N,N′-Bis(3,3-dimethyl­all­yl)-N,N′-(prop­ane-1,3-diyl)dibenzene­sulfonamide

Khan, I.U.; Sheikh, T.A.; Ejaz; Harrison, W.T.A.

doi:10.1107/S1600536811050562

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3507

https://doi.org/10.1107/S1600536811050562

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N,N′-Bis(3,3-dimethylallyl)-N,N′-(propane-1,3-diyl)dibenzenesulfonamide

Islam Ullah Khan,^a ^* Tahir Ali Sheikh,^a Ejaz ^a and William T. A. Harrison ^b

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, and ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
^*Correspondence e-mail: iuklodhi@yahoo.com

(Received 1 November 2011; accepted 24 November 2011; online 30 November 2011)

In the title compound, C₂₅H₃₄N₂O₄S₂, 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_r = 490.66
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.102
S = 1.05
5059 reflections
302 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811050562/zs2161sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050562/zs2161Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811050562/zs2161Isup3.cml

checkCIF report

Comment top

As part of our ongoing structural studies of symmetric sulfonamides with a linking propyl chain, including N-[3-(benzenesulfonamido)propyl]benzenesulfonamide (II) (Sheikh et al., 2011) and N,N'-(propane-1,3-diyl)bis(p-toluenesulfonamide) (III) (Khan et al., 2011), the synthesis and structure of the title compound, C₂₅H₃₄N₂O₄S₂ (I), (Fig. 1), are now described.

The dihedral angle between the phenyl rings in the title compound (I) is 89.64 (6)°. The conformations of the atoms of the central chain are gauche-anti [torsion angles N1—C7—C8—C8 = -68.49 (19)° and C7—C8—C9—N2 = 167.95 (14)°]. The S1—N1—C7—C8 and S2—N2—C9—C8 torsion angles are 116.52 (14)° and -98.69 (16)°, respectively. The bond-angle sums for N1 and N2 are 349.5 and 356.0°, respectively, indicating a significantly greater departure from planarity for N1. In the crystal of (I), only van der Waals' forces are present.

In compound (II) (Sheikh et al., 2011), the conformation of the central N—C—C—C—N chain is gauche-gauche [torsion angles = 72.5 (5) and 65.7 (5)°]. In compound (III) (Khan et al., 2011), the complete molecule is generated by crystallographic twofold symmetry and the two N—C—C—C fragments have the same gauche conformation [torsion angle = 75.53 (14)°].

Related literature top

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 top

A mixture of N-[3-(benzenesulfonamido)propyl]benzenesulfonamide (0.177 g, 0.5 mmol), sodium hydride (0.24 g; 1.0 mmol) and N,N-dimethylformamide (10.0 ml) was stirred in a 100 ml round-bottom flask at room temperature for 30 minutes followed by the addition of 3,3-dimethylallyl bromide (0.116 ml; 1.0 mmol). The reaction mixture was stirred for six hours with reaction progress monitored by TLC. At the end of the reaction, the contents were poured over crushed ice. The precipitated product was isolated, washed and recrystallized from methanol to yield colorless blocks.

Structure description top

Computing details top

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).

Figures top

Fig. 1. The molecular conformation and atom mumbering scheme for (I) showing 50% probability displacement ellipsoids.

N,N'-Bis(3,3-dimethylallyl)-N,N'- (propane-1,3-diyl)dibenzenesulfonamide top

Crystal data top

C₂₅H₃₄N₂O₄S₂	F(000) = 1048
M_r = 490.66	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0458P)² + 0.7949P] where P = (F_o² + 2F_c²)/3
5059 reflections	(Δ/σ)_max = 0.001
302 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₅H₃₄N₂O₄S₂	V = 2571.71 (10) Å³
M_r = 490.66	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.3019 (2) Å	µ = 0.24 mm⁻¹
b = 16.3962 (4) Å	T = 296 K
c = 16.0500 (4) Å	0.50 × 0.25 × 0.20 mm
β = 108.449 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4011 reflections with I > 2σ(I)
40701 measured reflections	R_int = 0.028
5059 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.05	Δρ_max = 0.25 e Å⁻³
5059 reflections	Δρ_min = −0.24 e Å⁻³
302 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₅H₃₄N₂O₄S₂
M_r	490.66
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.3019 (2), 16.3962 (4), 16.0500 (4)
β (°)	108.449 (1)
V (Å³)	2571.71 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.50 × 0.25 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	40701, 5059, 4011
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.102, 1.05
No. of reflections	5059
No. of parameters	302
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.24

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Acknowledgements

IUK thanks the Higher Education Commission of Pakistan for its financial support under the project to strengthe the Materials Chemistry Laboratory at GCUL.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Khan, I. U., Sheikh, T. A., Ejaz, & Harrison, W. T. A. (2011). Acta Cryst. E67, o2371. Google Scholar
Sheikh, T. A., Khan, I. U., Harrison, W. T. A. & Ejaz, (2011). Acta Cryst. E67, o1737. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar