1-Fluoro-3,3-dimethyl-1,3-dihydro-1λ(3)-benzo[d][1,2]iodoxole.

The asymmetric unit of the title compound, C(9)H(10)FIO, contains two independent mol-ecules which are weakly bound by inter-molecular O⋯I inter-actions [3.046 (4) and 2.947 (4) Å]. The two covalent I-F bonds are slightly longer than the two I-O bonds.

Related literature

For information on the chemistry of hypervalent compounds, see: Zhdankin & Stang (2002 ▶); Wirth (2005 ▶). For the synthesis and structural analysis of the bromo analog of the title compound, see: Braddock et al. (2006 ▶). For the synthesis and structural analysis of the chloro analog of the title compound, see: Amey & Martin (1979 ▶); Niedermann et al. (2010 ▶). For related information on the trans effect in hypervalent iodine compounds, see: Ochiai et al. (2006 ▶).

Experimental

Crystal data

C9H10FIO

M = 280.07

Triclinic,

a = 7.983 (6) Å

b = 10.188 (8) Å

c = 11.691 (5) Å

α = 83.13 (5)°

β = 79.01 (5)°

γ = 78.27 (6)°

V = 910.6 (11) Å3

Z = 4

Mo Kα radiation

μ = 3.48 mm−1

T = 193 K

0.4 × 0.4 × 0.3 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (NRCVAX; Gabe et al., 1989 ▶] T min = 0.337, T max = 0.422

3408 measured reflections

3408 independent reflections

2833 reflections with I > 2σ(I)

1 standard reflections every 100 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.073

S = 1.05

3408 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −1.22 e Å−3

Data collection: DIFRAC (Flack et al., 1992 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812012822/lh5436sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812012822/lh5436Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012822/lh5436Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812012822/lh5436Isup4.cml

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

C9H10FIO	Z = 4
Mr = 280.07	F(000) = 536
Triclinic, P1	Dx = 2.043 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.983 (6) Å	Cell parameters from 20 reflections
b = 10.188 (8) Å	θ = 10–12.5°
c = 11.691 (5) Å	µ = 3.48 mm−1
α = 83.13 (5)°	T = 193 K
β = 79.01 (5)°	Prism, white
γ = 78.27 (6)°	0.4 × 0.4 × 0.3 mm
V = 910.6 (11) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0
Graphite monochromator	θmax = 25.6°, θmin = 1.8°
ω scans	h = −9→9
Absorption correction: ψ scan (NRCVAX; Gabe et al., 1989]	k = 0→12
Tmin = 0.337, Tmax = 0.422	l = −13→14
3408 measured reflections	1 standard reflections every 100 reflections
3408 independent reflections	intensity decay: none
2833 reflections with I > 2σ(I)

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0443P)2 + 0.462P] where P = (Fo2 + 2Fc2)/3
3408 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −1.22 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.

Refinement. The DIFRAC(Flack, 1992) program was used for centering, indexing, and data collection. One standard reflection was measured every 100 reflections, no decay was observed during data collection. The data were corrected for absorption by empirical methods based on psi scans and reduced with the NRCVAX (Gabe, 1989) programs. They were solved using SHELXS97(Sheldrick, 2008) and refined by full-matrix least squares on F2 with SHELXL97(Sheldrick, 2008). The non-hydrogen atoms were refined anisotropically. 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
C1	0.5725 (6)	0.6621 (4)	0.4130 (4)	0.0211 (9)
C2	0.7221 (6)	0.5801 (5)	0.4421 (4)	0.0272 (10)
H2	0.8038	0.5305	0.3853	0.033*
C3	0.7484 (7)	0.5727 (5)	0.5550 (5)	0.0339 (12)
H3	0.849	0.5164	0.5777	0.041*
C4	0.6295 (6)	0.6467 (5)	0.6364 (4)	0.0288 (11)
H4	0.6489	0.6399	0.7148	0.035*
C5	0.4833 (6)	0.7300 (5)	0.6056 (4)	0.0270 (10)
H5	0.4045	0.7827	0.6617	0.032*
C6	0.4513 (6)	0.7368 (4)	0.4917 (4)	0.0227 (9)
C7	0.2966 (6)	0.8263 (4)	0.4478 (4)	0.0227 (9)
C8	0.3279 (7)	0.9700 (5)	0.4218 (4)	0.0299 (11)
H8A	0.2272	1.0273	0.3935	0.045*
H8B	0.4316	0.9723	0.3618	0.045*
H8C	0.3451	1.0031	0.4933	0.045*
C9	0.1276 (6)	0.8183 (5)	0.5324 (4)	0.0309 (11)
H9A	0.0311	0.8776	0.5008	0.046*
H9B	0.1353	0.8467	0.6081	0.046*
H9C	0.1077	0.7255	0.5426	0.046*
C10	−0.0885 (6)	0.8468 (4)	0.0402 (4)	0.0215 (9)
C11	−0.2429 (6)	0.9114 (5)	0.0057 (5)	0.0320 (12)
H11	−0.3264	0.9704	0.0542	0.038*
C12	−0.2712 (6)	0.8866 (5)	−0.1023 (5)	0.0308 (11)
H12	−0.3758	0.9292	−0.1291	0.037*
C13	−0.1484 (6)	0.8006 (5)	−0.1711 (4)	0.0302 (11)
H13	−0.1687	0.7844	−0.2452	0.036*
C14	0.0050 (6)	0.7373 (4)	−0.1332 (4)	0.0245 (10)
H14	0.0887	0.678	−0.1814	0.029*
C15	0.0367 (6)	0.7600 (4)	−0.0255 (4)	0.0212 (9)
C16	0.1966 (6)	0.6918 (4)	0.0259 (4)	0.0204 (9)
C17	0.3625 (6)	0.6881 (5)	−0.0644 (4)	0.0267 (10)
H17A	0.4625	0.6434	−0.0281	0.04*
H17B	0.3763	0.7802	−0.0937	0.04*
H17C	0.3554	0.6384	−0.1296	0.04*
C18	0.1750 (6)	0.5513 (4)	0.0787 (4)	0.0274 (10)
H18A	0.2784	0.5075	0.1118	0.041*
H18B	0.1601	0.4985	0.0178	0.041*
H18C	0.0726	0.5574	0.1406	0.041*
F1	0.7418 (4)	0.5802 (3)	0.1913 (3)	0.0372 (7)
F2	−0.2633 (4)	0.9676 (3)	0.2491 (3)	0.0437 (8)
I1	0.50006 (4)	0.68702 (3)	0.24847 (2)	0.02221 (10)
I2	−0.01657 (4)	0.86419 (3)	0.20011 (2)	0.02531 (10)
O1	0.2750 (4)	0.7761 (3)	0.3428 (3)	0.0283 (7)
O2	0.2131 (4)	0.7722 (3)	0.1146 (3)	0.0250 (7)

	U11	U22	U33	U12	U13	U23
C1	0.025 (2)	0.018 (2)	0.022 (2)	−0.0066 (18)	−0.0071 (18)	0.0021 (17)
C2	0.022 (2)	0.027 (2)	0.031 (3)	0.000 (2)	−0.004 (2)	−0.0025 (19)
C3	0.031 (3)	0.032 (3)	0.041 (3)	−0.005 (2)	−0.018 (2)	0.005 (2)
C4	0.037 (3)	0.030 (3)	0.023 (2)	−0.010 (2)	−0.015 (2)	0.0036 (19)
C5	0.038 (3)	0.027 (2)	0.018 (2)	−0.012 (2)	−0.005 (2)	−0.0010 (18)
C6	0.024 (2)	0.020 (2)	0.024 (2)	−0.0023 (18)	−0.0066 (19)	0.0019 (17)
C7	0.022 (2)	0.025 (2)	0.020 (2)	−0.0004 (18)	−0.0024 (18)	−0.0050 (18)
C8	0.036 (3)	0.024 (2)	0.026 (2)	0.000 (2)	−0.003 (2)	0.0009 (19)
C9	0.027 (3)	0.034 (3)	0.027 (3)	−0.002 (2)	0.005 (2)	−0.003 (2)
C10	0.020 (2)	0.022 (2)	0.021 (2)	−0.0058 (18)	0.0004 (18)	−0.0009 (17)
C11	0.021 (2)	0.025 (2)	0.045 (3)	−0.001 (2)	0.000 (2)	0.002 (2)
C12	0.021 (2)	0.032 (3)	0.040 (3)	−0.007 (2)	−0.012 (2)	0.008 (2)
C13	0.033 (3)	0.027 (2)	0.034 (3)	−0.013 (2)	−0.012 (2)	0.007 (2)
C14	0.032 (3)	0.023 (2)	0.021 (2)	−0.009 (2)	−0.0069 (19)	−0.0009 (18)
C15	0.022 (2)	0.018 (2)	0.024 (2)	−0.0076 (18)	−0.0021 (18)	0.0011 (17)
C16	0.017 (2)	0.024 (2)	0.018 (2)	−0.0022 (18)	0.0009 (17)	−0.0054 (17)
C17	0.025 (2)	0.029 (2)	0.024 (2)	−0.002 (2)	−0.0009 (19)	−0.0056 (19)
C18	0.030 (3)	0.024 (2)	0.027 (2)	−0.002 (2)	−0.007 (2)	−0.0010 (19)
F1	0.0276 (16)	0.0464 (18)	0.0335 (16)	0.0017 (13)	0.0032 (13)	−0.0155 (13)
F2	0.0304 (17)	0.0502 (19)	0.0433 (18)	0.0012 (14)	0.0115 (14)	−0.0189 (15)
I1	0.02218 (17)	0.02611 (17)	0.01820 (16)	−0.00355 (12)	−0.00138 (12)	−0.00623 (11)
I2	0.02468 (18)	0.02723 (17)	0.02327 (17)	−0.00611 (13)	0.00320 (12)	−0.00869 (12)
O1	0.0204 (17)	0.0395 (19)	0.0243 (17)	0.0040 (14)	−0.0070 (14)	−0.0113 (14)
O2	0.0195 (16)	0.0316 (17)	0.0235 (16)	−0.0007 (13)	−0.0009 (13)	−0.0122 (14)

C1—C6	1.374 (6)	C10—I2	2.094 (5)
C1—C2	1.386 (6)	C11—H11	0.950
C1—I1	2.085 (4)	C11—C12	1.385 (7)
C2—C3	1.367 (7)	C12—C13	1.377 (7)
C2—H2	0.950	C13—C14	1.389 (7)
C3—C4	1.382 (7)	C14—C15	1.385 (6)
C4—C5	1.378 (7)	C15—C16	1.519 (6)
C5—C6	1.394 (6)	C16—O2	1.437 (5)
C6—C7	1.514 (6)	C16—C18	1.519 (6)
C7—O1	1.437 (5)	C16—C17	1.525 (6)
C7—C8	1.521 (6)	F1—I1	2.045 (3)
C7—C9	1.523 (6)	F2—I2	2.046 (3)
C10—C15	1.372 (6)	I1—O1	2.022 (3)
C10—C11	1.382 (6)	I2—O2	2.017 (3)
C6—C1—C2	123.2 (4)	H11—C11—C10	121.3
C6—C1—I1	111.5 (3)	C13—C12—C11	120.3 (5)
C2—C1—I1	125.3 (4)	C12—C13—C14	120.6 (5)
C3—C2—C1	117.9 (5)	C15—C14—C13	120.4 (4)
H2—C2—C1	121.0	C10—C15—C14	117.3 (4)
C2—C3—C4	120.4 (5)	C10—C15—C16	118.2 (4)
C5—C4—C3	120.9 (4)	C14—C15—C16	124.5 (4)
C4—C5—C6	119.7 (5)	O2—C16—C15	107.5 (3)
C1—C6—C5	117.7 (4)	O2—C16—C18	110.3 (4)
C1—C6—C7	118.1 (4)	C15—C16—C18	109.6 (4)
C5—C6—C7	124.2 (4)	O2—C16—C17	106.0 (3)
O1—C7—C6	108.1 (4)	C15—C16—C17	111.9 (4)
O1—C7—C8	109.8 (4)	C18—C16—C17	111.3 (4)
C6—C7—C8	109.9 (4)	O1—I1—F1	166.40 (12)
O1—C7—C9	104.8 (4)	O1—I1—C1	80.58 (16)
C6—C7—C9	112.1 (4)	F1—I1—C1	86.21 (16)
C8—C7—C9	111.8 (4)	O2—I2—F2	166.81 (13)
C15—C10—C11	124.0 (4)	O2—I2—C10	80.30 (16)
C15—C10—I2	111.0 (3)	F2—I2—C10	87.13 (16)
C11—C10—I2	124.9 (4)	C7—O1—I1	113.7 (3)
C10—C11—C12	117.4 (5)	C16—O2—I2	113.6 (3)
C6—C1—C2—C3	0.7 (7)	C13—C14—C15—C10	−0.2 (6)
I1—C1—C2—C3	−178.5 (4)	C13—C14—C15—C16	177.5 (4)
C1—C2—C3—C4	−0.8 (7)	C10—C15—C16—O2	−22.0 (5)
C2—C3—C4—C5	−0.6 (8)	C14—C15—C16—O2	160.3 (4)
C3—C4—C5—C6	2.1 (7)	C10—C15—C16—C18	97.9 (5)
C2—C1—C6—C5	0.8 (7)	C14—C15—C16—C18	−79.8 (5)
I1—C1—C6—C5	−179.8 (3)	C10—C15—C16—C17	−138.1 (4)
C2—C1—C6—C7	177.8 (4)	C14—C15—C16—C17	44.3 (6)
I1—C1—C6—C7	−2.8 (5)	C6—C1—I1—O1	−11.4 (3)
C4—C5—C6—C1	−2.2 (7)	C2—C1—I1—O1	168.0 (4)
C4—C5—C6—C7	−179.0 (4)	C6—C1—I1—F1	171.9 (3)
C1—C6—C7—O1	21.8 (5)	C2—C1—I1—F1	−8.8 (4)
C5—C6—C7—O1	−161.3 (4)	C15—C10—I2—O2	13.5 (3)
C1—C6—C7—C8	−98.0 (5)	C11—C10—I2—O2	−167.8 (4)
C5—C6—C7—C8	78.8 (5)	C15—C10—I2—F2	−170.5 (3)
C1—C6—C7—C9	136.9 (4)	C11—C10—I2—F2	8.2 (4)
C5—C6—C7—C9	−46.3 (6)	C6—C7—O1—I1	−31.0 (4)
C15—C10—C11—C12	−0.3 (7)	C8—C7—O1—I1	89.0 (4)
I2—C10—C11—C12	−178.8 (3)	C9—C7—O1—I1	−150.7 (3)
C10—C11—C12—C13	0.0 (7)	F1—I1—O1—C7	38.2 (7)
C11—C12—C13—C14	0.2 (7)	C1—I1—O1—C7	24.4 (3)
C12—C13—C14—C15	−0.1 (7)	C15—C16—O2—I2	33.1 (4)
C11—C10—C15—C14	0.4 (6)	C18—C16—O2—I2	−86.4 (4)
I2—C10—C15—C14	179.0 (3)	C17—C16—O2—I2	153.0 (3)
C11—C10—C15—C16	−177.4 (4)	F2—I2—O2—C16	−44.7 (7)
I2—C10—C15—C16	1.2 (5)	C10—I2—O2—C16	−26.9 (3)

Table 1

Selected bond lengths (Å)

C1—I1	2.085 (4)
C10—I2	2.094 (5)
F1—I1	2.045 (3)
F2—I2	2.046 (3)
I1—O1	2.022 (3)
I2—O2	2.017 (3)