1,5-Bis(thio-phen-2-yl)-3-(2,4,5-trimeth-oxy-phen-yl)pentane-1,5-dione.

In the title 1,5-diketone compound, C(22)H(22)O(5)S(2), the benzene ring makes dihedral angles of 41.51 (6) and 25.83 (6)° with the two thio-phene rings, while the dihedral angle between the thio-phene rings is 26.67 (7)°. An intra-molecular C-H⋯O inter-action generates an S(9) ring motif. In the crystal, mol-ecules are linked into a three-dimensional network by weak C-H⋯O and C-H⋯π inter-actions, and a π-π inter-action with a centroid-centroid distance of 3.6527 (8) Å.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background and applications of 1,5-diketone compounds, see: Alagarsamy et al. (2007 ▶); Favaro et al. (2002 ▶); Harrowven & Hannam (1999 ▶); Pillai et al. (2004 ▶); Rai et al. (2008 ▶). For the preparation of the title compound, see: Suwunwong et al. (2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C22H22O5S2

M = 430.54

Monoclinic,

a = 16.1955 (2) Å

b = 7.5777 (1) Å

c = 16.7706 (2) Å

β = 93.490 (1)°

V = 2054.35 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 100 K

0.26 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.928, T max = 0.949

23337 measured reflections

6027 independent reflections

4962 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.102

S = 1.04

6027 reflections

265 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681104846X/is5007sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104846X/is5007Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104846X/is5007Isup3.cml

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

C22H22O5S2	F(000) = 904
Mr = 430.54	Dx = 1.392 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6027 reflections
a = 16.1955 (2) Å	θ = 2.4–30.1°
b = 7.5777 (1) Å	µ = 0.29 mm−1
c = 16.7706 (2) Å	T = 100 K
β = 93.490 (1)°	Block, colorless
V = 2054.35 (4) Å3	0.26 × 0.20 × 0.18 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	6027 independent reflections
Radiation source: sealed tube	4962 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 30.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −22→22
Tmin = 0.928, Tmax = 0.949	k = −10→10
23337 measured reflections	l = −23→23

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0476P)2 + 0.7947P] where P = (Fo2 + 2Fc2)/3
6027 reflections	(Δ/σ)max = 0.001
265 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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	Uiso*/Ueq
S1	0.15320 (2)	−0.05956 (5)	0.46899 (2)	0.02686 (9)
S2	0.05511 (2)	0.83742 (5)	0.76099 (2)	0.02604 (9)
O1	0.26302 (6)	−0.04470 (12)	0.61509 (6)	0.0210 (2)
O2	0.11405 (6)	0.57870 (14)	0.64643 (6)	0.0245 (2)
O3	0.31333 (5)	0.28911 (14)	0.48626 (5)	0.0200 (2)
O4	0.60447 (5)	0.28712 (14)	0.57867 (6)	0.0221 (2)
O5	0.56590 (6)	0.37664 (15)	0.72042 (6)	0.0228 (2)
C1	0.07060 (9)	0.0369 (2)	0.41872 (9)	0.0287 (3)
H1A	0.0469	−0.0046	0.3690	0.034*
C2	0.04213 (9)	0.1804 (2)	0.45787 (9)	0.0261 (3)
H2A	−0.0042	0.2484	0.4388	0.031*
C3	0.08930 (8)	0.21756 (18)	0.53040 (8)	0.0203 (3)
H3A	0.0790	0.3136	0.5648	0.024*
C4	0.15231 (8)	0.09482 (17)	0.54423 (8)	0.0171 (2)
C5	0.21609 (7)	0.08266 (16)	0.60996 (7)	0.0154 (2)
C6	0.22329 (7)	0.23228 (17)	0.66977 (7)	0.0158 (2)
H6A	0.2561	0.1920	0.7181	0.019*
H6B	0.1674	0.2641	0.6858	0.019*
C7	0.26495 (7)	0.39825 (16)	0.63566 (7)	0.0144 (2)
H7A	0.2345	0.4293	0.5839	0.017*
C8	0.25704 (7)	0.55376 (17)	0.69304 (8)	0.0169 (2)
H8A	0.2753	0.5152	0.7477	0.020*
H8B	0.2946	0.6493	0.6777	0.020*
C9	0.16998 (8)	0.62670 (17)	0.69406 (8)	0.0176 (2)
C10	0.15454 (8)	0.75825 (17)	0.75553 (8)	0.0172 (2)
C11	0.20817 (8)	0.83333 (17)	0.81330 (8)	0.0184 (2)
H11A	0.2656	0.8079	0.8194	0.022*
C12	0.16658 (9)	0.95354 (18)	0.86262 (8)	0.0229 (3)
H12A	0.1931	1.0169	0.9059	0.027*
C13	0.08427 (9)	0.96710 (19)	0.84048 (9)	0.0269 (3)
H13A	0.0472	1.0412	0.8668	0.032*
C14	0.35481 (7)	0.36293 (16)	0.61902 (7)	0.0141 (2)
C15	0.37699 (7)	0.31052 (16)	0.54348 (7)	0.0152 (2)
C16	0.46025 (7)	0.28376 (17)	0.52796 (7)	0.0164 (2)
H16A	0.4744	0.2485	0.4762	0.020*
C17	0.52174 (7)	0.30865 (17)	0.58790 (8)	0.0163 (2)
C18	0.50086 (7)	0.35820 (17)	0.66468 (7)	0.0161 (2)
C19	0.41810 (7)	0.38428 (17)	0.67889 (7)	0.0155 (2)
H19A	0.4040	0.4177	0.7309	0.019*
C20	0.33368 (9)	0.2389 (2)	0.40790 (8)	0.0235 (3)
H20A	0.2827	0.2213	0.3742	0.035*
H20B	0.3655	0.1288	0.4107	0.035*
H20C	0.3668	0.3320	0.3849	0.035*
C21	0.62830 (8)	0.2351 (2)	0.50147 (8)	0.0224 (3)
H21A	0.6888	0.2286	0.5018	0.034*
H21B	0.6079	0.3219	0.4617	0.034*
H21C	0.6046	0.1191	0.4880	0.034*
C22	0.54575 (8)	0.39764 (19)	0.80143 (8)	0.0205 (3)
H22A	0.5967	0.4118	0.8354	0.031*
H22B	0.5158	0.2931	0.8184	0.031*
H22C	0.5109	0.5024	0.8061	0.031*

	U11	U22	U33	U12	U13	U23
S1	0.02481 (18)	0.0312 (2)	0.02430 (18)	−0.00215 (14)	−0.00106 (13)	−0.00875 (14)
S2	0.01850 (16)	0.02694 (18)	0.0325 (2)	0.00698 (13)	−0.00001 (13)	−0.00871 (14)
O1	0.0187 (4)	0.0189 (5)	0.0252 (5)	0.0036 (4)	0.0008 (4)	−0.0002 (4)
O2	0.0178 (4)	0.0264 (5)	0.0284 (5)	0.0055 (4)	−0.0049 (4)	−0.0080 (4)
O3	0.0151 (4)	0.0313 (5)	0.0136 (4)	0.0000 (4)	0.0000 (3)	−0.0038 (4)
O4	0.0122 (4)	0.0352 (6)	0.0194 (5)	0.0024 (4)	0.0040 (3)	−0.0034 (4)
O5	0.0134 (4)	0.0392 (6)	0.0156 (4)	0.0004 (4)	−0.0007 (3)	−0.0041 (4)
C1	0.0254 (7)	0.0389 (9)	0.0209 (7)	−0.0112 (6)	−0.0061 (5)	0.0037 (6)
C2	0.0195 (6)	0.0287 (7)	0.0292 (7)	−0.0066 (5)	−0.0054 (5)	0.0131 (6)
C3	0.0166 (6)	0.0212 (6)	0.0227 (6)	−0.0059 (5)	−0.0017 (5)	0.0037 (5)
C4	0.0155 (5)	0.0176 (6)	0.0183 (6)	−0.0029 (4)	0.0008 (4)	−0.0005 (5)
C5	0.0130 (5)	0.0167 (6)	0.0168 (6)	−0.0014 (4)	0.0031 (4)	0.0008 (4)
C6	0.0143 (5)	0.0171 (6)	0.0162 (6)	−0.0001 (4)	0.0023 (4)	−0.0006 (4)
C7	0.0124 (5)	0.0155 (5)	0.0152 (5)	0.0008 (4)	0.0011 (4)	−0.0006 (4)
C8	0.0131 (5)	0.0180 (6)	0.0194 (6)	0.0017 (4)	0.0002 (4)	−0.0030 (5)
C9	0.0162 (6)	0.0167 (6)	0.0199 (6)	0.0024 (4)	0.0007 (5)	−0.0004 (5)
C10	0.0154 (5)	0.0169 (6)	0.0195 (6)	0.0023 (4)	0.0022 (4)	0.0002 (5)
C11	0.0193 (6)	0.0177 (6)	0.0183 (6)	0.0009 (5)	0.0023 (5)	−0.0007 (5)
C12	0.0273 (7)	0.0214 (6)	0.0202 (6)	−0.0016 (5)	0.0029 (5)	−0.0034 (5)
C13	0.0291 (7)	0.0223 (7)	0.0300 (7)	0.0041 (6)	0.0082 (6)	−0.0074 (6)
C14	0.0129 (5)	0.0146 (5)	0.0149 (5)	0.0003 (4)	0.0021 (4)	0.0005 (4)
C15	0.0145 (5)	0.0169 (6)	0.0141 (5)	−0.0007 (4)	−0.0001 (4)	0.0011 (4)
C16	0.0163 (5)	0.0188 (6)	0.0146 (6)	0.0007 (4)	0.0038 (4)	−0.0003 (4)
C17	0.0127 (5)	0.0189 (6)	0.0174 (6)	0.0006 (4)	0.0030 (4)	0.0004 (5)
C18	0.0138 (5)	0.0191 (6)	0.0152 (6)	0.0002 (4)	0.0000 (4)	0.0000 (4)
C19	0.0149 (5)	0.0175 (6)	0.0144 (5)	0.0004 (4)	0.0020 (4)	−0.0008 (4)
C20	0.0236 (6)	0.0320 (7)	0.0148 (6)	0.0027 (6)	−0.0004 (5)	−0.0045 (5)
C21	0.0189 (6)	0.0279 (7)	0.0212 (6)	0.0034 (5)	0.0072 (5)	−0.0021 (5)
C22	0.0178 (6)	0.0279 (7)	0.0156 (6)	0.0006 (5)	−0.0008 (5)	−0.0024 (5)

S1—C1	1.7021 (16)	C8—H8A	0.9900
S1—C4	1.7214 (13)	C8—H8B	0.9900
S2—C13	1.6998 (15)	C9—C10	1.4665 (18)
S2—C10	1.7261 (13)	C10—C11	1.3835 (19)
O1—C5	1.2283 (15)	C11—C12	1.4266 (18)
O2—C9	1.2259 (16)	C11—H11A	0.9500
O3—C15	1.3747 (15)	C12—C13	1.366 (2)
O3—C20	1.4258 (15)	C12—H12A	0.9500
O4—C17	1.3678 (14)	C13—H13A	0.9500
O4—C21	1.4288 (16)	C14—C15	1.3954 (16)
O5—C18	1.3722 (15)	C14—C19	1.3998 (17)
O5—C22	1.4253 (15)	C15—C16	1.4035 (16)
C1—C2	1.365 (2)	C16—C17	1.3842 (18)
C1—H1A	0.9500	C16—H16A	0.9500
C2—C3	1.425 (2)	C17—C18	1.4022 (17)
C2—H2A	0.9500	C18—C19	1.3897 (16)
C3—C4	1.3897 (19)	C19—H19A	0.9500
C3—H3A	0.9500	C20—H20A	0.9800
C4—C5	1.4669 (18)	C20—H20B	0.9800
C5—C6	1.5136 (17)	C20—H20C	0.9800
C6—C7	1.5527 (17)	C21—H21A	0.9800
C6—H6A	0.9900	C21—H21B	0.9800
C6—H6B	0.9900	C21—H21C	0.9800
C7—C14	1.5222 (16)	C22—H22A	0.9800
C7—C8	1.5317 (17)	C22—H22B	0.9800
C7—H7A	1.0000	C22—H22C	0.9800
C8—C9	1.5155 (17)
C1—S1—C4	91.71 (7)	C10—C11—H11A	124.1
C13—S2—C10	91.55 (7)	C12—C11—H11A	124.1
C15—O3—C20	117.99 (10)	C13—C12—C11	112.20 (13)
C17—O4—C21	117.13 (10)	C13—C12—H12A	123.9
C18—O5—C22	116.74 (10)	C11—C12—H12A	123.9
C2—C1—S1	112.47 (11)	C12—C13—S2	112.93 (11)
C2—C1—H1A	123.8	C12—C13—H13A	123.5
S1—C1—H1A	123.8	S2—C13—H13A	123.5
C1—C2—C3	112.88 (13)	C15—C14—C19	117.79 (11)
C1—C2—H2A	123.6	C15—C14—C7	121.22 (11)
C3—C2—H2A	123.6	C19—C14—C7	120.98 (10)
C4—C3—C2	111.13 (13)	O3—C15—C14	116.35 (10)
C4—C3—H3A	124.4	O3—C15—C16	122.80 (11)
C2—C3—H3A	124.4	C14—C15—C16	120.85 (11)
C3—C4—C5	130.07 (12)	C17—C16—C15	120.17 (11)
C3—C4—S1	111.80 (10)	C17—C16—H16A	119.9
C5—C4—S1	118.11 (9)	C15—C16—H16A	119.9
O1—C5—C4	120.42 (12)	O4—C17—C16	124.60 (11)
O1—C5—C6	121.32 (12)	O4—C17—C18	115.38 (11)
C4—C5—C6	118.25 (11)	C16—C17—C18	120.02 (11)
C5—C6—C7	112.35 (10)	O5—C18—C19	125.25 (11)
C5—C6—H6A	109.1	O5—C18—C17	115.77 (10)
C7—C6—H6A	109.1	C19—C18—C17	118.98 (11)
C5—C6—H6B	109.1	C18—C19—C14	122.17 (11)
C7—C6—H6B	109.1	C18—C19—H19A	118.9
H6A—C6—H6B	107.9	C14—C19—H19A	118.9
C14—C7—C8	111.59 (10)	O3—C20—H20A	109.5
C14—C7—C6	111.52 (10)	O3—C20—H20B	109.5
C8—C7—C6	109.69 (10)	H20A—C20—H20B	109.5
C14—C7—H7A	108.0	O3—C20—H20C	109.5
C8—C7—H7A	108.0	H20A—C20—H20C	109.5
C6—C7—H7A	108.0	H20B—C20—H20C	109.5
C9—C8—C7	113.65 (10)	O4—C21—H21A	109.5
C9—C8—H8A	108.8	O4—C21—H21B	109.5
C7—C8—H8A	108.8	H21A—C21—H21B	109.5
C9—C8—H8B	108.8	O4—C21—H21C	109.5
C7—C8—H8B	108.8	H21A—C21—H21C	109.5
H8A—C8—H8B	107.7	H21B—C21—H21C	109.5
O2—C9—C10	120.59 (11)	O5—C22—H22A	109.5
O2—C9—C8	122.38 (12)	O5—C22—H22B	109.5
C10—C9—C8	117.03 (11)	H22A—C22—H22B	109.5
C11—C10—C9	130.18 (11)	O5—C22—H22C	109.5
C11—C10—S2	111.58 (9)	H22A—C22—H22C	109.5
C9—C10—S2	118.23 (10)	H22B—C22—H22C	109.5
C10—C11—C12	111.72 (12)
C4—S1—C1—C2	−0.79 (12)	C11—C12—C13—S2	0.05 (17)
S1—C1—C2—C3	1.29 (16)	C10—S2—C13—C12	0.45 (12)
C1—C2—C3—C4	−1.21 (17)	C8—C7—C14—C15	−142.95 (12)
C2—C3—C4—C5	178.95 (12)	C6—C7—C14—C15	93.99 (14)
C2—C3—C4—S1	0.60 (14)	C8—C7—C14—C19	36.21 (16)
C1—S1—C4—C3	0.09 (10)	C6—C7—C14—C19	−86.85 (14)
C1—S1—C4—C5	−178.48 (10)	C20—O3—C15—C14	178.82 (12)
C3—C4—C5—O1	174.25 (13)	C20—O3—C15—C16	−0.50 (18)
S1—C4—C5—O1	−7.49 (16)	C19—C14—C15—O3	179.39 (11)
C3—C4—C5—C6	−6.94 (19)	C7—C14—C15—O3	−1.42 (17)
S1—C4—C5—C6	171.32 (9)	C19—C14—C15—C16	−1.26 (18)
O1—C5—C6—C7	103.44 (13)	C7—C14—C15—C16	177.92 (11)
C4—C5—C6—C7	−75.37 (13)	O3—C15—C16—C17	179.52 (11)
C5—C6—C7—C14	−65.51 (13)	C14—C15—C16—C17	0.22 (19)
C5—C6—C7—C8	170.36 (10)	C21—O4—C17—C16	−0.06 (19)
C14—C7—C8—C9	164.10 (10)	C21—O4—C17—C18	179.46 (12)
C6—C7—C8—C9	−71.81 (13)	C15—C16—C17—O4	−179.56 (12)
C7—C8—C9—O2	−8.19 (18)	C15—C16—C17—C18	0.94 (19)
C7—C8—C9—C10	171.37 (11)	C22—O5—C18—C19	10.08 (19)
O2—C9—C10—C11	−178.32 (14)	C22—O5—C18—C17	−169.80 (12)
C8—C9—C10—C11	2.1 (2)	O4—C17—C18—O5	−0.66 (17)
O2—C9—C10—S2	2.17 (18)	C16—C17—C18—O5	178.88 (12)
C8—C9—C10—S2	−177.40 (9)	O4—C17—C18—C19	179.45 (11)
C13—S2—C10—C11	−0.83 (11)	C16—C17—C18—C19	−1.01 (19)
C13—S2—C10—C9	178.76 (11)	O5—C18—C19—C14	−179.96 (12)
C9—C10—C11—C12	−178.53 (13)	C17—C18—C19—C14	−0.08 (19)
S2—C10—C11—C12	1.00 (15)	C15—C14—C19—C18	1.20 (19)
C10—C11—C12—C13	−0.68 (17)	C7—C14—C19—C18	−177.99 (11)

Cg2 is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2i	0.95	2.57	3.5002 (18)	166
C3—H3A···O2	0.95	2.48	3.3677 (17)	156
C8—H8B···O1ii	0.99	2.58	3.3154 (16)	131
C21—H21A···O1iii	0.98	2.57	3.0692 (17)	112
C22—H22A···O1iv	0.98	2.39	3.3489 (16)	165
C21—H21B···Cg2v	0.98	2.91	3.8317 (16)	158

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O2i	0.95	2.57	3.5002 (18)	166
C3—H3A⋯O2	0.95	2.48	3.3677 (17)	156
C8—H8B⋯O1ii	0.99	2.58	3.3154 (16)	131
C21—H21A⋯O1iii	0.98	2.57	3.0692 (17)	112
C22—H22A⋯O1iv	0.98	2.39	3.3489 (16)	165
C21—H21B⋯Cg2v	0.98	2.91	3.8317 (16)	158

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