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ISSN: 2056-9890

N-(4-Meth­­oxy­benzo­yl)benzene­sulfon­amide

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, bDepartment of Chemistry, AVK College for Women, Davangere-2, India, cDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore, India, dUniversity College of Science, Tumkur University, Tumkur, 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 19 January 2014; online 22 January 2014)

In the title compound, C14H13NO4S, the dihedral angle between the aromatic rings is 69.81 (1)°; the dihedral angle between the planes defined by the S—N—C=O segment of the central chain and the sulfonyl benzene ring is 74.91 (1)°. In the crystal, the mol­ecules are linked by weak N—H⋯O hydrogen bonds into C(4) chains running along [100]. The mol­ecules in adjacent chains are linked by weak C—H⋯O inter­actions, generating R22 (16) dimeric pairs. Weak C—H⋯π inter­actions connect the double chains into (001) sheets.

Related literature

For similar structures, see: Gowda et al. (2009[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516.]); Suchetan et al. (2009[Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2009). Acta Cryst. E65, o3156.], 2010[Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o1772.]); 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.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13NO4S

  • Mr = 291.31

  • Triclinic, [P \overline 1]

  • a = 5.3059 (5) Å

  • b = 10.6343 (10) Å

  • c = 11.9139 (11) Å

  • α = 89.792 (3)°

  • β = 87.392 (3)°

  • γ = 83.944 (3)°

  • V = 667.79 (11) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 2.28 mm−1

  • T = 293 K

  • 0.37 × 0.26 × 0.20 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.515, Tmax = 0.633

  • 8561 measured reflections

  • 2168 independent reflections

  • 2076 reflections with I > 2σ(I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.158

  • S = 1.13

  • 2168 reflections

  • 186 parameters

  • 1 restraint

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

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.84 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the meth­oxy­benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—HN1⋯O1i 0.83 (3) 2.41 (3) 3.1662 (3) 153
C12—H12⋯O2ii 0.93 2.58 3.286 (3) 133
C4—H4⋯Cgiii 0.93 2.90 3.7396 150
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y+1, -z+1; (iii) x, y-1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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 (Suchetan et al., 2009, 2010; Sreenivasa et al., 2013; Gowda et al., 2009), 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, benzene­sulfonamide 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: 399 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 restained to N—H = 0.86 (4) Å. 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 aromatic rings is 69.81 (1)°. Compared to this, the dihedral angle is 80.3 (1)° in N-(benzoyl)-benzene­sulfonamide (II) (Gowda et al., 2009), 68.6 (1)° in N-(4-chloro­benzoyl)-benzene­sulfonamide (III) (Suchetan et al., 2009), 71.9 (1)° in N-(4-methyl­benzoyl)-benzene­sulfonamide (IV) (Suchetan et al., 2010) and 78.62 (16)° in N-(4-meth­oxy­benzoyl)-4-methyl­benzene­sulfonamide (V) (Sreenivasa et al., 2013). This shows that introducing a substituent into the para position of the benzoyl ring correlates with a decrease 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 74.91 (1)°.

In the crystal, both strong classical N—H···O hydrogen bonds and weaker C—H···O and C—H···Cg inter­actions are observed. The molecules are linked to one another through strong N1—HN1···O1 hydrogen bonds into C(4) chains running along [100]. The molecules in the adjacent chains are linked through weak C12—H12···O2 inter­actions, generating R22 (16) dimeric pairs. Combination of the N1—HN1···O1 linked chains and C12—H12···O2 linked dimers form columns along a axis (Figure 2 & 3). The molecules are further connected into C(10) chains running along [010] through C4—H4···Cg inter­actions (Figure 4) resulting in a two dimensional architecture.

Related literature top

For similar structures, see: Gowda et al. (2009); Suchetan et al. (2009, 2010); Sreenivasa et al. (2013).

Structure description top

As a part of our continued efforts to study the crystal structures of N-(aroyl)-aryl­sulfonamides (Suchetan et al., 2009, 2010; Sreenivasa et al., 2013; Gowda et al., 2009), we report here the crystal structure of the title compound (I) (Fig 1).

In (I), the dihedral angle between the aromatic rings is 69.81 (1)°. Compared to this, the dihedral angle is 80.3 (1)° in N-(benzoyl)-benzene­sulfonamide (II) (Gowda et al., 2009), 68.6 (1)° in N-(4-chloro­benzoyl)-benzene­sulfonamide (III) (Suchetan et al., 2009), 71.9 (1)° in N-(4-methyl­benzoyl)-benzene­sulfonamide (IV) (Suchetan et al., 2010) and 78.62 (16)° in N-(4-meth­oxy­benzoyl)-4-methyl­benzene­sulfonamide (V) (Sreenivasa et al., 2013). This shows that introducing a substituent into the para position of the benzoyl ring correlates with a decrease 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 74.91 (1)°.

In the crystal, both strong classical N—H···O hydrogen bonds and weaker C—H···O and C—H···Cg inter­actions are observed. The molecules are linked to one another through strong N1—HN1···O1 hydrogen bonds into C(4) chains running along [100]. The molecules in the adjacent chains are linked through weak C12—H12···O2 inter­actions, generating R22 (16) dimeric pairs. Combination of the N1—HN1···O1 linked chains and C12—H12···O2 linked dimers form columns along a axis (Figure 2 & 3). The molecules are further connected into C(10) chains running along [010] through C4—H4···Cg inter­actions (Figure 4) resulting in a two dimensional architecture.

For similar structures, see: Gowda et al. (2009); Suchetan et al. (2009, 2010); Sreenivasa et al. (2013).

Synthesis and crystallization top

The title compound (I) was prepared by refluxing a mixture of 4-meth­oxy­benzoic acid, benzene­sulfonamide 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: 399 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 restained to N—H = 0.86 (4) Å. 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: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (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. Columns generated from the combination of N1—HN1···O1 linked chains and C12—H12···O2 linked dimers in (I) when viewed along a axis. H-atoms not involved in H-bonds are omitted for clarity purpose.
[Figure 3] Fig. 3. Columns generated from the combination of N1—HN1···O1 linked chains and C12—H12···O2 linked dimers in (I) when viewed down a axis. H-atoms not involved in H-bonds are omitted for clarity purpose.
[Figure 4] Fig. 4. C4—H4···Cg interaction observed in the structure of (I). Cg is the centroid of the methoxyphenyl ring.
N-(4-Methoxybenzoyl)benzenesulfonamide top
Crystal data top
C14H13NO4SF(000) = 304
Mr = 291.31Prism
Triclinic, P1Dx = 1.449 Mg m3
Hall symbol: -P 1Melting point: 399 K
a = 5.3059 (5) ÅCu Kα radiation, λ = 1.54178 Å
b = 10.6343 (10) ÅCell parameters from 25 reflections
c = 11.9139 (11) Åθ = 3.7–64.8°
α = 89.792 (3)°µ = 2.28 mm1
β = 87.392 (3)°T = 293 K
γ = 83.944 (3)°Prism, colourless
V = 667.79 (11) Å30.37 × 0.26 × 0.20 mm
Z = 2
Data collection top
Bruker APEXII
diffractometer
2076 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
Graphite monochromatorθmax = 64.8°, θmin = 3.7°
phi and φ scansh = 66
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1212
Tmin = 0.515, Tmax = 0.633l = 1313
8561 measured reflections3 standard reflections every 120 min
2168 independent reflections intensity decay: 1%
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.1013P)2 + 0.1754P]
where P = (Fo2 + 2Fc2)/3
2168 reflections(Δ/σ)max < 0.001
186 parametersΔρmax = 0.33 e Å3
1 restraintΔρmin = 0.84 e Å3
Crystal data top
C14H13NO4Sγ = 83.944 (3)°
Mr = 291.31V = 667.79 (11) Å3
Triclinic, P1Z = 2
a = 5.3059 (5) ÅCu Kα radiation
b = 10.6343 (10) ŵ = 2.28 mm1
c = 11.9139 (11) ÅT = 293 K
α = 89.792 (3)°0.37 × 0.26 × 0.20 mm
β = 87.392 (3)°
Data collection top
Bruker APEXII
diffractometer
2076 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
Rint = 0.049
Tmin = 0.515, Tmax = 0.6333 standard reflections every 120 min
8561 measured reflections intensity decay: 1%
2168 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0681 restraint
wR(F2) = 0.158H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.33 e Å3
2168 reflectionsΔρmin = 0.84 e Å3
186 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
O10.2427 (3)0.36646 (17)0.44504 (16)0.0596 (5)
N10.6766 (4)0.40318 (19)0.36803 (17)0.0478 (5)
O30.4534 (3)0.39943 (16)0.21164 (15)0.0559 (5)
O41.1816 (4)0.81223 (19)0.06023 (17)0.0695 (6)
C130.9563 (4)0.5966 (2)0.26610 (18)0.0421 (5)
H130.98980.57370.33980.051*
C70.6197 (4)0.4435 (2)0.25993 (19)0.0424 (5)
O20.6259 (4)0.30297 (18)0.54898 (15)0.0624 (5)
C90.7269 (6)0.5777 (3)0.1010 (2)0.0609 (7)
H90.60300.54170.06310.073*
C10.5310 (4)0.1655 (2)0.37956 (18)0.0405 (5)
C121.0878 (4)0.6857 (2)0.2130 (2)0.0475 (6)
H121.21010.72270.25120.057*
C80.7732 (4)0.5405 (2)0.21008 (18)0.0402 (5)
C111.0410 (5)0.7213 (2)0.1032 (2)0.0472 (6)
C50.3772 (5)0.0164 (2)0.2584 (2)0.0564 (6)
H50.25790.00480.20890.068*
C30.7531 (5)0.0405 (3)0.3552 (3)0.0649 (8)
H30.88900.09960.37090.078*
C40.5776 (5)0.0707 (2)0.2829 (2)0.0547 (6)
H40.59300.15040.25000.066*
C20.7307 (5)0.0778 (3)0.4055 (2)0.0574 (6)
H20.84870.09790.45620.069*
C141.1590 (10)0.8451 (4)0.0546 (3)0.0986 (13)
H14A1.20920.77200.10050.148*
H14B1.26650.91000.07340.148*
H14C0.98600.87570.06760.148*
C60.3516 (4)0.1360 (2)0.3071 (2)0.0498 (6)
H60.21570.19480.29100.060*
C100.8596 (6)0.6669 (3)0.0467 (2)0.0635 (7)
H100.82670.68990.02700.076*
S10.50162 (10)0.31426 (5)0.44550 (4)0.0452 (3)
HN10.808 (6)0.419 (4)0.397 (3)0.091 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0540 (10)0.0592 (10)0.0642 (11)0.0033 (8)0.0092 (8)0.0138 (8)
N10.0543 (12)0.0501 (11)0.0432 (11)0.0222 (9)0.0093 (9)0.0000 (8)
O30.0563 (10)0.0581 (10)0.0573 (10)0.0197 (8)0.0149 (8)0.0071 (8)
O40.0829 (14)0.0677 (12)0.0582 (12)0.0183 (10)0.0158 (10)0.0140 (9)
C130.0460 (12)0.0463 (11)0.0348 (11)0.0079 (9)0.0035 (9)0.0026 (9)
C70.0460 (12)0.0400 (11)0.0419 (12)0.0065 (9)0.0039 (9)0.0105 (9)
O20.0851 (13)0.0689 (11)0.0385 (9)0.0294 (10)0.0111 (9)0.0024 (8)
C90.0753 (18)0.0729 (17)0.0393 (13)0.0241 (13)0.0155 (12)0.0048 (11)
C10.0383 (11)0.0445 (11)0.0403 (11)0.0142 (8)0.0036 (8)0.0022 (8)
C120.0477 (12)0.0519 (13)0.0445 (12)0.0126 (10)0.0019 (9)0.0006 (10)
C80.0427 (11)0.0417 (11)0.0361 (11)0.0047 (9)0.0001 (9)0.0081 (8)
C110.0523 (13)0.0460 (12)0.0418 (12)0.0035 (10)0.0118 (10)0.0010 (9)
C50.0568 (14)0.0537 (14)0.0624 (16)0.0215 (11)0.0058 (11)0.0110 (11)
C30.0542 (15)0.0558 (15)0.083 (2)0.0029 (12)0.0004 (14)0.0073 (13)
C40.0572 (14)0.0445 (12)0.0628 (16)0.0153 (10)0.0159 (12)0.0095 (10)
C20.0450 (13)0.0652 (15)0.0628 (15)0.0071 (11)0.0084 (11)0.0083 (12)
C140.147 (4)0.091 (2)0.0561 (19)0.018 (2)0.032 (2)0.0156 (17)
C60.0449 (12)0.0469 (12)0.0598 (14)0.0128 (9)0.0081 (10)0.0050 (10)
C100.084 (2)0.0740 (17)0.0338 (12)0.0134 (14)0.0043 (12)0.0032 (11)
S10.0516 (4)0.0468 (4)0.0393 (4)0.0156 (3)0.0011 (3)0.0074 (2)
Geometric parameters (Å, º) top
O1—S11.4264 (19)C1—S11.758 (2)
N1—C71.392 (3)C12—C111.387 (3)
N1—S11.646 (2)C12—H120.9300
N1—HN10.82 (3)C11—C101.376 (4)
O3—C71.211 (3)C5—C41.376 (4)
O4—C111.367 (3)C5—C61.390 (4)
O4—C141.418 (4)C5—H50.9300
C13—C121.371 (3)C3—C41.360 (4)
C13—C81.389 (3)C3—C21.388 (4)
C13—H130.9300C3—H30.9300
C7—C81.486 (3)C4—H40.9300
O2—S11.4232 (19)C2—H20.9300
C9—C101.381 (4)C14—H14A0.9600
C9—C81.382 (3)C14—H14B0.9600
C9—H90.9300C14—H14C0.9600
C1—C61.375 (3)C6—H60.9300
C1—C21.381 (4)C10—H100.9300
C7—N1—S1123.91 (17)C4—C3—C2120.4 (2)
C7—N1—HN1122 (3)C4—C3—H3119.8
S1—N1—HN1114 (3)C2—C3—H3119.8
C11—O4—C14118.2 (3)C3—C4—C5120.2 (2)
C12—C13—C8120.1 (2)C3—C4—H4119.9
C12—C13—H13119.9C5—C4—H4119.9
C8—C13—H13119.9C1—C2—C3119.2 (2)
O3—C7—N1120.0 (2)C1—C2—H2120.4
O3—C7—C8123.6 (2)C3—C2—H2120.4
N1—C7—C8116.42 (19)O4—C14—H14A109.5
C10—C9—C8121.9 (2)O4—C14—H14B109.5
C10—C9—H9119.1H14A—C14—H14B109.5
C8—C9—H9119.1O4—C14—H14C109.5
C6—C1—C2121.0 (2)H14A—C14—H14C109.5
C6—C1—S1120.16 (18)H14B—C14—H14C109.5
C2—C1—S1118.81 (18)C1—C6—C5118.7 (2)
C13—C12—C11120.9 (2)C1—C6—H6120.6
C13—C12—H12119.5C5—C6—H6120.6
C11—C12—H12119.5C11—C10—C9119.1 (2)
C9—C8—C13118.3 (2)C11—C10—H10120.4
C9—C8—C7117.3 (2)C9—C10—H10120.4
C13—C8—C7124.4 (2)O2—S1—O1119.44 (12)
O4—C11—C10125.0 (2)O2—S1—N1103.74 (11)
O4—C11—C12115.3 (2)O1—S1—N1109.21 (11)
C10—C11—C12119.6 (2)O2—S1—C1108.88 (11)
C4—C5—C6120.5 (2)O1—S1—C1108.65 (10)
C4—C5—H5119.7N1—S1—C1106.11 (10)
C6—C5—H5119.7
S1—N1—C7—O310.3 (3)S1—C1—C2—C3179.0 (2)
S1—N1—C7—C8169.94 (15)C4—C3—C2—C11.4 (4)
C8—C13—C12—C110.0 (3)C2—C1—C6—C51.2 (4)
C10—C9—C8—C131.0 (4)S1—C1—C6—C5178.49 (18)
C10—C9—C8—C7179.8 (2)C4—C5—C6—C10.4 (4)
C12—C13—C8—C90.6 (3)O4—C11—C10—C9178.6 (2)
C12—C13—C8—C7179.8 (2)C12—C11—C10—C90.1 (4)
O3—C7—C8—C92.4 (3)C8—C9—C10—C110.7 (4)
N1—C7—C8—C9177.3 (2)C7—N1—S1—O2177.30 (19)
O3—C7—C8—C13176.8 (2)C7—N1—S1—O148.9 (2)
N1—C7—C8—C133.5 (3)C7—N1—S1—C168.0 (2)
C14—O4—C11—C106.6 (4)C6—C1—S1—O2153.0 (2)
C14—O4—C11—C12174.7 (3)C2—C1—S1—O224.3 (2)
C13—C12—C11—O4179.0 (2)C6—C1—S1—O121.4 (2)
C13—C12—C11—C100.2 (4)C2—C1—S1—O1155.9 (2)
C2—C3—C4—C50.6 (4)C6—C1—S1—N195.9 (2)
C6—C5—C4—C30.1 (4)C2—C1—S1—N186.8 (2)
C6—C1—C2—C31.7 (4)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the methoxybenzene ring.
D—H···AD—HH···AD···AD—H···A
N1—HN1···O1i0.83 (3)2.41 (3)3.1662 (3)153
C12—H12···O2ii0.932.583.286 (3)133
C4—H4···Cgiii0.932.903.7396150
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+1, z+1; (iii) x, y1, z.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the methoxybenzene ring.
D—H···AD—HH···AD···AD—H···A
N1—HN1···O1i0.83 (3)2.41 (3)3.1662 (3)153
C12—H12···O2ii0.932.583.286 (3)133
C4—H4···Cgiii0.932.903.7396150
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+1, z+1; (iii) x, y1, z.
 

Acknowledgements

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

References

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