N-(3-Meth­oxy­benzo­yl)-4-methyl­benzene­sulfonamide

Sreenivasa, S.; Palakshamurthy, B.S.; Lohith, T.N.; Mohan, N.R.; Kumar, V.; Suchetan, P.A.

doi:10.1107/S1600536813019107

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1263

doi:10.1107/S1600536813019107

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N-(3-Methoxybenzoyl)-4-methylbenzenesulfonamide

S. Sreenivasa,^a B. S. Palakshamurthy,^b T. N. Lohith,^c N. R. Mohan,^a Vijith Kumar ^d and P. A. Suchetan ^e ^*

^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, ^cUniversity College of Science, Tumkur University, Tumkur, India, ^dSoild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, 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 30 June 2013; accepted 10 July 2013; online 17 July 2013)

In the title compound, C₁₅H₁₅NO₄S, the dihedral angle between the benzene rings is 88.87 (1)°. In the crystal, adjacent molecules form inversion dimers through pairs of strong N—H⋯O hydrogen bonds, generating R₂²(8) loops. Two C—H⋯π interactions and an aromatic π–π interaction [centroid–centroid separation = 3.8191 (1) Å] are also observed.

Related literature

For a similar structure, see: Suchetan et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₅NO₄S
M_r = 305.34
Triclinic, $[P \overline 1]$
a = 9.2474 (7) Å
b = 9.6660 (6) Å
c = 9.8764 (8) Å
α = 70.268 (6)°
β = 64.052 (8)°
γ = 86.231 (5)°
V = 743.69 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.35 × 0.28 × 0.22 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.925, T_max = 0.950
11424 measured reflections
2610 independent reflections
2212 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.112
S = 1.06
2610 reflections
196 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the sulfonyl-bound and carbonyl-bound benzene rings respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O1ⁱ	0.79 (2)	2.14 (2)	2.920 (2)	170 (2)
C15—H15B⋯Cg1ⁱⁱ	0.96	2.77	3.576 (3)	141
C7—H7A⋯Cg2ⁱⁱⁱ	0.96	2.94	3.753 (3)	143
Symmetry codes: (i) -x, -y+1, -z+2; (ii) -x+1, -y+2, -z+2; (iii) -x, -y+2, -z+2.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813019107/bg2511sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813019107/bg2511Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813019107/bg2511Isup3.cml

checkCIF report

Comment top

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

The conformation of the N—H bond in I is anti to the C=O bond in the side chain, similar to that observed in. N-(benzoyl)-4-methylbenzenesulfonamide (II, Suchetan et al., 2010). Further, the conformation between the N—H bond and the meta-methoxy group in the benzoyl ring is anti.

The dihedral angle between the methyl-substituted benzene ring (maximum deviation from mean plane: 0.007 Å for C5) and the methoxy-substituted benzene ring (maximum deviation from mean plane: 0.005 Å for C13) is 88.87 (1)°. Adjacent molecules form inversion related dimers through strong N—H···O hydrogen bonds, generating R₂²(8) loops (Fig 2). Two C—H···π interactions and an aromatic π-π interaction (centroid-centroid separation = 3.8191 (1) Å) are also observed in the structure (Fig 3).

Related literature top

For a similar structure, see: Suchetan et al. (2010).

Experimental top

The title compound was prepared by refluxing a mixture of 3-methoxybenzoic acid, 4-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: 405 K.) Colorless prisms of (I) were obtained from a slow evaporation of its ethanolic solution at room temperature.

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

	Fig. 1. Molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines. Carbon bounded hydrogen atoms are ommitted for clarity.
	Fig. 3. Display of C—H···π interactions and stacking of molecules through π-π interactions. Cg1 and Cg2 are the centroids of the sulfonyl bound and carbonyl bound benzene ring respectively. For clarity purpose, the hydrogen atoms not involved in hydrogen bonding are ommitted.

N-(3-Methoxybenzoyl)-4-methylbenzenesulfonamide top

Crystal data top

C₁₅H₁₅NO₄S	F(000) = 320
M_r = 305.34	Prism
Triclinic, P1	D_x = 1.364 Mg m⁻³
Hall symbol: -P 1	Melting point: 405 K
a = 9.2474 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6660 (6) Å	Cell parameters from 1123 reflections
c = 9.8764 (8) Å	θ = 2.4–25.0°
α = 70.268 (6)°	µ = 0.23 mm⁻¹
β = 64.052 (8)°	T = 293 K
γ = 86.231 (5)°	Prism, colourless
V = 743.69 (11) Å³	0.35 × 0.28 × 0.22 mm
Z = 2

Data collection top

Bruker APEXII diffractometer	2212 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 25.0°, θ_min = 2.4°
phi and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
T_min = 0.925, T_max = 0.950	l = −11→11
11424 measured reflections	3 standard reflections every 1 reflections
2610 independent reflections	intensity decay: 10%

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0515P)² + 0.194P] where P = (F_o² + 2F_c²)/3
2610 reflections	(Δ/σ)_max = 0.046
196 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₅H₁₅NO₄S	γ = 86.231 (5)°
M_r = 305.34	V = 743.69 (11) Å³
Triclinic, P1	Z = 2
a = 9.2474 (7) Å	Mo Kα radiation
b = 9.6660 (6) Å	µ = 0.23 mm⁻¹
c = 9.8764 (8) Å	T = 293 K
α = 70.268 (6)°	0.35 × 0.28 × 0.22 mm
β = 64.052 (8)°

Data collection top

Bruker APEXII diffractometer	2212 reflections with I > 2σ(I)
Absorption correction: multi-scan (SADABS; Bruker, 2009)	R_int = 0.037
T_min = 0.925, T_max = 0.950	3 standard reflections every 1 reflections
11424 measured reflections	intensity decay: 10%
2610 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.28 e Å⁻³
2610 reflections	Δρ_min = −0.25 e Å⁻³
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

	x	y	z	U_iso*/U_eq
HN1	0.159 (2)	0.588 (2)	0.975 (3)	0.051 (6)*
C1	0.1161 (2)	0.8457 (2)	0.6955 (2)	0.0476 (5)
C2	−0.0258 (2)	0.8795 (3)	0.8029 (2)	0.0613 (6)
H2	−0.0909	0.8073	0.8997	0.074*
C3	−0.0693 (3)	1.0213 (3)	0.7648 (3)	0.0662 (6)
H3	−0.1646	1.0442	0.8371	0.079*
C4	0.0256 (2)	1.1310 (2)	0.6209 (3)	0.0564 (5)
C5	0.1653 (2)	1.0931 (2)	0.5154 (2)	0.0553 (5)
H5	0.2292	1.1646	0.4174	0.066*
C6	0.2129 (2)	0.9520 (2)	0.5511 (2)	0.0518 (5)
H6	0.3084	0.9291	0.4791	0.062*
C7	−0.0228 (3)	1.2854 (3)	0.5835 (3)	0.0798 (7)
H7A	−0.1380	1.2822	0.6220	0.120*
H7B	0.0286	1.3360	0.4696	0.120*
H7C	0.0098	1.3368	0.6350	0.120*
C8	0.3499 (2)	0.7247 (2)	0.8738 (2)	0.0482 (5)
C9	0.3856 (2)	0.6830 (2)	1.0147 (2)	0.0446 (4)
C10	0.3358 (2)	0.5448 (2)	1.1356 (2)	0.0513 (5)
H10	0.2709	0.4755	1.1353	0.062*
C11	0.3844 (2)	0.5127 (2)	1.2554 (2)	0.0554 (5)
H11	0.3525	0.4203	1.3357	0.066*
C12	0.4792 (2)	0.6145 (2)	1.2591 (2)	0.0519 (5)
H12	0.5105	0.5910	1.3411	0.062*
C13	0.5272 (2)	0.7517 (2)	1.1398 (2)	0.0508 (5)
C14	0.4814 (2)	0.7857 (2)	1.0170 (2)	0.0512 (5)
H14	0.5150	0.8777	0.9361	0.061*
C15	0.6780 (3)	0.8309 (3)	1.2494 (3)	0.0782 (7)
H15A	0.5879	0.8074	1.3536	0.117*
H15B	0.7428	0.9162	1.2284	0.117*
H15C	0.7421	0.7488	1.2462	0.117*
N1	0.2204 (2)	0.6435 (2)	0.8917 (2)	0.0519 (4)
O1	0.03105 (19)	0.56323 (17)	0.81816 (17)	0.0674 (4)
O2	0.30852 (18)	0.65075 (17)	0.60995 (16)	0.0643 (4)
O3	0.42784 (17)	0.82263 (17)	0.74840 (17)	0.0633 (4)
O4	0.6206 (2)	0.86118 (18)	1.13085 (19)	0.0731 (5)
S1	0.17181 (6)	0.66553 (6)	0.74433 (6)	0.05142 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0453 (10)	0.0573 (12)	0.0412 (10)	0.0008 (8)	−0.0216 (8)	−0.0141 (9)
C2	0.0511 (12)	0.0712 (15)	0.0451 (11)	−0.0006 (10)	−0.0140 (9)	−0.0093 (10)
C3	0.0524 (12)	0.0811 (17)	0.0590 (13)	0.0133 (11)	−0.0192 (11)	−0.0256 (12)
C4	0.0553 (12)	0.0622 (13)	0.0619 (13)	0.0095 (10)	−0.0341 (11)	−0.0227 (11)
C5	0.0562 (12)	0.0537 (12)	0.0494 (11)	−0.0019 (9)	−0.0231 (10)	−0.0091 (9)
C6	0.0478 (11)	0.0584 (12)	0.0427 (10)	0.0014 (9)	−0.0168 (9)	−0.0134 (9)
C7	0.0820 (17)	0.0748 (17)	0.0900 (18)	0.0235 (14)	−0.0445 (15)	−0.0313 (14)
C8	0.0462 (10)	0.0508 (11)	0.0453 (11)	0.0046 (9)	−0.0213 (9)	−0.0124 (9)
C9	0.0416 (10)	0.0490 (11)	0.0425 (10)	0.0064 (8)	−0.0192 (8)	−0.0144 (8)
C10	0.0537 (11)	0.0480 (11)	0.0516 (11)	0.0014 (9)	−0.0252 (9)	−0.0133 (9)
C11	0.0625 (13)	0.0487 (12)	0.0494 (11)	0.0032 (9)	−0.0274 (10)	−0.0064 (9)
C12	0.0522 (11)	0.0606 (13)	0.0453 (11)	0.0097 (9)	−0.0257 (9)	−0.0163 (9)
C13	0.0486 (11)	0.0543 (12)	0.0526 (11)	0.0042 (9)	−0.0259 (9)	−0.0171 (9)
C14	0.0518 (11)	0.0492 (11)	0.0501 (11)	0.0008 (9)	−0.0254 (9)	−0.0094 (9)
C15	0.0851 (17)	0.0866 (18)	0.0832 (17)	−0.0041 (14)	−0.0573 (15)	−0.0237 (14)
N1	0.0531 (10)	0.0574 (11)	0.0395 (9)	−0.0067 (8)	−0.0228 (8)	−0.0048 (8)
O1	0.0801 (10)	0.0657 (10)	0.0571 (9)	−0.0210 (8)	−0.0398 (8)	−0.0038 (7)
O2	0.0778 (10)	0.0666 (10)	0.0472 (8)	0.0167 (8)	−0.0259 (7)	−0.0220 (7)
O3	0.0605 (9)	0.0685 (10)	0.0493 (8)	−0.0100 (7)	−0.0258 (7)	−0.0015 (7)
O4	0.0847 (11)	0.0708 (11)	0.0749 (10)	−0.0137 (8)	−0.0520 (9)	−0.0113 (8)
S1	0.0595 (3)	0.0537 (3)	0.0418 (3)	−0.0022 (2)	−0.0265 (2)	−0.0105 (2)

Geometric parameters (Å, º) top

C1—C6	1.381 (3)	C9—C10	1.394 (3)
C1—C2	1.383 (3)	C10—C11	1.378 (3)
C1—S1	1.750 (2)	C10—H10	0.9300
C2—C3	1.377 (3)	C11—C12	1.380 (3)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.389 (3)	C12—C13	1.381 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.380 (3)	C13—O4	1.366 (2)
C4—C7	1.500 (3)	C13—C14	1.385 (3)
C5—C6	1.383 (3)	C14—H14	0.9300
C5—H5	0.9300	C15—O4	1.426 (3)
C6—H6	0.9300	C15—H15A	0.9600
C7—H7A	0.9600	C15—H15B	0.9600
C7—H7B	0.9600	C15—H15C	0.9600
C7—H7C	0.9600	N1—S1	1.6477 (16)
C8—O3	1.211 (2)	N1—HN1	0.79 (2)
C8—N1	1.388 (2)	O1—S1	1.4338 (15)
C8—C9	1.488 (3)	O2—S1	1.4199 (15)
C9—C14	1.386 (3)

C6—C1—C2	120.7 (2)	C11—C10—H10	120.5
C6—C1—S1	120.07 (15)	C9—C10—H10	120.5
C2—C1—S1	119.19 (15)	C10—C11—C12	121.46 (19)
C3—C2—C1	119.2 (2)	C10—C11—H11	119.3
C3—C2—H2	120.4	C12—C11—H11	119.3
C1—C2—H2	120.4	C11—C12—C13	119.41 (18)
C2—C3—C4	121.5 (2)	C11—C12—H12	120.3
C2—C3—H3	119.3	C13—C12—H12	120.3
C4—C3—H3	119.3	O4—C13—C12	124.67 (18)
C5—C4—C3	117.8 (2)	O4—C13—C14	115.23 (18)
C5—C4—C7	121.7 (2)	C12—C13—C14	120.10 (18)
C3—C4—C7	120.5 (2)	C13—C14—C9	120.09 (18)
C4—C5—C6	121.92 (19)	C13—C14—H14	120.0
C4—C5—H5	119.0	C9—C14—H14	120.0
C6—C5—H5	119.0	O4—C15—H15A	109.5
C1—C6—C5	118.76 (19)	O4—C15—H15B	109.5
C1—C6—H6	120.6	H15A—C15—H15B	109.5
C5—C6—H6	120.6	O4—C15—H15C	109.5
C4—C7—H7A	109.5	H15A—C15—H15C	109.5
C4—C7—H7B	109.5	H15B—C15—H15C	109.5
H7A—C7—H7B	109.5	C8—N1—S1	123.04 (14)
C4—C7—H7C	109.5	C8—N1—HN1	122.9 (15)
H7A—C7—H7C	109.5	S1—N1—HN1	113.9 (15)
H7B—C7—H7C	109.5	C13—O4—C15	118.08 (17)
O3—C8—N1	120.27 (18)	O2—S1—O1	118.61 (10)
O3—C8—C9	123.41 (17)	O2—S1—N1	109.61 (9)
N1—C8—C9	116.31 (16)	O1—S1—N1	103.41 (9)
C14—C9—C10	120.02 (17)	O2—S1—C1	109.64 (9)
C14—C9—C8	116.76 (17)	O1—S1—C1	109.03 (9)
C10—C9—C8	123.10 (17)	N1—S1—C1	105.68 (9)
C11—C10—C9	118.92 (18)

C6—C1—C2—C3	−0.4 (3)	C11—C12—C13—C14	−0.6 (3)
S1—C1—C2—C3	179.73 (17)	O4—C13—C14—C9	−179.59 (17)
C1—C2—C3—C4	0.2 (3)	C12—C13—C14—C9	0.8 (3)
C2—C3—C4—C5	0.7 (3)	C10—C9—C14—C13	−0.3 (3)
C2—C3—C4—C7	−178.8 (2)	C8—C9—C14—C13	−176.47 (17)
C3—C4—C5—C6	−1.4 (3)	O3—C8—N1—S1	4.2 (3)
C7—C4—C5—C6	178.2 (2)	C9—C8—N1—S1	−175.21 (13)
C2—C1—C6—C5	−0.2 (3)	C12—C13—O4—C15	2.4 (3)
S1—C1—C6—C5	179.63 (14)	C14—C13—O4—C15	−177.17 (19)
C4—C5—C6—C1	1.1 (3)	C8—N1—S1—O2	54.03 (19)
O3—C8—C9—C14	18.3 (3)	C8—N1—S1—O1	−178.56 (16)
N1—C8—C9—C14	−162.34 (17)	C8—N1—S1—C1	−64.03 (18)
O3—C8—C9—C10	−157.8 (2)	C6—C1—S1—O2	−7.39 (19)
N1—C8—C9—C10	21.6 (3)	C2—C1—S1—O2	172.45 (15)
C14—C9—C10—C11	−0.5 (3)	C6—C1—S1—O1	−138.75 (16)
C8—C9—C10—C11	175.44 (17)	C2—C1—S1—O1	41.08 (18)
C9—C10—C11—C12	0.7 (3)	C6—C1—S1—N1	110.66 (17)
C10—C11—C12—C13	−0.2 (3)	C2—C1—S1—N1	−69.50 (17)
C11—C12—C13—O4	179.91 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the sulfonyl-bound and carbonyl-bound benzene rings respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1ⁱ	0.79 (2)	2.14 (2)	2.920 (2)	170 (2)
C15—H15B···Cg1ⁱⁱ	0.96	2.77	3.576 (3)	141
C7—H7A···Cg2ⁱⁱⁱ	0.96	2.94	3.753 (3)	143

Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x+1, −y+2, −z+2; (iii) −x, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the sulfonyl-bound and carbonyl-bound benzene rings respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1ⁱ	0.79 (2)	2.14 (2)	2.920 (2)	170 (2)
C15—H15B···Cg1ⁱⁱ	0.96	2.77	3.576 (3)	141
C7—H7A···Cg2ⁱⁱⁱ	0.96	2.94	3.753 (3)	143

Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x+1, −y+2, −z+2; (iii) −x, −y+2, −z+2.

Acknowledgements

PAS acknowledges the University Grants Commission (UGC), India, for financial support under its Minor Research Project scheme.

References

Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 69| Part 8| August 2013| Page o1263

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