4-Chloro-N-(2,6-dimethyl­phen­yl)-2-methyl­benzene­sulfonamide

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

doi:10.1107/S1600536811040888

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2890

doi:10.1107/S1600536811040888

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4-Chloro-N-(2,6-dimethylphenyl)-2-methylbenzenesulfonamide

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 3 October 2011; accepted 4 October 2011; online 8 October 2011)

In the title compound, C₁₅H₁₆ClNO₂S, the C—SO₂—NH—C torsion angle is −61.15 (16)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 38.8 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ). For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001 ). For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2000 ), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ), on N-(aryl)-arylsulfonamides, see: Gelbrich et al. (2007 ); Perlovich et al. (2006 ); Rodrigues et al. (2011 ); Shetty & Gowda (2005 ) and on N-(chloro)-arylsulfonamides, see: Gowda et al. (2003 ).

Experimental

Crystal data

C₁₅H₁₆ClNO₂S
M_r = 309.80
Triclinic, $[P \overline 1]$
a = 8.275 (2) Å
b = 8.430 (2) Å
c = 11.195 (2) Å
α = 92.12 (1)°
β = 96.15 (1)°
γ = 109.58 (2)°
V = 729.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 293 K
0.46 × 0.40 × 0.24 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 = 0.836, T_max = 0.909
4886 measured reflections
2948 independent reflections
2588 reflections with I > 2σ(I)
R_int = 0.011

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.096
S = 1.06
2948 reflections
187 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.84 (2)	2.21 (2)	3.024 (2)	165 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

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/S1600536811040888/bt5663sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811040888/bt5663Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811040888/bt5663Isup3.cml

checkCIF report

Comment top

The amide and sulfonamide moieties are the constituents of many biologically significant compounds. The hydrogen bonding preferences of sulfonamides have 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., 2000), N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-(aryl)-arylsulfonamides (Rodrigues et al., 2011; Shetty & Gowda, 2005) and N-(chloro)-arylsulfonamides (Gowda et al., 2003), in the present work, the crystal structure of 4-Chloro-2-methyl-N-(2,6-dimethylphenyl)benzenesulfonamide (I) has been determined (Fig. 1).

In (I), the conformation of the N—C bond in the C—SO₂—NH—C segment has gauche torsions with respect to the S═O bonds. The molecule is bent at the S atom with the C—SO₂—NH—C torsion angle of -61.2 (2)°, compared to the value of 67.5 (2)° in 4-Chloro-2-methyl-N-(2,4-dimethylphenyl)benzenesulfonamide (II) (Rodrigues et al., 2011).

The sulfonyl and the aniline benzene rings are tilted relative to each other by 38.8 (1)°, compared to the value of 44.5 (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, the intermolecular N–H···O hydrogen bonds (Table 1) link the molecules into dimeric chains. 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 studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2000), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007), on N-(aryl)-arylsulfonamides, see: Gelbrich et al. (2007); Perlovich et al. (2006); Rodrigues et al. (2011); Shetty & Gowda (2005) and on N-(chloro)-arylsulfonamides, see: Gowda et al. (2003).

Experimental top

The solution of m-chlorotoluene (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-methyl-4-chlorobenzenesulfonylchloride was treated with 2,6-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 cc). The resultant solid 4-chloro-2-methyl-N- (2,6-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).

Rod like colourless 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 labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

4-Chloro-N-(2,6-dimethylphenyl)-2-methylbenzenesulfonamide top

Crystal data top

C₁₅H₁₆ClNO₂S	Z = 2
M_r = 309.80	F(000) = 324
Triclinic, P1	D_x = 1.411 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.275 (2) Å	Cell parameters from 2916 reflections
b = 8.430 (2) Å	θ = 2.6–27.8°
c = 11.195 (2) Å	µ = 0.41 mm⁻¹
α = 92.12 (1)°	T = 293 K
β = 96.15 (1)°	Rod, colourless
γ = 109.58 (2)°	0.46 × 0.40 × 0.24 mm
V = 729.3 (3) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2948 independent reflections
Radiation source: fine-focus sealed tube	2588 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.011
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→10
T_min = 0.836, T_max = 0.909	k = −10→10
4886 measured reflections	l = −13→11

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0348P)² + 0.4969P] where P = (F_o² + 2F_c²)/3
2948 reflections	(Δ/σ)_max < 0.001
187 parameters	Δρ_max = 0.31 e Å⁻³
1 restraint	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₁₅H₁₆ClNO₂S	γ = 109.58 (2)°
M_r = 309.80	V = 729.3 (3) Å³
Triclinic, P1	Z = 2
a = 8.275 (2) Å	Mo Kα radiation
b = 8.430 (2) Å	µ = 0.41 mm⁻¹
c = 11.195 (2) Å	T = 293 K
α = 92.12 (1)°	0.46 × 0.40 × 0.24 mm
β = 96.15 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2948 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2588 reflections with I > 2σ(I)
T_min = 0.836, T_max = 0.909	R_int = 0.011
4886 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.31 e Å⁻³
2948 reflections	Δρ_min = −0.45 e Å⁻³
187 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
C1	0.3930 (2)	0.4028 (2)	0.21423 (16)	0.0332 (4)
C2	0.2952 (3)	0.3124 (2)	0.10740 (17)	0.0394 (4)
C3	0.3843 (3)	0.2532 (3)	0.02725 (18)	0.0467 (5)
H3	0.3235	0.1908	−0.0436	0.056*
C4	0.5591 (3)	0.2846 (3)	0.05010 (19)	0.0462 (5)
C5	0.6547 (3)	0.3732 (3)	0.1545 (2)	0.0462 (5)
H5	0.7730	0.3938	0.1694	0.055*
C6	0.5698 (2)	0.4307 (2)	0.23665 (18)	0.0395 (4)
H6	0.6318	0.4892	0.3084	0.047*
C7	0.1102 (2)	0.1667 (2)	0.37777 (15)	0.0314 (4)
C8	0.1613 (3)	0.0322 (2)	0.34000 (17)	0.0379 (4)
C9	0.0315 (3)	−0.1166 (3)	0.29221 (19)	0.0507 (6)
H9	0.0613	−0.2074	0.2649	0.061*
C10	−0.1402 (3)	−0.1317 (3)	0.2847 (2)	0.0569 (6)
H10	−0.2246	−0.2313	0.2505	0.068*
C11	−0.1880 (3)	−0.0012 (3)	0.3271 (2)	0.0514 (5)
H11	−0.3047	−0.0142	0.3226	0.062*
C12	−0.0641 (2)	0.1505 (2)	0.37689 (17)	0.0379 (4)
C13	0.1034 (3)	0.2753 (3)	0.0727 (2)	0.0559 (6)
H13A	0.0824	0.3789	0.0591	0.067*
H13B	0.0416	0.2222	0.1365	0.067*
H13C	0.0646	0.2012	0.0003	0.067*
C14	0.3469 (3)	0.0408 (3)	0.3529 (2)	0.0521 (5)
H14A	0.4067	0.1047	0.4268	0.063*
H14B	0.4007	0.0947	0.2862	0.063*
H14C	0.3516	−0.0714	0.3537	0.063*
C15	−0.1197 (3)	0.2859 (3)	0.4316 (2)	0.0492 (5)
H15A	−0.0981	0.3784	0.3810	0.059*
H15B	−0.0556	0.3249	0.5100	0.059*
H15C	−0.2410	0.2411	0.4387	0.059*
N1	0.2397 (2)	0.32745 (19)	0.42256 (14)	0.0335 (3)
H1N	0.325 (2)	0.324 (3)	0.4680 (18)	0.040*
O1	0.15174 (18)	0.51087 (17)	0.27909 (13)	0.0433 (3)
O2	0.43786 (18)	0.61202 (16)	0.40162 (13)	0.0448 (3)
Cl1	0.66049 (10)	0.20864 (10)	−0.05578 (6)	0.0746 (2)
S1	0.30108 (6)	0.47803 (5)	0.33118 (4)	0.03365 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0364 (9)	0.0281 (8)	0.0340 (9)	0.0096 (7)	0.0053 (7)	0.0015 (7)
C2	0.0418 (10)	0.0407 (10)	0.0341 (9)	0.0137 (8)	0.0006 (8)	0.0003 (8)
C3	0.0544 (13)	0.0512 (12)	0.0328 (10)	0.0182 (10)	0.0011 (9)	−0.0046 (9)
C4	0.0542 (12)	0.0479 (12)	0.0431 (11)	0.0229 (10)	0.0158 (9)	0.0044 (9)
C5	0.0382 (10)	0.0510 (12)	0.0497 (12)	0.0144 (9)	0.0093 (9)	0.0044 (9)
C6	0.0368 (10)	0.0360 (10)	0.0409 (10)	0.0071 (8)	0.0033 (8)	0.0000 (8)
C7	0.0365 (9)	0.0287 (9)	0.0253 (8)	0.0075 (7)	0.0003 (7)	−0.0003 (7)
C8	0.0501 (11)	0.0325 (9)	0.0313 (9)	0.0153 (8)	0.0030 (8)	0.0012 (7)
C9	0.0784 (16)	0.0300 (10)	0.0391 (11)	0.0152 (10)	0.0001 (10)	−0.0039 (8)
C10	0.0656 (15)	0.0368 (11)	0.0463 (12)	−0.0050 (10)	−0.0112 (11)	−0.0026 (9)
C11	0.0385 (11)	0.0539 (13)	0.0487 (12)	0.0010 (10)	−0.0030 (9)	0.0077 (10)
C12	0.0375 (10)	0.0398 (10)	0.0335 (9)	0.0096 (8)	0.0027 (8)	0.0055 (8)
C13	0.0439 (12)	0.0775 (16)	0.0412 (12)	0.0199 (11)	−0.0082 (9)	−0.0126 (11)
C14	0.0612 (14)	0.0455 (12)	0.0589 (14)	0.0290 (11)	0.0115 (11)	0.0042 (10)
C15	0.0445 (11)	0.0550 (13)	0.0540 (13)	0.0222 (10)	0.0133 (10)	0.0075 (10)
N1	0.0342 (8)	0.0305 (8)	0.0313 (8)	0.0078 (6)	−0.0030 (6)	−0.0029 (6)
O1	0.0454 (8)	0.0411 (8)	0.0487 (8)	0.0216 (6)	0.0057 (6)	0.0036 (6)
O2	0.0474 (8)	0.0298 (7)	0.0486 (8)	0.0042 (6)	0.0020 (6)	−0.0089 (6)
Cl1	0.0795 (5)	0.0927 (5)	0.0632 (4)	0.0401 (4)	0.0278 (3)	−0.0078 (4)
S1	0.0362 (2)	0.0266 (2)	0.0361 (2)	0.00905 (18)	0.00272 (18)	−0.00301 (17)

Geometric parameters (Å, º) top

C1—C6	1.394 (3)	C10—C11	1.374 (4)
C1—C2	1.406 (3)	C10—H10	0.9300
C1—S1	1.7805 (19)	C11—C12	1.394 (3)
C2—C3	1.397 (3)	C11—H11	0.9300
C2—C13	1.515 (3)	C12—C15	1.500 (3)
C3—C4	1.374 (3)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.375 (3)	C13—H13C	0.9600
C4—Cl1	1.742 (2)	C14—H14A	0.9600
C5—C6	1.381 (3)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—H6	0.9300	C15—H15A	0.9600
C7—C12	1.401 (3)	C15—H15B	0.9600
C7—C8	1.403 (3)	C15—H15C	0.9600
C7—N1	1.448 (2)	N1—S1	1.6405 (16)
C8—C9	1.392 (3)	N1—H1N	0.835 (15)
C8—C14	1.503 (3)	O1—S1	1.4250 (14)
C9—C10	1.377 (4)	O2—S1	1.4369 (14)
C9—H9	0.9300

C6—C1—C2	120.62 (17)	C12—C11—H11	119.6
C6—C1—S1	115.99 (14)	C11—C12—C7	117.58 (19)
C2—C1—S1	123.31 (14)	C11—C12—C15	119.85 (19)
C3—C2—C1	116.59 (18)	C7—C12—C15	122.52 (18)
C3—C2—C13	117.95 (18)	C2—C13—H13A	109.5
C1—C2—C13	125.46 (18)	C2—C13—H13B	109.5
C4—C3—C2	121.87 (19)	H13A—C13—H13B	109.5
C4—C3—H3	119.1	C2—C13—H13C	109.5
C2—C3—H3	119.1	H13A—C13—H13C	109.5
C3—C4—C5	121.49 (19)	H13B—C13—H13C	109.5
C3—C4—Cl1	118.87 (17)	C8—C14—H14A	109.5
C5—C4—Cl1	119.64 (17)	C8—C14—H14B	109.5
C4—C5—C6	118.02 (19)	H14A—C14—H14B	109.5
C4—C5—H5	121.0	C8—C14—H14C	109.5
C6—C5—H5	121.0	H14A—C14—H14C	109.5
C5—C6—C1	121.38 (19)	H14B—C14—H14C	109.5
C5—C6—H6	119.3	C12—C15—H15A	109.5
C1—C6—H6	119.3	C12—C15—H15B	109.5
C12—C7—C8	122.19 (17)	H15A—C15—H15B	109.5
C12—C7—N1	117.89 (16)	C12—C15—H15C	109.5
C8—C7—N1	119.90 (16)	H15A—C15—H15C	109.5
C9—C8—C7	117.36 (19)	H15B—C15—H15C	109.5
C9—C8—C14	119.58 (19)	C7—N1—S1	119.87 (12)
C7—C8—C14	123.02 (17)	C7—N1—H1N	116.8 (15)
C10—C9—C8	121.1 (2)	S1—N1—H1N	109.8 (15)
C10—C9—H9	119.4	O1—S1—O2	118.97 (9)
C8—C9—H9	119.4	O1—S1—N1	108.26 (9)
C11—C10—C9	120.7 (2)	O2—S1—N1	105.13 (8)
C11—C10—H10	119.7	O1—S1—C1	108.66 (9)
C9—C10—H10	119.7	O2—S1—C1	107.46 (9)
C10—C11—C12	120.9 (2)	N1—S1—C1	107.89 (8)
C10—C11—H11	119.6

C6—C1—C2—C3	0.2 (3)	C8—C9—C10—C11	−1.7 (3)
S1—C1—C2—C3	−176.35 (15)	C9—C10—C11—C12	1.1 (3)
C6—C1—C2—C13	−179.5 (2)	C10—C11—C12—C7	2.3 (3)
S1—C1—C2—C13	3.9 (3)	C10—C11—C12—C15	−175.1 (2)
C1—C2—C3—C4	−1.4 (3)	C8—C7—C12—C11	−5.4 (3)
C13—C2—C3—C4	178.4 (2)	N1—C7—C12—C11	176.31 (16)
C2—C3—C4—C5	1.3 (3)	C8—C7—C12—C15	171.99 (18)
C2—C3—C4—Cl1	−179.08 (17)	N1—C7—C12—C15	−6.3 (3)
C3—C4—C5—C6	−0.1 (3)	C12—C7—N1—S1	−86.30 (19)
Cl1—C4—C5—C6	−179.66 (16)	C8—C7—N1—S1	95.34 (18)
C4—C5—C6—C1	−1.1 (3)	C7—N1—S1—O1	56.27 (16)
C2—C1—C6—C5	1.0 (3)	C7—N1—S1—O2	−175.60 (13)
S1—C1—C6—C5	177.81 (16)	C7—N1—S1—C1	−61.15 (16)
C12—C7—C8—C9	4.8 (3)	C6—C1—S1—O1	154.04 (14)
N1—C7—C8—C9	−176.88 (16)	C2—C1—S1—O1	−29.23 (18)
C12—C7—C8—C14	−173.08 (18)	C6—C1—S1—O2	24.10 (17)
N1—C7—C8—C14	5.2 (3)	C2—C1—S1—O2	−159.17 (16)
C7—C8—C9—C10	−1.2 (3)	C6—C1—S1—N1	−88.80 (15)
C14—C8—C9—C10	176.7 (2)	C2—C1—S1—N1	87.93 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.84 (2)	2.21 (2)	3.024 (2)	165 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆ClNO₂S
M_r	309.80
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.275 (2), 8.430 (2), 11.195 (2)
α, β, γ (°)	92.12 (1), 96.15 (1), 109.58 (2)
V (Å³)	729.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.46 × 0.40 × 0.24

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	0.836, 0.909
No. of measured, independent and observed [I > 2σ(I)] reflections	4886, 2948, 2588
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.096, 1.06
No. of reflections	2948
No. of parameters	187
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)	0.31, −0.45

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···O2ⁱ	0.835 (15)	2.210 (16)	3.024 (2)	165 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

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

References

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