4-Meth­oxy-N-[(4-methyl­phen­yl)sulfon­yl]benzamide including an unknown solvate

Sreenivasa, S.; Palakshamurthy, B.S.; Tonannavar, J.; Jayashree, Y.; Sudha, A.G.; Suchetan, P.A.

doi:10.1107/S1600536813028158

organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Pages o1664-o1665

doi:10.1107/S1600536813028158

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4-Methoxy-N-[(4-methylphenyl)sulfonyl]benzamide including an unknown solvate

Swamy Sreenivasa,^a Bandrehalli Siddagangaiah Palakshamurthy,^b Jagdish Tonannavar,^c Yenagi Jayashree,^c Achar Gurumurthy Sudha ^d and Parameshwar Adimoole 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, ^cDepartment of Physics, Karnatak University, Dharwad, Karnataka 580 003, 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 12 September 2013; accepted 14 October 2013; online 19 October 2013)

In the title compound, C₁₅H₁₅NO₄S, the dihedral angle between the benzene rings is 78.62 (16)°. In the crystal, adjacent molecules are linked along the c axis into C(4) chains through strong N—H⋯O hydrogen bonds. Molecules are further connected through C—H⋯O hydrogen bonds into a hexameric unit generating an R⁶₆(66) motif. Another C—H⋯O interaction connects the molecules along the c axis, forming C(5) chains. A region of disordered electron density, most probably disordered methanol–water solvent molecules, was treated with the SQUEEZE routine in PLATON [Spek (2009 ). Acta Cryst. D65, 148–155]. The formula mass and unit-cell characteristics do not take into account this disordered solvent.

CCDC reference: 966286

Related literature

For similar structures, see: Gowda et al. (2009 ); Suchetan et al. (2010a ,b ,c , 2011 ); Sreenivasa et al. (2013 ). For details of the use of the SQUEEZE routine in PLATON, see: Spek (2009).

Experimental

Crystal data

C₁₅H₁₅NO₄S
M_r = 305.34
Trigonal, $[R \overline 3]$
a = 27.1686 (16) Å
c = 10.8594 (6) Å
V = 6941.8 (7) Å³
Z = 18
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.32 × 0.27 × 0.19 mm

Data collection

Bruker APEXII diffractometer
7701 measured reflections
2106 independent reflections
1604 reflections with I > 2σ(I)
R_int = 0.031
θ_max = 22.9°

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.109
S = 1.06
2106 reflections
196 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3ⁱ	0.82 (2)	2.26 (2)	3.038 (3)	160 (3)
N1—H1N⋯O2ⁱ	0.82 (2)	2.59 (3)	3.140 (3)	126 (2)
C10—H10⋯O3ⁱ	0.93	2.58	3.249 (3)	129
C15—H15A⋯O1ⁱⁱ	0.96	2.56	3.454 (4)	154
Symmetry codes: (i) $[-x+y+{\script{1\over 3}}, -x+{\script{5\over 3}}, z-{\script{1\over 3}}]$ ; (ii) $[x-y+{\script{2\over 3}}, x+{\script{1\over 3}}, -z+{\script{1\over 3}}]$ .

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: 966286

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813028158/su2649sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813028158/su2649Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813028158/su2649Isup3.cml

checkCIF report

Comment top

As a part of our continued efforts to study the crystal structures of N-(aroyl)-arylsulfonamides (Sreenivasa et al., 2013 and), we report herein on the crystal structure of the title compound.

In the title compound, Fig. 1, the dihedral angle between the benzene rings is 78.62 (16) °. This is similar to the value of 80.3 (1) ° in N-benzoylbenzenesulfonamide (Gowda et al., 2009), 79.4 (1) ° in N-benzoyl-4-methylbenzenesulfonamide (Suchetan et al., 2010a), and 81.0 (1) ° and 76.3 (1) ° in the two independent molecules of N-(4-Chloro-benzoyl)-4-methylbenzenesulfonamide (Suchetan et al., 2010b). Interestingly, in 4-methyl-N-(4-methylbenzoyl)benzenesulfonamide (Suchetan et al., 2010c) the angle is much larger, 89.0 (1) °, similar to the value of 89.8 (1) ° in 4-Methyl-N-(4-nitrobenzoyl)benzenesulfonamide (Suchetan et al., 2011), and 88.9 (1) ° in N-(3-Methoxybenzoyl)-4-methylbenzenesulfonamide (Sreenivasa et al., 2013).

In the crystal, adjacent molecules are linked along the c axis into C(4) chains via N—H···O hydrogen bonds (Table 1 and Fig. 2). Molecules are also connected through C—H···O hydrogen bonds into a hexameric unit generating an R⁶₆(66) motif (Table 1 and Fig. 3). Further C—H···O hydrogen bonds connect the molecules along the c axis forming C(5) chains (Table 1 and Fig. 4).

Related literature top

For similar structures, see: Gowda et al. (2009); Suchetan et al. (2010a,b,c, 2011); Sreenivasa et al. (2013). For details of the use of the SQUEEZE routine in PLATON, see: Spek (2009).

Experimental top

The title compound was prepared by refluxing a mixture of 4-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 then re-precipitated by acidifying the filtered solution with dilute HCl. The compound obtained was filtered and then dried (M.p. = 393 K). Colourless prism-like crystals of the title compound were obtained by slow evaporation of an water/methanol solution (1:1) 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. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view along the b axis of the crystal packing of the title compound, with hydrogen bonds shown as dashed lines (see Table 1 for details; C bound hydrogen atoms have been omitted for clarity).
	Fig. 3. A view of the hexameric C—H···O hydrogen bonded R⁶₆(66) ring motif in the crystal structure of the title compound (see Table 1 for details; H atoms not involved in these hydrogen bonds have been omitted for clarity).
	Fig. 4. A view of the C—H···O hydrogen bonds linking molecules to form C(5) chains in the crystal structure of the title compound (see Table 1 for details; H atoms not involved in these hydrogen bonds have been omitted for clarity).

4-Methoxy-N-[(4-methylphenyl)sulfonyl]benzamide top

Crystal data top

C₁₅H₁₅NO₄S	D_x = 1.315 Mg m⁻³
M_r = 305.34	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 1123 reflections
Hall symbol: -R 3	θ = 0.0–22.9°
a = 27.1686 (16) Å	µ = 0.22 mm⁻¹
c = 10.8594 (6) Å	T = 293 K
V = 6941.8 (7) Å³	Prism, colourless
Z = 18	0.32 × 0.27 × 0.19 mm
F(000) = 2880

Data collection top

Bruker APEXII diffractometer	1604 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 22.9°, θ_min = 1.5°
phi and ω scans	h = −28→27
7701 measured reflections	k = −29→27
2106 independent reflections	l = −11→11

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) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.050P)² + 5.9239P] where P = (F_o² + 2F_c²)/3
2106 reflections	(Δ/σ)_max = 0.001
196 parameters	Δρ_max = 0.17 e Å⁻³
1 restraint	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₅H₁₅NO₄S	Z = 18
M_r = 305.34	Mo Kα radiation
Trigonal, R3	µ = 0.22 mm⁻¹
a = 27.1686 (16) Å	T = 293 K
c = 10.8594 (6) Å	0.32 × 0.27 × 0.19 mm
V = 6941.8 (7) Å³

Data collection top

Bruker APEXII diffractometer	1604 reflections with I > 2σ(I)
7701 measured reflections	R_int = 0.031
2106 independent reflections	θ_max = 22.9°

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.17 e Å⁻³
2106 reflections	Δρ_min = −0.31 e Å⁻³
196 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	Occ. (<1)
S1	0.64344 (3)	0.92841 (3)	0.07169 (6)	0.0512 (3)
O2	0.67632 (8)	0.92727 (8)	0.17255 (17)	0.0630 (6)
O3	0.58608 (8)	0.93575 (8)	0.29224 (17)	0.0589 (6)
C9	0.57569 (10)	1.01361 (10)	0.2290 (2)	0.0408 (6)
N1	0.61811 (10)	0.97065 (10)	0.1035 (2)	0.0485 (6)
H1N	0.6281 (12)	0.9968 (9)	0.055 (2)	0.062 (10)*
O1	0.66938 (8)	0.94701 (8)	−0.04522 (17)	0.0632 (6)
O4	0.52572 (9)	1.13258 (9)	0.2828 (2)	0.0741 (7)
C8	0.59338 (10)	0.97057 (11)	0.2137 (2)	0.0432 (7)
C10	0.57316 (11)	1.04599 (11)	0.1330 (2)	0.0492 (7)
H10	0.5831	1.0413	0.0538	0.059*
C12	0.54143 (11)	1.09243 (11)	0.2710 (3)	0.0504 (7)
C14	0.56081 (11)	1.02166 (11)	0.3456 (2)	0.0506 (7)
H14	0.5625	1.0004	0.4107	0.061*
C11	0.55601 (12)	1.08497 (12)	0.1542 (3)	0.0555 (8)
H11	0.5543	1.1064	0.0893	0.067*
C13	0.54340 (11)	1.06075 (12)	0.3676 (3)	0.0543 (8)
H13	0.5332	1.0655	0.4465	0.065*
C1	0.58283 (12)	0.86088 (12)	0.0570 (2)	0.0506 (7)
C3	0.53039 (16)	0.76272 (14)	0.1127 (3)	0.0733 (9)
H3	0.5270	0.7326	0.1598	0.088*
C6	0.54185 (13)	0.85199 (13)	−0.0290 (3)	0.0591 (8)
H6	0.5458	0.8817	−0.0784	0.071*
C2	0.57735 (14)	0.81618 (14)	0.1276 (3)	0.0640 (9)
H2	0.6052	0.8220	0.1850	0.077*
C5	0.49512 (14)	0.79869 (14)	−0.0406 (3)	0.0689 (9)
H5	0.4670	0.7929	−0.0972	0.083*
C4	0.48878 (14)	0.75366 (14)	0.0291 (3)	0.0678 (9)
C15	0.50425 (16)	1.13869 (16)	0.3982 (3)	0.0871 (11)
H15A	0.4715	1.1032	0.4206	0.131*
H15B	0.4938	1.1675	0.3915	0.131*
H15C	0.5330	1.1495	0.4602	0.131*
C7	0.43705 (17)	0.69489 (15)	0.0145 (4)	0.1057 (14)
H7A	0.4150	0.6948	−0.0546	0.159*	0.50
H7B	0.4143	0.6851	0.0878	0.159*	0.50
H7C	0.4491	0.6676	0.0011	0.159*	0.50
H7D	0.4373	0.6702	0.0775	0.159*	0.50
H7E	0.4380	0.6799	−0.0649	0.159*	0.50
H7F	0.4031	0.6974	0.0218	0.159*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0582 (5)	0.0608 (5)	0.0468 (5)	0.0389 (4)	0.0014 (4)	−0.0045 (3)
O2	0.0687 (13)	0.0786 (14)	0.0612 (13)	0.0515 (12)	−0.0164 (10)	−0.0147 (11)
O3	0.0789 (14)	0.0686 (13)	0.0476 (12)	0.0506 (11)	0.0087 (10)	0.0122 (10)
C9	0.0383 (15)	0.0458 (15)	0.0404 (15)	0.0226 (13)	−0.0015 (12)	−0.0007 (12)
N1	0.0642 (16)	0.0548 (15)	0.0397 (14)	0.0396 (13)	0.0062 (12)	0.0032 (12)
O1	0.0702 (13)	0.0730 (13)	0.0552 (13)	0.0423 (11)	0.0176 (11)	0.0014 (10)
O4	0.0859 (15)	0.0791 (15)	0.0861 (17)	0.0629 (14)	−0.0009 (12)	−0.0053 (12)
C8	0.0431 (16)	0.0488 (17)	0.0395 (16)	0.0243 (14)	−0.0013 (13)	−0.0007 (13)
C10	0.0507 (17)	0.0638 (19)	0.0421 (16)	0.0353 (15)	0.0030 (13)	0.0049 (14)
C12	0.0429 (16)	0.0537 (18)	0.063 (2)	0.0305 (14)	−0.0057 (14)	−0.0041 (15)
C14	0.0595 (18)	0.0636 (18)	0.0401 (16)	0.0394 (16)	0.0035 (14)	0.0045 (14)
C11	0.0605 (18)	0.068 (2)	0.0528 (19)	0.0431 (17)	0.0042 (14)	0.0140 (15)
C13	0.0551 (18)	0.070 (2)	0.0477 (17)	0.0385 (16)	0.0015 (14)	−0.0099 (15)
C1	0.0648 (19)	0.0591 (18)	0.0426 (16)	0.0421 (16)	0.0018 (14)	−0.0019 (14)
C3	0.100 (3)	0.059 (2)	0.067 (2)	0.045 (2)	0.007 (2)	0.0091 (17)
C6	0.069 (2)	0.062 (2)	0.0522 (19)	0.0367 (18)	−0.0046 (16)	0.0035 (15)
C2	0.085 (2)	0.073 (2)	0.0542 (19)	0.054 (2)	−0.0054 (17)	−0.0012 (17)
C5	0.067 (2)	0.074 (2)	0.064 (2)	0.0334 (19)	−0.0101 (17)	−0.0020 (18)
C4	0.075 (2)	0.061 (2)	0.063 (2)	0.0308 (18)	0.0086 (18)	0.0005 (17)
C15	0.099 (3)	0.102 (3)	0.094 (3)	0.076 (2)	−0.005 (2)	−0.030 (2)
C7	0.102 (3)	0.075 (3)	0.107 (3)	0.019 (2)	0.015 (2)	0.003 (2)

Geometric parameters (Å, º) top

S1—O1	1.4169 (19)	C1—C6	1.379 (4)
S1—O2	1.4235 (19)	C1—C2	1.380 (4)
S1—N1	1.643 (2)	C3—C4	1.373 (4)
S1—C1	1.756 (3)	C3—C2	1.382 (4)
O3—C8	1.214 (3)	C3—H3	0.9300
C9—C14	1.380 (3)	C6—C5	1.373 (4)
C9—C10	1.388 (3)	C6—H6	0.9300
C9—C8	1.479 (4)	C2—H2	0.9300
N1—C8	1.372 (3)	C5—C4	1.374 (4)
N1—H1N	0.817 (17)	C5—H5	0.9300
O4—C12	1.362 (3)	C4—C7	1.519 (5)
O4—C15	1.427 (4)	C15—H15A	0.9600
C10—C11	1.373 (4)	C15—H15B	0.9600
C10—H10	0.9300	C15—H15C	0.9600
C12—C11	1.374 (4)	C7—H7A	0.9600
C12—C13	1.375 (4)	C7—H7B	0.9600
C14—C13	1.382 (4)	C7—H7C	0.9600
C14—H14	0.9300	C7—H7D	0.9600
C11—H11	0.9300	C7—H7E	0.9600
C13—H13	0.9300	C7—H7F	0.9600

O1—S1—O2	119.45 (13)	C5—C6—H6	120.4
O1—S1—N1	104.29 (12)	C1—C6—H6	120.4
O2—S1—N1	109.86 (11)	C1—C2—C3	119.8 (3)
O1—S1—C1	109.32 (12)	C1—C2—H2	120.1
O2—S1—C1	108.53 (13)	C3—C2—H2	120.1
N1—S1—C1	104.33 (13)	C6—C5—C4	121.7 (3)
C14—C9—C10	118.5 (2)	C6—C5—H5	119.1
C14—C9—C8	117.7 (2)	C4—C5—H5	119.1
C10—C9—C8	123.8 (2)	C3—C4—C5	118.6 (3)
C8—N1—S1	123.9 (2)	C3—C4—C7	120.2 (3)
C8—N1—H1N	121 (2)	C5—C4—C7	121.1 (3)
S1—N1—H1N	113 (2)	O4—C15—H15A	109.5
C12—O4—C15	119.1 (2)	O4—C15—H15B	109.5
O3—C8—N1	120.2 (2)	H15A—C15—H15B	109.5
O3—C8—C9	123.1 (2)	O4—C15—H15C	109.5
N1—C8—C9	116.7 (2)	H15A—C15—H15C	109.5
C11—C10—C9	120.5 (3)	H15B—C15—H15C	109.5
C11—C10—H10	119.8	C4—C7—H7A	109.5
C9—C10—H10	119.8	C4—C7—H7B	109.5
O4—C12—C11	115.7 (3)	H7A—C7—H7B	109.5
O4—C12—C13	123.8 (3)	C4—C7—H7C	109.5
C11—C12—C13	120.5 (2)	H7A—C7—H7C	109.5
C9—C14—C13	121.4 (3)	H7B—C7—H7C	109.5
C9—C14—H14	119.3	C4—C7—H7D	109.5
C13—C14—H14	119.3	H7A—C7—H7D	141.1
C10—C11—C12	120.2 (3)	H7B—C7—H7D	56.3
C10—C11—H11	119.9	H7C—C7—H7D	56.3
C12—C11—H11	119.9	C4—C7—H7E	109.5
C12—C13—C14	119.0 (3)	H7A—C7—H7E	56.3
C12—C13—H13	120.5	H7B—C7—H7E	141.1
C14—C13—H13	120.5	H7C—C7—H7E	56.3
C6—C1—C2	120.0 (3)	H7D—C7—H7E	109.5
C6—C1—S1	119.9 (2)	C4—C7—H7F	109.5
C2—C1—S1	120.1 (2)	H7A—C7—H7F	56.3
C4—C3—C2	120.7 (3)	H7B—C7—H7F	56.3
C4—C3—H3	119.7	H7C—C7—H7F	141.1
C2—C3—H3	119.7	H7D—C7—H7F	109.5
C5—C6—C1	119.1 (3)	H7E—C7—H7F	109.5

O1—S1—N1—C8	−174.5 (2)	C11—C12—C13—C14	0.6 (4)
O2—S1—N1—C8	−45.3 (3)	C9—C14—C13—C12	−0.5 (4)
C1—S1—N1—C8	70.9 (2)	O1—S1—C1—C6	−52.8 (2)
S1—N1—C8—O3	−4.4 (4)	O2—S1—C1—C6	175.4 (2)
S1—N1—C8—C9	176.81 (18)	N1—S1—C1—C6	58.3 (2)
C14—C9—C8—O3	13.2 (4)	O1—S1—C1—C2	124.4 (2)
C10—C9—C8—O3	−166.6 (3)	O2—S1—C1—C2	−7.4 (3)
C14—C9—C8—N1	−168.0 (2)	N1—S1—C1—C2	−124.5 (2)
C10—C9—C8—N1	12.1 (4)	C2—C1—C6—C5	1.8 (4)
C14—C9—C10—C11	−0.2 (4)	S1—C1—C6—C5	179.0 (2)
C8—C9—C10—C11	179.7 (2)	C6—C1—C2—C3	−0.7 (4)
C15—O4—C12—C11	173.4 (3)	S1—C1—C2—C3	−177.9 (2)
C15—O4—C12—C13	−6.9 (4)	C4—C3—C2—C1	−0.6 (5)
C10—C9—C14—C13	0.3 (4)	C1—C6—C5—C4	−1.6 (5)
C8—C9—C14—C13	−179.5 (2)	C2—C3—C4—C5	0.8 (5)
C9—C10—C11—C12	0.3 (4)	C2—C3—C4—C7	−179.3 (3)
O4—C12—C11—C10	179.2 (2)	C6—C5—C4—C3	0.3 (5)
C13—C12—C11—C10	−0.5 (4)	C6—C5—C4—C7	−179.6 (3)
O4—C12—C13—C14	−179.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.82 (2)	2.26 (2)	3.038 (3)	160 (3)
N1—H1N···O2ⁱ	0.82 (2)	2.59 (3)	3.140 (3)	126 (2)
C10—H10···O3ⁱ	0.93	2.58	3.249 (3)	129
C15—H15A···O1ⁱⁱ	0.96	2.56	3.454 (4)	154

Symmetry codes: (i) −x+y+1/3, −x+5/3, z−1/3; (ii) x−y+2/3, x+1/3, −z+1/3.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.817 (17)	2.257 (19)	3.038 (3)	160 (3)
N1—H1N···O2ⁱ	0.817 (17)	2.59 (3)	3.140 (3)	126 (2)
C10—H10···O3ⁱ	0.93	2.58	3.249 (3)	129
C15—H15A···O1ⁱⁱ	0.96	2.56	3.454 (4)	154

Symmetry codes: (i) −x+y+1/3, −x+5/3, z−1/3; (ii) x−y+2/3, x+1/3, −z+1/3.

Acknowledgements

PAS thanks the University Grants Commission (UGC), India, for financial support under its Minor Research Project scheme. JT thanks the Department of Science and Technology (DST), New Delhi, for the SCXRD facility under the PURSE Grant (SR/S9/Z-23/2008/11, 2009) at USIC, Karnatak University.

References

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Volume 69| Part 11| November 2013| Pages o1664-o1665

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

4-Meth­­oxy-N-[(4-methyl­phen­yl)sulfon­yl]benzamide including an unknown solvate

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Experimental

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Refinement

Supporting information

Acknowledgements

References

organic compounds

4-Methoxy-N-[(4-methylphenyl)sulfonyl]benzamide including an unknown solvate