N-(3,5-Dimethyl­phen­yl)-2,4-dimethyl­benzene­sulfonamide

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

doi:10.1107/S1600536809050740

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3275

doi:10.1107/S1600536809050740

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N-(3,5-Dimethylphenyl)-2,4-dimethylbenzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. G. Nirmala ^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 25 November 2009; accepted 25 November 2009; online 28 November 2009)

In the title compound, C₁₆H₁₉NO₂S, the molecule is twisted about the S—N bond, the C—S(O₂)—N(H)—C torsion angle being 53.9 (2)°. The dihedral angle between the two benzene rings is 82.1 (1)°. The crystal structure features inversion-related dimers linked by N—H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C₁₆H₁₉NO₂S
M_r = 289.38
Monoclinic, C 2/c
a = 23.490 (2) Å
b = 8.1528 (6) Å
c = 16.544 (1) Å
β = 102.690 (8)°
V = 3090.9 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 299 K
0.40 × 0.20 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with 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 = 0.921, T_max = 0.975
6232 measured reflections
2751 independent reflections
2009 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.118
S = 1.01
2751 reflections
188 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 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
N1—H1N⋯O1ⁱ	0.84 (2)	2.10 (2)	2.945 (3)	176 (3)
Symmetry code: (i) -x, -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/S1600536809050740/tk2587sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050740/tk2587Isup2.hkl

checkCIF report

Comment top

As part of a study of substituent effects on the structures of N-(aryl)arylsulfonamides (Gowda et al., 2009a,b; Nirmala et al., 2009), in the present work, the structure of 2,4-dimethyl-N-(3,5-dimethylphenyl)benzenesulfonamide (I) has been determined (Fig. 1). The molecule is bent at the S–O bond atom with the C1—SO₂—NH—C7 torsion angle being 53.9 (2)°, compared to the values of 46.1 (3)° and 47.7 (3)° in the two independent molecules of 2,4-dimethyl-N-(3,5-dimethylphenyl)benzenesulfonamide (II) (Gowda et al., 2009a), 67.9 (2)° in N-(3,5-dimethylphenyl)benzenesulfonamide (III) (Nirmala et al., 2009) and -69.7 (2)° in 2,4-dimethyl-N-(3,4-dichlorophenyl)benzenesulfonamide (IV) (Gowda et al., 2009b).

The two benzene rings in (I) are tilted relative to each other by 82.1 (1)°, compared to the values of 67.5 (1)° (molecule 1) and 72.9 (1)° (molecule 2) in the two independent molecules of (II), 54.6 (1)° in (III) and 82.4 (1)° in (IV). The other 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) is through pairs of N—H···O(S) hydrogen bonds (Table 1).

Related literature top

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

Experimental top

The solution of m-xylene (10 cc) in chloroform (40 cc) was treated drop-wise with chlorosulfonic acid (25 ml) at 273 K. 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 a stoichiometric ratio of 3,4-dimethylaniline 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- (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). The 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 (I), 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.

N-(3,5-Dimethylphenyl)-2,4-dimethylbenzenesulfonamide top

Crystal data top

C₁₆H₁₉NO₂S	F(000) = 1232
M_r = 289.38	D_x = 1.244 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2194 reflections
a = 23.490 (2) Å	θ = 2.5–27.9°
b = 8.1528 (6) Å	µ = 0.21 mm⁻¹
c = 16.544 (1) Å	T = 299 K
β = 102.690 (8)°	Prism, colourless
V = 3090.9 (4) Å³	0.40 × 0.20 × 0.12 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2751 independent reflections
Radiation source: fine-focus sealed tube	2009 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Rotation method data acquisition using ω and ϕ scans.	θ_max = 25.3°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −28→17
T_min = 0.921, T_max = 0.975	k = −9→9
6232 measured reflections	l = −19→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0512P)² + 3.0162P] where P = (F_o² + 2F_c²)/3
2751 reflections	(Δ/σ)_max = 0.004
188 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₆H₁₉NO₂S	V = 3090.9 (4) Å³
M_r = 289.38	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.490 (2) Å	µ = 0.21 mm⁻¹
b = 8.1528 (6) Å	T = 299 K
c = 16.544 (1) Å	0.40 × 0.20 × 0.12 mm
β = 102.690 (8)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2751 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2009 reflections with I > 2σ(I)
T_min = 0.921, T_max = 0.975	R_int = 0.018
6232 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	1 restraint
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.19 e Å⁻³
2751 reflections	Δρ_min = −0.28 e Å⁻³
188 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
S1	0.05610 (3)	0.54362 (8)	0.39886 (4)	0.0472 (2)
O1	−0.00491 (7)	0.5510 (2)	0.40012 (10)	0.0581 (5)
O2	0.08128 (8)	0.6784 (2)	0.36408 (12)	0.0655 (5)
N1	0.08841 (9)	0.5250 (3)	0.49593 (13)	0.0519 (5)
H1N	0.0648 (10)	0.498 (3)	0.5253 (15)	0.062*
C1	0.07002 (9)	0.3654 (3)	0.34572 (13)	0.0382 (5)
C2	0.05851 (9)	0.2067 (3)	0.37077 (14)	0.0421 (5)
C3	0.06794 (10)	0.0785 (3)	0.32105 (16)	0.0492 (6)
H3	0.0611	−0.0277	0.3372	0.059*
C4	0.08716 (10)	0.0999 (3)	0.24799 (16)	0.0498 (6)
C5	0.09849 (10)	0.2566 (3)	0.22560 (15)	0.0525 (6)
H5	0.1119	0.2739	0.1774	0.063*
C6	0.09019 (10)	0.3886 (3)	0.27382 (15)	0.0480 (6)
H6	0.0982	0.4940	0.2580	0.058*
C7	0.14835 (10)	0.4895 (3)	0.52826 (15)	0.0458 (6)
C8	0.16296 (10)	0.4248 (3)	0.60749 (15)	0.0508 (6)
H8	0.1337	0.4019	0.6357	0.061*
C9	0.22056 (11)	0.3939 (3)	0.64514 (17)	0.0606 (7)
C10	0.26309 (12)	0.4250 (4)	0.60070 (19)	0.0675 (8)
H10	0.3019	0.4029	0.6252	0.081*
C11	0.24971 (11)	0.4873 (4)	0.52134 (18)	0.0612 (8)
C12	0.19150 (11)	0.5218 (3)	0.48498 (17)	0.0564 (7)
H12	0.1817	0.5663	0.4320	0.068*
C13	0.03632 (13)	0.1703 (4)	0.44804 (16)	0.0636 (7)
H13A	0.0022	0.2352	0.4479	0.076*
H13B	0.0660	0.1966	0.4961	0.076*
H13C	0.0266	0.0561	0.4491	0.076*
C14	0.09508 (14)	−0.0463 (4)	0.1958 (2)	0.0796 (9)
H14A	0.0580	−0.0979	0.1752	0.096*
H14B	0.1212	−0.1231	0.2289	0.096*
H14C	0.1111	−0.0109	0.1501	0.096*
C15	0.23625 (14)	0.3267 (5)	0.7320 (2)	0.0931 (11)
H15A	0.2522	0.2184	0.7310	0.112*
H15B	0.2019	0.3220	0.7544	0.112*
H15C	0.2647	0.3968	0.7659	0.112*
C16	0.29662 (13)	0.5197 (5)	0.4739 (2)	0.0881 (11)
H16A	0.3020	0.4238	0.4428	0.106*
H16B	0.3325	0.5457	0.5121	0.106*
H16C	0.2852	0.6102	0.4368	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0477 (4)	0.0440 (4)	0.0490 (4)	0.0102 (3)	0.0089 (3)	0.0005 (3)
O1	0.0450 (9)	0.0733 (12)	0.0548 (10)	0.0213 (9)	0.0082 (8)	−0.0019 (10)
O2	0.0843 (13)	0.0390 (10)	0.0738 (13)	0.0028 (9)	0.0189 (10)	0.0074 (10)
N1	0.0434 (12)	0.0667 (14)	0.0455 (12)	0.0089 (10)	0.0098 (9)	−0.0063 (11)
C1	0.0364 (11)	0.0397 (13)	0.0386 (12)	0.0039 (9)	0.0083 (9)	0.0025 (10)
C2	0.0403 (13)	0.0429 (13)	0.0435 (12)	0.0022 (10)	0.0103 (10)	0.0042 (11)
C3	0.0502 (14)	0.0397 (13)	0.0576 (15)	0.0004 (11)	0.0114 (12)	0.0040 (12)
C4	0.0441 (13)	0.0535 (16)	0.0507 (14)	0.0080 (11)	0.0078 (11)	−0.0066 (13)
C5	0.0549 (15)	0.0656 (18)	0.0405 (13)	0.0069 (13)	0.0177 (11)	0.0018 (13)
C6	0.0504 (14)	0.0478 (14)	0.0471 (14)	0.0012 (11)	0.0134 (11)	0.0089 (12)
C7	0.0405 (13)	0.0456 (14)	0.0498 (14)	0.0034 (10)	0.0065 (10)	−0.0145 (12)
C8	0.0473 (14)	0.0528 (15)	0.0512 (15)	0.0002 (11)	0.0086 (11)	−0.0078 (13)
C9	0.0523 (16)	0.0623 (17)	0.0615 (17)	−0.0007 (13)	0.0002 (13)	−0.0054 (15)
C10	0.0425 (15)	0.080 (2)	0.074 (2)	0.0033 (14)	−0.0010 (13)	−0.0087 (17)
C11	0.0429 (14)	0.0707 (19)	0.0708 (19)	−0.0047 (13)	0.0140 (13)	−0.0191 (16)
C12	0.0518 (15)	0.0667 (18)	0.0498 (14)	−0.0008 (13)	0.0095 (12)	−0.0092 (14)
C13	0.0804 (19)	0.0584 (17)	0.0598 (17)	−0.0053 (14)	0.0324 (14)	0.0097 (15)
C14	0.089 (2)	0.075 (2)	0.076 (2)	0.0131 (18)	0.0195 (17)	−0.0212 (18)
C15	0.069 (2)	0.116 (3)	0.083 (2)	−0.0011 (19)	−0.0087 (16)	0.024 (2)
C16	0.0550 (18)	0.120 (3)	0.094 (2)	−0.0072 (18)	0.0268 (16)	−0.016 (2)

Geometric parameters (Å, º) top

S1—O2	1.4276 (18)	C8—H8	0.9300
S1—O1	1.4392 (17)	C9—C10	1.388 (4)
S1—N1	1.626 (2)	C9—C15	1.506 (4)
S1—C1	1.766 (2)	C10—C11	1.378 (4)
N1—C7	1.422 (3)	C10—H10	0.9300
N1—H1N	0.844 (16)	C11—C12	1.396 (3)
C1—C6	1.386 (3)	C11—C16	1.510 (4)
C1—C2	1.403 (3)	C12—H12	0.9300
C2—C3	1.378 (3)	C13—H13A	0.9600
C2—C13	1.512 (3)	C13—H13B	0.9600
C3—C4	1.391 (3)	C13—H13C	0.9600
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.373 (4)	C14—H14B	0.9600
C4—C14	1.507 (4)	C14—H14C	0.9600
C5—C6	1.379 (3)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C7—C8	1.384 (3)	C16—H16A	0.9600
C7—C12	1.389 (3)	C16—H16B	0.9600
C8—C9	1.383 (3)	C16—H16C	0.9600

O2—S1—O1	118.40 (11)	C10—C9—C15	121.2 (3)
O2—S1—N1	108.98 (12)	C11—C10—C9	122.1 (2)
O1—S1—N1	103.88 (11)	C11—C10—H10	118.9
O2—S1—C1	107.12 (11)	C9—C10—H10	118.9
O1—S1—C1	109.61 (10)	C10—C11—C12	118.8 (2)
N1—S1—C1	108.52 (11)	C10—C11—C16	121.3 (3)
C7—N1—S1	126.83 (17)	C12—C11—C16	119.9 (3)
C7—N1—H1N	117.0 (19)	C7—C12—C11	119.8 (3)
S1—N1—H1N	111.7 (19)	C7—C12—H12	120.1
C6—C1—C2	120.2 (2)	C11—C12—H12	120.1
C6—C1—S1	116.78 (18)	C2—C13—H13A	109.5
C2—C1—S1	122.89 (17)	C2—C13—H13B	109.5
C3—C2—C1	117.2 (2)	H13A—C13—H13B	109.5
C3—C2—C13	119.1 (2)	C2—C13—H13C	109.5
C1—C2—C13	123.7 (2)	H13A—C13—H13C	109.5
C2—C3—C4	123.3 (2)	H13B—C13—H13C	109.5
C2—C3—H3	118.3	C4—C14—H14A	109.5
C4—C3—H3	118.3	C4—C14—H14B	109.5
C5—C4—C3	118.1 (2)	H14A—C14—H14B	109.5
C5—C4—C14	121.7 (2)	C4—C14—H14C	109.5
C3—C4—C14	120.2 (3)	H14A—C14—H14C	109.5
C4—C5—C6	120.7 (2)	H14B—C14—H14C	109.5
C4—C5—H5	119.7	C9—C15—H15A	109.5
C6—C5—H5	119.7	C9—C15—H15B	109.5
C5—C6—C1	120.6 (2)	H15A—C15—H15B	109.5
C5—C6—H6	119.7	C9—C15—H15C	109.5
C1—C6—H6	119.7	H15A—C15—H15C	109.5
C8—C7—C12	120.2 (2)	H15B—C15—H15C	109.5
C8—C7—N1	116.9 (2)	C11—C16—H16A	109.5
C12—C7—N1	122.8 (2)	C11—C16—H16B	109.5
C9—C8—C7	120.7 (2)	H16A—C16—H16B	109.5
C9—C8—H8	119.7	C11—C16—H16C	109.5
C7—C8—H8	119.7	H16A—C16—H16C	109.5
C8—C9—C10	118.4 (3)	H16B—C16—H16C	109.5
C8—C9—C15	120.4 (3)

O2—S1—N1—C7	−62.4 (2)	C14—C4—C5—C6	179.1 (2)
O1—S1—N1—C7	170.5 (2)	C4—C5—C6—C1	−0.2 (4)
C1—S1—N1—C7	53.9 (2)	C2—C1—C6—C5	0.8 (3)
O2—S1—C1—C6	−12.4 (2)	S1—C1—C6—C5	−175.71 (18)
O1—S1—C1—C6	117.20 (18)	S1—N1—C7—C8	−158.6 (2)
N1—S1—C1—C6	−129.97 (18)	S1—N1—C7—C12	23.5 (4)
O2—S1—C1—C2	171.16 (18)	C12—C7—C8—C9	1.0 (4)
O1—S1—C1—C2	−59.2 (2)	N1—C7—C8—C9	−177.0 (2)
N1—S1—C1—C2	53.6 (2)	C7—C8—C9—C10	−1.8 (4)
C6—C1—C2—C3	−0.2 (3)	C7—C8—C9—C15	178.8 (3)
S1—C1—C2—C3	176.07 (17)	C8—C9—C10—C11	1.0 (4)
C6—C1—C2—C13	−179.8 (2)	C15—C9—C10—C11	−179.6 (3)
S1—C1—C2—C13	−3.6 (3)	C9—C10—C11—C12	0.6 (4)
C1—C2—C3—C4	−1.0 (3)	C9—C10—C11—C16	−179.8 (3)
C13—C2—C3—C4	178.7 (2)	C8—C7—C12—C11	0.7 (4)
C2—C3—C4—C5	1.5 (4)	N1—C7—C12—C11	178.5 (2)
C2—C3—C4—C14	−178.5 (2)	C10—C11—C12—C7	−1.5 (4)
C3—C4—C5—C6	−0.9 (4)	C16—C11—C12—C7	179.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.84 (2)	2.10 (2)	2.945 (3)	176 (3)

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉NO₂S
M_r	289.38
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	299
a, b, c (Å)	23.490 (2), 8.1528 (6), 16.544 (1)
β (°)	102.690 (8)
V (Å³)	3090.9 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.40 × 0.20 × 0.12

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.921, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	6232, 2751, 2009
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.118, 1.01
No. of reflections	2751
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)	0.19, −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
N1—H1N···O1ⁱ	0.844 (16)	2.102 (17)	2.945 (3)	176 (3)

Symmetry code: (i) −x, −y+1, −z+1.

References

Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621–632. Web of Science CSD CrossRef IUCr Journals Google Scholar
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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
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef IUCr Journals Google Scholar

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Volume 65| Part 12| December 2009| Page o3275

doi:10.1107/S1600536809050740

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