Literature DB >> 26594456

Crystal structure of 1-fluoro-1,3-di-hydro-benzo[c]thio-phene 2,2-dioxide.

Ying Zou¹, Zibin Qiu¹, Renming Tang¹, Kaixu Yuan¹, Ya Li¹.

Abstract

In the title compound, C8H7FO2S, the thio-phene ring has an envelope conformation, with the S atom bearing the two O atoms being the flap. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯F inter-actions, generating a three-dimensional network structure.

Entities: Chemical Disease Gene

Keywords: C—H⋯O and C—H⋯F interactions; crystal structure; dihydrobenzothiophene; fluorine; sulfone

Year: 2015 PMID： 26594456 PMCID： PMC4647347 DOI： 10.1107/S2056989015016357

Source DB: PubMed Journal: Acta Crystallogr E Crystallogr Commun

Related literature

For the use of of α-fluoro sulfones in organic synthesis, see: Fukuzumi et al. (2006 ▸); Li et al. (2006 ▸); Prakash et al. (2003 ▸); Zhao et al. (2013 ▸). For their synthesis, see: Jiang et al. (2014 ▸); Ni et al. (2008 ▸).

Experimental

Crystal data

C8H7FO2S M = 186.20 Monoclinic, a = 5.7772 (5) Å b = 8.3886 (6) Å c = 16.8717 (12) Å β = 99.742 (6)° V = 805.86 (11) Å3 Z = 4 Cu Kα radiation μ = 3.38 mm−1 T = 296 K 0.05 × 0.03 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.418, T max = 0.753 6724 measured reflections 1475 independent reflections 1206 reflections with I > 2σ(I) R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.068 wR(F 2) = 0.205 S = 1.13 1475 reflections 109 parameters H-atom parameters constrained Δρmax = 0.58 e Å−3 Δρmin = −0.98 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▸) and Mercury (Macrae, 2006 ▸); software used to prepare material for publication: OLEX2. Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015016357/wm5205sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015016357/wm5205Isup2.hkl Supporting information file. DOI: 10.1107/S2056989015016357/wm5205Isup3.pdf Supporting information file. DOI: 10.1107/S2056989015016357/wm5205Isup4.pdf Supporting information file. DOI: 10.1107/S2056989015016357/wm5205Isup5.pdf Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989015016357/wm5205Isup6.cml Click here for additional data file. . DOI: 10.1107/S2056989015016357/wm5205fig1.tif Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Click here for additional data file. . DOI: 10.1107/S2056989015016357/wm5205fig2.tif Packing of the molecules in the unit cell in a view approximately along [010]. CCDC reference: 1421889 Additional supporting information: crystallographic information; 3D view; checkCIF report

C₈H₇FO₂S	F(000) = 384
M_r = 186.20	D_x = 1.535 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 5.7772 (5) Å	Cell parameters from 1262 reflections
b = 8.3886 (6) Å	θ = 5.3–66.3°
c = 16.8717 (12) Å	µ = 3.38 mm⁻¹
β = 99.742 (6)°	T = 296 K
V = 805.86 (11) Å³	Block, colourless
Z = 4	0.05 × 0.03 × 0.02 mm

Bruker APEXII CCD diffractometer	1206 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
φ and ω scans	θ_max = 69.6°, θ_min = 5.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→6
T_min = 0.418, T_max = 0.753	k = −10→9
6724 measured reflections	l = −19→17
1475 independent reflections

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.068	H-atom parameters constrained
wR(F²) = 0.205	w = 1/[σ²(F_o²) + (0.1242P)² + 0.3031P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max < 0.001
1475 reflections	Δρ_max = 0.58 e Å⁻³
109 parameters	Δρ_min = −0.98 e Å⁻³
0 restraints

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	U_iso*/U_eq
S1	0.58177 (16)	0.76462 (12)	0.95887 (5)	0.0438 (4)
F1	0.1554 (5)	0.6784 (4)	0.96561 (16)	0.0686 (8)
O1	0.6976 (5)	0.9083 (4)	0.94354 (18)	0.0593 (9)
O2	0.6325 (6)	0.6952 (5)	1.03759 (17)	0.0675 (10)
C1	0.2672 (7)	0.7960 (5)	0.9290 (2)	0.0442 (9)
H1	0.2194	0.9030	0.9431	0.053*
C2	0.2387 (7)	0.7727 (4)	0.8397 (2)	0.0381 (8)
C3	0.0537 (8)	0.8364 (5)	0.7852 (3)	0.0521 (10)
H3	−0.0632	0.8964	0.8027	0.063*
C4	0.0492 (10)	0.8075 (6)	0.7037 (3)	0.0633 (13)
H4	−0.0734	0.8477	0.6661	0.076*
C5	0.2237 (10)	0.7203 (6)	0.6781 (3)	0.0638 (13)
H5	0.2178	0.7029	0.6233	0.077*
C6	0.4093 (8)	0.6576 (5)	0.7325 (2)	0.0512 (10)
H6	0.5276	0.5994	0.7147	0.061*
C7	0.4136 (6)	0.6840 (4)	0.8142 (2)	0.0373 (8)
C8	0.6028 (7)	0.6252 (5)	0.8808 (2)	0.0442 (9)
H8A	0.7564	0.6286	0.8649	0.053*
H8B	0.5711	0.5175	0.8969	0.053*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0448 (6)	0.0535 (7)	0.0294 (6)	−0.0075 (4)	−0.0046 (4)	−0.0040 (3)
F1	0.0590 (15)	0.098 (2)	0.0493 (15)	−0.0118 (15)	0.0102 (11)	0.0065 (13)
O1	0.0623 (18)	0.0629 (19)	0.0519 (16)	−0.0229 (15)	0.0075 (13)	−0.0147 (14)
O2	0.068 (2)	0.095 (2)	0.0328 (16)	−0.0078 (18)	−0.0109 (14)	0.0109 (15)
C1	0.047 (2)	0.054 (2)	0.0302 (19)	−0.0005 (17)	0.0026 (14)	−0.0082 (15)
C2	0.045 (2)	0.0384 (19)	0.0283 (18)	−0.0040 (15)	−0.0003 (14)	−0.0037 (13)
C3	0.053 (2)	0.051 (2)	0.047 (2)	0.0017 (18)	−0.0075 (17)	0.0000 (17)
C4	0.078 (3)	0.063 (3)	0.038 (2)	−0.013 (2)	−0.019 (2)	0.0103 (19)
C5	0.092 (4)	0.069 (3)	0.027 (2)	−0.021 (3)	−0.001 (2)	−0.0043 (18)
C6	0.068 (3)	0.052 (2)	0.0358 (19)	−0.0143 (19)	0.0140 (17)	−0.0135 (16)
C7	0.0453 (19)	0.0335 (18)	0.0313 (17)	−0.0072 (14)	0.0011 (14)	−0.0070 (13)
C8	0.0427 (19)	0.043 (2)	0.045 (2)	0.0018 (16)	0.0020 (15)	−0.0037 (16)

S1—O1	1.423 (3)	C3—C4	1.392 (6)
S1—O2	1.434 (3)	C4—H4	0.9300
S1—C1	1.821 (4)	C4—C5	1.373 (8)
S1—C8	1.781 (4)	C5—H5	0.9300
F1—C1	1.381 (5)	C5—C6	1.391 (7)
C1—H1	0.9800	C6—H6	0.9300
C1—C2	1.502 (5)	C6—C7	1.392 (5)
C2—C3	1.393 (5)	C7—C8	1.512 (5)
C2—C7	1.381 (5)	C8—H8A	0.9700
C3—H3	0.9300	C8—H8B	0.9700

O1—S1—O2	118.9 (2)	C3—C4—H4	119.6
O1—S1—C1	107.8 (2)	C5—C4—C3	120.7 (4)
O1—S1—C8	109.19 (19)	C5—C4—H4	119.6
O2—S1—C1	110.6 (2)	C4—C5—H5	119.4
O2—S1—C8	112.9 (2)	C4—C5—C6	121.3 (4)
C8—S1—C1	94.61 (18)	C6—C5—H5	119.4
S1—C1—H1	112.0	C5—C6—H6	120.8
F1—C1—S1	107.1 (3)	C5—C6—C7	118.4 (4)
F1—C1—H1	112.0	C7—C6—H6	120.8
F1—C1—C2	112.1 (3)	C2—C7—C6	120.2 (4)
C2—C1—S1	101.1 (3)	C2—C7—C8	114.8 (3)
C2—C1—H1	112.0	C6—C7—C8	125.0 (4)
C3—C2—C1	123.6 (4)	S1—C8—H8A	111.4
C7—C2—C1	114.9 (3)	S1—C8—H8B	111.4
C7—C2—C3	121.4 (4)	C7—C8—S1	101.8 (2)
C2—C3—H3	121.0	C7—C8—H8A	111.4
C4—C3—C2	118.0 (4)	C7—C8—H8B	111.4
C4—C3—H3	121.0	H8A—C8—H8B	109.3

S1—C1—C2—C3	−156.5 (3)	C1—C2—C7—C8	0.2 (5)
S1—C1—C2—C7	22.5 (4)	C2—C3—C4—C5	−0.7 (7)
F1—C1—C2—C3	89.7 (5)	C2—C7—C8—S1	−23.5 (4)
F1—C1—C2—C7	−91.2 (4)	C3—C2—C7—C6	0.7 (6)
O1—S1—C1—F1	−162.2 (2)	C3—C2—C7—C8	179.3 (4)
O1—S1—C1—C2	80.4 (3)	C3—C4—C5—C6	0.3 (8)
O1—S1—C8—C7	−79.0 (3)	C4—C5—C6—C7	0.6 (7)
O2—S1—C1—F1	−30.6 (3)	C5—C6—C7—C2	−1.0 (6)
O2—S1—C1—C2	−148.1 (3)	C5—C6—C7—C8	−179.6 (4)
O2—S1—C8—C7	146.3 (3)	C6—C7—C8—S1	155.1 (3)
C1—S1—C8—C7	31.6 (3)	C7—C2—C3—C4	0.2 (6)
C1—C2—C3—C4	179.3 (4)	C8—S1—C1—F1	86.0 (3)
C1—C2—C7—C6	−178.4 (3)	C8—S1—C1—C2	−31.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.95	3.687 (6)	138
C1—H1···O1ⁱⁱ	0.98	2.47	3.266 (5)	139
C1—H1···O2ⁱⁱ	0.98	3.48	4.331 (6)	147
C4—H4···O2ⁱⁱⁱ	0.93	2.54	3.371 (5)	148
C5—H5···F1^iv	0.93	2.81	3.640 (5)	150
C8—H8B···O2^v	0.97	2.50	3.406 (5)	156

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C3H3O1ⁱ	0.93	2.95	3.687(6)	138
C1H1O1ⁱⁱ	0.98	2.47	3.266(5)	139
C1H1O2ⁱⁱ	0.98	3.48	4.331(6)	147
C4H4O2ⁱⁱⁱ	0.93	2.54	3.371(5)	148
C5H5F1^iv	0.93	2.81	3.640(5)	150
C8H8BO2^v	0.97	2.50	3.406(5)	156

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

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