2,4-Dichloro-N-(3,5-dimethyl­phen­yl)benzene­sulfonamide

Rodrigues, V.Z.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536811040189

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2842

doi:10.1107/S1600536811040189

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2,4-Dichloro-N-(3,5-dimethylphenyl)benzenesulfonamide

Vinola Z. Rodrigues,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^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 23 September 2011; accepted 29 September 2011; online 5 October 2011)

In the crystal of the title compound, C₁₄H₁₃Cl₂NO₂S, the N—H bond in the C—SO₂—NH—C segment is syn to one of the meta-methyl groups in the aniline benzene ring and anti to the other. Further, the conformation of the N—C bond in the C—SO₂—NH—C segment is gauche with respect to the S=O bonds. The C—SO₂—NH—C torsion angle is 54.9 (2)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 82.8 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds. There are also weak C—H⋯O hydrogen bonds between these dimers.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ). For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001 ). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2003 ), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ) and on N-(aryl)-arylsulfonamides, see: Gelbrich et al. (2007 ); Perlovich et al. (2006 ); Gowda & Kumar (2003 ); Rodrigues et al. (2011 ).

Experimental

Crystal data

C₁₄H₁₃Cl₂NO₂S
M_r = 330.21
Monoclinic, C 2/c
a = 23.067 (2) Å
b = 8.0794 (5) Å
c = 16.470 (1) Å
β = 101.575 (7)°
V = 3007.0 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.57 mm⁻¹
T = 293 K
0.50 × 0.46 × 0.42 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 = 0.764, T_max = 0.796
10045 measured reflections
3067 independent reflections
2555 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.124
S = 1.09
3067 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.73 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.85 (2)	2.11 (2)	2.948 (2)	176 (2)
C3—H3⋯O2ⁱⁱ	0.93	2.40	3.264 (2)	154 (1)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, y-1, z.

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/S1600536811040189/bq2307sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811040189/bq2307Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811040189/bq2307Isup3.cml

checkCIF report

Comment top

The sulfonamide moiety is present in several biologically important compounds. The hydrogen bonding preferences of sulfonamides have also been investigated (Adsmond & Grant, 2001). As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2003), N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-(aryl)-arylsulfonamides (Gowda & Kumar, 2003; Rodrigues et al., 2011), in the present work, the crystal structure of 2,4-dichloro-N-(3,5-dimethylphenyl)- benzenesulfonamide (I) has been determined (Fig. 1).

In (I), the N—H bond in the C—SO₂—NH—C segment is syn to one of the meta-methyl groups in the aniline benzene ring and anti to the other. Further, the conformations of the N—C bonds in the C—SO₂—NH—C segment have gauche torsions with respect to the S═O bonds.

The molecule is bent at the S atom with C—SO₂—NH—C torsion angle of 54.94 (20)°, compared to the value of -60.84 (18)° in 2,4-dichloro-N-(3,4-dimethylphenyl)-benzenesulfonamide (II) (Rodrigues et al., 2011).

The sulfonyl and the aniline benzene rings are tilted relative to each other by 66.4 (1)°, compared to the value of 82.8 (1)° in (II)

The other bond parameters in (I) are similar to those observed in (II) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

In the crystal structure, the pairs of intermolecular N–H···O hydrogen bonds (Table 1) link the molecules into inversion-related dimers. There is also weak C-H···O hydrogen bonds between these dimers. Part of the crystal structure is shown in Fig. 2.

Related literature top

For the preparation of the title compound, see: Savitha & Gowda (2006). For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2003), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and on N-(aryl)-arylsulfonamides, see: Gelbrich et al. (2007); Perlovich et al. (2006); Gowda & Kumar (2003); Rodrigues et al. (2011).

Experimental top

The solution of 1,3-dichlorobenzene (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 0° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 2,4-dichlorobenzenesulfonylchloride was treated with 3,5-dimethylaniline in the stoichiometric ratio and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid 2,4-dichloro-N- (3,5-dimethylphenyl)-benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by recording its infrared and NMR spectra (Savitha & Gowda, 2006).

Prism like light pink single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation 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 labeling scheme and displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

2,4-Dichloro-N-(3,5-dimethylphenyl)benzenesulfonamide top

Crystal data top

C₁₄H₁₃Cl₂NO₂S	F(000) = 1360
M_r = 330.21	D_x = 1.459 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3755 reflections
a = 23.067 (2) Å	θ = 2.7–28.0°
b = 8.0794 (5) Å	µ = 0.57 mm⁻¹
c = 16.470 (1) Å	T = 293 K
β = 101.575 (7)°	Prism, light pink
V = 3007.0 (4) Å³	0.50 × 0.46 × 0.42 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD Detector	3067 independent reflections
Radiation source: fine-focus sealed tube	2555 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −26→28
T_min = 0.764, T_max = 0.796	k = −10→10
10045 measured reflections	l = −20→10

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.080P)² + 1.2587P] where P = (F_o² + 2F_c²)/3
3067 reflections	(Δ/σ)_max = 0.005
186 parameters	Δρ_max = 0.42 e Å⁻³
1 restraint	Δρ_min = −0.73 e Å⁻³

Crystal data top

C₁₄H₁₃Cl₂NO₂S	V = 3007.0 (4) Å³
M_r = 330.21	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.067 (2) Å	µ = 0.57 mm⁻¹
b = 8.0794 (5) Å	T = 293 K
c = 16.470 (1) Å	0.50 × 0.46 × 0.42 mm
β = 101.575 (7)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD Detector	3067 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2555 reflections with I > 2σ(I)
T_min = 0.764, T_max = 0.796	R_int = 0.018
10045 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	1 restraint
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.42 e Å⁻³
3067 reflections	Δρ_min = −0.73 e Å⁻³
186 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	0.46825 (3)	0.17165 (7)	0.04412 (4)	0.0546 (2)
Cl2	0.40676 (4)	−0.06394 (9)	0.31762 (4)	0.0740 (3)
S1	0.44325 (2)	0.54969 (6)	0.10219 (3)	0.03642 (17)
O1	0.50536 (6)	0.55754 (19)	0.10210 (9)	0.0465 (4)
O2	0.41625 (8)	0.68220 (18)	0.13769 (11)	0.0528 (4)
N1	0.41157 (8)	0.5283 (2)	0.00604 (11)	0.0404 (4)
H1N	0.4355 (10)	0.498 (3)	−0.0239 (14)	0.048*
C1	0.42987 (8)	0.3693 (2)	0.15700 (11)	0.0324 (4)
C2	0.44187 (8)	0.2097 (2)	0.13350 (12)	0.0343 (4)
C3	0.43374 (9)	0.0751 (2)	0.18203 (13)	0.0402 (5)
H3	0.4412	−0.0318	0.1659	0.048*
C4	0.41432 (9)	0.1028 (3)	0.25492 (12)	0.0423 (5)
C5	0.40168 (10)	0.2587 (3)	0.27941 (13)	0.0453 (5)
H5	0.3883	0.2746	0.3285	0.054*
C6	0.40921 (9)	0.3917 (3)	0.22994 (12)	0.0406 (4)
H6	0.4003	0.4978	0.2456	0.049*
C7	0.35076 (9)	0.4915 (2)	−0.02514 (12)	0.0383 (4)
C8	0.33728 (10)	0.4228 (3)	−0.10365 (14)	0.0437 (5)
H8	0.3675	0.3984	−0.1315	0.052*
C9	0.27908 (11)	0.3901 (3)	−0.14115 (16)	0.0556 (6)
C10	0.23500 (11)	0.4246 (3)	−0.09667 (18)	0.0612 (7)
H10	0.1958	0.4018	−0.1208	0.073*
C11	0.24769 (10)	0.4914 (3)	−0.01807 (16)	0.0539 (6)
C12	0.30625 (10)	0.5275 (3)	0.01805 (14)	0.0471 (5)
H12	0.3155	0.5750	0.0705	0.057*
C13	0.26428 (15)	0.3176 (5)	−0.2271 (2)	0.0863 (10)
H13A	0.2571	0.2010	−0.2235	0.104*
H13B	0.2968	0.3349	−0.2544	0.104*
H13C	0.2295	0.3706	−0.2580	0.104*
C14	0.19926 (13)	0.5276 (4)	0.0292 (2)	0.0767 (9)
H14A	0.1899	0.4286	0.0560	0.092*
H14B	0.1646	0.5660	−0.0086	0.092*
H14C	0.2125	0.6114	0.0700	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0766 (4)	0.0469 (3)	0.0478 (3)	0.0090 (3)	0.0306 (3)	−0.0059 (2)
Cl2	0.1009 (6)	0.0607 (4)	0.0620 (4)	−0.0197 (4)	0.0203 (4)	0.0207 (3)
S1	0.0393 (3)	0.0314 (3)	0.0382 (3)	−0.00622 (18)	0.0070 (2)	−0.00107 (18)
O1	0.0392 (8)	0.0546 (9)	0.0446 (8)	−0.0151 (6)	0.0059 (6)	0.0006 (7)
O2	0.0694 (11)	0.0308 (7)	0.0597 (10)	−0.0001 (7)	0.0167 (8)	−0.0068 (6)
N1	0.0357 (9)	0.0483 (10)	0.0374 (9)	−0.0037 (7)	0.0081 (7)	0.0039 (7)
C1	0.0316 (9)	0.0322 (9)	0.0332 (9)	−0.0036 (7)	0.0063 (7)	−0.0024 (7)
C2	0.0337 (9)	0.0357 (10)	0.0341 (9)	−0.0014 (8)	0.0082 (7)	−0.0040 (7)
C3	0.0422 (11)	0.0324 (10)	0.0451 (11)	−0.0033 (8)	0.0062 (9)	−0.0012 (8)
C4	0.0411 (11)	0.0447 (11)	0.0393 (10)	−0.0114 (9)	0.0035 (8)	0.0077 (9)
C5	0.0492 (12)	0.0544 (13)	0.0344 (10)	−0.0061 (10)	0.0134 (9)	−0.0029 (9)
C6	0.0444 (11)	0.0406 (11)	0.0383 (10)	−0.0020 (9)	0.0123 (8)	−0.0064 (8)
C7	0.0369 (10)	0.0346 (10)	0.0422 (10)	−0.0004 (8)	0.0049 (8)	0.0104 (8)
C8	0.0419 (11)	0.0406 (11)	0.0467 (12)	0.0004 (9)	0.0044 (9)	0.0049 (9)
C9	0.0465 (13)	0.0568 (14)	0.0572 (14)	−0.0022 (11)	−0.0044 (10)	0.0029 (11)
C10	0.0358 (12)	0.0689 (17)	0.0728 (17)	−0.0036 (11)	−0.0036 (11)	0.0097 (13)
C11	0.0374 (11)	0.0594 (14)	0.0655 (16)	0.0035 (10)	0.0117 (10)	0.0199 (12)
C12	0.0429 (12)	0.0516 (13)	0.0471 (12)	0.0007 (9)	0.0097 (9)	0.0080 (10)
C13	0.0644 (18)	0.106 (3)	0.077 (2)	−0.0030 (17)	−0.0139 (15)	−0.0246 (18)
C14	0.0469 (15)	0.100 (2)	0.087 (2)	0.0041 (14)	0.0234 (14)	0.0196 (18)

Geometric parameters (Å, º) top

Cl1—C2	1.7296 (19)	C7—C8	1.384 (3)
Cl2—C4	1.727 (2)	C7—C12	1.392 (3)
S1—O2	1.4220 (16)	C8—C9	1.386 (3)
S1—O1	1.4343 (16)	C8—H8	0.9300
S1—N1	1.6148 (18)	C9—C10	1.395 (4)
S1—C1	1.7739 (19)	C9—C13	1.506 (4)
N1—C7	1.425 (3)	C10—C11	1.379 (4)
N1—H1N	0.845 (16)	C10—H10	0.9300
C1—C2	1.390 (3)	C11—C12	1.393 (3)
C1—C6	1.390 (3)	C11—C14	1.512 (4)
C2—C3	1.385 (3)	C12—H12	0.9300
C3—C4	1.381 (3)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.372 (3)	C13—H13C	0.9600
C5—C6	1.380 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600

O2—S1—O1	119.16 (10)	C12—C7—N1	123.1 (2)
O2—S1—N1	109.55 (10)	C7—C8—C9	120.6 (2)
O1—S1—N1	105.02 (9)	C7—C8—H8	119.7
O2—S1—C1	105.91 (9)	C9—C8—H8	119.7
O1—S1—C1	108.22 (9)	C8—C9—C10	118.1 (2)
N1—S1—C1	108.67 (9)	C8—C9—C13	120.6 (2)
C7—N1—S1	126.50 (14)	C10—C9—C13	121.3 (2)
C7—N1—H1N	116.2 (17)	C11—C10—C9	122.1 (2)
S1—N1—H1N	112.5 (17)	C11—C10—H10	118.9
C2—C1—C6	118.90 (17)	C9—C10—H10	118.9
C2—C1—S1	123.77 (14)	C10—C11—C12	119.2 (2)
C6—C1—S1	117.23 (15)	C10—C11—C14	121.3 (2)
C3—C2—C1	120.70 (17)	C12—C11—C14	119.5 (3)
C3—C2—Cl1	117.57 (15)	C7—C12—C11	119.3 (2)
C1—C2—Cl1	121.72 (15)	C7—C12—H12	120.3
C4—C3—C2	118.62 (19)	C11—C12—H12	120.3
C4—C3—H3	120.7	C9—C13—H13A	109.5
C2—C3—H3	120.7	C9—C13—H13B	109.5
C5—C4—C3	121.99 (18)	H13A—C13—H13B	109.5
C5—C4—Cl2	119.18 (16)	C9—C13—H13C	109.5
C3—C4—Cl2	118.83 (17)	H13A—C13—H13C	109.5
C4—C5—C6	118.80 (19)	H13B—C13—H13C	109.5
C4—C5—H5	120.6	C11—C14—H14A	109.5
C6—C5—H5	120.6	C11—C14—H14B	109.5
C5—C6—C1	120.96 (19)	H14A—C14—H14B	109.5
C5—C6—H6	119.5	C11—C14—H14C	109.5
C1—C6—H6	119.5	H14A—C14—H14C	109.5
C8—C7—C12	120.7 (2)	H14B—C14—H14C	109.5
C8—C7—N1	116.14 (18)

O2—S1—N1—C7	−60.3 (2)	Cl2—C4—C5—C6	178.44 (17)
O1—S1—N1—C7	170.56 (17)	C4—C5—C6—C1	−0.7 (3)
C1—S1—N1—C7	54.9 (2)	C2—C1—C6—C5	1.2 (3)
O2—S1—C1—C2	170.58 (16)	S1—C1—C6—C5	−175.34 (16)
O1—S1—C1—C2	−60.58 (18)	S1—N1—C7—C8	−158.16 (16)
N1—S1—C1—C2	52.96 (18)	S1—N1—C7—C12	24.4 (3)
O2—S1—C1—C6	−13.03 (18)	C12—C7—C8—C9	0.7 (3)
O1—S1—C1—C6	115.81 (16)	N1—C7—C8—C9	−176.8 (2)
N1—S1—C1—C6	−130.65 (16)	C7—C8—C9—C10	−1.5 (3)
C6—C1—C2—C3	−0.4 (3)	C7—C8—C9—C13	179.1 (3)
S1—C1—C2—C3	175.98 (15)	C8—C9—C10—C11	0.9 (4)
C6—C1—C2—Cl1	−179.47 (15)	C13—C9—C10—C11	−179.8 (3)
S1—C1—C2—Cl1	−3.1 (2)	C9—C10—C11—C12	0.7 (4)
C1—C2—C3—C4	−1.0 (3)	C9—C10—C11—C14	−179.9 (3)
Cl1—C2—C3—C4	178.18 (16)	C8—C7—C12—C11	0.9 (3)
C2—C3—C4—C5	1.5 (3)	N1—C7—C12—C11	178.2 (2)
C2—C3—C4—Cl2	−177.60 (15)	C10—C11—C12—C7	−1.5 (3)
C3—C4—C5—C6	−0.6 (3)	C14—C11—C12—C7	179.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.85 (2)	2.11 (2)	2.948 (2)	176 (2)
C3—H3···O2ⁱⁱ	0.93	2.40	3.264 (2)	154 (1)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃Cl₂NO₂S
M_r	330.21
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	23.067 (2), 8.0794 (5), 16.470 (1)
β (°)	101.575 (7)
V (Å³)	3007.0 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.57
Crystal size (mm)	0.50 × 0.46 × 0.42

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	0.764, 0.796
No. of measured, independent and observed [I > 2σ(I)] reflections	10045, 3067, 2555
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.124, 1.09
No. of reflections	3067
No. of parameters	186
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.73

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
N1—H1N···O1ⁱ	0.845 (16)	2.105 (17)	2.948 (2)	176 (2)
C3—H3···O2ⁱⁱ	0.93	2.40	3.264 (2)	154 (1)

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

Acknowledgements

VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS fellowship.

References

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