Literature DB >> 21582184

Propyl 2-(5-chloro-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

Hong Dae Choi, Pil Ja Seo, Byeng Wha Son, Uk Lee.

Abstract

In the title compound, C(14)H(15)ClO(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The crystal structure is stabilized by aromatic π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-to-centroid distance = 3.635 (3) Å], and by C-H⋯π inter-actions between a propyl methyl-ene H atom and the furan ring of an adjacent mol-ecule. In addition, the crystal structure exhibits weak inter-molecular C-H⋯O hydrogen bonds.

Entities: Chemical Disease Gene

Year: 2009 PMID： 21582184 PMCID： PMC2968603 DOI： 10.1107/S1600536809004735

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the crystal structures of similar alkyl 2-(5-chloro-3-methylsulfinyl-1-benzofuran-2-yl)acetates, see: Choi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C14H15ClO4S M = 314.77 Triclinic, a = 8.528 (2) Å b = 9.585 (3) Å c = 10.195 (3) Å α = 73.452 (4)° β = 81.773 (5)° γ = 65.747 (4)° V = 728.0 (4) Å3 Z = 2 Mo Kα radiation μ = 0.42 mm−1 T = 173 K 0.40 × 0.40 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.842, T max = 0.961 5062 measured reflections 2468 independent reflections 2304 reflections with I > 2σ(I) R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.094 S = 1.07 2468 reflections 182 parameters H-atom parameters constrained Δρmax = 0.28 e Å−3 Δρmin = −0.32 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004735/gk2190sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004735/gk2190Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₅ClO₄S	Z = 2
M_r = 314.77	F(000) = 328
Triclinic, P1	D_x = 1.436 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.528 (2) Å	Cell parameters from 4784 reflections
b = 9.585 (3) Å	θ = 2.4–28.3°
c = 10.195 (3) Å	µ = 0.42 mm⁻¹
α = 73.452 (4)°	T = 173 K
β = 81.773 (5)°	Block, colorless
γ = 65.747 (4)°	0.40 × 0.40 × 0.10 mm
V = 728.0 (4) Å³

Bruker SMART CCD diffractometer	2468 independent reflections
Radiation source: fine-focus sealed tube	2304 reflections with I > 2σ(I)
graphite	R_int = 0.029
Detector resolution: 10.0 pixels mm^-1	θ_max = 25.0°, θ_min = 2.1°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −11→11
T_min = 0.842, T_max = 0.961	l = −12→12
5062 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0381P)² + 0.4505P] where P = (F_o² + 2F_c²)/3
2468 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	U_iso*/U_eq
S	0.23799 (6)	0.59458 (6)	0.53751 (4)	0.02410 (15)
Cl	−0.18859 (7)	0.22051 (7)	0.88822 (6)	0.03715 (17)
O1	0.33263 (16)	0.45103 (15)	0.93160 (12)	0.0223 (3)
O2	0.46225 (18)	0.85866 (17)	0.78142 (17)	0.0349 (4)
O3	0.21787 (18)	0.86811 (17)	0.71372 (15)	0.0338 (4)
O4	0.24182 (19)	0.46691 (18)	0.47748 (14)	0.0321 (4)
C1	0.2395 (2)	0.5204 (2)	0.71715 (18)	0.0206 (4)
C2	0.1483 (2)	0.4276 (2)	0.80462 (18)	0.0203 (4)
C3	0.0205 (2)	0.3780 (2)	0.78783 (19)	0.0228 (4)
H3	−0.0289	0.4059	0.7016	0.027*
C4	−0.0300 (2)	0.2866 (2)	0.9031 (2)	0.0249 (4)
C5	0.0395 (3)	0.2434 (2)	1.0326 (2)	0.0266 (4)
H5	0.0019	0.1786	1.1082	0.032*
C6	0.1625 (2)	0.2954 (2)	1.04984 (19)	0.0252 (4)
H6	0.2100	0.2693	1.1366	0.030*
C7	0.2134 (2)	0.3870 (2)	0.93509 (19)	0.0209 (4)
C8	0.3462 (2)	0.5306 (2)	0.79717 (18)	0.0211 (4)
C9	0.4628 (2)	0.6175 (2)	0.76992 (19)	0.0229 (4)
H9A	0.5337	0.5986	0.6860	0.028*
H9B	0.5416	0.5757	0.8470	0.028*
C10	0.3636 (2)	0.7945 (2)	0.75211 (19)	0.0244 (4)
C11	0.3854 (3)	1.0300 (3)	0.7669 (3)	0.0439 (6)
H11A	0.3053	1.0552	0.8453	0.053*
H11B	0.3204	1.0848	0.6815	0.053*
C12	0.5296 (3)	1.0819 (3)	0.7631 (3)	0.0451 (6)
H12A	0.4800	1.1959	0.7603	0.054*
H12B	0.5932	1.0244	0.8489	0.054*
C13	0.6534 (5)	1.0561 (4)	0.6453 (4)	0.0753 (10)
H13A	0.5929	1.1158	0.5596	0.090*
H13B	0.7052	0.9432	0.6478	0.090*
H13C	0.7439	1.0921	0.6509	0.090*
C14	0.0216 (3)	0.7411 (2)	0.5235 (2)	0.0318 (5)
H14A	0.0002	0.8006	0.4277	0.048*
H14B	0.0062	0.8137	0.5798	0.048*
H14C	−0.0595	0.6891	0.5554	0.048*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0256 (3)	0.0286 (3)	0.0184 (2)	−0.0127 (2)	−0.00144 (18)	−0.00292 (19)
Cl	0.0348 (3)	0.0380 (3)	0.0473 (3)	−0.0243 (2)	−0.0025 (2)	−0.0075 (2)
O1	0.0237 (7)	0.0252 (7)	0.0198 (6)	−0.0117 (6)	−0.0034 (5)	−0.0035 (5)
O2	0.0254 (8)	0.0228 (7)	0.0590 (10)	−0.0088 (6)	−0.0060 (7)	−0.0128 (7)
O3	0.0249 (8)	0.0292 (8)	0.0437 (9)	−0.0098 (6)	−0.0075 (6)	−0.0019 (7)
O4	0.0341 (8)	0.0393 (8)	0.0260 (7)	−0.0132 (7)	−0.0016 (6)	−0.0143 (6)
C1	0.0228 (9)	0.0198 (9)	0.0190 (9)	−0.0080 (7)	−0.0015 (7)	−0.0047 (7)
C2	0.0211 (9)	0.0173 (9)	0.0207 (9)	−0.0054 (7)	−0.0012 (7)	−0.0053 (7)
C3	0.0234 (10)	0.0217 (9)	0.0254 (10)	−0.0086 (8)	−0.0026 (7)	−0.0085 (8)
C4	0.0214 (10)	0.0210 (10)	0.0346 (11)	−0.0088 (8)	0.0007 (8)	−0.0105 (8)
C5	0.0268 (10)	0.0209 (10)	0.0274 (10)	−0.0088 (8)	0.0031 (8)	−0.0019 (8)
C6	0.0252 (10)	0.0244 (10)	0.0225 (9)	−0.0074 (8)	−0.0020 (8)	−0.0033 (8)
C7	0.0196 (9)	0.0192 (9)	0.0240 (9)	−0.0069 (7)	−0.0013 (7)	−0.0062 (7)
C8	0.0220 (9)	0.0196 (9)	0.0204 (9)	−0.0074 (8)	−0.0004 (7)	−0.0039 (7)
C9	0.0202 (9)	0.0244 (10)	0.0261 (9)	−0.0103 (8)	−0.0015 (7)	−0.0064 (8)
C10	0.0250 (10)	0.0269 (10)	0.0233 (9)	−0.0139 (9)	0.0003 (8)	−0.0039 (8)
C11	0.0322 (12)	0.0236 (11)	0.0760 (18)	−0.0075 (10)	−0.0016 (11)	−0.0177 (11)
C12	0.0357 (13)	0.0242 (11)	0.0760 (18)	−0.0114 (10)	−0.0014 (12)	−0.0139 (11)
C13	0.080 (2)	0.0462 (17)	0.093 (2)	−0.0344 (16)	0.0380 (19)	−0.0128 (16)
C14	0.0314 (11)	0.0270 (11)	0.0325 (11)	−0.0069 (9)	−0.0078 (9)	−0.0043 (9)

S—O4	1.5038 (16)	C6—C7	1.382 (3)
S—C1	1.7656 (18)	C6—H6	0.9500
S—C14	1.797 (2)	C8—C9	1.493 (3)
Cl—C4	1.752 (2)	C9—C10	1.522 (3)
O1—C7	1.379 (2)	C9—H9A	0.9900
O1—C8	1.380 (2)	C9—H9B	0.9900
O2—C10	1.333 (2)	C11—C12	1.496 (3)
O2—C11	1.468 (3)	C11—H11A	0.9900
O3—C10	1.207 (2)	C11—H11B	0.9900
C1—C8	1.354 (3)	C12—C13	1.487 (4)
C1—C2	1.452 (3)	C12—H12A	0.9900
C2—C3	1.403 (3)	C12—H12B	0.9900
C2—C7	1.403 (3)	C13—H13A	0.9800
C3—C4	1.383 (3)	C13—H13B	0.9800
C3—H3	0.9500	C13—H13C	0.9800
C4—C5	1.407 (3)	C14—H14A	0.9800
C5—C6	1.383 (3)	C14—H14B	0.9800
C5—H5	0.9500	C14—H14C	0.9800

O4—S—C1	106.94 (9)	C10—C9—H9A	109.2
O4—S—C14	106.77 (10)	C8—C9—H9B	109.2
C1—S—C14	98.32 (9)	C10—C9—H9B	109.2
C7—O1—C8	106.32 (14)	H9A—C9—H9B	107.9
C10—O2—C11	116.86 (16)	O3—C10—O2	124.34 (19)
C8—C1—C2	107.36 (16)	O3—C10—C9	125.35 (19)
C8—C1—S	122.84 (15)	O2—C10—C9	110.29 (16)
C2—C1—S	129.51 (15)	O2—C11—C12	107.24 (18)
C3—C2—C7	119.33 (17)	O2—C11—H11A	110.3
C3—C2—C1	136.18 (17)	C12—C11—H11A	110.3
C7—C2—C1	104.48 (17)	O2—C11—H11B	110.3
C4—C3—C2	116.72 (17)	C12—C11—H11B	110.3
C4—C3—H3	121.6	H11A—C11—H11B	108.5
C2—C3—H3	121.6	C13—C12—C11	114.7 (3)
C3—C4—C5	123.34 (19)	C13—C12—H12A	108.6
C3—C4—Cl	118.78 (15)	C11—C12—H12A	108.6
C5—C4—Cl	117.87 (15)	C13—C12—H12B	108.6
C6—C5—C4	119.91 (18)	C11—C12—H12B	108.6
C6—C5—H5	120.0	H12A—C12—H12B	107.6
C4—C5—H5	120.0	C12—C13—H13A	109.5
C7—C6—C5	117.01 (18)	C12—C13—H13B	109.5
C7—C6—H6	121.5	H13A—C13—H13B	109.5
C5—C6—H6	121.5	C12—C13—H13C	109.5
O1—C7—C6	125.69 (17)	H13A—C13—H13C	109.5
O1—C7—C2	110.66 (16)	H13B—C13—H13C	109.5
C6—C7—C2	123.65 (18)	S—C14—H14A	109.5
C1—C8—O1	111.16 (17)	S—C14—H14B	109.5
C1—C8—C9	132.90 (17)	H14A—C14—H14B	109.5
O1—C8—C9	115.80 (16)	S—C14—H14C	109.5
C8—C9—C10	112.11 (15)	H14A—C14—H14C	109.5
C8—C9—H9A	109.2	H14B—C14—H14C	109.5

O4—S—C1—C8	132.24 (16)	C3—C2—C7—O1	−177.81 (15)
C14—S—C1—C8	−117.31 (17)	C1—C2—C7—O1	1.2 (2)
O4—S—C1—C2	−40.91 (19)	C3—C2—C7—C6	2.1 (3)
C14—S—C1—C2	69.54 (19)	C1—C2—C7—C6	−178.94 (17)
C8—C1—C2—C3	178.0 (2)	C2—C1—C8—O1	0.0 (2)
S—C1—C2—C3	−8.0 (3)	S—C1—C8—O1	−174.43 (12)
C8—C1—C2—C7	−0.7 (2)	C2—C1—C8—C9	−175.32 (19)
S—C1—C2—C7	173.25 (14)	S—C1—C8—C9	10.2 (3)
C7—C2—C3—C4	−1.9 (3)	C7—O1—C8—C1	0.7 (2)
C1—C2—C3—C4	179.6 (2)	C7—O1—C8—C9	176.90 (15)
C2—C3—C4—C5	0.3 (3)	C1—C8—C9—C10	72.8 (3)
C2—C3—C4—Cl	−179.76 (13)	O1—C8—C9—C10	−102.43 (18)
C3—C4—C5—C6	1.2 (3)	C11—O2—C10—O3	0.8 (3)
Cl—C4—C5—C6	−178.73 (15)	C11—O2—C10—C9	179.06 (18)
C4—C5—C6—C7	−1.1 (3)	C8—C9—C10—O3	−26.0 (3)
C8—O1—C7—C6	178.95 (18)	C8—C9—C10—O2	155.70 (16)
C8—O1—C7—C2	−1.16 (19)	C10—O2—C11—C12	−163.3 (2)
C5—C6—C7—O1	179.33 (17)	O2—C11—C12—C13	62.5 (3)
C5—C6—C7—C2	−0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···Cg2ⁱ	0.99	2.74	3.666 (3)	155
C3—H3···O4ⁱⁱ	0.95	2.44	3.353 (2)	160
C5—H5···O3ⁱⁱⁱ	0.95	2.50	3.373 (2)	152
C9—H9A···O4^iv	0.99	2.35	3.321 (2)	166
C9—H9B···O1^v	0.99	2.54	3.489 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯Cg2ⁱ	0.99	2.74	3.666 (3)	155
C3—H3⋯O4ⁱⁱ	0.95	2.44	3.353 (2)	160
C5—H5⋯O3ⁱⁱⁱ	0.95	2.50	3.373 (2)	152
C9—H9A⋯O4^iv	0.99	2.35	3.321 (2)	166
C9—H9B⋯O1^v	0.99	2.54	3.489 (2)	161

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Methyl 2-(5-chloro-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

Authors: Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-10-18

2 in total