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

Journal logoIUCrDATA
ISSN: 2414-3146

2,5-Dimeth­­oxy-N-phenyl­benzene­sulfonamide

aDepartment of Chemistry, Sri Bhuvanendra College, Karkala 574 104, India, bDepartment of Physics, Sri Bhuvanendra College, Karkala 574 104, India, cDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru-6, India, dInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru-6, India, and eDepartment of Chemistry, University College of Science, Tumkur University, Tumkur 572 103, India
*Correspondence e-mail: pasuchetan@yahoo.co.in

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 22 February 2017; accepted 24 February 2017; online 28 February 2017)

The mol­ecule of the title compound, C14H15NO4S, is L-shaped, with the central C—S—N—C segment having a torsion angle of −62.9 (2)°. The dihedral angle between the benzene rings is 89.17 (9)°. The C atoms of the meth­oxy groups are close to coplanar with their attached benzene ring [deviations = 0.084 (4) and −0.192 (5) Å]. An intra­molecular C—H⋯O hydrogen bond occurs. In the crystal, inversion dimers linked by pairs of N—H⋯O(S) hydrogen bonds generate R22(8) loops.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

In recent years, extensive research has been carried out on the synthesis and evaluation of the pharmacological activities of mol­ecules containing the sulfonamide moiety (Mohan et al., 2013[Mohan, N. R., Sreenivasa, S., Manojkumar, K. E. & Chakrapani Rao, T. M. (2013). J. Appl. Chem, 2, 722-729.]). As part of our ongoing studies on sulfonamides (Suchetan et al., 2016[Suchetan, P. A., Naveen, S., Lokanath, N. K., Srivishnu, K. S., Supriya, G. M. & Lakshmikantha, H. N. (2016). Acta Cryst. E72, 575-582.]), we report herein the crystal structure of the title compound.

The mol­ecule of the title compound (Fig. 1[link]) is L-shaped with the central C1—S1—N1—C7 segment having a torsion angle of −62.9 (2)° and the dihedral angle between the benzene rings being 89.17 (9)°. The two meth­oxy groups are close to coplanar with their attached benzene ring, the values of the torsion angles of the segment C1—C2—O3—C13 and C6—C5—O4—C14, respectively, being −175.2 (3) and −6.0 (5)°. The mol­ecular conformation is consolidated by an intra­molecular C12—H12⋯O1 hydrogen bond (Table 1[link]) forming a closed S(6) motif.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C12—H12⋯O1 0.93 2.52 3.1128 121
N1—H1⋯O2i 0.85 2.17 3.0116 (10) 170
Symmetry code: (i) -x+1, -y+2, -z+1.
[Figure 1]
Figure 1
A view of the mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. The intra­molecular hydrogen bond is indicated by a dashed line.

The crystal structure features inversion-related R22(8) dimers linked by pairs of N1—H1⋯O2i (Table 1[link] and Fig. 2[link]) hydrogen bonds.

[Figure 2]
Figure 2
A view of the R22(8) loops displayed in the crystal structure of the title compound due to N—H⋯O hydrogen bonds (dashed lines, see Table 1[link]).

Synthesis and crystallization

The title compound was prepared according to a literature method (Vinola et al., 2015[Vinola, Z. R., Snehala, Naveen, S., Lokanath, N. K. & Suchetan, P. A. (2015). Pharma Chem. 7, 299-307.]). The purity of the compound was checked by determining its melting point. Prismatic single crystals suitable for X-ray diffraction study were obtained by slow evaporation of an ethano­lic solution of the compound at room temperature.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C14H15NO4S
Mr 293.33
Crystal system, space group Monoclinic, P21/c
Temperature (K) 296
a, b, c (Å) 10.4328 (12), 14.3157 (15), 10.4869 (12)
β (°) 117.064 (6)
V3) 1394.7 (3)
Z 4
Radiation type Cu Kα
μ (mm−1) 2.19
Crystal size (mm) 0.28 × 0.22 × 0.17
 
Data collection
Diffractometer Bruker APEXII
Absorption correction Multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.589, 0.689
No. of measured, independent and observed [I > 2σ(I)] reflections 10083, 2305, 1943
Rint 0.065
(sin θ/λ)max−1) 0.586
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.186, 1.04
No. of reflections 2305
No. of parameters 188
No. of restraints 1
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.42, −0.33
Computer programs: APEX2, SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT2016 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2016 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and 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.]).

Structural data


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: SHELXT2016 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b).

2,5-Dimethoxy-N-phenylbenzenesulfonamide top
Crystal data top
C14H15NO4SPrism
Mr = 293.33Dx = 1.397 Mg m3
Monoclinic, P21/cMelting point: 439 K
Hall symbol: -P 2ybcCu Kα radiation, λ = 1.54178 Å
a = 10.4328 (12) ÅCell parameters from 143 reflections
b = 14.3157 (15) Åθ = 7.8–64.5°
c = 10.4869 (12) ŵ = 2.19 mm1
β = 117.064 (6)°T = 296 K
V = 1394.7 (3) Å3Prism, colourless
Z = 40.28 × 0.22 × 0.17 mm
F(000) = 616
Data collection top
Bruker APEXII
diffractometer
1943 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.065
Graphite monochromatorθmax = 64.5°, θmin = 7.8°
phi and φ scansh = 1211
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1616
Tmin = 0.589, Tmax = 0.689l = 1211
10083 measured reflections1 standard reflections every 1 reflections
2305 independent reflections intensity decay: 0.1%
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.067 w = 1/[σ2(Fo2) + (0.1364P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.186(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.42 e Å3
2305 reflectionsΔρmin = 0.33 e Å3
188 parametersExtinction correction: SHELXL2016 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0106 (19)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3763 (3)0.95415 (17)0.1449 (3)0.0446 (6)
C20.4926 (3)0.8928 (2)0.2056 (3)0.0554 (7)
C30.5215 (4)0.8363 (2)0.1138 (4)0.0729 (9)
H30.5980560.7945210.1516370.087*
C40.4387 (4)0.8413 (3)0.0311 (4)0.0770 (10)
H40.4600990.8030090.0905000.092*
C50.3243 (3)0.9021 (2)0.0908 (3)0.0629 (8)
C60.2922 (3)0.95933 (18)0.0021 (3)0.0517 (7)
H60.2150951.0006450.0409360.062*
C70.1886 (3)0.89741 (16)0.3259 (3)0.0408 (6)
C80.1959 (3)0.8411 (2)0.4360 (3)0.0560 (7)
H80.2729720.8461120.5271110.067*
C90.0868 (4)0.7771 (2)0.4089 (4)0.0691 (9)
H90.0902400.7396090.4828820.083*
C100.0254 (3)0.7683 (2)0.2754 (3)0.0642 (8)
H100.0975320.7246210.2580410.077*
C110.0312 (3)0.8241 (2)0.1673 (3)0.0592 (7)
H110.1081270.8183910.0762320.071*
C120.0749 (3)0.88843 (18)0.1910 (3)0.0490 (7)
H120.0700900.9257560.1163140.059*
C130.6919 (3)0.8361 (3)0.4161 (4)0.0818 (10)
H13A0.6663770.7714900.3947950.123*
H13B0.7360120.8453230.5178720.123*
H13C0.7582290.8536120.3801730.123*
C140.1182 (5)0.9532 (3)0.3002 (4)0.0897 (12)
H14A0.0563840.9358130.2586910.135*
H14B0.0700580.9413720.4013060.135*
H14C0.1409141.0184970.2836660.135*
N10.3015 (3)0.96370 (15)0.3628 (2)0.0477 (6)
O10.2068 (2)1.07776 (12)0.16321 (19)0.0545 (6)
O20.4588 (2)1.08222 (13)0.3458 (2)0.0583 (6)
O30.5672 (2)0.89154 (16)0.3507 (2)0.0716 (7)
O40.2466 (3)0.90022 (19)0.2364 (2)0.0871 (8)
S10.33445 (6)1.02855 (4)0.25483 (6)0.0437 (3)
H10.375 (2)0.9564 (18)0.443 (2)0.050 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0469 (15)0.0512 (13)0.0360 (14)0.0014 (11)0.0191 (12)0.0032 (10)
C20.0495 (15)0.0704 (17)0.0467 (16)0.0083 (13)0.0223 (13)0.0076 (13)
C30.0640 (19)0.087 (2)0.068 (2)0.0248 (17)0.0306 (17)0.0030 (16)
C40.077 (2)0.100 (2)0.062 (2)0.0176 (19)0.0388 (18)0.0133 (17)
C50.070 (2)0.0805 (19)0.0414 (17)0.0047 (16)0.0285 (15)0.0040 (13)
C60.0559 (17)0.0604 (15)0.0372 (15)0.0038 (12)0.0199 (13)0.0033 (11)
C70.0440 (13)0.0473 (13)0.0334 (13)0.0067 (10)0.0196 (10)0.0005 (10)
C80.0577 (16)0.0681 (17)0.0401 (15)0.0002 (13)0.0204 (13)0.0067 (12)
C90.080 (2)0.0732 (19)0.0603 (19)0.0054 (16)0.0372 (17)0.0132 (15)
C100.0610 (18)0.0627 (17)0.071 (2)0.0115 (14)0.0316 (16)0.0060 (14)
C110.0561 (16)0.0654 (17)0.0498 (17)0.0063 (13)0.0186 (13)0.0098 (13)
C120.0509 (15)0.0578 (15)0.0345 (14)0.0051 (12)0.0161 (11)0.0023 (11)
C130.0550 (19)0.107 (3)0.072 (2)0.0266 (18)0.0196 (16)0.0222 (19)
C140.110 (3)0.102 (3)0.0386 (18)0.032 (2)0.018 (2)0.0003 (18)
N10.0444 (13)0.0642 (14)0.0255 (12)0.0043 (10)0.0079 (10)0.0028 (9)
O10.0630 (12)0.0582 (11)0.0360 (10)0.0137 (9)0.0170 (9)0.0046 (7)
O20.0625 (12)0.0601 (11)0.0430 (11)0.0144 (9)0.0160 (9)0.0012 (8)
O30.0617 (13)0.0988 (16)0.0441 (12)0.0310 (11)0.0151 (10)0.0137 (10)
O40.0956 (18)0.122 (2)0.0404 (12)0.0229 (15)0.0278 (12)0.0134 (12)
S10.0481 (5)0.0484 (5)0.0295 (5)0.0005 (2)0.0130 (3)0.0020 (2)
Geometric parameters (Å, º) top
C1—C61.386 (4)C9—H90.9300
C1—C21.395 (4)C10—C111.366 (4)
C1—S11.764 (3)C10—H100.9300
C2—O31.359 (3)C11—C121.373 (4)
C2—C31.391 (4)C11—H110.9300
C3—C41.366 (5)C12—H120.9300
C3—H30.9300C13—O31.407 (4)
C4—C51.376 (4)C13—H13A0.9600
C4—H40.9300C13—H13B0.9600
C5—O41.365 (4)C13—H13C0.9600
C5—C61.390 (4)C14—O41.416 (4)
C6—H60.9300C14—H14A0.9600
C7—C121.378 (4)C14—H14B0.9600
C7—C81.382 (4)C14—H14C0.9600
C7—N11.422 (3)N1—S11.618 (2)
C8—C91.387 (4)N1—H10.849 (18)
C8—H80.9300O1—S11.4240 (19)
C9—C101.362 (4)O2—S11.4345 (19)
C6—C1—C2121.3 (2)C10—C11—C12121.0 (3)
C6—C1—S1118.3 (2)C10—C11—H11119.5
C2—C1—S1120.3 (2)C12—C11—H11119.5
O3—C2—C3125.0 (3)C11—C12—C7119.7 (2)
O3—C2—C1117.1 (2)C11—C12—H12120.2
C3—C2—C1117.9 (3)C7—C12—H12120.2
C4—C3—C2120.8 (3)O3—C13—H13A109.5
C4—C3—H3119.6O3—C13—H13B109.5
C2—C3—H3119.6H13A—C13—H13B109.5
C3—C4—C5121.2 (3)O3—C13—H13C109.5
C3—C4—H4119.4H13A—C13—H13C109.5
C5—C4—H4119.4H13B—C13—H13C109.5
O4—C5—C4116.5 (3)O4—C14—H14A109.5
O4—C5—C6124.0 (3)O4—C14—H14B109.5
C4—C5—C6119.4 (3)H14A—C14—H14B109.5
C1—C6—C5119.3 (3)O4—C14—H14C109.5
C1—C6—H6120.3H14A—C14—H14C109.5
C5—C6—H6120.3H14B—C14—H14C109.5
C12—C7—C8119.9 (2)C7—N1—S1127.30 (18)
C12—C7—N1124.1 (2)C7—N1—H1116.7 (19)
C8—C7—N1116.0 (2)S1—N1—H1113 (2)
C7—C8—C9119.1 (3)C2—O3—C13119.0 (2)
C7—C8—H8120.4C5—O4—C14118.0 (2)
C9—C8—H8120.4O1—S1—O2117.96 (12)
C10—C9—C8120.9 (3)O1—S1—N1108.95 (12)
C10—C9—H9119.6O2—S1—N1104.93 (11)
C8—C9—H9119.6O1—S1—C1106.93 (11)
C9—C10—C11119.5 (3)O2—S1—C1109.90 (12)
C9—C10—H10120.3N1—S1—C1107.79 (13)
C11—C10—H10120.3
C6—C1—C2—O3178.9 (3)C10—C11—C12—C70.4 (4)
S1—C1—C2—O32.0 (3)C8—C7—C12—C110.6 (4)
C6—C1—C2—C30.4 (4)N1—C7—C12—C11177.9 (2)
S1—C1—C2—C3179.5 (2)C12—C7—N1—S110.5 (4)
O3—C2—C3—C4178.8 (3)C8—C7—N1—S1170.9 (2)
C1—C2—C3—C40.4 (5)C3—C2—O3—C136.4 (5)
C2—C3—C4—C50.2 (6)C1—C2—O3—C13175.2 (3)
C3—C4—C5—O4178.6 (3)C4—C5—O4—C14172.4 (3)
C3—C4—C5—C60.1 (5)C6—C5—O4—C146.0 (5)
C2—C1—C6—C50.1 (4)C7—N1—S1—O152.9 (2)
S1—C1—C6—C5179.2 (2)C7—N1—S1—O2179.9 (2)
O4—C5—C6—C1178.5 (3)C7—N1—S1—C162.9 (2)
C4—C5—C6—C10.1 (4)C6—C1—S1—O14.3 (2)
C12—C7—C8—C90.9 (4)C2—C1—S1—O1176.6 (2)
N1—C7—C8—C9177.8 (2)C6—C1—S1—O2124.9 (2)
C7—C8—C9—C101.0 (5)C2—C1—S1—O254.3 (2)
C8—C9—C10—C110.7 (5)C6—C1—S1—N1121.3 (2)
C9—C10—C11—C120.4 (5)C2—C1—S1—N159.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O10.932.523.1128121
N1—H1···O2i0.852.173.0116 (10)170
Symmetry code: (i) x+1, y+2, z+1.
 

Footnotes

These authors contributed equally

§These authors contributed equally.

Acknowledgements

The authors are thankful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, Mysore, for providing the single-crystal X-ray diffraction data. KS is thankful to the University Grants Commission (UGC), New Delhi for the financial assistance under its MRP scheme.

References

First citationBruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.  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 citationMohan, N. R., Sreenivasa, S., Manojkumar, K. E. & Chakrapani Rao, T. M. (2013). J. Appl. Chem, 2, 722–729.  Google Scholar
First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSuchetan, P. A., Naveen, S., Lokanath, N. K., Srivishnu, K. S., Supriya, G. M. & Lakshmikantha, H. N. (2016). Acta Cryst. E72, 575–582.  CrossRef IUCr Journals Google Scholar
First citationVinola, Z. R., Snehala, Naveen, S., Lokanath, N. K. & Suchetan, P. A. (2015). Pharma Chem. 7, 299–307.  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 logoIUCrDATA
ISSN: 2414-3146
Follow IUCr Journals
Sign up for e-alerts
Follow IUCr on Twitter
Follow us on facebook
Sign up for RSS feeds