organic compounds
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
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 π–π stacking interaction is also observed [centroid–centroid separation = 3.7305 (3) Å].
CCDC reference: 978143
Related literature
For related structures, see: Gowda et al. (2010); Suchetan et al. (2010a,b, 2011); Sreenivasa et al. (2013, 2014).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus; 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.
Supporting information
CCDC reference: 978143
10.1107/S1600536814001354/hb7188sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001354/hb7188Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001354/hb7188Isup3.cml
As a part of our continued efforts to study the crystal structures of N-(aroyl)-arylsulfonamides (Sreenivasa et al., 2014), we report here the
of the title compound (I) (Fig 1).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.
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).
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
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 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.
As a part of our continued efforts to study the crystal structures of N-(aroyl)-arylsulfonamides (Sreenivasa et al., 2014), we report here the
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
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 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).
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.
detailsThe 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).
Data collection: APEX2 (Bruker, 2009); cell
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).C15H15NO4S | Prism |
Mr = 305.34 | Dx = 1.387 Mg m−3 |
Monoclinic, C2/c | Melting point: 447 K |
Hall symbol: -C 2yc | Cu Kα radiation, λ = 1.54178 Å |
a = 21.807 (2) Å | Cell parameters from 25 reflections |
b = 7.3521 (8) Å | θ = 4.1–64.7° |
c = 18.602 (2) Å | µ = 2.11 mm−1 |
β = 101.211 (3)° | T = 293 K |
V = 2925.4 (5) Å3 | Prism, colourless |
Z = 8 | 0.38 × 0.29 × 0.22 mm |
F(000) = 1280 |
Bruker APEXII CCD diffractometer | 2431 independent reflections |
Radiation source: fine-focus sealed tube | 2174 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
phi and φ scans | θmax = 64.7°, θmin = 4.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −25→24 |
Tmin = 0.504, Tmax = 0.629 | k = −7→8 |
16411 measured reflections | l = −20→21 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H 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 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.51 e Å−3 |
C15H15NO4S | V = 2925.4 (5) Å3 |
Mr = 305.34 | Z = 8 |
Monoclinic, C2/c | Cu Kα radiation |
a = 21.807 (2) Å | µ = 2.11 mm−1 |
b = 7.3521 (8) Å | T = 293 K |
c = 18.602 (2) Å | 0.38 × 0.29 × 0.22 mm |
β = 101.211 (3)° |
Bruker APEXII CCD diffractometer | 2431 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2174 reflections with I > 2σ(I) |
Tmin = 0.504, Tmax = 0.629 | Rint = 0.060 |
16411 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.92 | Δρmax = 0.34 e Å−3 |
2431 reflections | Δρmin = −0.51 e Å−3 |
196 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
H1 | 0.0708 (12) | 0.197 (3) | 0.2813 (15) | 0.051 (7)* | |
S1 | 0.02647 (2) | 0.20056 (7) | 0.37394 (2) | 0.0326 (2) | |
O2 | −0.02356 (6) | 0.2872 (2) | 0.32370 (7) | 0.0408 (4) | |
O1 | 0.01308 (8) | 0.0360 (2) | 0.40868 (8) | 0.0499 (4) | |
O3 | 0.15501 (7) | 0.0483 (2) | 0.41305 (7) | 0.0464 (4) | |
C8 | 0.17364 (9) | 0.0372 (3) | 0.29109 (9) | 0.0335 (4) | |
N1 | 0.07872 (7) | 0.1589 (2) | 0.32300 (8) | 0.0346 (4) | |
O4 | 0.28653 (7) | −0.0475 (2) | 0.13921 (8) | 0.0512 (4) | |
C13 | 0.14633 (9) | 0.0201 (3) | 0.21740 (10) | 0.0395 (5) | |
H13 | 0.1031 | 0.0286 | 0.2031 | 0.047* | |
C6 | 0.07042 (10) | 0.2955 (3) | 0.51353 (10) | 0.0406 (5) | |
H6 | 0.0606 | 0.1764 | 0.5238 | 0.049* | |
C12 | 0.18241 (10) | −0.0093 (3) | 0.16511 (10) | 0.0399 (5) | |
H12 | 0.1636 | −0.0204 | 0.1160 | 0.048* | |
C2 | 0.07397 (9) | 0.5358 (3) | 0.42381 (10) | 0.0372 (5) | |
C1 | 0.06024 (8) | 0.3584 (3) | 0.44137 (9) | 0.0317 (4) | |
C7 | 0.13675 (9) | 0.0789 (3) | 0.34846 (9) | 0.0341 (4) | |
C11 | 0.24672 (10) | −0.0224 (3) | 0.18620 (10) | 0.0372 (5) | |
C10 | 0.27437 (10) | −0.0116 (3) | 0.26017 (10) | 0.0439 (5) | |
H10 | 0.3175 | −0.0233 | 0.2746 | 0.053* | |
C3 | 0.09891 (10) | 0.6503 (3) | 0.48231 (12) | 0.0476 (5) | |
H3 | 0.1087 | 0.7699 | 0.4729 | 0.057* | |
C4 | 0.10915 (10) | 0.5888 (3) | 0.55374 (11) | 0.0488 (6) | |
H4 | 0.1257 | 0.6677 | 0.5917 | 0.059* | |
C9 | 0.23797 (10) | 0.0164 (3) | 0.31184 (10) | 0.0402 (5) | |
H9 | 0.2566 | 0.0214 | 0.3612 | 0.048* | |
C5 | 0.09543 (11) | 0.4140 (4) | 0.56954 (10) | 0.0484 (6) | |
H5 | 0.1029 | 0.3744 | 0.6179 | 0.058* | |
C14 | 0.06366 (13) | 0.6127 (3) | 0.34685 (11) | 0.0543 (6) | |
H14A | 0.0891 | 0.5479 | 0.3188 | 0.082* | |
H14B | 0.0749 | 0.7392 | 0.3489 | 0.082* | |
H14C | 0.0204 | 0.5999 | 0.3240 | 0.082* | |
C15 | 0.25999 (13) | −0.0489 (5) | 0.06265 (12) | 0.0653 (8) | |
H15A | 0.2278 | −0.1398 | 0.0529 | 0.098* | |
H15B | 0.2920 | −0.0762 | 0.0354 | 0.098* | |
H15C | 0.2423 | 0.0682 | 0.0483 | 0.098* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0365 (3) | 0.0348 (3) | 0.0268 (3) | −0.00716 (18) | 0.00702 (19) | −0.00524 (15) |
O2 | 0.0324 (7) | 0.0554 (10) | 0.0325 (6) | 0.0007 (6) | 0.0010 (5) | −0.0104 (6) |
O1 | 0.0681 (10) | 0.0406 (10) | 0.0444 (8) | −0.0208 (8) | 0.0191 (7) | −0.0039 (6) |
O3 | 0.0543 (9) | 0.0550 (10) | 0.0273 (7) | 0.0034 (7) | 0.0017 (6) | 0.0049 (6) |
C8 | 0.0386 (10) | 0.0296 (11) | 0.0303 (9) | 0.0028 (8) | 0.0019 (7) | −0.0019 (7) |
N1 | 0.0392 (9) | 0.0399 (10) | 0.0253 (7) | 0.0049 (7) | 0.0074 (6) | 0.0007 (6) |
O4 | 0.0439 (8) | 0.0725 (12) | 0.0379 (7) | 0.0054 (8) | 0.0095 (6) | −0.0081 (7) |
C13 | 0.0351 (10) | 0.0450 (13) | 0.0345 (10) | 0.0073 (9) | −0.0032 (8) | −0.0057 (8) |
C6 | 0.0489 (11) | 0.0422 (13) | 0.0307 (9) | −0.0017 (9) | 0.0075 (8) | −0.0004 (8) |
C12 | 0.0430 (11) | 0.0445 (12) | 0.0287 (9) | 0.0080 (9) | −0.0013 (7) | −0.0074 (8) |
C2 | 0.0403 (10) | 0.0341 (12) | 0.0357 (9) | 0.0005 (9) | 0.0034 (7) | −0.0032 (8) |
C1 | 0.0326 (9) | 0.0352 (11) | 0.0266 (8) | −0.0011 (8) | 0.0046 (6) | −0.0040 (7) |
C7 | 0.0403 (10) | 0.0304 (11) | 0.0302 (9) | −0.0022 (8) | 0.0035 (7) | −0.0012 (7) |
C11 | 0.0396 (10) | 0.0358 (12) | 0.0356 (9) | 0.0046 (8) | 0.0059 (8) | −0.0039 (7) |
C10 | 0.0332 (10) | 0.0562 (15) | 0.0388 (10) | 0.0049 (9) | −0.0020 (8) | −0.0069 (9) |
C3 | 0.0514 (12) | 0.0351 (12) | 0.0534 (12) | −0.0048 (10) | 0.0030 (9) | −0.0116 (9) |
C4 | 0.0499 (12) | 0.0511 (15) | 0.0420 (11) | −0.0006 (11) | 0.0004 (9) | −0.0205 (9) |
C9 | 0.0414 (11) | 0.0449 (13) | 0.0301 (9) | 0.0061 (9) | −0.0039 (7) | −0.0031 (8) |
C5 | 0.0545 (12) | 0.0619 (16) | 0.0267 (9) | 0.0014 (11) | 0.0027 (8) | −0.0083 (9) |
C14 | 0.0776 (16) | 0.0396 (14) | 0.0432 (11) | −0.0074 (12) | 0.0051 (10) | 0.0074 (9) |
C15 | 0.0629 (15) | 0.099 (2) | 0.0353 (11) | 0.0046 (15) | 0.0129 (10) | −0.0059 (11) |
S1—O1 | 1.4283 (15) | C2—C1 | 1.391 (3) |
S1—O2 | 1.4398 (14) | C2—C3 | 1.399 (3) |
S1—N1 | 1.6461 (16) | C2—C14 | 1.515 (3) |
S1—C1 | 1.7613 (18) | C11—C10 | 1.393 (3) |
O3—C7 | 1.211 (2) | C10—C9 | 1.376 (3) |
C8—C13 | 1.390 (2) | C10—H10 | 0.9300 |
C8—C9 | 1.389 (3) | C3—C4 | 1.380 (3) |
C8—C7 | 1.488 (3) | C3—H3 | 0.9300 |
N1—C7 | 1.392 (2) | C4—C5 | 1.364 (4) |
N1—H1 | 0.81 (3) | C4—H4 | 0.9300 |
O4—C11 | 1.359 (2) | C9—H9 | 0.9300 |
O4—C15 | 1.429 (3) | C5—H5 | 0.9300 |
C13—C12 | 1.382 (3) | C14—H14A | 0.9600 |
C13—H13 | 0.9300 | C14—H14B | 0.9600 |
C6—C5 | 1.386 (3) | C14—H14C | 0.9600 |
C6—C1 | 1.396 (3) | C15—H15A | 0.9600 |
C6—H6 | 0.9300 | C15—H15B | 0.9600 |
C12—C11 | 1.384 (3) | C15—H15C | 0.9600 |
C12—H12 | 0.9300 | ||
O1—S1—O2 | 118.20 (10) | O4—C11—C12 | 124.46 (17) |
O1—S1—N1 | 109.14 (9) | O4—C11—C10 | 115.78 (18) |
O2—S1—N1 | 103.34 (8) | C12—C11—C10 | 119.75 (18) |
O1—S1—C1 | 109.25 (9) | C9—C10—C11 | 120.05 (19) |
O2—S1—C1 | 109.27 (9) | C9—C10—H10 | 120.0 |
N1—S1—C1 | 107.00 (8) | C11—C10—H10 | 120.0 |
C13—C8—C9 | 118.68 (18) | C4—C3—C2 | 121.2 (2) |
C13—C8—C7 | 122.57 (18) | C4—C3—H3 | 119.4 |
C9—C8—C7 | 118.75 (16) | C2—C3—H3 | 119.4 |
C7—N1—S1 | 124.60 (13) | C5—C4—C3 | 120.98 (19) |
C7—N1—H1 | 118.8 (19) | C5—C4—H4 | 119.5 |
S1—N1—H1 | 116.3 (19) | C3—C4—H4 | 119.5 |
C11—O4—C15 | 117.14 (17) | C10—C9—C8 | 120.73 (17) |
C12—C13—C8 | 121.00 (18) | C10—C9—H9 | 119.6 |
C12—C13—H13 | 119.5 | C8—C9—H9 | 119.6 |
C8—C13—H13 | 119.5 | C4—C5—C6 | 120.05 (19) |
C5—C6—C1 | 118.7 (2) | C4—C5—H5 | 120.0 |
C5—C6—H6 | 120.6 | C6—C5—H5 | 120.0 |
C1—C6—H6 | 120.6 | C2—C14—H14A | 109.5 |
C13—C12—C11 | 119.69 (17) | C2—C14—H14B | 109.5 |
C13—C12—H12 | 120.2 | H14A—C14—H14B | 109.5 |
C11—C12—H12 | 120.2 | C2—C14—H14C | 109.5 |
C1—C2—C3 | 116.76 (18) | H14A—C14—H14C | 109.5 |
C1—C2—C14 | 124.95 (17) | H14B—C14—H14C | 109.5 |
C3—C2—C14 | 118.3 (2) | O4—C15—H15A | 109.5 |
C2—C1—C6 | 122.33 (17) | O4—C15—H15B | 109.5 |
C2—C1—S1 | 121.98 (13) | H15A—C15—H15B | 109.5 |
C6—C1—S1 | 115.67 (16) | O4—C15—H15C | 109.5 |
O3—C7—N1 | 121.18 (17) | H15A—C15—H15C | 109.5 |
O3—C7—C8 | 123.64 (18) | H15B—C15—H15C | 109.5 |
N1—C7—C8 | 115.18 (15) | ||
O1—S1—N1—C7 | −55.03 (19) | S1—N1—C7—C8 | 174.04 (14) |
O2—S1—N1—C7 | 178.35 (16) | C13—C8—C7—O3 | 159.9 (2) |
C1—S1—N1—C7 | 63.07 (19) | C9—C8—C7—O3 | −20.8 (3) |
C9—C8—C13—C12 | −2.7 (3) | C13—C8—C7—N1 | −20.8 (3) |
C7—C8—C13—C12 | 176.6 (2) | C9—C8—C7—N1 | 158.54 (19) |
C8—C13—C12—C11 | 0.1 (3) | C15—O4—C11—C12 | 4.1 (3) |
C3—C2—C1—C6 | 0.1 (3) | C15—O4—C11—C10 | −176.6 (2) |
C14—C2—C1—C6 | −179.6 (2) | C13—C12—C11—O4 | −178.6 (2) |
C3—C2—C1—S1 | 178.06 (16) | C13—C12—C11—C10 | 2.1 (3) |
C14—C2—C1—S1 | −1.6 (3) | O4—C11—C10—C9 | 179.1 (2) |
C5—C6—C1—C2 | −0.4 (3) | C12—C11—C10—C9 | −1.6 (4) |
C5—C6—C1—S1 | −178.41 (16) | C1—C2—C3—C4 | 0.0 (3) |
O1—S1—C1—C2 | −175.20 (16) | C14—C2—C3—C4 | 179.7 (2) |
O2—S1—C1—C2 | −44.48 (18) | C2—C3—C4—C5 | 0.2 (4) |
N1—S1—C1—C2 | 66.76 (18) | C11—C10—C9—C8 | −1.1 (4) |
O1—S1—C1—C6 | 2.85 (18) | C13—C8—C9—C10 | 3.2 (3) |
O2—S1—C1—C6 | 133.58 (15) | C7—C8—C9—C10 | −176.1 (2) |
N1—S1—C1—C6 | −115.18 (16) | C3—C4—C5—C6 | −0.4 (3) |
S1—N1—C7—O3 | −6.6 (3) | C1—C6—C5—C4 | 0.5 (3) |
D—H···A | D—H | H···A | D···A | 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+1/2. |
D—H···A | D—H | H···A | D···A | 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+1/2. |
Acknowledgements
The authors acknowledge the IOE X-ray diffractometer facility, University of Mysore, Mysore, for the data collection.
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