4-Methyl-N-[(E)-4-methyl-1-(4-methyl­phenyl­sulfon­yl)-1,2-dihydropyridin-2-yl­idene]benzene­sulfonamide

Tabatabaee, M.; Ghassemzadeh, M.; Hesami, L.; Neumüller, B.

doi:10.1107/S1600536810025158

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o1891

https://doi.org/10.1107/S1600536810025158

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4-Methyl-N-[(E)-4-methyl-1-(4-methylphenylsulfonyl)-1,2-dihydropyridin-2-ylidene]benzenesulfonamide

Masoumeh Tabatabaee,^a ^* Mitra Ghassemzadeh,^b Liela Hesami ^a and Bernhard Neumüller ^c

^aDepartment of Chemistry, Islamic Azad University, Yazd Branch, Yazd, Iran, ^bChemistry & Chemical Engineering Research Centre of Iran, Tehran, Iran, and ^cFachbereich Chemie, Universitat Marburg, Marburg, Germany
^*Correspondence e-mail: tabatabaee45m@yahoo.com

(Received 21 May 2010; accepted 26 June 2010; online 3 July 2010)

The reaction of 2-(aminomethyl)pyridine and 4-toluenesulfonyl chloride in CH₂Cl₂ at pH 8 led to the title compound, C₂₀H₂₀N₂O₄S₂. The aromatic rings are almost perpendicular to each other and the dihedral angles between the aromatic ring planes are 74.33 (9) (central pyridine versus benzene ring of the tosyl group bonded to the imine functionality), 73.77 (6) (pyridine versus benzene ring of the tosyl group bonded to pyridinic N atom) and 79.83 (9)° (benzene rings of tosyl groups). In the crystal structure, intermolecular aromatic π–π stacking interactions [centroid–centroid separation = 3.6274 (14) Å] help to consolidate the packing.

Related literature

For sulfonamide compounds, see: Maren (1967 ); Supuran et al. (1999 ); Culf et al. (1997 ); Kremer et al. (2006 ). For 2-amino-methylpyridine sulfonamide derivatives, see: Beloso et al. (2003 , 2004 , 2005 , 2006 ). For related N and S-containing compounds, see: Tabatabaee et al. (2006 , 2007 , 2008 , 2009 ).

Experimental

Crystal data

C₂₀H₂₀N₂O₄S₂
M_r = 416.50
Orthorhombic, P b c a
a = 14.888 (1) Å
b = 13.884 (1) Å
c = 18.843 (1) Å
V = 3894.9 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 100 K
0.21 × 0.12 × 0.08 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.78, T_max = 1.0
39760 measured reflections
3785 independent reflections
2634 reflections with I > 2σ(I)
R_int = 0.139

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.094
S = 0.94
3785 reflections
301 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810025158/bh2287sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025158/bh2287Isup2.hkl

checkCIF report

Comment top

The sulfonamides represent an important class of biologically active compounds (Supuran et al., 1999). There are several sulfonamide-based groups of drugs. Aromatic sulfonamides are strong inhibitors of carbonic anhydrase (Maren, 1967) and are of pharmacological value because of their effects on various physiological reactions ultimately involving bicarbonate. Some 10,000 structurally different sulfonamides have been synthesized as a result of the discovery of the antibacterial properties of sulfanilamide. The practice of synthesizing numerous structurally related compounds in an effort to find some that are more efficient or have fewer side effects than those already available is very important for the pharmaceutical industry. Moreover, sulfonamides containing different donor atoms find use in coordination chemistry. Recently, synthesis and crystal structure of several sulfonamide ligands with heterocyclic amines and their complexes have been reported (Culf et al., 1997; Kremer et al., 2006; Beloso et al., 2003, 2004, 2005, 2006). In continuation of our recent work on synthesis of new ligands with S and N donor atoms (Tabatabaee et al., 2006, 2007, 2008, 2009), in this paper we wish to report our results on the synthesis and crystal structure of a bisulfonamide compound, which resulted from 2-amino-4-methylpyridine and 4-toluenesulfonyl chloride. Reaction of one molecule of 4-toluenesulfonyl chloride with the NH₂ group of 2-amino-4-methylpyridine led to corresponding sulfonamide. The resulting sulfonamide shows imido-amido tautomerism. Imido-amido tautomerism has been reported for some sulfonamide compounds (Beloso et al., 2003, 2004, 2005). Reaction of another molecule of 4-toluenesulfonyl chloride with endocyclic NH group in imido form led to the title molecule.

In the molecule (Fig. 1), the bond lengths and angles are unexceptional. The molecule crystallizes in the orthorhombic system, space group Pbca. The basic six-membered ring skeletons are planar. A: C1/C2/C3/C4/C5/N2; B: C10···C15; C: C17···C22. The dihedral angles formed by the planes A and B, A and C, and B and C: are 74.33 (9), 73.77 (6), and 79.83 (9)%, respectively, indicating that aromatic rings are almost perpendicular to each other.

Figure 2 shows aromatic π–π stacking interactions between 6-membered rings with separation 3.6274 (14) for Cg1···Cg3 (Cg1: ring A, Cg3: ring C).

Related literature top

For sulfonamide compounds, see: Maren (1967); Supuran et al. (1999); Culf et al. (1997); Kremer et al. (2006). For 2-amino-methylpyridine sulfonamide derivatives, see: Beloso et al. (2003, 2004, 2005, 2006). For N and S-containing related compounds, see: Tabatabaee et al. (2006, 2007, 2008, 2009).

Experimental top

2-amino-4-picoline (5 mmol) was added to a solution of 4-toluenesulfonyl chloride (10 mmol) in CH₂Cl₂ (30 ml). The pH of the resulting mixture was adjusted to 8 with an aqueous solution of sodium carbonate. The reaction mixture was stirred at room temperature. The progress of the reaction was monitored by thin layer chromatography (TLC), using ethyl acetate and n-hexane in 2:1 ratio as eluent. After completion of the reaction (12 h), water and ethyl acetate (50 ml 1:1) was added and the organic layer was separated. The solvent was evaporated and the solid residue was filtered, washed with cold CH₂Cl₂ (10 ml) and recrystallized from CH₂Cl₂.

Structure description top

Figure 2 shows aromatic π–π stacking interactions between 6-membered rings with separation 3.6274 (14) for Cg1···Cg3 (Cg1: ring A, Cg3: ring C).

For sulfonamide compounds, see: Maren (1967); Supuran et al. (1999); Culf et al. (1997); Kremer et al. (2006). For 2-amino-methylpyridine sulfonamide derivatives, see: Beloso et al. (2003, 2004, 2005, 2006). For N and S-containing related compounds, see: Tabatabaee et al. (2006, 2007, 2008, 2009).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The general view of the title compound. Non-H atoms are represented with thermal ellipsoids (p = 50%).
	Fig. 2. Representation of π–π stacking in the crystal.

4-Methyl-N-[(E)-4-methyl-1-(4-methylphenylsulfonyl)-1,2- dihydropyridin-2-ylidene]benzenesulfonamide top

Crystal data top

C₂₀H₂₀N₂O₄S₂	F(000) = 1744
M_r = 416.50	D_x = 1.421 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 15000 reflections
a = 14.888 (1) Å	θ = 2.2–25.9°
b = 13.884 (1) Å	µ = 0.30 mm⁻¹
c = 18.843 (1) Å	T = 100 K
V = 3894.9 (4) Å³	Blocks, colorless
Z = 8	0.21 × 0.12 × 0.08 mm

Data collection top

Stoe IPDS-2 diffractometer	3785 independent reflections
Radiation source: fine-focus sealed tube	2634 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.139
ω scans	θ_max = 25.9°, θ_min = 2.2°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −18→16
T_min = 0.78, T_max = 1.0	k = −17→17
39760 measured reflections	l = −23→23

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ²(F_o²) + (0.0461P)²] where P = (F_o² + 2F_c²)/3
3785 reflections	(Δ/σ)_max = 0.006
301 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³
0 constraints

Crystal data top

C₂₀H₂₀N₂O₄S₂	V = 3894.9 (4) Å³
M_r = 416.50	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.888 (1) Å	µ = 0.30 mm⁻¹
b = 13.884 (1) Å	T = 100 K
c = 18.843 (1) Å	0.21 × 0.12 × 0.08 mm

Data collection top

Stoe IPDS-2 diffractometer	3785 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2634 reflections with I > 2σ(I)
T_min = 0.78, T_max = 1.0	R_int = 0.139
39760 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	Δρ_max = 0.26 e Å⁻³
3785 reflections	Δρ_min = −0.28 e Å⁻³
301 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.05540 (13)	0.20334 (16)	0.60238 (10)	0.0345 (5)
C1	0.02054 (16)	0.17947 (17)	0.54034 (12)	0.0320 (5)
C2	−0.05445 (18)	0.12038 (19)	0.52422 (13)	0.0350 (6)
H21	−0.0872 (18)	0.094 (2)	0.5645 (14)	0.043 (8)*
C3	−0.07778 (16)	0.09601 (18)	0.45642 (13)	0.0363 (6)
C4	−0.02553 (18)	0.1336 (2)	0.40005 (14)	0.0404 (6)
H41	−0.0383 (19)	0.118 (2)	0.3541 (14)	0.047 (8)*
C5	0.04321 (18)	0.1926 (2)	0.41261 (13)	0.0380 (6)
H51	0.0800 (18)	0.224 (2)	0.3798 (14)	0.043 (8)*
N2	0.06665 (13)	0.21788 (15)	0.48155 (10)	0.0322 (5)
C6	−0.15554 (18)	0.0317 (2)	0.44075 (15)	0.0458 (7)
H61	−0.1993	0.0663	0.4115	0.074 (3)*
H62	−0.1840	0.0119	0.4853	0.074 (3)*
H63	−0.1344	−0.0255	0.4152	0.074 (3)*
S1	0.01200 (4)	0.17417 (5)	0.67754 (3)	0.03399 (16)
O1	−0.02748 (12)	0.07934 (12)	0.67874 (9)	0.0400 (4)
O2	0.08054 (11)	0.19323 (14)	0.72943 (8)	0.0437 (5)
C10	−0.07471 (16)	0.25859 (18)	0.69174 (11)	0.0311 (5)
C11	−0.05235 (19)	0.3552 (2)	0.70311 (12)	0.0378 (6)
H111	0.0090 (19)	0.375 (2)	0.7026 (13)	0.045 (8)*
C12	−0.1196 (2)	0.4205 (2)	0.71944 (14)	0.0423 (6)
H121	−0.1048 (18)	0.484 (2)	0.7293 (14)	0.045 (8)*
C13	−0.20904 (18)	0.3922 (2)	0.72532 (12)	0.0388 (6)
C14	−0.22968 (17)	0.2957 (2)	0.71211 (12)	0.0350 (6)
H141	−0.2888 (16)	0.2719 (17)	0.7150 (11)	0.026 (6)*
C15	−0.16385 (17)	0.22994 (19)	0.69476 (11)	0.0313 (5)
H151	−0.1737 (16)	0.1651 (19)	0.6852 (12)	0.031 (6)*
C16	−0.2808 (2)	0.4625 (2)	0.74675 (16)	0.0559 (8)
H161	−0.3267	0.4656	0.7096	0.074 (3)*
H162	−0.2541	0.5263	0.7534	0.074 (3)*
H163	−0.3084	0.4412	0.7913	0.074 (3)*
S2	0.15670 (4)	0.29710 (5)	0.49328 (3)	0.03332 (16)
O3	0.12874 (12)	0.36943 (12)	0.54198 (9)	0.0383 (4)
O4	0.17995 (12)	0.32336 (13)	0.42217 (8)	0.0397 (4)
C17	0.24203 (16)	0.22493 (17)	0.52834 (11)	0.0300 (5)
C18	0.29660 (16)	0.17449 (18)	0.48104 (12)	0.0333 (6)
H181	0.2828 (16)	0.1738 (18)	0.4335 (13)	0.035 (7)*
C19	0.36808 (17)	0.12187 (18)	0.50725 (13)	0.0345 (6)
H191	0.405 (2)	0.088 (2)	0.4766 (14)	0.049 (8)*
C20	0.38645 (17)	0.11905 (17)	0.57977 (12)	0.0316 (5)
C21	0.33018 (16)	0.17011 (19)	0.62528 (12)	0.0336 (5)
H211	0.3456 (18)	0.173 (2)	0.6730 (15)	0.046 (7)*
C22	0.25832 (17)	0.22302 (19)	0.60086 (12)	0.0334 (6)
H221	0.2183 (18)	0.259 (2)	0.6317 (14)	0.043 (7)*
C23	0.46446 (17)	0.0628 (2)	0.60856 (13)	0.0384 (6)
H231	0.5158	0.0691	0.5764	0.074 (3)*
H232	0.4477	−0.0053	0.6126	0.074 (3)*
H233	0.4807	0.0877	0.6555	0.074 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0301 (10)	0.0417 (12)	0.0318 (10)	−0.0014 (10)	0.0027 (8)	−0.0025 (9)
C1	0.0284 (12)	0.0321 (13)	0.0356 (12)	0.0052 (11)	0.0012 (10)	−0.0011 (10)
C2	0.0329 (13)	0.0338 (14)	0.0384 (13)	0.0031 (11)	0.0002 (11)	0.0002 (11)
C3	0.0323 (13)	0.0329 (14)	0.0437 (13)	0.0061 (11)	−0.0053 (11)	−0.0057 (11)
C4	0.0411 (15)	0.0447 (16)	0.0353 (14)	0.0059 (13)	−0.0082 (12)	−0.0085 (12)
C5	0.0384 (14)	0.0430 (16)	0.0326 (13)	0.0047 (13)	0.0020 (11)	−0.0025 (12)
N2	0.0314 (10)	0.0358 (12)	0.0294 (10)	−0.0007 (9)	0.0006 (8)	−0.0034 (8)
C6	0.0406 (15)	0.0410 (16)	0.0558 (16)	0.0016 (13)	−0.0085 (13)	−0.0077 (12)
S1	0.0302 (3)	0.0412 (4)	0.0305 (3)	0.0009 (3)	0.0005 (2)	0.0024 (3)
O1	0.0422 (10)	0.0346 (10)	0.0432 (9)	0.0007 (8)	0.0044 (8)	0.0043 (8)
O2	0.0350 (9)	0.0611 (13)	0.0352 (9)	0.0020 (9)	−0.0040 (7)	0.0040 (8)
C10	0.0358 (13)	0.0365 (14)	0.0208 (11)	−0.0008 (11)	0.0012 (9)	0.0022 (10)
C11	0.0359 (14)	0.0424 (16)	0.0351 (13)	−0.0063 (13)	0.0019 (11)	0.0016 (11)
C12	0.0512 (17)	0.0374 (16)	0.0385 (14)	−0.0017 (14)	0.0019 (12)	0.0003 (12)
C13	0.0440 (15)	0.0449 (17)	0.0274 (11)	0.0086 (13)	0.0011 (11)	0.0028 (11)
C14	0.0322 (13)	0.0482 (16)	0.0246 (11)	0.0000 (12)	0.0016 (9)	0.0058 (11)
C15	0.0329 (13)	0.0378 (15)	0.0232 (11)	−0.0031 (11)	−0.0014 (9)	0.0027 (10)
C16	0.0565 (19)	0.054 (2)	0.0571 (17)	0.0186 (16)	0.0006 (14)	−0.0007 (15)
S2	0.0315 (3)	0.0334 (3)	0.0350 (3)	0.0006 (3)	0.0029 (2)	0.0004 (3)
O3	0.0372 (10)	0.0310 (10)	0.0465 (10)	0.0024 (8)	0.0042 (8)	−0.0071 (8)
O4	0.0376 (10)	0.0441 (11)	0.0374 (9)	0.0026 (8)	0.0052 (7)	0.0088 (8)
C17	0.0292 (12)	0.0297 (13)	0.0311 (12)	−0.0023 (10)	0.0014 (9)	0.0005 (9)
C18	0.0338 (13)	0.0396 (15)	0.0264 (12)	0.0009 (11)	0.0032 (10)	0.0005 (10)
C19	0.0375 (14)	0.0353 (14)	0.0308 (12)	0.0042 (11)	0.0038 (11)	−0.0011 (11)
C20	0.0316 (13)	0.0293 (14)	0.0339 (12)	−0.0029 (11)	0.0008 (10)	0.0001 (10)
C21	0.0318 (13)	0.0415 (15)	0.0277 (11)	−0.0034 (11)	−0.0007 (10)	−0.0012 (10)
C22	0.0317 (13)	0.0377 (15)	0.0310 (12)	−0.0028 (11)	0.0046 (10)	−0.0065 (11)
C23	0.0371 (14)	0.0396 (15)	0.0384 (13)	−0.0002 (12)	−0.0057 (11)	−0.0002 (11)

Geometric parameters (Å, º) top

N1—C1	1.321 (3)	C13—C14	1.397 (4)
N1—S1	1.609 (2)	C13—C16	1.502 (4)
C1—N2	1.408 (3)	C14—C15	1.379 (4)
C1—C2	1.418 (4)	C14—H141	0.94 (2)
C2—C3	1.367 (3)	C15—H151	0.93 (3)
C2—H21	0.98 (3)	C16—H161	0.9800
C3—C4	1.416 (4)	C16—H162	0.9800
C3—C6	1.492 (4)	C16—H163	0.9800
C4—C5	1.333 (4)	S2—O3	1.4225 (17)
C4—H41	0.91 (3)	S2—O4	1.4310 (17)
C5—N2	1.390 (3)	S2—C17	1.748 (2)
C5—H51	0.93 (3)	C17—C22	1.388 (3)
N2—S2	1.748 (2)	C17—C18	1.395 (3)
C6—H61	0.9800	C18—C19	1.382 (3)
C6—H62	0.9800	C18—H181	0.92 (2)
C6—H63	0.9800	C19—C20	1.394 (3)
S1—O2	1.4378 (18)	C19—H191	0.93 (3)
S1—O1	1.4421 (19)	C20—C21	1.393 (3)
S1—C10	1.764 (3)	C20—C23	1.501 (3)
C10—C15	1.387 (3)	C21—C22	1.377 (4)
C10—C11	1.398 (4)	C21—H211	0.93 (3)
C11—C12	1.385 (4)	C22—H221	0.97 (3)
C11—H111	0.96 (3)	C23—H231	0.9800
C12—C13	1.392 (4)	C23—H232	0.9800
C12—H121	0.93 (3)	C23—H233	0.9800

C1—N1—S1	123.92 (18)	C15—C14—C13	121.4 (2)
N1—C1—N2	114.2 (2)	C15—C14—H141	116.4 (15)
N1—C1—C2	130.1 (2)	C13—C14—H141	122.2 (14)
N2—C1—C2	115.7 (2)	C14—C15—C10	120.0 (2)
C3—C2—C1	122.9 (2)	C14—C15—H151	125.1 (16)
C3—C2—H21	120.4 (16)	C10—C15—H151	114.9 (15)
C1—C2—H21	116.6 (15)	C13—C16—H161	109.5
C2—C3—C4	118.1 (2)	C13—C16—H162	109.5
C2—C3—C6	122.0 (2)	H161—C16—H162	109.5
C4—C3—C6	119.9 (2)	C13—C16—H163	109.5
C5—C4—C3	121.0 (2)	H161—C16—H163	109.5
C5—C4—H41	118.5 (18)	H162—C16—H163	109.5
C3—C4—H41	120.5 (18)	O3—S2—O4	119.67 (11)
C4—C5—N2	120.9 (2)	O3—S2—C17	111.94 (11)
C4—C5—H51	128.4 (16)	O4—S2—C17	108.91 (11)
N2—C5—H51	110.7 (17)	O3—S2—N2	107.53 (10)
C5—N2—C1	121.2 (2)	O4—S2—N2	103.14 (10)
C5—N2—S2	117.98 (17)	C17—S2—N2	104.15 (11)
C1—N2—S2	120.84 (15)	C22—C17—C18	121.2 (2)
C3—C6—H61	109.5	C22—C17—S2	120.67 (18)
C3—C6—H62	109.5	C18—C17—S2	118.02 (17)
H61—C6—H62	109.5	C19—C18—C17	119.1 (2)
C3—C6—H63	109.5	C19—C18—H181	121.0 (16)
H61—C6—H63	109.5	C17—C18—H181	119.8 (16)
H62—C6—H63	109.5	C18—C19—C20	121.1 (2)
O2—S1—O1	116.53 (11)	C18—C19—H191	120.5 (17)
O2—S1—N1	105.50 (11)	C20—C19—H191	118.4 (17)
O1—S1—N1	114.05 (11)	C21—C20—C19	118.1 (2)
O2—S1—C10	107.09 (11)	C21—C20—C23	120.5 (2)
O1—S1—C10	107.82 (11)	C19—C20—C23	121.4 (2)
N1—S1—C10	105.09 (11)	C22—C21—C20	122.2 (2)
C15—C10—C11	119.8 (2)	C22—C21—H211	119.6 (17)
C15—C10—S1	121.1 (2)	C20—C21—H211	117.9 (17)
C11—C10—S1	119.09 (19)	C21—C22—C17	118.4 (2)
C12—C11—C10	119.3 (3)	C21—C22—H221	123.4 (15)
C12—C11—H111	120.0 (17)	C17—C22—H221	118.3 (15)
C10—C11—H111	120.5 (17)	C20—C23—H231	109.5
C11—C12—C13	121.7 (3)	C20—C23—H232	109.5
C11—C12—H121	119.6 (17)	H231—C23—H232	109.5
C13—C12—H121	118.7 (17)	C20—C23—H233	109.5
C12—C13—C14	117.8 (2)	H231—C23—H233	109.5
C12—C13—C16	121.2 (3)	H232—C23—H233	109.5
C14—C13—C16	121.0 (3)

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀N₂O₄S₂
M_r	416.50
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	14.888 (1), 13.884 (1), 18.843 (1)
V (Å³)	3894.9 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.21 × 0.12 × 0.08

Data collection
Diffractometer	Stoe IPDS2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.78, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	39760, 3785, 2634
R_int	0.139
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.094, 0.94
No. of reflections	3785
No. of parameters	301
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.28

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008), WinGX (Farrugia, 1999).

Acknowledgements

The authors are grateful to the Islamic Azad University, Yazd Branch, for support of this work.

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