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COMMUNICATIONS
ISSN: 2056-9890

N-(4-Meth­­oxy­benzo­yl)-2-methyl­benzene­sulfonamide

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 Physics, University of Mysore, Manasagangotri, Mysore, India, and dDepartment 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 20 January 2014; online 22 January 2014)

In the title compound, C15H15NO4S, the dihedral angle between the aromatic rings is 80.81 (1)° and the dihedral angle between the planes defined by the S—N—C=O fragment and the sulfonyl benzene ring is 86.34 (1)°. In the extended structure, dimers related by a crystallographic twofold axis are connected by pairs of both N—H⋯O hydrogen bonds and C—H⋯O inter­actions, which generate R22(8) and R22(14) loops, respectively. A weak aromatic ππ stacking inter­action is also observed [centroid–centroid separation = 3.7305 (3) Å].

Related literature

For related structures, see: Gowda et al. (2010[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o747.]); Suchetan et al. (2010a[Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010a). Acta Cryst. E66, o1024.],b[Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010b). Acta Cryst. E66, o1997.], 2011[Suchetan, P. A., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o929.]); Sreenivasa et al. (2013[Sreenivasa, S., Palakshamurthy, B. S., Tonannavar, J., Jayashree, Y., Sudha, A. G. & Suchetan, P. A. (2013). Acta Cryst. E69, o1664-o1665.], 2014[Sreenivasa, S., Nanjundaswamy, M. S., Madankumar, S., Lokanath, N. K., Suresha, E. & Suchetan, P. A. (2014). Acta Cryst. E70, o192.]).

[Scheme 1]

Experimental

Crystal data
  • C15H15NO4S

  • Mr = 305.34

  • Monoclinic, C 2/c

  • a = 21.807 (2) Å

  • b = 7.3521 (8) Å

  • c = 18.602 (2) Å

  • β = 101.211 (3)°

  • V = 2925.4 (5) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 2.11 mm−1

  • T = 293 K

  • 0.38 × 0.29 × 0.22 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 = 0.504, Tmax = 0.629

  • 16411 measured reflections

  • 2431 independent reflections

  • 2174 reflections with I > 2σ(I)

  • Rint = 0.060

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.122

  • S = 0.92

  • 2431 reflections

  • 196 parameters

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

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.51 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) 2.16 (3) 2.917 (2) 164 (3)
C13—H13⋯O2i 0.93 2.56 3.288 (3) 136
Symmetry code: (i) [-x, y, -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 efforts to study the crystal structures of N-(aroyl)-aryl­sulfonamides (Sreenivasa et al., 2014), 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-methyl­benzene­sulfonamide 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: 447 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 80.81 (1)°. Compared to this, the dihedral angle is 73.9 (1)° in N-(benzoyl)-2-methyl­benzene­sulfonamide (II, Suchetan et al., 2010a), 89.4 (1)° and 82.4 (1)° respectively in the two molecules in the asymmetric unit of N-(4-chloro­benzoyl)-2-methyl­benzene­sulfonamide (III, Suchetan et al., 2010b), 88.1 (1)° and 83.5 (1)° respectively in the two molecules in the asymmetric unit of N-(4-methyl­benzoyl)-2-methyl­benzene­sulfonamide (IV, Gowda et al., 2010) and 83.8 (2)° in N-(4-nitro­benzoyl)-2-methyl­benzene­sulfonamide (V, Suchetan et al., 2011). 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. In contrast to this, the dihedral angle is small in N-(4-meth­oxy-benzoyl)-benzene­sulfonamide (VI, Sreenivasa et al., 2014) and N-(4-meth­oxy­benzoyl)-4-methyl­benzene­sulfonamide (VII, Sreenivasa et al., 2013), the dihedral angle being respectively 69.81 (1)° and 78.62 (16)° in VI and VII. 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 86.34 (1)°.

The supra­molecular architecture of I is built in three stages. In the first stage, the molecules are linked into dimers by a crystallographic twofold axis through strong N1—H1···O2 hydrogen bonds, thus generating R22(8) rings (Figure 2). These dimers in the second stage are linked through an additional C13—H13···O2 inter­action (Figure 2) forming R22(14) ring motif. In the third stage, π(methyl­phenyl) ···π(methyl­phenyl) inter­actions stabilize the structure, Cg(methyl­phenyl) ···Cg(methyl­phenyl) distance being 3.7305 (3)Å (Figure 3). The geometries and symmetry operations of various inter­actions are shown in Table 1.

Related literature top

For related structures, see: Gowda et al. (2010); Suchetan et al. (2010a,b, 2011); Sreenivasa et al. (2013, 2014).

Structure description top

As a part of our continued efforts to study the crystal structures of N-(aroyl)-aryl­sulfonamides (Sreenivasa et al., 2014), we report here the crystal structure of the title compound (I) (Fig 1).

In I, the dihedral angle between the two aromatic rings is 80.81 (1)°. Compared to this, the dihedral angle is 73.9 (1)° in N-(benzoyl)-2-methyl­benzene­sulfonamide (II, Suchetan et al., 2010a), 89.4 (1)° and 82.4 (1)° respectively in the two molecules in the asymmetric unit of N-(4-chloro­benzoyl)-2-methyl­benzene­sulfonamide (III, Suchetan et al., 2010b), 88.1 (1)° and 83.5 (1)° respectively in the two molecules in the asymmetric unit of N-(4-methyl­benzoyl)-2-methyl­benzene­sulfonamide (IV, Gowda et al., 2010) and 83.8 (2)° in N-(4-nitro­benzoyl)-2-methyl­benzene­sulfonamide (V, Suchetan et al., 2011). 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. In contrast to this, the dihedral angle is small in N-(4-meth­oxy-benzoyl)-benzene­sulfonamide (VI, Sreenivasa et al., 2014) and N-(4-meth­oxy­benzoyl)-4-methyl­benzene­sulfonamide (VII, Sreenivasa et al., 2013), the dihedral angle being respectively 69.81 (1)° and 78.62 (16)° in VI and VII. 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 86.34 (1)°.

The supra­molecular architecture of I is built in three stages. In the first stage, the molecules are linked into dimers by a crystallographic twofold axis through strong N1—H1···O2 hydrogen bonds, thus generating R22(8) rings (Figure 2). These dimers in the second stage are linked through an additional C13—H13···O2 inter­action (Figure 2) forming R22(14) ring motif. In the third stage, π(methyl­phenyl) ···π(methyl­phenyl) inter­actions stabilize the structure, Cg(methyl­phenyl) ···Cg(methyl­phenyl) distance being 3.7305 (3)Å (Figure 3). The geometries and symmetry operations of various inter­actions are shown in Table 1.

For related structures, see: Gowda et al. (2010); Suchetan et al. (2010a,b, 2011); Sreenivasa et al. (2013, 2014).

Synthesis and crystallization top

The title compound (I) was prepared by refluxing a mixture of 4-meth­oxy­benzoic acid, 2-methyl­benzene­sulfonamide 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: 447 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 R22(8) and R22(14) rings in I.
[Figure 3] Fig. 3. π···π interaction observed in the crystal structure. Cg is the centroid of the methylphenyl ring.
N-(4-Methoxybenzoyl)-2-methylbenzenesulfonamide top
Crystal data top
C15H15NO4SPrism
Mr = 305.34Dx = 1.387 Mg m3
Monoclinic, C2/cMelting point: 447 K
Hall symbol: -C 2ycCu Kα radiation, λ = 1.54178 Å
a = 21.807 (2) ÅCell parameters from 25 reflections
b = 7.3521 (8) Åθ = 4.1–64.7°
c = 18.602 (2) ŵ = 2.11 mm1
β = 101.211 (3)°T = 293 K
V = 2925.4 (5) Å3Prism, colourless
Z = 80.38 × 0.29 × 0.22 mm
F(000) = 1280
Data collection top
Bruker APEXII CCD
diffractometer
2431 independent reflections
Radiation source: fine-focus sealed tube2174 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
phi and φ scansθmax = 64.7°, θmin = 4.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 2524
Tmin = 0.504, Tmax = 0.629k = 78
16411 measured reflectionsl = 2021
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 0.92 w = 1/[σ2(Fo2) + (0.0923P)2 + 2.3453P]
where P = (Fo2 + 2Fc2)/3
2431 reflections(Δ/σ)max < 0.001
196 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.51 e Å3
Crystal data top
C15H15NO4SV = 2925.4 (5) Å3
Mr = 305.34Z = 8
Monoclinic, C2/cCu Kα radiation
a = 21.807 (2) ŵ = 2.11 mm1
b = 7.3521 (8) ÅT = 293 K
c = 18.602 (2) Å0.38 × 0.29 × 0.22 mm
β = 101.211 (3)°
Data collection top
Bruker APEXII CCD
diffractometer
2431 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2174 reflections with I > 2σ(I)
Tmin = 0.504, Tmax = 0.629Rint = 0.060
16411 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 0.92Δρmax = 0.34 e Å3
2431 reflectionsΔρmin = 0.51 e Å3
196 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
H10.0708 (12)0.197 (3)0.2813 (15)0.051 (7)*
S10.02647 (2)0.20056 (7)0.37394 (2)0.0326 (2)
O20.02356 (6)0.2872 (2)0.32370 (7)0.0408 (4)
O10.01308 (8)0.0360 (2)0.40868 (8)0.0499 (4)
O30.15501 (7)0.0483 (2)0.41305 (7)0.0464 (4)
C80.17364 (9)0.0372 (3)0.29109 (9)0.0335 (4)
N10.07872 (7)0.1589 (2)0.32300 (8)0.0346 (4)
O40.28653 (7)0.0475 (2)0.13921 (8)0.0512 (4)
C130.14633 (9)0.0201 (3)0.21740 (10)0.0395 (5)
H130.10310.02860.20310.047*
C60.07042 (10)0.2955 (3)0.51353 (10)0.0406 (5)
H60.06060.17640.52380.049*
C120.18241 (10)0.0093 (3)0.16511 (10)0.0399 (5)
H120.16360.02040.11600.048*
C20.07397 (9)0.5358 (3)0.42381 (10)0.0372 (5)
C10.06024 (8)0.3584 (3)0.44137 (9)0.0317 (4)
C70.13675 (9)0.0789 (3)0.34846 (9)0.0341 (4)
C110.24672 (10)0.0224 (3)0.18620 (10)0.0372 (5)
C100.27437 (10)0.0116 (3)0.26017 (10)0.0439 (5)
H100.31750.02330.27460.053*
C30.09891 (10)0.6503 (3)0.48231 (12)0.0476 (5)
H30.10870.76990.47290.057*
C40.10915 (10)0.5888 (3)0.55374 (11)0.0488 (6)
H40.12570.66770.59170.059*
C90.23797 (10)0.0164 (3)0.31184 (10)0.0402 (5)
H90.25660.02140.36120.048*
C50.09543 (11)0.4140 (4)0.56954 (10)0.0484 (6)
H50.10290.37440.61790.058*
C140.06366 (13)0.6127 (3)0.34685 (11)0.0543 (6)
H14A0.08910.54790.31880.082*
H14B0.07490.73920.34890.082*
H14C0.02040.59990.32400.082*
C150.25999 (13)0.0489 (5)0.06265 (12)0.0653 (8)
H15A0.22780.13980.05290.098*
H15B0.29200.07620.03540.098*
H15C0.24230.06820.04830.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0365 (3)0.0348 (3)0.0268 (3)0.00716 (18)0.00702 (19)0.00524 (15)
O20.0324 (7)0.0554 (10)0.0325 (6)0.0007 (6)0.0010 (5)0.0104 (6)
O10.0681 (10)0.0406 (10)0.0444 (8)0.0208 (8)0.0191 (7)0.0039 (6)
O30.0543 (9)0.0550 (10)0.0273 (7)0.0034 (7)0.0017 (6)0.0049 (6)
C80.0386 (10)0.0296 (11)0.0303 (9)0.0028 (8)0.0019 (7)0.0019 (7)
N10.0392 (9)0.0399 (10)0.0253 (7)0.0049 (7)0.0074 (6)0.0007 (6)
O40.0439 (8)0.0725 (12)0.0379 (7)0.0054 (8)0.0095 (6)0.0081 (7)
C130.0351 (10)0.0450 (13)0.0345 (10)0.0073 (9)0.0032 (8)0.0057 (8)
C60.0489 (11)0.0422 (13)0.0307 (9)0.0017 (9)0.0075 (8)0.0004 (8)
C120.0430 (11)0.0445 (12)0.0287 (9)0.0080 (9)0.0013 (7)0.0074 (8)
C20.0403 (10)0.0341 (12)0.0357 (9)0.0005 (9)0.0034 (7)0.0032 (8)
C10.0326 (9)0.0352 (11)0.0266 (8)0.0011 (8)0.0046 (6)0.0040 (7)
C70.0403 (10)0.0304 (11)0.0302 (9)0.0022 (8)0.0035 (7)0.0012 (7)
C110.0396 (10)0.0358 (12)0.0356 (9)0.0046 (8)0.0059 (8)0.0039 (7)
C100.0332 (10)0.0562 (15)0.0388 (10)0.0049 (9)0.0020 (8)0.0069 (9)
C30.0514 (12)0.0351 (12)0.0534 (12)0.0048 (10)0.0030 (9)0.0116 (9)
C40.0499 (12)0.0511 (15)0.0420 (11)0.0006 (11)0.0004 (9)0.0205 (9)
C90.0414 (11)0.0449 (13)0.0301 (9)0.0061 (9)0.0039 (7)0.0031 (8)
C50.0545 (12)0.0619 (16)0.0267 (9)0.0014 (11)0.0027 (8)0.0083 (9)
C140.0776 (16)0.0396 (14)0.0432 (11)0.0074 (12)0.0051 (10)0.0074 (9)
C150.0629 (15)0.099 (2)0.0353 (11)0.0046 (15)0.0129 (10)0.0059 (11)
Geometric parameters (Å, º) top
S1—O11.4283 (15)C2—C11.391 (3)
S1—O21.4398 (14)C2—C31.399 (3)
S1—N11.6461 (16)C2—C141.515 (3)
S1—C11.7613 (18)C11—C101.393 (3)
O3—C71.211 (2)C10—C91.376 (3)
C8—C131.390 (2)C10—H100.9300
C8—C91.389 (3)C3—C41.380 (3)
C8—C71.488 (3)C3—H30.9300
N1—C71.392 (2)C4—C51.364 (4)
N1—H10.81 (3)C4—H40.9300
O4—C111.359 (2)C9—H90.9300
O4—C151.429 (3)C5—H50.9300
C13—C121.382 (3)C14—H14A0.9600
C13—H130.9300C14—H14B0.9600
C6—C51.386 (3)C14—H14C0.9600
C6—C11.396 (3)C15—H15A0.9600
C6—H60.9300C15—H15B0.9600
C12—C111.384 (3)C15—H15C0.9600
C12—H120.9300
O1—S1—O2118.20 (10)O4—C11—C12124.46 (17)
O1—S1—N1109.14 (9)O4—C11—C10115.78 (18)
O2—S1—N1103.34 (8)C12—C11—C10119.75 (18)
O1—S1—C1109.25 (9)C9—C10—C11120.05 (19)
O2—S1—C1109.27 (9)C9—C10—H10120.0
N1—S1—C1107.00 (8)C11—C10—H10120.0
C13—C8—C9118.68 (18)C4—C3—C2121.2 (2)
C13—C8—C7122.57 (18)C4—C3—H3119.4
C9—C8—C7118.75 (16)C2—C3—H3119.4
C7—N1—S1124.60 (13)C5—C4—C3120.98 (19)
C7—N1—H1118.8 (19)C5—C4—H4119.5
S1—N1—H1116.3 (19)C3—C4—H4119.5
C11—O4—C15117.14 (17)C10—C9—C8120.73 (17)
C12—C13—C8121.00 (18)C10—C9—H9119.6
C12—C13—H13119.5C8—C9—H9119.6
C8—C13—H13119.5C4—C5—C6120.05 (19)
C5—C6—C1118.7 (2)C4—C5—H5120.0
C5—C6—H6120.6C6—C5—H5120.0
C1—C6—H6120.6C2—C14—H14A109.5
C13—C12—C11119.69 (17)C2—C14—H14B109.5
C13—C12—H12120.2H14A—C14—H14B109.5
C11—C12—H12120.2C2—C14—H14C109.5
C1—C2—C3116.76 (18)H14A—C14—H14C109.5
C1—C2—C14124.95 (17)H14B—C14—H14C109.5
C3—C2—C14118.3 (2)O4—C15—H15A109.5
C2—C1—C6122.33 (17)O4—C15—H15B109.5
C2—C1—S1121.98 (13)H15A—C15—H15B109.5
C6—C1—S1115.67 (16)O4—C15—H15C109.5
O3—C7—N1121.18 (17)H15A—C15—H15C109.5
O3—C7—C8123.64 (18)H15B—C15—H15C109.5
N1—C7—C8115.18 (15)
O1—S1—N1—C755.03 (19)S1—N1—C7—C8174.04 (14)
O2—S1—N1—C7178.35 (16)C13—C8—C7—O3159.9 (2)
C1—S1—N1—C763.07 (19)C9—C8—C7—O320.8 (3)
C9—C8—C13—C122.7 (3)C13—C8—C7—N120.8 (3)
C7—C8—C13—C12176.6 (2)C9—C8—C7—N1158.54 (19)
C8—C13—C12—C110.1 (3)C15—O4—C11—C124.1 (3)
C3—C2—C1—C60.1 (3)C15—O4—C11—C10176.6 (2)
C14—C2—C1—C6179.6 (2)C13—C12—C11—O4178.6 (2)
C3—C2—C1—S1178.06 (16)C13—C12—C11—C102.1 (3)
C14—C2—C1—S11.6 (3)O4—C11—C10—C9179.1 (2)
C5—C6—C1—C20.4 (3)C12—C11—C10—C91.6 (4)
C5—C6—C1—S1178.41 (16)C1—C2—C3—C40.0 (3)
O1—S1—C1—C2175.20 (16)C14—C2—C3—C4179.7 (2)
O2—S1—C1—C244.48 (18)C2—C3—C4—C50.2 (4)
N1—S1—C1—C266.76 (18)C11—C10—C9—C81.1 (4)
O1—S1—C1—C62.85 (18)C13—C8—C9—C103.2 (3)
O2—S1—C1—C6133.58 (15)C7—C8—C9—C10176.1 (2)
N1—S1—C1—C6115.18 (16)C3—C4—C5—C60.4 (3)
S1—N1—C7—O36.6 (3)C1—C6—C5—C40.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.81 (3)2.16 (3)2.917 (2)164 (3)
C13—H13···O2i0.932.563.288 (3)136
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.81 (3)2.16 (3)2.917 (2)164 (3)
C13—H13···O2i0.932.563.288 (3)136
Symmetry code: (i) x, y, 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. (2010). Acta Cryst. E66, o747.  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 citationSreenivasa, S., Nanjundaswamy, M. S., Madankumar, S., Lokanath, N. K., Suresha, E. & Suchetan, P. A. (2014). Acta Cryst. E70, o192.  CSD CrossRef IUCr Journals Google Scholar
First citationSreenivasa, S., Palakshamurthy, B. S., Tonannavar, J., Jayashree, Y., Sudha, A. G. & Suchetan, P. A. (2013). Acta Cryst. E69, o1664–o1665.  CSD CrossRef CAS IUCr Journals Google Scholar
First citationSuchetan, P. A., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o929.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSuchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010a). Acta Cryst. E66, o1024.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSuchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010b). Acta Cryst. E66, o1997.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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