N-(3,5-Dimethyl­phen­yl)-4-methyl­benzene­sulfonamide

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

doi:10.1107/S1600536809053057

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o144

doi:10.1107/S1600536809053057

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N-(3,5-Dimethylphenyl)-4-methylbenzenesulfonamide

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 8 December 2009; accepted 9 December 2009; online 16 December 2009)

In the title compound, C₁₅H₁₇NO₂S, the dihedral angle between the two aromatic rings is 53.9 (1)°. The crystal structure features inversion-related dimers linked by N—H⋯O hydrogen bonds.

Related literature

For preparation of the title compound, see: Shetty & Gowda (2005 ). For our study of the effects of substituents on the structures of N-(aryl)-arylsulfonamides, see: Gowda et al. (2010 ); Nirmala et al. (2009a ,b ). For related structures, see: Gelbrich et al. (2007 ); Perlovich et al. (2006 ).

Experimental

Crystal data

C₁₅H₁₇NO₂S
M_r = 275.36
Triclinic, $[P \overline 1]$
a = 8.311 (1) Å
b = 8.521 (1) Å
c = 11.412 (1) Å
α = 99.86 (1)°
β = 97.62 (1)°
γ = 108.14 (1)°
V = 741.60 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 299 K
0.45 × 0.45 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.909, T_max = 0.919
4897 measured reflections
3025 independent reflections
2525 reflections with I > 2σ(I)
R_int = 0.012

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.118
S = 1.06
3025 reflections
179 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.83 (2)	2.11 (2)	2.933 (2)	170 (2)
Symmetry code: (i) -x+2, -y+2, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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/S1600536809053057/bt5135sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809053057/bt5135Isup2.hkl

checkCIF report

Comment top

In the present work, as part of a study of the effect of substituents on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2010; Nirmala et al., 2009a,b), the structure of N-(3,5-dimethylphenyl)4-methylbenzenesulfonamide (I) has been determined. The conformation of the N—C bond in the C1—SO₂—NH—C7 segment of the structure has gauche torsions with respect to the S═ O bonds (Fig. 1). Further, the conformation of the N—H bond is anti to one of the 3-methyl groups and syn to the other in the aniline benzene ring. The molecule is bent at the S atom with the C1—SO₂—NH—C7 torsion angle of 56.8 (2)°, compared to the values of -51.6 (3)° in N-(phenyl)4-methylbenzenesulfonamide (II) (Gowda et al., 2010), 56.7 (3)° in N-(3-methylphenyl)4-methylbenzenesulfonamide (III) (Nirmala et al., 2009a), 67.9 (2)° in N-(3,5-dimethylphenyl)benzenesulfonamide(IV)(Nirmala et al., 2009b) and -61.0 (2)° in N-(2,5-dimethylphenyl)4-methylbenzenesulfonamide (V) and -61.8 (2)° in N-(3,4-dimethylphenyl)4-methylbenzenesulfonamide (VI) (Gowda et al., 2010).

The two benzene rings in (I) are tilted relative to each other by 53.9 (1)° compared to the values of 68.4 (1)° in (II), 83.9 (1)° in (III), 54.6 (1)° in (IV), 49.4 (1)° in (V) and 47.8 (1)° in (VI). The other bond parameters are similar to those observed in (II), (III), (IV), (V), (VI) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

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

Related literature top

For preparation of the title compound, see: Shetty & Gowda (2005). For our study of the effects of substituents on the structures of N-(aryl)-arylsulfonamides, see: Gowda et al. (2010); Nirmala et al. (2009a,b). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

Experimental top

The solution of toluene (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 4-methylbenzenesulfonylchloride 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 N-(3,5-dimethylphenyl)4-methylbenzenesulfonamide 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 (Shetty & Gowda, 2005). The single crystals used in X-ray diffraction studies were grown in ethanolic solution by a 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 the title compound with hydrogen bonding shown as dashed lines.

N-(3,5-Dimethylphenyl)-4-methylbenzenesulfonamide top

Crystal data top

C₁₅H₁₇NO₂S	Z = 2
M_r = 275.36	F(000) = 292
Triclinic, P1	D_x = 1.233 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.311 (1) Å	Cell parameters from 2279 reflections
b = 8.521 (1) Å	θ = 2.6–27.7°
c = 11.412 (1) Å	µ = 0.22 mm⁻¹
α = 99.86 (1)°	T = 299 K
β = 97.62 (1)°	Prism, colourless
γ = 108.14 (1)°	0.45 × 0.45 × 0.40 mm
V = 741.60 (14) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3025 independent reflections
Radiation source: fine-focus sealed tube	2525 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.012
Rotation method data acquisition using ω and phi scans	θ_max = 26.4°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→9
T_min = 0.909, T_max = 0.919	k = −10→10
4897 measured reflections	l = −14→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.118	w = 1/[σ²(F_o²) + (0.0643P)² + 0.1701P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.025
3025 reflections	Δρ_max = 0.27 e Å⁻³
179 parameters	Δρ_min = −0.31 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.087 (7)

Crystal data top

C₁₅H₁₇NO₂S	γ = 108.14 (1)°
M_r = 275.36	V = 741.60 (14) Å³
Triclinic, P1	Z = 2
a = 8.311 (1) Å	Mo Kα radiation
b = 8.521 (1) Å	µ = 0.22 mm⁻¹
c = 11.412 (1) Å	T = 299 K
α = 99.86 (1)°	0.45 × 0.45 × 0.40 mm
β = 97.62 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3025 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2525 reflections with I > 2σ(I)
T_min = 0.909, T_max = 0.919	R_int = 0.012
4897 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	1 restraint
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.27 e Å⁻³
3025 reflections	Δρ_min = −0.31 e Å⁻³
179 parameters

Special details top

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

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	0.81313 (5)	1.06718 (5)	0.37422 (4)	0.04434 (17)
O1	0.91624 (16)	1.14988 (15)	0.49312 (11)	0.0528 (3)
O2	0.76542 (18)	1.16623 (17)	0.29675 (13)	0.0587 (4)
N1	0.92841 (19)	0.9671 (2)	0.30816 (13)	0.0485 (4)
H1N	0.977 (3)	0.928 (3)	0.3581 (17)	0.058*
C1	0.6248 (2)	0.9101 (2)	0.38708 (15)	0.0413 (4)
C2	0.4799 (2)	0.8575 (3)	0.29635 (18)	0.0550 (5)
H2	0.4794	0.9097	0.2312	0.066*
C3	0.3358 (2)	0.7272 (3)	0.3029 (2)	0.0612 (5)
H3	0.2378	0.6926	0.2418	0.073*
C4	0.3338 (2)	0.6468 (2)	0.3982 (2)	0.0565 (5)
C5	0.4797 (3)	0.7038 (3)	0.4893 (2)	0.0617 (5)
H5	0.4794	0.6531	0.5552	0.074*
C6	0.6256 (2)	0.8341 (2)	0.48470 (17)	0.0541 (5)
H6	0.7230	0.8701	0.5464	0.065*
C7	0.8582 (2)	0.8517 (2)	0.19231 (15)	0.0457 (4)
C8	0.8165 (3)	0.9108 (3)	0.09055 (17)	0.0566 (5)
H8	0.8323	1.0252	0.0976	0.068*
C9	0.7514 (3)	0.7991 (3)	−0.02150 (18)	0.0640 (5)
C10	0.7315 (3)	0.6301 (3)	−0.03010 (19)	0.0695 (6)
H10	0.6872	0.5549	−0.1054	0.083*
C11	0.7759 (3)	0.5689 (3)	0.07052 (19)	0.0629 (5)
C12	0.8382 (2)	0.6827 (3)	0.18233 (17)	0.0530 (4)
H12	0.8668	0.6447	0.2512	0.064*
C13	0.1768 (3)	0.5018 (3)	0.4026 (3)	0.0824 (8)
H13A	0.0804	0.5406	0.4061	0.099*
H13B	0.1993	0.4592	0.4734	0.099*
H13C	0.1505	0.4131	0.3313	0.099*
C14	0.7039 (4)	0.8623 (4)	−0.1327 (2)	0.0946 (9)
H14A	0.5812	0.8369	−0.1510	0.113*
H14B	0.7392	0.8075	−0.2003	0.113*
H14C	0.7613	0.9827	−0.1174	0.113*
C15	0.7573 (4)	0.3850 (3)	0.0585 (3)	0.0952 (9)
H15A	0.6505	0.3153	0.0046	0.114*
H15B	0.7577	0.3579	0.1368	0.114*
H15C	0.8520	0.3645	0.0266	0.114*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0445 (3)	0.0386 (2)	0.0471 (3)	0.00888 (17)	0.00667 (18)	0.01407 (18)
O1	0.0526 (7)	0.0424 (7)	0.0528 (7)	0.0073 (5)	0.0022 (6)	0.0067 (6)
O2	0.0648 (8)	0.0499 (7)	0.0652 (8)	0.0178 (6)	0.0106 (7)	0.0280 (7)
N1	0.0437 (8)	0.0558 (9)	0.0448 (8)	0.0144 (7)	0.0068 (6)	0.0145 (7)
C1	0.0405 (8)	0.0376 (8)	0.0448 (9)	0.0119 (7)	0.0082 (7)	0.0093 (7)
C2	0.0479 (10)	0.0609 (12)	0.0535 (11)	0.0149 (9)	0.0042 (8)	0.0176 (9)
C3	0.0420 (10)	0.0599 (12)	0.0691 (13)	0.0089 (8)	0.0020 (9)	0.0045 (10)
C4	0.0468 (10)	0.0402 (9)	0.0802 (14)	0.0109 (8)	0.0223 (9)	0.0072 (9)
C5	0.0647 (12)	0.0540 (11)	0.0706 (13)	0.0150 (9)	0.0225 (10)	0.0281 (10)
C6	0.0514 (10)	0.0519 (10)	0.0546 (11)	0.0096 (8)	0.0049 (8)	0.0203 (9)
C7	0.0406 (9)	0.0540 (10)	0.0431 (9)	0.0136 (7)	0.0111 (7)	0.0153 (8)
C8	0.0644 (12)	0.0592 (12)	0.0521 (11)	0.0235 (10)	0.0135 (9)	0.0224 (9)
C9	0.0738 (14)	0.0770 (14)	0.0473 (11)	0.0312 (11)	0.0081 (9)	0.0224 (10)
C10	0.0846 (15)	0.0734 (14)	0.0468 (11)	0.0286 (12)	0.0047 (10)	0.0075 (10)
C11	0.0757 (14)	0.0589 (12)	0.0533 (11)	0.0238 (10)	0.0093 (10)	0.0123 (9)
C12	0.0574 (11)	0.0605 (11)	0.0465 (10)	0.0229 (9)	0.0109 (8)	0.0207 (9)
C13	0.0585 (13)	0.0538 (12)	0.130 (2)	0.0071 (10)	0.0356 (14)	0.0180 (14)
C14	0.126 (2)	0.113 (2)	0.0554 (14)	0.0512 (19)	0.0057 (14)	0.0353 (14)
C15	0.140 (3)	0.0633 (15)	0.0771 (17)	0.0353 (16)	0.0095 (17)	0.0107 (13)

Geometric parameters (Å, º) top

S1—O2	1.4220 (13)	C8—C9	1.383 (3)
S1—O1	1.4353 (13)	C8—H8	0.9300
S1—N1	1.6414 (16)	C9—C10	1.382 (3)
S1—C1	1.7570 (17)	C9—C14	1.513 (3)
N1—C7	1.431 (2)	C10—C11	1.393 (3)
N1—H1N	0.830 (15)	C10—H10	0.9300
C1—C2	1.378 (2)	C11—C12	1.388 (3)
C1—C6	1.381 (2)	C11—C15	1.506 (3)
C2—C3	1.378 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—H13A	0.9600
C3—C4	1.381 (3)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.382 (3)	C14—H14A	0.9600
C4—C13	1.506 (3)	C14—H14B	0.9600
C5—C6	1.380 (3)	C14—H14C	0.9600
C5—H5	0.9300	C15—H15A	0.9600
C6—H6	0.9300	C15—H15B	0.9600
C7—C12	1.380 (3)	C15—H15C	0.9600
C7—C8	1.387 (2)

O2—S1—O1	119.35 (8)	C7—C8—H8	120.1
O2—S1—N1	108.43 (8)	C10—C9—C8	119.03 (19)
O1—S1—N1	104.34 (8)	C10—C9—C14	120.8 (2)
O2—S1—C1	108.50 (8)	C8—C9—C14	120.1 (2)
O1—S1—C1	109.14 (8)	C9—C10—C11	122.0 (2)
N1—S1—C1	106.34 (8)	C9—C10—H10	119.0
C7—N1—S1	120.83 (12)	C11—C10—H10	119.0
C7—N1—H1N	112.8 (15)	C12—C11—C10	117.9 (2)
S1—N1—H1N	109.6 (15)	C12—C11—C15	121.0 (2)
C2—C1—C6	120.44 (16)	C10—C11—C15	121.1 (2)
C2—C1—S1	119.58 (13)	C7—C12—C11	120.66 (17)
C6—C1—S1	119.90 (13)	C7—C12—H12	119.7
C3—C2—C1	119.53 (18)	C11—C12—H12	119.7
C3—C2—H2	120.2	C4—C13—H13A	109.5
C1—C2—H2	120.2	C4—C13—H13B	109.5
C2—C3—C4	121.32 (18)	H13A—C13—H13B	109.5
C2—C3—H3	119.3	C4—C13—H13C	109.5
C4—C3—H3	119.3	H13A—C13—H13C	109.5
C5—C4—C3	118.06 (17)	H13B—C13—H13C	109.5
C5—C4—C13	121.2 (2)	C9—C14—H14A	109.5
C3—C4—C13	120.7 (2)	C9—C14—H14B	109.5
C4—C5—C6	121.66 (19)	H14A—C14—H14B	109.5
C4—C5—H5	119.2	C9—C14—H14C	109.5
C6—C5—H5	119.2	H14A—C14—H14C	109.5
C5—C6—C1	118.96 (18)	H14B—C14—H14C	109.5
C5—C6—H6	120.5	C11—C15—H15A	109.5
C1—C6—H6	120.5	C11—C15—H15B	109.5
C12—C7—C8	120.51 (18)	H15A—C15—H15B	109.5
C12—C7—N1	119.34 (16)	C11—C15—H15C	109.5
C8—C7—N1	120.11 (17)	H15A—C15—H15C	109.5
C9—C8—C7	119.83 (19)	H15B—C15—H15C	109.5
C9—C8—H8	120.1

O2—S1—N1—C7	−59.70 (15)	C2—C1—C6—C5	0.6 (3)
O1—S1—N1—C7	172.11 (13)	S1—C1—C6—C5	−176.08 (15)
C1—S1—N1—C7	56.80 (15)	S1—N1—C7—C12	−116.91 (17)
O2—S1—C1—C2	24.58 (17)	S1—N1—C7—C8	65.4 (2)
O1—S1—C1—C2	156.11 (15)	C12—C7—C8—C9	1.2 (3)
N1—S1—C1—C2	−91.87 (16)	N1—C7—C8—C9	178.92 (17)
O2—S1—C1—C6	−158.72 (15)	C7—C8—C9—C10	−1.0 (3)
O1—S1—C1—C6	−27.19 (17)	C7—C8—C9—C14	179.4 (2)
N1—S1—C1—C6	84.83 (16)	C8—C9—C10—C11	−0.3 (4)
C6—C1—C2—C3	−0.6 (3)	C14—C9—C10—C11	179.3 (2)
S1—C1—C2—C3	176.04 (15)	C9—C10—C11—C12	1.4 (4)
C1—C2—C3—C4	−0.5 (3)	C9—C10—C11—C15	−178.5 (3)
C2—C3—C4—C5	1.6 (3)	C8—C7—C12—C11	−0.1 (3)
C2—C3—C4—C13	−178.55 (19)	N1—C7—C12—C11	−177.81 (17)
C3—C4—C5—C6	−1.7 (3)	C10—C11—C12—C7	−1.2 (3)
C13—C4—C5—C6	178.5 (2)	C15—C11—C12—C7	178.7 (2)
C4—C5—C6—C1	0.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.83 (2)	2.11 (2)	2.933 (2)	170 (2)

Symmetry code: (i) −x+2, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇NO₂S
M_r	275.36
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	8.311 (1), 8.521 (1), 11.412 (1)
α, β, γ (°)	99.86 (1), 97.62 (1), 108.14 (1)
V (Å³)	741.60 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.45 × 0.45 × 0.40

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	0.909, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	4897, 3025, 2525
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.118, 1.06
No. of reflections	3025
No. of parameters	179
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)	0.27, −0.31

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	0.830 (15)	2.111 (16)	2.933 (2)	170 (2)

Symmetry code: (i) −x+2, −y+2, −z+1.

References

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Volume 66| Part 1| January 2010| Page o144

doi:10.1107/S1600536809053057

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