5-Chloro-3-methyl­sulfinyl-2-phenyl-1-benzofuran

The title compound, C₁₅H₁₁ClO₂S, was prepared by the oxidation of 5-chloro-3-methyl­sulfanyl-2-phenyl-1-benzofuran using 3-chloro­perbenzoic acid. The 1-benzofuran ring system is almost planar. The crystal structure is stabilized by weak aromatic π–π stacking and –CH₂—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.029
• wR factor = 0.078
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.65 mm
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl     ..  O2      ..       3.26 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.

5-Chloro-3-methylsulfinyl-2-phenyl-1-benzofuran

Crystal data

C15H11ClO2S	Z = 2
Mr = 290.75	F(000) = 300
Triclinic, P1	Dx = 1.488 Mg m^−3
Hall symbol: -p_1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1519 (5) Å	Cell parameters from 4954 reflections
b = 8.2258 (5) Å	θ = 2.7–28.3°
c = 10.6247 (6) Å	µ = 0.45 mm^−1
α = 91.195 (1)°	T = 173 K
β = 95.882 (1)°	Block, colourless
γ = 113.439 (1)°	0.65 × 0.43 × 0.25 mm
V = 648.74 (7) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	2484 independent reflections
Radiation source: fine-focus sealed tube	2373 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
Detector resolution: 10.00 pixels mm^-1	θmax = 26.0°, θmin = 1.9°
φ and ω scans	h = −10→10
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1999)	k = −10→10
Tmin = 0.792, Tmax = 0.895	l = −13→13
5026 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0358P)^2 + 0.3256P] where P = (Fo^2 + 2Fc^2)/3
2484 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S	0.20670 (5)	0.18486 (5)	0.09441 (3)	0.02258 (11)
Cl	0.79813 (5)	0.60605 (6)	0.51988 (3)	0.03201 (12)
O1	0.69955 (13)	0.34529 (14)	−0.00775 (10)	0.0231 (2)
O2	0.17903 (15)	0.32055 (15)	0.17488 (12)	0.0329 (3)
C1	0.43980 (19)	0.26649 (19)	0.07956 (13)	0.0205 (3)
C2	0.58546 (19)	0.37345 (19)	0.17477 (14)	0.0205 (3)
C3	0.5999 (2)	0.43216 (19)	0.30166 (14)	0.0225 (3)
H3	0.4990	0.4048	0.3443	0.027*
C4	0.7715 (2)	0.5329 (2)	0.36050 (14)	0.0237 (3)
C5	0.9265 (2)	0.5776 (2)	0.29882 (15)	0.0260 (3)
H5	1.0389	0.6461	0.3426	0.031*
C6	0.9130 (2)	0.5202 (2)	0.17334 (15)	0.0252 (3)
H6	1.0138	0.5484	0.1306	0.030*
C7	0.74121 (19)	0.41883 (19)	0.11499 (14)	0.0216 (3)
C8	0.51487 (19)	0.25412 (19)	−0.02768 (14)	0.0213 (3)
C9	0.44204 (19)	0.16598 (19)	−0.15405 (14)	0.0218 (3)
C10	0.2880 (2)	0.0077 (2)	−0.17214 (15)	0.0262 (3)
H10	0.2314	−0.0438	−0.1027	0.031*
C11	0.2186 (2)	−0.0733 (2)	−0.29283 (16)	0.0311 (4)
H11	0.1150	−0.1779	−0.3043	0.037*
C12	0.3042 (2)	0.0020 (2)	−0.39622 (16)	0.0332 (4)
H12	0.2576	−0.0519	−0.4772	0.040*
C13	0.4599 (2)	0.1583 (2)	−0.37933 (15)	0.0306 (3)
H13	0.5176	0.2072	−0.4490	0.037*
C14	0.5293 (2)	0.2411 (2)	−0.25942 (14)	0.0248 (3)
H14	0.6328	0.3458	−0.2485	0.030*
C15	0.1957 (2)	0.0090 (2)	0.19507 (18)	0.0356 (4)
H15A	0.0743	−0.0524	0.2139	0.053*
H15B	0.2741	0.0581	0.2725	0.053*
H15C	0.2327	−0.0726	0.1526	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.01645 (19)	0.0242 (2)	0.0261 (2)	0.00674 (14)	0.00386 (14)	0.00235 (14)
Cl	0.0309 (2)	0.0409 (2)	0.0215 (2)	0.01326 (17)	−0.00215 (15)	−0.00526 (15)
O1	0.0186 (5)	0.0267 (5)	0.0216 (5)	0.0063 (4)	0.0047 (4)	−0.0002 (4)
O2	0.0280 (6)	0.0284 (6)	0.0454 (7)	0.0123 (5)	0.0142 (5)	0.0008 (5)
C1	0.0178 (7)	0.0218 (7)	0.0208 (7)	0.0067 (5)	0.0029 (5)	0.0018 (5)
C2	0.0180 (7)	0.0203 (7)	0.0236 (7)	0.0078 (5)	0.0033 (5)	0.0029 (5)
C3	0.0216 (7)	0.0253 (7)	0.0221 (7)	0.0105 (6)	0.0045 (6)	0.0022 (6)
C4	0.0262 (8)	0.0251 (7)	0.0204 (7)	0.0115 (6)	0.0009 (6)	0.0000 (6)
C5	0.0198 (7)	0.0248 (7)	0.0298 (8)	0.0063 (6)	−0.0012 (6)	0.0006 (6)
C6	0.0188 (7)	0.0261 (8)	0.0290 (8)	0.0067 (6)	0.0056 (6)	0.0023 (6)
C7	0.0217 (7)	0.0229 (7)	0.0208 (7)	0.0094 (6)	0.0043 (6)	0.0022 (5)
C8	0.0184 (7)	0.0205 (7)	0.0240 (7)	0.0066 (6)	0.0035 (5)	0.0033 (5)
C9	0.0233 (7)	0.0233 (7)	0.0216 (7)	0.0121 (6)	0.0035 (6)	0.0009 (5)
C10	0.0273 (8)	0.0248 (8)	0.0258 (8)	0.0090 (6)	0.0052 (6)	0.0013 (6)
C11	0.0308 (8)	0.0263 (8)	0.0321 (8)	0.0083 (7)	0.0007 (7)	−0.0037 (6)
C12	0.0409 (9)	0.0356 (9)	0.0233 (8)	0.0168 (7)	−0.0007 (7)	−0.0057 (6)
C13	0.0377 (9)	0.0354 (9)	0.0220 (7)	0.0171 (7)	0.0070 (6)	0.0038 (6)
C14	0.0257 (7)	0.0254 (7)	0.0251 (7)	0.0114 (6)	0.0054 (6)	0.0034 (6)
C15	0.0312 (9)	0.0305 (9)	0.0477 (10)	0.0121 (7)	0.0147 (8)	0.0157 (7)

Geometric parameters (Å, º)

S—O2	1.493 (1)	C6—H6	0.9300
S—C1	1.771 (1)	C8—C9	1.461 (2)
S—C15	1.796 (2)	C9—C10	1.395 (2)
Cl—C4	1.748 (2)	C9—C14	1.408 (2)
O1—C7	1.377 (2)	C10—C11	1.387 (2)
O1—C8	1.380 (2	C10—H10	0.9300
C1—C8	1.368 (2)	C11—C12	1.385 (2)
C1—C2	1.447 (2)	C11—H11	0.9300
C2—C7	1.397 (2)	C12—C13	1.393 (2)
C2—C3	1.400 (2)	C12—H12	0.9300
C3—C4	1.383 (2)	C13—C14	1.384 (2)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.404 (2)	C14—H14	0.9300
C5—C6	1.384 (2)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—C7	1.383 (2)	C15—H15C	0.9600
O2—S—C1	107.06 (7)	C1—C8—C9	134.0 (1)
O2—S—C15	105.94 (8)	O1—C8—C9	115.5 (1)
C1—S—C15	97.64 (7)	C10—C9—C14	119.4 (1)
C7—O1—C8	106.7 (1)	C10—C9—C8	121.1 (1)
C8—C1—C2	107.2 (1)	C14—C9—C8	119.5 (1)
C8—C1—S	126.3 (1)	C11—C10—C9	120.6 (2)
C2—C1—S	126.3 (1)	C11—C10—H10	119.7
C7—C2—C3	119.4 (1)	C9—C10—H10	119.7
C7—C2—C1	105.0 (1)	C12—C11—C10	119.8 (2)
C3—C2—C1	135.6 (1)	C12—C11—H11	120.1
C4—C3—C2	116.7 (1)	C10—C11—H11	120.1
C4—C3—H3	121.6	C11—C12—C13	120.3 (2)
C2—C3—H3	121.6	C11—C12—H12	119.9
C3—C4—C5	123.1 (1)	C13—C12—H12	119.9
C3—C4—Cl	118.7 (1)	C14—C13—C12	120.4 (2)
C5—C4—Cl	118.2 (1)	C14—C13—H13	119.8
C6—C5—C4	120.4 (1)	C12—C13—H13	119.8
C6—C5—H5	119.8	C13—C14—C9	119.6 (1)
C4—C5—H5	119.8	C13—C14—H14	120.2
C7—C6—C5	116.3 (1)	C9—C14—H14	120.2
C7—C6—H6	121.9	S—C15—H15A	109.5
C5—C6—H6	121.9	S—C15—H15B	109.5
O1—C7—C6	125.3 (1)	H15A—C15—H15B	109.5
O1—C7—C2	110.6 (1)	S—C15—H15C	109.5
C6—C7—C2	124.1 (1)	H15A—C15—H15C	109.5
C1—C8—O1	110.6 (1)	H15B—C15—H15C	109.5
O2—S—C1—C8	−139.9 (1)	C2—C1—C8—O1	0.3 (2)
C15—S—C1—C8	110.7 (2)	S—C1—C8—O1	174.9 (1)
O2—S—C1—C2	33.6 (1)	C2—C1—C8—C9	179.7 (2)
C15—S—C1—C2	−75.7 (1)	S—C1—C8—C9	−5.7 (3)
S—C1—C2—C7	−174.3 (1)	C7—O1—C8—C9	179.7 (1)
C8—C1—C2—C3	−178.8 (2)	C1—C8—C9—C10	−31.6 (2)
S—C1—C2—C3	6.6 (2)	O1—C8—C9—C10	147.8 (1)
C1—C2—C3—C4	178.7 (2)	C1—C8—C9—C14	148.9 (2)
C2—C3—C4—C5	0.4 (2)	O1—C8—C9—C14	−31.7 (2)
C2—C3—C4—Cl	−178.7 (1)	C14—C9—C10—C11	−1.4 (2)
C3—C4—C5—C6	−0.3 (2)	C8—C9—C10—C11	179.0 (1)
Cl—C4—C5—C6	178.9 (1)	C9—C10—C11—C12	0.9 (2)
C4—C5—C6—C7	−0.1 (2)	C10—C11—C12—C13	0.3 (3)
C8—O1—C7—C6	179.5 (1)	C11—C12—C13—C14	−0.9 (3)
C5—C6—C7—O1	−178.2 (1)	C12—C13—C14—C9	0.4 (2)
C5—C6—C7—C2	0.2 (2)	C10—C9—C14—C13	0.8 (2)
C3—C2—C7—O1	178.5 (1)	C8—C9—C14—C13	−179.7 (1)
C1—C2—C7—C6	−179.3 (1)