Literature DB >> 22259436

2,2',5,5'-Tetra-chloro-N,N'-diethyl-N,N'-[benzene-1,3-diylbis(methyl-ene)]dibenzene-sulfonamide.

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

Abstract

In the title compound, C(24)H(24)Cl(4)N(2)O(4)S(2), the dihedral angles between the central benzene ring and the pendant rings are 58.09 (10) and 62.59 (10)°. The dihedral angle between the pendant rings is 81.64 (9)°. Both sulfonamide groups lie to the same side of the central ring but the C-S-N-C torsion angles [73.09 (16) and -117.35 (14)] and S-N-C-C torsion angles [-143.80 (14) and -111.45 (16)°] differ significantly for the two pendant chains. The N atoms are close to planar (bond angle sums = 356.4 and 359.5°). In the crystal, weak C-H⋯O and C-H⋯Cl inter-actions link the mol-ecules.

Entities:  

Year:  2011        PMID: 22259436      PMCID: PMC3254356          DOI: 10.1107/S1600536811045326

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

C24H24Cl4N2O4S2 M = 610.37 Triclinic, a = 8.0396 (2) Å b = 11.1512 (3) Å c = 15.5723 (3) Å α = 87.454 (1)° β = 83.378 (1)° γ = 87.995 (1)° V = 1384.77 (6) Å3 Z = 2 Mo Kα radiation μ = 0.61 mm−1 T = 296 K 0.50 × 0.35 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer 25271 measured reflections 6905 independent reflections 5380 reflections with I > 2σ(I) R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.036 wR(F 2) = 0.102 S = 1.04 6905 reflections 327 parameters H-atom parameters constrained Δρmax = 0.47 e Å−3 Δρmin = −0.38 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/S1600536811045326/su2337sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045326/su2337Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811045326/su2337Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C24H24Cl4N2O4S2Z = 2
Mr = 610.37F(000) = 628
Triclinic, P1Dx = 1.464 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0396 (2) ÅCell parameters from 6905 reflections
b = 11.1512 (3) Åθ = 2.2–28.1°
c = 15.5723 (3) ŵ = 0.61 mm1
α = 87.454 (1)°T = 296 K
β = 83.378 (1)°Chnnk, colourless
γ = 87.995 (1)°0.50 × 0.35 × 0.30 mm
V = 1384.77 (6) Å3
Bruker APEXII CCD diffractometer5380 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
graphiteθmax = 28.4°, θmin = 3.0°
ω scansh = −8→10
25271 measured reflectionsk = −14→14
6905 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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0462P)2 + 0.4193P] where P = (Fo2 + 2Fc2)/3
6905 reflections(Δ/σ)max = 0.001
327 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = −0.38 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
C10.6756 (2)0.63163 (16)0.43821 (11)0.0454 (4)
H10.56230.62420.43330.055*
C20.7280 (3)0.63672 (17)0.51940 (12)0.0502 (4)
C30.8970 (3)0.6480 (2)0.52549 (15)0.0695 (6)
H30.93400.65250.57970.083*
C41.0103 (3)0.6527 (3)0.45304 (17)0.0776 (7)
H41.12360.65940.45830.093*
C50.9572 (3)0.6475 (2)0.37192 (14)0.0622 (5)
H51.03470.65090.32280.075*
C60.7890 (2)0.63737 (16)0.36384 (11)0.0452 (4)
C70.6016 (3)0.63174 (18)0.59876 (12)0.0579 (5)
H7A0.49350.61130.58250.069*
H7B0.63590.56960.63920.069*
C80.5407 (3)0.85534 (19)0.58997 (13)0.0571 (5)
H8A0.61710.86070.53710.069*
H8B0.55530.92560.62250.069*
C90.3646 (4)0.8577 (3)0.5668 (2)0.0967 (9)
H9A0.34630.92740.53040.145*
H9B0.28750.86030.61870.145*
H9C0.34730.78670.53670.145*
C100.75316 (19)0.69614 (16)0.77750 (10)0.0395 (3)
C110.8994 (2)0.75963 (17)0.75576 (12)0.0462 (4)
C121.0466 (2)0.71855 (19)0.78590 (14)0.0567 (5)
H121.14380.76140.77170.068*
C131.0506 (2)0.6145 (2)0.83684 (14)0.0578 (5)
H131.14990.58730.85740.069*
C140.9069 (2)0.55140 (17)0.85701 (12)0.0476 (4)
C150.7572 (2)0.59124 (16)0.82812 (11)0.0417 (4)
H150.66050.54790.84260.050*
C160.7269 (2)0.63890 (16)0.27608 (11)0.0462 (4)
H16A0.82160.63380.23170.055*
H16B0.65860.56970.27240.055*
C170.7074 (3)0.86554 (18)0.26202 (15)0.0604 (5)
H17A0.74580.87390.31820.073*
H17B0.62510.92950.25380.073*
C180.8521 (4)0.8787 (3)0.1935 (2)0.0934 (9)
H18A0.88940.95980.19100.140*
H18B0.81810.86020.13860.140*
H18C0.94190.82460.20690.140*
C190.4012 (2)0.80340 (16)0.14908 (10)0.0414 (4)
C200.4657 (2)0.74445 (17)0.07480 (11)0.0470 (4)
C210.4306 (3)0.7893 (2)−0.00540 (12)0.0597 (5)
H210.47220.7489−0.05470.072*
C220.3354 (3)0.8928 (2)−0.01335 (13)0.0620 (5)
H220.31190.9223−0.06760.074*
C230.2751 (2)0.95234 (18)0.05987 (12)0.0514 (4)
C240.3068 (2)0.90861 (17)0.14088 (11)0.0458 (4)
H240.26490.94970.18980.055*
S10.55636 (5)0.74464 (4)0.74476 (3)0.04106 (11)
S20.42957 (6)0.74915 (4)0.25594 (3)0.04402 (11)
N10.5864 (2)0.74805 (14)0.64078 (9)0.0489 (4)
N20.62753 (19)0.74925 (13)0.26098 (10)0.0475 (3)
O10.51855 (17)0.86403 (12)0.77167 (9)0.0560 (3)
O20.44311 (14)0.65269 (12)0.77704 (8)0.0515 (3)
O30.37690 (17)0.62781 (12)0.26631 (9)0.0563 (3)
O40.34712 (19)0.83655 (14)0.31150 (8)0.0622 (4)
Cl10.90284 (7)0.88984 (5)0.69119 (4)0.06287 (14)
Cl20.91046 (7)0.41825 (5)0.91822 (4)0.06768 (16)
Cl30.59191 (7)0.61629 (5)0.07875 (3)0.06285 (15)
Cl40.15880 (8)1.08554 (5)0.05174 (4)0.07195 (17)
U11U22U33U12U13U23
C10.0522 (10)0.0428 (10)0.0418 (9)−0.0030 (7)−0.0065 (7)−0.0035 (7)
C20.0699 (12)0.0418 (10)0.0399 (9)0.0025 (8)−0.0106 (8)−0.0043 (7)
C30.0735 (14)0.0824 (16)0.0571 (13)0.0149 (12)−0.0270 (11)−0.0146 (11)
C40.0519 (12)0.107 (2)0.0773 (16)0.0142 (12)−0.0204 (11)−0.0194 (14)
C50.0492 (11)0.0776 (15)0.0591 (12)0.0081 (10)−0.0047 (9)−0.0072 (11)
C60.0494 (9)0.0430 (10)0.0429 (9)0.0052 (7)−0.0054 (7)−0.0032 (7)
C70.0879 (15)0.0477 (11)0.0384 (9)−0.0080 (10)−0.0066 (9)−0.0019 (8)
C80.0692 (13)0.0528 (11)0.0463 (10)0.0054 (9)−0.0006 (9)0.0103 (9)
C90.0856 (19)0.106 (2)0.099 (2)0.0127 (16)−0.0304 (16)0.0276 (18)
C100.0340 (7)0.0486 (10)0.0360 (8)−0.0002 (7)−0.0017 (6)−0.0088 (7)
C110.0416 (9)0.0473 (10)0.0486 (10)−0.0037 (7)0.0021 (7)−0.0083 (8)
C120.0345 (8)0.0634 (13)0.0716 (13)−0.0056 (8)−0.0007 (8)−0.0081 (10)
C130.0368 (9)0.0688 (13)0.0688 (13)0.0047 (8)−0.0101 (8)−0.0098 (10)
C140.0446 (9)0.0508 (11)0.0478 (10)0.0054 (8)−0.0077 (7)−0.0067 (8)
C150.0363 (8)0.0506 (10)0.0383 (8)−0.0013 (7)−0.0034 (6)−0.0068 (7)
C160.0526 (10)0.0469 (10)0.0382 (9)0.0034 (8)−0.0012 (7)−0.0060 (7)
C170.0711 (13)0.0451 (11)0.0688 (13)−0.0084 (9)−0.0234 (11)0.0018 (9)
C180.098 (2)0.0845 (19)0.097 (2)−0.0371 (16)−0.0047 (16)0.0179 (16)
C190.0412 (8)0.0490 (10)0.0340 (8)−0.0053 (7)−0.0023 (6)−0.0035 (7)
C200.0479 (9)0.0528 (11)0.0394 (9)−0.0017 (8)0.0001 (7)−0.0069 (8)
C210.0703 (13)0.0731 (14)0.0347 (9)0.0004 (11)−0.0004 (8)−0.0085 (9)
C220.0715 (13)0.0772 (15)0.0375 (10)0.0008 (11)−0.0103 (9)0.0033 (9)
C230.0531 (10)0.0530 (11)0.0486 (10)−0.0030 (8)−0.0100 (8)0.0023 (8)
C240.0452 (9)0.0519 (11)0.0406 (9)−0.0028 (8)−0.0044 (7)−0.0054 (8)
S10.0364 (2)0.0499 (3)0.0361 (2)0.00241 (17)−0.00185 (15)−0.00196 (17)
S20.0484 (2)0.0491 (3)0.0329 (2)−0.00132 (18)0.00197 (16)−0.00125 (17)
N10.0683 (10)0.0431 (8)0.0353 (7)0.0015 (7)−0.0079 (7)0.0006 (6)
N20.0529 (8)0.0411 (8)0.0501 (8)−0.0039 (6)−0.0123 (7)−0.0002 (6)
O10.0568 (8)0.0580 (8)0.0521 (8)0.0143 (6)−0.0022 (6)−0.0118 (6)
O20.0339 (6)0.0686 (9)0.0508 (7)−0.0053 (6)−0.0034 (5)0.0098 (6)
O30.0571 (8)0.0549 (8)0.0549 (8)−0.0138 (6)0.0022 (6)0.0074 (6)
O40.0727 (9)0.0730 (10)0.0378 (7)0.0149 (7)0.0046 (6)−0.0090 (6)
Cl10.0584 (3)0.0556 (3)0.0720 (3)−0.0115 (2)0.0042 (2)0.0037 (2)
Cl20.0640 (3)0.0647 (3)0.0758 (4)0.0053 (2)−0.0212 (3)0.0105 (3)
Cl30.0713 (3)0.0645 (3)0.0507 (3)0.0141 (3)0.0007 (2)−0.0128 (2)
Cl40.0829 (4)0.0666 (4)0.0675 (3)0.0136 (3)−0.0205 (3)0.0039 (3)
C1—C21.382 (2)C14—C151.385 (2)
C1—C61.389 (3)C14—Cl21.730 (2)
C1—H10.9300C15—H150.9300
C2—C31.383 (3)C16—N21.468 (2)
C2—C71.507 (3)C16—H16A0.9700
C3—C41.366 (3)C16—H16B0.9700
C3—H30.9300C17—N21.469 (2)
C4—C51.383 (3)C17—C181.491 (4)
C4—H40.9300C17—H17A0.9700
C5—C61.381 (3)C17—H17B0.9700
C5—H50.9300C18—H18A0.9600
C6—C161.507 (2)C18—H18B0.9600
C7—N11.474 (2)C18—H18C0.9600
C7—H7A0.9700C19—C241.384 (2)
C7—H7B0.9700C19—C201.394 (2)
C8—N11.465 (2)C19—S21.7820 (17)
C8—C91.499 (3)C20—C211.380 (3)
C8—H8A0.9700C20—Cl31.726 (2)
C8—H8B0.9700C21—C221.371 (3)
C9—H9A0.9600C21—H210.9300
C9—H9B0.9600C22—C231.376 (3)
C9—H9C0.9600C22—H220.9300
C10—C151.383 (2)C23—C241.380 (3)
C10—C111.394 (2)C23—Cl41.735 (2)
C10—S11.7769 (16)C24—H240.9300
C11—C121.379 (3)S1—O11.4256 (14)
C11—Cl11.7282 (19)S1—O21.4307 (13)
C12—C131.378 (3)S1—N11.6082 (15)
C12—H120.9300S2—O41.4267 (14)
C13—C141.372 (3)S2—O31.4286 (14)
C13—H130.9300S2—N21.6025 (16)
C2—C1—C6121.26 (18)N2—C16—C6110.74 (14)
C2—C1—H1119.4N2—C16—H16A109.5
C6—C1—H1119.4C6—C16—H16A109.5
C1—C2—C3118.56 (19)N2—C16—H16B109.5
C1—C2—C7119.97 (19)C6—C16—H16B109.5
C3—C2—C7121.47 (18)H16A—C16—H16B108.1
C4—C3—C2120.9 (2)N2—C17—C18112.5 (2)
C4—C3—H3119.6N2—C17—H17A109.1
C2—C3—H3119.6C18—C17—H17A109.1
C3—C4—C5120.3 (2)N2—C17—H17B109.1
C3—C4—H4119.8C18—C17—H17B109.1
C5—C4—H4119.8H17A—C17—H17B107.8
C6—C5—C4120.1 (2)C17—C18—H18A109.5
C6—C5—H5120.0C17—C18—H18B109.5
C4—C5—H5120.0H18A—C18—H18B109.5
C5—C6—C1118.91 (17)C17—C18—H18C109.5
C5—C6—C16121.04 (17)H18A—C18—H18C109.5
C1—C6—C16119.97 (16)H18B—C18—H18C109.5
N1—C7—C2110.85 (16)C24—C19—C20119.20 (16)
N1—C7—H7A109.5C24—C19—S2117.24 (13)
C2—C7—H7A109.5C20—C19—S2123.55 (14)
N1—C7—H7B109.5C21—C20—C19119.87 (18)
C2—C7—H7B109.5C21—C20—Cl3117.85 (15)
H7A—C7—H7B108.1C19—C20—Cl3122.28 (14)
N1—C8—C9114.22 (19)C22—C21—C20120.85 (19)
N1—C8—H8A108.7C22—C21—H21119.6
C9—C8—H8A108.7C20—C21—H21119.6
N1—C8—H8B108.7C21—C22—C23119.20 (18)
C9—C8—H8B108.7C21—C22—H22120.4
H8A—C8—H8B107.6C23—C22—H22120.4
C8—C9—H9A109.5C22—C23—C24121.06 (19)
C8—C9—H9B109.5C22—C23—Cl4120.31 (15)
H9A—C9—H9B109.5C24—C23—Cl4118.63 (16)
C8—C9—H9C109.5C23—C24—C19119.79 (17)
H9A—C9—H9C109.5C23—C24—H24120.1
H9B—C9—H9C109.5C19—C24—H24120.1
C15—C10—C11119.74 (15)O1—S1—O2118.08 (8)
C15—C10—S1117.14 (12)O1—S1—N1108.23 (8)
C11—C10—S1123.11 (14)O2—S1—N1110.99 (8)
C12—C11—C10119.87 (18)O1—S1—C10109.11 (8)
C12—C11—Cl1118.30 (15)O2—S1—C10105.20 (8)
C10—C11—Cl1121.83 (14)N1—S1—C10104.35 (8)
C13—C12—C11120.47 (18)O4—S2—O3118.77 (9)
C13—C12—H12119.8O4—S2—N2109.82 (9)
C11—C12—H12119.8O3—S2—N2108.25 (8)
C14—C13—C12119.45 (18)O4—S2—C19105.17 (9)
C14—C13—H13120.3O3—S2—C19108.50 (8)
C12—C13—H13120.3N2—S2—C19105.53 (8)
C13—C14—C15121.21 (18)C8—N1—C7118.50 (15)
C13—C14—Cl2120.22 (15)C8—N1—S1120.83 (13)
C15—C14—Cl2118.56 (15)C7—N1—S1117.12 (12)
C10—C15—C14119.25 (16)C16—N2—C17118.81 (16)
C10—C15—H15120.4C16—N2—S2122.54 (12)
C14—C15—H15120.4C17—N2—S2118.14 (13)
C6—C1—C2—C30.1 (3)C22—C23—C24—C190.2 (3)
C6—C1—C2—C7179.28 (17)Cl4—C23—C24—C19−179.11 (14)
C1—C2—C3—C4−0.7 (3)C20—C19—C24—C231.3 (3)
C7—C2—C3—C4−179.9 (2)S2—C19—C24—C23−177.43 (14)
C2—C3—C4—C50.7 (4)C15—C10—S1—O1124.12 (14)
C3—C4—C5—C6−0.1 (4)C11—C10—S1—O1−54.76 (16)
C4—C5—C6—C1−0.5 (3)C15—C10—S1—O2−3.50 (15)
C4—C5—C6—C16176.4 (2)C11—C10—S1—O2177.63 (14)
C2—C1—C6—C50.5 (3)C15—C10—S1—N1−120.40 (14)
C2—C1—C6—C16−176.41 (17)C11—C10—S1—N160.73 (16)
C1—C2—C7—N1−111.1 (2)C24—C19—S2—O4−2.36 (16)
C3—C2—C7—N168.0 (2)C20—C19—S2—O4178.98 (15)
C15—C10—C11—C12−1.0 (3)C24—C19—S2—O3125.71 (14)
S1—C10—C11—C12177.85 (15)C20—C19—S2—O3−52.96 (17)
C15—C10—C11—Cl1178.88 (13)C24—C19—S2—N2−118.46 (14)
S1—C10—C11—Cl1−2.3 (2)C20—C19—S2—N262.87 (17)
C10—C11—C12—C130.5 (3)C9—C8—N1—C768.6 (3)
Cl1—C11—C12—C13−179.33 (16)C9—C8—N1—S1−89.6 (2)
C11—C12—C13—C140.4 (3)C2—C7—N1—C857.3 (2)
C12—C13—C14—C15−0.9 (3)C2—C7—N1—S1−143.80 (14)
C12—C13—C14—Cl2178.11 (16)O1—S1—N1—C8−12.41 (18)
C11—C10—C15—C140.5 (3)O2—S1—N1—C8118.67 (16)
S1—C10—C15—C14−178.43 (13)C10—S1—N1—C8−128.51 (16)
C13—C14—C15—C100.5 (3)O1—S1—N1—C7−170.82 (15)
Cl2—C14—C15—C10−178.57 (13)O2—S1—N1—C7−39.74 (17)
C5—C6—C16—N2−111.2 (2)C10—S1—N1—C773.09 (16)
C1—C6—C16—N265.6 (2)C6—C16—N2—C1760.2 (2)
C24—C19—C20—C21−2.0 (3)C6—C16—N2—S2−111.45 (16)
S2—C19—C20—C21176.64 (16)C18—C17—N2—C1661.4 (2)
C24—C19—C20—Cl3177.23 (14)C18—C17—N2—S2−126.57 (19)
S2—C19—C20—Cl3−4.1 (2)O4—S2—N2—C16129.76 (14)
C19—C20—C21—C221.2 (3)O3—S2—N2—C16−1.35 (16)
Cl3—C20—C21—C22−178.04 (17)C19—S2—N2—C16−117.35 (14)
C20—C21—C22—C230.3 (3)O4—S2—N2—C17−41.94 (17)
C21—C22—C23—C24−1.0 (3)O3—S2—N2—C17−173.06 (14)
C21—C22—C23—Cl4178.31 (17)C19—S2—N2—C1770.94 (16)
D—H···AD—HH···AD···AD—H···A
C7—H7B···O3i0.972.593.511 (2)158
C17—H17B···O1ii0.972.583.516 (3)164
C24—H24···Cl1ii0.932.833.738 (2)166
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
C7—H7B⋯O3i0.972.593.511 (2)158
C17—H17B⋯O1ii0.972.583.516 (3)164
C24—H24⋯Cl1ii0.932.833.738 (2)166

Symmetry codes: (i) ; (ii) .

  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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