Literature DB >> 24764904

N-(4-Meth-oxy-benzo-yl)-2-methyl-benzene-sulfonamide.

S Sreenivasa1, B S Palakshamurthy2, S Madankumar3, N K Lokanath3, P A Suchetan4.   

Abstract

In the title compound, C15H15NO4S, the dihedral angle between the aromatic rings is 80.81 (1)° and the dihedral angle between the planes defined by the S-N-C=O fragment and the sulfonyl benzene ring is 86.34 (1)°. In the extended structure, dimers related by a crystallographic twofold axis are connected by pairs of both N-H⋯O hydrogen bonds and C-H⋯O inter-actions, which generate R 2 (2)(8) and R 2 (2)(14) loops, respectively. A weak aromatic π-π stacking inter-action is also observed [centroid-centroid separation = 3.7305 (3) Å].

Entities:  

Year:  2014        PMID： 24764904      PMCID： PMC3998343          DOI： 10.1107/S1600536814001354

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related structures, see: Gowda et al. (2010 ▶); Suchetan et al. (2010a ▶,b ▶, 2011 ▶); Sreenivasa et al. (2013 ▶, 2014 ▶).

Experimental

Crystal data

C15H15NO4S M = 305.34 Monoclinic, a = 21.807 (2) Å b = 7.3521 (8) Å c = 18.602 (2) Å β = 101.211 (3)° V = 2925.4 (5) Å3 Z = 8 Cu Kα radiation μ = 2.11 mm−1 T = 293 K 0.38 × 0.29 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.504, T max = 0.629 16411 measured reflections 2431 independent reflections 2174 reflections with I > 2σ(I) R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.122 S = 0.92 2431 reflections 196 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.34 e Å−3 Δρmin = −0.51 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus; 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. Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814001354/hb7188sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001354/hb7188Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814001354/hb7188Isup3.cml CCDC reference: Additional supporting information: crystallographic information; 3D view; checkCIF report
C15H15NO4SPrism
Mr = 305.34Dx = 1.387 Mg m−3
Monoclinic, C2/cMelting point: 447 K
Hall symbol: -C 2ycCu Kα radiation, λ = 1.54178 Å
a = 21.807 (2) ÅCell parameters from 25 reflections
b = 7.3521 (8) Åθ = 4.1–64.7°
c = 18.602 (2) ŵ = 2.11 mm−1
β = 101.211 (3)°T = 293 K
V = 2925.4 (5) Å3Prism, colourless
Z = 80.38 × 0.29 × 0.22 mm
F(000) = 1280
Bruker APEXII CCD diffractometer2431 independent reflections
Radiation source: fine-focus sealed tube2174 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
phi and φ scansθmax = 64.7°, θmin = 4.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −25→24
Tmin = 0.504, Tmax = 0.629k = −7→8
16411 measured reflectionsl = −20→21
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 0.92w = 1/[σ2(Fo2) + (0.0923P)2 + 2.3453P] where P = (Fo2 + 2Fc2)/3
2431 reflections(Δ/σ)max < 0.001
196 parametersΔρmax = 0.34 e Å−3
0 restraintsΔρmin = −0.51 e Å−3
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.
xyzUiso*/Ueq
H10.0708 (12)0.197 (3)0.2813 (15)0.051 (7)*
S10.02647 (2)0.20056 (7)0.37394 (2)0.0326 (2)
O2−0.02356 (6)0.2872 (2)0.32370 (7)0.0408 (4)
O10.01308 (8)0.0360 (2)0.40868 (8)0.0499 (4)
O30.15501 (7)0.0483 (2)0.41305 (7)0.0464 (4)
C80.17364 (9)0.0372 (3)0.29109 (9)0.0335 (4)
N10.07872 (7)0.1589 (2)0.32300 (8)0.0346 (4)
O40.28653 (7)−0.0475 (2)0.13921 (8)0.0512 (4)
C130.14633 (9)0.0201 (3)0.21740 (10)0.0395 (5)
H130.10310.02860.20310.047*
C60.07042 (10)0.2955 (3)0.51353 (10)0.0406 (5)
H60.06060.17640.52380.049*
C120.18241 (10)−0.0093 (3)0.16511 (10)0.0399 (5)
H120.1636−0.02040.11600.048*
C20.07397 (9)0.5358 (3)0.42381 (10)0.0372 (5)
C10.06024 (8)0.3584 (3)0.44137 (9)0.0317 (4)
C70.13675 (9)0.0789 (3)0.34846 (9)0.0341 (4)
C110.24672 (10)−0.0224 (3)0.18620 (10)0.0372 (5)
C100.27437 (10)−0.0116 (3)0.26017 (10)0.0439 (5)
H100.3175−0.02330.27460.053*
C30.09891 (10)0.6503 (3)0.48231 (12)0.0476 (5)
H30.10870.76990.47290.057*
C40.10915 (10)0.5888 (3)0.55374 (11)0.0488 (6)
H40.12570.66770.59170.059*
C90.23797 (10)0.0164 (3)0.31184 (10)0.0402 (5)
H90.25660.02140.36120.048*
C50.09543 (11)0.4140 (4)0.56954 (10)0.0484 (6)
H50.10290.37440.61790.058*
C140.06366 (13)0.6127 (3)0.34685 (11)0.0543 (6)
H14A0.08910.54790.31880.082*
H14B0.07490.73920.34890.082*
H14C0.02040.59990.32400.082*
C150.25999 (13)−0.0489 (5)0.06265 (12)0.0653 (8)
H15A0.2278−0.13980.05290.098*
H15B0.2920−0.07620.03540.098*
H15C0.24230.06820.04830.098*
U11U22U33U12U13U23
S10.0365 (3)0.0348 (3)0.0268 (3)−0.00716 (18)0.00702 (19)−0.00524 (15)
O20.0324 (7)0.0554 (10)0.0325 (6)0.0007 (6)0.0010 (5)−0.0104 (6)
O10.0681 (10)0.0406 (10)0.0444 (8)−0.0208 (8)0.0191 (7)−0.0039 (6)
O30.0543 (9)0.0550 (10)0.0273 (7)0.0034 (7)0.0017 (6)0.0049 (6)
C80.0386 (10)0.0296 (11)0.0303 (9)0.0028 (8)0.0019 (7)−0.0019 (7)
N10.0392 (9)0.0399 (10)0.0253 (7)0.0049 (7)0.0074 (6)0.0007 (6)
O40.0439 (8)0.0725 (12)0.0379 (7)0.0054 (8)0.0095 (6)−0.0081 (7)
C130.0351 (10)0.0450 (13)0.0345 (10)0.0073 (9)−0.0032 (8)−0.0057 (8)
C60.0489 (11)0.0422 (13)0.0307 (9)−0.0017 (9)0.0075 (8)−0.0004 (8)
C120.0430 (11)0.0445 (12)0.0287 (9)0.0080 (9)−0.0013 (7)−0.0074 (8)
C20.0403 (10)0.0341 (12)0.0357 (9)0.0005 (9)0.0034 (7)−0.0032 (8)
C10.0326 (9)0.0352 (11)0.0266 (8)−0.0011 (8)0.0046 (6)−0.0040 (7)
C70.0403 (10)0.0304 (11)0.0302 (9)−0.0022 (8)0.0035 (7)−0.0012 (7)
C110.0396 (10)0.0358 (12)0.0356 (9)0.0046 (8)0.0059 (8)−0.0039 (7)
C100.0332 (10)0.0562 (15)0.0388 (10)0.0049 (9)−0.0020 (8)−0.0069 (9)
C30.0514 (12)0.0351 (12)0.0534 (12)−0.0048 (10)0.0030 (9)−0.0116 (9)
C40.0499 (12)0.0511 (15)0.0420 (11)−0.0006 (11)0.0004 (9)−0.0205 (9)
C90.0414 (11)0.0449 (13)0.0301 (9)0.0061 (9)−0.0039 (7)−0.0031 (8)
C50.0545 (12)0.0619 (16)0.0267 (9)0.0014 (11)0.0027 (8)−0.0083 (9)
C140.0776 (16)0.0396 (14)0.0432 (11)−0.0074 (12)0.0051 (10)0.0074 (9)
C150.0629 (15)0.099 (2)0.0353 (11)0.0046 (15)0.0129 (10)−0.0059 (11)
S1—O11.4283 (15)C2—C11.391 (3)
S1—O21.4398 (14)C2—C31.399 (3)
S1—N11.6461 (16)C2—C141.515 (3)
S1—C11.7613 (18)C11—C101.393 (3)
O3—C71.211 (2)C10—C91.376 (3)
C8—C131.390 (2)C10—H100.9300
C8—C91.389 (3)C3—C41.380 (3)
C8—C71.488 (3)C3—H30.9300
N1—C71.392 (2)C4—C51.364 (4)
N1—H10.81 (3)C4—H40.9300
O4—C111.359 (2)C9—H90.9300
O4—C151.429 (3)C5—H50.9300
C13—C121.382 (3)C14—H14A0.9600
C13—H130.9300C14—H14B0.9600
C6—C51.386 (3)C14—H14C0.9600
C6—C11.396 (3)C15—H15A0.9600
C6—H60.9300C15—H15B0.9600
C12—C111.384 (3)C15—H15C0.9600
C12—H120.9300
O1—S1—O2118.20 (10)O4—C11—C12124.46 (17)
O1—S1—N1109.14 (9)O4—C11—C10115.78 (18)
O2—S1—N1103.34 (8)C12—C11—C10119.75 (18)
O1—S1—C1109.25 (9)C9—C10—C11120.05 (19)
O2—S1—C1109.27 (9)C9—C10—H10120.0
N1—S1—C1107.00 (8)C11—C10—H10120.0
C13—C8—C9118.68 (18)C4—C3—C2121.2 (2)
C13—C8—C7122.57 (18)C4—C3—H3119.4
C9—C8—C7118.75 (16)C2—C3—H3119.4
C7—N1—S1124.60 (13)C5—C4—C3120.98 (19)
C7—N1—H1118.8 (19)C5—C4—H4119.5
S1—N1—H1116.3 (19)C3—C4—H4119.5
C11—O4—C15117.14 (17)C10—C9—C8120.73 (17)
C12—C13—C8121.00 (18)C10—C9—H9119.6
C12—C13—H13119.5C8—C9—H9119.6
C8—C13—H13119.5C4—C5—C6120.05 (19)
C5—C6—C1118.7 (2)C4—C5—H5120.0
C5—C6—H6120.6C6—C5—H5120.0
C1—C6—H6120.6C2—C14—H14A109.5
C13—C12—C11119.69 (17)C2—C14—H14B109.5
C13—C12—H12120.2H14A—C14—H14B109.5
C11—C12—H12120.2C2—C14—H14C109.5
C1—C2—C3116.76 (18)H14A—C14—H14C109.5
C1—C2—C14124.95 (17)H14B—C14—H14C109.5
C3—C2—C14118.3 (2)O4—C15—H15A109.5
C2—C1—C6122.33 (17)O4—C15—H15B109.5
C2—C1—S1121.98 (13)H15A—C15—H15B109.5
C6—C1—S1115.67 (16)O4—C15—H15C109.5
O3—C7—N1121.18 (17)H15A—C15—H15C109.5
O3—C7—C8123.64 (18)H15B—C15—H15C109.5
N1—C7—C8115.18 (15)
O1—S1—N1—C7−55.03 (19)S1—N1—C7—C8174.04 (14)
O2—S1—N1—C7178.35 (16)C13—C8—C7—O3159.9 (2)
C1—S1—N1—C763.07 (19)C9—C8—C7—O3−20.8 (3)
C9—C8—C13—C12−2.7 (3)C13—C8—C7—N1−20.8 (3)
C7—C8—C13—C12176.6 (2)C9—C8—C7—N1158.54 (19)
C8—C13—C12—C110.1 (3)C15—O4—C11—C124.1 (3)
C3—C2—C1—C60.1 (3)C15—O4—C11—C10−176.6 (2)
C14—C2—C1—C6−179.6 (2)C13—C12—C11—O4−178.6 (2)
C3—C2—C1—S1178.06 (16)C13—C12—C11—C102.1 (3)
C14—C2—C1—S1−1.6 (3)O4—C11—C10—C9179.1 (2)
C5—C6—C1—C2−0.4 (3)C12—C11—C10—C9−1.6 (4)
C5—C6—C1—S1−178.41 (16)C1—C2—C3—C40.0 (3)
O1—S1—C1—C2−175.20 (16)C14—C2—C3—C4179.7 (2)
O2—S1—C1—C2−44.48 (18)C2—C3—C4—C50.2 (4)
N1—S1—C1—C266.76 (18)C11—C10—C9—C8−1.1 (4)
O1—S1—C1—C62.85 (18)C13—C8—C9—C103.2 (3)
O2—S1—C1—C6133.58 (15)C7—C8—C9—C10−176.1 (2)
N1—S1—C1—C6−115.18 (16)C3—C4—C5—C6−0.4 (3)
S1—N1—C7—O3−6.6 (3)C1—C6—C5—C40.5 (3)
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.81 (3)2.16 (3)2.917 (2)164 (3)
C13—H13···O2i0.932.563.288 (3)136
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1—H1⋯O2i 0.81 (3)2.16 (3)2.917 (2)164 (3)
C13—H13⋯O2i 0.932.563.288 (3)136

Symmetry code: (i) .

  7 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  N-Benzoyl-2-methyl-benzene-sulfonamide.

Authors:  P A Suchetan; B Thimme Gowda; Sabine Foro; Hartmut Fuess
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-04-02

3.  2-Methyl-N-(4-methyl-benzo-yl)benzene-sulfonamide.

Authors:  B Thimme Gowda; Sabine Foro; P A Suchetan; Hartmut Fuess
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-03-06

4.  N-(4-Chloro-benzo-yl)-2-methyl-benzene-sulfonamide.

Authors:  P A Suchetan; B Thimme Gowda; Sabine Foro; Hartmut Fuess
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-07-14

5.  2-Methyl-N-(4-nitro-benzo-yl)benzene-sulfonamide.

Authors:  P A Suchetan; Sabine Foro; B Thimme Gowda
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-03-19

6.  4-Meth-oxy-N-[(4-methyl-phen-yl)sulfon-yl]benzamide including an unknown solvate.

Authors:  Swamy Sreenivasa; Bandrehalli Siddagangaiah Palakshamurthy; Jagdish Tonannavar; Yenagi Jayashree; Achar Gurumurthy Sudha; Parameshwar Adimoole Suchetan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-10-19

7.  5-(3,5-Di-fluoro-phen-yl)-1-(4-fluoro-phen-yl)-3-tri-fluoro-methyl-1H-pyrazole.

Authors:  Karikere Ekanna Manoj Kumar; Parameshwar Adimoole Suchetan; Bandrehalli Siddagangaiah Palakshamurthy; Shankar Madan Kumar; Neratur Krishnappagowda Lokanath; Swamy Sreenivasa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-12-07
  7 in total
  1 in total

1.  Crystal structures of three N-(aryl-sulfon-yl)-4-fluoro-benzamides.

Authors:  P A Suchetan; S Naveen; N K Lokanath; K S Srivishnu; G M Supriya; H N Lakshmikantha
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2016-03-31
  1 in total

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