Methyl 2,4-dihy­droxy-5-(4-nitro­benzamido)­benzoate

Naz, S.S.; Islam, N.U.; Tahir, M.N.; Shah, M.R.

doi:10.1107/S160053681300024X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o207

doi:10.1107/S160053681300024X

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Methyl 2,4-dihydroxy-5-(4-nitrobenzamido)benzoate

Syeda Sohaila Naz,^a Nazar Ul Islam,^a M. Nawaz Tahir ^b ^* and Muhammad Raza Shah ^c

^aUniversity of Peshawar, Institute of Chemical Sciences, Peshawar, Pakistan, ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and ^cH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 3 January 2013; accepted 3 January 2013; online 9 January 2013)

In the title compound, C₁₅H₁₂N₂O₇, the dihedral angle between the aromatic rings is 4.58 (13)° and the nitro group is rotated from its attached ring by 18.07 (17)°. Intramolecular N—H⋯O and O—H⋯O hydrogen bonds generate S(5) and S(6) rings, respectively. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, generating [001] C(7) chains. The chains are linked by C—H⋯O interactions, forming a three-dimensional network, which incorporates R₂²(7) and R₂²(10) loops.

Related literature

For a related structure, see: Gorelik et al. (2010 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₂N₂O₇
M_r = 332.27
Monoclinic, C 2/c
a = 30.412 (6) Å
b = 6.9325 (15) Å
c = 14.936 (3) Å
β = 111.737 (8)°
V = 2925.0 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 K
0.28 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.970, T_max = 0.980
10681 measured reflections
2885 independent reflections
1519 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.134
S = 0.98
2885 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.86	2.16	2.595 (3)	111
O3—H3A⋯O2	0.82	1.91	2.619 (3)	144
O4—H4⋯O5ⁱ	0.82	1.86	2.670 (2)	170
C8—H8A⋯O3ⁱⁱ	0.96	2.51	3.274 (4)	137
C12—H12⋯O7ⁱⁱⁱ	0.93	2.38	3.297 (4)	171
C15—H15⋯O4ⁱⁱ	0.93	2.46	3.370 (3)	165
Symmetry codes: (i) $[x, -y, z+{\script{1\over 2}}]$ ; (ii) $[x, -y, z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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 (Farrugia, 2012 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681300024X/hb7022sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681300024X/hb7022Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681300024X/hb7022Isup3.cml

checkCIF report

Comment top

The title compound, (I) (Fig. 1), has been prepared for derivatization and for biological studies. The crystal structure of 4-((4-nitrobenzoyl)amino)benzoic acid (Gorelik et al., 2010) has been published which is related to the title compound.

In (I), the groups A (C1—C8/O1—O4/N1) of methyl 5-amino-2,4-dihydroxybenzoate and B (C9—C15/O5—O7/N2) of 4-nitrobenzoyl are planar with r. m. s. deviation of 0.0252 and 0.0363 Å, respectively. The dihedral angle between A/B is 3.59 (3)°. There exist strong intramolecular H-bondings of N—H···O and O—H···O types (Table 1, Fig. 2) completing S(5) and S(6) ring motifs (Bernstein et al., 1995). There also exist strong intermolecular H-bondings of C—H···O and O—H···O types due to which R₂²(7) and R₂²(10) loops are formed (Table 1, Fig. 2) resulting in the formation of three dimensional polymeric network.

Related literature top

For a related structure, see: Gorelik et al. (2010). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

Equivalent amounts of methyl 5-amino-2,4-dihydroxybenzoate (0.20 g, 1.1 mmol) and 4-nitrobenzoyl chloride (0.20 g, 1.1 mmol) were heated at 333 K for 3 h in dimethylformamide (DMF). The reaction mixture was freeze dried, neutralized with aq. NaHCO₃ (5%) and extracted with dichloromethane (DCM), dried over Na₂SO₄ and evaporated in vacuo to give pure product which was recrystallized from methanol and water solution to afford yellow needles.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The partial packing, which shows that molecules form various ring motifs to form three dimensional polymeric network.

Methyl 2,4-dihydroxy-5-(4-nitrobenzamido)benzoate top

Crystal data top

C₁₅H₁₂N₂O₇	F(000) = 1376
M_r = 332.27	D_x = 1.509 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1519 reflections
a = 30.412 (6) Å	θ = 1.4–26.0°
b = 6.9325 (15) Å	µ = 0.12 mm⁻¹
c = 14.936 (3) Å	T = 296 K
β = 111.737 (8)°	Needle, yellow
V = 2925.0 (11) Å³	0.28 × 0.18 × 0.16 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	2885 independent reflections
Radiation source: fine-focus sealed tube	1519 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
Detector resolution: 8.00 pixels mm^-1	θ_max = 26.0°, θ_min = 1.4°
ω scans	h = −35→37
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −8→5
T_min = 0.970, T_max = 0.980	l = −18→18
10681 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0575P)²] where P = (F_o² + 2F_c²)/3
2885 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₅H₁₂N₂O₇	V = 2925.0 (11) Å³
M_r = 332.27	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 30.412 (6) Å	µ = 0.12 mm⁻¹
b = 6.9325 (15) Å	T = 296 K
c = 14.936 (3) Å	0.28 × 0.18 × 0.16 mm
β = 111.737 (8)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2885 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1519 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.980	R_int = 0.055
10681 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 0.98	Δρ_max = 0.18 e Å⁻³
2885 reflections	Δρ_min = −0.24 e Å⁻³
220 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
O1	0.10274 (6)	0.1155 (3)	0.32019 (12)	0.0472 (7)
O2	0.05741 (6)	0.1342 (3)	0.40795 (13)	0.0569 (8)
O3	0.09767 (6)	0.1238 (3)	0.59618 (13)	0.0556 (8)
O4	0.26255 (6)	0.0020 (3)	0.72631 (12)	0.0551 (8)
O5	0.25654 (6)	−0.0216 (3)	0.39997 (11)	0.0441 (7)
O6	0.49252 (7)	−0.2190 (4)	0.50312 (16)	0.0817 (10)
O7	0.50869 (7)	−0.1537 (4)	0.65151 (16)	0.0963 (12)
N1	0.26968 (7)	−0.0090 (3)	0.55853 (14)	0.0378 (8)
N2	0.48095 (8)	−0.1732 (4)	0.56944 (19)	0.0571 (10)
C1	0.13985 (9)	0.0859 (4)	0.48802 (17)	0.0319 (9)
C2	0.13784 (9)	0.0904 (4)	0.58047 (19)	0.0364 (9)
C3	0.17868 (9)	0.0616 (4)	0.66047 (18)	0.0415 (10)
C4	0.22102 (9)	0.0301 (4)	0.65078 (17)	0.0371 (9)
C5	0.22394 (8)	0.0249 (3)	0.55857 (17)	0.0303 (9)
C6	0.18331 (8)	0.0531 (3)	0.47889 (16)	0.0314 (9)
C7	0.09636 (10)	0.1146 (4)	0.40347 (18)	0.0390 (10)
C8	0.06012 (10)	0.1408 (5)	0.23493 (19)	0.0624 (13)
C9	0.28430 (8)	−0.0313 (3)	0.48462 (17)	0.0298 (9)
C10	0.33614 (8)	−0.0680 (3)	0.51086 (16)	0.0301 (8)
C11	0.36749 (9)	−0.1024 (4)	0.60418 (17)	0.0425 (10)
C12	0.41477 (9)	−0.1343 (4)	0.62442 (19)	0.0448 (10)
C13	0.43065 (9)	−0.1345 (4)	0.54982 (19)	0.0382 (9)
C14	0.40103 (9)	−0.1016 (4)	0.45639 (19)	0.0482 (10)
C15	0.35354 (9)	−0.0687 (4)	0.43751 (18)	0.0425 (10)
H1	0.29169	−0.01664	0.61475	0.0453*
H3	0.17730	0.06358	0.72164	0.0499*
H3A	0.07616	0.14790	0.54484	0.0833*
H4	0.25843	0.01839	0.77701	0.0826*
H6	0.18481	0.05032	0.41783	0.0377*
H8A	0.06788	0.13162	0.17835	0.0937*
H8B	0.04667	0.26521	0.23692	0.0937*
H8C	0.03765	0.04218	0.23315	0.0937*
H11	0.35623	−0.10400	0.65419	0.0511*
H12	0.43554	−0.15519	0.68741	0.0538*
H14	0.41260	−0.10127	0.40680	0.0578*
H15	0.33301	−0.04676	0.37444	0.0509*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0365 (11)	0.0729 (14)	0.0296 (10)	0.0091 (10)	0.0093 (9)	0.0050 (10)
O2	0.0332 (12)	0.0922 (17)	0.0453 (12)	0.0137 (11)	0.0146 (10)	0.0050 (11)
O3	0.0351 (12)	0.0936 (17)	0.0440 (12)	0.0141 (12)	0.0216 (10)	0.0101 (12)
O4	0.0339 (11)	0.1073 (18)	0.0236 (9)	0.0067 (11)	0.0101 (9)	0.0008 (11)
O5	0.0321 (10)	0.0767 (15)	0.0233 (9)	0.0060 (10)	0.0099 (8)	0.0008 (9)
O6	0.0442 (14)	0.144 (2)	0.0601 (15)	0.0172 (14)	0.0232 (12)	−0.0166 (15)
O7	0.0364 (13)	0.189 (3)	0.0497 (14)	0.0125 (16)	−0.0002 (11)	−0.0097 (16)
N1	0.0263 (12)	0.0631 (17)	0.0222 (10)	0.0026 (11)	0.0069 (9)	0.0004 (11)
N2	0.0335 (15)	0.087 (2)	0.0471 (16)	0.0061 (14)	0.0106 (13)	−0.0062 (15)
C1	0.0295 (15)	0.0362 (17)	0.0312 (14)	0.0024 (12)	0.0128 (12)	0.0022 (12)
C2	0.0346 (16)	0.0428 (18)	0.0368 (15)	0.0043 (14)	0.0189 (13)	0.0039 (13)
C3	0.0367 (17)	0.063 (2)	0.0287 (14)	0.0020 (15)	0.0165 (13)	0.0005 (14)
C4	0.0345 (16)	0.0483 (19)	0.0266 (13)	−0.0013 (14)	0.0090 (12)	0.0004 (13)
C5	0.0266 (15)	0.0385 (17)	0.0284 (13)	−0.0013 (12)	0.0131 (11)	−0.0010 (12)
C6	0.0345 (16)	0.0361 (16)	0.0246 (13)	−0.0033 (12)	0.0122 (12)	−0.0014 (12)
C7	0.0383 (18)	0.0457 (18)	0.0350 (15)	0.0051 (14)	0.0159 (13)	0.0029 (13)
C8	0.0466 (19)	0.098 (3)	0.0312 (16)	0.0178 (19)	0.0013 (14)	0.0066 (17)
C9	0.0317 (15)	0.0314 (16)	0.0276 (14)	−0.0019 (12)	0.0125 (12)	−0.0010 (12)
C10	0.0323 (15)	0.0312 (16)	0.0273 (13)	−0.0008 (12)	0.0116 (11)	−0.0039 (12)
C11	0.0372 (17)	0.063 (2)	0.0296 (14)	0.0045 (15)	0.0149 (13)	0.0008 (14)
C12	0.0348 (17)	0.065 (2)	0.0295 (15)	0.0044 (15)	0.0059 (12)	−0.0001 (14)
C13	0.0244 (15)	0.0484 (18)	0.0405 (16)	0.0013 (14)	0.0104 (12)	−0.0033 (14)
C14	0.0394 (18)	0.077 (2)	0.0328 (15)	0.0059 (16)	0.0189 (13)	0.0019 (15)
C15	0.0301 (16)	0.068 (2)	0.0287 (14)	0.0075 (15)	0.0101 (12)	0.0035 (14)

Geometric parameters (Å, º) top

O1—C7	1.328 (3)	C4—C5	1.413 (3)
O1—C8	1.453 (3)	C5—C6	1.376 (3)
O2—C7	1.219 (4)	C9—C10	1.499 (4)
O3—C2	1.347 (4)	C10—C15	1.382 (4)
O4—C4	1.360 (3)	C10—C11	1.387 (3)
O5—C9	1.235 (3)	C11—C12	1.373 (4)
O6—N2	1.210 (4)	C12—C13	1.369 (4)
O7—N2	1.211 (3)	C13—C14	1.371 (4)
O3—H3A	0.8200	C14—C15	1.384 (4)
O4—H4	0.8200	C3—H3	0.9300
N1—C9	1.343 (3)	C6—H6	0.9300
N1—C5	1.411 (3)	C8—H8A	0.9600
N2—C13	1.472 (4)	C8—H8B	0.9600
N1—H1	0.8600	C8—H8C	0.9600
C1—C7	1.465 (4)	C11—H11	0.9300
C1—C6	1.397 (4)	C12—H12	0.9300
C1—C2	1.405 (4)	C14—H14	0.9300
C2—C3	1.382 (4)	C15—H15	0.9300
C3—C4	1.366 (4)

C7—O1—C8	115.4 (2)	C9—C10—C15	117.9 (2)
C2—O3—H3A	109.00	C11—C10—C15	118.3 (2)
C4—O4—H4	109.00	C9—C10—C11	123.8 (2)
C5—N1—C9	130.3 (2)	C10—C11—C12	121.5 (2)
O6—N2—C13	118.7 (2)	C11—C12—C13	118.5 (2)
O6—N2—O7	123.6 (3)	N2—C13—C12	119.5 (2)
O7—N2—C13	117.7 (2)	C12—C13—C14	122.1 (3)
C9—N1—H1	115.00	N2—C13—C14	118.4 (2)
C5—N1—H1	115.00	C13—C14—C15	118.5 (3)
C6—C1—C7	121.5 (2)	C10—C15—C14	121.1 (2)
C2—C1—C7	119.4 (3)	C2—C3—H3	120.00
C2—C1—C6	119.1 (2)	C4—C3—H3	120.00
O3—C2—C3	117.2 (2)	C1—C6—H6	119.00
C1—C2—C3	119.6 (3)	C5—C6—H6	119.00
O3—C2—C1	123.2 (2)	O1—C8—H8A	109.00
C2—C3—C4	120.8 (2)	O1—C8—H8B	109.00
O4—C4—C3	123.9 (2)	O1—C8—H8C	109.00
O4—C4—C5	115.5 (2)	H8A—C8—H8B	109.00
C3—C4—C5	120.6 (2)	H8A—C8—H8C	109.00
N1—C5—C4	115.0 (2)	H8B—C8—H8C	109.00
C4—C5—C6	118.6 (2)	C10—C11—H11	119.00
N1—C5—C6	126.4 (2)	C12—C11—H11	119.00
C1—C6—C5	121.2 (2)	C11—C12—H12	121.00
O1—C7—O2	122.2 (2)	C13—C12—H12	121.00
O1—C7—C1	114.2 (3)	C13—C14—H14	121.00
O2—C7—C1	123.6 (2)	C15—C14—H14	121.00
N1—C9—C10	116.2 (2)	C10—C15—H15	119.00
O5—C9—N1	121.8 (2)	C14—C15—H15	119.00
O5—C9—C10	122.1 (2)

C8—O1—C7—O2	−0.2 (4)	C2—C3—C4—O4	179.6 (3)
C8—O1—C7—C1	179.1 (2)	C2—C3—C4—C5	−0.5 (4)
C9—N1—C5—C4	176.6 (2)	O4—C4—C5—N1	0.1 (3)
C9—N1—C5—C6	−3.7 (4)	O4—C4—C5—C6	−179.7 (2)
C5—N1—C9—O5	0.8 (4)	C3—C4—C5—N1	−179.9 (2)
C5—N1—C9—C10	−179.3 (2)	C3—C4—C5—C6	0.3 (4)
O6—N2—C13—C12	162.4 (3)	N1—C5—C6—C1	−179.9 (2)
O6—N2—C13—C14	−17.0 (4)	C4—C5—C6—C1	−0.1 (3)
O7—N2—C13—C12	−19.0 (4)	O5—C9—C10—C11	−172.1 (2)
O7—N2—C13—C14	161.7 (3)	O5—C9—C10—C15	7.5 (3)
C6—C1—C2—O3	179.0 (2)	N1—C9—C10—C11	8.0 (3)
C6—C1—C2—C3	−0.3 (4)	N1—C9—C10—C15	−172.4 (2)
C7—C1—C2—O3	−1.3 (4)	C9—C10—C11—C12	−179.7 (2)
C7—C1—C2—C3	179.4 (3)	C15—C10—C11—C12	0.8 (4)
C2—C1—C6—C5	0.1 (4)	C9—C10—C15—C14	−180.0 (2)
C7—C1—C6—C5	−179.5 (2)	C11—C10—C15—C14	−0.4 (4)
C2—C1—C7—O1	177.3 (2)	C10—C11—C12—C13	−1.0 (4)
C2—C1—C7—O2	−3.4 (4)	C11—C12—C13—N2	−178.5 (3)
C6—C1—C7—O1	−3.0 (4)	C11—C12—C13—C14	0.8 (4)
C6—C1—C7—O2	176.3 (3)	N2—C13—C14—C15	178.8 (3)
O3—C2—C3—C4	−178.9 (3)	C12—C13—C14—C15	−0.5 (4)
C1—C2—C3—C4	0.4 (4)	C13—C14—C15—C10	0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	2.16	2.595 (3)	111
O3—H3A···O2	0.82	1.91	2.619 (3)	144
O4—H4···O5ⁱ	0.82	1.86	2.670 (2)	170
C8—H8A···O3ⁱⁱ	0.96	2.51	3.274 (4)	137
C12—H12···O7ⁱⁱⁱ	0.93	2.38	3.297 (4)	171
C15—H15···O4ⁱⁱ	0.93	2.46	3.370 (3)	165

Symmetry codes: (i) x, −y, z+1/2; (ii) x, −y, z−1/2; (iii) −x+1, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₂O₇
M_r	332.27
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	30.412 (6), 6.9325 (15), 14.936 (3)
β (°)	111.737 (8)
V (Å³)	2925.0 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.28 × 0.18 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.970, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	10681, 2885, 1519
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.134, 0.98
No. of reflections	2885
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.24

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and PLATON (Spek, 2009), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	2.16	2.595 (3)	111
O3—H3A···O2	0.82	1.91	2.619 (3)	144
O4—H4···O5ⁱ	0.82	1.86	2.670 (2)	170
C8—H8A···O3ⁱⁱ	0.96	2.51	3.274 (4)	137
C12—H12···O7ⁱⁱⁱ	0.93	2.38	3.297 (4)	171
C15—H15···O4ⁱⁱ	0.93	2.46	3.370 (3)	165

Symmetry codes: (i) x, −y, z+1/2; (ii) x, −y, z−1/2; (iii) −x+1, y, −z+3/2.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

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