6-Bromo-1-ethyl-1H-2,1-benzothia­zin-4(3H)-one 2,2-dioxide

Shafiq, M.; Tahir, M.N.; Khan, I.U.; Arshad, M.N.; Safdar, M.

doi:10.1107/S1600536809002621

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o393

doi:10.1107/S1600536809002621

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6-Bromo-1-ethyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide

Muhammad Shafiq,^a M. Nawaz Tahir,^b ^* Islam Ullah Khan,^a Muhammad Nadeem Arshad ^a and Muhammad Safdar ^c

^aGovernment College University, Department of Chemistry, Lahore, Pakistan, ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and ^cUniversity of Karachi, HEJ research Institute of Chemistry, Karachi, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 19 January 2009; accepted 21 January 2009; online 28 January 2009)

In the title compound, C₁₀H₁₀BrNO₃S, the S atom is four-coordinated in a distorted tetrahedral configuration with nearly equal S=O bond distances; the S—C and S—N bond lengths are 1.755 (3) and 1.649 (3) Å, respectively. The heterocyclic thiazine ring adopts a twist conformation. Adjacent molecules are attached to each other through intermolecular C—H⋯O hydrogen bonds, forming R₂²(8) and R₂²(14) ring motifs. The molecules are stabilized by intra- and intermolecular hydrogen bonds, forming a three-dimensional polymeric network.

Related literature

For previous work on benzothiazines, see: Arshad et al. (2008 ); Shafiq, Khan et al. (2008 ); Shafiq, Tahir et al. (2008 ); Tahir et al. (2008 ). For puckering parameters, see: Cremer & Pople (1975 ). For graph-set motifs, see: Bernstein et al. (1995 ). For synthesis, see: Lombardino (1972 ).

Experimental

Crystal data

C₁₀H₁₀BrNO₃S
M_r = 304.16
Triclinic, $[P \overline 1]$
a = 7.7164 (2) Å
b = 7.9729 (3) Å
c = 10.4579 (3) Å
α = 86.767 (2)°
β = 75.773 (1)°
γ = 66.912 (2)°
V = 573.13 (3) Å³
Z = 2
Mo Kα radiation
μ = 3.76 mm⁻¹
T = 296 (2) K
0.28 × 0.16 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.486, T_max = 0.639
12369 measured reflections
2846 independent reflections
1840 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.095
S = 1.02
2846 reflections
158 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.91 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.9300	2.4200	3.324 (4)	165.00
C3—H3⋯O2ⁱⁱ	0.9300	2.5900	3.418 (4)	148.00
C8—H8A⋯O3ⁱⁱⁱ	0.89 (4)	2.57 (4)	3.252 (4)	134 (3)
C9—H9B⋯O3	0.93 (3)	2.29 (3)	2.850 (4)	118 (2)
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+1, -z; (iii) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: APEX2; 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: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809002621/at2711sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002621/at2711Isup2.hkl

checkCIF report

Comment top

Our group is involved in synthesizing various derivatives of benzothiazine molecule (Shafiq, Khan et al., 2008; Shafiq, Tahir et al., 2008; Tahir et al., 2008; Arshad et al., 2008) and their characterization by X-ray studies. We, here, report the title compound (I), (Fig 1), in this context.

In the title compound, the bromo-substituated benzene ring A (C1–C6), is almost planar with alternate distortions at individual C atoms. The Br atom is at a distance of 0.073 (4) Å from the r.m.s. plane of ring A. The thiazine ring B (S1/N1/C1/C6–C8) is in the twisted form. The maximum puckering (Cremer & Pople, 1975) amplitude, Q_T, of ring A and ring B is 0.674 (2) Å. There exist an intramolecular H-bond of C—H···O type between the methylene group and the SO₂ moiety. The intermolecular H-bonds [C8—H8A···.O3] and [C3—H3···.O2] (Table 1), joint the adjacent molecules forming ring motifs, (Bernstein et al., 1995), R₂²(8) and R₂²(14), respectively. The three asymmetric units joint in this way, are further linked through [C2—H2···O1] H-bonds with carbonyl moiety (Fig 2).

Related literature top

For previous work on benzothiazines, see: Arshad et al. (2008); Shafiq, Khan et al. (2008); Shafiq, Tahir et al. (2008); Tahir et al. (2008). For puckering parameters, see: Cremer & Pople (1975). For graph-set motifs, see: Bernstein et al. (1995). For synthesis, see: Lombardino (1972). [Please check rephrasing]

Experimental top

The title compound was prepared in a three step scheme following the reported procedure (Lombardino, 1972). Starting material used was methyl-2-amino-5-bromo benzoate. It was reacted with methane sulfonyl chloride taking equimolar quantities, in dichloromethane. The pH was kept alkaline with triethylamine. The product of this step was then N-ethylated (ethyl iodide) and cyclized as reported in the above mentioned reference, to get the title compound which was recrystallized in ethanol for X-ray diffraction studies.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top

	Fig. 1. ORTEP drawing of the title compound, with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H atoms are shown by small circles of arbitrary radii. The dotted line shows the intramolecular H-bond.
	Fig. 2. The partial packing figure (PLATON: Spek, 2003) which shows that intermolecular H-bonds form the ring motifs.

6-Bromo-1-ethyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide top

Crystal data top

C₁₀H₁₀BrNO₃S	Z = 2
M_r = 304.16	F(000) = 304
Triclinic, P1	D_x = 1.762 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7164 (2) Å	Cell parameters from 2847 reflections
b = 7.9729 (3) Å	θ = 2.0–28.3°
c = 10.4579 (3) Å	µ = 3.76 mm⁻¹
α = 86.767 (2)°	T = 296 K
β = 75.773 (1)°	Needle, colourless
γ = 66.912 (2)°	0.28 × 0.16 × 0.12 mm
V = 573.13 (3) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	2846 independent reflections
Radiation source: fine-focus sealed tube	1840 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.3°, θ_min = 2.0°
ω scans	h = −10→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
T_min = 0.486, T_max = 0.639	l = −13→13
12369 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0388P)² + 0.3304P] where P = (F_o² + 2F_c²)/3
2846 reflections	(Δ/σ)_max = 0.001
158 parameters	Δρ_max = 0.91 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

C₁₀H₁₀BrNO₃S	γ = 66.912 (2)°
M_r = 304.16	V = 573.13 (3) Å³
Triclinic, P1	Z = 2
a = 7.7164 (2) Å	Mo Kα radiation
b = 7.9729 (3) Å	µ = 3.76 mm⁻¹
c = 10.4579 (3) Å	T = 296 K
α = 86.767 (2)°	0.28 × 0.16 × 0.12 mm
β = 75.773 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2846 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1840 reflections with I > 2σ(I)
T_min = 0.486, T_max = 0.639	R_int = 0.034
12369 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.91 e Å⁻³
2846 reflections	Δρ_min = −0.58 e Å⁻³
158 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 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
Br1	0.36240 (6)	0.15247 (6)	−0.35948 (3)	0.0686 (2)
S1	−0.00069 (12)	0.19519 (10)	0.32296 (7)	0.0435 (3)
O1	0.2170 (4)	−0.2056 (3)	0.0770 (3)	0.0705 (10)
O2	−0.1737 (3)	0.2464 (3)	0.2787 (2)	0.0578 (8)
O3	−0.0156 (4)	0.2267 (3)	0.4583 (2)	0.0668 (10)
N1	0.1437 (4)	0.2891 (3)	0.2351 (2)	0.0450 (9)
C1	0.1999 (4)	0.2535 (4)	0.0977 (3)	0.0358 (9)
C2	0.2376 (5)	0.3826 (4)	0.0126 (3)	0.0444 (10)
C3	0.2876 (5)	0.3511 (4)	−0.1214 (3)	0.0471 (11)
C4	0.3017 (4)	0.1895 (4)	−0.1739 (3)	0.0423 (10)
C5	0.2710 (4)	0.0580 (4)	−0.0934 (3)	0.0416 (10)
C6	0.2210 (4)	0.0869 (4)	0.0432 (3)	0.0361 (9)
C7	0.1935 (4)	−0.0623 (4)	0.1248 (3)	0.0427 (10)
C8	0.1398 (6)	−0.0343 (4)	0.2718 (3)	0.0493 (11)
C9	0.1564 (5)	0.4465 (4)	0.2950 (3)	0.0465 (11)
C10	0.3622 (5)	0.4137 (5)	0.2925 (4)	0.0635 (14)
H2	0.22872	0.49140	0.04727	0.0533*
H3	0.31214	0.43846	−0.17724	0.0564*
H5	0.28342	−0.05116	−0.12983	0.0499*
H8A	0.065 (5)	−0.092 (5)	0.313 (4)	0.0591*
H8B	0.247 (5)	−0.063 (5)	0.306 (3)	0.0591*
H9A	0.092 (5)	0.550 (5)	0.245 (3)	0.0558*
H9B	0.085 (5)	0.457 (4)	0.382 (3)	0.0558*
H10A	0.43344	0.41151	0.20285	0.0948*
H10B	0.36403	0.50981	0.34278	0.0948*
H10C	0.42109	0.29879	0.33010	0.0948*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0779 (3)	0.0861 (3)	0.0329 (2)	−0.0249 (2)	−0.0092 (2)	0.0002 (2)
S1	0.0540 (5)	0.0443 (4)	0.0344 (4)	−0.0260 (4)	−0.0036 (3)	0.0030 (3)
O1	0.113 (2)	0.0401 (13)	0.0672 (17)	−0.0416 (15)	−0.0168 (15)	−0.0010 (12)
O2	0.0464 (14)	0.0583 (14)	0.0673 (16)	−0.0232 (12)	−0.0074 (12)	0.0063 (12)
O3	0.098 (2)	0.0734 (16)	0.0341 (13)	−0.0463 (15)	−0.0033 (12)	0.0009 (11)
N1	0.0626 (17)	0.0467 (14)	0.0332 (14)	−0.0347 (14)	−0.0012 (12)	−0.0045 (11)
C1	0.0391 (16)	0.0356 (15)	0.0340 (16)	−0.0178 (13)	−0.0056 (12)	−0.0001 (12)
C2	0.0552 (19)	0.0351 (15)	0.0453 (19)	−0.0238 (15)	−0.0057 (15)	0.0010 (13)
C3	0.051 (2)	0.0462 (18)	0.0429 (19)	−0.0212 (16)	−0.0075 (15)	0.0110 (15)
C4	0.0425 (18)	0.0510 (18)	0.0307 (16)	−0.0164 (15)	−0.0074 (13)	0.0015 (14)
C5	0.0439 (18)	0.0377 (16)	0.0418 (18)	−0.0139 (14)	−0.0098 (14)	−0.0056 (14)
C6	0.0419 (17)	0.0324 (15)	0.0369 (16)	−0.0182 (13)	−0.0082 (13)	0.0005 (12)
C7	0.0487 (19)	0.0354 (16)	0.0491 (19)	−0.0198 (14)	−0.0158 (15)	0.0050 (14)
C8	0.061 (2)	0.0436 (18)	0.047 (2)	−0.0254 (18)	−0.0137 (17)	0.0121 (15)
C9	0.056 (2)	0.0423 (17)	0.0440 (19)	−0.0255 (17)	−0.0033 (16)	−0.0115 (15)
C10	0.065 (2)	0.066 (2)	0.071 (3)	−0.033 (2)	−0.023 (2)	−0.004 (2)

Geometric parameters (Å, º) top

Br1—C4	1.893 (3)	C6—C7	1.477 (4)
S1—O2	1.421 (3)	C7—C8	1.496 (4)
S1—O3	1.420 (2)	C9—C10	1.499 (6)
S1—N1	1.649 (3)	C2—H2	0.9300
S1—C8	1.755 (3)	C3—H3	0.9300
O1—C7	1.202 (4)	C5—H5	0.9300
N1—C1	1.406 (4)	C8—H8A	0.89 (4)
N1—C9	1.481 (4)	C8—H8B	0.92 (4)
C1—C2	1.393 (4)	C9—H9A	0.98 (4)
C1—C6	1.409 (4)	C9—H9B	0.93 (3)
C2—C3	1.369 (4)	C10—H10A	0.9600
C3—C4	1.383 (4)	C10—H10B	0.9600
C4—C5	1.364 (4)	C10—H10C	0.9600
C5—C6	1.393 (4)

Br1···Br1ⁱ	3.5704 (5)	C2···H9A	2.61 (3)
Br1···H8Bⁱⁱ	3.00 (4)	C2···H10A	2.8500
O1···C2ⁱⁱⁱ	3.324 (4)	C9···H2	2.5500
O2···C6	3.254 (4)	C10···H2	2.9400
O2···C10^iv	3.263 (5)	H2···O1^ix	2.4200
O2···C3^v	3.418 (4)	H2···C9	2.5500
O3···C8^vi	3.252 (4)	H2···C10	2.9400
O1···H9Aⁱⁱⁱ	2.84 (4)	H2···H9A	2.0600
O1···H2ⁱⁱⁱ	2.4200	H2···H10A	2.4300
O1···H5	2.4700	H3···O2^v	2.5900
O2···H10C^iv	2.9000	H5···O1	2.4700
O2···H5^vii	2.7400	H5···O2^vii	2.7400
O2···H3^v	2.5900	H8A···O3^vi	2.57 (4)
O3···H9B	2.29 (3)	H8B···Br1ⁱⁱ	3.00 (4)
O3···H8A^vi	2.57 (4)	H9A···O1^ix	2.84 (4)
O3···H9B^viii	2.90 (3)	H9A···C2	2.61 (3)
C2···O1^ix	3.324 (4)	H9A···H2	2.0600
C2···C10	3.348 (5)	H9B···O3	2.29 (3)
C2···C2^v	3.472 (5)	H9B···O3^viii	2.90 (3)
C3···O2^v	3.418 (4)	H9B···H9B^viii	2.49 (4)
C6···O2	3.254 (4)	H10A···C1	2.9900
C8···O3^vi	3.252 (4)	H10A···C2	2.8500
C10···C2	3.348 (5)	H10A···H2	2.4300
C10···O2^x	3.263 (5)	H10C···O2^x	2.9000
C1···H10A	2.9900

O2—S1—O3	118.87 (16)	S1—C8—C7	112.1 (2)
O2—S1—N1	110.91 (14)	N1—C9—C10	111.6 (3)
O2—S1—C8	106.97 (18)	C1—C2—H2	120.00
O3—S1—N1	107.50 (16)	C3—C2—H2	120.00
O3—S1—C8	111.51 (15)	C2—C3—H3	120.00
N1—S1—C8	99.36 (16)	C4—C3—H3	120.00
S1—N1—C1	117.1 (2)	C4—C5—H5	120.00
S1—N1—C9	118.39 (19)	C6—C5—H5	120.00
C1—N1—C9	121.6 (2)	S1—C8—H8A	104 (2)
N1—C1—C2	120.3 (3)	S1—C8—H8B	104 (2)
N1—C1—C6	121.0 (3)	C7—C8—H8A	113 (3)
C2—C1—C6	118.7 (3)	C7—C8—H8B	112 (2)
C1—C2—C3	120.7 (3)	H8A—C8—H8B	111 (3)
C2—C3—C4	120.1 (3)	N1—C9—H9A	104 (2)
Br1—C4—C3	119.3 (2)	N1—C9—H9B	105 (2)
Br1—C4—C5	120.0 (2)	C10—C9—H9A	115 (2)
C3—C4—C5	120.7 (3)	C10—C9—H9B	110 (3)
C4—C5—C6	120.1 (3)	H9A—C9—H9B	111 (3)
C1—C6—C5	119.6 (3)	C9—C10—H10A	109.00
C1—C6—C7	122.9 (3)	C9—C10—H10B	110.00
C5—C6—C7	117.4 (3)	C9—C10—H10C	109.00
O1—C7—C6	122.2 (3)	H10A—C10—H10B	109.00
O1—C7—C8	119.4 (3)	H10A—C10—H10C	109.00
C6—C7—C8	118.4 (3)	H10B—C10—H10C	109.00

O2—S1—N1—C1	−56.8 (3)	N1—C1—C6—C5	178.0 (3)
O2—S1—N1—C9	104.3 (2)	N1—C1—C6—C7	−2.4 (5)
O3—S1—N1—C1	171.7 (2)	C2—C1—C6—C5	−2.6 (5)
O3—S1—N1—C9	−27.2 (3)	C2—C1—C6—C7	177.1 (3)
C8—S1—N1—C1	55.5 (3)	C1—C2—C3—C4	−0.2 (6)
C8—S1—N1—C9	−143.4 (3)	C2—C3—C4—Br1	177.9 (3)
O2—S1—C8—C7	61.0 (3)	C2—C3—C4—C5	−1.7 (6)
O3—S1—C8—C7	−167.5 (3)	Br1—C4—C5—C6	−178.2 (3)
N1—S1—C8—C7	−54.3 (3)	C3—C4—C5—C6	1.3 (5)
S1—N1—C1—C2	149.4 (3)	C4—C5—C6—C1	0.8 (5)
S1—N1—C1—C6	−31.2 (4)	C4—C5—C6—C7	−178.8 (3)
C9—N1—C1—C2	−11.1 (5)	C1—C6—C7—O1	−178.0 (3)
C9—N1—C1—C6	168.3 (3)	C1—C6—C7—C8	0.4 (5)
S1—N1—C9—C10	125.2 (3)	C5—C6—C7—O1	1.7 (5)
C1—N1—C9—C10	−74.6 (4)	C5—C6—C7—C8	180.0 (3)
N1—C1—C2—C3	−178.3 (3)	O1—C7—C8—S1	−150.2 (3)
C6—C1—C2—C3	2.2 (5)	C6—C7—C8—S1	31.4 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1^ix	0.9300	2.4200	3.324 (4)	165.00
C3—H3···O2^v	0.9300	2.5900	3.418 (4)	148.00
C8—H8A···O3^vi	0.89 (4)	2.57 (4)	3.252 (4)	134 (3)
C9—H9B···O3	0.93 (3)	2.29 (3)	2.850 (4)	118 (2)

Symmetry codes: (v) −x, −y+1, −z; (vi) −x, −y, −z+1; (ix) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀BrNO₃S
M_r	304.16
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.7164 (2), 7.9729 (3), 10.4579 (3)
α, β, γ (°)	86.767 (2), 75.773 (1), 66.912 (2)
V (Å³)	573.13 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.76
Crystal size (mm)	0.28 × 0.16 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.486, 0.639
No. of measured, independent and observed [I > 2σ(I)] reflections	12369, 2846, 1840
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.095, 1.02
No. of reflections	2846
No. of parameters	158
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.91, −0.58

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.9300	2.4200	3.324 (4)	165.00
C3—H3···O2ⁱⁱ	0.9300	2.5900	3.418 (4)	148.00
C8—H8A···O3ⁱⁱⁱ	0.89 (4)	2.57 (4)	3.252 (4)	134 (3)
C9—H9B···O3	0.93 (3)	2.29 (3)	2.850 (4)	118 (2)

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

Acknowledgements

M. Shafiq gratefully acknowledges the Higher Education Commision, Islamabad, Pakistan, for providing a Scholarship under the Indigenous PhD Programme (PIN 042-120567-PS2-276).

References

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