3,6-Dibromo-naphthalene-2,7-diyl bis-(trifluoro-methane-sulfonate).

The naphthalene fused ring of the title compound, C(12)H(4)Br(2)F(6)O(6)S(2), is slightly buckled (r.m.s. deviation = 0.036 Å) along the common C-C bond and the benzene rings are twisted by 3.2 (3)°. The two trifluoro-methyl-sulfonyl groups lie on opposite sides of the fused-ring system. The crystal structure features short inter-molecular F⋯F contacts [2.715 (4) and 2.832 (4) Å].

Related literature

For the synthesis and background chemistry, see: Shinamura et al. (2011 ▶).

Experimental

Crystal data

C12H4Br2F6O6S2

M = 582.09

Monoclinic,

a = 5.2413 (11) Å

b = 26.450 (6) Å

c = 12.429 (3) Å

β = 90.169 (3)°

V = 1723.1 (7) Å3

Z = 4

Mo Kα radiation

μ = 5.04 mm−1

T = 173 K

0.32 × 0.30 × 0.20 mm

Data collection

Rigaku Saturn724+ CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.573, T max = 1.000

17398 measured reflections

3933 independent reflections

3662 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.094

S = 1.16

3933 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037755/nk2112sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037755/nk2112Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037755/nk2112Isup3.cml

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

C12H4Br2F6O6S2	F(000) = 1120
Mr = 582.09	Dx = 2.244 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5210 reflections
a = 5.2413 (11) Å	θ = 0.8–27.5°
b = 26.450 (6) Å	µ = 5.04 mm−1
c = 12.429 (3) Å	T = 173 K
β = 90.169 (3)°	Prism, colourless
V = 1723.1 (7) Å3	0.32 × 0.30 × 0.20 mm
Z = 4

Rigaku Saturn724+ CCD diffractometer	3933 independent reflections
Radiation source: fine-focus sealed tube	3662 reflections with I > 2σ(I)
graphite	Rint = 0.048
ω scans at fixed χ = 45°	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	h = −6→6
Tmin = 0.573, Tmax = 1.000	k = −34→34
17398 measured reflections	l = −16→16

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-atom parameters constrained
S = 1.16	w = 1/[σ2(Fo2) + (0.0349P)2 + 2.4738P] where P = (Fo2 + 2Fc2)/3
3933 reflections	(Δ/σ)max = 0.001
253 parameters	Δρmax = 0.79 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	−0.38667 (8)	0.159089 (15)	0.15955 (3)	0.03395 (12)
Br2	0.69892 (7)	0.232466 (15)	0.59710 (3)	0.03228 (12)
S1	−0.51801 (18)	0.01955 (4)	0.30367 (8)	0.0297 (2)
S2	0.36288 (18)	0.17543 (4)	0.81831 (7)	0.0286 (2)
F1	−0.4753 (6)	0.03529 (11)	0.0989 (2)	0.0519 (7)
F2	−0.8431 (5)	0.05488 (10)	0.1624 (2)	0.0486 (7)
F3	−0.7393 (6)	−0.02313 (10)	0.1425 (2)	0.0576 (8)
F4	−0.0166 (5)	0.11242 (10)	0.8258 (2)	0.0501 (7)
F5	0.3216 (6)	0.08682 (11)	0.9073 (2)	0.0634 (8)
F6	0.0909 (5)	0.14491 (11)	0.9781 (2)	0.0506 (7)
O1	−0.5105 (5)	0.07808 (10)	0.3257 (2)	0.0295 (6)
O2	−0.2705 (6)	−0.00101 (11)	0.2966 (3)	0.0435 (7)
O3	−0.7065 (6)	−0.00149 (13)	0.3702 (3)	0.0523 (9)
O4	0.4608 (5)	0.14368 (10)	0.71859 (19)	0.0296 (6)
O5	0.1917 (5)	0.21376 (10)	0.7854 (2)	0.0339 (6)
O6	0.5748 (6)	0.18540 (13)	0.8852 (2)	0.0453 (8)
C1	−0.2103 (7)	0.14519 (14)	0.2887 (3)	0.0246 (7)
C2	−0.2856 (7)	0.10442 (14)	0.3545 (3)	0.0243 (7)
C3	−0.1645 (7)	0.09387 (13)	0.4487 (3)	0.0260 (7)
H3	−0.2168	0.0658	0.4910	0.031*
C4	0.0403 (7)	0.12493 (13)	0.4835 (3)	0.0247 (7)
C5	0.1600 (7)	0.11762 (14)	0.5845 (3)	0.0264 (8)
H5	0.1130	0.0900	0.6292	0.032*
C6	0.3434 (7)	0.15073 (14)	0.6165 (3)	0.0260 (8)
C7	0.4289 (7)	0.19063 (13)	0.5502 (3)	0.0247 (7)
C8	0.3173 (7)	0.19787 (14)	0.4520 (3)	0.0263 (7)
H8	0.3742	0.2245	0.4068	0.032*
C9	0.1171 (7)	0.16576 (13)	0.4172 (3)	0.0239 (7)
C10	−0.0091 (7)	0.17479 (14)	0.3192 (3)	0.0249 (7)
H10	0.0457	0.2016	0.2740	0.030*
C11	−0.6552 (9)	0.02223 (16)	0.1672 (3)	0.0374 (9)
C12	0.1767 (9)	0.12624 (16)	0.8865 (3)	0.0376 (9)

	U11	U22	U33	U12	U13	U23
Br1	0.0434 (2)	0.0326 (2)	0.0258 (2)	0.00171 (17)	−0.00934 (16)	0.00457 (15)
Br2	0.0305 (2)	0.0321 (2)	0.0343 (2)	−0.00321 (15)	0.00105 (15)	−0.00809 (15)
S1	0.0307 (5)	0.0236 (5)	0.0348 (5)	−0.0030 (4)	−0.0049 (4)	0.0053 (4)
S2	0.0322 (5)	0.0296 (5)	0.0239 (4)	0.0006 (4)	−0.0044 (4)	−0.0032 (4)
F1	0.0710 (19)	0.0505 (17)	0.0342 (14)	−0.0086 (14)	0.0094 (13)	−0.0054 (12)
F2	0.0517 (16)	0.0439 (15)	0.0501 (15)	0.0067 (12)	−0.0195 (12)	0.0014 (12)
F3	0.072 (2)	0.0351 (15)	0.0652 (18)	−0.0132 (14)	−0.0185 (15)	−0.0114 (13)
F4	0.0533 (16)	0.0500 (17)	0.0472 (15)	−0.0194 (13)	0.0033 (12)	−0.0053 (12)
F5	0.083 (2)	0.0451 (17)	0.0623 (18)	0.0213 (15)	0.0097 (16)	0.0221 (14)
F6	0.0611 (17)	0.0595 (18)	0.0313 (13)	−0.0012 (14)	0.0112 (12)	−0.0017 (12)
O1	0.0299 (13)	0.0263 (14)	0.0321 (14)	0.0015 (11)	−0.0038 (11)	−0.0013 (11)
O2	0.0354 (16)	0.0268 (15)	0.068 (2)	0.0047 (12)	−0.0101 (14)	−0.0043 (14)
O3	0.0495 (19)	0.056 (2)	0.0515 (19)	−0.0178 (16)	−0.0005 (15)	0.0233 (16)
O4	0.0347 (14)	0.0324 (15)	0.0218 (12)	0.0063 (11)	−0.0046 (10)	−0.0033 (10)
O5	0.0431 (16)	0.0275 (14)	0.0312 (14)	0.0057 (12)	−0.0002 (12)	−0.0021 (11)
O6	0.0403 (16)	0.059 (2)	0.0362 (16)	0.0000 (15)	−0.0135 (13)	−0.0151 (14)
C1	0.0309 (19)	0.0239 (18)	0.0191 (16)	0.0057 (15)	0.0018 (14)	−0.0001 (13)
C2	0.0241 (17)	0.0225 (18)	0.0263 (18)	0.0016 (14)	0.0020 (14)	−0.0025 (14)
C3	0.036 (2)	0.0194 (17)	0.0228 (17)	0.0014 (15)	0.0035 (14)	0.0012 (13)
C4	0.0329 (19)	0.0198 (17)	0.0213 (17)	0.0040 (15)	0.0016 (14)	−0.0008 (13)
C5	0.036 (2)	0.0210 (18)	0.0219 (17)	0.0040 (15)	−0.0018 (14)	0.0002 (14)
C6	0.0307 (19)	0.030 (2)	0.0176 (16)	0.0070 (15)	−0.0020 (14)	−0.0015 (14)
C7	0.0259 (17)	0.0194 (17)	0.0289 (18)	0.0007 (14)	−0.0002 (14)	−0.0055 (14)
C8	0.0316 (19)	0.0209 (18)	0.0265 (18)	0.0026 (15)	0.0050 (14)	−0.0013 (14)
C9	0.0311 (19)	0.0171 (17)	0.0237 (17)	0.0053 (14)	0.0026 (14)	−0.0026 (13)
C10	0.0321 (19)	0.0227 (18)	0.0200 (16)	0.0053 (15)	0.0042 (14)	0.0018 (13)
C11	0.044 (2)	0.028 (2)	0.040 (2)	−0.0033 (18)	−0.0039 (19)	−0.0027 (17)
C12	0.048 (2)	0.034 (2)	0.031 (2)	0.0055 (19)	0.0030 (18)	0.0018 (17)

Br1—C1	1.886 (3)	O4—C6	1.421 (4)
Br2—C7	1.887 (3)	C1—C10	1.367 (5)
S1—O3	1.405 (3)	C1—C2	1.410 (5)
S1—O2	1.409 (3)	C2—C3	1.359 (5)
S1—O1	1.573 (3)	C3—C4	1.418 (5)
S1—C11	1.841 (4)	C3—H3	0.9500
S2—O6	1.410 (3)	C4—C5	1.415 (5)
S2—O5	1.414 (3)	C4—C9	1.417 (5)
S2—O4	1.584 (3)	C5—C6	1.359 (5)
S2—C12	1.835 (5)	C5—H5	0.9500
F1—C11	1.317 (5)	C6—C7	1.412 (5)
F2—C11	1.311 (5)	C7—C8	1.366 (5)
F3—C11	1.314 (5)	C8—C9	1.417 (5)
F4—C12	1.313 (5)	C8—H8	0.9500
F5—C12	1.315 (5)	C9—C10	1.405 (5)
F6—C12	1.321 (5)	C10—H10	0.9500
O1—C2	1.414 (4)
O3—S1—O2	122.2 (2)	C4—C5—H5	120.6
O3—S1—O1	107.7 (2)	C5—C6—C7	122.4 (3)
O2—S1—O1	111.60 (16)	C5—C6—O4	118.7 (3)
O3—S1—C11	106.5 (2)	C7—C6—O4	118.8 (3)
O2—S1—C11	108.3 (2)	C8—C7—C6	119.3 (3)
O1—S1—C11	97.59 (16)	C8—C7—Br2	120.8 (3)
O6—S2—O5	122.32 (19)	C6—C7—Br2	119.8 (3)
O6—S2—O4	107.69 (17)	C7—C8—C9	120.2 (3)
O5—S2—O4	111.13 (15)	C7—C8—H8	119.9
O6—S2—C12	106.2 (2)	C9—C8—H8	119.9
O5—S2—C12	107.73 (19)	C10—C9—C8	120.6 (3)
O4—S2—C12	99.18 (17)	C10—C9—C4	120.0 (3)
C2—O1—S1	123.3 (2)	C8—C9—C4	119.4 (3)
C6—O4—S2	119.3 (2)	C1—C10—C9	120.3 (3)
C10—C1—C2	119.6 (3)	C1—C10—H10	119.8
C10—C1—Br1	120.1 (3)	C9—C10—H10	119.8
C2—C1—Br1	120.4 (3)	F3—C11—F2	109.8 (4)
C3—C2—C1	121.7 (3)	F3—C11—F1	109.2 (4)
C3—C2—O1	120.2 (3)	F2—C11—F1	109.7 (4)
C1—C2—O1	117.7 (3)	F3—C11—S1	108.1 (3)
C2—C3—C4	119.6 (3)	F2—C11—S1	111.0 (3)
C2—C3—H3	120.2	F1—C11—S1	109.0 (3)
C4—C3—H3	120.2	F4—C12—F5	109.7 (4)
C5—C4—C9	119.6 (3)	F4—C12—F6	109.5 (4)
C5—C4—C3	121.6 (3)	F5—C12—F6	108.9 (3)
C9—C4—C3	118.7 (3)	F4—C12—S2	110.0 (3)
C6—C5—C4	118.9 (3)	F5—C12—S2	110.2 (3)
C6—C5—H5	120.6	F6—C12—S2	108.4 (3)
O3—S1—O1—C2	125.8 (3)	C7—C8—C9—C10	176.1 (3)
O2—S1—O1—C2	−10.9 (3)	C7—C8—C9—C4	−2.4 (5)
C11—S1—O1—C2	−124.1 (3)	C5—C4—C9—C10	−176.9 (3)
O6—S2—O4—C6	−146.3 (3)	C3—C4—C9—C10	0.0 (5)
O5—S2—O4—C6	−9.9 (3)	C5—C4—C9—C8	1.7 (5)
C12—S2—O4—C6	103.3 (3)	C3—C4—C9—C8	178.5 (3)
C10—C1—C2—C3	0.6 (6)	C2—C1—C10—C9	−2.1 (5)
Br1—C1—C2—C3	−179.1 (3)	Br1—C1—C10—C9	177.7 (3)
C10—C1—C2—O1	173.5 (3)	C8—C9—C10—C1	−176.8 (3)
Br1—C1—C2—O1	−6.2 (4)	C4—C9—C10—C1	1.8 (5)
S1—O1—C2—C3	−63.9 (4)	O3—S1—C11—F3	−53.1 (4)
S1—O1—C2—C1	123.0 (3)	O2—S1—C11—F3	80.0 (3)
C1—C2—C3—C4	1.1 (5)	O1—S1—C11—F3	−164.2 (3)
O1—C2—C3—C4	−171.6 (3)	O3—S1—C11—F2	67.4 (4)
C2—C3—C4—C5	175.4 (3)	O2—S1—C11—F2	−159.5 (3)
C2—C3—C4—C9	−1.4 (5)	O1—S1—C11—F2	−43.7 (3)
C9—C4—C5—C6	1.2 (5)	O3—S1—C11—F1	−171.6 (3)
C3—C4—C5—C6	−175.5 (3)	O2—S1—C11—F1	−38.5 (3)
C4—C5—C6—C7	−3.5 (5)	O1—S1—C11—F1	77.3 (3)
C4—C5—C6—O4	179.2 (3)	O6—S2—C12—F4	−176.0 (3)
S2—O4—C6—C5	−97.9 (4)	O5—S2—C12—F4	51.3 (3)
S2—O4—C6—C7	84.7 (4)	O4—S2—C12—F4	−64.5 (3)
C5—C6—C7—C8	2.8 (6)	O6—S2—C12—F5	−55.0 (3)
O4—C6—C7—C8	−179.9 (3)	O5—S2—C12—F5	172.4 (3)
C5—C6—C7—Br2	−176.1 (3)	O4—S2—C12—F5	56.6 (3)
O4—C6—C7—Br2	1.2 (4)	O6—S2—C12—F6	64.2 (3)
C6—C7—C8—C9	0.3 (5)	O5—S2—C12—F6	−68.5 (3)
Br2—C7—C8—C9	179.2 (3)	O4—S2—C12—F6	175.8 (3)