N,N'-Bis(3-methylbut-2-enyl)-N,N'-(1,4-phenylene)dibenzenesulfonamide.

The complete mol-ecule of the title compound, C(28)H(32)N(2)O(4)S(2), is generated by a crystallographic inversion centre. The dihedral angle between the central and pendant aromatic rings is 46.78 (7)°. The C(ar)-S-N-C(ar) (ar = aromatic) torsion angle is 73.64 (15)° and the bond-angle sum for the N atom is 350.4°. In the crystal, weak C-H⋯O inter-actions link the mol-ecules, forming a two-dimensional network lying parallel to the bc plane.

Related literature

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

Experimental

Crystal data

C28H32N2O4S2

M = 524.68

Monoclinic,

a = 10.6574 (4) Å

b = 20.8073 (8) Å

c = 6.4015 (2) Å

β = 105.673 (2)°

V = 1366.76 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.50 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

11502 measured reflections

2667 independent reflections

1931 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.104

S = 1.03

2667 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.31 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/S1600536811045661/su2338sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045661/su2338Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045661/su2338Isup3.cml

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

C28H32N2O4S2	F(000) = 556
Mr = 524.68	Dx = 1.275 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3403 reflections
a = 10.6574 (4) Å	θ = 2.0–28.4°
b = 20.8073 (8) Å	µ = 0.23 mm−1
c = 6.4015 (2) Å	T = 296 K
β = 105.673 (2)°	Block, brown
V = 1366.76 (8) Å3	0.50 × 0.20 × 0.15 mm
Z = 2

Bruker APEXII CCD diffractometer	1931 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 26.0°, θmin = 2.8°
ω scans	h = −13→13
11502 measured reflections	k = −25→25
2667 independent reflections	l = −7→7

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0426P)2 + 0.3607P] where P = (Fo2 + 2Fc2)/3
2667 reflections	(Δ/σ)max = 0.001
165 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.31 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	0.1596 (2)	0.38177 (9)	0.4486 (3)	0.0504 (5)
C2	0.1301 (2)	0.33079 (11)	0.3050 (4)	0.0653 (6)
H2	0.1735	0.2918	0.3386	0.078*
C3	0.0355 (3)	0.33861 (14)	0.1113 (4)	0.0812 (8)
H3	0.0168	0.3050	0.0117	0.097*
C4	−0.0307 (3)	0.39525 (15)	0.0648 (4)	0.0864 (8)
H4	−0.0953	0.3998	−0.0650	0.104*
C5	−0.0026 (3)	0.44530 (13)	0.2077 (4)	0.0780 (7)
H5	−0.0489	0.4836	0.1758	0.094*
C6	0.0940 (2)	0.43918 (11)	0.3987 (4)	0.0617 (6)
H6	0.1149	0.4737	0.4940	0.074*
C7	0.4581 (2)	0.32309 (9)	0.4971 (4)	0.0563 (5)
H7A	0.4214	0.2838	0.5369	0.068*
H7B	0.4229	0.3295	0.3422	0.068*
C8	0.6019 (2)	0.31741 (9)	0.5505 (3)	0.0536 (5)
H8	0.6433	0.3027	0.6892	0.064*
C9	0.6779 (2)	0.33075 (10)	0.4248 (3)	0.0549 (5)
C10	0.8227 (3)	0.32188 (14)	0.5036 (4)	0.0874 (8)
H10A	0.8445	0.3029	0.6456	0.131*
H10B	0.8650	0.3629	0.5101	0.131*
H10C	0.8513	0.2942	0.4057	0.131*
C11	0.6331 (3)	0.35544 (14)	0.1992 (4)	0.0806 (8)
H11A	0.5396	0.3548	0.1524	0.121*
H11B	0.6672	0.3288	0.1051	0.121*
H11C	0.6634	0.3987	0.1943	0.121*
C12	0.45972 (18)	0.44109 (8)	0.5560 (3)	0.0407 (4)
C13	0.41589 (19)	0.46298 (9)	0.3456 (3)	0.0475 (5)
H13	0.3591	0.4380	0.2412	0.057*
C14	0.54372 (19)	0.47809 (9)	0.7100 (3)	0.0471 (5)
H14	0.5734	0.4633	0.8519	0.057*
S1	0.28630 (5)	0.37450 (2)	0.68836 (8)	0.05203 (19)
N1	0.42238 (16)	0.37861 (7)	0.6175 (2)	0.0466 (4)
O1	0.28181 (15)	0.42921 (7)	0.8196 (2)	0.0655 (4)
O2	0.28035 (15)	0.31145 (7)	0.7724 (3)	0.0727 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0536 (12)	0.0418 (12)	0.0643 (12)	−0.0040 (10)	0.0305 (10)	−0.0043 (9)
C2	0.0595 (15)	0.0542 (14)	0.0857 (16)	−0.0051 (11)	0.0258 (13)	−0.0142 (12)
C3	0.0786 (19)	0.083 (2)	0.0821 (17)	−0.0127 (16)	0.0222 (15)	−0.0308 (15)
C4	0.0791 (19)	0.106 (2)	0.0718 (16)	0.0036 (17)	0.0157 (14)	−0.0058 (16)
C5	0.0846 (18)	0.0751 (18)	0.0774 (17)	0.0202 (15)	0.0273 (15)	0.0130 (14)
C6	0.0752 (16)	0.0511 (14)	0.0636 (13)	0.0042 (12)	0.0272 (12)	−0.0042 (10)
C7	0.0658 (15)	0.0336 (11)	0.0745 (13)	−0.0052 (10)	0.0277 (11)	−0.0031 (10)
C8	0.0649 (14)	0.0450 (12)	0.0524 (11)	0.0090 (10)	0.0182 (10)	0.0054 (9)
C9	0.0607 (14)	0.0512 (13)	0.0535 (11)	0.0067 (10)	0.0167 (10)	0.0007 (9)
C10	0.0680 (17)	0.116 (2)	0.0790 (16)	0.0122 (16)	0.0220 (14)	0.0009 (15)
C11	0.0872 (19)	0.096 (2)	0.0641 (14)	0.0167 (15)	0.0301 (14)	0.0185 (13)
C12	0.0507 (11)	0.0296 (9)	0.0451 (10)	−0.0018 (8)	0.0185 (9)	0.0006 (7)
C13	0.0579 (13)	0.0392 (11)	0.0440 (10)	−0.0108 (9)	0.0111 (9)	−0.0051 (8)
C14	0.0608 (13)	0.0413 (11)	0.0386 (9)	−0.0039 (10)	0.0123 (9)	0.0044 (8)
S1	0.0631 (4)	0.0435 (3)	0.0564 (3)	−0.0048 (3)	0.0282 (3)	0.0049 (2)
N1	0.0558 (10)	0.0311 (9)	0.0573 (9)	−0.0037 (7)	0.0225 (8)	0.0026 (7)
O1	0.0823 (11)	0.0655 (10)	0.0571 (8)	−0.0043 (8)	0.0330 (8)	−0.0125 (7)
O2	0.0808 (11)	0.0557 (10)	0.0903 (11)	−0.0069 (8)	0.0380 (9)	0.0261 (8)

C1—C6	1.378 (3)	C9—C11	1.485 (3)
C1—C2	1.383 (3)	C9—C10	1.500 (3)
C1—S1	1.756 (2)	C10—H10A	0.9600
C2—C3	1.381 (3)	C10—H10B	0.9600
C2—H2	0.9300	C10—H10C	0.9600
C3—C4	1.364 (4)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C4—C5	1.365 (4)	C11—H11C	0.9600
C4—H4	0.9300	C12—C14	1.374 (2)
C5—C6	1.375 (3)	C12—C13	1.379 (2)
C5—H5	0.9300	C12—N1	1.445 (2)
C6—H6	0.9300	C13—C14i	1.378 (2)
C7—C8	1.482 (3)	C13—H13	0.9300
C7—N1	1.494 (2)	C14—C13i	1.378 (2)
C7—H7A	0.9700	C14—H14	0.9300
C7—H7B	0.9700	S1—O1	1.4233 (14)
C8—C9	1.317 (3)	S1—O2	1.4257 (14)
C8—H8	0.9300	S1—N1	1.6345 (16)
C6—C1—C2	120.1 (2)	C9—C10—H10A	109.5
C6—C1—S1	120.00 (16)	C9—C10—H10B	109.5
C2—C1—S1	119.85 (17)	H10A—C10—H10B	109.5
C3—C2—C1	119.1 (2)	C9—C10—H10C	109.5
C3—C2—H2	120.5	H10A—C10—H10C	109.5
C1—C2—H2	120.5	H10B—C10—H10C	109.5
C4—C3—C2	120.5 (2)	C9—C11—H11A	109.5
C4—C3—H3	119.8	C9—C11—H11B	109.5
C2—C3—H3	119.8	H11A—C11—H11B	109.5
C3—C4—C5	120.4 (3)	C9—C11—H11C	109.5
C3—C4—H4	119.8	H11A—C11—H11C	109.5
C5—C4—H4	119.8	H11B—C11—H11C	109.5
C4—C5—C6	120.1 (2)	C14—C12—C13	119.93 (16)
C4—C5—H5	120.0	C14—C12—N1	118.85 (15)
C6—C5—H5	120.0	C13—C12—N1	121.18 (16)
C5—C6—C1	119.9 (2)	C14i—C13—C12	119.95 (17)
C5—C6—H6	120.1	C14i—C13—H13	120.0
C1—C6—H6	120.1	C12—C13—H13	120.0
C8—C7—N1	109.54 (16)	C12—C14—C13i	120.12 (16)
C8—C7—H7A	109.8	C12—C14—H14	119.9
N1—C7—H7A	109.8	C13i—C14—H14	119.9
C8—C7—H7B	109.8	O1—S1—O2	120.08 (9)
N1—C7—H7B	109.8	O1—S1—N1	107.20 (9)
H7A—C7—H7B	108.2	O2—S1—N1	106.63 (9)
C9—C8—C7	127.64 (19)	O1—S1—C1	107.84 (9)
C9—C8—H8	116.2	O2—S1—C1	107.89 (10)
C7—C8—H8	116.2	N1—S1—C1	106.46 (8)
C8—C9—C11	125.3 (2)	C12—N1—C7	115.31 (14)
C8—C9—C10	121.0 (2)	C12—N1—S1	116.94 (12)
C11—C9—C10	113.7 (2)	C7—N1—S1	118.15 (12)
C6—C1—C2—C3	0.7 (3)	C6—C1—S1—O2	143.23 (16)
S1—C1—C2—C3	−176.16 (17)	C2—C1—S1—O2	−39.90 (18)
C1—C2—C3—C4	−1.9 (4)	C6—C1—S1—N1	−102.63 (17)
C2—C3—C4—C5	1.1 (4)	C2—C1—S1—N1	74.23 (17)
C3—C4—C5—C6	0.8 (4)	C14—C12—N1—C7	−119.44 (19)
C4—C5—C6—C1	−2.0 (4)	C13—C12—N1—C7	58.5 (2)
C2—C1—C6—C5	1.2 (3)	C14—C12—N1—S1	94.90 (18)
S1—C1—C6—C5	178.08 (17)	C13—C12—N1—S1	−87.15 (19)
N1—C7—C8—C9	−108.2 (2)	C8—C7—N1—C12	65.6 (2)
C7—C8—C9—C11	0.7 (4)	C8—C7—N1—S1	−149.18 (14)
C7—C8—C9—C10	−179.6 (2)	O1—S1—N1—C12	−41.56 (15)
C14—C12—C13—C14i	−0.1 (3)	O2—S1—N1—C12	−171.36 (13)
N1—C12—C13—C14i	−177.99 (17)	C1—S1—N1—C12	73.64 (15)
C13—C12—C14—C13i	0.1 (3)	O1—S1—N1—C7	173.77 (14)
N1—C12—C14—C13i	178.04 (17)	O2—S1—N1—C7	43.97 (17)
C6—C1—S1—O1	12.14 (19)	C1—S1—N1—C7	−71.02 (16)
C2—C1—S1—O1	−170.99 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ii	0.93	2.52	3.398 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.93	2.52	3.398 (3)	158

Symmetry code: (i) .