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

In the title compound, C(24)H(28)N(2)O(4)S(2), the dihedral angles between the central benzene ring and the pendant rings are 77.44 (11) and 79.23 (10)°, and the dihedral angle between the pendant rings is 23.31 (12)°. Both sulfonamide groups project to the same side of the central benzene ring and the mol-ecule has approximate non-crystallographic mirror symmetry. One of the ethyl side chains is disordered over two sets of sites in a 0.526 (14):0.474 (14) ratio. In the crystal, inversion dimers linked by pairs of weak C-H⋯O inter-actions occur, generating R(2) (2)(28) loops.

Related literature

For a related structure, see: Khan et al. (2011 ▶).

Experimental

Crystal data

C24H28N2O4S2

M = 472.60

Monoclinic,

a = 9.1865 (3) Å

b = 19.0679 (7) Å

c = 14.3870 (5) Å

β = 106.122 (1)°

V = 2421.02 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.13 × 0.10 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

23272 measured reflections

6013 independent reflections

4188 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.132

S = 1.01

6013 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.38 e Å−3

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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040700/su2324sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040700/su2324Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811040700/su2324Isup3.cml

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

C24H28N2O4S2	F(000) = 1000
Mr = 472.60	Dx = 1.297 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6013 reflections
a = 9.1865 (3) Å	θ = 2.6–28.3°
b = 19.0679 (7) Å	µ = 0.25 mm−1
c = 14.3870 (5) Å	T = 296 K
β = 106.122 (1)°	Block, colourless
V = 2421.02 (15) Å3	0.13 × 0.10 × 0.09 mm
Z = 4

Bruker APEXII CCD diffractometer	4188 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 28.3°, θmin = 2.6°
ω scans	h = −12→8
23272 measured reflections	k = −24→25
6013 independent reflections	l = −17→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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.060P)2 + 0.7693P] where P = (Fo2 + 2Fc2)/3
6013 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.38 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	Occ. (<1)
C1	0.78689 (19)	0.13374 (9)	0.68904 (13)	0.0448 (4)
H1	0.7268	0.1480	0.6288	0.054*
C2	0.73697 (19)	0.08014 (9)	0.73745 (14)	0.0449 (4)
C3	0.8266 (2)	0.05935 (11)	0.82682 (15)	0.0554 (5)
H3	0.7942	0.0233	0.8598	0.066*
C4	0.9639 (2)	0.09163 (13)	0.86768 (15)	0.0614 (5)
H4	1.0237	0.0775	0.9281	0.074*
C5	1.0123 (2)	0.14489 (11)	0.81882 (15)	0.0545 (5)
H5	1.1049	0.1666	0.8466	0.065*
C6	0.92480 (19)	0.16639 (9)	0.72889 (14)	0.0452 (4)
C7	0.9798 (2)	0.22228 (10)	0.67292 (17)	0.0557 (5)
H7A	1.0849	0.2329	0.7054	0.067*
H7B	0.9751	0.2045	0.6090	0.067*
C8	1.0539 (3)	0.36406 (11)	0.56934 (15)	0.0582 (5)
C9	1.1599 (3)	0.32027 (13)	0.54866 (18)	0.0702 (6)
H9	1.1345	0.2745	0.5280	0.084*
C10	1.3050 (3)	0.34546 (17)	0.5591 (2)	0.0881 (8)
H10	1.3785	0.3162	0.5467	0.106*
C11	1.3404 (4)	0.41342 (19)	0.5877 (2)	0.0957 (10)
H11	1.4381	0.4299	0.5947	0.115*
C12	1.2346 (4)	0.45677 (18)	0.6058 (2)	0.1002 (10)
H12	1.2595	0.5030	0.6238	0.120*
C13	1.0910 (3)	0.43270 (13)	0.5975 (2)	0.0796 (7)
H13	1.0188	0.4623	0.6107	0.096*
C14	0.5875 (2)	0.04462 (10)	0.69110 (16)	0.0517 (5)
H14A	0.5908	0.0235	0.6304	0.062*
H14B	0.5708	0.0076	0.7332	0.062*
C15	0.22235 (19)	0.00993 (9)	0.59280 (13)	0.0437 (4)
C16	0.2729 (2)	−0.05564 (10)	0.57526 (16)	0.0553 (5)
H16	0.3584	−0.0602	0.5531	0.066*
C17	0.1955 (3)	−0.11417 (11)	0.59097 (18)	0.0676 (6)
H17	0.2282	−0.1586	0.5790	0.081*
C18	0.0694 (3)	−0.10715 (13)	0.62447 (19)	0.0728 (7)
H18	0.0180	−0.1469	0.6356	0.087*
C19	0.0198 (3)	−0.04250 (14)	0.64141 (18)	0.0697 (6)
H19	−0.0661	−0.0383	0.6633	0.084*
C20	0.0957 (2)	0.01662 (11)	0.62643 (16)	0.0558 (5)
H20	0.0623	0.0608	0.6388	0.067*
C21	0.9119 (3)	0.32830 (13)	0.75365 (18)	0.0700 (6)
H21A	0.9693	0.3704	0.7501	0.084*
H21B	0.9692	0.3008	0.8083	0.084*
C22A	0.7607 (7)	0.3480 (4)	0.7682 (5)	0.079 (2)*	0.526 (14)
H22A	0.7765	0.3746	0.8269	0.119*	0.526 (14)
H22B	0.7046	0.3063	0.7725	0.119*	0.526 (14)
H22C	0.7048	0.3759	0.7145	0.119*	0.526 (14)
C22B	0.7963 (9)	0.3175 (6)	0.8056 (7)	0.095 (3)*	0.474 (14)
H22D	0.8201	0.3458	0.8630	0.143*	0.474 (14)
H22E	0.7947	0.2690	0.8231	0.143*	0.474 (14)
H22F	0.6987	0.3306	0.7645	0.143*	0.474 (14)
C23	0.4252 (2)	0.12225 (12)	0.76072 (16)	0.0597 (5)
H23A	0.3194	0.1129	0.7553	0.072*
H23B	0.4857	0.0974	0.8171	0.072*
C24	0.4538 (4)	0.19853 (14)	0.7750 (2)	0.0879 (8)
H24A	0.5597	0.2078	0.7849	0.132*
H24B	0.4240	0.2138	0.8307	0.132*
H24C	0.3961	0.2234	0.7189	0.132*
S1	0.87268 (6)	0.33183 (3)	0.56484 (4)	0.05927 (16)
S2	0.32295 (5)	0.08483 (2)	0.57589 (4)	0.04724 (14)
N1	0.88989 (17)	0.28716 (8)	0.66325 (12)	0.0512 (4)
N2	0.46183 (16)	0.09500 (8)	0.67317 (12)	0.0484 (4)
O1	0.82899 (19)	0.28392 (9)	0.48611 (12)	0.0765 (5)
O2	0.77734 (19)	0.39036 (9)	0.56817 (15)	0.0850 (5)
O3	0.38878 (17)	0.07049 (8)	0.49896 (11)	0.0615 (4)
O4	0.22630 (16)	0.14401 (7)	0.57007 (12)	0.0634 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0399 (8)	0.0470 (10)	0.0441 (10)	0.0051 (7)	0.0063 (7)	−0.0007 (8)
C2	0.0399 (8)	0.0434 (10)	0.0506 (10)	0.0043 (7)	0.0113 (8)	−0.0030 (8)
C3	0.0532 (11)	0.0572 (12)	0.0570 (12)	0.0080 (9)	0.0173 (9)	0.0120 (9)
C4	0.0490 (10)	0.0816 (15)	0.0479 (11)	0.0100 (10)	0.0041 (9)	0.0077 (10)
C5	0.0358 (8)	0.0674 (13)	0.0560 (12)	0.0034 (8)	0.0057 (8)	−0.0092 (10)
C6	0.0385 (8)	0.0441 (10)	0.0540 (10)	0.0041 (7)	0.0145 (8)	−0.0031 (8)
C7	0.0427 (9)	0.0502 (11)	0.0763 (14)	0.0030 (8)	0.0200 (9)	0.0027 (10)
C8	0.0683 (12)	0.0491 (11)	0.0539 (12)	−0.0051 (9)	0.0117 (10)	0.0015 (9)
C9	0.0817 (16)	0.0574 (13)	0.0753 (15)	−0.0027 (11)	0.0281 (13)	0.0091 (11)
C10	0.0849 (18)	0.096 (2)	0.094 (2)	0.0008 (16)	0.0428 (16)	0.0184 (16)
C11	0.091 (2)	0.110 (3)	0.089 (2)	−0.0403 (19)	0.0303 (17)	0.0000 (18)
C12	0.119 (2)	0.087 (2)	0.106 (2)	−0.0455 (19)	0.049 (2)	−0.0221 (17)
C13	0.0994 (19)	0.0578 (14)	0.0856 (18)	−0.0164 (13)	0.0322 (15)	−0.0105 (13)
C14	0.0459 (9)	0.0407 (10)	0.0667 (12)	0.0010 (8)	0.0123 (9)	−0.0021 (9)
C15	0.0380 (8)	0.0434 (9)	0.0468 (10)	−0.0011 (7)	0.0072 (7)	−0.0072 (8)
C16	0.0461 (10)	0.0473 (11)	0.0698 (13)	0.0003 (8)	0.0116 (9)	−0.0116 (9)
C17	0.0636 (13)	0.0445 (11)	0.0858 (17)	−0.0032 (10)	0.0061 (12)	−0.0072 (11)
C18	0.0654 (14)	0.0633 (14)	0.0829 (17)	−0.0207 (11)	0.0091 (12)	0.0073 (12)
C19	0.0542 (12)	0.0799 (17)	0.0783 (16)	−0.0141 (11)	0.0240 (11)	−0.0028 (13)
C20	0.0475 (10)	0.0573 (12)	0.0639 (13)	−0.0006 (9)	0.0174 (9)	−0.0110 (10)
C21	0.0774 (15)	0.0623 (14)	0.0712 (15)	−0.0154 (11)	0.0223 (12)	−0.0171 (11)
C23	0.0568 (11)	0.0632 (13)	0.0605 (13)	−0.0029 (10)	0.0187 (10)	−0.0101 (10)
C24	0.107 (2)	0.0684 (16)	0.0941 (19)	−0.0111 (15)	0.0384 (17)	−0.0337 (15)
S1	0.0548 (3)	0.0474 (3)	0.0663 (3)	0.0028 (2)	0.0013 (2)	−0.0028 (2)
S2	0.0431 (2)	0.0417 (2)	0.0565 (3)	0.00114 (18)	0.0131 (2)	−0.0028 (2)
N1	0.0474 (8)	0.0412 (8)	0.0643 (10)	−0.0011 (6)	0.0140 (7)	−0.0090 (7)
N2	0.0399 (7)	0.0448 (8)	0.0598 (10)	−0.0005 (6)	0.0127 (7)	−0.0110 (7)
O1	0.0781 (10)	0.0737 (11)	0.0641 (10)	−0.0086 (8)	−0.0031 (8)	−0.0132 (8)
O2	0.0706 (10)	0.0608 (10)	0.1129 (15)	0.0211 (8)	0.0075 (10)	0.0060 (10)
O3	0.0645 (9)	0.0673 (9)	0.0570 (8)	−0.0022 (7)	0.0239 (7)	−0.0007 (7)
O4	0.0549 (8)	0.0441 (8)	0.0862 (11)	0.0089 (6)	0.0111 (7)	−0.0004 (7)

C1—C2	1.385 (3)	C16—C17	1.376 (3)
C1—C6	1.385 (2)	C16—H16	0.9300
C1—H1	0.9300	C17—C18	1.379 (3)
C2—C3	1.378 (3)	C17—H17	0.9300
C2—C14	1.510 (3)	C18—C19	1.360 (4)
C3—C4	1.380 (3)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.374 (3)
C4—C5	1.377 (3)	C19—H19	0.9300
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.382 (3)	C21—C22B	1.473 (7)
C5—H5	0.9300	C21—N1	1.484 (3)
C6—C7	1.505 (3)	C21—C22A	1.509 (6)
C7—N1	1.473 (2)	C21—H21A	0.9700
C7—H7A	0.9700	C21—H21B	0.9700
C7—H7B	0.9700	C22A—H22A	0.9600
C8—C9	1.377 (3)	C22A—H22B	0.9600
C8—C13	1.384 (3)	C22A—H22C	0.9600
C8—S1	1.759 (2)	C22B—H22D	0.9600
C9—C10	1.385 (4)	C22B—H22E	0.9600
C9—H9	0.9300	C22B—H22F	0.9600
C10—C11	1.371 (4)	C23—C24	1.482 (3)
C10—H10	0.9300	C23—N2	1.485 (3)
C11—C12	1.355 (4)	C23—H23A	0.9700
C11—H11	0.9300	C23—H23B	0.9700
C12—C13	1.370 (4)	C24—H24A	0.9600
C12—H12	0.9300	C24—H24B	0.9600
C13—H13	0.9300	C24—H24C	0.9600
C14—N2	1.469 (2)	S1—O1	1.4235 (16)
C14—H14A	0.9700	S1—O2	1.4276 (16)
C14—H14B	0.9700	S1—N1	1.6220 (18)
C15—C16	1.381 (3)	S2—O4	1.4239 (14)
C15—C20	1.385 (3)	S2—O3	1.4274 (15)
C15—S2	1.7543 (18)	S2—N2	1.6224 (16)
C2—C1—C6	121.08 (17)	C17—C18—H18	119.8
C2—C1—H1	119.5	C18—C19—C20	120.4 (2)
C6—C1—H1	119.5	C18—C19—H19	119.8
C3—C2—C1	119.08 (17)	C20—C19—H19	119.8
C3—C2—C14	121.14 (18)	C19—C20—C15	119.5 (2)
C1—C2—C14	119.76 (17)	C19—C20—H20	120.3
C2—C3—C4	120.50 (19)	C15—C20—H20	120.3
C2—C3—H3	119.7	C22B—C21—N1	115.4 (3)
C4—C3—H3	119.7	C22B—C21—C22A	31.0 (3)
C5—C4—C3	119.87 (19)	N1—C21—C22A	110.3 (3)
C5—C4—H4	120.1	C22B—C21—H21A	128.4
C3—C4—H4	120.1	N1—C21—H21A	109.6
C4—C5—C6	120.67 (18)	C22A—C21—H21A	109.6
C4—C5—H5	119.7	C22B—C21—H21B	79.5
C6—C5—H5	119.7	N1—C21—H21B	109.6
C5—C6—C1	118.79 (18)	C22A—C21—H21B	109.6
C5—C6—C7	121.08 (17)	H21A—C21—H21B	108.1
C1—C6—C7	120.09 (17)	C21—C22A—H22A	109.5
N1—C7—C6	112.47 (15)	C21—C22A—H22B	109.5
N1—C7—H7A	109.1	H22A—C22A—H22B	109.5
C6—C7—H7A	109.1	C21—C22A—H22C	109.5
N1—C7—H7B	109.1	H22A—C22A—H22C	109.5
C6—C7—H7B	109.1	H22B—C22A—H22C	109.5
H7A—C7—H7B	107.8	C21—C22B—H22D	109.5
C9—C8—C13	120.4 (2)	C21—C22B—H22E	109.5
C9—C8—S1	119.95 (17)	H22D—C22B—H22E	109.5
C13—C8—S1	119.6 (2)	C21—C22B—H22F	109.5
C8—C9—C10	118.9 (2)	H22D—C22B—H22F	109.5
C8—C9—H9	120.5	H22E—C22B—H22F	109.5
C10—C9—H9	120.5	C24—C23—N2	112.85 (19)
C11—C10—C9	120.1 (3)	C24—C23—H23A	109.0
C11—C10—H10	120.0	N2—C23—H23A	109.0
C9—C10—H10	120.0	C24—C23—H23B	109.0
C12—C11—C10	120.7 (3)	N2—C23—H23B	109.0
C12—C11—H11	119.6	H23A—C23—H23B	107.8
C10—C11—H11	119.6	C23—C24—H24A	109.5
C11—C12—C13	120.2 (3)	C23—C24—H24B	109.5
C11—C12—H12	119.9	H24A—C24—H24B	109.5
C13—C12—H12	119.9	C23—C24—H24C	109.5
C12—C13—C8	119.7 (3)	H24A—C24—H24C	109.5
C12—C13—H13	120.2	H24B—C24—H24C	109.5
C8—C13—H13	120.2	O1—S1—O2	119.23 (11)
N2—C14—C2	111.00 (15)	O1—S1—N1	107.17 (10)
N2—C14—H14A	109.4	O2—S1—N1	107.05 (10)
C2—C14—H14A	109.4	O1—S1—C8	107.96 (11)
N2—C14—H14B	109.4	O2—S1—C8	107.99 (11)
C2—C14—H14B	109.4	N1—S1—C8	106.83 (9)
H14A—C14—H14B	108.0	O4—S2—O3	119.85 (10)
C16—C15—C20	120.34 (18)	O4—S2—N2	106.51 (9)
C16—C15—S2	119.65 (14)	O3—S2—N2	106.90 (9)
C20—C15—S2	119.98 (14)	O4—S2—C15	108.02 (8)
C17—C16—C15	119.26 (19)	O3—S2—C15	107.73 (9)
C17—C16—H16	120.4	N2—S2—C15	107.22 (8)
C15—C16—H16	120.4	C7—N1—C21	115.15 (17)
C16—C17—C18	120.1 (2)	C7—N1—S1	116.09 (13)
C16—C17—H17	119.9	C21—N1—S1	116.36 (14)
C18—C17—H17	119.9	C14—N2—C23	115.60 (17)
C19—C18—C17	120.4 (2)	C14—N2—S2	117.71 (13)
C19—C18—H18	119.8	C23—N2—S2	117.68 (13)
C6—C1—C2—C3	0.1 (3)	C9—C8—S1—O2	−167.52 (19)
C6—C1—C2—C14	−178.75 (16)	C13—C8—S1—O2	15.1 (2)
C1—C2—C3—C4	0.2 (3)	C9—C8—S1—N1	77.6 (2)
C14—C2—C3—C4	179.06 (18)	C13—C8—S1—N1	−99.8 (2)
C2—C3—C4—C5	−0.2 (3)	C16—C15—S2—O4	162.80 (16)
C3—C4—C5—C6	−0.1 (3)	C20—C15—S2—O4	−19.20 (19)
C4—C5—C6—C1	0.5 (3)	C16—C15—S2—O3	31.99 (18)
C4—C5—C6—C7	−177.20 (18)	C20—C15—S2—O3	−150.01 (16)
C2—C1—C6—C5	−0.5 (3)	C16—C15—S2—N2	−82.76 (17)
C2—C1—C6—C7	177.22 (16)	C20—C15—S2—N2	95.24 (17)
C5—C6—C7—N1	−112.7 (2)	C6—C7—N1—C21	71.0 (2)
C1—C6—C7—N1	69.7 (2)	C6—C7—N1—S1	−148.14 (14)
C13—C8—C9—C10	1.8 (4)	C22B—C21—N1—C7	−98.2 (6)
S1—C8—C9—C10	−175.61 (19)	C22A—C21—N1—C7	−131.5 (4)
C8—C9—C10—C11	−1.3 (4)	C22B—C21—N1—S1	121.0 (6)
C9—C10—C11—C12	−0.2 (5)	C22A—C21—N1—S1	87.7 (4)
C10—C11—C12—C13	1.3 (5)	O1—S1—N1—C7	48.65 (16)
C11—C12—C13—C8	−0.8 (5)	O2—S1—N1—C7	177.65 (14)
C9—C8—C13—C12	−0.7 (4)	C8—S1—N1—C7	−66.87 (15)
S1—C8—C13—C12	176.7 (2)	O1—S1—N1—C21	−170.94 (15)
C3—C2—C14—N2	120.3 (2)	O2—S1—N1—C21	−41.94 (17)
C1—C2—C14—N2	−60.8 (2)	C8—S1—N1—C21	73.54 (16)
C20—C15—C16—C17	0.4 (3)	C2—C14—N2—C23	−69.5 (2)
S2—C15—C16—C17	178.43 (17)	C2—C14—N2—S2	144.01 (14)
C15—C16—C17—C18	−0.4 (3)	C24—C23—N2—C14	114.9 (2)
C16—C17—C18—C19	0.6 (4)	C24—C23—N2—S2	−98.7 (2)
C17—C18—C19—C20	−0.8 (4)	O4—S2—N2—C14	−173.57 (14)
C18—C19—C20—C15	0.8 (3)	O3—S2—N2—C14	−44.33 (16)
C16—C15—C20—C19	−0.6 (3)	C15—S2—N2—C14	70.98 (15)
S2—C15—C20—C19	−178.58 (17)	O4—S2—N2—C23	40.68 (17)
C9—C8—S1—O1	−37.4 (2)	O3—S2—N2—C23	169.93 (15)
C13—C8—S1—O1	145.2 (2)	C15—S2—N2—C23	−74.77 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O1i	0.93	2.57	3.409 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O1i	0.93	2.57	3.409 (3)	151

Symmetry code: (i) .