N,N′-Diisopropyl-3,6-dimethoxy­naphthalene-2,7-disulfonamide

Song, Z.-W.; Hu, Z.-Q.

doi:10.1107/S1600536808021211

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1499

doi:10.1107/S1600536808021211

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N,N′-Diisopropyl-3,6-dimethoxynaphthalene-2,7-disulfonamide

Zu-Wei Song ^a and Zhi-Qiang Hu ^b ^*

^aCollege of Science, Qingdao Agricultural University, Qingdao 266109, People's Republic of China, and ^bCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
^*Correspondence e-mail: songzuwei2008@yahoo.cn

(Received 6 July 2008; accepted 8 July 2008; online 16 July 2008)

In the title compound, C₁₈H₂₆N₂O₆S₂, all bond lengths and angles are normal. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds.

Related literature

For the crystal structures of related compounds, see: Henschel et al. (1996 ). For details of the biological activities of fluorine-containing compounds, see: Kamoshita et al. (1987 ). For catalytic activity, see: Zhang et al. (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₈H₂₆N₂O₆S₂
M_r = 430.53
Monoclinic, P 2₁ /c
a = 17.229 (3) Å
b = 7.2532 (15) Å
c = 18.035 (4) Å
β = 108.35 (3)°
V = 2139.2 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 173 (2) K
0.50 × 0.38 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.871, T_max = 0.940
8740 measured reflections
4889 independent reflections
4227 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.117
S = 1.16
4889 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.88	2.00	2.821 (2)	154
N2—H2B⋯O5ⁱⁱ	0.88	2.22	3.001 (2)	148
N2—H2B⋯O6ⁱⁱ	0.88	2.53	3.235 (2)	138
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+2, -z+1.

Data collection: RAPID-AUTO (Rigaku, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021211/hg2423sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021211/hg2423Isup2.hkl

checkCIF report

Comment top

The sulfonamides form an important group in organic chemistry with many compounds containing sulfonamide groups possessing a broad spectrum of biological activities and can be widely used as herbicides (Kamoshita et al., 1987). In addition, some compounds containing sulfonimide groups can be used as catalysts (Zhang et al., 2007). Here, we report the crystal structure of the title compound, (I).

In (I) (Fig. 1), all bond lengths are normal (Allen et al., 1987) and in good agreement with those reported previously (Henschel et al., 1996). As can be seen from the packing diagram (Fig. 2), the crystal structure of (I) is stabilized by intermolecular N—H···O hydrogen bonding. The crystal packing is further stabilized by van der Waals forces

Related literature top

For the crystal structures of related compounds, see: Henschel et al. (1996). For details of the biological activities of fluorine-containing compounds, see: Kamoshita et al. (1987). For catalytic activity, see: Zhang et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

A solution of naphthalene disulfonyl chloride (384 mg, 1 mmol) dissolved in anhydrous CH₂Cl₂ (10 ml), and dropwise added over a period of 10 min to a solution of propan-2-amine (118 mg, 2 mmol) in CH₂Cl₂ (10 ml) at 273 K. The mixture was stirred at r.t. for 4 h. The organic phase was washed with water twice, and dried over anhydrous Na₂SO₄. The solvent was removed and the residue was purified by flash chromatography (1:3 cyclohexane:dichloromethane) to give ) as a white solid (267 mg, 62%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol and dichloromethane at room temperature.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 40% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down the a axis, showing one layer of molecules connected by N—H···O hydrogen bonds (dashed lines).

N,N'-Diisopropyl-3,6-dimethoxynaphthalene-2,7-disulfonamide top

Crystal data top

C₁₈H₂₆N₂O₆S₂	F(000) = 912
M_r = 430.53	D_x = 1.337 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 875 reflections
a = 17.229 (3) Å	θ = 2.2–27.5°
b = 7.2532 (15) Å	µ = 0.28 mm⁻¹
c = 18.035 (4) Å	T = 173 K
β = 108.35 (3)°	Plate, colorless
V = 2139.2 (8) Å³	0.50 × 0.38 × 0.22 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	4889 independent reflections
Radiation source: rotating anode	4227 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans at fixed χ = 45°	θ_max = 27.5°, θ_min = 1.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −22→22
T_min = 0.871, T_max = 0.940	k = −9→9
8740 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.0534P)² + 0.9298P] where P = (F_o² + 2F_c²)/3
4889 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₈H₂₆N₂O₆S₂	V = 2139.2 (8) Å³
M_r = 430.53	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.229 (3) Å	µ = 0.28 mm⁻¹
b = 7.2532 (15) Å	T = 173 K
c = 18.035 (4) Å	0.50 × 0.38 × 0.22 mm
β = 108.35 (3)°

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	4889 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4227 reflections with I > 2σ(I)
T_min = 0.871, T_max = 0.940	R_int = 0.020
8740 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.16	Δρ_max = 0.36 e Å⁻³
4889 reflections	Δρ_min = −0.49 e Å⁻³
253 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
S1	0.39879 (3)	0.72730 (7)	0.23076 (3)	0.02292 (13)
S2	0.08210 (3)	1.11117 (7)	0.42543 (3)	0.01969 (13)
O1	0.42832 (10)	0.4396 (2)	0.35142 (10)	0.0368 (4)
O2	0.48381 (9)	0.7597 (2)	0.27099 (10)	0.0365 (4)
O3	0.35149 (10)	0.8610 (2)	0.17682 (9)	0.0325 (4)
O4	0.08620 (9)	1.2491 (2)	0.36997 (9)	0.0277 (3)
O5	0.09471 (9)	1.1659 (2)	0.50512 (8)	0.0261 (3)
O6	0.12159 (9)	0.7784 (2)	0.52066 (8)	0.0268 (3)
N1	0.39535 (10)	0.5367 (2)	0.18585 (10)	0.0232 (4)
H1A	0.4415	0.4763	0.1933	0.028*
N2	−0.00546 (10)	1.0136 (2)	0.39554 (9)	0.0223 (4)
H2B	−0.0358	1.0076	0.4266	0.027*
C1	0.33009 (13)	0.5414 (3)	0.41377 (13)	0.0280 (5)
H1B	0.3424	0.4413	0.4496	0.034*
C2	0.37011 (13)	0.5567 (3)	0.35894 (13)	0.0262 (4)
C3	0.35006 (12)	0.7046 (3)	0.30358 (11)	0.0212 (4)
C4	0.29442 (12)	0.8349 (3)	0.30760 (11)	0.0209 (4)
H4B	0.2823	0.9338	0.2712	0.025*
C5	0.25444 (11)	0.8252 (3)	0.36502 (11)	0.0197 (4)
C6	0.19712 (11)	0.9599 (3)	0.37008 (11)	0.0197 (4)
H6A	0.1874	1.0640	0.3365	0.024*
C7	0.15537 (11)	0.9418 (3)	0.42305 (11)	0.0190 (4)
C8	0.16906 (12)	0.7855 (3)	0.47337 (11)	0.0215 (4)
C9	0.22660 (13)	0.6566 (3)	0.47142 (12)	0.0247 (4)
H9A	0.2370	0.5553	0.5066	0.030*
C10	0.27065 (12)	0.6734 (3)	0.41739 (11)	0.0222 (4)
C11	0.4475 (2)	0.2809 (4)	0.40126 (18)	0.0543 (8)
H11A	0.4905	0.2093	0.3897	0.081*
H11B	0.3985	0.2044	0.3922	0.081*
H11C	0.4666	0.3207	0.4560	0.081*
C12	0.32048 (14)	0.4553 (3)	0.13290 (14)	0.0336 (5)
H12A	0.2781	0.5540	0.1156	0.040*
C13	0.28821 (17)	0.3054 (4)	0.1736 (2)	0.0527 (8)
H13A	0.2766	0.3573	0.2191	0.079*
H13B	0.3292	0.2075	0.1905	0.079*
H13C	0.2379	0.2541	0.1374	0.079*
C14	0.3397 (2)	0.3816 (5)	0.06177 (16)	0.0605 (9)
H14A	0.3603	0.4820	0.0368	0.091*
H14B	0.2899	0.3305	0.0246	0.091*
H14C	0.3813	0.2847	0.0780	0.091*
C15	0.12852 (15)	0.6187 (3)	0.56924 (14)	0.0333 (5)
H15A	0.0910	0.6304	0.6001	0.050*
H15B	0.1848	0.6082	0.6044	0.050*
H15C	0.1145	0.5083	0.5364	0.050*
C16	−0.03619 (12)	0.9332 (3)	0.31603 (11)	0.0237 (4)
H16A	0.0085	0.9406	0.2917	0.028*
C17	−0.10837 (15)	1.0449 (4)	0.26648 (13)	0.0365 (6)
H17A	−0.0915	1.1732	0.2642	0.055*
H17B	−0.1527	1.0400	0.2897	0.055*
H17C	−0.1276	0.9935	0.2135	0.055*
C18	−0.05611 (15)	0.7314 (3)	0.32295 (13)	0.0315 (5)
H18A	−0.0071	0.6671	0.3553	0.047*
H18B	−0.0746	0.6756	0.2708	0.047*
H18C	−0.0995	0.7212	0.3472	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0250 (3)	0.0202 (3)	0.0293 (3)	−0.00251 (19)	0.0167 (2)	−0.0004 (2)
S2	0.0251 (3)	0.0173 (2)	0.0197 (2)	0.00184 (18)	0.01134 (18)	−0.00043 (19)
O1	0.0400 (9)	0.0387 (10)	0.0408 (9)	0.0213 (8)	0.0256 (8)	0.0147 (8)
O2	0.0269 (8)	0.0371 (10)	0.0497 (10)	−0.0128 (7)	0.0179 (7)	−0.0073 (8)
O3	0.0468 (10)	0.0232 (8)	0.0372 (9)	0.0067 (7)	0.0270 (8)	0.0073 (7)
O4	0.0373 (8)	0.0209 (8)	0.0307 (8)	0.0051 (6)	0.0192 (7)	0.0061 (6)
O5	0.0350 (8)	0.0238 (8)	0.0229 (7)	−0.0010 (6)	0.0143 (6)	−0.0054 (6)
O6	0.0377 (9)	0.0218 (8)	0.0297 (8)	0.0051 (6)	0.0232 (7)	0.0056 (6)
N1	0.0204 (8)	0.0233 (9)	0.0278 (9)	0.0050 (7)	0.0100 (7)	−0.0020 (7)
N2	0.0211 (8)	0.0296 (10)	0.0197 (8)	0.0004 (7)	0.0114 (7)	−0.0028 (7)
C1	0.0325 (12)	0.0280 (12)	0.0270 (10)	0.0091 (9)	0.0144 (9)	0.0078 (9)
C2	0.0250 (10)	0.0278 (11)	0.0284 (10)	0.0074 (8)	0.0120 (8)	0.0032 (9)
C3	0.0222 (10)	0.0210 (10)	0.0223 (9)	−0.0023 (8)	0.0099 (8)	−0.0008 (8)
C4	0.0227 (10)	0.0199 (10)	0.0210 (9)	−0.0019 (8)	0.0084 (8)	−0.0012 (8)
C5	0.0197 (9)	0.0207 (10)	0.0191 (9)	−0.0006 (7)	0.0069 (7)	−0.0003 (8)
C6	0.0218 (10)	0.0195 (10)	0.0187 (9)	−0.0003 (7)	0.0076 (7)	0.0015 (8)
C7	0.0208 (9)	0.0173 (9)	0.0193 (9)	0.0009 (7)	0.0070 (7)	−0.0012 (7)
C8	0.0256 (10)	0.0227 (10)	0.0189 (9)	−0.0004 (8)	0.0108 (8)	−0.0001 (8)
C9	0.0302 (11)	0.0229 (11)	0.0239 (10)	0.0047 (8)	0.0126 (9)	0.0048 (8)
C10	0.0233 (10)	0.0232 (10)	0.0211 (9)	0.0012 (8)	0.0085 (8)	−0.0003 (8)
C11	0.0676 (19)	0.0501 (17)	0.0593 (17)	0.0394 (15)	0.0400 (15)	0.0280 (14)
C12	0.0292 (12)	0.0283 (12)	0.0356 (12)	0.0092 (9)	−0.0008 (9)	−0.0077 (10)
C13	0.0341 (14)	0.0359 (15)	0.085 (2)	−0.0089 (11)	0.0150 (14)	−0.0131 (15)
C14	0.066 (2)	0.068 (2)	0.0356 (14)	0.0236 (17)	0.0000 (14)	−0.0182 (15)
C15	0.0495 (14)	0.0233 (11)	0.0372 (12)	0.0038 (10)	0.0281 (11)	0.0065 (10)
C16	0.0251 (10)	0.0297 (11)	0.0182 (9)	0.0022 (8)	0.0097 (8)	−0.0024 (8)
C17	0.0359 (13)	0.0399 (14)	0.0288 (11)	0.0101 (10)	0.0031 (10)	0.0007 (10)
C18	0.0407 (13)	0.0282 (12)	0.0264 (11)	−0.0013 (10)	0.0119 (10)	−0.0041 (9)

Geometric parameters (Å, º) top

S1—O3	1.4324 (16)	C8—C9	1.371 (3)
S1—O2	1.4345 (17)	C9—C10	1.416 (3)
S1—N1	1.5937 (18)	C9—H9A	0.9500
S1—C3	1.775 (2)	C11—H11A	0.9800
S2—O4	1.4320 (15)	C11—H11B	0.9800
S2—O5	1.4402 (15)	C11—H11C	0.9800
S2—N2	1.5984 (18)	C12—C13	1.512 (4)
S2—C7	1.772 (2)	C12—C14	1.520 (4)
O1—C2	1.353 (2)	C12—H12A	1.0000
O1—C11	1.434 (3)	C13—H13A	0.9800
O6—C8	1.356 (2)	C13—H13B	0.9800
O6—C15	1.434 (3)	C13—H13C	0.9800
N1—C12	1.466 (3)	C14—H14A	0.9800
N1—H1A	0.8800	C14—H14B	0.9800
N2—C16	1.483 (2)	C14—H14C	0.9800
N2—H2B	0.8800	C15—H15A	0.9800
C1—C2	1.377 (3)	C15—H15B	0.9800
C1—C10	1.418 (3)	C15—H15C	0.9800
C1—H1B	0.9500	C16—C17	1.517 (3)
C2—C3	1.432 (3)	C16—C18	1.517 (3)
C3—C4	1.364 (3)	C16—H16A	1.0000
C4—C5	1.415 (3)	C17—H17A	0.9800
C4—H4B	0.9500	C17—H17B	0.9800
C5—C6	1.412 (3)	C17—H17C	0.9800
C5—C10	1.420 (3)	C18—H18A	0.9800
C6—C7	1.371 (3)	C18—H18B	0.9800
C6—H6A	0.9500	C18—H18C	0.9800
C7—C8	1.424 (3)

O3—S1—O2	120.31 (10)	C1—C10—C5	119.10 (18)
O3—S1—N1	108.65 (10)	O1—C11—H11A	109.5
O2—S1—N1	105.52 (10)	O1—C11—H11B	109.5
O3—S1—C3	105.36 (9)	H11A—C11—H11B	109.5
O2—S1—C3	106.66 (10)	O1—C11—H11C	109.5
N1—S1—C3	110.17 (9)	H11A—C11—H11C	109.5
O4—S2—O5	118.63 (9)	H11B—C11—H11C	109.5
O4—S2—N2	108.82 (10)	N1—C12—C13	110.9 (2)
O5—S2—N2	106.76 (9)	N1—C12—C14	108.1 (2)
O4—S2—C7	105.99 (9)	C13—C12—C14	111.5 (2)
O5—S2—C7	109.31 (9)	N1—C12—H12A	108.8
N2—S2—C7	106.79 (9)	C13—C12—H12A	108.8
C2—O1—C11	118.22 (18)	C14—C12—H12A	108.8
C8—O6—C15	117.67 (16)	C12—C13—H13A	109.5
C12—N1—S1	124.38 (14)	C12—C13—H13B	109.5
C12—N1—H1A	117.8	H13A—C13—H13B	109.5
S1—N1—H1A	117.8	C12—C13—H13C	109.5
C16—N2—S2	120.79 (13)	H13A—C13—H13C	109.5
C16—N2—H2B	119.6	H13B—C13—H13C	109.5
S2—N2—H2B	119.6	C12—C14—H14A	109.5
C2—C1—C10	120.7 (2)	C12—C14—H14B	109.5
C2—C1—H1B	119.6	H14A—C14—H14B	109.5
C10—C1—H1B	119.6	C12—C14—H14C	109.5
O1—C2—C1	125.2 (2)	H14A—C14—H14C	109.5
O1—C2—C3	115.08 (18)	H14B—C14—H14C	109.5
C1—C2—C3	119.73 (19)	O6—C15—H15A	109.5
C4—C3—C2	120.08 (18)	O6—C15—H15B	109.5
C4—C3—S1	118.62 (15)	H15A—C15—H15B	109.5
C2—C3—S1	121.27 (15)	O6—C15—H15C	109.5
C3—C4—C5	121.11 (19)	H15A—C15—H15C	109.5
C3—C4—H4B	119.4	H15B—C15—H15C	109.5
C5—C4—H4B	119.4	N2—C16—C17	109.64 (17)
C6—C5—C4	121.62 (18)	N2—C16—C18	108.73 (17)
C6—C5—C10	119.25 (17)	C17—C16—C18	113.51 (19)
C4—C5—C10	119.10 (18)	N2—C16—H16A	108.3
C7—C6—C5	120.63 (18)	C17—C16—H16A	108.3
C7—C6—H6A	119.7	C18—C16—H16A	108.3
C5—C6—H6A	119.7	C16—C17—H17A	109.5
C6—C7—C8	120.15 (18)	C16—C17—H17B	109.5
C6—C7—S2	118.97 (15)	H17A—C17—H17B	109.5
C8—C7—S2	120.84 (14)	C16—C17—H17C	109.5
O6—C8—C9	125.04 (18)	H17A—C17—H17C	109.5
O6—C8—C7	114.81 (17)	H17B—C17—H17C	109.5
C9—C8—C7	120.14 (18)	C16—C18—H18A	109.5
C8—C9—C10	120.50 (19)	C16—C18—H18B	109.5
C8—C9—H9A	119.8	H18A—C18—H18B	109.5
C10—C9—H9A	119.8	C16—C18—H18C	109.5
C9—C10—C1	121.66 (19)	H18A—C18—H18C	109.5
C9—C10—C5	119.23 (18)	H18B—C18—H18C	109.5

O3—S1—N1—C12	−45.7 (2)	C5—C6—C7—S2	−178.34 (15)
O2—S1—N1—C12	−175.98 (18)	O4—S2—C7—C6	−3.88 (19)
C3—S1—N1—C12	69.3 (2)	O5—S2—C7—C6	−132.83 (16)
O4—S2—N2—C16	53.43 (18)	N2—S2—C7—C6	112.02 (16)
O5—S2—N2—C16	−177.42 (15)	O4—S2—C7—C8	178.22 (16)
C7—S2—N2—C16	−60.57 (18)	O5—S2—C7—C8	49.27 (18)
C11—O1—C2—C1	3.5 (4)	N2—S2—C7—C8	−65.88 (18)
C11—O1—C2—C3	−175.7 (2)	C15—O6—C8—C9	−3.8 (3)
C10—C1—C2—O1	179.1 (2)	C15—O6—C8—C7	176.08 (18)
C10—C1—C2—C3	−1.7 (3)	C6—C7—C8—O6	−177.07 (18)
O1—C2—C3—C4	−177.49 (19)	S2—C7—C8—O6	0.8 (2)
C1—C2—C3—C4	3.2 (3)	C6—C7—C8—C9	2.8 (3)
O1—C2—C3—S1	0.4 (3)	S2—C7—C8—C9	−179.31 (16)
C1—C2—C3—S1	−178.88 (18)	O6—C8—C9—C10	177.37 (19)
O3—S1—C3—C4	−14.70 (19)	C7—C8—C9—C10	−2.5 (3)
O2—S1—C3—C4	114.23 (17)	C8—C9—C10—C1	−179.6 (2)
N1—S1—C3—C4	−131.72 (16)	C8—C9—C10—C5	−0.1 (3)
O3—S1—C3—C2	167.35 (17)	C2—C1—C10—C9	177.6 (2)
O2—S1—C3—C2	−63.72 (19)	C2—C1—C10—C5	−1.8 (3)
N1—S1—C3—C2	50.3 (2)	C6—C5—C10—C9	2.5 (3)
C2—C3—C4—C5	−1.2 (3)	C4—C5—C10—C9	−175.71 (19)
S1—C3—C4—C5	−179.20 (15)	C6—C5—C10—C1	−178.05 (19)
C3—C4—C5—C6	179.59 (19)	C4—C5—C10—C1	3.7 (3)
C3—C4—C5—C10	−2.2 (3)	S1—N1—C12—C13	−100.2 (2)
C4—C5—C6—C7	175.95 (18)	S1—N1—C12—C14	137.2 (2)
C10—C5—C6—C7	−2.2 (3)	S2—N2—C16—C17	−111.90 (18)
C5—C6—C7—C8	−0.4 (3)	S2—N2—C16—C18	123.47 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.88	2.00	2.821 (2)	154
N2—H2B···O5ⁱⁱ	0.88	2.22	3.001 (2)	148
N2—H2B···O6ⁱⁱ	0.88	2.53	3.235 (2)	138

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₆N₂O₆S₂
M_r	430.53
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	17.229 (3), 7.2532 (15), 18.035 (4)
β (°)	108.35 (3)
V (Å³)	2139.2 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.50 × 0.38 × 0.22

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.871, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	8740, 4889, 4227
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.117, 1.16
No. of reflections	4889
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.49

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.88	2.00	2.821 (2)	153.8
N2—H2B···O5ⁱⁱ	0.88	2.22	3.001 (2)	148.2
N2—H2B···O6ⁱⁱ	0.88	2.53	3.235 (2)	138.1

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, −y+2, −z+1.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Henschel, D., Hiemisch, O., Blaschette, A. & Jones, P. G. (1996). Z. Naturforsch. Teil B, 51, 1313–1315. CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Kamoshita, K., Matsumoto, H. & Nagano, E. (1987). US Patent No. 4 670 046. Google Scholar
Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, Z. B., Zhou, S. Y. & Nie, J. (2007). J. Mol. Catal. A Chem. 265, 9–14. Web of Science CrossRef CAS Google Scholar

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Volume 64| Part 8| August 2008| Page o1499

doi:10.1107/S1600536808021211

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