1,8-Bis(4-fluoro­benzo­yl)naphthalen-2,7-diyl dimethane­sulfonate

Hijikata, D.; Sakamoto, R.; Isozaki, K.; Yonezawa, N.; Okamoto, A.

doi:10.1107/S1600536813006788

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o544

doi:10.1107/S1600536813006788

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1,8-Bis(4-fluorobenzoyl)naphthalen-2,7-diyl dimethanesulfonate

Daichi Hijikata,^a Rei Sakamoto,^a Katsuhiro Isozaki,^b Noriyuki Yonezawa ^a and Akiko Okamoto ^a ^*

^aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology (TUAT), Koganei, Tokyo 184-8588, Japan, and ^bInternational Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan
^*Correspondence e-mail: aokamoto@cc.tuat.ac.jp

(Received 7 March 2013; accepted 11 March 2013; online 16 March 2013)

The molecule of the title compound, C₂₆H₁₈F₂O₈S₂, lies across a crystallographic twofold rotation axis. The benzene rings of the 4-fluorobenzoyl groups make dihedral angles of 78.93 (12)° with the naphthalene ring system. An intramolecular C—H⋯π interaction occurs. In the crystal, a number of C—H⋯O interactions link the molecules, forming a three-dimensional structure.

Related literature

For electrophilic aromatic aroylation of the naphthalene core, see: Okamoto & Yonezawa (2009 ); Okamoto et al. (2011 ). For the crystal structures of closely related compounds, see: Watanabe et al. (2010 ); Tsumuki et al. (2011 ); Hijikata et al. (2010 , 2012 ); Sasagawa et al. (2013 ).

Experimental

Crystal data

C₂₆H₁₈F₂O₈S₂
M_r = 560.52
Monoclinic, C 2/c
a = 7.376 (3) Å
b = 16.468 (7) Å
c = 20.075 (9) Å
β = 96.123 (6)°
V = 2424.4 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 173 K
0.10 × 0.10 × 0.05 mm

Data collection

Rigaku Saturn70 diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.945, T_max = 0.945
8755 measured reflections
2360 independent reflections
1617 reflections with I > 2σ(I)
R_int = 0.074

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.120
S = 1.03
2360 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯Cg	0.98	2.87	3.805 (4)	160
C14—H14B⋯O1ⁱ	0.98	2.45	3.399 (4)	163
C14—H14C⋯O4ⁱⁱ	0.98	2.46	3.304 (4)	144
C12—H12⋯O4ⁱⁱⁱ	0.95	2.50	3.285 (4)	140
C4—H4⋯O1^iv	0.95	2.54	3.415 (4)	153
Symmetry codes: (i) $[-x, y, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+2, -z+1; (iii) -x+1, -y+2, -z+1; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2006 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: Il Milione (Burla et al., 2007 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813006788/su2570sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813006788/su2570Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813006788/su2570Isup3.cml

checkCIF report

Comment top

In the course of our study on electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds have proven to be formed regioselectively with the aid of suitable acidic mediators (Okamoto & Yonezawa, 2009; Okamoto et al., 2011). Under these circumstances, the authors have stimulated the X-ray crystal structural study of 1,8-diaroylated 2,7-dimethoxynaphthalene analogues exemplified by 1,8-bis(4-fluorobenzoyl)-2,7-dimethoxynaphthalene [(2,7-dimethoxynaphthalene-1,8-diyl)bis(4-fluorophenyl)dimethanone; Watanabe et al., 2010] and 2,7-dimethoxy-1,8-bis(2-naphthoyl)naphthalene {[2,7-dimethoxy-8-(2-naphthoyl)naphthalen-1-yl](naphthalen-2-yl)methanone; Tsumuki et al., 2011}.

Accordingly, to the best of our knowledge, these molecules have essentially the same non-coplanar features, namely: The aroyl groups at the 1,8-positions of the naphthalene ring are bonded in an almost perpendicular fashion and oriented in opposite directions (anti-orientation), but the benzene ring moieties of the aroyl groups tilt slightly toward the exo sides of the naphthalene ring. Recently, the authors have described the crystal structures of 1,8-diaroylated 2,7-dimethoxynaphthalene analogues, in which the two aroyl groups are situated in the same direction (syn-orientation), that is, 2,7-dimethoxy-1,8-bis(4-phenoxybenzoyl)naphthalene (Hijikata et al., 2010) and 2,7-dimethoxy-1,8-bis(4-isopropoxybenzoyl)naphthalene [{2,7-dimethoxy-8-[4-(propan-2-yloxy)benzoyl]naphthalen-1-yl}[4-(propan-2-yloxy)phenyl]methanone; Sasagawa et al., 2013].

The authors then investigated the correlation between the aroyl groups and the neighbouring groups in the spatial organization of 1,8-diaroylnaphthalenes. In the crystal structure of 1,8-bis(4-fluorobenzoyl)-2,7-diphenoxynaphthalene [(4-fluorophenyl)[8-(4-fluorobenzoyl)-2,7-diphenoxynaphthalen-1-yl]methanone; Hijikata et al., 2012], two phenoxy groups are asymmetrically situated with respect to the adjacent aroyl groups. One phenoxy group is horizontal to the aroyl group, whereas another phenoxy group leans toward the naphthalene ring. As a part of our continuous study on the molecular structures of this kind of homologous molecules, the crystal structure of title compound is presented herein.

The molecule of the title compound lies across a crystallographic 2-fold axis, Fig. 1, so that the asymmetric unit contains one-half of the molecule. Thus, the two aroyl groups are situated in an anti orientation and twisted away from the naphthalene ring. The benzene ring of the aroyl group make a dihedral angle of 78.93 (12) ° with the naphthalene ring. The dihedral angle between the benzene rings of the aroyl groups is 21.55 (15) °. There are two intramolecular C—H···π interactions in the molecule involving one methyl H atom (H14A) of the methanesulfonyl group and the phenyl ring of the 4-fluorobenzoyl group (Fig. 1 and Table 1).

In the crystal, the ketonic carbonyl oxygen atom (O1) and the sulfonyl oxygen atom (O4) are involved in C—H···O interactions (Fig. 2 and Table 1). These interactions contribute to the stabilization of the packing and lead to the formation a three-dimensional structure (Fig. 2 and Table 1).

Related literature top

For electrophilic aromatic aroylation of the naphthalene core, see: Okamoto & Yonezawa (2009); Okamoto et al. (2011). For the crystal structures of closely related compounds, see: Watanabe et al. (2010); Tsumuki et al. (2011); Hijikata et al. (2010, 2012); Sasagawa et al. (2013).

Experimental top

1,8-bis(4-fluorobenzoyl)-2,7-dihydroxynaphthalene (1.0 mmol, 404 mg), methanesulfonyl chloride (2.4 mmol, 487 mg), pyridine (10.0 mmol, 791 mg), and methylene chloride (2.5 ml) were placed in a 10 ml flask. The mixture was stirred at room temperature for 24 h. After the reaction, the mixture was extracted with CHCl₃. The combined extracts were washed with 2 M aqueous HCl followed by washing with brine. The organic layers thus obtained were dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give cake. The crude product was purified by recrystallization from AcOEt–hexane (v/v= 2:1) [55% isolated yield; M.p. 507.4 K], giving colourless block-like crystals. Spectroscopic data for the title compound are available in the archived CIF.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: Il Milione (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of title molecule, with atom labelling. showing The displacement ellipsoids are drawn at the 50% probability level. The intramolecular C—H···π interactions are shown as a dashed lines (see Table 1 for details; symmetry code: (i) -x+1, y, -z+1/2).
	Fig. 2. A partial crystal packing diagram of title compound. The C—H···O interactions are shown as dashed lines (see Table 1 for details).

1,8-Bis(4-fluorobenzoyl)naphthalen-2,7-diyl dimethanesulfonate top

Crystal data top

C₂₆H₁₈F₂O₈S₂	F(000) = 1152
M_r = 560.52	D_x = 1.536 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2yc	Cell parameters from 2840 reflections
a = 7.376 (3) Å	θ = 2.7–31.5°
b = 16.468 (7) Å	µ = 0.29 mm⁻¹
c = 20.075 (9) Å	T = 173 K
β = 96.123 (6)°	Block, colorless
V = 2424.4 (19) Å³	0.10 × 0.10 × 0.05 mm
Z = 4

Data collection top

Rigaku Saturn70 diffractometer	2360 independent reflections
Radiation source: rotating anode	1617 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
Detector resolution: 7.314 pixels mm^-1	θ_max = 26.0°, θ_min = 3.0°
ω scans	h = −9→9
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −20→16
T_min = 0.945, T_max = 0.945	l = −17→24
8755 measured reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0523P)² + 1.1088P] where P = (F_o² + 2F_c²)/3
2360 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₆H₁₈F₂O₈S₂	V = 2424.4 (19) Å³
M_r = 560.52	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 7.376 (3) Å	µ = 0.29 mm⁻¹
b = 16.468 (7) Å	T = 173 K
c = 20.075 (9) Å	0.10 × 0.10 × 0.05 mm
β = 96.123 (6)°

Data collection top

Rigaku Saturn70 diffractometer	2360 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	1617 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.945	R_int = 0.074
8755 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.03	Δρ_max = 0.29 e Å⁻³
2360 reflections	Δρ_min = −0.33 e Å⁻³
173 parameters

Special details top

Experimental. Spectroscopic data for the title compound:

¹H NMR δ (500 MHz, DMSO-d₆, 373 K): 3.05(6H, s), 7.16(4H, dd, J_H—H = 8.6 Hz, J_H—F = 8.6 Hz, Ar), 7.58(4H, dd, J_H—H = 8.6 Hz, J_H—F = 5.7 Hz, Ar), 7.78(2H, d, J = 9.2 Hz) 8.41(2H, d, J = 9.2 Hz) p.p.m.

¹³C NMR δ (125 MHz, DMSO-d₆, 373 K): 38.27, 114.98(d, ²J_C—F = 22.7 Hz), 120.49 127.19, 127.87, 130.29, 131.66(d, ³J_C—F = 9.5 Hz), 132.46, 133.68(d, ⁴J_C—F = 2.3 Hz), 145.61, 164.88(d, ¹J_C—F = 253.1 Hz), 191.08 p.p.m.

IR (KBr): 1673 (C=O), 1594, 1505 (Ar, naphthalene), 1354, 1169 (–SO₂–) cm^-1.

HRMS (m/z): [M + H]⁺ calcd for C₂₆H₁₉F₂O₈S₂, 561.0489 found, 561.0459

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	−0.00621 (10)	1.00592 (5)	0.39209 (3)	0.0260 (2)
F1	0.5336 (3)	0.76896 (12)	0.54084 (9)	0.0563 (6)
O1	0.2861 (3)	0.85653 (12)	0.23844 (9)	0.0294 (5)
O2	0.0714 (2)	0.99090 (12)	0.32145 (9)	0.0256 (5)
O3	−0.1713 (3)	1.05050 (13)	0.38002 (10)	0.0373 (6)
O4	0.1377 (3)	1.03864 (14)	0.43763 (10)	0.0374 (6)
C1	0.3544 (4)	0.99010 (16)	0.27833 (12)	0.0195 (6)
C2	0.2189 (4)	1.03558 (17)	0.30114 (12)	0.0223 (6)
C3	0.2174 (4)	1.12042 (17)	0.30137 (13)	0.0270 (7)
H3	0.1209	1.1497	0.3181	0.032*
C4	0.3583 (4)	1.15977 (17)	0.27698 (13)	0.0270 (7)
H4	0.3617	1.2174	0.2781	0.032*
C5	0.5000	1.1169 (2)	0.2500	0.0226 (9)
C6	0.5000	1.0305 (2)	0.2500	0.0195 (8)
C7	0.3417 (4)	0.89907 (17)	0.28618 (13)	0.0219 (6)
C8	0.3937 (4)	0.86527 (16)	0.35419 (13)	0.0213 (6)
C9	0.3690 (4)	0.78286 (17)	0.36579 (14)	0.0304 (7)
H9	0.3199	0.7488	0.3301	0.036*
C10	0.4155 (5)	0.75000 (19)	0.42896 (15)	0.0388 (8)
H10	0.3986	0.6938	0.4372	0.047*
C11	0.4865 (4)	0.8008 (2)	0.47904 (15)	0.0351 (8)
C12	0.5127 (4)	0.88178 (19)	0.46988 (14)	0.0299 (7)
H12	0.5618	0.9151	0.5060	0.036*
C13	0.4663 (4)	0.91447 (17)	0.40671 (13)	0.0247 (6)
H13	0.4841	0.9707	0.3993	0.030*
C14	−0.0504 (4)	0.90554 (19)	0.41094 (15)	0.0326 (7)
H14A	0.0650	0.8761	0.4204	0.039*
H14B	−0.1230	0.8803	0.3727	0.039*
H14C	−0.1182	0.9034	0.4503	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0244 (4)	0.0338 (4)	0.0201 (4)	−0.0002 (3)	0.0045 (3)	−0.0043 (3)
F1	0.0860 (17)	0.0496 (13)	0.0301 (11)	−0.0009 (11)	−0.0096 (10)	0.0191 (9)
O1	0.0402 (13)	0.0252 (11)	0.0221 (11)	−0.0055 (9)	0.0005 (9)	−0.0037 (9)
O2	0.0245 (11)	0.0340 (12)	0.0192 (10)	−0.0037 (9)	0.0057 (8)	−0.0036 (8)
O3	0.0278 (12)	0.0429 (14)	0.0423 (13)	0.0088 (10)	0.0089 (10)	−0.0026 (10)
O4	0.0337 (13)	0.0553 (15)	0.0230 (11)	−0.0083 (11)	0.0018 (9)	−0.0107 (10)
C1	0.0243 (14)	0.0216 (14)	0.0119 (13)	−0.0008 (12)	−0.0008 (10)	−0.0005 (10)
C2	0.0225 (15)	0.0302 (16)	0.0147 (14)	0.0001 (12)	0.0039 (11)	0.0012 (11)
C3	0.0312 (17)	0.0274 (16)	0.0225 (15)	0.0098 (13)	0.0027 (12)	−0.0010 (12)
C4	0.0344 (17)	0.0197 (15)	0.0256 (16)	0.0048 (13)	−0.0027 (13)	0.0013 (12)
C5	0.029 (2)	0.019 (2)	0.018 (2)	0.000	−0.0023 (16)	0.000
C6	0.023 (2)	0.019 (2)	0.0150 (19)	0.000	−0.0042 (15)	0.000
C7	0.0201 (15)	0.0236 (15)	0.0227 (15)	−0.0013 (12)	0.0054 (11)	−0.0005 (12)
C8	0.0215 (15)	0.0227 (15)	0.0204 (14)	−0.0007 (12)	0.0052 (11)	−0.0015 (11)
C9	0.0402 (19)	0.0229 (16)	0.0277 (17)	−0.0020 (14)	0.0019 (14)	−0.0018 (12)
C10	0.058 (2)	0.0225 (17)	0.0354 (19)	0.0004 (16)	0.0031 (16)	0.0061 (14)
C11	0.040 (2)	0.040 (2)	0.0248 (17)	0.0024 (15)	0.0031 (14)	0.0109 (14)
C12	0.0302 (17)	0.0371 (19)	0.0215 (15)	−0.0033 (14)	−0.0021 (12)	−0.0007 (13)
C13	0.0252 (16)	0.0214 (15)	0.0271 (16)	−0.0017 (12)	0.0014 (12)	0.0023 (12)
C14	0.0346 (18)	0.0398 (19)	0.0246 (16)	0.0004 (14)	0.0076 (13)	0.0011 (13)

Geometric parameters (Å, º) top

S1—O3	1.421 (2)	C5—C6	1.422 (5)
S1—O4	1.430 (2)	C6—C1ⁱ	1.432 (3)
S1—O2	1.6040 (19)	C7—C8	1.486 (4)
S1—C14	1.735 (3)	C8—C13	1.391 (4)
F1—C11	1.357 (3)	C8—C9	1.392 (4)
O1—C7	1.222 (3)	C9—C10	1.388 (4)
O2—C2	1.409 (3)	C9—H9	0.9500
C1—C2	1.366 (4)	C10—C11	1.368 (4)
C1—C6	1.432 (3)	C10—H10	0.9500
C1—C7	1.511 (4)	C11—C12	1.363 (4)
C2—C3	1.397 (4)	C12—C13	1.387 (4)
C3—C4	1.359 (4)	C12—H12	0.9500
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.416 (3)	C14—H14A	0.9800
C4—H4	0.9500	C14—H14B	0.9800
C5—C4ⁱ	1.416 (3)	C14—H14C	0.9800

O3—S1—O4	118.60 (14)	O1—C7—C1	120.4 (2)
O3—S1—O2	108.01 (12)	C8—C7—C1	117.0 (2)
O4—S1—O2	108.22 (12)	C13—C8—C9	119.2 (2)
O3—S1—C14	110.61 (15)	C13—C8—C7	121.3 (2)
O4—S1—C14	111.33 (14)	C9—C8—C7	119.5 (2)
O2—S1—C14	97.98 (12)	C10—C9—C8	120.6 (3)
C2—O2—S1	122.32 (16)	C10—C9—H9	119.7
C2—C1—C6	119.0 (3)	C8—C9—H9	119.7
C2—C1—C7	116.9 (2)	C11—C10—C9	118.1 (3)
C6—C1—C7	124.1 (2)	C11—C10—H10	120.9
C1—C2—C3	123.8 (3)	C9—C10—H10	120.9
C1—C2—O2	115.2 (2)	F1—C11—C12	118.3 (3)
C3—C2—O2	121.0 (2)	F1—C11—C10	118.5 (3)
C4—C3—C2	118.0 (3)	C12—C11—C10	123.2 (3)
C4—C3—H3	121.0	C11—C12—C13	118.6 (3)
C2—C3—H3	121.0	C11—C12—H12	120.7
C3—C4—C5	121.6 (3)	C13—C12—H12	120.7
C3—C4—H4	119.2	C12—C13—C8	120.3 (3)
C5—C4—H4	119.2	C12—C13—H13	119.8
C4—C5—C4ⁱ	120.2 (4)	C8—C13—H13	119.8
C4—C5—C6	119.90 (18)	S1—C14—H14A	109.5
C4ⁱ—C5—C6	119.90 (18)	S1—C14—H14B	109.5
C5—C6—C1	117.70 (17)	H14A—C14—H14B	109.5
C5—C6—C1ⁱ	117.70 (17)	S1—C14—H14C	109.5
C1—C6—C1ⁱ	124.6 (3)	H14A—C14—H14C	109.5
O1—C7—C8	122.5 (2)	H14B—C14—H14C	109.5

O3—S1—O2—C2	103.7 (2)	C2—C1—C6—C1ⁱ	−177.1 (3)
O4—S1—O2—C2	−25.9 (2)	C7—C1—C6—C1ⁱ	4.16 (18)
C14—S1—O2—C2	−141.5 (2)	C2—C1—C7—O1	101.4 (3)
C6—C1—C2—C3	−3.0 (4)	C6—C1—C7—O1	−79.9 (3)
C7—C1—C2—C3	175.8 (2)	C2—C1—C7—C8	−76.7 (3)
C6—C1—C2—O2	173.41 (18)	C6—C1—C7—C8	102.0 (3)
C7—C1—C2—O2	−7.8 (3)	O1—C7—C8—C13	176.3 (3)
S1—O2—C2—C1	130.4 (2)	C1—C7—C8—C13	−5.6 (4)
S1—O2—C2—C3	−53.0 (3)	O1—C7—C8—C9	−3.9 (4)
C1—C2—C3—C4	0.5 (4)	C1—C7—C8—C9	174.2 (3)
O2—C2—C3—C4	−175.7 (2)	C13—C8—C9—C10	0.2 (4)
C2—C3—C4—C5	2.0 (4)	C7—C8—C9—C10	−179.6 (3)
C3—C4—C5—C4ⁱ	178.0 (3)	C8—C9—C10—C11	−0.2 (5)
C3—C4—C5—C6	−2.0 (3)	C9—C10—C11—F1	−179.5 (3)
C4—C5—C6—C1	−0.47 (16)	C9—C10—C11—C12	0.3 (5)
C4ⁱ—C5—C6—C1	179.53 (16)	F1—C11—C12—C13	179.5 (3)
C4—C5—C6—C1ⁱ	179.53 (16)	C10—C11—C12—C13	−0.4 (5)
C4ⁱ—C5—C6—C1ⁱ	−0.47 (16)	C11—C12—C13—C8	0.3 (4)
C2—C1—C6—C5	2.9 (3)	C9—C8—C13—C12	−0.3 (4)
C7—C1—C6—C5	−175.84 (18)	C7—C8—C13—C12	179.6 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···Cg	0.98	2.87	3.805 (4)	160
C14—H14B···O1ⁱⁱ	0.98	2.45	3.399 (4)	163
C14—H14C···O4ⁱⁱⁱ	0.98	2.46	3.304 (4)	144
C12—H12···O4^iv	0.95	2.50	3.285 (4)	140
C4—H4···O1^v	0.95	2.54	3.415 (4)	153

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

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈F₂O₈S₂
M_r	560.52
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	7.376 (3), 16.468 (7), 20.075 (9)
β (°)	96.123 (6)
V (Å³)	2424.4 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.10 × 0.10 × 0.05

Data collection
Diffractometer	Rigaku Saturn70 diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.945, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	8755, 2360, 1617
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.120, 1.03
No. of reflections	2360
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.33

Computer programs: CrystalClear (Rigaku/MSC, 2006), Il Milione (Burla et al., 2007), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···Cg	0.98	2.87	3.805 (4)	160
C14—H14B···O1ⁱ	0.98	2.45	3.399 (4)	163
C14—H14C···O4ⁱⁱ	0.98	2.46	3.304 (4)	144
C12—H12···O4ⁱⁱⁱ	0.95	2.50	3.285 (4)	140
C4—H4···O1^iv	0.95	2.54	3.415 (4)	153

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

Acknowledgements

The authors express their gratitude to Associate Professor Hikaru Takaya and Professor Masaharu Nakamura, Institute for Chemical Research, Kyoto University, for their kind advice. This work was partially supported by the Collaborative Research Program of the Institute for Chemical Research, Kyoto University (grant No. 2012–72).

References

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Volume 69| Part 4| April 2013| Page o544

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