N-[4-Acetyl-5-(4-fluoro­phen­yl)-4,5-di­hydro-1,3,4-thia­diazol-2-yl]acetamide

Kavitha, H.D.; Marganakop, S.B.; Kamble, R.R.; Roopashree, K.R.; Devarajegowda, H.C.

doi:10.1107/S1600536813009367

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Pages o701-o702

https://doi.org/10.1107/S1600536813009367

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N-[4-Acetyl-5-(4-fluorophenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide

H. D. Kavitha,^a Sheetal B. Marganakop,^b Ravindra R. Kamble,^b K. R. Roopashree ^c and H. C. Devarajegowda ^c ^*

^aDepartment of Physics, Government Science College, Hassan 573 201, Karnataka, India, ^bDepartment of Studies in Chemistry, Karnataka University, Dharwad 580 003, Karnataka , India, and ^cDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com, kamchem9@gmail.com

(Received 31 March 2013; accepted 7 April 2013; online 13 April 2013)

The title molecule, C₁₂H₁₂FN₃O₂S, shows a short intramolecular S⋯O contact of 2.682 (18) Å. The dihedral angle between the thiadiazole ring and the benzene ring is 86.82 (11)°. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds generate an R₂¹(6) graph-set motif between adjacent molecules. Pairs of futher C—H⋯O hydrogen bonds form inversion dimers with R₂²(8) ring motifs. These combine to generate a three-dimensional network and stack the molecules along the b axis.

Related literature

For biological applications of 1,3,4-thiadiazole derivatives, see: Matysiak & Opolski (2006 ); Kumar et al. (2012 ); Oruç et al. (2004 ); Kadi et al. (2007 ); Noolvi et al. (2011 ); Matysiak et al. (2006 ); Marganakop et al. (2012 ). For a related structure, see: Zhang (2009 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₂H₁₂FN₃O₂S
M_r = 281.31
Monoclinic, P 2₁ /c
a = 9.5061 (6) Å
b = 11.2152 (7) Å
c = 12.7752 (7) Å
β = 101.823 (4)°
V = 1333.11 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.770, T_max = 1.000
11372 measured reflections
2352 independent reflections
2035 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.121
S = 1.07
2352 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯O4ⁱ	0.86	1.96	2.815 (2)	171
C10—H10⋯O3ⁱⁱ	0.93	2.58	3.267 (3)	131
C17—H17A⋯O4ⁱ	0.96	2.46	3.316 (3)	148
C19—H19B⋯O4ⁱⁱⁱ	0.96	2.55	3.335 (3)	139
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z+1.

Data collection: SMART (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: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813009367/sj5314sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813009367/sj5314Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813009367/sj5314Isup3.cml

checkCIF report

Comment top

1,3,4-Thiadiazole derivatives are of great importance to chemists as well as biologists as they are found in a large variety of naturally occurring compounds and also pharmacologically potent molecules. These derivatives are known to exhibit a broad spectrum of activities including antiproliferative, antituberculosis, anti-inflammatory, anticancer and antimicrobial activities (Matysiak et al., 2006; Kumar et al., 2012; Oruç et al., 2004; Kadi et al., 2007; Noolvi et al., 2011; Matysiak & Opolski, 2006; Marganakop et al., 2012).

The asymmetric unit of the structure of N-[4-Acetyl-5-(4-fluorophenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl] -acetamide is shown in Fig. 1 and exhibits a short intramolecular S2···O3 contact of 2.682 (18) Å. The dihedral angle between the thiadiazole ring (S2/N6/N7/C14/C15) and the benzene ring (C8–C13) is 86.82 (11)°. In the structure, all bond lengths and angles are within normal ranges (Zhang, 2009).

In the crystal, the N5—H5···O4 and C17—H17A···O4 hydrogen bonds (Table 1) link adjacent molecules forming rings with an R¹₂(6) graph-set motif (Bernstein et al., 1995). The crystal structure is further stabilized by other intermolecular C—H···O hydrogen bonds, (Table 1), that generate inversion dimers with R²₂(8) ring motifs. The overall crystal packing components generate a three-dimensional network, stacking molecules along the b axis, (Fig. 2).

Related literature top

For biological applications of 1,3,4-thiadiazole derivatives, see: Matysiak & Opolski (2006); Kumar et al. (2012); Oruç et al. (2004); Kadi et al. (2007); Noolvi et al. (2011); Matysiak et al. (2006); Marganakop et al. (2012). For a related structure, see: Zhang (2009). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

A mixture of p-fluorobenzaldehyde (0.005 mole), and thiosemicarbazide (0.005 mole) was refluxed in ethanol (10 ml) and acetic acid (2 drops), after completion of the reaction the resulting pale yellow powder was filtered, dried and crystallized in ethanol to obtain (E)-1-(4-fluoro benzylidene)thiosemicarbazide, which was further heated at 80–90°C for about 4 hrs and the reaction mixture was cooled to room temperature and poured into ice cold water. The precipitate obtained was filtered off, washed with water, dried and purified by crystallization in aqueous alcohol (80%, v/v) to yield pale yellow crystals of N– [4-acetyl-5-(4-fluorophenyl)-4,5-dihydro-[1,3,4]thiadiazol-2-yl]- acetamide. Yield: (70%), m. p: 490 K.

Structure description top

For biological applications of 1,3,4-thiadiazole derivatives, see: Matysiak & Opolski (2006); Kumar et al. (2012); Oruç et al. (2004); Kadi et al. (2007); Noolvi et al. (2011); Matysiak et al. (2006); Marganakop et al. (2012). For a related structure, see: Zhang (2009). For graph-set notation, see: Bernstein et al. (1995).

Computing details top

Data collection: SMART (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: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. Packing of the molecule in the unit cell.

N-[4-Acetyl-5-(4-fluorophenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide top

Crystal data top

C₁₂H₁₂FN₃O₂S	F(000) = 584
M_r = 281.31	D_x = 1.402 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 490 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.5061 (6) Å	Cell parameters from 2352 reflections
b = 11.2152 (7) Å	θ = 2.2–25.0°
c = 12.7752 (7) Å	µ = 0.26 mm⁻¹
β = 101.823 (4)°	T = 296 K
V = 1333.11 (14) Å³	Plate, colourless
Z = 4	0.24 × 0.20 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2352 independent reflections
Radiation source: fine-focus sealed tube	2035 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω and φ scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −11→11
T_min = 0.770, T_max = 1.000	k = −13→12
11372 measured reflections	l = −15→15

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0619P)² + 0.7142P] where P = (F_o² + 2F_c²)/3
2352 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₂H₁₂FN₃O₂S	V = 1333.11 (14) Å³
M_r = 281.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5061 (6) Å	µ = 0.26 mm⁻¹
b = 11.2152 (7) Å	T = 296 K
c = 12.7752 (7) Å	0.24 × 0.20 × 0.12 mm
β = 101.823 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2352 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2035 reflections with I > 2σ(I)
T_min = 0.770, T_max = 1.000	R_int = 0.024
11372 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.07	Δρ_max = 0.42 e Å⁻³
2352 reflections	Δρ_min = −0.34 e Å⁻³
172 parameters

Special details top

Experimental. Spectroscopic data IR (KBr); 3233, 2799, 1646, 1626, 1H NMR (300 MHz, CDCl3, δ p.p.m.): 2.11 (s, 3H, CH3 of NHCOCH3), 2.24 (s, 3H, CH3 of –NCOCH3), 4.70 (s, 1H, C—H of C5—H), 6.85–7.10 (m, 4H, Ar—H), 11.77 (s, 1H, NHCO), MS (m/z, 70 eV); 282 (M⁺¹, 20), 239 (26), 204 (100).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
F1	−0.11204 (19)	0.1673 (2)	0.41894 (18)	0.1026 (7)
S2	0.32591 (7)	0.09255 (5)	0.09191 (4)	0.0449 (2)
O3	0.2686 (2)	−0.01822 (15)	−0.09810 (14)	0.0665 (5)
O4	0.56411 (17)	0.11842 (14)	0.42490 (13)	0.0472 (4)
N5	0.3591 (2)	−0.14036 (15)	0.03899 (13)	0.0407 (4)
H5	0.3826	−0.2127	0.0571	0.049*
N6	0.45429 (18)	−0.08120 (15)	0.21164 (13)	0.0367 (4)
N7	0.46451 (18)	0.01994 (15)	0.27693 (14)	0.0374 (4)
C8	0.0057 (3)	0.1564 (3)	0.3747 (2)	0.0626 (7)
C9	0.0942 (3)	0.2522 (2)	0.3768 (2)	0.0558 (6)
H9	0.0750	0.3239	0.4076	0.067*
C10	0.2141 (2)	0.2394 (2)	0.33124 (17)	0.0441 (5)
H10	0.2768	0.3032	0.3321	0.053*
C11	0.2413 (2)	0.13353 (19)	0.28503 (16)	0.0372 (5)
C12	0.1473 (3)	0.0389 (2)	0.2839 (2)	0.0551 (6)
H12	0.1645	−0.0327	0.2520	0.066*
C13	0.0287 (3)	0.0497 (3)	0.3296 (3)	0.0677 (8)
H13	−0.0340	−0.0140	0.3297	0.081*
C14	0.3719 (2)	0.12171 (18)	0.23621 (16)	0.0375 (5)
H14	0.4283	0.1953	0.2490	0.045*
C15	0.3864 (2)	−0.05435 (18)	0.11717 (16)	0.0358 (5)
C16	0.2973 (3)	−0.1186 (2)	−0.06565 (17)	0.0453 (5)
C17	0.2681 (3)	−0.2264 (2)	−0.1344 (2)	0.0604 (7)
H17A	0.2994	−0.2961	−0.0925	0.091*
H17B	0.3192	−0.2206	−0.1917	0.091*
H17C	0.1669	−0.2321	−0.1635	0.091*
C18	0.5596 (2)	0.02706 (18)	0.37069 (16)	0.0363 (5)
C19	0.6546 (3)	−0.0775 (2)	0.40480 (18)	0.0478 (6)
H19A	0.6340	−0.1389	0.3515	0.072*
H19B	0.6377	−0.1074	0.4716	0.072*
H19C	0.7533	−0.0536	0.4134	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0620 (10)	0.1312 (19)	0.1269 (17)	0.0023 (11)	0.0478 (11)	−0.0189 (15)
S2	0.0679 (4)	0.0285 (3)	0.0365 (3)	0.0074 (2)	0.0066 (3)	0.0035 (2)
O3	0.1095 (15)	0.0395 (10)	0.0444 (9)	0.0104 (10)	0.0014 (9)	0.0058 (8)
O4	0.0573 (9)	0.0333 (8)	0.0485 (9)	−0.0053 (7)	0.0049 (7)	−0.0088 (7)
N5	0.0608 (11)	0.0261 (9)	0.0339 (9)	0.0035 (8)	0.0064 (8)	0.0009 (7)
N6	0.0464 (10)	0.0272 (9)	0.0352 (9)	0.0023 (7)	0.0055 (7)	−0.0024 (7)
N7	0.0465 (10)	0.0263 (9)	0.0373 (9)	0.0032 (7)	0.0038 (7)	−0.0032 (7)
C8	0.0439 (13)	0.082 (2)	0.0635 (16)	0.0081 (13)	0.0142 (12)	−0.0031 (15)
C9	0.0545 (14)	0.0586 (16)	0.0519 (14)	0.0122 (12)	0.0057 (11)	−0.0124 (12)
C10	0.0479 (12)	0.0374 (12)	0.0440 (12)	0.0021 (9)	0.0022 (9)	−0.0049 (10)
C11	0.0425 (11)	0.0306 (11)	0.0355 (10)	0.0022 (9)	0.0007 (8)	0.0009 (8)
C12	0.0569 (14)	0.0389 (13)	0.0706 (17)	−0.0043 (11)	0.0157 (12)	−0.0055 (12)
C13	0.0537 (15)	0.0634 (18)	0.089 (2)	−0.0146 (13)	0.0225 (14)	−0.0058 (16)
C14	0.0481 (11)	0.0247 (10)	0.0381 (11)	0.0007 (9)	0.0051 (9)	0.0005 (8)
C15	0.0451 (11)	0.0272 (10)	0.0352 (11)	0.0004 (9)	0.0083 (9)	0.0008 (8)
C16	0.0603 (14)	0.0361 (12)	0.0377 (11)	0.0047 (10)	0.0060 (10)	0.0030 (10)
C17	0.0867 (18)	0.0469 (15)	0.0405 (13)	0.0070 (13)	−0.0036 (12)	−0.0061 (11)
C18	0.0389 (10)	0.0315 (11)	0.0387 (11)	−0.0051 (8)	0.0082 (8)	−0.0007 (9)
C19	0.0494 (13)	0.0440 (14)	0.0452 (13)	0.0053 (10)	−0.0014 (10)	−0.0028 (10)

Geometric parameters (Å, º) top

F1—C8	1.359 (3)	C10—C11	1.374 (3)
S2—C15	1.753 (2)	C10—H10	0.9300
S2—C14	1.835 (2)	C11—C12	1.386 (3)
O3—C16	1.211 (3)	C11—C14	1.505 (3)
O4—C18	1.233 (3)	C12—C13	1.376 (4)
N5—C16	1.368 (3)	C12—H12	0.9300
N5—C15	1.374 (3)	C13—H13	0.9300
N5—H5	0.8600	C14—H14	0.9800
N6—C15	1.283 (3)	C16—C17	1.487 (3)
N6—N7	1.399 (2)	C17—H17A	0.9600
N7—C18	1.347 (3)	C17—H17B	0.9600
N7—C14	1.470 (3)	C17—H17C	0.9600
C8—C9	1.361 (4)	C18—C19	1.490 (3)
C8—C13	1.365 (4)	C19—H19A	0.9600
C9—C10	1.389 (3)	C19—H19B	0.9600
C9—H9	0.9300	C19—H19C	0.9600

C15—S2—C14	88.91 (9)	N7—C14—S2	102.66 (13)
C16—N5—C15	124.35 (18)	C11—C14—S2	112.67 (14)
C16—N5—H5	117.8	N7—C14—H14	109.1
C15—N5—H5	117.8	C11—C14—H14	109.1
C15—N6—N7	109.31 (17)	S2—C14—H14	109.1
C18—N7—N6	122.01 (17)	N6—C15—N5	120.17 (19)
C18—N7—C14	120.85 (17)	N6—C15—S2	118.48 (16)
N6—N7—C14	117.06 (16)	N5—C15—S2	121.34 (15)
F1—C8—C9	118.6 (3)	O3—C16—N5	121.5 (2)
F1—C8—C13	118.1 (3)	O3—C16—C17	123.5 (2)
C9—C8—C13	123.3 (2)	N5—C16—C17	115.0 (2)
C8—C9—C10	117.8 (2)	C16—C17—H17A	109.5
C8—C9—H9	121.1	C16—C17—H17B	109.5
C10—C9—H9	121.1	H17A—C17—H17B	109.5
C11—C10—C9	120.8 (2)	C16—C17—H17C	109.5
C11—C10—H10	119.6	H17A—C17—H17C	109.5
C9—C10—H10	119.6	H17B—C17—H17C	109.5
C10—C11—C12	119.2 (2)	O4—C18—N7	119.26 (19)
C10—C11—C14	119.87 (19)	O4—C18—C19	122.74 (19)
C12—C11—C14	120.9 (2)	N7—C18—C19	118.00 (18)
C13—C12—C11	120.7 (2)	C18—C19—H19A	109.5
C13—C12—H12	119.6	C18—C19—H19B	109.5
C11—C12—H12	119.6	H19A—C19—H19B	109.5
C8—C13—C12	118.1 (3)	C18—C19—H19C	109.5
C8—C13—H13	120.9	H19A—C19—H19C	109.5
C12—C13—H13	120.9	H19B—C19—H19C	109.5
N7—C14—C11	114.02 (17)

C15—N6—N7—C18	−162.76 (18)	C12—C11—C14—N7	−53.9 (3)
C15—N6—N7—C14	14.0 (2)	C10—C11—C14—S2	−117.30 (19)
F1—C8—C9—C10	179.9 (2)	C12—C11—C14—S2	62.6 (2)
C13—C8—C9—C10	−0.5 (4)	C15—S2—C14—N7	15.35 (14)
C8—C9—C10—C11	0.5 (4)	C15—S2—C14—C11	−107.73 (16)
C9—C10—C11—C12	0.1 (3)	N7—N6—C15—N5	−178.19 (17)
C9—C10—C11—C14	180.0 (2)	N7—N6—C15—S2	0.2 (2)
C10—C11—C12—C13	−0.8 (4)	C16—N5—C15—N6	−174.9 (2)
C14—C11—C12—C13	179.4 (2)	C16—N5—C15—S2	6.8 (3)
F1—C8—C13—C12	179.5 (3)	C14—S2—C15—N6	−10.22 (18)
C9—C8—C13—C12	−0.1 (5)	C14—S2—C15—N5	168.13 (18)
C11—C12—C13—C8	0.7 (4)	C15—N5—C16—O3	4.0 (4)
C18—N7—C14—C11	−81.0 (2)	C15—N5—C16—C17	−175.6 (2)
N6—N7—C14—C11	102.1 (2)	N6—N7—C18—O4	179.87 (18)
C18—N7—C14—S2	156.79 (16)	C14—N7—C18—O4	3.2 (3)
N6—N7—C14—S2	−20.1 (2)	N6—N7—C18—C19	−0.6 (3)
C10—C11—C14—N7	126.2 (2)	C14—N7—C18—C19	−177.34 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O4ⁱ	0.86	1.96	2.815 (2)	171
C10—H10···O3ⁱⁱ	0.93	2.58	3.267 (3)	131
C17—H17A···O4ⁱ	0.96	2.46	3.316 (3)	148
C19—H19B···O4ⁱⁱⁱ	0.96	2.55	3.335 (3)	139

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₂FN₃O₂S
M_r	281.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.5061 (6), 11.2152 (7), 12.7752 (7)
β (°)	101.823 (4)
V (Å³)	1333.11 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.24 × 0.20 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.770, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11372, 2352, 2035
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.121, 1.07
No. of reflections	2352
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.34

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O4ⁱ	0.86	1.96	2.815 (2)	171.00
C10—H10···O3ⁱⁱ	0.93	2.58	3.267 (3)	131.00
C17—H17A···O4ⁱ	0.96	2.46	3.316 (3)	148.00
C19—H19B···O4ⁱⁱⁱ	0.96	2.55	3.335 (3)	139.00

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

Acknowledgements

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the X-ray data collection.

References

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