organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2-Chloro-N-(4-meth­­oxy­benzo­yl)­benzene­sulfonamide

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, bDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, cDepartment of Studies in Microbiology, University of Mysore, Manasagangotri, Mysore, India, dDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore, India, and eDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
*Correspondence e-mail: pasuchetan@yahoo.co.in

(Received 19 January 2014; accepted 21 January 2014; online 25 January 2014)

In the title compound, C14H12ClNO4S, the dihedral angle between the aromatic rings is 82.07 (1)° and the dihedral angle between the planes defined by the S—N—C=O fragment and the sulfonyl benzene ring is 82.46 (3)°. In the crystal, the mol­ecules are linked into C(4) chains running along [001] by strong N—H⋯O hydrogen bonds. A C—H⋯O intera­ction reinforces the [001] chains: its graph-set symbol is C(7). The chains are cross-linked into (100) sheets by further C—H⋯O inter­actions as C(6) chains along [001]. The structure also features weak ππ stacking inter­actions [centroid–centroid distances = 3.577 (1) and 3.8016 (1) Å].

Related literature

For related structures see: Gowda et al. (2010a[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010a). Acta Cryst. E66, o794.],b[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010b). Acta Cryst. E66, o1466.]); Suchetan et al. (2011a[Suchetan, P. A., Foro, S. & Gowda, B. T. (2011a). Acta Cryst. E67, o146.],b[Suchetan, P. A., Foro, S. & Gowda, B. T. (2011b). Acta Cryst. E67, o930.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12ClNO4S

  • Mr = 325.76

  • Monoclinic, P 21 /c

  • a = 14.5293 (19) Å

  • b = 10.6225 (14) Å

  • c = 9.6918 (14) Å

  • β = 92.695 (5)°

  • V = 1494.2 (4) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 3.71 mm−1

  • T = 293 K

  • 0.44 × 0.35 × 0.26 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS, and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.263, Tmax = 0.381

  • 17846 measured reflections

  • 2449 independent reflections

  • 2295 reflections with I > 2σ(I)

  • Rint = 0.058

Refinement
  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 0.163

  • S = 1.11

  • 2449 reflections

  • 195 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.52 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2i 0.81 (3) 2.09 (3) 2.872 (3) 172 (3)
C3—H3⋯O1ii 0.93 2.57 3.370 (4) 144
C9—H9⋯O2i 0.93 2.48 3.288 (3) 145
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS, and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SADABS, and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.

Supporting information


Introduction top

As a part of our continued structural studies of N-(aroyl)-aryl­sulfonamides (Suchetan et al., 2011a, 2011b; Gowda et al., 2010a, 2010b), we report here the crystal structure of the title compound (I) (Fig 1).

Experimental top

Synthesis and crystallization top

The title compound (I) was prepared by refluxing a mixture of 4-meth­oxy­benzoic acid, 2-chloro­benzene­sulfonamide and phospho­rous oxychloride (POCl3) for 2 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The compound obtained was filtered and later dried (Melting point: 445 K).

Colorless prisms of (I) were obtained from a slow evaporation of its aqueous methano­lic solution at room temperature.

Refinement top

The H atom of the NH group was located in a difference map and later refined freely. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93-0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times of the U eq of the parent atom).

Results and discussion top

In I, the dihedral angle between the two aromatic rings is 82.07 (1)°. Compared to this, the dihedral angle is 73.3 (1)° in N-(benzoyl)-2-chloro­benzene­sulfonamide (II, Gowda et al., 2010a), 85.7 (1)° in N-(4-chloro­benzoyl)-2-chloro­benzene­sulfonamide (III, Suchetan et al., 2011a), 89.1 (2)° in N-(4-methyl­benzoyl)-2-chloro­benzene­sulfonamide (IV, Gowda et al., 2010b) and 85.4 (1)° in N-(4-nitro­benzoyl)-2-chloro­benzene­sulfonamide (V, Suchetan et al., 2011b). This shows that introducing a substituent into the para position of the benzoyl ring of II correlates with a increase of the dihedral angle between the aromatic rings. Further, the molecule is twisted at the S atom, the dihedral angle between the planes defined by the S—N—C=O segment in the central chain and the sulfonyl benzene ring being 82.46 (3)°.

In the crystal structure, the molecules are linked into C(4) chains running along [001] through strong N1—H1···O2 hydrogen bonds (Figure 2). The molecules are further linked into one another through C3—H3···O1 (Figure 3) and C9—H9···O2 (Figure 4) inter­actions into C(6) and C(7) chains running along [001]. The structure is further stabilized by two alternate π-π inter­actions, Cg(meth­oxy­phenyl)-Cg(meth­oxy­phenyl) and Cg(chloro­phenyl)-Cg(chloro­phenyl) distances being respectively 3.577 (1)Å and 3.8016 (1)Å.

Related literature top

For related structures see: Gowda et al. (2010a,b); Suchetan et al. (2011a,b).

Structure description top

As a part of our continued structural studies of N-(aroyl)-aryl­sulfonamides (Suchetan et al., 2011a, 2011b; Gowda et al., 2010a, 2010b), we report here the crystal structure of the title compound (I) (Fig 1).

In I, the dihedral angle between the two aromatic rings is 82.07 (1)°. Compared to this, the dihedral angle is 73.3 (1)° in N-(benzoyl)-2-chloro­benzene­sulfonamide (II, Gowda et al., 2010a), 85.7 (1)° in N-(4-chloro­benzoyl)-2-chloro­benzene­sulfonamide (III, Suchetan et al., 2011a), 89.1 (2)° in N-(4-methyl­benzoyl)-2-chloro­benzene­sulfonamide (IV, Gowda et al., 2010b) and 85.4 (1)° in N-(4-nitro­benzoyl)-2-chloro­benzene­sulfonamide (V, Suchetan et al., 2011b). This shows that introducing a substituent into the para position of the benzoyl ring of II correlates with a increase of the dihedral angle between the aromatic rings. Further, the molecule is twisted at the S atom, the dihedral angle between the planes defined by the S—N—C=O segment in the central chain and the sulfonyl benzene ring being 82.46 (3)°.

In the crystal structure, the molecules are linked into C(4) chains running along [001] through strong N1—H1···O2 hydrogen bonds (Figure 2). The molecules are further linked into one another through C3—H3···O1 (Figure 3) and C9—H9···O2 (Figure 4) inter­actions into C(6) and C(7) chains running along [001]. The structure is further stabilized by two alternate π-π inter­actions, Cg(meth­oxy­phenyl)-Cg(meth­oxy­phenyl) and Cg(chloro­phenyl)-Cg(chloro­phenyl) distances being respectively 3.577 (1)Å and 3.8016 (1)Å.

For related structures see: Gowda et al. (2010a,b); Suchetan et al. (2011a,b).

Synthesis and crystallization top

The title compound (I) was prepared by refluxing a mixture of 4-meth­oxy­benzoic acid, 2-chloro­benzene­sulfonamide and phospho­rous oxychloride (POCl3) for 2 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The compound obtained was filtered and later dried (Melting point: 445 K).

Colorless prisms of (I) were obtained from a slow evaporation of its aqueous methano­lic solution at room temperature.

Refinement details top

The H atom of the NH group was located in a difference map and later refined freely. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93-0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times of the U eq of the parent atom).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Formation of C(4) chains through N—H···O hydrogen bonds.
[Figure 3] Fig. 3. Formation of C(6) chains through C3—H3···O1 interactions running along [001].
[Figure 4] Fig. 4. Formation of C(7) chains through C9—H9···O2 interactions running along [001].
[Figure 5] Fig. 5. π-π stacking interactions observed in the crystal structure of I.
2-Chloro-N-(4-methoxybenzoyl)benzenesulfonamide top
Crystal data top
C14H12ClNO4SPrism
Mr = 325.76Dx = 1.448 Mg m3
Monoclinic, P21/cMelting point: 445 K
Hall symbol: -P 2ybcCu Kα radiation, λ = 1.54178 Å
a = 14.5293 (19) ÅCell parameters from 25 reflections
b = 10.6225 (14) Åθ = 3.0–64.6°
c = 9.6918 (14) ŵ = 3.71 mm1
β = 92.695 (5)°T = 293 K
V = 1494.2 (4) Å3Prism, colourless
Z = 40.44 × 0.35 × 0.26 mm
F(000) = 672
Data collection top
Bruker APEXII CCD
diffractometer
2449 independent reflections
Radiation source: fine-focus sealed tube2295 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
phi and φ scansθmax = 64.6°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1616
Tmin = 0.263, Tmax = 0.381k = 1212
17846 measured reflectionsl = 119
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.109P)2 + 0.3886P]
where P = (Fo2 + 2Fc2)/3
2449 reflections(Δ/σ)max < 0.001
195 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.37 e Å3
Crystal data top
C14H12ClNO4SV = 1494.2 (4) Å3
Mr = 325.76Z = 4
Monoclinic, P21/cCu Kα radiation
a = 14.5293 (19) ŵ = 3.71 mm1
b = 10.6225 (14) ÅT = 293 K
c = 9.6918 (14) Å0.44 × 0.35 × 0.26 mm
β = 92.695 (5)°
Data collection top
Bruker APEXII CCD
diffractometer
2449 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2295 reflections with I > 2σ(I)
Tmin = 0.263, Tmax = 0.381Rint = 0.058
17846 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.163H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.52 e Å3
2449 reflectionsΔρmin = 0.37 e Å3
195 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
xyzUiso*/Ueq
H10.718 (2)0.192 (3)0.295 (4)0.066 (10)*
S10.79503 (4)0.19067 (5)0.11546 (6)0.0448 (3)
Cl10.90252 (7)0.02535 (9)0.35628 (9)0.0882 (4)
O10.85786 (12)0.27002 (19)0.1915 (2)0.0592 (5)
O20.75657 (13)0.2343 (2)0.01265 (19)0.0645 (5)
O40.32115 (14)0.1078 (2)0.5017 (3)0.0826 (7)
C90.54708 (16)0.1902 (2)0.3736 (3)0.0497 (6)
H90.59560.24560.39210.060*
C80.55277 (15)0.1039 (2)0.2671 (2)0.0439 (5)
C70.63122 (16)0.0964 (2)0.1759 (2)0.0467 (6)
N10.71064 (13)0.1640 (2)0.2183 (2)0.0482 (5)
O30.62999 (14)0.0385 (2)0.0682 (2)0.0705 (6)
C100.47035 (18)0.1952 (3)0.4531 (3)0.0562 (7)
H100.46730.25430.52350.067*
C130.47841 (19)0.0229 (3)0.2399 (3)0.0603 (7)
H130.48010.03400.16710.072*
C10.84769 (15)0.0440 (2)0.0838 (3)0.0485 (6)
C110.39843 (17)0.1122 (3)0.4276 (3)0.0565 (6)
C20.89668 (17)0.0230 (3)0.1868 (3)0.0604 (7)
C120.4026 (2)0.0265 (3)0.3197 (4)0.0679 (8)
H120.35390.02870.30130.081*
C30.9432 (2)0.1334 (3)0.1497 (5)0.0842 (12)
H30.97760.17870.21600.101*
C60.8439 (2)0.0008 (3)0.0515 (3)0.0638 (7)
H60.81050.04530.11950.077*
C40.9373 (3)0.1740 (3)0.0131 (5)0.0893 (12)
H40.96680.24810.01070.107*
C50.8897 (3)0.1082 (4)0.0854 (5)0.0851 (11)
H50.88770.13620.17650.102*
C140.3152 (3)0.1932 (4)0.6139 (5)0.0940 (13)
H14A0.36760.18230.67680.141*
H14B0.25980.17710.66120.141*
H14C0.31410.27800.57950.141*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0411 (4)0.0523 (4)0.0410 (4)0.0020 (2)0.0010 (3)0.0046 (2)
Cl10.0929 (6)0.0998 (7)0.0690 (6)0.0016 (5)0.0274 (4)0.0253 (4)
O10.0552 (10)0.0589 (10)0.0636 (12)0.0150 (8)0.0034 (8)0.0062 (8)
O20.0623 (11)0.0852 (13)0.0459 (10)0.0168 (10)0.0013 (8)0.0179 (9)
O40.0488 (11)0.0906 (16)0.1105 (19)0.0120 (10)0.0257 (11)0.0087 (13)
C90.0382 (12)0.0555 (14)0.0552 (15)0.0069 (9)0.0011 (10)0.0066 (10)
C80.0404 (11)0.0450 (12)0.0459 (12)0.0027 (9)0.0037 (9)0.0013 (10)
C70.0436 (12)0.0541 (13)0.0418 (13)0.0007 (10)0.0048 (9)0.0023 (10)
N10.0421 (10)0.0628 (12)0.0394 (12)0.0026 (9)0.0010 (8)0.0064 (10)
O30.0594 (11)0.0961 (15)0.0557 (12)0.0101 (10)0.0010 (9)0.0290 (11)
C100.0429 (13)0.0642 (16)0.0616 (16)0.0030 (10)0.0047 (11)0.0110 (12)
C130.0529 (14)0.0595 (15)0.0681 (17)0.0110 (12)0.0015 (12)0.0141 (13)
C10.0368 (11)0.0534 (13)0.0555 (14)0.0019 (9)0.0043 (10)0.0023 (11)
C110.0406 (12)0.0594 (15)0.0697 (17)0.0029 (11)0.0055 (11)0.0053 (13)
C20.0396 (12)0.0604 (16)0.0806 (19)0.0003 (11)0.0018 (12)0.0167 (13)
C120.0467 (14)0.0664 (17)0.091 (2)0.0180 (12)0.0039 (13)0.0085 (15)
C30.0488 (15)0.0647 (19)0.139 (4)0.0075 (13)0.0061 (18)0.030 (2)
C60.0598 (15)0.0699 (17)0.0627 (17)0.0006 (13)0.0115 (13)0.0087 (14)
C40.072 (2)0.066 (2)0.133 (4)0.0070 (16)0.032 (2)0.012 (2)
C50.081 (2)0.077 (2)0.100 (3)0.0035 (18)0.030 (2)0.025 (2)
C140.0640 (19)0.103 (3)0.119 (3)0.0030 (18)0.041 (2)0.016 (2)
Geometric parameters (Å, º) top
S1—O21.4154 (19)C13—C121.375 (4)
S1—O11.4227 (19)C13—H130.9300
S1—N11.641 (2)C1—C61.387 (4)
S1—C11.769 (3)C1—C21.394 (4)
Cl1—C21.720 (3)C11—C121.390 (5)
O4—C111.362 (3)C2—C31.408 (5)
O4—C141.422 (5)C12—H120.9300
C9—C101.385 (4)C3—C41.391 (6)
C9—C81.386 (4)C3—H30.9300
C9—H90.9300C6—C51.383 (5)
C8—C131.396 (3)C6—H60.9300
C8—C71.477 (3)C4—C51.348 (6)
C7—O31.211 (3)C4—H40.9300
C7—N11.404 (3)C5—H50.9300
N1—H10.80 (4)C14—H14A0.9600
C10—C111.381 (4)C14—H14B0.9600
C10—H100.9300C14—H14C0.9600
O2—S1—O1118.55 (13)O4—C11—C10124.3 (3)
O2—S1—N1108.28 (11)O4—C11—C12116.2 (2)
O1—S1—N1105.51 (11)C10—C11—C12119.6 (2)
O2—S1—C1106.98 (13)C1—C2—C3118.5 (3)
O1—S1—C1109.85 (12)C1—C2—Cl1122.2 (2)
N1—S1—C1107.16 (11)C3—C2—Cl1119.3 (3)
C11—O4—C14117.6 (2)C13—C12—C11120.4 (2)
C10—C9—C8121.2 (2)C13—C12—H12119.8
C10—C9—H9119.4C11—C12—H12119.8
C8—C9—H9119.4C4—C3—C2119.5 (3)
C9—C8—C13118.4 (2)C4—C3—H3120.2
C9—C8—C7123.8 (2)C2—C3—H3120.2
C13—C8—C7117.8 (2)C5—C6—C1120.3 (3)
O3—C7—N1119.4 (2)C5—C6—H6119.9
O3—C7—C8124.2 (2)C1—C6—H6119.9
N1—C7—C8116.4 (2)C5—C4—C3121.3 (3)
C7—N1—S1122.55 (18)C5—C4—H4119.4
C7—N1—H1122 (2)C3—C4—H4119.4
S1—N1—H1115 (2)C4—C5—C6120.1 (4)
C11—C10—C9119.9 (2)C4—C5—H5119.9
C11—C10—H10120.1C6—C5—H5119.9
C9—C10—H10120.1O4—C14—H14A109.5
C12—C13—C8120.6 (3)O4—C14—H14B109.5
C12—C13—H13119.7H14A—C14—H14B109.5
C8—C13—H13119.7O4—C14—H14C109.5
C6—C1—C2120.3 (3)H14A—C14—H14C109.5
C6—C1—S1117.2 (2)H14B—C14—H14C109.5
C2—C1—S1122.4 (2)
C10—C9—C8—C131.0 (4)N1—S1—C1—C267.4 (2)
C10—C9—C8—C7178.0 (2)C14—O4—C11—C101.0 (5)
C9—C8—C7—O3165.9 (3)C14—O4—C11—C12179.3 (3)
C13—C8—C7—O311.1 (4)C9—C10—C11—O4178.5 (3)
C9—C8—C7—N112.8 (3)C9—C10—C11—C121.8 (4)
C13—C8—C7—N1170.2 (2)C6—C1—C2—C31.1 (4)
O3—C7—N1—S112.0 (3)S1—C1—C2—C3174.5 (2)
C8—C7—N1—S1166.74 (17)C6—C1—C2—Cl1179.3 (2)
O2—S1—N1—C747.2 (2)S1—C1—C2—Cl15.1 (3)
O1—S1—N1—C7175.11 (19)C8—C13—C12—C110.9 (5)
C1—S1—N1—C767.9 (2)O4—C11—C12—C13179.3 (3)
C8—C9—C10—C110.8 (4)C10—C11—C12—C130.9 (5)
C9—C8—C13—C121.9 (4)C1—C2—C3—C41.5 (4)
C7—C8—C13—C12179.0 (3)Cl1—C2—C3—C4178.9 (3)
O2—S1—C1—C60.9 (2)C2—C1—C6—C50.8 (4)
O1—S1—C1—C6129.0 (2)S1—C1—C6—C5175.0 (2)
N1—S1—C1—C6116.9 (2)C2—C3—C4—C51.6 (5)
O2—S1—C1—C2176.7 (2)C3—C4—C5—C61.3 (6)
O1—S1—C1—C246.8 (2)C1—C6—C5—C40.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.81 (3)2.09 (3)2.872 (3)172 (3)
C3—H3···O1ii0.932.573.370 (4)144
C9—H9···O2i0.932.483.288 (3)145
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+2, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.81 (3)2.09 (3)2.872 (3)172 (3)
C3—H3···O1ii0.932.573.370 (4)144
C9—H9···O2i0.932.483.288 (3)145
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+2, y1/2, z+1/2.
 

Acknowledgements

The authors acknowledge the IOE X-ray diffractometer facility, University of Mysore, Mysore, for the data collection.

References

First citationBruker (2009). APEX2, SADABS, and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationGowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010a). Acta Cryst. E66, o794.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010b). Acta Cryst. E66, o1466.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSuchetan, P. A., Foro, S. & Gowda, B. T. (2011a). Acta Cryst. E67, o146.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSuchetan, P. A., Foro, S. & Gowda, B. T. (2011b). Acta Cryst. E67, o930.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds