Literature DB >> 21836982

2-(4-Acetamido-benzene-sulfonamido)-benzoic acid.

Shahzad Sharif, Islam Ullah Khan, Tariq Mahmood, Sung Kwon Kang.   

Abstract

In the title compound, C(15)H(14)N(2)O(5)S, two similar mol-ecules comprise the asymmetric unit, which are linked by strong inter-molecular C-H⋯π inter-actions. Both mol-ecules are bent, with dihedral angles of 71.94 (16) and 74.62 (15)° between the benzene rings. An intra-molecular N-H⋯O hydrogen bond occurs in each mol-ecule. In the crystal, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Entities:  

Year:  2011        PMID: 21836982      PMCID: PMC3151891          DOI: 10.1107/S1600536811020307

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


Related literature

For our previous studies on sulfonamide derivatives, see: Khan et al. (2011 ▶); Sharif et al. (2010 ▶). For background to the pharmacological use of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶).

Experimental

Crystal data

C15H14N2O5S M = 334.34 Monoclinic, a = 9.3721 (19) Å b = 13.036 (3) Å c = 13.132 (3) Å β = 109.47 (3)° V = 1512.7 (5) Å3 Z = 4 Mo Kα radiation μ = 0.24 mm−1 T = 296 K 0.25 × 0.12 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.92, T max = 0.931 2926 measured reflections 2926 independent reflections 1470 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.045 wR(F 2) = 0.092 S = 0.82 2926 reflections 415 parameters 1 restraint H-atom parameters constrained Δρmax = 0.26 e Å−3 Δρmin = −0.24 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811020307/tk2747sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020307/tk2747Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811020307/tk2747Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H14N2O5SF(000) = 696
Mr = 334.34Dx = 1.468 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1295 reflections
a = 9.3721 (19) Åθ = 2.8–18.7°
b = 13.036 (3) ŵ = 0.24 mm1
c = 13.132 (3) ÅT = 296 K
β = 109.47 (3)°Block, violet
V = 1512.7 (5) Å30.25 × 0.12 × 0.09 mm
Z = 4
Bruker APEXII CCD diffractometer2926 independent reflections
graphite1470 reflections with I > 2σ(I)
φ and ω scansθmax = 25.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −11→10
Tmin = 0.92, Tmax = 0.931k = 0→15
2926 measured reflectionsl = 0→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 0.82w = 1/[σ2(Fo2) + (0.0338P)2] where P = (Fo2 + 2Fc2)/3
2926 reflections(Δ/σ)max < 0.001
415 parametersΔρmax = 0.26 e Å3
1 restraintΔρmin = −0.24 e Å3
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
C10.9116 (7)0.1951 (5)0.4462 (5)0.0489 (17)
C20.8856 (6)0.1876 (4)0.3361 (5)0.0378 (15)
C30.9664 (8)0.2491 (5)0.2895 (6)0.069 (2)
H30.94890.24330.21570.082*
C41.0705 (8)0.3179 (6)0.3474 (7)0.068 (2)
H41.1240.35850.31430.081*
C51.0948 (8)0.3260 (6)0.4565 (7)0.078 (2)
H51.16450.37360.49720.094*
C61.0181 (8)0.2652 (6)0.5064 (6)0.0547 (18)
H61.03740.2710.58040.066*
C70.8274 (7)0.1297 (5)0.4990 (5)0.0444 (16)
O80.7297 (6)0.0692 (4)0.4533 (4)0.0761 (16)
O90.8716 (5)0.1415 (4)0.6050 (4)0.0753 (14)
H90.82110.10430.630.113*
N100.7746 (6)0.1191 (4)0.2728 (4)0.0556 (15)
H100.76570.06130.30170.067*
S110.6629 (2)0.13965 (13)0.15141 (13)0.0496 (5)
O120.5537 (5)0.0600 (3)0.1345 (3)0.0650 (13)
O130.7415 (4)0.1479 (3)0.0766 (3)0.0601 (12)
C140.5771 (6)0.2586 (5)0.1545 (5)0.0409 (16)
C150.5660 (7)0.3302 (5)0.0747 (5)0.0505 (18)
H150.61110.31830.02250.061*
C160.4882 (7)0.4181 (5)0.0734 (5)0.0523 (19)
H160.480.46630.01960.063*
C170.4204 (6)0.4379 (5)0.1504 (5)0.0374 (15)
C180.4315 (7)0.3678 (5)0.2282 (5)0.0485 (18)
H180.38730.38090.28060.058*
C190.5082 (7)0.2768 (5)0.2307 (5)0.0479 (17)
H190.51340.2280.28340.057*
N200.3395 (5)0.5312 (4)0.1386 (4)0.0434 (13)
H200.33620.56680.08270.052*
C210.2673 (6)0.5729 (5)0.2010 (5)0.0411 (16)
O220.2672 (5)0.5316 (3)0.2864 (3)0.0580 (13)
C230.1884 (7)0.6728 (4)0.1635 (5)0.059 (2)
H23A0.20150.69250.09670.088*
H23B0.23070.72460.2170.088*
H23C0.08250.66530.15270.088*
C24−0.0124 (7)0.9059 (5)0.1004 (5)0.0449 (16)
C250.0910 (7)0.9800 (5)0.1592 (5)0.0437 (17)
C260.1722 (7)1.0380 (5)0.1075 (6)0.061 (2)
H260.23611.090.14490.074*
C270.1581 (7)1.0185 (6)0.0021 (6)0.064 (2)
H270.21371.0569−0.03120.077*
C280.0617 (8)0.9422 (6)−0.0555 (6)0.071 (2)
H280.05530.9272−0.12610.085*
C29−0.0240 (7)0.8892 (5)−0.0065 (6)0.0510 (18)
H29−0.09240.8405−0.04630.061*
C30−0.1013 (7)0.8458 (5)0.1504 (6)0.0479 (17)
O31−0.1843 (5)0.7725 (4)0.0872 (4)0.0677 (14)
H31−0.23130.74130.120.101*
O32−0.1066 (5)0.8583 (4)0.2407 (4)0.0691 (15)
N330.1094 (5)0.9963 (4)0.2685 (4)0.0555 (15)
H330.02950.99650.28690.067*
S340.2731 (2)1.01499 (13)0.36347 (14)0.0574 (5)
O350.3439 (5)1.1036 (3)0.3377 (4)0.0690 (14)
O360.2365 (5)1.0137 (4)0.4614 (3)0.0713 (13)
C370.3874 (7)0.9084 (5)0.3622 (5)0.0471 (17)
C380.4644 (7)0.9058 (5)0.2911 (6)0.059 (2)
H380.45760.96160.24570.07*
C390.5520 (7)0.8235 (6)0.2842 (6)0.0584 (19)
H390.60530.82340.23580.07*
C400.5584 (7)0.7408 (5)0.3516 (5)0.0498 (18)
C410.4833 (7)0.7435 (5)0.4263 (5)0.0540 (19)
H410.49120.68890.47330.065*
C420.3979 (7)0.8271 (5)0.4301 (5)0.0530 (18)
H420.34620.82890.47940.064*
N430.6463 (5)0.6529 (4)0.3513 (4)0.0563 (15)
H430.67010.61610.40890.068*
C440.6993 (7)0.6179 (6)0.2710 (6)0.0548 (19)
O450.6655 (5)0.6604 (4)0.1829 (4)0.0682 (14)
C460.7926 (7)0.5216 (6)0.2971 (5)0.071 (2)
H46A0.80450.50040.36950.106*
H46B0.89030.53450.2910.106*
H46C0.74260.46840.24750.106*
U11U22U33U12U13U23
C10.055 (4)0.049 (5)0.045 (4)0.016 (4)0.019 (4)0.011 (4)
C20.038 (4)0.027 (4)0.051 (4)0.014 (3)0.019 (4)0.012 (4)
C30.077 (6)0.060 (5)0.071 (6)−0.005 (4)0.027 (5)0.003 (4)
C40.050 (5)0.063 (6)0.081 (6)−0.001 (4)0.009 (5)0.017 (5)
C50.063 (6)0.059 (6)0.094 (7)−0.003 (4)0.002 (5)0.006 (5)
C60.049 (4)0.051 (5)0.057 (5)−0.004 (4)0.007 (4)0.004 (4)
C70.050 (4)0.048 (4)0.035 (4)0.010 (4)0.013 (3)0.004 (4)
O80.091 (4)0.081 (4)0.056 (3)−0.030 (3)0.023 (3)0.005 (3)
O90.083 (4)0.088 (4)0.054 (3)−0.007 (3)0.022 (3)0.003 (3)
N100.081 (4)0.034 (3)0.046 (3)0.006 (3)0.014 (3)0.008 (3)
S110.0681 (12)0.0425 (11)0.0387 (10)−0.0015 (10)0.0186 (9)−0.0069 (9)
O120.101 (4)0.038 (3)0.063 (3)−0.023 (3)0.038 (3)−0.013 (2)
O130.079 (3)0.056 (3)0.057 (3)−0.001 (3)0.038 (3)−0.010 (3)
C140.044 (4)0.036 (4)0.041 (4)0.002 (3)0.011 (3)0.001 (3)
C150.073 (5)0.053 (5)0.038 (4)0.003 (4)0.035 (4)0.007 (4)
C160.065 (5)0.054 (5)0.040 (4)0.011 (4)0.020 (4)0.015 (3)
C170.041 (4)0.033 (4)0.039 (4)0.001 (3)0.014 (3)0.002 (3)
C180.055 (4)0.052 (5)0.051 (4)0.010 (3)0.033 (4)0.018 (4)
C190.064 (4)0.052 (5)0.033 (4)−0.004 (4)0.023 (4)0.013 (4)
N200.051 (3)0.048 (4)0.037 (3)0.004 (3)0.023 (3)0.012 (3)
C210.043 (4)0.042 (4)0.034 (4)−0.011 (3)0.006 (3)−0.005 (3)
O220.077 (3)0.058 (3)0.051 (3)0.004 (3)0.036 (3)0.001 (3)
C230.069 (5)0.052 (5)0.052 (4)0.014 (4)0.017 (4)−0.008 (4)
C240.043 (4)0.048 (4)0.045 (4)0.004 (3)0.016 (3)0.011 (4)
C250.046 (4)0.048 (5)0.042 (4)0.013 (3)0.020 (4)0.009 (3)
C260.065 (5)0.061 (5)0.058 (5)−0.001 (4)0.022 (4)−0.004 (4)
C270.065 (5)0.064 (6)0.063 (5)0.008 (4)0.023 (4)0.026 (5)
C280.068 (5)0.089 (7)0.053 (5)−0.002 (5)0.017 (4)0.008 (5)
C290.055 (5)0.056 (5)0.043 (4)0.007 (4)0.017 (4)0.004 (4)
C300.052 (5)0.046 (5)0.048 (5)0.013 (4)0.021 (4)0.010 (4)
O310.071 (3)0.070 (3)0.064 (3)−0.015 (3)0.025 (3)−0.010 (3)
O320.080 (4)0.076 (4)0.065 (3)−0.010 (3)0.041 (3)0.000 (3)
N330.051 (3)0.070 (4)0.046 (3)0.009 (3)0.016 (3)−0.011 (3)
S340.0712 (13)0.0507 (13)0.0499 (11)−0.0118 (10)0.0194 (10)−0.0137 (10)
O350.088 (4)0.042 (3)0.079 (3)−0.022 (3)0.029 (3)−0.008 (3)
O360.101 (4)0.064 (3)0.056 (3)−0.014 (3)0.037 (3)−0.017 (3)
C370.055 (5)0.047 (5)0.038 (4)−0.011 (3)0.013 (4)−0.002 (4)
C380.064 (5)0.052 (5)0.062 (5)−0.010 (4)0.024 (4)0.024 (4)
C390.052 (5)0.067 (5)0.062 (5)0.007 (4)0.027 (4)0.026 (4)
C400.041 (4)0.065 (5)0.045 (4)−0.001 (4)0.015 (4)0.008 (4)
C410.058 (5)0.065 (6)0.038 (4)−0.002 (4)0.014 (4)0.010 (4)
C420.063 (5)0.059 (5)0.042 (4)−0.004 (4)0.025 (4)−0.012 (4)
N430.058 (4)0.062 (4)0.045 (3)0.003 (3)0.012 (3)0.019 (3)
C440.047 (4)0.066 (6)0.048 (5)−0.021 (4)0.013 (4)−0.005 (4)
O450.098 (4)0.065 (4)0.050 (3)−0.020 (3)0.036 (3)−0.006 (3)
C460.057 (5)0.084 (6)0.066 (5)0.004 (5)0.014 (4)−0.015 (5)
C1—C21.387 (8)C24—C291.389 (8)
C1—C61.389 (9)C24—C251.403 (8)
C1—C71.482 (8)C24—C301.450 (8)
C2—C31.379 (8)C25—C261.399 (8)
C2—N101.412 (7)C25—N331.402 (7)
C3—C41.356 (9)C26—C271.370 (8)
C3—H30.93C26—H260.93
C4—C51.378 (9)C27—C281.386 (9)
C4—H40.93C27—H270.93
C5—C61.374 (9)C28—C291.372 (9)
C5—H50.93C28—H280.93
C6—H60.93C29—H290.93
C7—O81.206 (7)C30—O321.215 (7)
C7—O91.322 (7)C30—O311.332 (8)
O9—H90.82O31—H310.82
N10—S111.611 (5)N33—S341.641 (5)
N10—H100.86N33—H330.86
S11—O131.415 (4)S34—O351.429 (4)
S11—O121.423 (4)S34—O361.438 (4)
S11—C141.754 (6)S34—C371.758 (7)
C14—C191.380 (7)C37—C381.358 (8)
C14—C151.382 (8)C37—C421.366 (8)
C15—C161.355 (8)C38—C391.371 (9)
C15—H150.93C38—H380.93
C16—C171.386 (7)C39—C401.383 (8)
C16—H160.93C39—H390.93
C17—C181.348 (8)C40—C411.385 (8)
C17—N201.414 (7)C40—N431.412 (7)
C18—C191.382 (8)C41—C421.363 (8)
C18—H180.93C41—H410.93
C19—H190.93C42—H420.93
N20—C211.340 (7)N43—C441.385 (8)
N20—H200.86N43—H430.86
C21—O221.244 (6)C44—O451.224 (7)
C21—C231.497 (8)C44—C461.503 (9)
C23—H23A0.96C46—H46A0.96
C23—H23B0.96C46—H46B0.96
C23—H23C0.96C46—H46C0.96
C2—C1—C6118.9 (7)C29—C24—C25118.1 (6)
C2—C1—C7120.8 (6)C29—C24—C30120.7 (7)
C6—C1—C7120.3 (7)C25—C24—C30121.2 (6)
C3—C2—C1119.3 (6)C26—C25—N33120.9 (6)
C3—C2—N10120.8 (6)C26—C25—C24119.5 (6)
C1—C2—N10119.8 (6)N33—C25—C24119.6 (6)
C4—C3—C2122.3 (7)C27—C26—C25120.4 (6)
C4—C3—H3118.9C27—C26—H26119.8
C2—C3—H3118.9C25—C26—H26119.8
C3—C4—C5118.2 (8)C26—C27—C28120.7 (7)
C3—C4—H4120.9C26—C27—H27119.7
C5—C4—H4120.9C28—C27—H27119.7
C6—C5—C4121.3 (7)C29—C28—C27118.8 (7)
C6—C5—H5119.3C29—C28—H28120.6
C4—C5—H5119.3C27—C28—H28120.6
C5—C6—C1119.9 (7)C28—C29—C24122.4 (7)
C5—C6—H6120.1C28—C29—H29118.8
C1—C6—H6120.1C24—C29—H29118.8
O8—C7—O9121.3 (6)O32—C30—O31120.0 (6)
O8—C7—C1125.3 (6)O32—C30—C24125.8 (7)
O9—C7—C1113.4 (6)O31—C30—C24114.2 (6)
C7—O9—H9109.5C30—O31—H31109.5
C2—N10—S11125.8 (4)C25—N33—S34124.4 (4)
C2—N10—H10117.1C25—N33—H33117.8
S11—N10—H10117.1S34—N33—H33117.8
O13—S11—O12117.5 (3)O35—S34—O36119.3 (3)
O13—S11—N10112.5 (3)O35—S34—N33109.3 (3)
O12—S11—N10103.2 (3)O36—S34—N33103.7 (3)
O13—S11—C14107.3 (3)O35—S34—C37107.7 (3)
O12—S11—C14109.7 (3)O36—S34—C37109.1 (3)
N10—S11—C14106.0 (3)N33—S34—C37107.1 (3)
C19—C14—C15119.9 (6)C38—C37—C42119.3 (6)
C19—C14—S11119.9 (5)C38—C37—S34119.4 (6)
C15—C14—S11119.9 (5)C42—C37—S34121.2 (5)
C16—C15—C14119.0 (6)C37—C38—C39122.1 (6)
C16—C15—H15120.5C37—C38—H38118.9
C14—C15—H15120.5C39—C38—H38118.9
C15—C16—C17121.7 (6)C38—C39—C40117.8 (6)
C15—C16—H16119.2C38—C39—H39121.1
C17—C16—H16119.2C40—C39—H39121.1
C18—C17—C16119.2 (6)C39—C40—C41120.6 (7)
C18—C17—N20124.7 (5)C39—C40—N43122.2 (6)
C16—C17—N20116.1 (5)C41—C40—N43117.2 (6)
C17—C18—C19120.5 (6)C42—C41—C40119.3 (6)
C17—C18—H18119.7C42—C41—H41120.3
C19—C18—H18119.7C40—C41—H41120.3
C14—C19—C18119.7 (6)C41—C42—C37120.8 (6)
C14—C19—H19120.1C41—C42—H42119.6
C18—C19—H19120.1C37—C42—H42119.6
C21—N20—C17130.0 (5)C44—N43—C40128.8 (6)
C21—N20—H20115C44—N43—H43115.6
C17—N20—H20115C40—N43—H43115.6
O22—C21—N20121.9 (6)O45—C44—N43121.7 (7)
O22—C21—C23121.6 (6)O45—C44—C46122.7 (7)
N20—C21—C23116.5 (6)N43—C44—C46115.5 (6)
C21—C23—H23A109.5C44—C46—H46A109.5
C21—C23—H23B109.5C44—C46—H46B109.5
H23A—C23—H23B109.5H46A—C46—H46B109.5
C21—C23—H23C109.5C44—C46—H46C109.5
H23A—C23—H23C109.5H46A—C46—H46C109.5
H23B—C23—H23C109.5H46B—C46—H46C109.5
D—H···AD—HH···AD···AD—H···A
O9—H9···O22i0.821.842.649 (6)168
N10—H10···O80.862.132.624 (7)116
N20—H20···O13ii0.862.243.073 (6)164
O31—H31···O45iii0.821.812.623 (6)174
N33—H33···O320.862.172.641 (7)114
N43—H43···O36i0.862.112.958 (7)168
C23—H23B···Cg10.962.743.6110 (15)151
C46—H46C···Cg20.962.713.5821 (13)151
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C37–C42 and C14–C19 rings, respectively.

D—H⋯AD—HH⋯ADAD—H⋯A
O9—H9⋯O22i0.821.842.649 (6)168
N10—H10⋯O80.862.132.624 (7)116
N20—H20⋯O13ii0.862.243.073 (6)164
O31—H31⋯O45iii0.821.812.623 (6)174
N33—H33⋯O320.862.172.641 (7)114
N43—H43⋯O36i0.862.112.958 (7)168
C23—H23BCg10.962.743.6110 (15)151
C46—H46CCg20.962.713.5821 (13)151

Symmetry codes: (i) ; (ii) ; (iii) .

  3 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.  2-(4-Acetamido-benzene-sulfonamido)-3-methyl-butanoic acid.

Authors:  Shahzad Sharif; Haffsah Iqbal; Islam Ullah Khan; Peter John; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-05-08

3.  2,5-Dichloro-N-(4-meth-oxy-phen-yl)benzensulfonamide.

Authors:  Islam Ullah Khan; Sajida Bibi; Irfana Mariam; Shahzad Sharif; Sung Kwon Kang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-01-12
  3 in total
  1 in total

1.  4-Chloro-N-cyclo-hexyl-benzene-sulfonamide.

Authors:  Shahzad Sharif; Shumaila Younas Mughal; Islam Ullah Khan; Mehmet Akkurt; Muneeb Hayat Khan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-01-21
  1 in total

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