Literature DB >> 21583981

N-Acetyl-4-(benzene-sulfonamido)benzene-sulfonamide.

Muhammad Ashfaq, M Nawaz Tahir, Islam Ullah Khan, Muhammad Nadeem Arshad, Syed Saeed-Ul-Hassan.   

Abstract

In the mol-ecule of the title compound, C(14)H(14)N(2)O(5)S(2), the dihedral angle between the aromatic rings is 77.75 (9)°. The acetamide group is planar [maximum deviation = 0.002 (3) Å] and oriented at dihedral angles of 13.49 (21) and 73.94 (10)° with respect to the aromatic rings. An intra-molecular C-H⋯O inter-action results in the formation of a six-membered ring. In the crystal structure, inter-molecular N-H⋯O and C-H⋯O inter-actions link the mol-ecules into a three-dimensional network, forming R(2) (2)(20) ring motifs.

Entities:  

Year:  2009        PMID： 21583981      PMCID： PMC2977844          DOI： 10.1107/S1600536809015876

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


Related literature

For related structures, see: Chohan et al. (2008 ▶, 2009 ▶); Deng & Mani (2006 ▶); Ellingboe et al. (1992 ▶); Shad et al. (2009 ▶); Tahir et al. (2008 ▶). For ring-motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H14N2O5S2 M = 354.39 Monoclinic, a = 9.9316 (9) Å b = 9.4828 (8) Å c = 17.6490 (17) Å β = 103.169 (5)° V = 1618.5 (3) Å3 Z = 4 Mo Kα radiation μ = 0.36 mm−1 T = 296 K 0.28 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.909, T max = 0.940 17674 measured reflections 4034 independent reflections 2423 reflections with I > 2σ(I) R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.049 wR(F 2) = 0.128 S = 1.02 4034 reflections 209 parameters H-atom parameters constrained Δρmax = 0.31 e Å−3 Δρmin = −0.36 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015876/hk2676sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015876/hk2676Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C14H14N2O5S2F(000) = 736
Mr = 354.39Dx = 1.454 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4034 reflections
a = 9.9316 (9) Åθ = 2.4–28.3°
b = 9.4828 (8) ŵ = 0.36 mm−1
c = 17.6490 (17) ÅT = 296 K
β = 103.169 (5)°Prism, colorless
V = 1618.5 (3) Å30.28 × 0.22 × 0.18 mm
Z = 4
Bruker Kappa APEXII CCD area-detector diffractometer4034 independent reflections
Radiation source: fine-focus sealed tube2423 reflections with I > 2σ(I)
graphiteRint = 0.060
Detector resolution: 7.40 pixels mm-1θmax = 28.3°, θmin = 2.4°
ω scansh = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −11→12
Tmin = 0.909, Tmax = 0.940l = −22→23
17674 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.052P)2 + 0.3831P] where P = (Fo2 + 2Fc2)/3
4034 reflections(Δ/σ)max < 0.001
209 parametersΔρmax = 0.31 e Å−3
0 restraintsΔρmin = −0.36 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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.
xyzUiso*/Ueq
S10.90183 (7)0.28463 (8)−0.04571 (4)0.0407 (3)
S20.58491 (7)0.45284 (7)0.26062 (4)0.0374 (2)
O10.9231 (2)0.3308 (2)−0.11946 (11)0.0530 (7)
O21.01569 (19)0.2335 (2)0.01166 (11)0.0546 (7)
O30.68083 (19)0.4029 (2)0.32790 (10)0.0564 (7)
O40.5257 (2)0.58953 (19)0.26098 (11)0.0510 (7)
O50.3371 (2)0.4255 (2)0.13539 (11)0.0560 (7)
N10.8361 (2)0.4215 (2)−0.01260 (12)0.0384 (7)
N20.4595 (2)0.3347 (2)0.24701 (12)0.0387 (7)
C10.7705 (3)0.1563 (3)−0.06104 (15)0.0396 (9)
C20.6519 (3)0.1794 (3)−0.11844 (17)0.0518 (11)
C30.5482 (3)0.0815 (4)−0.1295 (2)0.0703 (14)
C40.5621 (4)−0.0385 (4)−0.0833 (3)0.0759 (17)
C50.6797 (4)−0.0586 (3)−0.0265 (2)0.0729 (16)
C60.7849 (3)0.0381 (3)−0.01472 (18)0.0545 (11)
C70.7799 (2)0.4241 (3)0.05379 (14)0.0315 (8)
C80.8129 (3)0.3261 (3)0.11352 (15)0.0417 (9)
C90.7502 (3)0.3347 (3)0.17563 (14)0.0389 (9)
C100.6584 (3)0.4411 (3)0.17997 (14)0.0321 (8)
C110.6272 (3)0.5403 (3)0.12140 (17)0.0472 (10)
C120.6873 (3)0.5305 (3)0.05858 (16)0.0446 (10)
C130.3439 (3)0.3407 (3)0.18721 (15)0.0393 (9)
C140.2314 (3)0.2385 (4)0.19149 (18)0.0655 (13)
H1N0.835460.49926−0.037740.0461*
H20.642890.26019−0.149020.0622*
H2N0.467140.265480.279200.0464*
H30.468130.09538−0.167980.0843*
H40.49166−0.10523−0.090980.0910*
H50.68825−0.138770.004600.0874*
H60.864710.024090.023930.0655*
H80.876840.255220.111760.0501*
H90.770380.267630.215030.0467*
H110.566020.613310.124320.0566*
H120.665220.596580.018740.0536*
H14A0.192940.201410.140560.0984*
H14B0.160380.285760.210670.0984*
H14C0.268680.162770.226010.0984*
U11U22U33U12U13U23
S10.0359 (4)0.0556 (5)0.0317 (4)0.0099 (3)0.0102 (3)−0.0074 (3)
S20.0349 (4)0.0507 (4)0.0281 (3)−0.0047 (3)0.0104 (3)−0.0067 (3)
O10.0571 (13)0.0707 (14)0.0371 (11)0.0023 (11)0.0232 (10)−0.0102 (10)
O20.0387 (11)0.0718 (14)0.0482 (12)0.0218 (10)−0.0006 (10)−0.0091 (10)
O30.0407 (11)0.0984 (16)0.0271 (10)−0.0047 (11)0.0013 (9)−0.0017 (10)
O40.0557 (12)0.0467 (11)0.0586 (13)−0.0019 (10)0.0294 (10)−0.0167 (10)
O50.0474 (12)0.0781 (15)0.0391 (11)−0.0021 (11)0.0025 (10)0.0205 (11)
N10.0451 (13)0.0396 (12)0.0341 (12)0.0070 (10)0.0163 (10)0.0013 (10)
N20.0379 (12)0.0473 (13)0.0291 (12)−0.0050 (10)0.0042 (10)0.0113 (10)
C10.0409 (15)0.0424 (15)0.0356 (15)0.0128 (13)0.0089 (12)−0.0048 (12)
C20.0467 (18)0.0586 (19)0.0480 (18)0.0087 (15)0.0062 (15)0.0005 (15)
C30.046 (2)0.085 (3)0.074 (2)0.000 (2)0.0015 (18)−0.008 (2)
C40.072 (3)0.066 (3)0.095 (3)−0.016 (2)0.030 (2)−0.021 (2)
C50.093 (3)0.046 (2)0.082 (3)0.002 (2)0.025 (2)0.0040 (18)
C60.063 (2)0.0479 (18)0.0515 (19)0.0132 (16)0.0109 (16)−0.0028 (15)
C70.0290 (13)0.0378 (14)0.0279 (13)−0.0014 (11)0.0067 (10)−0.0040 (11)
C80.0456 (16)0.0467 (16)0.0347 (15)0.0180 (13)0.0130 (13)0.0028 (12)
C90.0460 (16)0.0421 (15)0.0291 (14)0.0109 (13)0.0095 (12)0.0051 (12)
C100.0313 (13)0.0358 (14)0.0306 (13)0.0013 (11)0.0098 (11)−0.0013 (11)
C110.0574 (18)0.0407 (16)0.0517 (18)0.0180 (14)0.0298 (15)0.0084 (13)
C120.0578 (18)0.0403 (16)0.0420 (16)0.0159 (14)0.0242 (14)0.0124 (12)
C130.0376 (15)0.0549 (17)0.0272 (14)−0.0049 (13)0.0109 (12)0.0006 (12)
C140.0526 (19)0.100 (3)0.0427 (18)−0.0311 (19)0.0083 (15)0.0000 (17)
S1—O11.434 (2)C7—C121.381 (4)
S1—O21.420 (2)C7—C81.387 (4)
S1—N11.621 (2)C8—C91.381 (4)
S1—C11.759 (3)C9—C101.374 (4)
S2—O31.4235 (19)C10—C111.380 (4)
S2—O41.424 (2)C11—C121.377 (4)
S2—N21.652 (2)C13—C141.494 (5)
S2—C101.745 (3)C2—H20.9300
O5—C131.208 (3)C3—H30.9300
N1—C71.408 (3)C4—H40.9300
N2—C131.372 (3)C5—H50.9300
N1—H1N0.8600C6—H60.9300
N2—H2N0.8600C8—H80.9300
C1—C61.375 (4)C9—H90.9300
C1—C21.385 (4)C11—H110.9300
C2—C31.367 (5)C12—H120.9300
C3—C41.388 (6)C14—H14A0.9600
C4—C51.368 (6)C14—H14B0.9600
C5—C61.370 (5)C14—H14C0.9600
S1···H82.8600C8···C63.517 (4)
O1···N2i2.922 (3)C9···O4xi3.237 (3)
O2···C6ii3.242 (4)C10···O53.111 (4)
O2···C5ii3.407 (4)C11···O53.142 (4)
O2···C83.116 (3)C12···O5vi3.402 (3)
O2···C14iii3.401 (4)C14···O4xii3.193 (4)
O4···O52.992 (3)C14···O2xiii3.401 (4)
O4···C8iv3.300 (3)C2···H14Bi3.0500
O4···C9iv3.237 (3)C2···H11vi2.9100
O4···C14v3.193 (4)C5···H14Ax2.9400
O5···C113.142 (4)C6···H83.0200
O5···N1vi2.839 (3)H1N···H122.3400
O5···O42.992 (3)H1N···O2vii2.9200
O5···C12vi3.402 (3)H1N···O5vi2.2500
O5···C103.111 (4)H2···O12.7900
O1···H14Ci2.8100H2···O4vi2.6900
O1···H22.7900H2···H11vi2.5200
O1···H2Ni2.1400H2···H14Bi2.5600
O2···H82.4900H2N···H14C2.2100
O2···H6ii2.8500H2N···O1ix2.1400
O2···H62.5300H3···O3xiv2.8400
O2···H1Nvii2.9200H5···H12xv2.5400
O2···H14Aiii2.5600H6···O22.5300
O3···H3viii2.8400H6···O2ii2.8500
O3···H92.6900H8···S12.8600
O4···H112.5400H8···O22.4900
O4···H14Bv2.7500H8···C63.0200
O4···H2vi2.6900H8···O4xi2.7300
O4···H8iv2.7300H9···O32.6900
O4···H9iv2.6000H9···O4xi2.6000
O5···H1Nvi2.2500H11···O42.5400
O5···H12vi2.7200H11···C2vi2.9100
N1···O5vi2.839 (3)H11···H2vi2.5200
N2···O1ix2.922 (3)H12···H1N2.3400
C1···C83.416 (4)H12···H5xvi2.5400
C4···C5x3.534 (6)H12···O5vi2.7200
C4···C4x3.515 (7)H14A···O2xiii2.5600
C5···O2ii3.407 (4)H14A···C5x2.9400
C5···C4x3.534 (6)H14B···O4xii2.7500
C6···C83.517 (4)H14B···C2ix3.0500
C6···O2ii3.242 (4)H14B···H2ix2.5600
C8···O23.116 (3)H14C···H2N2.2100
C8···C13.416 (4)H14C···O1ix2.8100
C8···O4xi3.300 (3)
O1—S1—O2119.56 (12)S2—C10—C11120.2 (2)
O1—S1—N1103.74 (11)C9—C10—C11119.9 (3)
O1—S1—C1109.21 (12)C10—C11—C12119.5 (3)
O2—S1—N1109.70 (11)C7—C12—C11121.0 (3)
O2—S1—C1108.39 (13)O5—C13—C14123.8 (3)
N1—S1—C1105.31 (12)N2—C13—C14116.0 (2)
O3—S2—O4119.85 (12)O5—C13—N2120.2 (3)
O3—S2—N2103.58 (11)C1—C2—H2121.00
O3—S2—C10109.54 (13)C3—C2—H2120.00
O4—S2—N2108.64 (11)C2—C3—H3120.00
O4—S2—C10108.16 (13)C4—C3—H3120.00
N2—S2—C10106.25 (12)C3—C4—H4120.00
S1—N1—C7125.64 (18)C5—C4—H4120.00
S2—N2—C13123.70 (18)C4—C5—H5120.00
C7—N1—H1N117.00C6—C5—H5120.00
S1—N1—H1N117.00C1—C6—H6121.00
S2—N2—H2N118.00C5—C6—H6121.00
C13—N2—H2N118.00C7—C8—H8120.00
S1—C1—C2118.7 (2)C9—C8—H8120.00
S1—C1—C6120.0 (2)C8—C9—H9120.00
C2—C1—C6121.3 (3)C10—C9—H9120.00
C1—C2—C3119.0 (3)C10—C11—H11120.00
C2—C3—C4120.1 (3)C12—C11—H11120.00
C3—C4—C5119.9 (3)C7—C12—H12119.00
C4—C5—C6120.8 (3)C11—C12—H12120.00
C1—C6—C5118.9 (3)C13—C14—H14A109.00
C8—C7—C12119.2 (2)C13—C14—H14B109.00
N1—C7—C8123.4 (2)C13—C14—H14C109.00
N1—C7—C12117.4 (2)H14A—C14—H14B109.00
C7—C8—C9119.5 (3)H14A—C14—H14C110.00
C8—C9—C10120.8 (2)H14B—C14—H14C109.00
S2—C10—C9119.9 (2)
O1—S1—N1—C7171.1 (2)S2—N2—C13—O59.3 (4)
O2—S1—N1—C7−60.1 (2)S2—N2—C13—C14−170.4 (2)
C1—S1—N1—C756.4 (2)S1—C1—C2—C3−178.6 (2)
O1—S1—C1—C2−44.2 (3)C6—C1—C2—C3−0.8 (4)
O1—S1—C1—C6137.9 (2)S1—C1—C6—C5178.4 (2)
O2—S1—C1—C2−176.0 (2)C2—C1—C6—C50.5 (5)
O2—S1—C1—C66.1 (3)C1—C2—C3—C40.4 (5)
N1—S1—C1—C266.7 (3)C2—C3—C4—C50.1 (6)
N1—S1—C1—C6−111.2 (2)C3—C4—C5—C6−0.4 (6)
O3—S2—N2—C13−179.6 (2)C4—C5—C6—C10.0 (5)
O4—S2—N2—C1352.0 (2)N1—C7—C8—C9−178.4 (2)
C10—S2—N2—C13−64.2 (2)C12—C7—C8—C91.5 (4)
O3—S2—C10—C932.2 (3)N1—C7—C12—C11179.7 (3)
O3—S2—C10—C11−146.2 (2)C8—C7—C12—C11−0.2 (4)
O4—S2—C10—C9164.5 (2)C7—C8—C9—C10−1.7 (4)
O4—S2—C10—C11−14.0 (3)C8—C9—C10—S2−177.9 (2)
N2—S2—C10—C9−79.1 (3)C8—C9—C10—C110.5 (4)
N2—S2—C10—C11102.5 (2)S2—C10—C11—C12179.2 (2)
S1—N1—C7—C822.2 (3)C9—C10—C11—C120.8 (4)
S1—N1—C7—C12−157.8 (2)C10—C11—C12—C7−1.0 (4)
D—H···AD—HH···AD···AD—H···A
N1—H1N···O5vi0.862.252.839 (3)126
N2—H2N···O1ix0.862.142.922 (3)151
C8—H8···O20.932.493.116 (3)125
C9—H9···O4xi0.932.603.237 (3)126
C14—H14A···O2xiii0.962.563.401 (4)147
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1N⋯O5i0.862.252.839 (3)126
N2—H2N⋯O1ii0.862.142.922 (3)151
C8—H8⋯O20.932.493.116 (3)125
C9—H9⋯O4iii0.932.603.237 (3)126
C14—H14A⋯O2iv0.962.563.401 (4)147

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

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