N-(2,4-Dimethyl­phen­yl)-2,4-dimethyl­benzene­sulfonamide

Nirmala, P.G.; Gowda, B.T.; Foro, S.; Fuess, H.

doi:10.1107/S1600536810012663

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1059

https://doi.org/10.1107/S1600536810012663

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N-(2,4-Dimethylphenyl)-2,4-dimethylbenzenesulfonamide

P. G. Nirmala,^a B. Thimme Gowda,^a ^* Sabine Foro ^b 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 2 April 2010; accepted 5 April 2010; online 14 April 2010)

In the crystal structure of the title compound, C₁₆H₁₉NO₂S, the molecule is bent at the S atom with a C—SO₂—NH—C torsion angle of 66.5 (2)°. The dihedral angle between the sulfonyl and aniline benzene rings in the molecule is 41.0 (1)°. The crystal structure features inversion dimers linked by pairs of N—H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ). For our studies of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009a ,b ); Nirmala et al. (2010 ). For related structures, see: Gelbrich et al. (2007 ); Perlovich et al. (2006 ).

Experimental

Crystal data

C₁₆H₁₉NO₂S
M_r = 289.38
Triclinic, $[P \overline 1]$
a = 8.225 (1) Å
b = 8.423 (1) Å
c = 10.992 (2) Å
α = 85.58 (2)°
β = 88.97 (2)°
γ = 84.43 (1)°
V = 755.62 (19) Å³
Z = 2
Cu Kα radiation
μ = 1.91 mm⁻¹
T = 299 K
0.40 × 0.38 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.516, T_max = 0.647
2899 measured reflections
2689 independent reflections
2419 reflections with I > 2σ(I)
R_int = 0.026
3 standard reflections every 120 min intensity decay: 1.5%

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.282
S = 1.36
2689 reflections
188 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.87 (2)	2.19 (2)	3.024 (4)	161 (3)
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ); 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: https://doi.org/10.1107/S1600536810012663/bq2205sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810012663/bq2205Isup2.hkl

checkCIF report

Comment top

In the present work, as part of a study of substituent effects on the structures of N-(aryl)arylsulfonamides (Gowda et al., 2009a,b; Nirmala et al., 2010), the structure of 2,4-dimethyl-N-(2,4-dimethylphenyl)benzenesulfonamide (I) has been determined (Fig. 1). The molecule in (I) is bent at the S atom with the C—SO₂—NH—C torsion angle of 66.5 (2)°, compared to the values of 70.1 (2) and -66.0 (2)° in the two independent molecules of 2,4-dimethyl-N-(2,3-dimethylphenyl)benzenesulfonamide (II) (Nirmala et al., 2010), 53.9 (2)° in 2,4-dimethyl-N-(3,5-dimethylphenyl)benzenesulfonamide (III) (Gowda et al., 2009b) and 46.1 (3)° (glide image of molecule 1) and 47.7 (3)° (molecule 2) in the two independent molecules of 2,4-dimethyl-N-(phenyl)benzenesulfonamide (IV)(Gowda et al., 2009a).

The sulfonyl and the anilino benzene rings in (I) are tilted relative to each other by 41.0 (1)°, compared to the values of 41.5 (1) and 43.8 (1)° in the two molecules of (II), 82.1 (1)° in (III) and 67.5 (1)° (molecule 1) and 72.9 (1)° (molecule 2) in (IV),

The remaining bond parameters in (I) are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The crystal packing of molecules in (I) through pairs of N—H···O(S) hydrogen bonds (Table 1) is shown in Fig. 2.

Related literature top

For the preparation of the title compound, see: Savitha & Gowda (2006). For our studies of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009a,b); Nirmala et al. (2010). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

Experimental top

The solution of m-xylene (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-dimethylbenzenesulfonylchloride was treated with 2,4-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-dimethyl-N-(2,4-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 brown single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Structure description top

For the preparation of the title compound, see: Savitha & Gowda (2006). For our studies of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009a,b); Nirmala et al. (2010). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); 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 (I), 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.

N-(2,4-Dimethylphenyl)-2,4-dimethylbenzenesulfonamide top

Crystal data top

C₁₆H₁₉NO₂S	Z = 2
M_r = 289.38	F(000) = 308
Triclinic, P1	D_x = 1.272 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 8.225 (1) Å	Cell parameters from 25 reflections
b = 8.423 (1) Å	θ = 7.8–18.8°
c = 10.992 (2) Å	µ = 1.91 mm⁻¹
α = 85.58 (2)°	T = 299 K
β = 88.97 (2)°	Prism, brown
γ = 84.43 (1)°	0.40 × 0.38 × 0.25 mm
V = 755.62 (19) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	2419 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 67.1°, θ_min = 4.0°
ω/2θ scans	h = −9→9
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
T_min = 0.516, T_max = 0.647	l = −13→1
2899 measured reflections	3 standard reflections every 120 min
2689 independent reflections	intensity decay: 1.5%

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.282	H atoms treated by a mixture of independent and constrained refinement
S = 1.36	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
2689 reflections	(Δ/σ)_max = 0.002
188 parameters	Δρ_max = 0.48 e Å⁻³
1 restraint	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₁₆H₁₉NO₂S	γ = 84.43 (1)°
M_r = 289.38	V = 755.62 (19) Å³
Triclinic, P1	Z = 2
a = 8.225 (1) Å	Cu Kα radiation
b = 8.423 (1) Å	µ = 1.91 mm⁻¹
c = 10.992 (2) Å	T = 299 K
α = 85.58 (2)°	0.40 × 0.38 × 0.25 mm
β = 88.97 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2419 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.026
T_min = 0.516, T_max = 0.647	3 standard reflections every 120 min
2899 measured reflections	intensity decay: 1.5%
2689 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	1 restraint
wR(F²) = 0.282	H atoms treated by a mixture of independent and constrained refinement
S = 1.36	Δρ_max = 0.48 e Å⁻³
2689 reflections	Δρ_min = −0.50 e Å⁻³
188 parameters

Special details top

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	0.4299 (4)	0.5647 (3)	0.7203 (3)	0.0402 (7)
C2	0.3552 (4)	0.6498 (4)	0.6195 (3)	0.0452 (8)
C3	0.4587 (5)	0.7247 (5)	0.5349 (3)	0.0558 (9)
H3	0.4125	0.7809	0.4658	0.067*
C4	0.6233 (5)	0.7190 (5)	0.5491 (3)	0.0544 (9)
C5	0.6937 (5)	0.6310 (5)	0.6489 (3)	0.0555 (9)
H5	0.8064	0.6230	0.6586	0.067*
C6	0.5975 (4)	0.5549 (4)	0.7343 (3)	0.0482 (8)
H6	0.6455	0.4965	0.8019	0.058*
C7	0.1553 (3)	0.7468 (3)	0.9002 (2)	0.0349 (7)
C8	0.2064 (4)	0.8968 (3)	0.8660 (3)	0.0376 (7)
C9	0.0873 (4)	1.0200 (4)	0.8323 (3)	0.0440 (7)
H9	0.1186	1.1217	0.8109	0.053*
C10	−0.0762 (4)	0.9960 (4)	0.8295 (3)	0.0466 (8)
C11	−0.1231 (4)	0.8477 (4)	0.8650 (3)	0.0507 (8)
H11	−0.2332	0.8310	0.8649	0.061*
C12	−0.0100 (4)	0.7242 (4)	0.9006 (3)	0.0462 (8)
H12	−0.0436	0.6243	0.9253	0.055*
C13	0.1763 (5)	0.6667 (6)	0.5928 (4)	0.0643 (10)
H13A	0.1163	0.7044	0.6623	0.077*
H13B	0.1430	0.5648	0.5755	0.077*
H13C	0.1549	0.7419	0.5235	0.077*
C14	0.7272 (7)	0.8078 (6)	0.4575 (4)	0.0820 (14)
H14A	0.6587	0.8646	0.3956	0.098*
H14B	0.8048	0.7329	0.4206	0.098*
H14C	0.7843	0.8823	0.4981	0.098*
C15	0.3816 (4)	0.9290 (4)	0.8660 (3)	0.0517 (9)
H15A	0.4333	0.8978	0.7913	0.062*
H15B	0.4356	0.8689	0.9339	0.062*
H15C	0.3887	1.0411	0.8725	0.062*
C16	−0.1989 (5)	1.1362 (5)	0.7893 (4)	0.0717 (12)
H16A	−0.1420	1.2219	0.7519	0.086*
H16B	−0.2595	1.1723	0.8591	0.086*
H16C	−0.2726	1.1029	0.7317	0.086*
N1	0.2700 (3)	0.6121 (3)	0.9369 (2)	0.0397 (7)
H1N	0.363 (3)	0.632 (4)	0.966 (3)	0.048*
O1	0.4329 (3)	0.3611 (3)	0.9106 (2)	0.0548 (7)
O2	0.1751 (3)	0.4227 (3)	0.7989 (2)	0.0556 (7)
S1	0.32074 (8)	0.47490 (7)	0.84308 (6)	0.0403 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0449 (16)	0.0342 (15)	0.0406 (15)	0.0018 (12)	0.0016 (12)	−0.0038 (12)
C2	0.0482 (17)	0.0451 (17)	0.0413 (16)	0.0014 (13)	−0.0062 (13)	−0.0042 (13)
C3	0.068 (2)	0.059 (2)	0.0377 (16)	0.0034 (17)	−0.0005 (15)	0.0034 (14)
C4	0.059 (2)	0.059 (2)	0.0459 (17)	−0.0082 (16)	0.0117 (15)	−0.0051 (15)
C5	0.0485 (18)	0.063 (2)	0.055 (2)	−0.0048 (16)	0.0004 (15)	−0.0073 (17)
C6	0.0426 (16)	0.054 (2)	0.0461 (17)	0.0023 (13)	−0.0020 (13)	−0.0024 (14)
C7	0.0395 (14)	0.0278 (13)	0.0361 (14)	0.0007 (10)	−0.0008 (11)	0.0006 (10)
C8	0.0445 (16)	0.0305 (14)	0.0379 (14)	−0.0048 (11)	−0.0019 (11)	−0.0021 (11)
C9	0.0565 (18)	0.0344 (15)	0.0394 (15)	−0.0006 (13)	−0.0021 (13)	0.0030 (12)
C10	0.0490 (17)	0.0496 (18)	0.0382 (15)	0.0114 (14)	−0.0028 (13)	−0.0039 (13)
C11	0.0373 (15)	0.060 (2)	0.0546 (19)	−0.0009 (14)	0.0004 (13)	−0.0073 (15)
C12	0.0450 (17)	0.0396 (16)	0.0548 (18)	−0.0091 (13)	0.0068 (14)	−0.0035 (13)
C13	0.051 (2)	0.083 (3)	0.057 (2)	0.0006 (18)	−0.0143 (16)	0.0042 (19)
C14	0.093 (3)	0.085 (3)	0.068 (3)	−0.021 (3)	0.028 (2)	0.003 (2)
C15	0.0484 (18)	0.0418 (18)	0.066 (2)	−0.0129 (14)	−0.0079 (15)	0.0005 (15)
C16	0.066 (2)	0.071 (3)	0.069 (2)	0.027 (2)	−0.0035 (19)	0.011 (2)
N1	0.0447 (14)	0.0315 (13)	0.0412 (13)	0.0011 (11)	−0.0033 (10)	0.0035 (10)
O1	0.0646 (15)	0.0334 (12)	0.0617 (15)	0.0110 (11)	−0.0033 (12)	0.0080 (10)
O2	0.0544 (14)	0.0451 (13)	0.0700 (16)	−0.0142 (11)	−0.0020 (11)	−0.0086 (11)
S1	0.0460 (6)	0.0271 (6)	0.0469 (6)	−0.0010 (3)	−0.0018 (4)	0.0014 (3)

Geometric parameters (Å, º) top

C1—C6	1.384 (4)	C10—C16	1.520 (4)
C1—C2	1.391 (4)	C11—C12	1.365 (5)
C1—S1	1.769 (3)	C11—H11	0.9300
C2—C3	1.404 (5)	C12—H12	0.9300
C2—C13	1.497 (5)	C13—H13A	0.9600
C3—C4	1.362 (6)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.380 (5)	C14—H14A	0.9600
C4—C14	1.510 (5)	C14—H14B	0.9600
C5—C6	1.378 (5)	C14—H14C	0.9600
C5—H5	0.9300	C15—H15A	0.9600
C6—H6	0.9300	C15—H15B	0.9600
C7—C12	1.390 (4)	C15—H15C	0.9600
C7—C8	1.392 (4)	C16—H16A	0.9600
C7—N1	1.441 (3)	C16—H16B	0.9600
C8—C9	1.389 (4)	C16—H16C	0.9600
C8—C15	1.492 (4)	N1—S1	1.627 (3)
C9—C10	1.380 (5)	N1—H1N	0.869 (19)
C9—H9	0.9300	O1—S1	1.436 (2)
C10—C11	1.369 (5)	O2—S1	1.421 (3)

C6—C1—C2	121.0 (3)	C7—C12—H12	119.8
C6—C1—S1	115.3 (2)	C2—C13—H13A	109.5
C2—C1—S1	123.6 (2)	C2—C13—H13B	109.5
C1—C2—C3	116.4 (3)	H13A—C13—H13B	109.5
C1—C2—C13	126.0 (3)	C2—C13—H13C	109.5
C3—C2—C13	117.6 (3)	H13A—C13—H13C	109.5
C4—C3—C2	123.2 (3)	H13B—C13—H13C	109.5
C4—C3—H3	118.4	C4—C14—H14A	109.5
C2—C3—H3	118.4	C4—C14—H14B	109.5
C3—C4—C5	118.8 (3)	H14A—C14—H14B	109.5
C3—C4—C14	120.7 (4)	C4—C14—H14C	109.5
C5—C4—C14	120.5 (4)	H14A—C14—H14C	109.5
C6—C5—C4	120.2 (3)	H14B—C14—H14C	109.5
C6—C5—H5	119.9	C8—C15—H15A	109.5
C4—C5—H5	119.9	C8—C15—H15B	109.5
C5—C6—C1	120.4 (3)	H15A—C15—H15B	109.5
C5—C6—H6	119.8	C8—C15—H15C	109.5
C1—C6—H6	119.8	H15A—C15—H15C	109.5
C12—C7—C8	120.2 (3)	H15B—C15—H15C	109.5
C12—C7—N1	118.3 (3)	C10—C16—H16A	109.5
C8—C7—N1	121.5 (3)	C10—C16—H16B	109.5
C9—C8—C7	117.7 (3)	H16A—C16—H16B	109.5
C9—C8—C15	119.7 (3)	C10—C16—H16C	109.5
C7—C8—C15	122.6 (3)	H16A—C16—H16C	109.5
C10—C9—C8	122.0 (3)	H16B—C16—H16C	109.5
C10—C9—H9	119.0	C7—N1—S1	120.14 (19)
C8—C9—H9	119.0	C7—N1—H1N	118 (3)
C11—C10—C9	119.0 (3)	S1—N1—H1N	103 (2)
C11—C10—C16	122.1 (3)	O2—S1—O1	118.85 (15)
C9—C10—C16	118.9 (3)	O2—S1—N1	108.21 (14)
C12—C11—C10	120.7 (3)	O1—S1—N1	104.49 (13)
C12—C11—H11	119.6	O2—S1—C1	109.49 (15)
C10—C11—H11	119.6	O1—S1—C1	107.90 (14)
C11—C12—C7	120.4 (3)	N1—S1—C1	107.29 (13)
C11—C12—H12	119.8

C6—C1—C2—C3	−0.4 (5)	C8—C9—C10—C11	2.3 (5)
S1—C1—C2—C3	174.9 (2)	C8—C9—C10—C16	−178.9 (3)
C6—C1—C2—C13	178.8 (3)	C9—C10—C11—C12	−1.2 (5)
S1—C1—C2—C13	−5.9 (5)	C16—C10—C11—C12	−180.0 (3)
C1—C2—C3—C4	−1.1 (5)	C10—C11—C12—C7	−0.6 (5)
C13—C2—C3—C4	179.6 (4)	C8—C7—C12—C11	1.5 (5)
C2—C3—C4—C5	2.4 (6)	N1—C7—C12—C11	−179.1 (3)
C2—C3—C4—C14	−177.4 (3)	C12—C7—N1—S1	77.6 (3)
C3—C4—C5—C6	−2.1 (6)	C8—C7—N1—S1	−103.0 (3)
C14—C4—C5—C6	177.7 (4)	C7—N1—S1—O2	−51.5 (3)
C4—C5—C6—C1	0.6 (5)	C7—N1—S1—O1	−179.1 (2)
C2—C1—C6—C5	0.7 (5)	C7—N1—S1—C1	66.5 (2)
S1—C1—C6—C5	−175.0 (2)	C6—C1—S1—O2	−151.7 (3)
C12—C7—C8—C9	−0.4 (4)	C2—C1—S1—O2	32.7 (3)
N1—C7—C8—C9	−179.8 (2)	C6—C1—S1—O1	−21.0 (3)
C12—C7—C8—C15	178.9 (3)	C2—C1—S1—O1	163.4 (3)
N1—C7—C8—C15	−0.6 (4)	C6—C1—S1—N1	91.0 (3)
C7—C8—C9—C10	−1.5 (4)	C2—C1—S1—N1	−84.5 (3)
C15—C8—C9—C10	179.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.87 (2)	2.19 (2)	3.024 (4)	161 (3)

Symmetry code: (i) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉NO₂S
M_r	289.38
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	8.225 (1), 8.423 (1), 10.992 (2)
α, β, γ (°)	85.58 (2), 88.97 (2), 84.43 (1)
V (Å³)	755.62 (19)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	1.91
Crystal size (mm)	0.40 × 0.38 × 0.25

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.516, 0.647
No. of measured, independent and observed [I > 2σ(I)] reflections	2899, 2689, 2419
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.282, 1.36
No. of reflections	2689
No. of parameters	188
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)	0.48, −0.50

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), 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	0.869 (19)	2.19 (2)	3.024 (4)	161 (3)

Symmetry code: (i) −x+1, −y+1, −z+2.

References

Enraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621–632. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009a). Acta Cryst. E65, o576. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2009b). Acta Cryst. E65, o3275. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nirmala, P. G., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o1017. Web of Science CSD CrossRef IUCr Journals Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Perlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780–o782. Web of Science CSD CrossRef IUCr Journals Google Scholar
Savitha, M. B. & Gowda, B. T. (2006). Z. Naturforsch. Teil A, 60, 600–606. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar

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