Literature DB >> 22064806

N,N'-(Ethane-1,2-di-yl)dibenzene-sulfonamide.

Mohammad T M Al-Dajani, Jamal Talaat, Nornisah Mohamed, Madhukar Hemamalini, Hoong-Kun Fun.   

Abstract

In the title compound, C(14)H(16)N(2)O(4)S(2), the dihedral angle between the terminal phenyl rings is 77.07 (13)°. The geometries around the S atoms are distorted tetra-hedral, with O-S-O angles of 120.66 (12) and 119.44 (11)°. In the crystal, mol-ecules are stacked in columns along the a axis via inter-molecular N-H⋯O and C-H⋯O hydrogen bonds.

Entities:  

Year:  2011        PMID： 22064806      PMCID： PMC3200692          DOI： 10.1107/S1600536811030157

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


Related literature

For biological activities and applications of sulfonamide derivatives, see: Misra et al. (1982 ▶); Maren (1976 ▶); Li et al. (1995 ▶); Yoshino et al. (1992 ▶). For related structures, see: Basak et al. (1982 ▶); Cotton & Stokley (1970 ▶).

Experimental

Crystal data

C14H16N2O4S2 M = 340.41 Monoclinic, a = 5.2115 (4) Å b = 16.6905 (13) Å c = 17.8750 (14) Å β = 93.187 (2)° V = 1552.4 (2) Å3 Z = 4 Mo Kα radiation μ = 0.36 mm−1 T = 296 K 0.46 × 0.08 × 0.07 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.852, T max = 0.975 14604 measured reflections 3545 independent reflections 2628 reflections with I > 2σ(I) R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.119 S = 1.04 3545 reflections 207 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.28 e Å−3 Δρmin = −0.33 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030157/is2755sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030157/is2755Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811030157/is2755Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C14H16N2O4S2F(000) = 712
Mr = 340.41Dx = 1.456 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3372 reflections
a = 5.2115 (4) Åθ = 2.4–32.2°
b = 16.6905 (13) ŵ = 0.36 mm−1
c = 17.8750 (14) ÅT = 296 K
β = 93.187 (2)°Needle, colourless
V = 1552.4 (2) Å30.46 × 0.08 × 0.07 mm
Z = 4
Bruker APEXII DUO CCD area-detector diffractometer3545 independent reflections
Radiation source: fine-focus sealed tube2628 reflections with I > 2σ(I)
graphiteRint = 0.047
φ and ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −6→6
Tmin = 0.852, Tmax = 0.975k = −21→21
14604 measured reflectionsl = −23→23
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.062P)2 + 0.174P] where P = (Fo2 + 2Fc2)/3
3545 reflections(Δ/σ)max = 0.001
207 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.33 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
S10.29124 (10)0.88198 (3)0.48674 (3)0.03665 (17)
S20.52329 (10)0.99919 (3)0.80016 (3)0.03343 (16)
O10.2344 (4)0.92155 (10)0.41688 (9)0.0546 (5)
O20.5474 (3)0.88119 (11)0.51993 (11)0.0563 (5)
O30.7660 (3)0.98466 (10)0.76908 (10)0.0484 (4)
O40.4855 (4)0.97572 (10)0.87531 (9)0.0514 (5)
N10.1146 (4)0.92431 (11)0.54596 (11)0.0349 (4)
N20.3085 (4)0.95274 (10)0.74743 (10)0.0330 (4)
C1−0.0240 (5)0.76368 (15)0.43026 (14)0.0502 (6)
H1A−0.11240.80430.40420.060*
C2−0.1056 (6)0.68534 (16)0.42342 (16)0.0595 (7)
H2A−0.25050.67310.39290.071*
C30.0258 (6)0.62555 (15)0.46139 (17)0.0606 (8)
H3A−0.02960.57280.45600.073*
C40.2370 (7)0.64248 (16)0.50704 (16)0.0643 (8)
H4A0.32440.60150.53280.077*
C50.3216 (5)0.72138 (15)0.51494 (14)0.0518 (6)
H5A0.46540.73340.54610.062*
C60.1905 (4)0.78130 (13)0.47623 (11)0.0353 (5)
C70.1430 (4)0.90629 (12)0.62583 (12)0.0368 (5)
H7A0.23380.85590.63320.044*
H7B−0.02550.90060.64570.044*
C80.2890 (5)0.97194 (13)0.66725 (11)0.0370 (5)
H8A0.45960.97680.64860.044*
H8B0.20061.02260.65930.044*
C90.4584 (4)1.10252 (12)0.79155 (11)0.0325 (5)
C100.5938 (5)1.14968 (14)0.74477 (13)0.0451 (6)
H10A0.72531.12790.71810.054*
C110.5318 (6)1.23066 (15)0.73773 (15)0.0557 (7)
H11A0.62141.26320.70590.067*
C120.3395 (6)1.26242 (15)0.77743 (16)0.0566 (7)
H12A0.30011.31660.77300.068*
C130.2043 (6)1.21465 (16)0.82375 (17)0.0592 (7)
H13A0.07211.23660.85000.071*
C140.2625 (5)1.13442 (14)0.83181 (14)0.0456 (6)
H14A0.17201.10220.86370.055*
H1N1−0.017 (5)0.9291 (15)0.5307 (14)0.034 (7)*
H1N20.168 (5)0.9581 (14)0.7659 (13)0.036 (6)*
U11U22U33U12U13U23
S10.0300 (3)0.0369 (3)0.0434 (3)−0.0052 (2)0.0060 (2)−0.0049 (2)
S20.0273 (3)0.0334 (3)0.0391 (3)0.0054 (2)−0.0026 (2)−0.0020 (2)
O10.0715 (13)0.0515 (10)0.0419 (9)−0.0085 (9)0.0125 (9)0.0041 (7)
O20.0266 (9)0.0588 (11)0.0835 (12)−0.0066 (8)0.0036 (9)−0.0167 (9)
O30.0240 (8)0.0516 (10)0.0694 (11)0.0088 (7)−0.0001 (8)−0.0077 (8)
O40.0628 (12)0.0508 (9)0.0397 (9)0.0058 (9)−0.0064 (8)0.0064 (7)
N10.0268 (10)0.0378 (10)0.0397 (10)0.0006 (8)−0.0024 (9)−0.0045 (8)
N20.0276 (10)0.0339 (9)0.0378 (9)−0.0010 (8)0.0057 (8)−0.0022 (7)
C10.0468 (15)0.0431 (13)0.0595 (15)−0.0009 (12)−0.0085 (13)−0.0065 (11)
C20.0548 (17)0.0508 (15)0.0714 (18)−0.0129 (13)−0.0094 (15)−0.0140 (13)
C30.075 (2)0.0389 (13)0.0684 (17)−0.0122 (14)0.0061 (16)−0.0111 (12)
C40.086 (2)0.0411 (13)0.0645 (17)0.0081 (15)−0.0052 (17)0.0018 (12)
C50.0519 (16)0.0467 (13)0.0550 (14)0.0048 (12)−0.0123 (13)−0.0053 (11)
C60.0315 (12)0.0365 (11)0.0383 (11)0.0003 (9)0.0052 (10)−0.0064 (9)
C70.0366 (12)0.0330 (10)0.0408 (11)−0.0065 (9)0.0033 (10)−0.0018 (9)
C80.0388 (12)0.0333 (10)0.0385 (11)−0.0073 (10)−0.0012 (10)0.0005 (9)
C90.0285 (11)0.0341 (10)0.0340 (10)0.0012 (9)−0.0059 (9)−0.0059 (8)
C100.0467 (14)0.0427 (12)0.0462 (13)0.0003 (11)0.0056 (11)−0.0038 (10)
C110.0676 (19)0.0419 (13)0.0573 (15)−0.0067 (13)0.0012 (14)0.0049 (11)
C120.0651 (19)0.0312 (12)0.0719 (17)0.0059 (12)−0.0101 (15)−0.0042 (11)
C130.0524 (16)0.0446 (14)0.0805 (19)0.0124 (13)0.0043 (15)−0.0164 (13)
C140.0392 (13)0.0401 (12)0.0581 (14)0.0039 (10)0.0093 (12)−0.0083 (10)
S1—O11.4291 (17)C4—H4A0.9300
S1—O21.4307 (19)C5—C61.376 (3)
S1—N11.605 (2)C5—H5A0.9300
S1—C61.767 (2)C7—C81.505 (3)
S2—O41.4233 (17)C7—H7A0.9700
S2—O31.4300 (17)C7—H7B0.9700
S2—N21.6202 (19)C8—H8A0.9700
S2—C91.763 (2)C8—H8B0.9700
N1—C71.459 (3)C9—C101.372 (3)
N1—H1N10.73 (3)C9—C141.387 (3)
N2—C81.467 (3)C10—C111.394 (3)
N2—H1N20.82 (3)C10—H10A0.9300
C1—C21.378 (3)C11—C121.367 (4)
C1—C61.382 (3)C11—H11A0.9300
C1—H1A0.9300C12—C131.372 (4)
C2—C31.369 (4)C12—H12A0.9300
C2—H2A0.9300C13—C141.379 (3)
C3—C41.363 (4)C13—H13A0.9300
C3—H3A0.9300C14—H14A0.9300
C4—C51.393 (4)
O1—S1—O2120.66 (12)C5—C6—C1120.5 (2)
O1—S1—N1105.92 (11)C5—C6—S1120.09 (19)
O2—S1—N1106.67 (11)C1—C6—S1119.43 (18)
O1—S1—C6107.49 (10)N1—C7—C8110.63 (17)
O2—S1—C6107.46 (11)N1—C7—H7A109.5
N1—S1—C6108.11 (10)C8—C7—H7A109.5
O4—S2—O3119.44 (11)N1—C7—H7B109.5
O4—S2—N2106.86 (11)C8—C7—H7B109.5
O3—S2—N2106.87 (10)H7A—C7—H7B108.1
O4—S2—C9108.40 (10)N2—C8—C7109.10 (17)
O3—S2—C9107.56 (10)N2—C8—H8A109.9
N2—S2—C9107.12 (10)C7—C8—H8A109.9
C7—N1—S1121.62 (17)N2—C8—H8B109.9
C7—N1—H1N1115.6 (19)C7—C8—H8B109.9
S1—N1—H1N1111 (2)H8A—C8—H8B108.3
C8—N2—S2118.16 (14)C10—C9—C14120.9 (2)
C8—N2—H1N2110.7 (16)C10—C9—S2120.78 (17)
S2—N2—H1N2108.3 (16)C14—C9—S2118.26 (17)
C2—C1—C6119.4 (2)C9—C10—C11119.1 (2)
C2—C1—H1A120.3C9—C10—H10A120.4
C6—C1—H1A120.3C11—C10—H10A120.4
C3—C2—C1120.3 (3)C12—C11—C10120.2 (2)
C3—C2—H2A119.9C12—C11—H11A119.9
C1—C2—H2A119.9C10—C11—H11A119.9
C4—C3—C2120.7 (2)C11—C12—C13120.3 (2)
C4—C3—H3A119.6C11—C12—H12A119.9
C2—C3—H3A119.6C13—C12—H12A119.9
C3—C4—C5119.8 (3)C12—C13—C14120.7 (2)
C3—C4—H4A120.1C12—C13—H13A119.7
C5—C4—H4A120.1C14—C13—H13A119.7
C6—C5—C4119.4 (3)C13—C14—C9118.8 (2)
C6—C5—H5A120.3C13—C14—H14A120.6
C4—C5—H5A120.3C9—C14—H14A120.6
O1—S1—N1—C7−172.40 (17)N1—S1—C6—C180.2 (2)
O2—S1—N1—C7−42.7 (2)S1—N1—C7—C8102.1 (2)
C6—S1—N1—C772.6 (2)S2—N2—C8—C7162.43 (15)
O4—S2—N2—C8174.49 (16)N1—C7—C8—N2178.68 (19)
O3—S2—N2—C8−56.57 (19)O4—S2—C9—C10145.79 (19)
C9—S2—N2—C858.48 (18)O3—S2—C9—C1015.4 (2)
C6—C1—C2—C3−0.5 (4)N2—S2—C9—C10−99.2 (2)
C1—C2—C3—C40.7 (5)O4—S2—C9—C14−35.8 (2)
C2—C3—C4—C5−0.4 (5)O3—S2—C9—C14−166.27 (18)
C3—C4—C5—C6−0.2 (4)N2—S2—C9—C1479.1 (2)
C4—C5—C6—C10.4 (4)C14—C9—C10—C11−0.2 (4)
C4—C5—C6—S1178.9 (2)S2—C9—C10—C11178.08 (19)
C2—C1—C6—C5−0.1 (4)C9—C10—C11—C120.4 (4)
C2—C1—C6—S1−178.6 (2)C10—C11—C12—C13−0.8 (4)
O1—S1—C6—C5147.7 (2)C11—C12—C13—C140.9 (4)
O2—S1—C6—C516.4 (2)C12—C13—C14—C9−0.7 (4)
N1—S1—C6—C5−98.4 (2)C10—C9—C14—C130.4 (4)
O1—S1—C6—C1−33.8 (2)S2—C9—C14—C13−178.0 (2)
O2—S1—C6—C1−165.05 (19)
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O2i0.73 (3)2.40 (3)3.053 (3)149 (3)
N2—H1N2···O3i0.83 (3)2.15 (3)2.924 (3)157 (2)
C10—H10A···O1ii0.932.573.294 (3)135.
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1N1⋯O2i0.73 (3)2.40 (3)3.053 (3)149 (3)
N2—H1N2⋯O3i0.83 (3)2.15 (3)2.924 (3)157 (2)
C10—H10A⋯O1ii0.932.573.294 (3)135

Symmetry codes: (i) ; (ii) .

  5 in total

1.  Novel sulfonamides as potential, systemically active antitumor agents.

Authors:  H Yoshino; N Ueda; J Niijima; H Sugumi; Y Kotake; N Koyanagi; K Yoshimatsu; M Asada; T Watanabe; T Nagasu
Journal:  J Med Chem       Date:  1992-06-26       Impact factor: 7.446

2.  A short history of SHELX.

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

Review 3.  Relatons between structure and biological activity of sulfonamides.

Authors:  T H Maren
Journal:  Annu Rev Pharmacol Toxicol       Date:  1976       Impact factor: 13.820

4.  1,2-Diarylcyclopentenes as selective cyclooxygenase-2 inhibitors and orally active anti-inflammatory agents.

Authors:  J J Li; G D Anderson; E G Burton; J N Cogburn; J T Collins; D J Garland; S A Gregory; H C Huang; P C Isakson; C M Koboldt
Journal:  J Med Chem       Date:  1995-10-27       Impact factor: 7.446

5.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  5 in total
  1 in total

1.  N,N'-(Ethane-1,2-di-yl)bis-(methane-sulfon-amide).

Authors:  Wesley Ting Kwok Chan; Ka Yan Karen Kung; Man-Kin Wong
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-01-15
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.