2,2′-[2,4-Bis(naphthalen-1-yl)cyclo­butane-1,3-di­yl]bis­(1-methyl­pyridinium) bis­(4-chloro­benzene­sulfonate): thermal-induced [2 + 2] cyclo­addition reaction of a heterostilbene

Chantrapromma, S.; Chanawanno, K.; Boonnak, N.; Fun, H.-K.

doi:10.1107/S160053681400645X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Pages o510-o511

doi:10.1107/S160053681400645X

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2,2′-[2,4-Bis(naphthalen-1-yl)cyclobutane-1,3-diyl]bis(1-methylpyridinium) bis(4-chlorobenzenesulfonate): thermal-induced [2 + 2] cycloaddition reaction of a heterostilbene

Suchada Chantrapromma,^a ^*‡ Kullapa Chanawanno,^a Nawong Boonnak ^b and Hoong-Kun Fun ^c §

^aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^bFaculty of Traditional Thai Medicine, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 9 March 2014; accepted 24 March 2014; online 2 April 2014)

The asymmetric unit of the title salt, C₃₆H₃₂N₂²⁺·2C₆H₄ClO₃S⁻, consists of one anion and one half-cation, the other half being generated by inversion symmetry. The dihedral angle between the pyridinium ring and the napthalene ring system in the asymmetric unit is 42.86 (6)°. In the crystal, cations and anions are linked by weak C—H⋯O interactions into chains along [010]. Adjacent chains are further arranged in an antiparallel manner into sheets parallel to the bc plane. π–π interactions are observed involving the cations, with centroid–centroid distances of 3.7664 (8) and 3.8553 (8) Å.

CCDC reference: 993267

Related literature

For background to stibene and [2 + 2] photodimerization, see: Chanawanno et al. (2010 ); Chantrapromma et al. (2007 ); Papaefstathiou et al. (2002 ); Ruanwas et al. (2010 ); Yayli et al. (2004 ); Zhang et al. (2013 ). For related structures, see: Chantrapromma et al. (2012 ); Fun, Chanawanno & Chantrapromma (2009 ); Fun, Surasit et al. (2009 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₃₆H₃₂N₂²⁺·2C₆H₄ClO₃S⁻
M_r = 875.86
Triclinic, $[P \overline 1]$
a = 7.5488 (3) Å
b = 11.1899 (4) Å
c = 12.3853 (5) Å
α = 79.904 (2)°
β = 75.964 (2)°
γ = 89.266 (2)°
V = 998.76 (7) Å³
Z = 1
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 100 K
0.56 × 0.50 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.837, T_max = 0.936
35475 measured reflections
5817 independent reflections
4977 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.115
S = 1.09
5817 reflections
351 parameters
All H-atom parameters refined
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.74 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O3	0.97 (2)	2.51 (2)	3.3762 (18)	147.9 (18)
C17—H17⋯O2ⁱ	0.974 (17)	2.506 (18)	3.3001 (18)	138.6 (13)
C20—H20⋯O2	0.97 (2)	2.20 (2)	3.1329 (18)	160.5 (19)
C23—H23⋯O1ⁱⁱ	0.94 (2)	2.41 (2)	3.1554 (17)	135.8 (18)
C24—H24B⋯O1ⁱⁱ	0.95 (2)	2.57 (2)	3.2009 (18)	124.3 (16)
C9—H9⋯Cg4ⁱⁱⁱ	1.00 (2)	2.98 (2)	3.4790 (16)	112.1 (16)
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) x, y+1, z; (iii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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, PLATON (Spek, 2009 ), Mercury (Macrae et al., 2006 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 993267

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681400645X/rz5110sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681400645X/rz5110Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681400645X/rz5110Isup3.cml

checkCIF report

Comment top

Stilbene derivatives have been reported to exhibit non-linear optical (NLO) property (Ruanwas et al., 2010) and antibacterial activity (Chanawanno et al., 2010). It has been known that [2 + 2] photodimerization of stilbenes to yield cyclobutane can occur (Papaefstathiou et al., 2002). In our cases, the [2 + 2] cycloaddition of heterostilbene derivatives was carried out in solution by thermal-induced cycloaddition reaction, and we have previously reported the crystal structures of some of these derivatives (Chantrapromma et al., 2012; Fun, Chanawanno & Chantrapromma, 2009; Fun, Surasit et al., 2009). The title compound (I) was obtained by the cycloaddition of trans-heterostilbene to give a syn head-to-tail product (Yayli et al., 2004; Zhang et al., 2013). We report herein the synthesis and crystal structure of (I).

The asymmetric unit of (I), C₃₆H₃₂N₂²⁺·2(C₆H₄ClO₃S^-), consists of one half of a cation and one anion. The cation lies on an inversion center and the other half is generated by the symmetry operator 2-x, 1-y, 2-z (Fig. 1). The napthalene (C7–C16) moiety is planar with a r.m.s. of 0.0183 (2) Å. The dihedral angle between the pyridinium ring (N1/C19–C23) and the napthalene ring system is 42.86 (6)°. The steroisomer of (I) is syn head-to-tail (Yayli et al., 2004). The cyclobutane ring makes dihedral angles of 85.61 (8) and 52.8 (6)° with the pyridinium and naphthalene rings, respectively. The bond lengths are in normal ranges (Allen et al., 1987) and comparable with those found in closely related structures (Chantrapromma et al., 2012; Fun, Surasit et al., 2009; Fun, Chanawanno & Chantrapromma (2009).

The crystal packing of (I) is shown in Fig. 2. The cations and anions are alternatively arranged and linked into chains along the [0 1 0] direction through C—H···O weak interactions (Table 1). Adjacent chains are arranged in a anti-parallel manner into sheets parallel to the (1 0 0) plane. π···π interactions are present with distances of Cg₁···Cg₂ = 3.8553 (8) Å and Cg₁···Cg₃ = 3.7664 (8) Å; Cg₁, Cg₂ and Cg₃ are the centroids of the N1/C19–C23, C7–C10/C15/C16 and C10–C15 rings, respectively (Fig. 3). C—H···π weak interactions are also observed (Table 1).

Related literature top

For background to stibene and [2 + 2] photodimerization, see: Chanawanno et al. (2010); Chantrapromma et al. (2007); Papaefstathiou et al. (2002); Ruanwas et al. (2010); Yayli et al. (2004); Zhang et al. (2013). For related structures, see: Chantrapromma et al. (2012); Fun, Chanawanno & Chantrapromma (2009); Fun, Surasit et al. (2009). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A solution of (E)-1-methyl-2-[2-(1-naphthyl)vinyl)pyridinium iodide (0.25 g, 0.67 mmol) in CH₃OH (20 ml) was mixed (1:1 molar ratio) with a solution of silver(I) 4-chlorobenzenesulfonate (0.20 g, 0.67 mmol) (Chantrapromma et al., 2007) in CH₃OH (80 ml) and stirred for 30 min. The precipitate of silver iodide which formed was filtered and the filtrate was evaporated to give a yellow solid product. The yellow solid was repeatedly recrystallized for three times by dissolving the yellow solid in CH₃OH and the solution was heated at 323 K to get a clear solution. The [2 + 2] cycloaddition of (E)-1-methyl-2-[2-(1-naphthyl)vinyl)pyridinium occurred upon heating. Yellow plate-shaped single crystals of the title compound suitable for X-ray structure determination were obtained after recrystallization in CH₃OH by slow evaporation of the solvent at room temperature after a few weeks.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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), PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids. Symmetry code: (A) 2-x, 1-y, 2-z,
	Fig. 2. The crystal packing of the title compound viewed down the a axis. H atoms not involved in C—H···O interactions (dashed lines) are omitted for clarity.
	Fig. 3. The π···π stacking interactions between the pyridinium and napthalene rings. H atoms are omitted for clarity.

2,2'-[2,4-Bis(naphthalen-1-yl)cyclobutane-1,3-diyl]bis(1-methylpyridinium) bis(4-chlorobenzenesulfonate) top

Crystal data top

C₃₆H₃₂N₂²⁺·2C₆H₄ClO₃S⁻	Z = 1
M_r = 875.86	F(000) = 456
Triclinic, P1	D_x = 1.456 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5488 (3) Å	Cell parameters from 5817 reflections
b = 11.1899 (4) Å	θ = 1.9–30.0°
c = 12.3853 (5) Å	µ = 0.32 mm⁻¹
α = 79.904 (2)°	T = 100 K
β = 75.964 (2)°	Plate, yellow
γ = 89.266 (2)°	0.56 × 0.50 × 0.21 mm
V = 998.76 (7) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	5817 independent reflections
Radiation source: sealed tube	4977 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
T_min = 0.837, T_max = 0.936	k = −15→15
35475 measured reflections	l = −17→17

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	All H-atom parameters refined
S = 1.09	w = 1/[σ²(F_o²) + (0.052P)² + 0.7427P] where P = (F_o² + 2F_c²)/3
5817 reflections	(Δ/σ)_max = 0.001
351 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.74 e Å⁻³

Crystal data top

C₃₆H₃₂N₂²⁺·2C₆H₄ClO₃S⁻	γ = 89.266 (2)°
M_r = 875.86	V = 998.76 (7) Å³
Triclinic, P1	Z = 1
a = 7.5488 (3) Å	Mo Kα radiation
b = 11.1899 (4) Å	µ = 0.32 mm⁻¹
c = 12.3853 (5) Å	T = 100 K
α = 79.904 (2)°	0.56 × 0.50 × 0.21 mm
β = 75.964 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5817 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4977 reflections with I > 2σ(I)
T_min = 0.837, T_max = 0.936	R_int = 0.031
35475 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.115	All H-atom parameters refined
S = 1.09	Δρ_max = 0.50 e Å⁻³
5817 reflections	Δρ_min = −0.74 e Å⁻³
351 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	0.34039 (7)	0.25081 (7)	0.47197 (4)	0.05223 (17)
S1	0.78639 (5)	0.19952 (3)	0.84360 (3)	0.01743 (9)
O1	0.73608 (18)	0.08040 (9)	0.91361 (10)	0.0249 (2)
O2	0.73144 (17)	0.29857 (10)	0.90582 (9)	0.0247 (2)
O3	0.97566 (16)	0.21127 (10)	0.77961 (10)	0.0245 (2)
N1	0.71757 (16)	0.75327 (10)	0.97380 (10)	0.0141 (2)
C1	0.65583 (19)	0.21394 (13)	0.74055 (12)	0.0169 (2)
C2	0.6222 (2)	0.11222 (14)	0.69692 (13)	0.0216 (3)
H2	0.669 (3)	0.036 (2)	0.7248 (18)	0.030 (5)*
C3	0.5228 (2)	0.12351 (18)	0.61444 (14)	0.0295 (4)
H3	0.499 (4)	0.050 (2)	0.587 (2)	0.048 (7)*
C4	0.4605 (2)	0.23620 (19)	0.57678 (13)	0.0310 (4)
C5	0.4931 (2)	0.33809 (18)	0.61922 (14)	0.0306 (4)
H5	0.445 (4)	0.416 (2)	0.594 (2)	0.044 (7)*
C6	0.5919 (2)	0.32641 (15)	0.70183 (13)	0.0243 (3)
H6	0.614 (3)	0.399 (2)	0.733 (2)	0.043 (7)*
C7	1.1080 (2)	0.50647 (12)	0.73600 (12)	0.0171 (3)
H7	1.107 (3)	0.420 (2)	0.7661 (18)	0.031 (5)*
C8	1.0998 (2)	0.54409 (13)	0.62185 (12)	0.0201 (3)
H8	1.094 (3)	0.4832 (19)	0.5774 (17)	0.023 (5)*
C9	1.0930 (2)	0.66488 (14)	0.57787 (12)	0.0198 (3)
H9	1.083 (3)	0.692 (2)	0.498 (2)	0.037 (6)*
C10	1.09915 (19)	0.75385 (12)	0.64568 (11)	0.0166 (2)
C11	1.0880 (2)	0.87977 (13)	0.60332 (12)	0.0201 (3)
H11	1.079 (3)	0.9014 (19)	0.5266 (17)	0.025 (5)*
C12	1.0923 (2)	0.96528 (13)	0.66949 (13)	0.0214 (3)
H12	1.081 (3)	1.0496 (19)	0.6386 (17)	0.025 (5)*
C13	1.1119 (2)	0.92916 (12)	0.78099 (13)	0.0187 (3)
H13	1.113 (3)	0.9900 (19)	0.8269 (17)	0.024 (5)*
C14	1.12389 (19)	0.80819 (12)	0.82451 (12)	0.0156 (2)
H14	1.139 (3)	0.7860 (17)	0.9006 (16)	0.016 (4)*
C15	1.11430 (18)	0.71681 (12)	0.75936 (11)	0.0139 (2)
C16	1.11371 (18)	0.58955 (12)	0.80500 (11)	0.0136 (2)
C17	1.10424 (18)	0.55360 (11)	0.92961 (11)	0.0127 (2)
H17	1.208 (2)	0.5887 (16)	0.9483 (15)	0.013 (4)*
C18	0.92111 (18)	0.58354 (11)	1.01586 (11)	0.0128 (2)
H18	0.951 (3)	0.6318 (18)	1.0651 (17)	0.022 (5)*
C19	0.77448 (17)	0.63876 (11)	0.96192 (11)	0.0127 (2)
C20	0.70618 (18)	0.58062 (12)	0.88915 (12)	0.0154 (2)
H20	0.743 (3)	0.4980 (18)	0.8833 (17)	0.023 (5)*
C21	0.59784 (19)	0.64167 (13)	0.82278 (12)	0.0175 (3)
H21	0.552 (3)	0.6025 (19)	0.7721 (18)	0.027 (5)*
C22	0.5555 (2)	0.76146 (13)	0.83035 (13)	0.0187 (3)
H22	0.478 (3)	0.806 (2)	0.7852 (18)	0.028 (5)*
C23	0.61171 (19)	0.81340 (12)	0.90961 (12)	0.0174 (3)
H23	0.578 (3)	0.8907 (19)	0.9267 (17)	0.025 (5)*
C24	0.7691 (2)	0.81744 (13)	1.05723 (12)	0.0178 (3)
H24A	0.750 (3)	0.7626 (19)	1.1291 (17)	0.023 (5)*
H24B	0.694 (3)	0.886 (2)	1.0634 (18)	0.031 (6)*
H24C	0.895 (3)	0.8424 (19)	1.0323 (18)	0.027 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0367 (3)	0.0909 (5)	0.0291 (2)	−0.0113 (3)	−0.02130 (19)	0.0088 (2)
S1	0.02519 (18)	0.00977 (15)	0.02051 (17)	−0.00007 (12)	−0.01122 (13)	−0.00329 (11)
O1	0.0397 (6)	0.0112 (4)	0.0270 (5)	−0.0022 (4)	−0.0167 (5)	0.0003 (4)
O2	0.0404 (7)	0.0139 (5)	0.0229 (5)	−0.0003 (4)	−0.0111 (5)	−0.0072 (4)
O3	0.0231 (5)	0.0204 (5)	0.0343 (6)	0.0009 (4)	−0.0135 (5)	−0.0069 (4)
N1	0.0151 (5)	0.0097 (5)	0.0181 (5)	0.0009 (4)	−0.0051 (4)	−0.0023 (4)
C1	0.0177 (6)	0.0167 (6)	0.0171 (6)	0.0012 (5)	−0.0057 (5)	−0.0030 (5)
C2	0.0245 (7)	0.0209 (7)	0.0214 (7)	−0.0032 (5)	−0.0083 (5)	−0.0049 (5)
C3	0.0287 (8)	0.0401 (10)	0.0219 (7)	−0.0094 (7)	−0.0096 (6)	−0.0057 (7)
C4	0.0197 (7)	0.0538 (11)	0.0184 (7)	−0.0029 (7)	−0.0081 (6)	0.0016 (7)
C5	0.0262 (8)	0.0377 (9)	0.0245 (7)	0.0105 (7)	−0.0072 (6)	0.0040 (7)
C6	0.0284 (8)	0.0219 (7)	0.0224 (7)	0.0073 (6)	−0.0073 (6)	−0.0021 (6)
C7	0.0210 (6)	0.0130 (6)	0.0174 (6)	0.0022 (5)	−0.0050 (5)	−0.0024 (5)
C8	0.0263 (7)	0.0181 (6)	0.0176 (6)	0.0027 (5)	−0.0069 (5)	−0.0057 (5)
C9	0.0236 (7)	0.0203 (7)	0.0154 (6)	0.0030 (5)	−0.0060 (5)	−0.0019 (5)
C10	0.0176 (6)	0.0149 (6)	0.0162 (6)	0.0021 (5)	−0.0043 (5)	0.0000 (5)
C11	0.0238 (7)	0.0164 (6)	0.0185 (6)	0.0030 (5)	−0.0062 (5)	0.0023 (5)
C12	0.0241 (7)	0.0131 (6)	0.0246 (7)	0.0015 (5)	−0.0050 (5)	0.0018 (5)
C13	0.0204 (6)	0.0118 (6)	0.0234 (7)	−0.0002 (5)	−0.0055 (5)	−0.0016 (5)
C14	0.0166 (6)	0.0119 (6)	0.0177 (6)	−0.0008 (4)	−0.0044 (5)	−0.0012 (5)
C15	0.0141 (5)	0.0111 (5)	0.0161 (6)	0.0004 (4)	−0.0042 (4)	−0.0006 (4)
C16	0.0141 (5)	0.0114 (5)	0.0150 (5)	0.0008 (4)	−0.0041 (4)	−0.0007 (4)
C17	0.0144 (5)	0.0086 (5)	0.0153 (5)	0.0006 (4)	−0.0048 (4)	−0.0013 (4)
C18	0.0142 (5)	0.0091 (5)	0.0155 (5)	0.0009 (4)	−0.0053 (4)	−0.0009 (4)
C19	0.0130 (5)	0.0087 (5)	0.0161 (6)	0.0006 (4)	−0.0038 (4)	−0.0010 (4)
C20	0.0163 (6)	0.0109 (5)	0.0197 (6)	0.0001 (4)	−0.0059 (5)	−0.0027 (5)
C21	0.0176 (6)	0.0155 (6)	0.0215 (6)	−0.0010 (5)	−0.0087 (5)	−0.0029 (5)
C22	0.0174 (6)	0.0153 (6)	0.0246 (7)	0.0021 (5)	−0.0097 (5)	−0.0007 (5)
C23	0.0172 (6)	0.0112 (5)	0.0244 (7)	0.0035 (5)	−0.0074 (5)	−0.0017 (5)
C24	0.0225 (7)	0.0129 (6)	0.0204 (6)	0.0033 (5)	−0.0077 (5)	−0.0063 (5)

Geometric parameters (Å, º) top

Cl1—C4	1.7397 (16)	C11—C12	1.370 (2)
S1—O3	1.4511 (12)	C11—H11	0.96 (2)
S1—O1	1.4564 (11)	C12—C13	1.412 (2)
S1—O2	1.4584 (11)	C12—H12	0.96 (2)
S1—C1	1.7776 (14)	C13—C14	1.3769 (18)
N1—C23	1.3529 (17)	C13—H13	0.96 (2)
N1—C19	1.3673 (16)	C14—C15	1.4217 (18)
N1—C24	1.4823 (17)	C14—H14	0.965 (19)
C1—C6	1.390 (2)	C15—C16	1.4368 (17)
C1—C2	1.394 (2)	C16—C17	1.5094 (18)
C2—C3	1.395 (2)	C17—C18ⁱ	1.5585 (17)
C2—H2	0.96 (2)	C17—C18	1.6005 (18)
C3—C4	1.383 (3)	C17—H17	0.974 (19)
C3—H3	0.97 (3)	C18—C19	1.5000 (18)
C4—C5	1.384 (3)	C18—C17ⁱ	1.5585 (17)
C5—C6	1.394 (2)	C18—H18	0.95 (2)
C5—H5	0.98 (3)	C19—C20	1.3932 (18)
C6—H6	0.99 (3)	C20—C21	1.3879 (19)
C7—C16	1.3761 (18)	C20—H20	0.97 (2)
C7—C8	1.4189 (19)	C21—C22	1.388 (2)
C7—H7	0.98 (2)	C21—H21	0.95 (2)
C8—C9	1.371 (2)	C22—C23	1.375 (2)
C8—H8	0.96 (2)	C22—H22	0.98 (2)
C9—C10	1.418 (2)	C23—H23	0.94 (2)
C9—H9	1.00 (2)	C24—H24A	0.97 (2)
C10—C11	1.4237 (19)	C24—H24B	0.95 (2)
C10—C15	1.4282 (18)	C24—H24C	0.96 (2)

O3—S1—O1	113.75 (7)	C14—C13—C12	120.46 (13)
O3—S1—O2	113.02 (7)	C14—C13—H13	120.5 (12)
O1—S1—O2	112.70 (7)	C12—C13—H13	119.0 (12)
O3—S1—C1	105.26 (7)	C13—C14—C15	121.07 (13)
O1—S1—C1	105.65 (7)	C13—C14—H14	118.8 (11)
O2—S1—C1	105.50 (7)	C15—C14—H14	120.1 (11)
C23—N1—C19	121.43 (12)	C14—C15—C10	118.30 (12)
C23—N1—C24	116.89 (11)	C14—C15—C16	122.34 (12)
C19—N1—C24	121.68 (11)	C10—C15—C16	119.33 (12)
C6—C1—C2	120.35 (14)	C7—C16—C15	118.98 (12)
C6—C1—S1	120.19 (11)	C7—C16—C17	123.07 (12)
C2—C1—S1	119.44 (11)	C15—C16—C17	117.77 (11)
C1—C2—C3	119.68 (15)	C16—C17—C18ⁱ	118.70 (11)
C1—C2—H2	118.5 (13)	C16—C17—C18	117.06 (11)
C3—C2—H2	121.8 (13)	C18ⁱ—C17—C18	90.59 (9)
C4—C3—C2	119.18 (16)	C16—C17—H17	110.6 (11)
C4—C3—H3	122.9 (16)	C18ⁱ—C17—H17	109.6 (11)
C2—C3—H3	117.9 (16)	C18—C17—H17	108.5 (10)
C3—C4—C5	121.80 (15)	C19—C18—C17ⁱ	117.10 (11)
C3—C4—Cl1	119.17 (15)	C19—C18—C17	115.18 (11)
C5—C4—Cl1	119.03 (15)	C17ⁱ—C18—C17	89.41 (9)
C4—C5—C6	118.86 (16)	C19—C18—H18	111.7 (12)
C4—C5—H5	120.9 (15)	C17ⁱ—C18—H18	112.1 (12)
C6—C5—H5	120.3 (15)	C17—C18—H18	109.4 (12)
C1—C6—C5	120.13 (16)	N1—C19—C20	117.97 (12)
C1—C6—H6	120.6 (15)	N1—C19—C18	120.58 (11)
C5—C6—H6	119.2 (15)	C20—C19—C18	121.12 (11)
C16—C7—C8	121.32 (13)	C21—C20—C19	120.72 (12)
C16—C7—H7	119.8 (13)	C21—C20—H20	121.6 (12)
C8—C7—H7	118.9 (13)	C19—C20—H20	117.6 (12)
C9—C8—C7	120.64 (13)	C20—C21—C22	119.42 (13)
C9—C8—H8	120.8 (12)	C20—C21—H21	120.9 (13)
C7—C8—H8	118.5 (12)	C22—C21—H21	119.6 (13)
C8—C9—C10	120.03 (13)	C23—C22—C21	118.63 (13)
C8—C9—H9	120.9 (14)	C23—C22—H22	120.2 (13)
C10—C9—H9	119.0 (14)	C21—C22—H22	121.0 (13)
C9—C10—C11	121.36 (13)	N1—C23—C22	121.37 (13)
C9—C10—C15	119.59 (12)	N1—C23—H23	114.0 (13)
C11—C10—C15	119.04 (13)	C22—C23—H23	124.6 (13)
C12—C11—C10	121.14 (13)	N1—C24—H24A	109.0 (12)
C12—C11—H11	122.0 (12)	N1—C24—H24B	107.3 (14)
C10—C11—H11	116.8 (12)	H24A—C24—H24B	111.1 (18)
C11—C12—C13	119.94 (13)	N1—C24—H24C	109.9 (13)
C11—C12—H12	118.9 (12)	H24A—C24—H24C	108.7 (18)
C13—C12—H12	121.2 (12)	H24B—C24—H24C	110.7 (19)

O3—S1—C1—C6	−93.88 (13)	C11—C10—C15—C16	176.00 (12)
O1—S1—C1—C6	145.45 (13)	C8—C7—C16—C15	−1.0 (2)
O2—S1—C1—C6	25.87 (14)	C8—C7—C16—C17	173.93 (13)
O3—S1—C1—C2	84.49 (13)	C14—C15—C16—C7	−178.65 (13)
O1—S1—C1—C2	−36.18 (14)	C10—C15—C16—C7	3.31 (19)
O2—S1—C1—C2	−155.76 (12)	C14—C15—C16—C17	6.13 (19)
C6—C1—C2—C3	−0.4 (2)	C10—C15—C16—C17	−171.91 (12)
S1—C1—C2—C3	−178.75 (12)	C7—C16—C17—C18ⁱ	−2.56 (19)
C1—C2—C3—C4	0.5 (2)	C15—C16—C17—C18ⁱ	172.45 (11)
C2—C3—C4—C5	−0.4 (3)	C7—C16—C17—C18	−109.58 (14)
C2—C3—C4—Cl1	178.78 (13)	C15—C16—C17—C18	65.43 (15)
C3—C4—C5—C6	0.2 (3)	C16—C17—C18—C19	3.08 (16)
Cl1—C4—C5—C6	−178.95 (13)	C18ⁱ—C17—C18—C19	−119.90 (13)
C2—C1—C6—C5	0.2 (2)	C16—C17—C18—C17ⁱ	122.98 (13)
S1—C1—C6—C5	178.57 (13)	C18ⁱ—C17—C18—C17ⁱ	0.0
C4—C5—C6—C1	−0.1 (3)	C23—N1—C19—C20	−6.00 (19)
C16—C7—C8—C9	−1.5 (2)	C24—N1—C19—C20	174.15 (12)
C7—C8—C9—C10	1.7 (2)	C23—N1—C19—C18	167.49 (12)
C8—C9—C10—C11	−178.48 (14)	C24—N1—C19—C18	−12.36 (19)
C8—C9—C10—C15	0.6 (2)	C17ⁱ—C18—C19—N1	139.98 (12)
C9—C10—C11—C12	179.41 (14)	C17—C18—C19—N1	−116.85 (13)
C15—C10—C11—C12	0.3 (2)	C17ⁱ—C18—C19—C20	−46.74 (17)
C10—C11—C12—C13	1.3 (2)	C17—C18—C19—C20	56.43 (16)
C11—C12—C13—C14	−1.0 (2)	N1—C19—C20—C21	6.1 (2)
C12—C13—C14—C15	−0.9 (2)	C18—C19—C20—C21	−167.36 (13)
C13—C14—C15—C10	2.5 (2)	C19—C20—C21—C22	−0.8 (2)
C13—C14—C15—C16	−175.60 (13)	C20—C21—C22—C23	−4.6 (2)
C9—C10—C15—C14	178.74 (13)	C19—N1—C23—C22	0.6 (2)
C11—C10—C15—C14	−2.1 (2)	C24—N1—C23—C22	−179.56 (13)
C9—C10—C15—C16	−3.1 (2)	C21—C22—C23—N1	4.8 (2)

Symmetry code: (i) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3	0.97 (2)	2.51 (2)	3.3762 (18)	147.9 (18)
C17—H17···O2ⁱ	0.974 (17)	2.506 (18)	3.3001 (18)	138.6 (13)
C20—H20···O2	0.97 (2)	2.20 (2)	3.1329 (18)	160.5 (19)
C23—H23···O1ⁱⁱ	0.94 (2)	2.41 (2)	3.1554 (17)	135.8 (18)
C24—H24B···O1ⁱⁱ	0.95 (2)	2.57 (2)	3.2009 (18)	124.3 (16)
C9—H9···Cg4ⁱⁱⁱ	1.00 (2)	2.98 (2)	3.4790 (16)	112.1 (16)

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

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3	0.97 (2)	2.51 (2)	3.3762 (18)	147.9 (18)
C17—H17···O2ⁱ	0.974 (17)	2.506 (18)	3.3001 (18)	138.6 (13)
C20—H20···O2	0.97 (2)	2.20 (2)	3.1329 (18)	160.5 (19)
C23—H23···O1ⁱⁱ	0.94 (2)	2.41 (2)	3.1554 (17)	135.8 (18)
C24—H24B···O1ⁱⁱ	0.95 (2)	2.57 (2)	3.2009 (18)	124.3 (16)
C9—H9···Cg4ⁱⁱⁱ	1.00 (2)	2.98 (2)	3.4790 (16)	112.1 (16)

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

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Department of Chemistry, Faculty of Science, Prince of Songkla University, for the research facility and extend their appreciation to the Malaysian Government and Universiti Sains Malaysia for APEX DE2012 grant No. 1002/PFIZIK/910323.

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Volume 70| Part 5| May 2014| Pages o510-o511

doi:10.1107/S160053681400645X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,2′-[2,4-Bis(naphthalen-1-yl)cyclo­butane-1,3-di­yl]bis­­(1-methyl­pyridinium) bis­­(4-chloro­benzene­sulfonate): thermal-induced [2 + 2] cyclo­addition reaction of a heterostilbene

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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Acknowledgements

References

organic compounds

2,2′-[2,4-Bis(naphthalen-1-yl)cyclobutane-1,3-diyl]bis(1-methylpyridinium) bis(4-chlorobenzenesulfonate): thermal-induced [2 + 2] cycloaddition reaction of a heterostilbene