3-(3-Bromo­benz­yl)-1H-isochromen-1-one

Ali, F.I.; Babar, T.M.; Rama, N.H.; Jones, P.G.

doi:10.1107/S1600536809037246

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2511

doi:10.1107/S1600536809037246

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3-(3-Bromobenzyl)-1H-isochromen-1-one

Farukh Iftakhar Ali,^a Tariq Mahmood Babar,^a Nasim Hasan Rama ^a ^* and Peter G. Jones ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Postfach 3329, 38023 Braunschweig, Germany
^*Correspondence e-mail: nhrama@qau.edu.pk

(Received 4 September 2009; accepted 14 September 2009; online 26 September 2009)

In the title compound, C₁₆H₁₁BrO₂, the isocoumarin ring system is planar (r.m.s. deviation = 0.015 Å) and subtends a dihedral angle of 88.90 (2)° with the bromobenzene ring. In the crystal, molecules are linked, forming a three-dimensional packing pattern involving C—H⋯O interactions, Br⋯O contacts [3.4734 (10) Å] and π–π stacking interactions with centroid–centroid distances ranging from 3.667 (2) to 3.765 (2) Å.

Related literature

For the properties and applications of isocoumarins and 3,4-dihydroisocoumarins, see: Chinworrungsee et al. (2002 ); Devienne et al. (2002 ); Mali & Babu (1998 ); Rama et al. (1998 ); Waters & Kozlowski (2001 ). For related structures, see: Abid et al. (2008 ); Babar et al. (2008 ).

Experimental

Crystal data

C₁₆H₁₁BrO₂
M_r = 315.16
Triclinic, $[P \overline 1]$
a = 7.4508 (5) Å
b = 8.1824 (6) Å
c = 11.3663 (8) Å
α = 90.130 (6)°
β = 98.392 (7)°
γ = 113.844 (8)°
V = 625.58 (8) Å³
Z = 2
Mo Kα radiation
μ = 3.28 mm⁻¹
T = 103 K
0.25 × 0.25 × 0.20 mm

Data collection

Oxford Xcalibur E diffractometer
Absorption correction: multi-scan (CrysAlisPro; Oxford Diffraction 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.922, T_max = 1.000
16250 measured reflections
3449 independent reflections
2899 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.045
S = 0.97
3449 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.95	2.58	3.4666 (16)	155
C10—H10A⋯O2ⁱⁱ	0.99	2.50	3.4685 (17)	166
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z+1.

Data collection: CrysAlisPro (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037246/rz2357sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037246/rz2357Isup2.hkl

checkCIF report

Comment top

In recent years, there has been increasing interest in the synthesis of natural products, since they are an excellent and reliable source for the development of new drugs. Isocoumarins and 3,4-dihydroisocoumarins are a class of natural products that often occur as microbial metabolites and that have been found to exhibit interesting biological properties (Mali & Babu, 1998), including anti-fungal, anti-inflammatory, anti-allergic, antiangiogenic, anti-malaria (Chinworrungsee et al., 2002), anti-bacterial (Rama et al., 1998), anti-cancer, anti-virus (Waters & Kozlowski, 2001) and anti-microbial activities (Davienne et al., 2002). In view of the importance of this class of compounds, the title compound, an isocoumarine derivative containing a 3-bromobenzyl substituent, has been synthesized and its crystal structure is reported here. We have previously reported the structures of the analogous fluorine and chlorine derivatives (Babar et al., 2008; Abid et al., 2008), which crystallize with two and three molecules respectively in the asymmetric unit.

The molecule of the title compound is shown in Fig. 1. The structure is not isotypic to either of the analogous derivatives. Bond lengths and angles may be regarded as normal by comparison with the earlier structures (Babar et al., 2008; Abid et al., 2008), although in each structure several bond angles are appreciably different from ideal values [e. g. in the current structure O2—C1—C9 126.19 (12), C3—C2—C10 128.78 (12), O1—C2—C10 109.56 (11), C2—C10—C11 112.98 (11)°]. The isocoumarin ring system and the bromobenzene ring are both planar within r.m.s. deviations of 0.015 Å and subtend a dihedral angle of 88.90 (2)°.

The packing diagram (Fig. 2) shows the molecules to be linked by two C—H···O hydrogen bonds (Table 1) and by π–π stacking interactions between the coumarin units and between the bromobenzene rings, with centroid-to-centroid distances ranging from 3.667 (2) to 3.765 (2) Å. A marginal Br···O interaction [Br···O2ⁱ 3.4734 (10) Å; symmetry code: (i) -1 + x, y, -1 + z] is also observed.

Related literature top

For the properties and applications of isocoumarins and 3,4-dihydroisocoumarins, see: Chinworrungsee et al. (2002); Devienne et al. (2002); Mali & Babu (1998); Rama et al. (1998); Waters & Kozlowski (2001). For related structures, see: Abid et al. (2008); Babar et al. (2008).

Experimental top

A mixture of 2-(3-bromophenyl)acetic acid (5 g, 0.023 mol) and oxalyl chloride (2 ml, 0.024 mol) was stirred overnight. Completion of the reaction was indicated by cessation of gas evolution. Excess oxalyl chloride was removed under reduced pressure to afford 2-(3-bromophenyl)acetyl chloride. Homophthalic acid (1.0 g, 0.006 mol) was added and the solution was heated at 473 K for 4 h. The reaction mixture was dissolved in ethyl acetate and aqueous solution of sodium carbonate was added in order to remove the unreacted homophthalic acid. The organic layer was separated, concentrated and chromatographed on silica gel using pet ether as eluent to afford title compound (yield 65%,; m.p. 97–98°C) as a colourless solid. Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. Packing diagram of the title compound viewed perpendicular to the bc plane. C—H···O hydrogen interactions are indicated by dashed lines. H atoms not involved in hydrogen bonding are omitted.
	Fig. 3. Reaction scheme.

3-(3-Bromobenzyl)-1H-isochromen-1-one top

Crystal data top

C₁₆H₁₁BrO₂	Z = 2
M_r = 315.16	F(000) = 316
Triclinic, P1	D_x = 1.673 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4508 (5) Å	Cell parameters from 9750 reflections
b = 8.1824 (6) Å	θ = 2.7–30.7°
c = 11.3663 (8) Å	µ = 3.28 mm⁻¹
α = 90.130 (6)°	T = 103 K
β = 98.392 (7)°	Block, colourless
γ = 113.844 (8)°	0.25 × 0.25 × 0.20 mm
V = 625.58 (8) Å³

Data collection top

Oxford Xcalibur E diffractometer	3449 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2899 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 16.1419 pixels mm^-1	θ_max = 29.6°, θ_min = 3.0°
ω scan	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction 2009)	k = −11→11
T_min = 0.922, T_max = 1.000	l = −15→15
16250 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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.045	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0233P)²] where P = (F_o² + 2F_c²)/3
3449 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₆H₁₁BrO₂	γ = 113.844 (8)°
M_r = 315.16	V = 625.58 (8) Å³
Triclinic, P1	Z = 2
a = 7.4508 (5) Å	Mo Kα radiation
b = 8.1824 (6) Å	µ = 3.28 mm⁻¹
c = 11.3663 (8) Å	T = 103 K
α = 90.130 (6)°	0.25 × 0.25 × 0.20 mm
β = 98.392 (7)°

Data collection top

Oxford Xcalibur E diffractometer	3449 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction 2009)	2899 reflections with I > 2σ(I)
T_min = 0.922, T_max = 1.000	R_int = 0.025
16250 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	0 restraints
wR(F²) = 0.045	H-atom parameters constrained
S = 0.97	Δρ_max = 0.43 e Å⁻³
3449 reflections	Δρ_min = −0.25 e Å⁻³
172 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.

Non-bonded contact:

3.4734 (0.0010) Br - O2_$5 157.19 (0.04) C13 - Br - O2_$5 144.68 (0.08) Br - O2_$5 - C1_$5 Operator for generating equivalent atoms: $5 x - 1, y, z - 1

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 1.8912 (0.0020) x + 7.3803 (0.0014) y + 4.4053 (0.0037) z = 0.7728 (0.0010)

* 0.0088 (0.0008) C10 * -0.0063 (0.0011) C11 * 0.0058 (0.0010) C12 * 0.0167 (0.0011) C13 * 0.0215 (0.0010) C14 * -0.0036 (0.0009) C15 * -0.0224 (0.0011) C16 * -0.0204 (0.0006) Br

Rms deviation of fitted atoms = 0.0151

7.0134 (0.0011) x - 0.6456 (0.0018) y - 2.6242 (0.0032) z = 3.6495 (0.0018)

Angle to previous plane (with approximate e.s.d.) = 88.90 (0.02)

* -0.0183 (0.0009) C10 * -0.0095 (0.0009) O1 * 0.0027 (0.0011) C1 * -0.0081 (0.0008) O2 * 0.0273 (0.0011) C3 * 0.0129 (0.0012) C4 * -0.0052 (0.0011) C5 * -0.0241 (0.0011) C6 * -0.0078 (0.0012) C7 * 0.0144 (0.0012) C8 * 0.0159 (0.0012) C9

Rms deviation of fitted atoms = 0.0152

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
Br	0.13942 (2)	0.205557 (19)	−0.113746 (13)	0.02023 (5)
O1	0.70881 (14)	0.19099 (12)	0.46026 (8)	0.0146 (2)
O2	0.78538 (15)	0.22208 (13)	0.65672 (8)	0.0195 (2)
C1	0.75969 (19)	0.29281 (17)	0.56653 (12)	0.0141 (3)
C2	0.67678 (19)	0.25762 (17)	0.35091 (11)	0.0128 (3)
C3	0.69140 (19)	0.42394 (17)	0.34239 (11)	0.0136 (3)
H3	0.6699	0.4662	0.2661	0.016*
C4	0.73964 (18)	0.54146 (17)	0.44789 (11)	0.0124 (3)
C5	0.7521 (2)	0.71742 (18)	0.44484 (12)	0.0170 (3)
H5	0.7288	0.7643	0.3706	0.020*
C6	0.7982 (2)	0.82214 (18)	0.54931 (13)	0.0182 (3)
H6	0.8045	0.9404	0.5465	0.022*
C7	0.8354 (2)	0.75669 (19)	0.65887 (13)	0.0185 (3)
H7	0.8683	0.8306	0.7301	0.022*
C8	0.8248 (2)	0.58509 (18)	0.66416 (12)	0.0162 (3)
H8	0.8507	0.5406	0.7389	0.019*
C9	0.77565 (19)	0.47639 (17)	0.55899 (11)	0.0126 (3)
C10	0.6231 (2)	0.11432 (17)	0.25339 (11)	0.0161 (3)
H10A	0.4972	0.0138	0.2639	0.019*
H10B	0.7280	0.0682	0.2602	0.019*
C11	0.5989 (2)	0.17984 (17)	0.12982 (11)	0.0144 (3)
C12	0.4136 (2)	0.16677 (17)	0.07491 (11)	0.0146 (3)
H12	0.3011	0.1147	0.1140	0.018*
C13	0.39414 (19)	0.23009 (17)	−0.03706 (12)	0.0143 (3)
C14	0.5553 (2)	0.30743 (18)	−0.09635 (12)	0.0155 (3)
H14	0.5401	0.3518	−0.1726	0.019*
C15	0.7391 (2)	0.31864 (17)	−0.04193 (12)	0.0165 (3)
H15	0.8510	0.3704	−0.0815	0.020*
C16	0.7613 (2)	0.25498 (17)	0.06999 (12)	0.0157 (3)
H16	0.8880	0.2627	0.1061	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.01563 (7)	0.02239 (8)	0.02281 (8)	0.00845 (6)	0.00152 (5)	0.00243 (6)
O1	0.0220 (5)	0.0115 (5)	0.0106 (5)	0.0075 (4)	0.0015 (4)	0.0015 (4)
O2	0.0273 (6)	0.0183 (5)	0.0130 (5)	0.0098 (5)	0.0022 (4)	0.0048 (4)
C1	0.0134 (6)	0.0152 (7)	0.0135 (7)	0.0051 (6)	0.0033 (5)	0.0009 (5)
C2	0.0130 (6)	0.0147 (6)	0.0106 (6)	0.0051 (5)	0.0027 (5)	0.0033 (5)
C3	0.0162 (7)	0.0141 (7)	0.0107 (6)	0.0065 (6)	0.0016 (5)	0.0022 (5)
C4	0.0109 (6)	0.0123 (6)	0.0145 (7)	0.0046 (5)	0.0033 (5)	0.0014 (5)
C5	0.0191 (7)	0.0163 (7)	0.0170 (7)	0.0087 (6)	0.0031 (5)	0.0034 (6)
C6	0.0188 (7)	0.0124 (7)	0.0246 (8)	0.0069 (6)	0.0053 (6)	−0.0005 (6)
C7	0.0181 (7)	0.0183 (7)	0.0183 (7)	0.0062 (6)	0.0045 (6)	−0.0049 (6)
C8	0.0164 (7)	0.0187 (7)	0.0123 (7)	0.0054 (6)	0.0039 (5)	0.0009 (5)
C9	0.0111 (6)	0.0130 (6)	0.0138 (7)	0.0045 (5)	0.0034 (5)	0.0013 (5)
C10	0.0218 (7)	0.0117 (6)	0.0141 (7)	0.0060 (6)	0.0028 (5)	0.0010 (5)
C11	0.0208 (7)	0.0089 (6)	0.0124 (7)	0.0053 (6)	0.0014 (5)	−0.0030 (5)
C12	0.0173 (7)	0.0119 (6)	0.0140 (7)	0.0046 (6)	0.0052 (5)	−0.0014 (5)
C13	0.0147 (6)	0.0121 (6)	0.0155 (7)	0.0058 (5)	0.0001 (5)	−0.0032 (5)
C14	0.0196 (7)	0.0137 (7)	0.0131 (7)	0.0068 (6)	0.0021 (5)	0.0004 (5)
C15	0.0170 (7)	0.0149 (7)	0.0170 (7)	0.0051 (6)	0.0055 (5)	0.0019 (6)
C16	0.0159 (7)	0.0145 (7)	0.0154 (7)	0.0057 (6)	0.0002 (5)	−0.0012 (5)

Geometric parameters (Å, º) top

Br—C13	1.9001 (13)	C11—C16	1.3947 (19)
O1—C1	1.3796 (15)	C12—C13	1.3854 (18)
O1—C2	1.3859 (15)	C13—C14	1.3859 (19)
O2—C1	1.2073 (15)	C14—C15	1.3842 (18)
C1—C9	1.4618 (18)	C15—C16	1.3887 (18)
C2—C3	1.3256 (18)	C3—H3	0.9500
C2—C10	1.4996 (18)	C5—H5	0.9500
C3—C4	1.4426 (18)	C6—H6	0.9500
C4—C9	1.4035 (18)	C7—H7	0.9500
C4—C5	1.4056 (18)	C8—H8	0.9500
C5—C6	1.3787 (19)	C10—H10A	0.9900
C6—C7	1.392 (2)	C10—H10B	0.9900
C7—C8	1.3759 (19)	C12—H12	0.9500
C8—C9	1.3994 (18)	C14—H14	0.9500
C10—C11	1.5166 (18)	C15—H15	0.9500
C11—C12	1.3911 (18)	C16—H16	0.9500

C1—O1—C2	122.56 (10)	C15—C14—C13	118.52 (13)
O2—C1—O1	117.22 (12)	C14—C15—C16	120.63 (13)
O2—C1—C9	126.19 (12)	C15—C16—C11	120.46 (13)
O1—C1—C9	116.59 (11)	C2—C3—H3	119.7
C3—C2—O1	121.65 (12)	C4—C3—H3	119.7
C3—C2—C10	128.78 (12)	C6—C5—H5	119.9
O1—C2—C10	109.56 (11)	C4—C5—H5	119.9
C2—C3—C4	120.62 (12)	C5—C6—H6	119.6
C9—C4—C5	118.50 (12)	C7—C6—H6	119.6
C9—C4—C3	118.22 (12)	C8—C7—H7	119.9
C5—C4—C3	123.28 (12)	C6—C7—H7	119.9
C6—C5—C4	120.19 (13)	C7—C8—H8	120.1
C5—C6—C7	120.77 (13)	C9—C8—H8	120.1
C8—C7—C6	120.14 (13)	C2—C10—H10A	109.0
C7—C8—C9	119.74 (13)	C11—C10—H10A	109.0
C8—C9—C4	120.65 (12)	C2—C10—H10B	109.0
C8—C9—C1	119.01 (12)	C11—C10—H10B	109.0
C4—C9—C1	120.34 (12)	H10A—C10—H10B	107.8
C2—C10—C11	112.98 (11)	C13—C12—H12	120.2
C12—C11—C16	119.06 (12)	C11—C12—H12	120.2
C12—C11—C10	120.17 (12)	C15—C14—H14	120.7
C16—C11—C10	120.77 (12)	C13—C14—H14	120.7
C13—C12—C11	119.64 (12)	C14—C15—H15	119.7
C12—C13—C14	121.67 (13)	C16—C15—H15	119.7
C12—C13—Br	119.50 (10)	C15—C16—H16	119.8
C14—C13—Br	118.81 (10)	C11—C16—H16	119.8

C2—O1—C1—O2	−179.57 (11)	O2—C1—C9—C8	−0.1 (2)
C2—O1—C1—C9	0.95 (17)	O1—C1—C9—C8	179.34 (11)
C1—O1—C2—C3	−0.72 (19)	O2—C1—C9—C4	−179.30 (13)
C1—O1—C2—C10	−179.69 (11)	O1—C1—C9—C4	0.14 (18)
O1—C2—C3—C4	−0.6 (2)	C3—C2—C10—C11	5.0 (2)
C10—C2—C3—C4	178.12 (13)	O1—C2—C10—C11	−176.15 (11)
C2—C3—C4—C9	1.66 (19)	C2—C10—C11—C12	−90.92 (15)
C2—C3—C4—C5	−178.28 (13)	C2—C10—C11—C16	88.60 (15)
C9—C4—C5—C6	−0.22 (19)	C16—C11—C12—C13	−0.72 (19)
C3—C4—C5—C6	179.72 (13)	C10—C11—C12—C13	178.81 (11)
C4—C5—C6—C7	0.9 (2)	C11—C12—C13—C14	−0.27 (19)
C5—C6—C7—C8	−0.6 (2)	C11—C12—C13—Br	178.14 (9)
C6—C7—C8—C9	−0.2 (2)	C12—C13—C14—C15	0.9 (2)
C7—C8—C9—C4	0.9 (2)	Br—C13—C14—C15	−177.54 (10)
C7—C8—C9—C1	−178.34 (13)	C13—C14—C15—C16	−0.50 (19)
C5—C4—C9—C8	−0.63 (19)	C14—C15—C16—C11	−0.5 (2)
C3—C4—C9—C8	179.43 (12)	C12—C11—C16—C15	1.09 (19)
C5—C4—C9—C1	178.56 (12)	C10—C11—C16—C15	−178.44 (12)
C3—C4—C9—C1	−1.38 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.95	2.58	3.4666 (16)	155
C10—H10A···O2ⁱⁱ	0.99	2.50	3.4685 (17)	166

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁BrO₂
M_r	315.16
Crystal system, space group	Triclinic, P1
Temperature (K)	103
a, b, c (Å)	7.4508 (5), 8.1824 (6), 11.3663 (8)
α, β, γ (°)	90.130 (6), 98.392 (7), 113.844 (8)
V (Å³)	625.58 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.28
Crystal size (mm)	0.25 × 0.25 × 0.20

Data collection
Diffractometer	Oxford Xcalibur E diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction 2009)
T_min, T_max	0.922, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	16250, 3449, 2899
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.694

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.045, 0.97
No. of reflections	3449
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.25

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Siemens, 1994).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.95	2.58	3.4666 (16)	155.3
C10—H10A···O2ⁱⁱ	0.99	2.50	3.4685 (17)	166.0

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

Acknowledgements

TMB is grateful to the Higher Education Commission of Pakistan for financial support for a PhD program.

References

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