1,8-Bis(4-fluoro-benzo-yl)naphthalen-2,7-diyl dimethane-sulfonate.

The mol-ecule 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 intra-molecular C-H⋯π inter-action occurs. In the crystal, a number of C-H⋯O inter-actions link the mol-ecules, 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 = 560.52

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.120

S = 1.03

2360 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.33 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813006788/su2570sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006788/su2570Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H18F2O8S2	F(000) = 1152
Mr = 560.52	Dx = 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

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

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(Fo2) + (0.0523P)2 + 1.1088P] where P = (Fo2 + 2Fc2)/3
2360 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Experimental. Spectroscopic data for the title compound:1H NMR δ (500 MHz, DMSO-d6, 373 K): 3.05(6H, s), 7.16(4H, dd, JH—H = 8.6 Hz, JH—F = 8.6 Hz, Ar), 7.58(4H, dd, JH—H = 8.6 Hz, JH—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, 2JC—F = 22.7 Hz), 120.49 127.19, 127.87, 130.29, 131.66(d, 3JC—F = 9.5 Hz), 132.46, 133.68(d, 4JC—F = 2.3 Hz), 145.61, 164.88(d, 1JC—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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···O4iv	0.95	2.50	3.285 (4)	140
C4—H4···O1v	0.95	2.54	3.415 (4)	153

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⋯O1iv	0.95	2.54	3.415 (4)	153

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .