C13—C14—H14	121.00
N2—C9B—C8B	109.7 (6)	C15—C14—H14	121.00
O3B—C9B—N2	126.2 (11)	N4—C15—H15	118.00
O4—C11—N3	122.8 (2)	C14—C15—H15	118.00
N3—C11—C12	113.92 (16)	N4—C16—H16	118.00
O4—C11—C12	123.26 (16)	C12—C16—H16	118.00
C11—C12—C16	117.92 (16)

C8A—S1—C7—C6	120.0 (2)	N1—C1—C2—C3	−179.5 (3)
C7—S1—C8A—C10A	−117.5 (5)	C2—C1—C6—C7	179.7 (2)
C7—S1—C8A—C9A	6.1 (5)	C1—C2—C3—C4	1.6 (5)
C8A—S1—C7—N2	−2.6 (2)	C2—C3—C4—C5	−0.2 (5)
O1—N1—C1—C6	−168.9 (3)	C3—C4—C5—C6	−1.7 (5)
O1—N1—C1—C2	9.5 (4)	C4—C5—C6—C1	2.0 (4)
O2—N1—C1—C2	−168.0 (3)	C4—C5—C6—C7	−178.2 (2)
O2—N1—C1—C6	13.7 (4)	C5—C6—C7—N2	8.9 (3)
C9A—N2—N3—C11	−86.1 (5)	C1—C6—C7—S1	71.6 (2)
N3—N2—C7—S1	−164.40 (12)	C5—C6—C7—S1	−108.16 (19)
C7—N2—N3—C11	75.9 (2)	C1—C6—C7—N2	−171.39 (19)
C9A—N2—C7—C6	−124.5 (4)	C10A—C8A—C9A—N2	112.4 (7)
C9A—N2—C7—S1	−2.3 (4)	S1—C8A—C9A—N2	−8.5 (7)
N3—N2—C7—C6	73.41 (19)	C10A—C8A—C9A—O3A	−62.0 (12)
C7—N2—C9A—C8A	7.4 (8)	S1—C8A—C9A—O3A	177.1 (9)
N3—N2—C9A—O3A	−16.3 (11)	N3—C11—C12—C13	−30.2 (3)
C7—N2—C9A—O3A	−178.0 (8)	O4—C11—C12—C13	152.0 (2)
N3—N2—C9A—C8A	169.1 (4)	O4—C11—C12—C16	−26.0 (3)
N2—N3—C11—C12	179.78 (15)	N3—C11—C12—C16	151.82 (18)
N2—N3—C11—O4	−2.4 (3)	C16—C12—C13—C14	−0.4 (3)
C16—N4—C15—C14	0.6 (3)	C11—C12—C16—N4	177.67 (18)
C15—N4—C16—C12	0.4 (3)	C11—C12—C13—C14	−178.5 (2)
N1—C1—C6—C5	177.7 (2)	C13—C12—C16—N4	−0.5 (3)
N1—C1—C6—C7	−2.1 (3)	C12—C13—C14—C15	1.3 (3)
C6—C1—C2—C3	−1.2 (5)	C13—C14—C15—N4	−1.4 (4)
C2—C1—C6—C5	−0.6 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x−1, y, z; (iv) x−2, y−1, z; (v) −x+1, −y+1, −z+2; (vi) −x+2, −y+1, −z+2; (vii) x+1, y, z; (viii) x+2, y+1, z; (ix) −x+3, −y+2, −z+2; (x) −x+4, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—HN1···OW1^vii	0.86 (2)	1.96 (2)	2.804 (2)	167 (2)
OW1—HW1···O3A^v	0.81 (2)	2.02 (2)	2.806 (1)	163 (4)
OW1—HW2···N4^iv	0.80 (2)	2.01 (2)	2.803 (2)	173 (3)
C5—H5···N2	0.93	2.41	2.794 (3)	104
C7—H7···O2	0.98	2.26	2.688 (2)	105
C13—H13···OW1^vii	0.93	2.48	3.286 (3)	145

Symmetry codes: (iv) x−2, y−1, z; (v) −x+1, −y+1, −z+2; (vii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₄O₄S·H₂O
M_r	376.40
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.1399 (4), 8.4106 (4), 15.0274 (7)
α, β, γ (°)	92.957 (4), 104.176 (4), 116.792 (4)
V (Å³)	874.66 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.62 × 0.55 × 0.49

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.875, 0.899
No. of measured, independent and observed [I > 2σ(I)] reflections	11714, 3963, 3192
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.121, 1.04
No. of reflections	3963
No. of parameters	285
No. of restraints	15
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.27

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···A	D—H	H···A	D···A	D—H···A
N3—HN1···OW1ⁱ	0.86 (2)	1.96 (2)	2.804 (2)	167 (2)
OW1—HW1···O3Aⁱⁱ	0.81 (2)	2.02 (2)	2.806 (1)	163 (4)
OW1—HW2···N4ⁱⁱⁱ	0.80 (2)	2.01 (2)	2.803 (2)	173 (3)

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+2; (iii) x−2, y−1, z.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). HD and SO acknowledge the Scientific Research Projects Coordination Unit of Istanbul University (Project number T-3691).

References

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Volume 67| Part 2| February 2011| Pages o293-o294

doi:10.1107/S1600536811000481

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

N-[5-Methyl-2-(2-nitro­phen­yl)-4-oxo-1,3-thia­zolidin-3-yl]pyridine-3-carboxamide monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-[5-Methyl-2-(2-nitrophenyl)-4-oxo-1,3-thiazolidin-3-yl]pyridine-3-carboxamide monohydrate