Sodium N,2-dichloro­benzene­sulfonamidate sesquihydrate

Gowda, B.T.; Foro, S.; Shakuntala, K.; Fuess, H.

doi:10.1107/S1600536810009864

organic compounds

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Volume 66| Part 4| April 2010| Page o889

doi:10.1107/S1600536810009864

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Sodium N,2-dichlorobenzenesulfonamidate sesquihydrate

B. Thimme Gowda,^a ^* Sabine Foro,^b K. Shakuntala ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 6 March 2010; accepted 16 March 2010; online 20 March 2010)

In the title compound, Na⁺·C₆H₄Cl₂NO₂S⁻·1.5H₂O, one of the water molecules lies on a twofold axis. There is no interaction between the N atom and the sodium ion. The sodium ion exhibits a pseudo-octahedral coordination defined by three water O atoms and three sulfonyl O atoms from three different anions. The S—N distance of 1.588 (2) Å is consistent with an S=N double bond. The crystal structure is stabilized by O—H⋯N and O—H⋯Cl hydrogen bonds.

Related literature

For background to N-haloarylsulfonamides, see: Gowda et al. (2005 ). For related structures, see: Gowda et al. (2007 , 2009 ); George et al. (2000 ); Olmstead & Power (1986 ).

Experimental

Crystal data

Na⁺·C₆H₄Cl₂NO₂S⁻·1.5H₂O
M_r = 275.08
Monoclinic, C 2/c
a = 11.1288 (7) Å
b = 6.6724 (4) Å
c = 28.144 (2) Å
β = 102.274 (6)°
V = 2042.1 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.87 mm⁻¹
T = 299 K
0.46 × 0.36 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.691, T_max = 0.794
6590 measured reflections
2076 independent reflections
1944 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.069
S = 1.15
2076 reflections
141 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H31⋯N1ⁱ	0.79 (2)	2.15 (2)	2.926 (2)	166 (3)
O3—H32⋯Cl1ⁱⁱ	0.81 (2)	2.67 (2)	3.4782 (16)	171 (2)
O4—H41⋯N1ⁱⁱ	0.81 (2)	2.19 (2)	3.005 (2)	176 (2)
Symmetry codes: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009864/bx2268sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810009864/bx2268Isup2.hkl

checkCIF report

Comment top

In the present work, as a part of exploring the substituent effects on the solid-state structures of N-halo arylsulfonamidates (Gowda et al., 2005; 2007; 2009), the structure of sodium N-chloro-2-chloro- benzenesulfonamidate (I) has been determined (Fig. 1). The structure of (I) resembles the sodium salts of N-chloro-4-chlorobenzenesulfonamidate (Gowda et al., 2007), N-chloro-2-methylbenzenesulfonamidate (Gowda et al., 2009), and other sodium N-chloro- arylsulfonamidates (George et al., 2000; Olmstead & Power, 1986).

The sodium ion shows pseudo-octahedral coordination defined by three water-O atoms and by three sulfonyl-O atoms derived from three different anions. There is no interaction between the nitrogen and sodium ions. The S—N distance of 1.588 (2)Å is consistent with a S—N double bond and is in agreement with those observed with related N-chloro arylsulfonamides.

The Packing diagram consists of a two-dimensional polymeric layer running parallel to the ac plane (Fig. 2). The molecular packing is stabilized by N-H···O and O-H···Cl hydrogen bonds (Table 1)

Related literature top

For background to N-haloarylsulfonamides, see: Gowda et al. (2005). For related structures, see: Gowda et al. (2007, 2009); George et al. (2000); Olmstead & Power (1986).

Experimental top

The title compound was prepared according to the literature method (Gowda et al., 2005; 2007). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound used in X-ray diffraction studies were obtained from a slow evaporation of its chloroform solution at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); 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. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

Sodium N,2-dichlorobenzenesulfonamidate sesquihydrate top

Crystal data top

Na⁺·C₆H₄Cl₂NO₂S⁻·1.5H₂O	F(000) = 1112
M_r = 275.08	D_x = 1.789 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2816 reflections
a = 11.1288 (7) Å	θ = 3.0–27.9°
b = 6.6724 (4) Å	µ = 0.87 mm⁻¹
c = 28.144 (2) Å	T = 299 K
β = 102.274 (6)°	Prism, colourless
V = 2042.1 (2) Å³	0.46 × 0.36 × 0.28 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2076 independent reflections
Radiation source: fine-focus sealed tube	1944 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
Rotation method data acquisition using ω and phi scans	θ_max = 26.4°, θ_min = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→13
T_min = 0.691, T_max = 0.794	k = −8→6
6590 measured reflections	l = −33→35

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ²(F_o²) + (0.0246P)² + 3.4504P] where P = (F_o² + 2F_c²)/3
2076 reflections	(Δ/σ)_max = 0.006
141 parameters	Δρ_max = 0.36 e Å⁻³
3 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

Na⁺·C₆H₄Cl₂NO₂S⁻·1.5H₂O	V = 2042.1 (2) Å³
M_r = 275.08	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 11.1288 (7) Å	µ = 0.87 mm⁻¹
b = 6.6724 (4) Å	T = 299 K
c = 28.144 (2) Å	0.46 × 0.36 × 0.28 mm
β = 102.274 (6)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2076 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1944 reflections with I > 2σ(I)
T_min = 0.691, T_max = 0.794	R_int = 0.014
6590 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	3 restraints
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	Δρ_max = 0.36 e Å⁻³
2076 reflections	Δρ_min = −0.28 e Å⁻³
141 parameters

Special details top

Experimental. (CrysAlis RED; Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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 > 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
C1	0.31355 (16)	0.8280 (3)	0.10792 (6)	0.0208 (4)
C2	0.39097 (18)	0.8966 (3)	0.07759 (7)	0.0257 (4)
C3	0.3434 (2)	0.9809 (3)	0.03289 (8)	0.0376 (5)
H3	0.3951	1.0261	0.0132	0.045*
C4	0.2181 (2)	0.9965 (4)	0.01810 (8)	0.0454 (6)
H4	0.1843	1.0514	−0.0122	0.054*
C5	0.1413 (2)	0.9312 (4)	0.04792 (9)	0.0431 (6)
H5	0.0566	0.9446	0.0375	0.052*
C6	0.18813 (18)	0.8472 (3)	0.09260 (7)	0.0301 (4)
H6	0.1358	0.8038	0.1122	0.036*
Cl1	0.38325 (5)	0.35684 (8)	0.123234 (19)	0.03468 (14)
Cl2	0.54842 (5)	0.88282 (9)	0.09392 (2)	0.04180 (16)
N1	0.45784 (14)	0.5415 (2)	0.16212 (6)	0.0255 (3)
Na1	0.14395 (7)	0.50352 (13)	0.23560 (3)	0.03065 (19)
O1	0.25555 (13)	0.6627 (2)	0.18286 (5)	0.0329 (3)
O2	0.44039 (12)	0.8680 (2)	0.19636 (5)	0.0295 (3)
O3	0.29191 (13)	0.6793 (2)	0.29703 (5)	0.0333 (3)
H31	0.3538 (18)	0.627 (4)	0.3106 (9)	0.040*
H32	0.258 (2)	0.718 (4)	0.3182 (8)	0.040*
O4	0.0000	0.7742 (3)	0.2500	0.0336 (5)
H41	0.013 (2)	0.852 (3)	0.2729 (7)	0.040*
S1	0.36626 (4)	0.71995 (7)	0.166416 (15)	0.02023 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0244 (9)	0.0166 (8)	0.0201 (8)	0.0008 (7)	0.0022 (7)	−0.0003 (7)
C2	0.0290 (10)	0.0207 (9)	0.0277 (9)	−0.0013 (8)	0.0068 (8)	−0.0009 (8)
C3	0.0540 (14)	0.0311 (11)	0.0293 (11)	−0.0020 (10)	0.0129 (10)	0.0059 (9)
C4	0.0605 (15)	0.0406 (13)	0.0279 (11)	0.0060 (12)	−0.0068 (10)	0.0108 (10)
C5	0.0355 (12)	0.0442 (13)	0.0412 (12)	0.0054 (10)	−0.0106 (9)	0.0065 (11)
C6	0.0239 (9)	0.0331 (11)	0.0310 (10)	0.0007 (8)	0.0008 (8)	0.0010 (9)
Cl1	0.0399 (3)	0.0266 (3)	0.0380 (3)	−0.0038 (2)	0.0092 (2)	−0.0080 (2)
Cl2	0.0281 (3)	0.0487 (3)	0.0520 (3)	−0.0023 (2)	0.0163 (2)	0.0120 (3)
N1	0.0243 (8)	0.0226 (8)	0.0269 (8)	0.0010 (7)	−0.0002 (6)	−0.0014 (7)
Na1	0.0281 (4)	0.0325 (4)	0.0328 (4)	−0.0052 (3)	0.0097 (3)	0.0006 (3)
O1	0.0272 (7)	0.0430 (9)	0.0309 (7)	−0.0009 (6)	0.0116 (6)	0.0065 (7)
O2	0.0295 (7)	0.0308 (8)	0.0252 (7)	−0.0014 (6)	−0.0007 (5)	−0.0081 (6)
O3	0.0245 (7)	0.0408 (9)	0.0333 (8)	0.0014 (7)	0.0035 (6)	−0.0031 (7)
O4	0.0432 (12)	0.0244 (11)	0.0291 (11)	0.000	−0.0015 (9)	0.000
S1	0.0197 (2)	0.0233 (2)	0.0173 (2)	−0.00026 (17)	0.00302 (15)	0.00009 (17)

Geometric parameters (Å, º) top

C1—C6	1.376 (3)	Na1—O2ⁱ	2.4710 (15)
C1—C2	1.412 (3)	Na1—O2ⁱⁱ	2.4759 (15)
C1—S1	1.7786 (18)	Na1—O4	2.5035 (18)
C2—C3	1.377 (3)	Na1—O3ⁱⁱ	2.5120 (18)
C2—Cl2	1.717 (2)	Na1—S1ⁱⁱ	3.3661 (9)
C3—C4	1.372 (3)	O1—S1	1.4562 (14)
C3—H3	0.9300	O2—S1	1.4390 (14)
C4—C5	1.389 (4)	O2—Na1ⁱⁱⁱ	2.4710 (15)
C4—H4	0.9300	O2—Na1^iv	2.4759 (15)
C5—C6	1.374 (3)	O3—Na1^iv	2.5120 (18)
C5—H5	0.9300	O3—H31	0.792 (16)
C6—H6	0.9300	O3—H32	0.811 (16)
Cl1—N1	1.7376 (16)	O4—Na1^v	2.5035 (18)
N1—S1	1.5883 (16)	O4—H41	0.814 (16)
Na1—O1	2.3785 (15)	S1—Na1^iv	3.3661 (9)
Na1—O3	2.4220 (17)

C6—C1—C2	119.28 (17)	O2ⁱⁱ—Na1—O3ⁱⁱ	98.75 (6)
C6—C1—S1	116.14 (14)	O4—Na1—O3ⁱⁱ	157.17 (5)
C2—C1—S1	124.58 (14)	O1—Na1—S1ⁱⁱ	151.07 (5)
C3—C2—C1	121.30 (19)	O3—Na1—S1ⁱⁱ	79.85 (4)
C3—C2—Cl2	116.02 (16)	O2ⁱ—Na1—S1ⁱⁱ	88.45 (4)
C1—C2—Cl2	122.68 (15)	O2ⁱⁱ—Na1—S1ⁱⁱ	22.58 (3)
C4—C3—C2	118.5 (2)	O4—Na1—S1ⁱⁱ	97.97 (3)
C4—C3—H3	120.8	O3ⁱⁱ—Na1—S1ⁱⁱ	82.95 (4)
C2—C3—H3	120.8	S1—O1—Na1	154.80 (9)
C3—C4—C5	120.6 (2)	S1—O2—Na1ⁱⁱⁱ	150.45 (9)
C3—C4—H4	119.7	S1—O2—Na1^iv	116.06 (8)
C5—C4—H4	119.7	Na1ⁱⁱⁱ—O2—Na1^iv	89.02 (5)
C6—C5—C4	121.3 (2)	Na1—O3—Na1^iv	111.04 (6)
C6—C5—H5	119.4	Na1—O3—H31	121.4 (19)
C4—C5—H5	119.4	Na1^iv—O3—H31	105.4 (19)
C5—C6—C1	119.1 (2)	Na1—O3—H32	108.9 (19)
C5—C6—H6	120.5	Na1^iv—O3—H32	102.1 (19)
C1—C6—H6	120.5	H31—O3—H32	106 (3)
S1—N1—Cl1	110.56 (9)	Na1^v—O4—Na1	87.67 (8)
O1—Na1—O3	82.14 (6)	Na1^v—O4—H41	109.7 (18)
O1—Na1—O2ⁱ	115.80 (6)	Na1—O4—H41	125.3 (18)
O3—Na1—O2ⁱ	156.33 (6)	O2—S1—O1	114.36 (9)
O1—Na1—O2ⁱⁱ	168.48 (6)	O2—S1—N1	105.17 (8)
O3—Na1—O2ⁱⁱ	86.38 (6)	O1—S1—N1	115.30 (9)
O2ⁱ—Na1—O2ⁱⁱ	75.50 (6)	O2—S1—C1	107.39 (9)
O1—Na1—O4	102.47 (6)	O1—S1—C1	105.41 (8)
O3—Na1—O4	84.05 (5)	N1—S1—C1	108.91 (8)
O2ⁱ—Na1—O4	77.23 (5)	O2—S1—Na1^iv	41.36 (6)
O2ⁱⁱ—Na1—O4	77.14 (5)	O1—S1—Na1^iv	73.08 (6)
O1—Na1—O3ⁱⁱ	85.97 (6)	N1—S1—Na1^iv	128.14 (6)
O3—Na1—O3ⁱⁱ	118.37 (5)	C1—S1—Na1^iv	117.93 (6)
O2ⁱ—Na1—O3ⁱⁱ	79.99 (5)

C6—C1—C2—C3	−0.5 (3)	O2ⁱⁱ—Na1—O4—Na1^v	−38.86 (3)
S1—C1—C2—C3	−179.26 (16)	O3ⁱⁱ—Na1—O4—Na1^v	43.09 (13)
C6—C1—C2—Cl2	178.96 (16)	S1ⁱⁱ—Na1—O4—Na1^v	−47.647 (17)
S1—C1—C2—Cl2	0.2 (2)	Na1ⁱⁱⁱ—O2—S1—O1	141.67 (17)
C1—C2—C3—C4	−0.2 (3)	Na1^iv—O2—S1—O1	−3.82 (12)
Cl2—C2—C3—C4	−179.70 (18)	Na1ⁱⁱⁱ—O2—S1—N1	14.2 (2)
C2—C3—C4—C5	0.9 (4)	Na1^iv—O2—S1—N1	−131.33 (9)
C3—C4—C5—C6	−0.8 (4)	Na1ⁱⁱⁱ—O2—S1—C1	−101.75 (18)
C4—C5—C6—C1	0.1 (4)	Na1^iv—O2—S1—C1	112.77 (9)
C2—C1—C6—C5	0.5 (3)	Na1ⁱⁱⁱ—O2—S1—Na1^iv	145.5 (2)
S1—C1—C6—C5	179.42 (17)	Na1—O1—S1—O2	−71.7 (2)
O3—Na1—O1—S1	50.3 (2)	Na1—O1—S1—N1	50.4 (3)
O2ⁱ—Na1—O1—S1	−145.9 (2)	Na1—O1—S1—C1	170.6 (2)
O2ⁱⁱ—Na1—O1—S1	45.6 (5)	Na1—O1—S1—Na1^iv	−74.3 (2)
O4—Na1—O1—S1	132.4 (2)	Cl1—N1—S1—O2	−175.92 (9)
O3ⁱⁱ—Na1—O1—S1	−69.0 (2)	Cl1—N1—S1—O1	57.14 (12)
S1ⁱⁱ—Na1—O1—S1	−1.5 (3)	Cl1—N1—S1—C1	−61.07 (11)
O1—Na1—O3—Na1^iv	31.28 (6)	Cl1—N1—S1—Na1^iv	144.96 (6)
O2ⁱ—Na1—O3—Na1^iv	−109.93 (14)	C6—C1—S1—O2	−118.21 (15)
O2ⁱⁱ—Na1—O3—Na1^iv	−149.66 (7)	C2—C1—S1—O2	60.61 (18)
O4—Na1—O3—Na1^iv	−72.23 (6)	C6—C1—S1—O1	4.11 (17)
O3ⁱⁱ—Na1—O3—Na1^iv	112.35 (9)	C2—C1—S1—O1	−177.07 (16)
S1ⁱⁱ—Na1—O3—Na1^iv	−171.45 (6)	C6—C1—S1—N1	128.38 (15)
O1—Na1—O4—Na1^v	152.95 (5)	C2—C1—S1—N1	−52.80 (18)
O3—Na1—O4—Na1^v	−126.49 (5)	C6—C1—S1—Na1^iv	−74.61 (16)
O2ⁱ—Na1—O4—Na1^v	38.93 (4)	C2—C1—S1—Na1^iv	104.21 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···N1^vi	0.79 (2)	2.15 (2)	2.926 (2)	166 (3)
O3—H32···Cl1^iv	0.81 (2)	2.67 (2)	3.4782 (16)	171 (2)
O4—H41···N1^iv	0.81 (2)	2.19 (2)	3.005 (2)	176 (2)

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

Experimental details

Crystal data
Chemical formula	Na⁺·C₆H₄Cl₂NO₂S⁻·1.5H₂O
M_r	275.08
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	299
a, b, c (Å)	11.1288 (7), 6.6724 (4), 28.144 (2)
β (°)	102.274 (6)
V (Å³)	2042.1 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.87
Crystal size (mm)	0.46 × 0.36 × 0.28

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.691, 0.794
No. of measured, independent and observed [I > 2σ(I)] reflections	6590, 2076, 1944
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.069, 1.15
No. of reflections	2076
No. of parameters	141
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.28

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···N1ⁱ	0.792 (16)	2.151 (17)	2.926 (2)	166 (3)
O3—H32···Cl1ⁱⁱ	0.811 (16)	2.674 (17)	3.4782 (16)	171 (2)
O4—H41···N1ⁱⁱ	0.814 (16)	2.192 (16)	3.005 (2)	176 (2)

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

Acknowledgements

KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

References

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