N-(4-Meth­oxy­benzo­yl)benzene­sulfon­amide

Sreenivasa, S.; Nanjundaswamy, M.S.; Madankumar, S.; Lokanath, N.K.; Suresha, E.; Suchetan, P.A.

doi:10.1107/S1600536814001330

organic compounds

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ISSN: 2056-9890

Volume 70| Part 2| February 2014| Page o192

doi:10.1107/S1600536814001330

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N-(4-Methoxybenzoyl)benzenesulfonamide

S. Sreenivasa,^a M. S. Nanjundaswamy,^b S. Madankumar,^c N. K. Lokanath,^c E. Suresha ^d and P. A. Suchetan ^e ^*

^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.

CCDC reference: 978142

Related literature

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

Experimental

Crystal data

C₁₄H₁₃NO₄S
M_r = 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 ) T_min = 0.515, T_max = 0.633
8561 measured reflections
2168 independent reflections
2076 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.33 e Å⁻³
Δρ_min = −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	D⋯A	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); 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

CCDC reference: 978142

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814001330/hb7187sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814001330/hb7187Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814001330/hb7187Isup3.cml

checkCIF report

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

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

Synthesis and crystallization top

Colorless prisms of (I) were obtained from a slow evaporation of its aqueous methanolic solution at room temperature.

Refinement details top

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 displacement ellipsoids drawn at the 50% probability level.
	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.
	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.
	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

C₁₄H₁₃NO₄S	F(000) = 304
M_r = 291.31	Prism
Triclinic, P1	D_x = 1.449 Mg m⁻³
Hall symbol: -P 1	Melting point: 399 K
a = 5.3059 (5) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.6343 (10) Å	Cell parameters from 25 reflections
c = 11.9139 (11) Å	θ = 3.7–64.8°
α = 89.792 (3)°	µ = 2.28 mm⁻¹
β = 87.392 (3)°	T = 293 K
γ = 83.944 (3)°	Prism, colourless
V = 667.79 (11) Å³	0.37 × 0.26 × 0.20 mm
Z = 2

Data collection top

Bruker APEXII diffractometer	2076 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.049
Graphite monochromator	θ_max = 64.8°, θ_min = 3.7°
phi and φ scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
T_min = 0.515, T_max = 0.633	l = −13→13
8561 measured reflections	3 standard reflections every 120 min
2168 independent reflections	intensity decay: 1%

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ²(F_o²) + (0.1013P)² + 0.1754P] where P = (F_o² + 2F_c²)/3
2168 reflections	(Δ/σ)_max < 0.001
186 parameters	Δρ_max = 0.33 e Å⁻³
1 restraint	Δρ_min = −0.84 e Å⁻³

Crystal data top

C₁₄H₁₃NO₄S	γ = 83.944 (3)°
M_r = 291.31	V = 667.79 (11) Å³
Triclinic, P1	Z = 2
a = 5.3059 (5) Å	Cu Kα radiation
b = 10.6343 (10) Å	µ = 2.28 mm⁻¹
c = 11.9139 (11) Å	T = 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)	R_int = 0.049
T_min = 0.515, T_max = 0.633	3 standard reflections every 120 min
8561 measured reflections	intensity decay: 1%
2168 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	1 restraint
wR(F²) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	Δρ_max = 0.33 e Å⁻³
2168 reflections	Δρ_min = −0.84 e Å⁻³
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

	x	y	z	U_iso*/U_eq
O1	0.2427 (3)	0.36646 (17)	0.44504 (16)	0.0596 (5)
N1	0.6766 (4)	0.40318 (19)	0.36803 (17)	0.0478 (5)
O3	0.4534 (3)	0.39943 (16)	0.21164 (15)	0.0559 (5)
O4	1.1816 (4)	0.81223 (19)	0.06023 (17)	0.0695 (6)
C13	0.9563 (4)	0.5966 (2)	0.26610 (18)	0.0421 (5)
H13	0.9898	0.5737	0.3398	0.051*
C7	0.6197 (4)	0.4435 (2)	0.25993 (19)	0.0424 (5)
O2	0.6259 (4)	0.30297 (18)	0.54898 (15)	0.0624 (5)
C9	0.7269 (6)	0.5777 (3)	0.1010 (2)	0.0609 (7)
H9	0.6030	0.5417	0.0631	0.073*
C1	0.5310 (4)	0.1655 (2)	0.37956 (18)	0.0405 (5)
C12	1.0878 (4)	0.6857 (2)	0.2130 (2)	0.0475 (6)
H12	1.2101	0.7227	0.2512	0.057*
C8	0.7732 (4)	0.5405 (2)	0.21008 (18)	0.0402 (5)
C11	1.0410 (5)	0.7213 (2)	0.1032 (2)	0.0472 (6)
C5	0.3772 (5)	0.0164 (2)	0.2584 (2)	0.0564 (6)
H5	0.2579	−0.0048	0.2089	0.068*
C3	0.7531 (5)	−0.0405 (3)	0.3552 (3)	0.0649 (8)
H3	0.8890	−0.0996	0.3709	0.078*
C4	0.5776 (5)	−0.0707 (2)	0.2829 (2)	0.0547 (6)
H4	0.5930	−0.1504	0.2500	0.066*
C2	0.7307 (5)	0.0778 (3)	0.4055 (2)	0.0574 (6)
H2	0.8487	0.0979	0.4562	0.069*
C14	1.1590 (10)	0.8451 (4)	−0.0546 (3)	0.0986 (13)
H14A	1.2092	0.7720	−0.1005	0.148*
H14B	1.2665	0.9100	−0.0734	0.148*
H14C	0.9860	0.8757	−0.0676	0.148*
C6	0.3516 (4)	0.1360 (2)	0.3071 (2)	0.0498 (6)
H6	0.2157	0.1948	0.2910	0.060*
C10	0.8596 (6)	0.6669 (3)	0.0467 (2)	0.0635 (7)
H10	0.8267	0.6899	−0.0270	0.076*
S1	0.50162 (10)	0.31426 (5)	0.44550 (4)	0.0452 (3)
HN1	0.808 (6)	0.419 (4)	0.397 (3)	0.091 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0540 (10)	0.0592 (10)	0.0642 (11)	−0.0033 (8)	0.0092 (8)	−0.0138 (8)
N1	0.0543 (12)	0.0501 (11)	0.0432 (11)	−0.0222 (9)	−0.0093 (9)	0.0000 (8)
O3	0.0563 (10)	0.0581 (10)	0.0573 (10)	−0.0197 (8)	−0.0149 (8)	−0.0071 (8)
O4	0.0829 (14)	0.0677 (12)	0.0582 (12)	−0.0183 (10)	0.0158 (10)	0.0140 (9)
C13	0.0460 (12)	0.0463 (11)	0.0348 (11)	−0.0079 (9)	−0.0035 (9)	−0.0026 (9)
C7	0.0460 (12)	0.0400 (11)	0.0419 (12)	−0.0065 (9)	−0.0039 (9)	−0.0105 (9)
O2	0.0851 (13)	0.0689 (11)	0.0385 (9)	−0.0294 (10)	−0.0111 (9)	−0.0024 (8)
C9	0.0753 (18)	0.0729 (17)	0.0393 (13)	−0.0241 (13)	−0.0155 (12)	−0.0048 (11)
C1	0.0383 (11)	0.0445 (11)	0.0403 (11)	−0.0142 (8)	0.0036 (8)	−0.0022 (8)
C12	0.0477 (12)	0.0519 (13)	0.0445 (12)	−0.0126 (10)	−0.0019 (9)	−0.0006 (10)
C8	0.0427 (11)	0.0417 (11)	0.0361 (11)	−0.0047 (9)	0.0001 (9)	−0.0081 (8)
C11	0.0523 (13)	0.0460 (12)	0.0418 (12)	−0.0035 (10)	0.0118 (10)	−0.0010 (9)
C5	0.0568 (14)	0.0537 (14)	0.0624 (16)	−0.0215 (11)	−0.0058 (11)	−0.0110 (11)
C3	0.0542 (15)	0.0558 (15)	0.083 (2)	0.0029 (12)	−0.0004 (14)	−0.0073 (13)
C4	0.0572 (14)	0.0445 (12)	0.0628 (16)	−0.0153 (10)	0.0159 (12)	−0.0095 (10)
C2	0.0450 (13)	0.0652 (15)	0.0628 (15)	−0.0071 (11)	−0.0084 (11)	−0.0083 (12)
C14	0.147 (4)	0.091 (2)	0.0561 (19)	−0.018 (2)	0.032 (2)	0.0156 (17)
C6	0.0449 (12)	0.0469 (12)	0.0598 (14)	−0.0128 (9)	−0.0081 (10)	−0.0050 (10)
C10	0.084 (2)	0.0740 (17)	0.0338 (12)	−0.0134 (14)	−0.0043 (12)	0.0032 (11)
S1	0.0516 (4)	0.0468 (4)	0.0393 (4)	−0.0156 (3)	0.0011 (3)	−0.0074 (2)

Geometric parameters (Å, º) top

O1—S1	1.4264 (19)	C1—S1	1.758 (2)
N1—C7	1.392 (3)	C12—C11	1.387 (3)
N1—S1	1.646 (2)	C12—H12	0.9300
N1—HN1	0.82 (3)	C11—C10	1.376 (4)
O3—C7	1.211 (3)	C5—C4	1.376 (4)
O4—C11	1.367 (3)	C5—C6	1.390 (4)
O4—C14	1.418 (4)	C5—H5	0.9300
C13—C12	1.371 (3)	C3—C4	1.360 (4)
C13—C8	1.389 (3)	C3—C2	1.388 (4)
C13—H13	0.9300	C3—H3	0.9300
C7—C8	1.486 (3)	C4—H4	0.9300
O2—S1	1.4232 (19)	C2—H2	0.9300
C9—C10	1.381 (4)	C14—H14A	0.9600
C9—C8	1.382 (3)	C14—H14B	0.9600
C9—H9	0.9300	C14—H14C	0.9600
C1—C6	1.375 (3)	C6—H6	0.9300
C1—C2	1.381 (4)	C10—H10	0.9300

C7—N1—S1	123.91 (17)	C4—C3—C2	120.4 (2)
C7—N1—HN1	122 (3)	C4—C3—H3	119.8
S1—N1—HN1	114 (3)	C2—C3—H3	119.8
C11—O4—C14	118.2 (3)	C3—C4—C5	120.2 (2)
C12—C13—C8	120.1 (2)	C3—C4—H4	119.9
C12—C13—H13	119.9	C5—C4—H4	119.9
C8—C13—H13	119.9	C1—C2—C3	119.2 (2)
O3—C7—N1	120.0 (2)	C1—C2—H2	120.4
O3—C7—C8	123.6 (2)	C3—C2—H2	120.4
N1—C7—C8	116.42 (19)	O4—C14—H14A	109.5
C10—C9—C8	121.9 (2)	O4—C14—H14B	109.5
C10—C9—H9	119.1	H14A—C14—H14B	109.5
C8—C9—H9	119.1	O4—C14—H14C	109.5
C6—C1—C2	121.0 (2)	H14A—C14—H14C	109.5
C6—C1—S1	120.16 (18)	H14B—C14—H14C	109.5
C2—C1—S1	118.81 (18)	C1—C6—C5	118.7 (2)
C13—C12—C11	120.9 (2)	C1—C6—H6	120.6
C13—C12—H12	119.5	C5—C6—H6	120.6
C11—C12—H12	119.5	C11—C10—C9	119.1 (2)
C9—C8—C13	118.3 (2)	C11—C10—H10	120.4
C9—C8—C7	117.3 (2)	C9—C10—H10	120.4
C13—C8—C7	124.4 (2)	O2—S1—O1	119.44 (12)
O4—C11—C10	125.0 (2)	O2—S1—N1	103.74 (11)
O4—C11—C12	115.3 (2)	O1—S1—N1	109.21 (11)
C10—C11—C12	119.6 (2)	O2—S1—C1	108.88 (11)
C4—C5—C6	120.5 (2)	O1—S1—C1	108.65 (10)
C4—C5—H5	119.7	N1—S1—C1	106.11 (10)
C6—C5—H5	119.7

S1—N1—C7—O3	−10.3 (3)	S1—C1—C2—C3	179.0 (2)
S1—N1—C7—C8	169.94 (15)	C4—C3—C2—C1	−1.4 (4)
C8—C13—C12—C11	0.0 (3)	C2—C1—C6—C5	−1.2 (4)
C10—C9—C8—C13	1.0 (4)	S1—C1—C6—C5	−178.49 (18)
C10—C9—C8—C7	−179.8 (2)	C4—C5—C6—C1	0.4 (4)
C12—C13—C8—C9	−0.6 (3)	O4—C11—C10—C9	−178.6 (2)
C12—C13—C8—C7	−179.8 (2)	C12—C11—C10—C9	0.1 (4)
O3—C7—C8—C9	−2.4 (3)	C8—C9—C10—C11	−0.7 (4)
N1—C7—C8—C9	177.3 (2)	C7—N1—S1—O2	−177.30 (19)
O3—C7—C8—C13	176.8 (2)	C7—N1—S1—O1	−48.9 (2)
N1—C7—C8—C13	−3.5 (3)	C7—N1—S1—C1	68.0 (2)
C14—O4—C11—C10	−6.6 (4)	C6—C1—S1—O2	153.0 (2)
C14—O4—C11—C12	174.7 (3)	C2—C1—S1—O2	−24.3 (2)
C13—C12—C11—O4	179.0 (2)	C6—C1—S1—O1	21.4 (2)
C13—C12—C11—C10	0.2 (4)	C2—C1—S1—O1	−155.9 (2)
C2—C3—C4—C5	0.6 (4)	C6—C1—S1—N1	−95.9 (2)
C6—C5—C4—C3	−0.1 (4)	C2—C1—S1—N1	86.8 (2)
C6—C1—C2—C3	1.7 (4)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the methoxybenzene ring.

D—H···A	D—H	H···A	D···A	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.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the methoxybenzene ring.

D—H···A	D—H	H···A	D···A	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.

Acknowledgements

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

References

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