N-[3-(Benzene­sulfonamido)­prop­yl]benzene­sulfonamide

Sheikh, T.A.; Khan, I.U.; Harrison, W.T.A.; Ejaz

doi:10.1107/S1600536811020150

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1737

doi:10.1107/S1600536811020150

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N-[3-(Benzenesulfonamido)propyl]benzenesulfonamide

Tahir Ali Sheikh,^a Islam Ullah Khan,^a ^* William T. A. Harrison ^b and Ejaz ^a

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, and ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
^*Correspondence e-mail: iuklodhi@yahoo.com

(Received 18 May 2011; accepted 26 May 2011; online 18 June 2011)

In the title compound, C₁₅H₁₈N₂O₄S₂, the dihedral angle between the aromatic rings is 71.8 (2)°. The conformation of the central N—C—C—C—N fragment is gauche–gauche [torsion angles = 72.5 (5) and 65.7 (5)°]. Both N atoms adopt pyramidal geometries. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, generating (001) sheets, and weak C—H⋯O interactions consolidate the packing.

Related literature

For a related structure, see: Linden & Bienz (1999 ).

Experimental

Crystal data

C₁₅H₁₈N₂O₄S₂
M_r = 354.43
Orthorhombic, P b c a
a = 9.2650 (13) Å
b = 16.402 (2) Å
c = 22.740 (3) Å
V = 3455.5 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 296 K
0.40 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
13896 measured reflections
3393 independent reflections
1607 reflections with I > 2σ(I)
R_int = 0.091

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.181
S = 1.03
3393 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4ⁱ	0.82 (4)	2.15 (5)	2.954 (6)	164 (4)
N2—H2⋯O3ⁱⁱ	0.74 (4)	2.15 (4)	2.836 (4)	154 (5)
C9—H9B⋯O4ⁱⁱⁱ	0.97	2.51	3.430 (5)	158
C13—H13⋯O1^iv	0.93	2.42	3.276 (8)	153
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iv) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020150/om2431sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020150/om2431Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020150/om2431Isup3.cml

checkCIF report

Comment top

The title compound, (I), complements N-{4-[(benzenesulfonyl)amino]butyl}benzenesulfonamide, C₁₆H₂₀N₂O₄S₂ (Linden & Bienz, 1999), (II), with a propyl chain in (I) replacing the butyl chain in (II).

In (I) (Fig. 1), the dihedral angle between the aromatic rings is 71.8 (2)°. The conformation of the central N—C—C—C—N chain linking the two S atoms can be described as gauche–gauche in terms of the N1—C7—C8—C9 and C7—C8—C9—N2 torsion angles of 72.5 (5) and 65.7 (5)°, respectively. Both N atoms in (I) are clearly in pyramidal coordination geometries, implying that the lone pairs on the N atoms are not conjugated with their adjacent benzene sulfonyl groups. A similar situation was observed in (II).

In the crystal of (I), the molecules are linked by N—H···O hydrogen bonds (Table 1). Considered separately, the N1 bond leads to [010] C(8) chains and the N2 bond generates [100] C(4) chains. Both the acceptor O atoms are part of the same (atom S2) sulfonyl group: it is perhaps notable that these O atoms have significantly smaller U_eq values that the O atoms in the other (atom S1) sulfonyl group that do not accept a hydrogen bond. Overall, (001) sheets arise from the N—H···O hydrogen bonds in (I) and weak C—H···O links consolidate the packing.

The complete molecule of (II) is generated by inversion symmetry and therefore the conformation of the central alkyl chain is all-trans and the dihedral angle between the aromatic rings is constrained to be zero by symmetry.

Related literature top

For a related structure, see: Linden & Bienz (1999).

Experimental top

A mixture of 1,3-diaminoprpoane (0.0067 mol, 0.561 ml) and benzene sulfonyl chloride (0.0135 mol, 1.72 ml), was stirred in 15 ml of distilled water, while maintaining the pH of the reaction mixture at 9 using 3% sodium carbonate. The progress of the reaction was checked by TLC. On completion, the precipitate obtained was filtered, washed with water and finally dried. Colourless blocks of (I) were grown from methanol by slow evaporation.

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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.

N-[3-(Benzenesulfonamido)propyl]benzenesulfonamide top

Crystal data top

C₁₅H₁₈N₂O₄S₂	F(000) = 1488
M_r = 354.43	D_x = 1.363 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2014 reflections
a = 9.2650 (13) Å	θ = 2.6–21.2°
b = 16.402 (2) Å	µ = 0.33 mm⁻¹
c = 22.740 (3) Å	T = 296 K
V = 3455.5 (8) Å³	Prism, colourless
Z = 8	0.40 × 0.20 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	1607 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.091
Graphite monochromator	θ_max = 26.0°, θ_min = 2.5°
ω scans	h = −5→11
13896 measured reflections	k = −18→20
3393 independent reflections	l = −28→27

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)] = 0.069	Hydrogen site location: difmap (N-H) and geom (C-H)
wR(F²) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0722P)² + 0.3591P] where P = (F_o² + 2F_c²)/3
3393 reflections	(Δ/σ)_max < 0.001
215 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₅H₁₈N₂O₄S₂	V = 3455.5 (8) Å³
M_r = 354.43	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.2650 (13) Å	µ = 0.33 mm⁻¹
b = 16.402 (2) Å	T = 296 K
c = 22.740 (3) Å	0.40 × 0.20 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	1607 reflections with I > 2σ(I)
13896 measured reflections	R_int = 0.091
3393 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.23 e Å⁻³
3393 reflections	Δρ_min = −0.35 e Å⁻³
215 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.1983 (7)	0.4365 (4)	0.3462 (2)	0.0749 (16)
C2	0.0703 (9)	0.4669 (4)	0.3255 (3)	0.102 (2)
H2A	0.0580	0.5230	0.3219	0.123*
C3	−0.0417 (9)	0.4144 (6)	0.3098 (3)	0.124 (3)
H3A	−0.1276	0.4354	0.2950	0.148*
C4	−0.0255 (10)	0.3346 (5)	0.3158 (3)	0.118 (3)
H4A	−0.1004	0.2997	0.3053	0.141*
C5	0.0988 (12)	0.3034 (4)	0.3372 (3)	0.118 (3)
H5	0.1090	0.2473	0.3414	0.142*
C6	0.2110 (8)	0.3546 (4)	0.3528 (3)	0.102 (2)
H6	0.2958	0.3327	0.3679	0.123*
C7	0.1906 (5)	0.5379 (3)	0.4664 (2)	0.0624 (13)
H7A	0.1191	0.4948	0.4645	0.075*
H7B	0.1539	0.5845	0.4447	0.075*
C8	0.2153 (5)	0.5616 (3)	0.5296 (2)	0.0603 (13)
H8A	0.1224	0.5666	0.5489	0.072*
H8B	0.2677	0.5179	0.5489	0.072*
C9	0.2973 (4)	0.6398 (2)	0.5381 (2)	0.0556 (12)
H9A	0.3180	0.6476	0.5795	0.067*
H9B	0.3883	0.6371	0.5171	0.067*
C10	0.3019 (4)	0.8225 (2)	0.5942 (2)	0.0490 (11)
C11	0.4299 (5)	0.7968 (3)	0.6201 (2)	0.0680 (14)
H11	0.5002	0.7705	0.5980	0.082*
C12	0.4507 (8)	0.8108 (4)	0.6785 (3)	0.096 (2)
H12	0.5355	0.7930	0.6963	0.116*
C13	0.3495 (10)	0.8504 (5)	0.7115 (3)	0.106 (2)
H13	0.3650	0.8589	0.7514	0.128*
C14	0.2258 (8)	0.8775 (3)	0.6857 (3)	0.095 (2)
H14	0.1585	0.9061	0.7079	0.114*
C15	0.1992 (6)	0.8627 (3)	0.6261 (3)	0.0738 (15)
H15	0.1136	0.8798	0.6087	0.089*
S1	0.33690 (18)	0.50195 (11)	0.36927 (6)	0.0851 (5)
S2	0.27067 (10)	0.79981 (7)	0.52013 (5)	0.0495 (4)
N1	0.3261 (4)	0.5097 (3)	0.43942 (19)	0.0622 (12)
H1	0.349 (5)	0.466 (3)	0.455 (2)	0.064 (17)*
N2	0.2115 (3)	0.7085 (2)	0.51605 (18)	0.0547 (10)
H2	0.135 (5)	0.708 (3)	0.525 (2)	0.066*
O1	0.3051 (5)	0.5811 (3)	0.34561 (18)	0.1226 (17)
O2	0.4721 (5)	0.4642 (3)	0.35702 (17)	0.1228 (17)
O3	0.4064 (3)	0.8029 (2)	0.49056 (13)	0.0654 (9)
O4	0.1556 (3)	0.85005 (18)	0.49911 (14)	0.0637 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.106 (5)	0.064 (4)	0.054 (3)	−0.007 (3)	0.002 (3)	0.011 (3)
C2	0.140 (6)	0.064 (4)	0.104 (5)	−0.017 (4)	−0.029 (5)	0.018 (3)
C3	0.137 (7)	0.110 (7)	0.125 (6)	−0.012 (5)	−0.049 (5)	−0.002 (5)
C4	0.170 (8)	0.086 (6)	0.097 (5)	−0.031 (6)	−0.025 (5)	−0.008 (4)
C5	0.202 (9)	0.059 (5)	0.093 (5)	−0.010 (6)	−0.022 (6)	−0.010 (4)
C6	0.144 (6)	0.072 (5)	0.090 (4)	0.001 (5)	−0.016 (4)	−0.009 (4)
C7	0.051 (3)	0.048 (3)	0.088 (4)	−0.005 (2)	−0.003 (3)	−0.006 (3)
C8	0.053 (3)	0.045 (3)	0.083 (4)	−0.003 (2)	0.002 (3)	0.005 (2)
C9	0.044 (2)	0.046 (3)	0.077 (3)	0.005 (2)	−0.013 (2)	0.000 (2)
C10	0.045 (3)	0.033 (2)	0.068 (3)	0.0005 (19)	0.009 (2)	0.000 (2)
C11	0.055 (3)	0.067 (4)	0.082 (4)	0.005 (3)	−0.008 (3)	−0.011 (3)
C12	0.103 (5)	0.098 (5)	0.088 (5)	−0.012 (4)	−0.021 (4)	−0.020 (4)
C13	0.144 (7)	0.089 (5)	0.086 (5)	−0.015 (5)	−0.001 (5)	−0.005 (4)
C14	0.122 (6)	0.063 (4)	0.099 (5)	−0.010 (4)	0.045 (5)	−0.017 (4)
C15	0.069 (4)	0.055 (4)	0.098 (4)	0.001 (3)	0.017 (3)	0.006 (3)
S1	0.0949 (12)	0.0843 (12)	0.0762 (10)	−0.0253 (10)	0.0100 (8)	0.0154 (9)
S2	0.0281 (5)	0.0490 (7)	0.0714 (8)	0.0022 (5)	0.0015 (5)	0.0115 (6)
N1	0.062 (3)	0.049 (3)	0.075 (3)	−0.004 (2)	−0.002 (2)	0.005 (2)
N2	0.0289 (17)	0.048 (2)	0.087 (3)	0.0049 (18)	−0.001 (2)	0.007 (2)
O1	0.176 (5)	0.095 (3)	0.098 (3)	−0.049 (3)	−0.024 (3)	0.050 (3)
O2	0.091 (3)	0.169 (5)	0.108 (3)	−0.015 (3)	0.045 (3)	−0.021 (3)
O3	0.0318 (15)	0.090 (2)	0.075 (2)	−0.0012 (16)	0.0080 (15)	0.0128 (18)
O4	0.0395 (16)	0.057 (2)	0.095 (2)	0.0091 (15)	−0.0078 (16)	0.0255 (17)

Geometric parameters (Å, º) top

C1—C6	1.357 (7)	C9—H9B	0.9700
C1—C2	1.370 (8)	C10—C15	1.368 (6)
C1—S1	1.754 (6)	C10—C11	1.390 (6)
C2—C3	1.395 (9)	C10—S2	1.748 (5)
C2—H2A	0.9300	C11—C12	1.362 (7)
C3—C4	1.325 (9)	C11—H11	0.9300
C3—H3A	0.9300	C12—C13	1.365 (9)
C4—C5	1.351 (9)	C12—H12	0.9300
C4—H4A	0.9300	C13—C14	1.362 (9)
C5—C6	1.382 (9)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.398 (7)
C6—H6	0.9300	C14—H14	0.9300
C7—N1	1.471 (6)	C15—H15	0.9300
C7—C8	1.506 (6)	S1—O2	1.424 (4)
C7—H7A	0.9700	S1—O1	1.435 (4)
C7—H7B	0.9700	S1—N1	1.603 (4)
C8—C9	1.503 (6)	S2—O3	1.427 (3)
C8—H8A	0.9700	S2—O4	1.430 (3)
C8—H8B	0.9700	S2—N2	1.597 (4)
C9—N2	1.468 (5)	N1—H1	0.82 (4)
C9—H9A	0.9700	N2—H2	0.74 (4)

C6—C1—C2	118.3 (6)	C15—C10—C11	120.9 (5)
C6—C1—S1	120.7 (5)	C15—C10—S2	120.0 (4)
C2—C1—S1	120.9 (5)	C11—C10—S2	119.1 (4)
C1—C2—C3	120.4 (6)	C12—C11—C10	118.9 (5)
C1—C2—H2A	119.8	C12—C11—H11	120.5
C3—C2—H2A	119.8	C10—C11—H11	120.5
C4—C3—C2	120.0 (8)	C11—C12—C13	121.2 (6)
C4—C3—H3A	120.0	C11—C12—H12	119.4
C2—C3—H3A	120.0	C13—C12—H12	119.4
C3—C4—C5	120.5 (8)	C14—C13—C12	119.8 (6)
C3—C4—H4A	119.7	C14—C13—H13	120.1
C5—C4—H4A	119.7	C12—C13—H13	120.1
C4—C5—C6	120.3 (7)	C13—C14—C15	120.6 (6)
C4—C5—H5	119.9	C13—C14—H14	119.7
C6—C5—H5	119.9	C15—C14—H14	119.7
C1—C6—C5	120.5 (7)	C10—C15—C14	118.4 (5)
C1—C6—H6	119.7	C10—C15—H15	120.8
C5—C6—H6	119.7	C14—C15—H15	120.8
N1—C7—C8	110.4 (4)	O2—S1—O1	120.0 (3)
N1—C7—H7A	109.6	O2—S1—N1	106.5 (3)
C8—C7—H7A	109.6	O1—S1—N1	106.8 (3)
N1—C7—H7B	109.6	O2—S1—C1	108.6 (3)
C8—C7—H7B	109.6	O1—S1—C1	106.9 (3)
H7A—C7—H7B	108.1	N1—S1—C1	107.4 (2)
C9—C8—C7	114.8 (4)	O3—S2—O4	118.66 (18)
C9—C8—H8A	108.6	O3—S2—N2	107.9 (2)
C7—C8—H8A	108.6	O4—S2—N2	105.36 (18)
C9—C8—H8B	108.6	O3—S2—C10	107.48 (19)
C7—C8—H8B	108.6	O4—S2—C10	108.8 (2)
H8A—C8—H8B	107.6	N2—S2—C10	108.2 (2)
N2—C9—C8	109.8 (3)	C7—N1—S1	119.5 (4)
N2—C9—H9A	109.7	C7—N1—H1	108 (3)
C8—C9—H9A	109.7	S1—N1—H1	110 (3)
N2—C9—H9B	109.7	C9—N2—S2	121.0 (3)
C8—C9—H9B	109.7	C9—N2—H2	115 (4)
H9A—C9—H9B	108.2	S2—N2—H2	109 (4)

C6—C1—C2—C3	−2.1 (9)	C2—C1—S1—O2	−147.7 (5)
S1—C1—C2—C3	−177.1 (5)	C6—C1—S1—O1	168.2 (5)
C1—C2—C3—C4	1.2 (11)	C2—C1—S1—O1	−16.9 (6)
C2—C3—C4—C5	0.0 (12)	C6—C1—S1—N1	−77.5 (5)
C3—C4—C5—C6	−0.2 (12)	C2—C1—S1—N1	97.4 (5)
C2—C1—C6—C5	1.9 (9)	C15—C10—S2—O3	147.5 (4)
S1—C1—C6—C5	176.9 (5)	C11—C10—S2—O3	−34.5 (4)
C4—C5—C6—C1	−0.8 (10)	C15—C10—S2—O4	17.8 (4)
N1—C7—C8—C9	72.5 (5)	C11—C10—S2—O4	−164.2 (3)
C7—C8—C9—N2	65.7 (5)	C15—C10—S2—N2	−96.2 (4)
C15—C10—C11—C12	1.4 (7)	C11—C10—S2—N2	81.8 (4)
S2—C10—C11—C12	−176.6 (4)	C8—C7—N1—S1	−165.2 (3)
C10—C11—C12—C13	−1.0 (9)	O2—S1—N1—C7	−173.0 (4)
C11—C12—C13—C14	−0.8 (10)	O1—S1—N1—C7	57.7 (4)
C12—C13—C14—C15	2.2 (10)	C1—S1—N1—C7	−56.7 (4)
C11—C10—C15—C14	0.0 (7)	C8—C9—N2—S2	179.2 (3)
S2—C10—C15—C14	178.0 (4)	O3—S2—N2—C9	56.7 (4)
C13—C14—C15—C10	−1.8 (8)	O4—S2—N2—C9	−175.6 (3)
C6—C1—S1—O2	37.4 (5)	C10—S2—N2—C9	−59.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.82 (4)	2.15 (5)	2.954 (6)	164 (4)
N2—H2···O3ⁱⁱ	0.74 (4)	2.15 (4)	2.836 (4)	154 (5)
C9—H9B···O4ⁱⁱⁱ	0.97	2.51	3.430 (5)	158
C13—H13···O1^iv	0.93	2.42	3.276 (8)	153

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₈N₂O₄S₂
M_r	354.43
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	9.2650 (13), 16.402 (2), 22.740 (3)
V (Å³)	3455.5 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13896, 3393, 1607
R_int	0.091
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.181, 1.03
No. of reflections	3393
No. of parameters	215
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.35

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.82 (4)	2.15 (5)	2.954 (6)	164 (4)
N2—H2···O3ⁱⁱ	0.74 (4)	2.15 (4)	2.836 (4)	154 (5)
C9—H9B···O4ⁱⁱⁱ	0.97	2.51	3.430 (5)	158
C13—H13···O1^iv	0.93	2.42	3.276 (8)	153

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

Acknowledgements

IUK thanks the Higher Education Commission of Pakistan for financial support under the project to strengthen the Materials Chemistry Laboratory at GCUL.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Linden, A. & Bienz, S. (1999). Acta Cryst. C55 IUC9900046. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar