N-(2-Chloro-4-nitro­phen­yl)-2-nitro­benzamide

Saeed, A.; Hussain, S.; Flörke, U.

doi:10.1107/S1600536808006430

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o705

doi:10.1107/S1600536808006430

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ADDENDA AND ERRATA

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N-(2-Chloro-4-nitrophenyl)-2-nitrobenzamide

Aamer Saeed,^a ^* Shahid Hussain ^a and Ulrich Flörke ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and ^bDepartment Chemie, Fakultät für Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 17 January 2008; accepted 7 March 2008; online 12 March 2008)

In the title compound, C₁₃H₈ClN₃O₅, the dihedral angle between the two aromatic rings is 70.74 (6)°. The nitro groups of the Cl-substituted and benzamide benzene rings are twisted by 2.6 (1) and 31.3 (2)°, respectively. The crystal packing shows intermolecular C—H⋯O hydrogen bonds that link molecules into sheets stacked along [010].

Related literature

For the biological activities of benzanilides and related compounds, see: Makino et al. (2003 ); Ho et al. (2002 ); Zhichkin et al. (2007 ); Jackson et al. (1994 ); Capdeville et al. (2002 ); Igawa et al. (1999 ). For related structures, see: Di Rienzo et al. (1980 ); Batsanov & Lyubchik (2003 ).

Experimental

Crystal data

C₁₃H₈ClN₃O₅
M_r = 321.67
Orthorhombic, P b c a
a = 7.8053 (9) Å
b = 13.8621 (17) Å
c = 24.101 (3) Å
V = 2607.7 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 120 (2) K
0.47 × 0.20 × 0.14 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.863, T_max = 0.956
21562 measured reflections
3111 independent reflections
2424 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.107
S = 1.04
3111 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1	0.95	2.24	2.848 (2)	121
C10—H10A⋯O4ⁱ	0.95	2.35	3.246 (2)	157
C11—H11A⋯O2ⁱⁱ	0.95	2.55	3.202 (2)	126
Symmetry codes: (i) x+1, y, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006430/si2073sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808006430/si2073Isup2.hkl

checkCIF report

Comment top

The benzanilide core is present in compounds with such a wide range of biological activities that it has been called a privileged structure. Benzanilides serve as intermediates towards benzothiadiazin-4-ones (Makino et al., 2003), benzodiazepine-2,5-diones (Ho et al., 2002), and 2,3-disubstituted 3H-quinazoline-4-ones (Zhichkin et al., 2007). Benzanilides have established their efficacy as centroid elements of ligands that bind to a wide variety of receptor types. Thus benzanilides containing aminoalkyl groups originally designed as a peptidomimetic, have been incorporated in an Arg-Gly-Asp cyclic peptide yielding a high affinity GPIIb/IIIa ligand (Jackson et al., 1994). Imatinib is an ATP-site binding kinase inhibitor and platelet-derived growth factor receptor kinases (Capdeville et al., 2002).Benzamides have activities as acetyl-CoA carboxylase and farnesyl transferase inhibitors (Igawa et al., 1999) The literature is full of the function of the 2-chloro-4-nitrophenyl group (CNP) and also structures of nitrobenzamide (NB) and related compounds (Di Rienzo et al., 1980; Batsanov & Lyubchik, 2003). The aim of the present work was to combine CNP and NB in a single structure which is not well known in the literature.

Geometric parameters of the title compound, C₁₃H₈ClN₃O₅, are in the usual ranges. The dihedral angle between the two aromatic rings is 70.74 (6)°. The N2 nitro group is twisted by 31.3 (2)° from the plane of the C2–C7 phenyl ring, and the N3 group 2.6 (2)° from the C8–C13 plane, respectively. The crystal packing shows intermolecular C–H···O hydrogen bonds, from the Cl-phenyl group to both nitro groups. Details are depicted in Table 1. By these hydrogen bonds molecules are linked to endless sheets that are stacked along [010]. Additionally, stacking of molecules along [100] can be recognized. The intramolecular C13–H13A···O1 interaction is a common feature for this molecule with an almost planar O1–C1–N1–C8–C13 arrangement. The corresponding torsion angles are C8–N1–C1–O1 6.7 (3)° and C1–N1–C8–C13 - 7.6 (3)°, respectively.

Related literature top

For the biological activities of benzanilides and related compounds, see: Makino et al. (2003); Ho et al. (2002); Zhichkin et al. (2007); Jackson et al. (1994); Capdeville et al. (2002); Igawa et al. (1999). For related structures, see: Di Rienzo et al. (1980); Batsanov & Lyubchik (2003).

Experimental top

2-Nitrobenzoyl chloride (5.4 mmol) in CHCl₃ was treated with 2-chloro-4-nitroaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 3 h. Upon cooling, the reaction mixture was diluted with CHCl₃ and washed consecutively with aq 1 M HCl and saturated aq NaHCO₃. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue in CHCl₃ afforded the title compound (84%) as white needles: IR (KBr) 3226, 1665, 1616, 1520, 1352 cm-1; 1H NMR (CDCl3, 400 MHz) ? 8.13 (d, J) 8 Hz, 1H), 7.81 (d, J) 8 Hz, 1H), 7.51 (dd, J) 8 Hz, 1H), 7.66 (dd, J) 8 Hz, 1H), 7.43 (d, J) 8 Hz, 2H), 7.36 (br s, 1H), 7.25 (d, J) 8 Hz, 1H); 13 C NMR (100 MHz) ? 164.7, 147.8, 134.6, 134.4, 132.7, 132.1, 130.3, 129.9, 129.3, 125.0. Anal. Calcd. For C₁₃H₉N₃O₅, C, 48.54; H, 2.51; Cl, 11.02; N, 13.06 found C, 48.12; H, 2.31; Cl, 11.3; N, 12.94.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing viewed along [100] with intermolecular hydrogen bonding pattern indicated as dashed lines. H-atoms not involved in hydrogen bonding are omitted.

N-(2-Chloro-4-nitrophenyl)-2-nitrobenzamide top

Crystal data top

C₁₃H₈ClN₃O₅	F(000) = 1312
M_r = 321.67	D_x = 1.639 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 769 reflections
a = 7.8053 (9) Å	θ = 2.9–25.7°
b = 13.8621 (17) Å	µ = 0.32 mm⁻¹
c = 24.101 (3) Å	T = 120 K
V = 2607.7 (5) Å³	Prism, colourless
Z = 8	0.47 × 0.20 × 0.14 mm

Data collection top

Bruker SMART APEX diffractometer	3111 independent reflections
Radiation source: sealed tube	2424 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ϕ and ω scans	θ_max = 27.9°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
T_min = 0.863, T_max = 0.956	k = −18→16
21562 measured reflections	l = −31→31

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: difference Fourier map
wR(F²) = 0.107	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0553P)² + 0.7975P] where P = (F_o² + 2F_c²)/3
3111 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₃H₈ClN₃O₅	V = 2607.7 (5) Å³
M_r = 321.67	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.8053 (9) Å	µ = 0.32 mm⁻¹
b = 13.8621 (17) Å	T = 120 K
c = 24.101 (3) Å	0.47 × 0.20 × 0.14 mm

Data collection top

Bruker SMART APEX diffractometer	3111 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2424 reflections with I > 2σ(I)
T_min = 0.863, T_max = 0.956	R_int = 0.053
21562 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.04	Δρ_max = 0.39 e Å⁻³
3111 reflections	Δρ_min = −0.23 e Å⁻³
199 parameters

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
Cl1	1.13944 (6)	0.38512 (3)	0.446787 (18)	0.02271 (13)
O1	0.49413 (17)	0.41462 (11)	0.39481 (5)	0.0317 (3)
O2	0.6129 (2)	0.24007 (10)	0.33719 (6)	0.0374 (4)
O3	0.4575 (2)	0.23191 (11)	0.26277 (7)	0.0428 (4)
O4	0.38629 (18)	0.37084 (12)	0.57016 (6)	0.0388 (4)
O5	0.54709 (19)	0.33143 (11)	0.63925 (5)	0.0345 (4)
N1	0.7841 (2)	0.41233 (11)	0.40825 (6)	0.0221 (3)
H1A	0.8816	0.4222	0.3908	0.027*
N2	0.5594 (2)	0.27328 (11)	0.29309 (7)	0.0269 (4)
N3	0.5267 (2)	0.35472 (11)	0.59071 (6)	0.0229 (3)
C1	0.6395 (2)	0.41795 (13)	0.37682 (7)	0.0208 (4)
C2	0.6749 (2)	0.43395 (13)	0.31581 (7)	0.0191 (4)
C3	0.7458 (2)	0.52025 (13)	0.29780 (7)	0.0226 (4)
H3A	0.7797	0.5675	0.3242	0.027*
C4	0.7676 (3)	0.53806 (14)	0.24147 (7)	0.0253 (4)
H4A	0.8179	0.5969	0.2296	0.030*
C5	0.7163 (3)	0.47032 (14)	0.20255 (7)	0.0254 (4)
H5A	0.7310	0.4831	0.1641	0.030*
C6	0.6437 (2)	0.38416 (14)	0.21950 (7)	0.0237 (4)
H6A	0.6073	0.3376	0.1931	0.028*
C7	0.6253 (2)	0.36732 (13)	0.27579 (7)	0.0200 (4)
C8	0.7961 (2)	0.39263 (12)	0.46521 (7)	0.0190 (4)
C9	0.9581 (2)	0.37737 (12)	0.48863 (7)	0.0196 (4)
C10	0.9792 (2)	0.35510 (13)	0.54414 (7)	0.0216 (4)
H10A	1.0907	0.3443	0.5587	0.026*
C11	0.8378 (2)	0.34852 (13)	0.57846 (7)	0.0211 (4)
H11A	0.8497	0.3338	0.6168	0.025*
C12	0.6785 (2)	0.36410 (12)	0.55510 (7)	0.0192 (4)
C13	0.6534 (2)	0.38633 (12)	0.49987 (7)	0.0194 (4)
H13A	0.5414	0.3971	0.4858	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0156 (2)	0.0279 (2)	0.0246 (2)	0.00115 (17)	0.00315 (15)	0.00015 (17)
O1	0.0189 (7)	0.0559 (10)	0.0203 (6)	0.0026 (7)	0.0019 (5)	0.0048 (6)
O2	0.0461 (10)	0.0290 (8)	0.0371 (8)	−0.0004 (7)	0.0064 (7)	0.0124 (6)
O3	0.0422 (10)	0.0316 (8)	0.0545 (10)	−0.0107 (7)	−0.0013 (8)	−0.0119 (7)
O4	0.0163 (7)	0.0739 (12)	0.0262 (7)	−0.0008 (7)	−0.0005 (6)	0.0062 (7)
O5	0.0305 (8)	0.0551 (10)	0.0178 (6)	0.0020 (7)	0.0025 (5)	0.0071 (6)
N1	0.0153 (8)	0.0339 (9)	0.0172 (7)	0.0003 (7)	0.0018 (6)	0.0034 (6)
N2	0.0255 (9)	0.0226 (8)	0.0325 (9)	0.0008 (7)	0.0081 (7)	−0.0029 (7)
N3	0.0203 (8)	0.0300 (9)	0.0182 (7)	−0.0007 (7)	0.0008 (6)	−0.0010 (6)
C1	0.0205 (9)	0.0234 (9)	0.0186 (8)	0.0022 (7)	0.0016 (7)	0.0004 (7)
C2	0.0138 (9)	0.0243 (9)	0.0191 (8)	0.0035 (7)	0.0011 (6)	0.0020 (7)
C3	0.0195 (10)	0.0239 (9)	0.0245 (9)	0.0002 (8)	0.0013 (7)	−0.0004 (7)
C4	0.0238 (10)	0.0243 (9)	0.0278 (9)	0.0030 (8)	0.0062 (8)	0.0069 (8)
C5	0.0252 (10)	0.0331 (11)	0.0178 (8)	0.0079 (8)	0.0043 (7)	0.0052 (8)
C6	0.0237 (10)	0.0276 (10)	0.0197 (8)	0.0048 (8)	−0.0005 (7)	−0.0048 (7)
C7	0.0162 (9)	0.0212 (9)	0.0226 (9)	0.0026 (7)	0.0028 (7)	0.0002 (7)
C8	0.0182 (9)	0.0197 (9)	0.0191 (8)	0.0001 (7)	−0.0012 (7)	0.0003 (7)
C9	0.0162 (9)	0.0172 (9)	0.0254 (9)	0.0003 (7)	0.0029 (7)	−0.0016 (7)
C10	0.0164 (9)	0.0249 (10)	0.0236 (9)	0.0019 (7)	−0.0038 (7)	0.0003 (7)
C11	0.0217 (9)	0.0230 (9)	0.0187 (8)	0.0008 (8)	−0.0030 (7)	0.0015 (7)
C12	0.0196 (9)	0.0186 (8)	0.0192 (8)	−0.0008 (7)	0.0018 (7)	−0.0015 (7)
C13	0.0153 (9)	0.0238 (9)	0.0191 (8)	−0.0009 (7)	−0.0012 (6)	−0.0010 (7)

Geometric parameters (Å, º) top

Cl1—C9	1.7411 (18)	C4—C5	1.386 (3)
O1—C1	1.216 (2)	C4—H4A	0.9500
O2—N2	1.231 (2)	C5—C6	1.383 (3)
O3—N2	1.223 (2)	C5—H5A	0.9500
O4—N3	1.223 (2)	C6—C7	1.384 (2)
O5—N3	1.2240 (19)	C6—H6A	0.9500
N1—C1	1.362 (2)	C8—C13	1.395 (2)
N1—C8	1.403 (2)	C8—C9	1.401 (2)
N1—H1A	0.8800	C9—C10	1.383 (2)
N2—C7	1.462 (2)	C10—C11	1.383 (3)
N3—C12	1.469 (2)	C10—H10A	0.9500
C1—C2	1.512 (2)	C11—C12	1.381 (3)
C2—C3	1.388 (3)	C11—H11A	0.9500
C2—C7	1.391 (3)	C12—C13	1.380 (2)
C3—C4	1.390 (2)	C13—H13A	0.9500
C3—H3A	0.9500

C1—N1—C8	127.64 (15)	C5—C6—C7	118.53 (17)
C1—N1—H1A	116.2	C5—C6—H6A	120.7
C8—N1—H1A	116.2	C7—C6—H6A	120.7
O3—N2—O2	124.13 (17)	C6—C7—C2	122.60 (17)
O3—N2—C7	118.45 (16)	C6—C7—N2	117.81 (16)
O2—N2—C7	117.41 (16)	C2—C7—N2	119.51 (16)
O4—N3—O5	123.50 (16)	C13—C8—C9	118.04 (16)
O4—N3—C12	118.03 (14)	C13—C8—N1	123.03 (16)
O5—N3—C12	118.46 (15)	C9—C8—N1	118.92 (16)
O1—C1—N1	124.98 (16)	C10—C9—C8	122.07 (16)
O1—C1—C2	121.51 (16)	C10—C9—Cl1	118.51 (14)
N1—C1—C2	113.45 (15)	C8—C9—Cl1	119.41 (13)
C3—C2—C7	117.83 (16)	C11—C10—C9	119.91 (17)
C3—C2—C1	120.22 (16)	C11—C10—H10A	120.0
C7—C2—C1	121.73 (16)	C9—C10—H10A	120.0
C2—C3—C4	120.48 (17)	C12—C11—C10	117.65 (16)
C2—C3—H3A	119.8	C12—C11—H11A	121.2
C4—C3—H3A	119.8	C10—C11—H11A	121.2
C5—C4—C3	120.34 (17)	C13—C12—C11	123.77 (17)
C5—C4—H4A	119.8	C13—C12—N3	117.93 (16)
C3—C4—H4A	119.8	C11—C12—N3	118.28 (15)
C6—C5—C4	120.21 (16)	C12—C13—C8	118.55 (17)
C6—C5—H5A	119.9	C12—C13—H13A	120.7
C4—C5—H5A	119.9	C8—C13—H13A	120.7

C8—N1—C1—O1	6.7 (3)	O2—N2—C7—C2	−29.6 (2)
C8—N1—C1—C2	−176.12 (17)	C1—N1—C8—C13	−7.6 (3)
O1—C1—C2—C3	110.1 (2)	C1—N1—C8—C9	171.65 (18)
N1—C1—C2—C3	−67.2 (2)	C13—C8—C9—C10	1.0 (3)
O1—C1—C2—C7	−64.4 (3)	N1—C8—C9—C10	−178.25 (16)
N1—C1—C2—C7	118.28 (19)	C13—C8—C9—Cl1	−179.73 (13)
C7—C2—C3—C4	−0.8 (3)	N1—C8—C9—Cl1	1.0 (2)
C1—C2—C3—C4	−175.50 (17)	C8—C9—C10—C11	−0.8 (3)
C2—C3—C4—C5	1.0 (3)	Cl1—C9—C10—C11	179.93 (14)
C3—C4—C5—C6	−0.3 (3)	C9—C10—C11—C12	0.5 (3)
C4—C5—C6—C7	−0.5 (3)	C10—C11—C12—C13	−0.4 (3)
C5—C6—C7—C2	0.8 (3)	C10—C11—C12—N3	178.34 (16)
C5—C6—C7—N2	−175.84 (17)	O4—N3—C12—C13	−2.9 (2)
C3—C2—C7—C6	−0.1 (3)	O5—N3—C12—C13	177.27 (17)
C1—C2—C7—C6	174.54 (17)	O4—N3—C12—C11	178.28 (18)
C3—C2—C7—N2	176.43 (16)	O5—N3—C12—C11	−1.6 (3)
C1—C2—C7—N2	−8.9 (3)	C11—C12—C13—C8	0.7 (3)
O3—N2—C7—C6	−31.8 (2)	N3—C12—C13—C8	−178.11 (15)
O2—N2—C7—C6	147.07 (18)	C9—C8—C13—C12	−0.9 (2)
O3—N2—C7—C2	151.52 (17)	N1—C8—C13—C12	178.32 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1	0.95	2.24	2.848 (2)	121
C10—H10A···O4ⁱ	0.95	2.35	3.246 (2)	157
C11—H11A···O2ⁱⁱ	0.95	2.55	3.202 (2)	126

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

Experimental details

Crystal data
Chemical formula	C₁₃H₈ClN₃O₅
M_r	321.67
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	120
a, b, c (Å)	7.8053 (9), 13.8621 (17), 24.101 (3)
V (Å³)	2607.7 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.47 × 0.20 × 0.14

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.863, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	21562, 3111, 2424
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.107, 1.04
No. of reflections	3111
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.23

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1	0.95	2.24	2.848 (2)	121.3
C10—H10A···O4ⁱ	0.95	2.35	3.246 (2)	156.6
C11—H11A···O2ⁱⁱ	0.95	2.55	3.202 (2)	126.0

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

Acknowledgements

AS gratefully acknowledges a research grant from Quaid-i-Azam University, Islamabad.

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