N,N′-{[Ethane-1,2-diylbis(­oxy)]bis­(ethane-2,1-di­yl)}bis­(4-methyl­benzene­sulfonamide)

The asymmetric unit of the title compound, C₂₀H₂₈N₂O₆S₂, contains one half-mol­ecule, related to the other half by a twofold rotation axis. The two aromatic rings of the mol­ecule make a dihedral angle of 50.91 (7)°. The O—CH₂—CH₂—O and N—CH₂—CH₂—O fragments both adopt gauche conformations, with torsion angles of 76.0 (4) and 70.4 (3)°, respectively. In the crystal, adjacent mol­ecules are linked through N—H...O hydrogen bonds into chains along the a-axis direction. The chains are further connected via C—H...O inter­actions into a two-dimensional supra­molecular network in the ac plane.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.053
• wR factor = 0.150
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0043 Ang
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          6

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          60 Perc.

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

The title compound (Fig. 1) was obtained through the condensation reaction of 1,8-diamino-3,6-dioxaoctane with p-toluenesulfonyl chloride. A twofold rotation axis passes through the mid-point of C10—C10' bond (symmetry code: ' = -x + 2, y, -z + 3/2), the asymmetric unit therefore comprises one half of the molecule. The two symmetry related aromatic rings in the molecule make a dihedral angle of 50.91 (7)°. Similar to what was observed in a related structure (Polyakova et al., 1990), the O—CH₂—CH₂—O and N—CH₂—CH₂—O fragments adopt the gauche conformations with torsion angles of 76.0 (4) and 70.4 (3)° respectively. The S—O bond distances [1.423 (2) and 1.433 (2) Å] and S—N bond distance [1.608 (2) Å] are comparable to the values found in the literature (Ding et al., 2003; Polyakova et al., 1990). The crystal packing of the molecule shows layers in the ac plane formed by N—H···O and C—H···O interactions (Table 1, Fig. 2)

Related literature

For similar structures, see: Polyakova et al. (1990); Ding et al. (2003).

S2. Experimental

A solution of p-toluenesulfonyl chloride (2.83 g, 1.48 mmol) in dry dichloromethane (25 ml) was added drop wise to a dichloromethane solution (25 ml) of 1,8-diamino-3,6-dioxaoctane (1 g, 0.675 mmol) and triethylamine (2.34 ml, 1.69 mmol) at 273 K. The mixture was stirred at room temperature overnight, washed with water and saturated solution of NaHCO₃ (3 x 10 ml) and dried over MgSO₄. The organic layer was evaporated and the residue was dissolved in methanol. The colorless crystals of the title compound were obtained through slow evaporation of the methanolic solution at room temperature (m.p. = 361–363 K).

S3. Refinement

C-bound hydrogen atoms were located at the calculated positions and refined in riding mode with C—H distances of 0.93 (aryl), 0.96 (methyl) and 0.97 (methylene) Å. The amino hydrogen atom was found in a difference Fourier map and refined with a distance restraint of N—H 0.86 (2) Å. For H atoms, U_iso(H) were set to 1.2 (1.5 for methyl) U_eq(carrier atoms).

Computing details

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures

	Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Symmetry code: ' = -x + 2, y, -z + 3/2.
	Fig. 2. The 2-D array in the ac plane formed by N—H···O and C—H···O hydrogen bonds, depicted as dashed lines.

N,N'-{[Ethane-1,2-diylbis(oxy)]bis(ethane-2,1-diyl)}bis(4- methylbenzenesulfonamide)

Crystal data

C20H28N2O6S2	F(000) = 968
Mr = 456.56	Dx = 1.380 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1589 reflections
a = 11.135 (7) Å	θ = 2.9–25.7°
b = 9.220 (6) Å	µ = 0.28 mm^−1
c = 21.452 (15) Å	T = 296 K
β = 93.680 (12)°	Plate, colorless
V = 2198 (3) Å^3	0.23 × 0.14 × 0.04 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer	1983 independent reflections
Radiation source: fine-focus sealed tube	1558 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ and ω scans	θmax = 25.3°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.938, Tmax = 0.989	k = −11→11
5135 measured reflections	l = −17→25

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0846P)^2 + 0.5056P] where P = (Fo^2 + 2Fc^2)/3
1983 reflections	(Δ/σ)max = 0.001
140 parameters	Δρmax = 0.32 e Å^−3
1 restraint	Δρmin = −0.36 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.51163 (5)	0.03617 (7)	0.64470 (3)	0.0440 (3)
O1	0.48265 (19)	−0.0655 (2)	0.59612 (9)	0.0590 (6)
O2	0.41953 (16)	0.0823 (2)	0.68398 (9)	0.0561 (5)
O3	0.87638 (18)	0.0318 (2)	0.72055 (10)	0.0567 (6)
N1	0.6163 (2)	−0.0329 (2)	0.69058 (11)	0.0464 (6)
H1	0.614 (3)	0.002 (3)	0.7255 (9)	0.056*
C1	0.7115 (3)	0.5726 (4)	0.52722 (19)	0.0769 (10)
H1A	0.7314	0.6430	0.5592	0.115*
H1B	0.6528	0.6126	0.4973	0.115*
H1C	0.7827	0.5473	0.5066	0.115*
C2	0.6609 (2)	0.4389 (3)	0.55625 (15)	0.0518 (7)
C3	0.6610 (2)	0.4248 (3)	0.62001 (15)	0.0533 (7)
H3	0.6933	0.4992	0.6452	0.064*
C4	0.6151 (2)	0.3047 (3)	0.64781 (13)	0.0488 (7)
H4	0.6153	0.2980	0.6911	0.059*
C5	0.5681 (2)	0.1927 (3)	0.60972 (12)	0.0398 (6)
C6	0.5678 (2)	0.2038 (3)	0.54560 (13)	0.0512 (7)
H6	0.5374	0.1288	0.5202	0.061*
C7	0.6131 (3)	0.3270 (3)	0.51958 (14)	0.0594 (8)
H7	0.6116	0.3352	0.4763	0.071*
C8	0.7215 (3)	−0.1019 (3)	0.66646 (15)	0.0578 (8)
H8A	0.6986	−0.1426	0.6257	0.069*
H8B	0.7461	−0.1816	0.6939	0.069*
C9	0.8272 (3)	−0.0037 (4)	0.66034 (14)	0.0566 (8)
H9A	0.8873	−0.0518	0.6369	0.068*
H9B	0.8019	0.0839	0.6381	0.068*
C10	0.9623 (3)	0.1465 (3)	0.72024 (14)	0.0570 (8)
H10A	0.9210	0.2387	0.7150	0.068*
H10B	1.0129	0.1338	0.6855	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0341 (4)	0.0516 (4)	0.0450 (4)	−0.0066 (3)	−0.0080 (3)	0.0044 (3)
O1	0.0642 (13)	0.0572 (11)	0.0529 (12)	−0.0192 (10)	−0.0164 (10)	−0.0014 (9)
O2	0.0341 (10)	0.0774 (13)	0.0567 (12)	−0.0015 (9)	0.0011 (9)	0.0128 (10)
O3	0.0480 (11)	0.0616 (12)	0.0595 (13)	−0.0071 (9)	−0.0041 (10)	0.0074 (10)
N1	0.0402 (12)	0.0549 (14)	0.0428 (13)	0.0016 (10)	−0.0072 (11)	−0.0002 (10)
C1	0.067 (2)	0.0605 (18)	0.102 (3)	−0.0117 (17)	−0.004 (2)	0.0204 (19)
C2	0.0369 (14)	0.0502 (15)	0.068 (2)	0.0001 (12)	−0.0021 (14)	0.0101 (14)
C3	0.0412 (14)	0.0467 (14)	0.071 (2)	−0.0039 (12)	−0.0036 (14)	−0.0096 (14)
C4	0.0417 (14)	0.0558 (15)	0.0478 (16)	−0.0024 (12)	−0.0043 (12)	−0.0049 (13)
C5	0.0296 (12)	0.0452 (13)	0.0440 (14)	0.0015 (10)	−0.0033 (11)	0.0013 (11)
C6	0.0518 (16)	0.0545 (15)	0.0463 (16)	−0.0087 (13)	−0.0055 (13)	−0.0009 (13)
C7	0.0644 (19)	0.0631 (18)	0.0499 (17)	−0.0079 (15)	−0.0023 (15)	0.0103 (14)
C8	0.0500 (16)	0.0562 (16)	0.0658 (19)	0.0092 (13)	−0.0086 (15)	−0.0111 (15)
C9	0.0423 (15)	0.0745 (19)	0.0526 (18)	0.0121 (14)	−0.0004 (14)	−0.0021 (15)
C10	0.0504 (16)	0.0494 (15)	0.071 (2)	0.0000 (13)	0.0026 (14)	0.0071 (14)

Geometric parameters (Å, º)

S1—O1	1.423 (2)	C3—H3	0.9300
S1—O2	1.433 (2)	C4—C5	1.398 (4)
S1—N1	1.608 (2)	C4—H4	0.9300
S1—C5	1.761 (3)	C5—C6	1.379 (4)
O3—C9	1.409 (3)	C6—C7	1.376 (4)
O3—C10	1.426 (3)	C6—H6	0.9300
N1—C8	1.457 (4)	C7—H7	0.9300
N1—H1	0.816 (17)	C8—C9	1.497 (4)
C1—C2	1.507 (4)	C8—H8A	0.9700
C1—H1A	0.9600	C8—H8B	0.9700
C1—H1B	0.9600	C9—H9A	0.9700
C1—H1C	0.9600	C9—H9B	0.9700
C2—C3	1.374 (4)	C10—C10^i	1.482 (6)
C2—C7	1.383 (4)	C10—H10A	0.9700
C3—C4	1.372 (4)	C10—H10B	0.9700
O1—S1—O2	119.26 (13)	C6—C5—S1	120.5 (2)
O1—S1—N1	108.00 (13)	C4—C5—S1	119.1 (2)
O2—S1—N1	106.01 (13)	C7—C6—C5	119.2 (3)
O1—S1—C5	107.33 (13)	C7—C6—H6	120.4
O2—S1—C5	107.22 (13)	C5—C6—H6	120.4
N1—S1—C5	108.68 (12)	C6—C7—C2	121.5 (3)
C9—O3—C10	112.9 (2)	C6—C7—H7	119.2
C8—N1—S1	121.6 (2)	C2—C7—H7	119.2
C8—N1—H1	124 (2)	N1—C8—C9	114.9 (2)
S1—N1—H1	110 (2)	N1—C8—H8A	108.5
C2—C1—H1A	109.5	C9—C8—H8A	108.5
C2—C1—H1B	109.5	N1—C8—H8B	108.5
H1A—C1—H1B	109.5	C9—C8—H8B	108.5
C2—C1—H1C	109.5	H8A—C8—H8B	107.5
H1A—C1—H1C	109.5	O3—C9—C8	108.8 (2)
H1B—C1—H1C	109.5	O3—C9—H9A	109.9
C3—C2—C7	118.2 (3)	C8—C9—H9A	109.9
C3—C2—C1	120.8 (3)	O3—C9—H9B	109.9
C7—C2—C1	121.0 (3)	C8—C9—H9B	109.9
C4—C3—C2	122.2 (3)	H9A—C9—H9B	108.3
C4—C3—H3	118.9	O3—C10—C10^i	109.8 (2)
C2—C3—H3	118.9	O3—C10—H10A	109.7
C3—C4—C5	118.6 (3)	C10^i—C10—H10A	109.7
C3—C4—H4	120.7	O3—C10—H10B	109.7
C5—C4—H4	120.7	C10^i—C10—H10B	109.7
C6—C5—C4	120.3 (2)	H10A—C10—H10B	108.2

Symmetry code: (i) −x+2, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^ii	0.82 (2)	2.14 (2)	2.944 (3)	171 (3)
C6—H6···O1^iii	0.93	2.56	3.311 (4)	138

Symmetry codes: (ii) −x+1, y, −z+3/2; (iii) −x+1, −y, −z+1.