Literature DB >> 22199786

N,N'-Diallyl-2,2',5,5'-tetra-chloro-N,N'-[1,3-phenyl-enebis(methyl-ene)]dibenzene-sulfonamide.

Tahir Ali Sheikh, Islam Ullah Khan, William T A Harrison.   

Abstract

In the title compound, C(26)H(24)Cl(4)N(2)O(4)S(2), the dihedral angles between the central benzene ring and the pendant rings are 70.07 (12) and 59.07 (12)°. The equivalent angle between the pendant rings is 79.24 (12)°. Both sulfonamide groups lie to the same side of the central ring but the pendant chains have very different conformations, as indicated by their C-S-N-C torsion angles [104.66 (17) and -76.35 (19)°] and S-N-C-C torsion angles [129.61 (17) and 147.10 (17)°]. Both N atoms are close to planar (bond angle sums = 359.0 and 354.8°). In the crystal, inversion dimers are formed via a pair of weak C-H⋯O inter-actions which generate R(2) (2)(22) loops.

Entities:  

Year:  2011        PMID: 22199786      PMCID: PMC3238937          DOI: 10.1107/S1600536811045478

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


Related literature

For related structures, see: Ejaz et al. (2011a ▶,b ▶).

Experimental

Crystal data

C26H24Cl4N2O4S2 M = 634.39 Triclinic, a = 8.2744 (2) Å b = 11.3398 (2) Å c = 15.6481 (4) Å α = 87.777 (1)° β = 84.443 (1)° γ = 84.257 (1)° V = 1453.40 (6) Å3 Z = 2 Mo Kα radiation μ = 0.59 mm−1 T = 296 K 0.40 × 0.15 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer 21435 measured reflections 7190 independent reflections 5200 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.122 S = 1.05 7190 reflections 343 parameters H-atom parameters constrained Δρmax = 0.65 e Å−3 Δρmin = −0.59 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811045478/su2341sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045478/su2341Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811045478/su2341Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C26H24Cl4N2O4S2Z = 2
Mr = 634.39F(000) = 652
Triclinic, P1Dx = 1.450 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2744 (2) ÅCell parameters from 7190 reflections
b = 11.3398 (2) Åθ = 2.2–26.4°
c = 15.6481 (4) ŵ = 0.59 mm1
α = 87.777 (1)°T = 296 K
β = 84.443 (1)°Block, colourless
γ = 84.257 (1)°0.40 × 0.15 × 0.15 mm
V = 1453.40 (6) Å3
Bruker APEXII CCD diffractometer5200 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
graphiteθmax = 28.4°, θmin = 2.9°
ω scansh = −11→11
21435 measured reflectionsk = −15→15
7190 independent reflectionsl = −20→20
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0515P)2 + 0.5046P] where P = (Fo2 + 2Fc2)/3
7190 reflections(Δ/σ)max < 0.001
343 parametersΔρmax = 0.65 e Å3
0 restraintsΔρmin = −0.59 e Å3
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.
xyzUiso*/Ueq
C10.3523 (3)0.37348 (17)0.05525 (13)0.0427 (5)
H10.46340.38010.05530.051*
C20.2551 (3)0.36986 (17)0.13297 (13)0.0436 (5)
C30.0903 (3)0.3619 (2)0.13202 (16)0.0567 (6)
H30.02380.36080.18340.068*
C40.0236 (3)0.3556 (3)0.05513 (19)0.0681 (7)
H4−0.08780.35000.05490.082*
C50.1202 (3)0.3573 (2)−0.02092 (17)0.0630 (7)
H50.07420.3518−0.07240.076*
C60.2857 (3)0.36727 (18)−0.02203 (13)0.0475 (5)
C70.3328 (3)0.36645 (18)0.21600 (13)0.0452 (5)
H7A0.39170.43580.21880.054*
H7B0.24920.36730.26400.054*
C80.3762 (3)0.14402 (19)0.22185 (16)0.0560 (6)
H8A0.46360.08010.21930.067*
H8B0.31800.14080.17120.067*
C90.2634 (4)0.1266 (2)0.2993 (2)0.0722 (8)
H90.30450.13030.35220.087*
C100.1167 (5)0.1073 (4)0.2996 (3)0.1118 (13)
H10A0.07080.10300.24800.134*
H10B0.05380.09740.35150.134*
C110.6357 (2)0.20232 (19)0.35234 (12)0.0414 (4)
C120.5655 (3)0.2651 (2)0.42343 (13)0.0469 (5)
C130.5809 (3)0.2177 (2)0.50477 (14)0.0616 (6)
H130.53600.26100.55200.074*
C140.6615 (4)0.1076 (3)0.51736 (16)0.0670 (7)
H140.67210.07660.57260.080*
C150.7263 (3)0.0438 (2)0.44686 (15)0.0550 (6)
C160.7139 (3)0.0899 (2)0.36483 (14)0.0474 (5)
H160.75790.04570.31780.057*
C170.3948 (3)0.36633 (19)−0.10491 (13)0.0529 (6)
H17A0.35500.4297−0.14320.064*
H17B0.50440.3799−0.09340.064*
C180.4535 (3)0.14377 (19)−0.09764 (15)0.0547 (6)
H18A0.42320.0750−0.12500.066*
H18B0.39770.1464−0.04020.066*
C190.6323 (4)0.1299 (3)−0.09123 (19)0.0726 (8)
H190.69980.1201−0.14200.087*
C200.7008 (5)0.1304 (3)−0.0213 (3)0.1042 (12)
H20A0.63750.14000.03080.125*
H20B0.81400.1212−0.02260.125*
C210.2219 (3)0.30691 (18)−0.27923 (13)0.0428 (5)
C220.0825 (3)0.2487 (2)−0.25724 (16)0.0539 (6)
C23−0.0632 (3)0.2931 (3)−0.2852 (2)0.0703 (8)
H23−0.15530.2530−0.27100.084*
C24−0.0753 (3)0.3962 (3)−0.3342 (2)0.0723 (8)
H24−0.17480.4257−0.35330.087*
C250.0607 (3)0.4551 (2)−0.35453 (17)0.0591 (6)
C260.2105 (3)0.41098 (19)−0.32823 (14)0.0468 (5)
H260.30240.4509−0.34330.056*
S10.63115 (7)0.25666 (5)0.24397 (3)0.04469 (14)
S20.41781 (6)0.25211 (5)−0.25007 (3)0.04245 (14)
N10.4463 (2)0.25790 (15)0.22148 (11)0.0450 (4)
N20.3983 (2)0.25128 (15)−0.14661 (11)0.0485 (4)
O10.7286 (2)0.16884 (15)0.19430 (10)0.0610 (4)
O20.6734 (2)0.37546 (14)0.23770 (10)0.0586 (4)
O30.4524 (2)0.13258 (14)−0.27629 (10)0.0560 (4)
Cl10.45440 (9)0.40108 (6)0.41341 (4)0.06439 (18)
Cl20.82694 (11)−0.09625 (7)0.45968 (5)0.0831 (2)
Cl30.08862 (9)0.12043 (6)−0.19397 (5)0.0722 (2)
Cl40.04722 (11)0.58805 (7)−0.41244 (6)0.0902 (3)
O40.52548 (18)0.33697 (15)−0.28380 (10)0.0525 (4)
U11U22U33U12U13U23
C10.0560 (13)0.0353 (10)0.0367 (10)−0.0047 (9)−0.0038 (9)−0.0011 (8)
C20.0565 (13)0.0350 (10)0.0379 (11)0.0030 (9)−0.0044 (9)−0.0015 (8)
C30.0557 (14)0.0599 (14)0.0517 (14)0.0045 (11)0.0003 (11)−0.0044 (11)
C40.0500 (14)0.0834 (19)0.0707 (18)0.0048 (13)−0.0112 (13)−0.0129 (14)
C50.0723 (17)0.0652 (16)0.0524 (14)0.0078 (13)−0.0229 (13)−0.0080 (12)
C60.0699 (15)0.0351 (10)0.0371 (11)−0.0007 (10)−0.0072 (10)−0.0013 (8)
C70.0587 (13)0.0416 (11)0.0335 (10)−0.0001 (9)0.0011 (9)−0.0039 (8)
C80.0685 (15)0.0386 (11)0.0630 (15)−0.0089 (10)−0.0144 (12)0.0006 (10)
C90.0738 (19)0.0669 (17)0.080 (2)−0.0249 (14)−0.0178 (15)0.0206 (14)
C100.083 (2)0.132 (3)0.127 (3)−0.044 (2)−0.020 (2)0.029 (3)
C110.0436 (11)0.0504 (12)0.0306 (10)−0.0091 (9)−0.0017 (8)−0.0018 (8)
C120.0524 (12)0.0527 (12)0.0363 (11)−0.0080 (10)−0.0027 (9)−0.0050 (9)
C130.0766 (17)0.0754 (17)0.0310 (11)−0.0037 (14)0.0019 (11)−0.0058 (11)
C140.0852 (19)0.0777 (18)0.0365 (12)−0.0043 (15)−0.0051 (12)0.0085 (12)
C150.0603 (14)0.0558 (14)0.0485 (13)−0.0063 (11)−0.0069 (11)0.0089 (10)
C160.0489 (12)0.0559 (13)0.0379 (11)−0.0069 (10)−0.0035 (9)−0.0033 (9)
C170.0875 (18)0.0387 (11)0.0334 (11)−0.0118 (11)−0.0048 (11)0.0005 (8)
C180.0774 (17)0.0414 (12)0.0432 (12)−0.0038 (11)0.0008 (11)0.0045 (9)
C190.081 (2)0.0750 (18)0.0587 (16)0.0039 (15)−0.0086 (14)0.0118 (14)
C200.105 (3)0.114 (3)0.096 (3)0.001 (2)−0.032 (2)−0.004 (2)
C210.0441 (11)0.0470 (11)0.0377 (11)−0.0051 (9)−0.0011 (9)−0.0109 (9)
C220.0494 (13)0.0528 (13)0.0593 (14)−0.0087 (10)0.0041 (11)−0.0141 (11)
C230.0453 (14)0.0733 (18)0.093 (2)−0.0101 (12)−0.0023 (13)−0.0180 (16)
C240.0486 (14)0.0769 (19)0.093 (2)0.0034 (13)−0.0200 (14)−0.0187 (16)
C250.0648 (16)0.0526 (14)0.0609 (15)0.0052 (12)−0.0172 (12)−0.0116 (11)
C260.0500 (12)0.0480 (12)0.0436 (12)−0.0043 (9)−0.0085 (9)−0.0083 (9)
S10.0529 (3)0.0501 (3)0.0300 (2)−0.0060 (2)0.0017 (2)−0.0006 (2)
S20.0450 (3)0.0478 (3)0.0337 (3)−0.0032 (2)0.0003 (2)−0.0033 (2)
N10.0604 (11)0.0355 (9)0.0401 (9)−0.0053 (8)−0.0098 (8)−0.0001 (7)
N20.0749 (13)0.0377 (9)0.0324 (9)−0.0040 (8)−0.0041 (8)−0.0002 (7)
O10.0690 (11)0.0715 (11)0.0369 (8)0.0091 (9)0.0071 (7)−0.0046 (7)
O20.0689 (11)0.0584 (10)0.0504 (9)−0.0231 (8)−0.0005 (8)0.0057 (7)
O30.0645 (10)0.0540 (9)0.0468 (9)0.0077 (8)−0.0003 (7)−0.0138 (7)
Cl10.0808 (4)0.0610 (4)0.0484 (3)0.0087 (3)−0.0027 (3)−0.0135 (3)
Cl20.1044 (6)0.0696 (4)0.0707 (5)0.0120 (4)−0.0131 (4)0.0149 (4)
Cl30.0726 (4)0.0601 (4)0.0836 (5)−0.0233 (3)0.0114 (4)−0.0002 (3)
Cl40.1033 (6)0.0672 (4)0.1033 (6)0.0049 (4)−0.0444 (5)0.0105 (4)
O40.0452 (8)0.0693 (10)0.0431 (8)−0.0114 (7)−0.0023 (7)0.0070 (7)
C1—C61.384 (3)C15—C161.376 (3)
C1—C21.393 (3)C15—Cl21.732 (3)
C1—H10.9300C16—H160.9300
C2—C31.378 (3)C17—N21.478 (3)
C2—C71.502 (3)C17—H17A0.9700
C3—C41.379 (4)C17—H17B0.9700
C3—H30.9300C18—N21.472 (3)
C4—C51.369 (4)C18—C191.484 (4)
C4—H40.9300C18—H18A0.9700
C5—C61.383 (4)C18—H18B0.9700
C5—H50.9300C19—C201.281 (4)
C6—C171.507 (3)C19—H190.9300
C7—N11.476 (3)C20—H20A0.9300
C7—H7A0.9700C20—H20B0.9300
C7—H7B0.9700C21—C261.382 (3)
C8—N11.467 (3)C21—C221.393 (3)
C8—C91.475 (4)C21—S21.773 (2)
C8—H8A0.9700C22—C231.365 (4)
C8—H8B0.9700C22—Cl31.727 (3)
C9—C101.254 (4)C23—C241.373 (4)
C9—H90.9300C23—H230.9300
C10—H10A0.9300C24—C251.371 (4)
C10—H10B0.9300C24—H240.9300
C11—C161.386 (3)C25—C261.384 (3)
C11—C121.391 (3)C25—Cl41.728 (3)
C11—S11.784 (2)C26—H260.9300
C12—C131.375 (3)S1—O21.4226 (16)
C12—Cl11.724 (2)S1—O11.4227 (16)
C13—C141.372 (4)S1—N11.6011 (19)
C13—H130.9300S2—O31.4249 (16)
C14—C151.378 (4)S2—O41.4281 (16)
C14—H140.9300S2—N21.6112 (18)
C6—C1—C2120.9 (2)N2—C17—C6110.33 (18)
C6—C1—H1119.6N2—C17—H17A109.6
C2—C1—H1119.6C6—C17—H17A109.6
C3—C2—C1119.0 (2)N2—C17—H17B109.6
C3—C2—C7121.2 (2)C6—C17—H17B109.6
C1—C2—C7119.7 (2)H17A—C17—H17B108.1
C2—C3—C4120.2 (2)N2—C18—C19113.2 (2)
C2—C3—H3119.9N2—C18—H18A108.9
C4—C3—H3119.9C19—C18—H18A108.9
C5—C4—C3120.4 (3)N2—C18—H18B108.9
C5—C4—H4119.8C19—C18—H18B108.9
C3—C4—H4119.8H18A—C18—H18B107.7
C4—C5—C6120.7 (2)C20—C19—C18125.2 (3)
C4—C5—H5119.7C20—C19—H19117.4
C6—C5—H5119.7C18—C19—H19117.4
C5—C6—C1118.8 (2)C19—C20—H20A120.0
C5—C6—C17121.4 (2)C19—C20—H20B120.0
C1—C6—C17119.7 (2)H20A—C20—H20B120.0
N1—C7—C2109.52 (16)C26—C21—C22119.4 (2)
N1—C7—H7A109.8C26—C21—S2117.30 (16)
C2—C7—H7A109.8C22—C21—S2123.27 (18)
N1—C7—H7B109.8C23—C22—C21120.2 (2)
C2—C7—H7B109.8C23—C22—Cl3118.4 (2)
H7A—C7—H7B108.2C21—C22—Cl3121.38 (19)
N1—C8—C9111.8 (2)C22—C23—C24120.7 (3)
N1—C8—H8A109.2C22—C23—H23119.6
C9—C8—H8A109.2C24—C23—H23119.6
N1—C8—H8B109.2C25—C24—C23119.4 (3)
C9—C8—H8B109.2C25—C24—H24120.3
H8A—C8—H8B107.9C23—C24—H24120.3
C10—C9—C8125.5 (3)C24—C25—C26121.1 (2)
C10—C9—H9117.3C24—C25—Cl4120.3 (2)
C8—C9—H9117.3C26—C25—Cl4118.6 (2)
C9—C10—H10A120.0C21—C26—C25119.2 (2)
C9—C10—H10B120.0C21—C26—H26120.4
H10A—C10—H10B120.0C25—C26—H26120.4
C16—C11—C12119.06 (19)O2—S1—O1118.98 (11)
C16—C11—S1116.79 (15)O2—S1—N1107.96 (10)
C12—C11—S1124.15 (17)O1—S1—N1108.42 (10)
C13—C12—C11119.9 (2)O2—S1—C11109.61 (10)
C13—C12—Cl1117.98 (18)O1—S1—C11104.72 (10)
C11—C12—Cl1122.09 (17)N1—S1—C11106.50 (9)
C14—C13—C12121.1 (2)O3—S2—O4118.28 (10)
C14—C13—H13119.5O3—S2—N2108.01 (9)
C12—C13—H13119.5O4—S2—N2110.76 (10)
C13—C14—C15119.0 (2)O3—S2—C21108.82 (10)
C13—C14—H14120.5O4—S2—C21105.88 (10)
C15—C14—H14120.5N2—S2—C21104.16 (10)
C16—C15—C14121.0 (2)C8—N1—C7117.11 (18)
C16—C15—Cl2118.46 (19)C8—N1—S1117.93 (15)
C14—C15—Cl2120.56 (19)C7—N1—S1123.99 (14)
C15—C16—C11119.9 (2)C18—N2—C17117.55 (18)
C15—C16—H16120.0C18—N2—S2119.85 (15)
C11—C16—H16120.0C17—N2—S2117.37 (14)
C6—C1—C2—C3−1.0 (3)C23—C24—C25—Cl4−177.5 (2)
C6—C1—C2—C7174.88 (18)C22—C21—C26—C25−0.1 (3)
C1—C2—C3—C41.1 (3)S2—C21—C26—C25178.15 (17)
C7—C2—C3—C4−174.8 (2)C24—C25—C26—C21−1.3 (4)
C2—C3—C4—C5−0.1 (4)Cl4—C25—C26—C21177.70 (16)
C3—C4—C5—C6−0.9 (4)C16—C11—S1—O2−134.09 (17)
C4—C5—C6—C11.0 (4)C12—C11—S1—O246.3 (2)
C4—C5—C6—C17178.5 (2)C16—C11—S1—O1−5.38 (19)
C2—C1—C6—C50.0 (3)C12—C11—S1—O1175.01 (19)
C2—C1—C6—C17−177.50 (18)C16—C11—S1—N1109.37 (17)
C3—C2—C7—N1114.2 (2)C12—C11—S1—N1−70.3 (2)
C1—C2—C7—N1−61.7 (2)C26—C21—S2—O3−125.84 (16)
N1—C8—C9—C10123.0 (4)C22—C21—S2—O352.3 (2)
C16—C11—C12—C133.0 (3)C26—C21—S2—O42.29 (18)
S1—C11—C12—C13−177.43 (19)C22—C21—S2—O4−179.54 (18)
C16—C11—C12—Cl1−175.59 (17)C26—C21—S2—N2119.15 (16)
S1—C11—C12—Cl14.0 (3)C22—C21—S2—N2−62.7 (2)
C11—C12—C13—C14−1.5 (4)C9—C8—N1—C7−65.1 (3)
Cl1—C12—C13—C14177.1 (2)C9—C8—N1—S1104.1 (2)
C12—C13—C14—C15−0.6 (4)C2—C7—N1—C8−61.9 (2)
C13—C14—C15—C161.2 (4)C2—C7—N1—S1129.61 (17)
C13—C14—C15—Cl2−179.3 (2)O2—S1—N1—C8178.66 (16)
C14—C15—C16—C110.2 (4)O1—S1—N1—C848.51 (19)
Cl2—C15—C16—C11−179.29 (17)C11—S1—N1—C8−63.70 (18)
C12—C11—C16—C15−2.3 (3)O2—S1—N1—C7−12.98 (19)
S1—C11—C16—C15178.04 (18)O1—S1—N1—C7−143.13 (16)
C5—C6—C17—N2−63.4 (3)C11—S1—N1—C7104.66 (17)
C1—C6—C17—N2114.1 (2)C19—C18—N2—C17−73.6 (3)
N2—C18—C19—C20116.5 (3)C19—C18—N2—S280.2 (2)
C26—C21—C22—C231.2 (3)C6—C17—N2—C18−58.5 (3)
S2—C21—C22—C23−176.92 (19)C6—C17—N2—S2147.10 (17)
C26—C21—C22—Cl3−178.38 (16)O3—S2—N2—C1814.2 (2)
S2—C21—C22—Cl33.5 (3)O4—S2—N2—C18−116.77 (18)
C21—C22—C23—C24−1.0 (4)C21—S2—N2—C18129.81 (18)
Cl3—C22—C23—C24178.6 (2)O3—S2—N2—C17168.06 (17)
C22—C23—C24—C25−0.3 (4)O4—S2—N2—C1737.1 (2)
C23—C24—C25—C261.5 (4)C21—S2—N2—C17−76.35 (19)
D—H···AD—HH···AD···AD—H···A
C8—H8A···O3i0.972.593.422 (3)144
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
C8—H8A⋯O3i0.972.593.422 (3)144

Symmetry code: (i) .

  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.  N,N'-Diethyl-N,N'-[1,3-phenylene-bis(methyl-ene)]dibenzene-sulfonamide.

Authors:  Islam Ullah Khan; Hira Ahmad; William T A Harrison; Tahir Ali Sheikh
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-10-29

3.  N,N'-[1,3-Phenylenebis(methyl-ene)]dibenzene-sulfonamide.

Authors:  Islam Ullah Khan; Hira Ahmad; William T A Harrison
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-10-29
  3 in total

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