N,N'-Bis(3,3-dimethyl-all-yl)-N,N'-(prop-ane-1,3-diyl)dibenzene-sulfonamide.

In the title compound, C(25)H(34)N(2)O(4)S(2), the conformation of the linking N-C-C-C-N chain is gauche-anti [torsion angles = -68.49 (19) and 167.95 (14)°]. The dihedral angle between the aromatic rings is 89.64 (6)°.

Related literature

For the related structures of N-[3-(benzene­sulfonamido)­prop­yl]benzene­sulfonamide and N,N′-(propane-1,3-di­yl)bis­(p-toluene­sulfonamide), see: Sheikh et al. (2011 ▶) and Khan et al. (2011 ▶), respectively.

Experimental

Crystal data

C25H34N2O4S2

M = 490.66

Monoclinic,

a = 10.3019 (2) Å

b = 16.3962 (4) Å

c = 16.0500 (4) Å

β = 108.449 (1)°

V = 2571.71 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.50 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

40701 measured reflections

5059 independent reflections

4011 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.102

S = 1.05

5059 reflections

302 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.24 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/S1600536811050562/zs2161sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050562/zs2161Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811050562/zs2161Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H34N2O4S2	F(000) = 1048
Mr = 490.66	Dx = 1.267 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4846 reflections
a = 10.3019 (2) Å	θ = 2.4–28.3°
b = 16.3962 (4) Å	µ = 0.24 mm−1
c = 16.0500 (4) Å	T = 296 K
β = 108.449 (1)°	Faceted block, colourless
V = 2571.71 (10) Å3	0.50 × 0.25 × 0.20 mm
Z = 4

Bruker APEXII CCD diffractometer	4011 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
graphite	θmax = 26.0°, θmin = 2.4°
ω scans	h = −12→12
40701 measured reflections	k = −20→20
5059 independent reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0458P)2 + 0.7949P] where P = (Fo2 + 2Fc2)/3
5059 reflections	(Δ/σ)max = 0.001
302 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.21354 (16)	−0.05844 (10)	0.30778 (10)	0.0423 (4)
C2	0.1634 (2)	−0.13588 (11)	0.31257 (12)	0.0552 (4)
H2	0.0878	−0.1434	0.3315	0.066*
C3	0.2272 (3)	−0.20195 (12)	0.28881 (13)	0.0702 (6)
H3	0.1948	−0.2543	0.2924	0.084*
C4	0.3379 (2)	−0.19098 (15)	0.26002 (14)	0.0741 (6)
H4	0.3803	−0.2358	0.2443	0.089*
C5	0.3857 (2)	−0.11425 (15)	0.25434 (14)	0.0693 (6)
H5	0.4603	−0.1070	0.2342	0.083*
C6	0.32444 (18)	−0.04722 (12)	0.27827 (12)	0.0533 (4)
H6	0.3575	0.0050	0.2745	0.064*
C7	0.34337 (16)	0.07689 (10)	0.48435 (11)	0.0475 (4)
H7A	0.3758	0.0929	0.4362	0.057*
H7B	0.4104	0.0402	0.5220	0.057*
C8	0.33084 (19)	0.15195 (11)	0.53634 (11)	0.0520 (4)
H8A	0.2891	0.1367	0.5804	0.062*
H8B	0.4216	0.1729	0.5666	0.062*
C9	0.24648 (18)	0.21859 (10)	0.47923 (11)	0.0455 (4)
H9A	0.2977	0.2418	0.4437	0.055*
H9B	0.1634	0.1949	0.4398	0.055*
C10	−0.06124 (17)	0.30932 (12)	0.43729 (11)	0.0525 (4)
C11	−0.10347 (19)	0.25338 (14)	0.36942 (12)	0.0602 (5)
H11	−0.0725	0.1998	0.3773	0.072*
C12	−0.1930 (2)	0.27902 (17)	0.28927 (13)	0.0721 (6)
H12	−0.2202	0.2425	0.2426	0.087*
C13	−0.2414 (2)	0.35669 (18)	0.27828 (16)	0.0784 (7)
H13	−0.3024	0.3727	0.2245	0.094*
C14	−0.2010 (2)	0.41129 (17)	0.34560 (17)	0.0815 (7)
H14	−0.2352	0.4642	0.3377	0.098*
C15	−0.1093 (2)	0.38832 (14)	0.42576 (14)	0.0684 (5)
H15	−0.0805	0.4259	0.4713	0.082*
C16	0.17868 (17)	−0.02590 (10)	0.50808 (11)	0.0466 (4)
H16A	0.0913	−0.0510	0.4775	0.056*
H16B	0.1691	0.0026	0.5588	0.056*
C17	0.28411 (17)	−0.09122 (10)	0.53891 (12)	0.0500 (4)
H17	0.3022	−0.1228	0.4957	0.060*
C18	0.35404 (17)	−0.10877 (11)	0.62076 (12)	0.0507 (4)
C19	0.4535 (2)	−0.17811 (14)	0.64300 (18)	0.0794 (7)
H19A	0.4279	−0.2157	0.6809	0.119*
H19B	0.5437	−0.1575	0.6723	0.119*
H19C	0.4529	−0.2056	0.5901	0.119*
C20	0.3395 (2)	−0.06355 (14)	0.69819 (13)	0.0698 (6)
H20A	0.4242	−0.0659	0.7456	0.105*
H20B	0.2682	−0.0880	0.7164	0.105*
H20C	0.3167	−0.0077	0.6823	0.105*
C21	0.26420 (19)	0.36620 (11)	0.52107 (14)	0.0598 (5)
H21A	0.2230	0.4064	0.5492	0.072*
H21B	0.2401	0.3800	0.4593	0.072*
C22	0.41617 (19)	0.36853 (11)	0.56158 (13)	0.0570 (5)
H22	0.4499	0.3590	0.6217	0.068*
C23	0.50789 (19)	0.38257 (10)	0.52170 (12)	0.0534 (4)
C24	0.6577 (2)	0.38660 (15)	0.57265 (16)	0.0778 (6)
H24A	0.7053	0.3441	0.5531	0.117*
H24B	0.6701	0.3796	0.6341	0.117*
H24C	0.6935	0.4387	0.5634	0.117*
C25	0.4767 (2)	0.39749 (13)	0.42503 (13)	0.0687 (5)
H25A	0.5287	0.3604	0.4019	0.103*
H25B	0.5006	0.4525	0.4157	0.103*
H25C	0.3808	0.3891	0.3957	0.103*
S1	0.13963 (4)	0.02601 (3)	0.34402 (3)	0.04583 (13)
S2	0.05674 (5)	0.27959 (3)	0.53939 (3)	0.05475 (14)
N1	0.21229 (13)	0.03391 (8)	0.44902 (8)	0.0415 (3)
N2	0.20938 (14)	0.28434 (8)	0.53033 (9)	0.0471 (3)
O1	0.17552 (15)	0.09743 (8)	0.30526 (8)	0.0640 (4)
O2	−0.00108 (12)	0.00677 (10)	0.32939 (9)	0.0681 (4)
O3	0.03302 (15)	0.19581 (9)	0.55383 (9)	0.0731 (4)
O4	0.04980 (16)	0.33927 (11)	0.60232 (9)	0.0835 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0443 (8)	0.0454 (9)	0.0345 (8)	−0.0005 (7)	0.0086 (6)	−0.0038 (7)
C2	0.0622 (11)	0.0518 (11)	0.0466 (10)	−0.0106 (9)	0.0099 (8)	−0.0023 (8)
C3	0.0915 (16)	0.0431 (11)	0.0566 (12)	−0.0016 (10)	−0.0041 (11)	−0.0093 (9)
C4	0.0788 (15)	0.0715 (15)	0.0575 (12)	0.0225 (12)	0.0011 (11)	−0.0207 (11)
C5	0.0568 (11)	0.0875 (17)	0.0642 (13)	0.0109 (11)	0.0197 (10)	−0.0173 (11)
C6	0.0516 (10)	0.0572 (11)	0.0527 (10)	−0.0033 (8)	0.0190 (8)	−0.0081 (8)
C7	0.0428 (9)	0.0455 (9)	0.0535 (10)	0.0049 (7)	0.0141 (7)	0.0040 (8)
C8	0.0537 (10)	0.0494 (10)	0.0440 (9)	0.0010 (8)	0.0031 (8)	0.0001 (8)
C9	0.0548 (10)	0.0393 (9)	0.0406 (9)	−0.0002 (7)	0.0128 (7)	−0.0005 (7)
C10	0.0441 (9)	0.0697 (12)	0.0467 (10)	−0.0065 (8)	0.0187 (8)	0.0031 (9)
C11	0.0517 (10)	0.0731 (13)	0.0529 (11)	−0.0179 (9)	0.0126 (8)	0.0005 (10)
C12	0.0562 (12)	0.1058 (19)	0.0498 (11)	−0.0274 (12)	0.0103 (9)	0.0004 (11)
C13	0.0538 (12)	0.116 (2)	0.0645 (14)	−0.0023 (13)	0.0175 (10)	0.0288 (14)
C14	0.0756 (15)	0.0935 (18)	0.0827 (17)	0.0225 (13)	0.0353 (13)	0.0278 (14)
C15	0.0696 (13)	0.0773 (15)	0.0645 (13)	0.0066 (11)	0.0302 (11)	0.0013 (11)
C16	0.0457 (9)	0.0525 (10)	0.0452 (9)	0.0054 (7)	0.0194 (7)	0.0055 (8)
C17	0.0541 (10)	0.0451 (10)	0.0562 (11)	0.0058 (8)	0.0251 (8)	0.0056 (8)
C18	0.0438 (9)	0.0475 (10)	0.0630 (11)	−0.0008 (7)	0.0202 (8)	0.0158 (8)
C19	0.0620 (12)	0.0681 (14)	0.1120 (18)	0.0155 (10)	0.0332 (12)	0.0454 (13)
C20	0.0659 (12)	0.0840 (15)	0.0531 (11)	−0.0020 (11)	0.0097 (10)	0.0099 (10)
C21	0.0589 (11)	0.0413 (10)	0.0753 (13)	−0.0053 (8)	0.0156 (10)	−0.0067 (9)
C22	0.0615 (11)	0.0498 (11)	0.0531 (11)	−0.0114 (9)	0.0087 (9)	−0.0063 (8)
C23	0.0587 (11)	0.0406 (9)	0.0563 (11)	−0.0075 (8)	0.0118 (9)	−0.0039 (8)
C24	0.0613 (13)	0.0879 (16)	0.0791 (15)	−0.0081 (11)	0.0149 (11)	0.0044 (12)
C25	0.0820 (14)	0.0602 (13)	0.0629 (12)	−0.0052 (10)	0.0213 (11)	0.0020 (10)
S1	0.0477 (2)	0.0487 (3)	0.0404 (2)	0.00946 (18)	0.01282 (18)	0.00255 (18)
S2	0.0538 (3)	0.0726 (3)	0.0396 (2)	−0.0046 (2)	0.01724 (19)	−0.0030 (2)
N1	0.0468 (7)	0.0399 (7)	0.0391 (7)	0.0034 (6)	0.0154 (6)	0.0006 (6)
N2	0.0496 (8)	0.0396 (8)	0.0514 (8)	−0.0048 (6)	0.0150 (6)	−0.0080 (6)
O1	0.0970 (10)	0.0473 (7)	0.0508 (7)	0.0128 (7)	0.0278 (7)	0.0122 (6)
O2	0.0410 (7)	0.0977 (11)	0.0602 (8)	0.0125 (7)	0.0085 (6)	−0.0028 (7)
O3	0.0737 (9)	0.0857 (10)	0.0600 (8)	−0.0195 (8)	0.0212 (7)	0.0211 (7)
O4	0.0794 (10)	0.1212 (13)	0.0523 (8)	0.0133 (9)	0.0240 (7)	−0.0253 (8)

C1—C6	1.381 (2)	C16—N1	1.479 (2)
C1—C2	1.382 (2)	C16—C17	1.494 (2)
C1—S1	1.7651 (16)	C16—H16A	0.9700
C2—C3	1.382 (3)	C16—H16B	0.9700
C2—H2	0.9300	C17—C18	1.315 (2)
C3—C4	1.371 (3)	C17—H17	0.9300
C3—H3	0.9300	C18—C20	1.495 (3)
C4—C5	1.365 (3)	C18—C19	1.496 (3)
C4—H4	0.9300	C19—H19A	0.9600
C5—C6	1.381 (3)	C19—H19B	0.9600
C5—H5	0.9300	C19—H19C	0.9600
C6—H6	0.9300	C20—H20A	0.9600
C7—N1	1.469 (2)	C20—H20B	0.9600
C7—C8	1.515 (2)	C20—H20C	0.9600
C7—H7A	0.9700	C21—N2	1.482 (2)
C7—H7B	0.9700	C21—C22	1.494 (3)
C8—C9	1.512 (2)	C21—H21A	0.9700
C8—H8A	0.9700	C21—H21B	0.9700
C8—H8B	0.9700	C22—C23	1.318 (3)
C9—N2	1.476 (2)	C22—H22	0.9300
C9—H9A	0.9700	C23—C25	1.502 (3)
C9—H9B	0.9700	C23—C24	1.502 (3)
C10—C15	1.378 (3)	C24—H24A	0.9600
C10—C11	1.385 (3)	C24—H24B	0.9600
C10—S2	1.7719 (18)	C24—H24C	0.9600
C11—C12	1.390 (3)	C25—H25A	0.9600
C11—H11	0.9300	C25—H25B	0.9600
C12—C13	1.359 (3)	C25—H25C	0.9600
C12—H12	0.9300	S1—O1	1.4284 (13)
C13—C14	1.363 (4)	S1—O2	1.4284 (13)
C13—H13	0.9300	S1—N1	1.6184 (13)
C14—C15	1.386 (3)	S2—O4	1.4242 (15)
C14—H14	0.9300	S2—O3	1.4270 (15)
C15—H15	0.9300	S2—N2	1.6263 (14)
C6—C1—C2	120.38 (16)	C18—C17—C16	126.79 (17)
C6—C1—S1	119.91 (13)	C18—C17—H17	116.6
C2—C1—S1	119.66 (13)	C16—C17—H17	116.6
C3—C2—C1	119.10 (19)	C17—C18—C20	123.69 (17)
C3—C2—H2	120.4	C17—C18—C19	121.47 (19)
C1—C2—H2	120.4	C20—C18—C19	114.83 (18)
C4—C3—C2	120.6 (2)	C18—C19—H19A	109.5
C4—C3—H3	119.7	C18—C19—H19B	109.5
C2—C3—H3	119.7	H19A—C19—H19B	109.5
C5—C4—C3	120.01 (19)	C18—C19—H19C	109.5
C5—C4—H4	120.0	H19A—C19—H19C	109.5
C3—C4—H4	120.0	H19B—C19—H19C	109.5
C4—C5—C6	120.5 (2)	C18—C20—H20A	109.5
C4—C5—H5	119.7	C18—C20—H20B	109.5
C6—C5—H5	119.7	H20A—C20—H20B	109.5
C1—C6—C5	119.36 (18)	C18—C20—H20C	109.5
C1—C6—H6	120.3	H20A—C20—H20C	109.5
C5—C6—H6	120.3	H20B—C20—H20C	109.5
N1—C7—C8	111.98 (13)	N2—C21—C22	111.09 (15)
N1—C7—H7A	109.2	N2—C21—H21A	109.4
C8—C7—H7A	109.2	C22—C21—H21A	109.4
N1—C7—H7B	109.2	N2—C21—H21B	109.4
C8—C7—H7B	109.2	C22—C21—H21B	109.4
H7A—C7—H7B	107.9	H21A—C21—H21B	108.0
C9—C8—C7	112.71 (14)	C23—C22—C21	127.35 (19)
C9—C8—H8A	109.1	C23—C22—H22	116.3
C7—C8—H8A	109.1	C21—C22—H22	116.3
C9—C8—H8B	109.1	C22—C23—C25	125.31 (18)
C7—C8—H8B	109.1	C22—C23—C24	120.94 (19)
H8A—C8—H8B	107.8	C25—C23—C24	113.74 (18)
N2—C9—C8	113.03 (14)	C23—C24—H24A	109.5
N2—C9—H9A	109.0	C23—C24—H24B	109.5
C8—C9—H9A	109.0	H24A—C24—H24B	109.5
N2—C9—H9B	109.0	C23—C24—H24C	109.5
C8—C9—H9B	109.0	H24A—C24—H24C	109.5
H9A—C9—H9B	107.8	H24B—C24—H24C	109.5
C15—C10—C11	120.45 (19)	C23—C25—H25A	109.5
C15—C10—S2	119.67 (15)	C23—C25—H25B	109.5
C11—C10—S2	119.88 (16)	H25A—C25—H25B	109.5
C10—C11—C12	118.6 (2)	C23—C25—H25C	109.5
C10—C11—H11	120.7	H25A—C25—H25C	109.5
C12—C11—H11	120.7	H25B—C25—H25C	109.5
C13—C12—C11	120.8 (2)	O1—S1—O2	119.91 (9)
C13—C12—H12	119.6	O1—S1—N1	106.84 (8)
C11—C12—H12	119.6	O2—S1—N1	107.44 (7)
C12—C13—C14	120.4 (2)	O1—S1—C1	107.54 (8)
C12—C13—H13	119.8	O2—S1—C1	107.08 (8)
C14—C13—H13	119.8	N1—S1—C1	107.48 (7)
C13—C14—C15	120.3 (2)	O4—S2—O3	119.78 (10)
C13—C14—H14	119.8	O4—S2—N2	107.31 (8)
C15—C14—H14	119.8	O3—S2—N2	106.30 (8)
C10—C15—C14	119.4 (2)	O4—S2—C10	107.05 (10)
C10—C15—H15	120.3	O3—S2—C10	108.20 (9)
C14—C15—H15	120.3	N2—S2—C10	107.68 (8)
N1—C16—C17	113.23 (13)	C7—N1—C16	116.35 (13)
N1—C16—H16A	108.9	C7—N1—S1	120.42 (11)
C17—C16—H16A	108.9	C16—N1—S1	119.30 (11)
N1—C16—H16B	108.9	C9—N2—C21	115.59 (14)
C17—C16—H16B	108.9	C9—N2—S2	116.26 (11)
H16A—C16—H16B	107.7	C21—N2—S2	117.54 (12)
C6—C1—C2—C3	1.1 (3)	C6—C1—S1—N1	−92.54 (15)
S1—C1—C2—C3	−176.26 (14)	C2—C1—S1—N1	84.80 (15)
C1—C2—C3—C4	−0.7 (3)	C15—C10—S2—O4	17.51 (18)
C2—C3—C4—C5	−0.2 (3)	C11—C10—S2—O4	−163.10 (14)
C3—C4—C5—C6	0.7 (3)	C15—C10—S2—O3	147.88 (15)
C2—C1—C6—C5	−0.6 (3)	C11—C10—S2—O3	−32.73 (16)
S1—C1—C6—C5	176.70 (14)	C15—C10—S2—N2	−97.60 (15)
C4—C5—C6—C1	−0.2 (3)	C11—C10—S2—N2	81.79 (15)
N1—C7—C8—C9	−68.49 (19)	C8—C7—N1—C16	−85.97 (17)
C7—C8—C9—N2	167.95 (14)	C8—C7—N1—S1	116.52 (14)
C15—C10—C11—C12	1.2 (3)	C17—C16—N1—C7	−57.52 (19)
S2—C10—C11—C12	−178.17 (14)	C17—C16—N1—S1	100.26 (15)
C10—C11—C12—C13	−1.9 (3)	O1—S1—N1—C7	−31.34 (14)
C11—C12—C13—C14	1.0 (3)	O2—S1—N1—C7	−161.22 (12)
C12—C13—C14—C15	0.5 (3)	C1—S1—N1—C7	83.85 (13)
C11—C10—C15—C14	0.3 (3)	O1—S1—N1—C16	171.81 (11)
S2—C10—C15—C14	179.66 (15)	O2—S1—N1—C16	41.93 (13)
C13—C14—C15—C10	−1.2 (3)	C1—S1—N1—C16	−73.01 (13)
N1—C16—C17—C18	121.44 (18)	C8—C9—N2—C21	117.43 (17)
C16—C17—C18—C20	−0.9 (3)	C8—C9—N2—S2	−98.69 (16)
C16—C17—C18—C19	177.71 (17)	C22—C21—N2—C9	−68.0 (2)
N2—C21—C22—C23	117.5 (2)	C22—C21—N2—S2	148.57 (14)
C21—C22—C23—C25	−1.5 (3)	O4—S2—N2—C9	170.32 (12)
C21—C22—C23—C24	177.22 (19)	O3—S2—N2—C9	41.04 (14)
C6—C1—S1—O1	22.18 (16)	C10—S2—N2—C9	−74.74 (14)
C2—C1—S1—O1	−160.49 (14)	O4—S2—N2—C21	−46.52 (16)
C6—C1—S1—O2	152.29 (14)	O3—S2—N2—C21	−175.80 (13)
C2—C1—S1—O2	−30.38 (16)	C10—S2—N2—C21	68.42 (15)