2,5-Dimeth­oxy-N-phenyl­benzene­sulfonamide

Shakuntala, K.; Kumari, V.; Lokanath, N.K.; Naveen, S.; Suchetan, P.A.

doi:10.1107/S241431461700311X

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170311

https://doi.org/10.1107/S241431461700311X

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2,5-Dimethoxy-N-phenylbenzenesulfonamide

K. Shakuntala,^a ‡ Vijaya Kumari,^b N. K. Lokanath,^c S. Naveen ^d § and P. A. Suchetan ^e ^*

^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.

Keywords: crystal structure; sulfonamides; N—H⋯O hydrogen bonds; intramolecular C—H⋯O hydrogen bond.

CCDC reference: 1534581

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 ). As part of our ongoing studies on sulfonamides (Suchetan et al., 2016 ), we report herein the crystal structure of the title compound.

The molecule of the title compound (Fig. 1) 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) forming a closed S(6) motif.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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
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 and Fig. 2) hydrogen bonds.

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

Synthesis and crystallization

The title compound was prepared according to a literature method (Vinola et al., 2015 ). 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.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₁₅NO₄S
M_r	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)
V (Å³)	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 )
T_min, T_max	0.589, 0.689
No. of measured, independent and observed [I > 2σ(I)] reflections	10083, 2305, 1943
R_int	0.065
(sin θ/λ)_max (Å⁻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
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.33
Computer programs: APEX2, SAINT-Plus and XPREP (Bruker, 2009), SHELXT2016 (Sheldrick, 2015a ), SHELXL2016 (Sheldrick, 2015b ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1534581

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S241431461700311X/hb4126sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461700311X/hb4126Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S241431461700311X/hb4126Isup3.cml

checkCIF report

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

C₁₄H₁₅NO₄S	Prism
M_r = 293.33	D_x = 1.397 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 439 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 10.4328 (12) Å	Cell parameters from 143 reflections
b = 14.3157 (15) Å	θ = 7.8–64.5°
c = 10.4869 (12) Å	µ = 2.19 mm⁻¹
β = 117.064 (6)°	T = 296 K
V = 1394.7 (3) Å³	Prism, colourless
Z = 4	0.28 × 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 tube	R_int = 0.065
Graphite monochromator	θ_max = 64.5°, θ_min = 7.8°
phi and φ scans	h = −12→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −16→16
T_min = 0.589, T_max = 0.689	l = −12→11
10083 measured reflections	1 standard reflections every 1 reflections
2305 independent reflections	intensity decay: 0.1%

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.067	w = 1/[σ²(F_o²) + (0.1364P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.186	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 0.42 e Å⁻³
2305 reflections	Δρ_min = −0.33 e Å⁻³
188 parameters	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction 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

	x	y	z	U_iso*/U_eq
C1	0.3763 (3)	0.95415 (17)	0.1449 (3)	0.0446 (6)
C2	0.4926 (3)	0.8928 (2)	0.2056 (3)	0.0554 (7)
C3	0.5215 (4)	0.8363 (2)	0.1138 (4)	0.0729 (9)
H3	0.598056	0.794521	0.151637	0.087*
C4	0.4387 (4)	0.8413 (3)	−0.0311 (4)	0.0770 (10)
H4	0.460099	0.803009	−0.090500	0.092*
C5	0.3243 (3)	0.9021 (2)	−0.0908 (3)	0.0629 (8)
C6	0.2922 (3)	0.95933 (18)	−0.0021 (3)	0.0517 (7)
H6	0.215095	1.000645	−0.040936	0.062*
C7	0.1886 (3)	0.89741 (16)	0.3259 (3)	0.0408 (6)
C8	0.1959 (3)	0.8411 (2)	0.4360 (3)	0.0560 (7)
H8	0.272972	0.846112	0.527111	0.067*
C9	0.0868 (4)	0.7771 (2)	0.4089 (4)	0.0691 (9)
H9	0.090240	0.739609	0.482882	0.083*
C10	−0.0254 (3)	0.7683 (2)	0.2754 (3)	0.0642 (8)
H10	−0.097532	0.724621	0.258041	0.077*
C11	−0.0312 (3)	0.8241 (2)	0.1673 (3)	0.0592 (7)
H11	−0.108127	0.818391	0.076232	0.071*
C12	0.0749 (3)	0.88843 (18)	0.1910 (3)	0.0490 (7)
H12	0.070090	0.925756	0.116314	0.059*
C13	0.6919 (3)	0.8361 (3)	0.4161 (4)	0.0818 (10)
H13A	0.666377	0.771490	0.394795	0.123*
H13B	0.736012	0.845323	0.517872	0.123*
H13C	0.758229	0.853612	0.380173	0.123*
C14	0.1182 (5)	0.9532 (3)	−0.3002 (4)	0.0897 (12)
H14A	0.056384	0.935813	−0.258691	0.135*
H14B	0.070058	0.941372	−0.401306	0.135*
H14C	0.140914	1.018497	−0.283666	0.135*
N1	0.3015 (3)	0.96370 (15)	0.3628 (2)	0.0477 (6)
O1	0.2068 (2)	1.07776 (12)	0.16321 (19)	0.0545 (6)
O2	0.4588 (2)	1.08222 (13)	0.3458 (2)	0.0583 (6)
O3	0.5672 (2)	0.89154 (16)	0.3507 (2)	0.0716 (7)
O4	0.2466 (3)	0.90022 (19)	−0.2364 (2)	0.0871 (8)
S1	0.33445 (6)	1.02855 (4)	0.25483 (6)	0.0437 (3)
H1	0.375 (2)	0.9564 (18)	0.443 (2)	0.050 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0469 (15)	0.0512 (13)	0.0360 (14)	0.0014 (11)	0.0191 (12)	0.0032 (10)
C2	0.0495 (15)	0.0704 (17)	0.0467 (16)	0.0083 (13)	0.0223 (13)	0.0076 (13)
C3	0.0640 (19)	0.087 (2)	0.068 (2)	0.0248 (17)	0.0306 (17)	0.0030 (16)
C4	0.077 (2)	0.100 (2)	0.062 (2)	0.0176 (19)	0.0388 (18)	−0.0133 (17)
C5	0.070 (2)	0.0805 (19)	0.0414 (17)	0.0047 (16)	0.0285 (15)	−0.0040 (13)
C6	0.0559 (17)	0.0604 (15)	0.0372 (15)	0.0038 (12)	0.0199 (13)	0.0033 (11)
C7	0.0440 (13)	0.0473 (13)	0.0334 (13)	0.0067 (10)	0.0196 (10)	−0.0005 (10)
C8	0.0577 (16)	0.0681 (17)	0.0401 (15)	0.0002 (13)	0.0204 (13)	0.0067 (12)
C9	0.080 (2)	0.0732 (19)	0.0603 (19)	−0.0054 (16)	0.0372 (17)	0.0132 (15)
C10	0.0610 (18)	0.0627 (17)	0.071 (2)	−0.0115 (14)	0.0316 (16)	−0.0060 (14)
C11	0.0561 (16)	0.0654 (17)	0.0498 (17)	−0.0063 (13)	0.0186 (13)	−0.0098 (13)
C12	0.0509 (15)	0.0578 (15)	0.0345 (14)	−0.0051 (12)	0.0161 (11)	−0.0023 (11)
C13	0.0550 (19)	0.107 (3)	0.072 (2)	0.0266 (18)	0.0196 (16)	0.0222 (19)
C14	0.110 (3)	0.102 (3)	0.0386 (18)	0.032 (2)	0.018 (2)	0.0003 (18)
N1	0.0444 (13)	0.0642 (14)	0.0255 (12)	−0.0043 (10)	0.0079 (10)	0.0028 (9)
O1	0.0630 (12)	0.0582 (11)	0.0360 (10)	0.0137 (9)	0.0170 (9)	0.0046 (7)
O2	0.0625 (12)	0.0601 (11)	0.0430 (11)	−0.0144 (9)	0.0160 (9)	−0.0012 (8)
O3	0.0617 (13)	0.0988 (16)	0.0441 (12)	0.0310 (11)	0.0151 (10)	0.0137 (10)
O4	0.0956 (18)	0.122 (2)	0.0404 (12)	0.0229 (15)	0.0278 (12)	−0.0134 (12)
S1	0.0481 (5)	0.0484 (5)	0.0295 (5)	0.0005 (2)	0.0130 (3)	0.0020 (2)

Geometric parameters (Å, º) top

C1—C6	1.386 (4)	C9—H9	0.9300
C1—C2	1.395 (4)	C10—C11	1.366 (4)
C1—S1	1.764 (3)	C10—H10	0.9300
C2—O3	1.359 (3)	C11—C12	1.373 (4)
C2—C3	1.391 (4)	C11—H11	0.9300
C3—C4	1.366 (5)	C12—H12	0.9300
C3—H3	0.9300	C13—O3	1.407 (4)
C4—C5	1.376 (4)	C13—H13A	0.9600
C4—H4	0.9300	C13—H13B	0.9600
C5—O4	1.365 (4)	C13—H13C	0.9600
C5—C6	1.390 (4)	C14—O4	1.416 (4)
C6—H6	0.9300	C14—H14A	0.9600
C7—C12	1.378 (4)	C14—H14B	0.9600
C7—C8	1.382 (4)	C14—H14C	0.9600
C7—N1	1.422 (3)	N1—S1	1.618 (2)
C8—C9	1.387 (4)	N1—H1	0.849 (18)
C8—H8	0.9300	O1—S1	1.4240 (19)
C9—C10	1.362 (4)	O2—S1	1.4345 (19)

C6—C1—C2	121.3 (2)	C10—C11—C12	121.0 (3)
C6—C1—S1	118.3 (2)	C10—C11—H11	119.5
C2—C1—S1	120.3 (2)	C12—C11—H11	119.5
O3—C2—C3	125.0 (3)	C11—C12—C7	119.7 (2)
O3—C2—C1	117.1 (2)	C11—C12—H12	120.2
C3—C2—C1	117.9 (3)	C7—C12—H12	120.2
C4—C3—C2	120.8 (3)	O3—C13—H13A	109.5
C4—C3—H3	119.6	O3—C13—H13B	109.5
C2—C3—H3	119.6	H13A—C13—H13B	109.5
C3—C4—C5	121.2 (3)	O3—C13—H13C	109.5
C3—C4—H4	119.4	H13A—C13—H13C	109.5
C5—C4—H4	119.4	H13B—C13—H13C	109.5
O4—C5—C4	116.5 (3)	O4—C14—H14A	109.5
O4—C5—C6	124.0 (3)	O4—C14—H14B	109.5
C4—C5—C6	119.4 (3)	H14A—C14—H14B	109.5
C1—C6—C5	119.3 (3)	O4—C14—H14C	109.5
C1—C6—H6	120.3	H14A—C14—H14C	109.5
C5—C6—H6	120.3	H14B—C14—H14C	109.5
C12—C7—C8	119.9 (2)	C7—N1—S1	127.30 (18)
C12—C7—N1	124.1 (2)	C7—N1—H1	116.7 (19)
C8—C7—N1	116.0 (2)	S1—N1—H1	113 (2)
C7—C8—C9	119.1 (3)	C2—O3—C13	119.0 (2)
C7—C8—H8	120.4	C5—O4—C14	118.0 (2)
C9—C8—H8	120.4	O1—S1—O2	117.96 (12)
C10—C9—C8	120.9 (3)	O1—S1—N1	108.95 (12)
C10—C9—H9	119.6	O2—S1—N1	104.93 (11)
C8—C9—H9	119.6	O1—S1—C1	106.93 (11)
C9—C10—C11	119.5 (3)	O2—S1—C1	109.90 (12)
C9—C10—H10	120.3	N1—S1—C1	107.79 (13)
C11—C10—H10	120.3

C6—C1—C2—O3	−178.9 (3)	C10—C11—C12—C7	−0.4 (4)
S1—C1—C2—O3	2.0 (3)	C8—C7—C12—C11	0.6 (4)
C6—C1—C2—C3	−0.4 (4)	N1—C7—C12—C11	−177.9 (2)
S1—C1—C2—C3	−179.5 (2)	C12—C7—N1—S1	−10.5 (4)
O3—C2—C3—C4	178.8 (3)	C8—C7—N1—S1	170.9 (2)
C1—C2—C3—C4	0.4 (5)	C3—C2—O3—C13	6.4 (5)
C2—C3—C4—C5	−0.2 (6)	C1—C2—O3—C13	−175.2 (3)
C3—C4—C5—O4	−178.6 (3)	C4—C5—O4—C14	172.4 (3)
C3—C4—C5—C6	−0.1 (5)	C6—C5—O4—C14	−6.0 (5)
C2—C1—C6—C5	0.1 (4)	C7—N1—S1—O1	52.9 (2)
S1—C1—C6—C5	179.2 (2)	C7—N1—S1—O2	−179.9 (2)
O4—C5—C6—C1	178.5 (3)	C7—N1—S1—C1	−62.9 (2)
C4—C5—C6—C1	0.1 (4)	C6—C1—S1—O1	4.3 (2)
C12—C7—C8—C9	−0.9 (4)	C2—C1—S1—O1	−176.6 (2)
N1—C7—C8—C9	177.8 (2)	C6—C1—S1—O2	−124.9 (2)
C7—C8—C9—C10	1.0 (5)	C2—C1—S1—O2	54.3 (2)
C8—C9—C10—C11	−0.7 (5)	C6—C1—S1—N1	121.3 (2)
C9—C10—C11—C12	0.4 (5)	C2—C1—S1—N1	−59.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

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

Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Mohan, N. R., Sreenivasa, S., Manojkumar, K. E. & Chakrapani Rao, T. M. (2013). J. Appl. Chem, 2, 722–729. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Suchetan, 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
Vinola, Z. R., Snehala, Naveen, S., Lokanath, N. K. & Suchetan, P. A. (2015). Pharma Chem. 7, 299–307. Google Scholar