Methyl 4-hydr­oxy-2-propyl-2H-1,2-benzothia­zine-3-carboxyl­ate 1,1-dioxide

Arshad, M.N.; Zia-ur-Rehman, M.; Khan, I.U.

doi:10.1107/S1600536809046236

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3025

doi:10.1107/S1600536809046236

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Methyl 4-hydroxy-2-propyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Muhammad Nadeem Arshad,^a Muhammad Zia-ur-Rehman ^b and Islam Ullah Khan ^a ^*

^aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore 54600, Pakistan
^*Correspondence e-mail: iukhan.gcu@gmail.com

(Received 2 November 2009; accepted 3 November 2009; online 7 November 2009)

In the title compound, C₁₃H₁₅NO₅S, the thiazine ring adopts a distorted half-chair conformation. The enolic H atom is involved in an intramolecular O—H⋯O hydrogen bond, forming a six-membered ring. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds, resulting in zigzag chains lying along the c axis.

Related literature

For the syntheses of related compounds, see: Bihovsky et al. (2004 ); Braun (1923 ); Lombardino et al. (1971 ); Zia-ur-Rehman et al. (2005 , 2009 ). For the biological activity of benzothiazines, see: Turck et al. (1996 ); Zia-ur-Rehman et al. (2006 ). For related structures, see: Fabiola et al. (1998 ); Zia-ur-Rehman et al. (2007 ).

Experimental

Crystal data

C₁₃H₁₅NO₅S
M_r = 297.32
Orthorhombic, P c a 2₁
a = 12.4398 (6) Å
b = 8.7538 (5) Å
c = 12.7288 (7) Å
V = 1386.11 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.39 × 0.36 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.908, T_max = 0.973
8843 measured reflections
3252 independent reflections
2540 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.094
S = 1.03
3252 reflections
184 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 1451 Friedel pairs
Flack parameter: −0.08 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O4	0.82	1.84	2.558 (2)	145
C3—H3⋯O2ⁱ	0.93	2.48	3.358 (3)	158
Symmetry code: (i) $[-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046236/is2482sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046236/is2482Isup2.hkl

checkCIF report

Comment top

Benzothiazine1,1-dioxides are known to possess a versatile range of biological activities and have been synthesized continuously since the very first synthesis in 1923 (Braun, 1923). Among these, Piroxicam (Lombardino et al., 1971; Zia-ur-Rehman et al., 2005), and Meloxicam (Turck et al., 1996) are familiar for their analgesic and anti-inflammatory activities and are being used world wide as non-steroidal anti-inflammatory drugs (NSAIDs). Few of its derivatives are also known as potent calpain I inhibitors (Bihovsky et al., 2004), while benzothiaine-3-yl-quinazolin-4-ones showed marked activity against Bacillus subtilis (Zia-ur-Rehman et al., 2006). As part of a research program synthesizing various bioactive benzothiazines (Zia-ur-Rehman et al., 2005, 2006, 2009), we herein report the crystal structure of the title compound, (I).

In the molecule of the title compound (Fig. 1), the thiazine ring exhibits a distorted half-chair conformation with S1/C1/C6/C7 atoms lying in a plane and N1 showing significant departure from the plane due to its pyramidal geometry projecting the propyl group approximately perpendicular to the ring. Like other 1,2-benzothiazine 1,1-dioxide derivatives (Fabiola et al., 1998; Zia-ur-Rehman et al., 2007), the enolic hydrogen on O3 is involved in intramolecular hydrogen bonding (Table1). Also, C7—C8 bond length [1.346 (3) Å] (very close to normal C—C bond 1.36 Å) indicates a partial double-bond character indicating the dominance of enolic form in the molecule. The C1—S1 bond distance [1.759 (3) Å] is as expected for typical C(sp2)—S bond (1.751 Å). Each molecule is linked to neighbouring molecules via weaker C—H···O=S interactions giving rise to zigzag chains along the c axis (Fig. 2).

Related literature top

For the syntheses of related compounds, see: Bihovsky et al. (2004); Braun (1923); Lombardino et al. (1971); Zia-ur-Rehman et al. (2005, 2009). For the biological activity of benzothiazines, see: Turck et al. (1996); Zia-ur-Rehman et al. (2006). For related structures, see: Fabiola et al. (1998); Zia-ur-Rehman et al. (2007).

Experimental top

Propyl iodide (5.10 g, 30.0 mmol) was added drop wise to the mixture of methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide (3.83 g, 15.0 mmol), anhydrous potassium carbonate (1.68 g, 30.0 mmol) and dimethylformamide (20.0 ml) in a round bottom flask. Contents were stirred at room temperature for 7 h under nitrogen atmosphere and poured over ice cooled water (300 ml) resulting in an immediate formation of a white solid, which was filtered and washed with cold water. Crystallization from methanol yielded pure compound.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids at the 50% probability level.
	Fig. 2. Perspective view of the crystal packing showing C—H···O hydrogen-bonded interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

Methyl 4-hydroxy-2-propyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide top

Crystal data top

C₁₃H₁₅NO₅S	F(000) = 624
M_r = 297.32	D_x = 1.425 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2980 reflections
a = 12.4398 (6) Å	θ = 2.3–25.3°
b = 8.7538 (5) Å	µ = 0.25 mm⁻¹
c = 12.7288 (7) Å	T = 296 K
V = 1386.11 (13) Å³	Rods, yellow
Z = 4	0.39 × 0.36 × 0.11 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3252 independent reflections
Radiation source: fine-focus sealed tube	2540 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→10
T_min = 0.908, T_max = 0.973	k = −11→11
8843 measured reflections	l = −16→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0496P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3252 reflections	Δρ_max = 0.16 e Å⁻³
184 parameters	Δρ_min = −0.22 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1451 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.08 (8)

Crystal data top

C₁₃H₁₅NO₅S	V = 1386.11 (13) Å³
M_r = 297.32	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 12.4398 (6) Å	µ = 0.25 mm⁻¹
b = 8.7538 (5) Å	T = 296 K
c = 12.7288 (7) Å	0.39 × 0.36 × 0.11 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3252 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2540 reflections with I > 2σ(I)
T_min = 0.908, T_max = 0.973	R_int = 0.028
8843 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.094	Δρ_max = 0.16 e Å⁻³
S = 1.03	Δρ_min = −0.22 e Å⁻³
3252 reflections	Absolute structure: Flack (1983), 1451 Friedel pairs
184 parameters	Absolute structure parameter: −0.08 (8)
1 restraint

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
C1	0.58950 (17)	0.7963 (3)	0.8319 (2)	0.0442 (5)
C2	0.66903 (18)	0.8114 (3)	0.7577 (2)	0.0565 (6)
H2	0.7391	0.7816	0.7726	0.068*
C3	0.6434 (2)	0.8714 (3)	0.6609 (3)	0.0703 (8)
H3	0.6967	0.8829	0.6103	0.084*
C4	0.5396 (2)	0.9145 (3)	0.6385 (2)	0.0622 (7)
H4	0.5230	0.9536	0.5725	0.075*
C5	0.45981 (19)	0.9001 (3)	0.71319 (19)	0.0509 (6)
H5	0.3900	0.9308	0.6976	0.061*
C6	0.48305 (15)	0.8403 (3)	0.81103 (17)	0.0407 (5)
C7	0.39979 (15)	0.8187 (3)	0.89165 (18)	0.0398 (5)
C8	0.40966 (15)	0.7206 (2)	0.97246 (19)	0.0389 (5)
C9	0.32273 (17)	0.7043 (3)	1.04807 (18)	0.0443 (5)
C10	0.2568 (3)	0.5866 (3)	1.2006 (3)	0.0755 (8)
H10A	0.1955	0.5455	1.1645	0.113*
H10B	0.2378	0.6825	1.2322	0.113*
H10C	0.2794	0.5165	1.2542	0.113*
C11	0.50112 (17)	0.4660 (3)	0.9658 (2)	0.0493 (5)
H11A	0.4465	0.4214	1.0107	0.059*
H11B	0.5695	0.4204	0.9848	0.059*
C12	0.4761 (2)	0.4257 (3)	0.8530 (2)	0.0589 (7)
H12A	0.5279	0.4748	0.8072	0.071*
H12B	0.4052	0.4639	0.8350	0.071*
C13	0.4794 (3)	0.2548 (3)	0.8355 (3)	0.0812 (10)
H13A	0.4297	0.2057	0.8823	0.122*
H13B	0.5507	0.2178	0.8490	0.122*
H13C	0.4600	0.2325	0.7641	0.122*
N1	0.50637 (13)	0.6325 (2)	0.98684 (13)	0.0423 (5)
O1	0.70303 (11)	0.6188 (2)	0.95391 (16)	0.0633 (5)
O2	0.62415 (13)	0.8534 (2)	1.02728 (17)	0.0676 (6)
O3	0.31275 (12)	0.90699 (18)	0.87688 (13)	0.0532 (4)
H3A	0.2671	0.8861	0.9211	0.080*
O4	0.23788 (13)	0.7728 (2)	1.03972 (15)	0.0586 (5)
O5	0.34308 (13)	0.60963 (19)	1.12699 (13)	0.0547 (4)
S1	0.61649 (4)	0.72551 (7)	0.95848 (6)	0.04848 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0361 (10)	0.0384 (12)	0.0580 (13)	−0.0019 (9)	0.0015 (10)	−0.0081 (10)
C2	0.0407 (13)	0.0523 (15)	0.0765 (17)	−0.0002 (11)	0.0107 (12)	−0.0006 (13)
C3	0.0666 (18)	0.0632 (18)	0.081 (2)	0.0040 (15)	0.0342 (15)	0.0044 (15)
C4	0.0709 (17)	0.0561 (17)	0.0595 (16)	0.0069 (13)	0.0155 (14)	0.0104 (13)
C5	0.0502 (13)	0.0437 (14)	0.0587 (15)	0.0032 (10)	0.0017 (11)	0.0047 (11)
C6	0.0369 (10)	0.0354 (12)	0.0499 (13)	−0.0005 (9)	0.0016 (9)	−0.0056 (10)
C7	0.0322 (10)	0.0402 (12)	0.0471 (12)	0.0021 (8)	−0.0027 (9)	−0.0072 (9)
C8	0.0315 (8)	0.0412 (11)	0.0439 (14)	0.0042 (8)	−0.0029 (9)	−0.0057 (10)
C9	0.0403 (12)	0.0447 (12)	0.0480 (12)	0.0016 (10)	0.0004 (10)	−0.0040 (11)
C10	0.0678 (16)	0.095 (2)	0.0642 (17)	0.0176 (16)	0.0203 (13)	0.0219 (18)
C11	0.0443 (10)	0.0444 (12)	0.0592 (13)	0.0112 (9)	−0.0031 (11)	0.0016 (13)
C12	0.0590 (14)	0.0499 (16)	0.0677 (17)	−0.0024 (11)	−0.0011 (13)	−0.0091 (12)
C13	0.077 (2)	0.059 (2)	0.107 (3)	−0.0003 (14)	0.0020 (18)	−0.0210 (19)
N1	0.0350 (9)	0.0465 (11)	0.0455 (12)	0.0077 (7)	−0.0061 (7)	−0.0044 (8)
O1	0.0354 (7)	0.0806 (12)	0.0740 (11)	0.0161 (7)	−0.0059 (9)	−0.0045 (11)
O2	0.0468 (10)	0.0802 (14)	0.0760 (12)	−0.0004 (8)	−0.0149 (8)	−0.0329 (11)
O3	0.0378 (8)	0.0548 (10)	0.0669 (11)	0.0137 (7)	0.0065 (7)	0.0114 (8)
O4	0.0413 (9)	0.0678 (11)	0.0669 (11)	0.0144 (8)	0.0100 (8)	0.0109 (9)
O5	0.0484 (9)	0.0677 (11)	0.0480 (9)	0.0105 (8)	0.0071 (7)	0.0092 (8)
S1	0.0309 (2)	0.0583 (3)	0.0562 (3)	0.0046 (2)	−0.0086 (3)	−0.0146 (3)

Geometric parameters (Å, º) top

C1—C2	1.374 (3)	C10—O5	1.439 (3)
C1—C6	1.404 (3)	C10—H10A	0.9600
C1—S1	1.759 (3)	C10—H10B	0.9600
C2—C3	1.376 (4)	C10—H10C	0.9600
C2—H2	0.9300	C11—N1	1.483 (3)
C3—C4	1.375 (4)	C11—C12	1.511 (4)
C3—H3	0.9300	C11—H11A	0.9700
C4—C5	1.380 (3)	C11—H11B	0.9700
C4—H4	0.9300	C12—C13	1.513 (4)
C5—C6	1.382 (3)	C12—H12A	0.9700
C5—H5	0.9300	C12—H12B	0.9700
C6—C7	1.470 (3)	C13—H13A	0.9600
C7—O3	1.344 (2)	C13—H13B	0.9600
C7—C8	1.346 (3)	C13—H13C	0.9600
C8—N1	1.441 (3)	N1—S1	1.6339 (19)
C8—C9	1.455 (3)	O1—S1	1.4268 (15)
C9—O4	1.219 (3)	O2—S1	1.425 (2)
C9—O5	1.327 (3)	O3—H3A	0.8200

C2—C1—C6	121.5 (2)	H10A—C10—H10C	109.5
C2—C1—S1	121.76 (19)	H10B—C10—H10C	109.5
C6—C1—S1	116.72 (17)	N1—C11—C12	114.2 (2)
C1—C2—C3	119.0 (2)	N1—C11—H11A	108.7
C1—C2—H2	120.5	C12—C11—H11A	108.7
C3—C2—H2	120.5	N1—C11—H11B	108.7
C4—C3—C2	120.5 (2)	C12—C11—H11B	108.7
C4—C3—H3	119.7	H11A—C11—H11B	107.6
C2—C3—H3	119.7	C11—C12—C13	111.4 (2)
C3—C4—C5	120.5 (3)	C11—C12—H12A	109.3
C3—C4—H4	119.8	C13—C12—H12A	109.3
C5—C4—H4	119.8	C11—C12—H12B	109.3
C4—C5—C6	120.4 (2)	C13—C12—H12B	109.3
C4—C5—H5	119.8	H12A—C12—H12B	108.0
C6—C5—H5	119.8	C12—C13—H13A	109.5
C5—C6—C1	118.1 (2)	C12—C13—H13B	109.5
C5—C6—C7	122.04 (19)	H13A—C13—H13B	109.5
C1—C6—C7	119.8 (2)	C12—C13—H13C	109.5
O3—C7—C8	123.2 (2)	H13A—C13—H13C	109.5
O3—C7—C6	113.3 (2)	H13B—C13—H13C	109.5
C8—C7—C6	123.46 (18)	C8—N1—C11	117.79 (16)
C7—C8—N1	120.99 (19)	C8—N1—S1	113.92 (15)
C7—C8—C9	120.03 (18)	C11—N1—S1	119.13 (14)
N1—C8—C9	118.98 (19)	C7—O3—H3A	109.5
O4—C9—O5	122.6 (2)	C9—O5—C10	115.99 (19)
O4—C9—C8	122.6 (2)	O2—S1—O1	119.30 (11)
O5—C9—C8	114.85 (18)	O2—S1—N1	108.17 (11)
O5—C10—H10A	109.5	O1—S1—N1	108.37 (10)
O5—C10—H10B	109.5	O2—S1—C1	107.40 (13)
H10A—C10—H10B	109.5	O1—S1—C1	109.72 (11)
O5—C10—H10C	109.5	N1—S1—C1	102.59 (9)

C6—C1—C2—C3	0.1 (4)	N1—C8—C9—O5	1.8 (3)
S1—C1—C2—C3	−178.3 (2)	N1—C11—C12—C13	176.1 (2)
C1—C2—C3—C4	−0.5 (4)	C7—C8—N1—C11	−108.9 (2)
C2—C3—C4—C5	0.9 (4)	C9—C8—N1—C11	72.3 (3)
C3—C4—C5—C6	−0.9 (4)	C7—C8—N1—S1	37.8 (3)
C4—C5—C6—C1	0.5 (3)	C9—C8—N1—S1	−141.04 (17)
C4—C5—C6—C7	−178.1 (2)	C12—C11—N1—C8	63.6 (3)
C2—C1—C6—C5	−0.1 (3)	C12—C11—N1—S1	−81.3 (2)
S1—C1—C6—C5	178.34 (18)	O4—C9—O5—C10	2.7 (3)
C2—C1—C6—C7	178.5 (2)	C8—C9—O5—C10	−177.5 (2)
S1—C1—C6—C7	−3.0 (3)	C8—N1—S1—O2	61.60 (18)
C5—C6—C7—O3	−21.8 (3)	C11—N1—S1—O2	−152.19 (18)
C1—C6—C7—O3	159.7 (2)	C8—N1—S1—O1	−167.73 (15)
C5—C6—C7—C8	158.4 (2)	C11—N1—S1—O1	−21.5 (2)
C1—C6—C7—C8	−20.2 (3)	C8—N1—S1—C1	−51.72 (16)
O3—C7—C8—N1	−177.71 (19)	C11—N1—S1—C1	94.49 (18)
C6—C7—C8—N1	2.1 (3)	C2—C1—S1—O2	100.0 (2)
O3—C7—C8—C9	1.1 (3)	C6—C1—S1—O2	−78.46 (19)
C6—C7—C8—C9	−179.1 (2)	C2—C1—S1—O1	−31.1 (2)
C7—C8—C9—O4	2.6 (3)	C6—C1—S1—O1	150.46 (17)
N1—C8—C9—O4	−178.5 (2)	C2—C1—S1—N1	−146.1 (2)
C7—C8—C9—O5	−177.1 (2)	C6—C1—S1—N1	35.43 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4	0.82	1.84	2.558 (2)	145
C3—H3···O2ⁱ	0.93	2.48	3.358 (3)	158

Symmetry code: (i) −x+3/2, y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₅NO₅S
M_r	297.32
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	296
a, b, c (Å)	12.4398 (6), 8.7538 (5), 12.7288 (7)
V (Å³)	1386.11 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.39 × 0.36 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.908, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	8843, 3252, 2540
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.094, 1.03
No. of reflections	3252
No. of parameters	184
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.22
Absolute structure	Flack (1983), 1451 Friedel pairs
Absolute structure parameter	−0.08 (8)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4	0.82	1.84	2.558 (2)	145
C3—H3···O2ⁱ	0.93	2.48	3.358 (3)	158

Symmetry code: (i) −x+3/2, y, z−1/2.

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan and PCSIR Laboratories Complex for the provision of the diffractometer and chemicals, respectively.

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