Sodium 2-iodo­benzene­sulfonate monohydrate

Arshad, M.N.; Tahir, M.N.; Khan, I.U.; Shafiq, M.; Siddiqui, W.A.

doi:10.1107/S1600536808039202

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1628

doi:10.1107/S1600536808039202

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Sodium 2-iodobenzenesulfonate monohydrate

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

^aDepartment of Chemistry, Government College University, Lahore, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 29 October 2008; accepted 21 November 2008; online 29 November 2008)

In the title compound, Na⁺·C₆H₄IO₃S⁻·H₂O, the Na atom is hexacoordinated by O atoms, forming a two-dimensional sheet-like structure in the bc plane, with the iodobenzene rings protruding above and below. Na⋯O contact distances are in the range 2.419 (2)–2.7218 (18) Å and O⋯Na⋯O angles are in the range 73.70 (5)–158.64 (7)°. The crystal structure is stabilized by O—H⋯O and C—H⋯O hydrogen bonds and C—H⋯π interactions. The I atom is disordered over two positions with occupancies of 0.78 (2) and 0.22 (2).

Related literature

For related literature on the synthesis of biologically active benzothiazine derivatives, see: Arshad et al. (2008 ); Chau & Kice (1977 ); Shafiq, Khan et al. (2008 ); Shafiq, Tahir et al. (2008 ); Tahir et al. (2008 ).

Experimental

Crystal data

Na⁺·C₆H₄IO₃S⁻·H₂O
M_r = 324.06
Monoclinic, P 2₁ /c
a = 13.6141 (4) Å
b = 8.8233 (3) Å
c = 7.8493 (3) Å
β = 92.171 (1)°
V = 942.19 (6) Å³
Z = 4
Mo Kα radiation
μ = 3.64 mm⁻¹
T = 296 (2) K
0.25 × 0.17 × 0.15 mm

Data collection

Bruker KAPPA APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.482, T_max = 0.580
10141 measured reflections
2339 independent reflections
2135 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.047
S = 1.05
2339 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O2ⁱ	0.85	1.98	2.824 (2)	174
C6—H6⋯O1	0.93	2.42	2.834 (3)	107
C5—H5⋯Cgⁱ	0.93	2.79	3.661 (3)	156
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ . Cg is the centroid of the benzene ring.

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 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/S1600536808039202/su2075sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039202/su2075Isup2.hkl

checkCIF report

Comment top

In the continuation to our research work on the synthesis of biologically active benzothiazine derivatives (Arshad et al., 2008; Shafiq, Khan, Tahir & Siddiqui, 2008; Shafiq, Tahir, Khan, Ahmad & Siddiqui, 2008; Tahir et al., 2008), we synthesized the title compound, (I).

The molecular structure of compound (I) is illustrated in Fig. 1. The bond lengths and bond angles, as far as the 2-iodobenzenesulfonate is concerned, are similar to those reported for the potassium salt analogue, reported on recently (Arshad et al., 2008). The Na-atom is hexa-coordinated with O-atoms, involving four from the sulfonic groups and two water molecules. The range of the Na···O distances is 2.419 (2)–2.7218 (18) Å, whereas the range of O···Na···O angles is 73.70 (5)–158.64 (7)°. In this way a two-dimensional sheet-like structure in the bc plane is formed, with the iodobenzene rings protruding above and below.

It is interesting that one of the O-atoms of the sulfonic group is not involved in coordination with the Na-atom, but makes an intermolecular hydrogen bond with a water molecule, similar to the situation on the potassium salt analogue mentioned above. Also, one of the H-atoms of the H₂O molecule is not involved in intra or intermolecular H-bonding.

In the crystal structure of compound (I) a two dimensional polymeric network extending along the b axis is formed (Fig. 2). There exist O-H···O and C-H···O hydrogen bonds, and C-H···π-interactions involving the centroid, Cg, of the benzene ring, see Table 1 for details.

Related literature top

For related literature on the synthesis of biologically active benzothiazine derivatives, see: Arshad et al. (2008); Chau & Kice (1977); Shafiq, Khan et al. (2008); Shafiq, Tahir et al. (2008); Tahir et al. (2008). Cg is the centroid of the benzene ring

Experimental top

The title compound was prepared following the method used by Chau & Kice (1977). Suitable crystals for X-ray analysis were obtained from the reaction mixture.

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 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. Molecular structure of compound (I), with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view along the c axis of the crystal packing in compound (I), showing the coordination of the O-atoms with the sodium atom and the hydrogen bonding involving the water molecules (H-atoms not involved in hydrogen bonding have been removed for clarity).

Sodium 2-iodobenzenesulfonate monohydrate top

Crystal data top

Na⁺·C₆H₄IO₃S⁻·H2O	F(000) = 616
M_r = 324.06	D_x = 2.285 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2339 reflections
a = 13.6141 (4) Å	θ = 1.5–28.3°
b = 8.8233 (3) Å	µ = 3.64 mm⁻¹
c = 7.8493 (3) Å	T = 296 K
β = 92.171 (1)°	Prismatic, colorless
V = 942.19 (6) Å³	0.25 × 0.17 × 0.15 mm
Z = 4

Data collection top

Bruker KAPPA APEXII CCD diffractometer	2339 independent reflections
Radiation source: fine-focus sealed tube	2135 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.3°, θ_min = 1.5°
ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
T_min = 0.482, T_max = 0.580	l = −10→10
10141 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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.047	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0176P)² + 0.7234P] where P = (F_o² + 2F_c²)/3
2339 reflections	(Δ/σ)_max = 0.009
128 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

Na⁺·C₆H₄IO₃S⁻·H2O	V = 942.19 (6) Å³
M_r = 324.06	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.6141 (4) Å	µ = 3.64 mm⁻¹
b = 8.8233 (3) Å	T = 296 K
c = 7.8493 (3) Å	0.25 × 0.17 × 0.15 mm
β = 92.171 (1)°

Data collection top

Bruker KAPPA APEXII CCD diffractometer	2339 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2135 reflections with I > 2σ(I)
T_min = 0.482, T_max = 0.580	R_int = 0.024
10141 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	0 restraints
wR(F²) = 0.047	H-atom parameters constrained
S = 1.05	Δρ_max = 0.42 e Å⁻³
2339 reflections	Δρ_min = −0.42 e Å⁻³
128 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	Occ. (<1)
I1A	0.19343 (9)	−0.1923 (2)	0.55095 (18)	0.0385 (2)	0.78 (2)
I1B	0.1984 (5)	−0.1716 (17)	0.5644 (12)	0.0628 (13)	0.22 (2)
S1	0.37585 (3)	0.02639 (5)	0.34970 (6)	0.0236 (1)
Na	0.51091 (7)	0.29771 (10)	0.49492 (12)	0.0402 (3)
O1	0.42883 (11)	0.14214 (18)	0.2606 (2)	0.0369 (5)
O2	0.38308 (12)	0.0514 (2)	0.53146 (19)	0.0461 (6)
O3	0.40017 (11)	−0.12539 (18)	0.2976 (2)	0.0390 (5)
O4	0.39172 (13)	0.4952 (2)	0.38765 (19)	0.0413 (5)
C1	0.24956 (13)	0.0530 (2)	0.2877 (2)	0.0227 (5)
C2	0.17328 (14)	−0.0292 (2)	0.3573 (2)	0.0251 (5)
C3	0.07722 (15)	−0.0064 (3)	0.2991 (3)	0.0328 (6)
C4	0.05587 (16)	0.0976 (3)	0.1724 (3)	0.0386 (7)
C5	0.13033 (18)	0.1803 (3)	0.1044 (3)	0.0412 (7)
C6	0.22673 (16)	0.1593 (3)	0.1618 (3)	0.0332 (6)
H3	0.02673	−0.06165	0.34590	0.0393*
H4	−0.00875	0.11181	0.13299	0.0463*
H4A	0.38645	0.48643	0.28018	0.0496*
H4B	0.33495	0.51683	0.41658	0.0496*
H5	0.11586	0.25088	0.01914	0.0495*
H6	0.27653	0.21667	0.11578	0.0398*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1A	0.0425 (3)	0.0384 (5)	0.0345 (3)	−0.0046 (4)	0.0010 (2)	0.0146 (3)
I1B	0.0625 (16)	0.071 (3)	0.0543 (18)	−0.0264 (19)	−0.0055 (11)	0.0310 (15)
S1	0.0214 (2)	0.0248 (2)	0.0243 (2)	0.0002 (2)	−0.0019 (2)	−0.0017 (2)
Na	0.0466 (5)	0.0325 (5)	0.0407 (5)	0.0011 (4)	−0.0087 (4)	−0.0053 (4)
O1	0.0285 (7)	0.0346 (8)	0.0478 (9)	−0.0059 (6)	0.0027 (6)	0.0055 (7)
O2	0.0349 (8)	0.0784 (13)	0.0245 (7)	−0.0004 (8)	−0.0055 (6)	−0.0061 (8)
O3	0.0301 (8)	0.0252 (8)	0.0612 (10)	0.0051 (6)	−0.0043 (7)	−0.0076 (7)
O4	0.0447 (9)	0.0519 (10)	0.0274 (7)	0.0000 (8)	0.0018 (7)	−0.0009 (7)
C1	0.0224 (8)	0.0227 (9)	0.0227 (8)	0.0025 (7)	−0.0012 (7)	−0.0016 (7)
C2	0.0277 (9)	0.0240 (9)	0.0234 (9)	0.0001 (7)	−0.0006 (7)	−0.0011 (7)
C3	0.0261 (9)	0.0349 (12)	0.0373 (11)	−0.0030 (8)	0.0008 (8)	−0.0037 (9)
C4	0.0283 (10)	0.0430 (13)	0.0438 (12)	0.0083 (9)	−0.0091 (9)	−0.0036 (10)
C5	0.0405 (12)	0.0413 (14)	0.0413 (12)	0.0096 (10)	−0.0066 (10)	0.0141 (10)
C6	0.0333 (10)	0.0316 (11)	0.0346 (11)	0.0019 (8)	0.0017 (8)	0.0091 (9)

Geometric parameters (Å, º) top

I1A—C2	2.104 (2)	O4—H4B	0.8400
I1B—C2	2.073 (12)	O4—H4A	0.8500
S1—O1	1.4459 (16)	C1—C6	1.389 (3)
S1—O2	1.4433 (16)	C1—C2	1.395 (3)
S1—O3	1.4424 (16)	C2—C3	1.384 (3)
S1—C1	1.7846 (18)	C3—C4	1.376 (4)
Na—O1	2.5219 (18)	C4—C5	1.373 (3)
Na—O4	2.505 (2)	C5—C6	1.384 (3)
Na—O3ⁱ	2.7218 (18)	C3—H3	0.9300
Na—O3ⁱⁱ	2.5060 (18)	C4—H4	0.9300
Na—O4ⁱⁱⁱ	2.419 (2)	C5—H5	0.9300
Na—O1^iv	2.4609 (18)	C6—H6	0.9300

I1A···O2	3.368 (2)	O4···O1^iv	3.191 (2)
I1A···O3	3.557 (2)	O4···O1ⁱ	3.036 (2)
I1A···C1^v	3.750 (2)	O1···H4A^viii	2.8900
I1A···I1A^vi	4.055 (2)	O1···H6	2.4200
I1A···I1A^v	4.055 (2)	O2···H6^iv	2.6100
I1A···C2^v	3.456 (2)	O2···H4A^iv	1.9800
I1A···C3^v	3.688 (3)	C1···I1A^vi	3.750 (2)
I1B···O3	3.540 (8)	C1···I1B^vi	3.846 (14)
I1B···O2	3.211 (11)	C2···I1A^vi	3.456 (2)
I1B···C3^v	3.797 (13)	C2···I1B^vi	3.526 (13)
I1B···C1^v	3.846 (14)	C3···I1A^vi	3.688 (3)
I1B···C2^v	3.526 (13)	C3···I1B^vi	3.797 (13)
I1A···H4^vii	3.3300	C4···C4^x	3.506 (3)
S1···O2ⁱⁱ	3.4468 (17)	C2···H5^iv	2.8900
O1···O3ⁱ	3.149 (2)	C3···H5^iv	2.8800
O1···O4^viii	3.036 (2)	C4···H4^x	3.0700
O1···O4^ix	3.191 (2)	C6···H4B^ix	2.9200
O2···S1ⁱⁱ	3.4468 (17)	H4···I1A^xi	3.3300
O2···I1B	3.211 (11)	H4···C4^x	3.0700
O2···I1A	3.368 (2)	H4A···O2^ix	1.9800
O2···O4^iv	2.824 (2)	H4B···C6^iv	2.9200
O3···I1B	3.540 (8)	H5···C2^ix	2.8900
O3···O1^viii	3.149 (2)	H5···C3^ix	2.8800
O3···I1A	3.557 (2)	H6···O1	2.4200
O4···O2^ix	2.824 (2)	H6···O2^ix	2.6100

O1—S1—O2	110.70 (10)	Na—O4—Naⁱⁱⁱ	93.37 (7)
O1—S1—O3	113.24 (9)	Naⁱⁱⁱ—O4—H4A	118.00
O1—S1—C1	105.56 (9)	Naⁱⁱⁱ—O4—H4B	103.00
O2—S1—O3	114.48 (10)	Na—O4—H4A	107.00
O2—S1—C1	106.16 (9)	Na—O4—H4B	131.00
O3—S1—C1	105.90 (9)	H4A—O4—H4B	104.00
O1—Na—O4	82.53 (6)	C2—C1—C6	118.68 (17)
O1—Na—O3ⁱ	73.70 (5)	S1—C1—C6	118.04 (14)
O1—Na—O3ⁱⁱ	109.48 (6)	S1—C1—C2	123.27 (13)
O1—Na—O4ⁱⁱⁱ	155.53 (7)	I1A—C2—C3	115.71 (15)
O1—Na—O1^iv	122.18 (6)	I1A—C2—C1	124.06 (14)
O3ⁱ—Na—O4	81.15 (6)	I1B—C2—C3	118.2 (2)
O3ⁱⁱ—Na—O4	158.64 (7)	C1—C2—C3	120.23 (17)
O4—Na—O4ⁱⁱⁱ	86.63 (6)	I1B—C2—C1	121.3 (2)
O1^iv—Na—O4	79.96 (6)	C2—C3—C4	120.5 (2)
O3ⁱ—Na—O3ⁱⁱ	118.69 (6)	C3—C4—C5	119.8 (2)
O3ⁱ—Na—O4ⁱⁱⁱ	83.01 (6)	C4—C5—C6	120.5 (2)
O1^iv—Na—O3ⁱ	153.11 (6)	C1—C6—C5	120.4 (2)
O3ⁱⁱ—Na—O4ⁱⁱⁱ	88.08 (6)	C2—C3—H3	120.00
O1^iv—Na—O3ⁱⁱ	78.69 (6)	C4—C3—H3	120.00
O1^iv—Na—O4ⁱⁱⁱ	76.94 (6)	C3—C4—H4	120.00
S1—O1—Na	104.30 (8)	C5—C4—H4	120.00
S1—O1—Na^ix	144.40 (10)	C4—C5—H5	120.00
Na—O1—Na^ix	107.32 (6)	C6—C5—H5	120.00
S1—O3—Na^viii	125.79 (9)	C1—C6—H6	120.00
S1—O3—Naⁱⁱ	119.31 (9)	C5—C6—H6	120.00
Na^viii—O3—Naⁱⁱ	100.23 (6)

O2—S1—O1—Na	4.83 (11)	O3ⁱ—Na—O4—Naⁱⁱⁱ	−83.44 (6)
O2—S1—O1—Na^ix	156.95 (15)	O3ⁱⁱ—Na—O4—Naⁱⁱⁱ	75.95 (19)
O3—S1—O1—Na	−125.30 (9)	O4ⁱⁱⁱ—Na—O4—Naⁱⁱⁱ	0.00 (7)
O3—S1—O1—Na^ix	26.83 (19)	O1^iv—Na—O4—Naⁱⁱⁱ	77.33 (6)
C1—S1—O1—Na	119.29 (8)	O1—Na—O3ⁱ—S1ⁱ	136.29 (11)
C1—S1—O1—Na^ix	−88.58 (16)	O1—Na—O3ⁱ—Na^ix	−1.72 (6)
O1—S1—O3—Na^viii	−18.05 (13)	O4—Na—O3ⁱ—S1ⁱ	51.55 (11)
O1—S1—O3—Naⁱⁱ	112.93 (10)	O4—Na—O3ⁱ—Na^ix	−86.47 (6)
O2—S1—O3—Na^viii	−146.24 (10)	O1—Na—O3ⁱⁱ—S1ⁱⁱ	19.44 (12)
O2—S1—O3—Naⁱⁱ	−15.26 (13)	O1—Na—O3ⁱⁱ—Na^iv	−122.08 (6)
C1—S1—O3—Na^viii	97.16 (10)	O4—Na—O3ⁱⁱ—S1ⁱⁱ	141.17 (16)
C1—S1—O3—Naⁱⁱ	−131.86 (9)	O4—Na—O3ⁱⁱ—Na^iv	−0.4 (2)
O1—S1—C1—C2	−174.65 (15)	O1—Na—O4ⁱⁱⁱ—Naⁱⁱⁱ	63.66 (18)
O1—S1—C1—C6	6.44 (18)	O4—Na—O4ⁱⁱⁱ—Naⁱⁱⁱ	0.00 (6)
O2—S1—C1—C2	−57.08 (17)	O1—Na—O1^iv—S1^iv	−100.39 (17)
O2—S1—C1—C6	124.01 (17)	O1—Na—O1^iv—Na^iv	107.94 (8)
O3—S1—C1—C2	65.01 (16)	O4—Na—O1^iv—S1^iv	−25.90 (16)
O3—S1—C1—C6	−113.91 (17)	O4—Na—O1^iv—Na^iv	−177.57 (7)
O4—Na—O1—S1	−111.84 (9)	S1—C1—C2—I1A	2.0 (2)
O4—Na—O1—Na^ix	84.73 (7)	S1—C1—C2—C3	−177.78 (16)
O3ⁱ—Na—O1—S1	165.24 (9)	C6—C1—C2—I1A	−179.11 (16)
O3ⁱ—Na—O1—Na^ix	1.81 (6)	C6—C1—C2—C3	1.1 (3)
O3ⁱⁱ—Na—O1—S1	49.96 (10)	S1—C1—C6—C5	177.54 (18)
O3ⁱⁱ—Na—O1—Na^ix	−113.48 (7)	C2—C1—C6—C5	−1.4 (3)
O4ⁱⁱⁱ—Na—O1—S1	−176.30 (14)	I1A—C2—C3—C4	−179.9 (2)
O4ⁱⁱⁱ—Na—O1—Na^ix	20.27 (19)	C1—C2—C3—C4	−0.1 (3)
O1^iv—Na—O1—S1	−38.71 (11)	C2—C3—C4—C5	−0.6 (4)
O1^iv—Na—O1—Na^ix	157.85 (7)	C3—C4—C5—C6	0.3 (4)
O1—Na—O4—Naⁱⁱⁱ	−158.02 (6)	C4—C5—C6—C1	0.7 (4)

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) x, −y+1/2, z+1/2; (v) x, −y−1/2, z+1/2; (vi) x, −y−1/2, z−1/2; (vii) −x, y−1/2, −z+1/2; (viii) −x+1, y−1/2, −z+1/2; (ix) x, −y+1/2, z−1/2; (x) −x, −y, −z; (xi) −x, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O2^ix	0.85	1.98	2.824 (2)	174
C6—H6···O1	0.93	2.42	2.834 (3)	107
C5—H5···Cg^ix	0.93	2.79	3.661 (3)	156

Symmetry code: (ix) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	Na⁺·C₆H₄IO₃S⁻·H2O
M_r	324.06
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.6141 (4), 8.8233 (3), 7.8493 (3)
β (°)	92.171 (1)
V (Å³)	942.19 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.64
Crystal size (mm)	0.25 × 0.17 × 0.15

Data collection
Diffractometer	Bruker KAPPA APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.482, 0.580
No. of measured, independent and observed [I > 2σ(I)] reflections	10141, 2339, 2135
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.047, 1.05
No. of reflections	2339
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.42

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
O4—H4A···O2ⁱ	0.85	1.98	2.824 (2)	174
C6—H6···O1	0.93	2.42	2.834 (3)	107
C5—H5···Cgⁱ	0.93	2.79	3.661 (3)	156

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

MNA greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing him a Scholarship under the Indigenous PhD Program (PIN 042–120607–PS2–183).

References

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