1,3,5-Tris(2-acetyl­thienyl)benzene

In the title mol­ecule, C₂₄H₁₈O₃S₃, all bond lengths and angles are normal. The three thio­phene rings make dihedral angles of 21.7 (3), 19.3 (7) and 4.8 (4)° with the central benzene ring. The crystal packing is stabilized by weak inter­molecular C—H...O hydrogen bonds and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.054
• wR factor = 0.171
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.68 mm
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C12
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C18
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C24

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.01
           From the CIF: _reflns_number_total               3183
           Count of symmetry unique reflns         1930
           Completeness (_total/calc)            164.92%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1253
           Fraction of Friedel pairs measured     0.649
           Are heavy atom types Z>Si present        yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   5 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, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

1,3,5-Tris(2-acetylthienyl)benzene

Crystal data

C24H18O3S3	Dx = 1.395 Mg m^−3
Mr = 450.56	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 1331 reflections
a = 25.620 (16) Å	θ = 2.6–20.8°
b = 4.179 (3) Å	µ = 0.37 mm^−1
c = 20.043 (13) Å	T = 298 K
V = 2146 (2) Å^3	Block, white
Z = 4	0.68 × 0.39 × 0.08 mm
F(000) = 936

Data collection

Bruker SMART CCD area-detector diffractometer	3183 independent reflections
Radiation source: fine-focus sealed tube	2210 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.080
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −29→30
Tmin = 0.787, Tmax = 0.971	k = −4→4
10099 measured reflections	l = −23→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.171	w = 1/[σ^2(Fo^2) + (0.0036P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max = 0.001
3183 reflections	Δρmax = 0.23 e Å^−3
271 parameters	Δρmin = −0.24 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.09 (14)

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
O1	0.1590 (2)	1.5033 (17)	0.5422 (3)	0.0775 (18)
O2	0.47853 (19)	1.3858 (16)	0.7430 (3)	0.0867 (19)
O3	0.03762 (19)	−0.0345 (14)	1.0139 (3)	0.0721 (15)
S1	0.19123 (6)	1.1666 (4)	0.66752 (8)	0.0486 (5)
S2	0.37494 (6)	1.1169 (5)	0.78654 (9)	0.0526 (5)
S3	0.12430 (6)	0.2821 (4)	0.94560 (9)	0.0456 (4)
C1	0.2036 (2)	0.8763 (15)	0.7924 (3)	0.0380 (14)
C2	0.2558 (2)	0.9600 (15)	0.7952 (3)	0.0414 (15)
H2	0.2701	1.0884	0.7620	0.050*
C3	0.2876 (2)	0.8521 (15)	0.8479 (3)	0.0355 (14)
C4	0.2659 (2)	0.6642 (14)	0.8974 (3)	0.0375 (14)
H4	0.2867	0.5950	0.9326	0.045*
C5	0.2129 (2)	0.5753 (15)	0.8958 (3)	0.0354 (14)
C6	0.1828 (2)	0.6812 (15)	0.8417 (3)	0.0393 (15)
H6	0.1480	0.6192	0.8389	0.047*
C7	0.1681 (2)	1.0081 (15)	0.7403 (3)	0.0384 (15)
C8	0.1150 (2)	1.0450 (18)	0.7447 (4)	0.0518 (19)
H8	0.0956	0.9760	0.7811	0.062*
C9	0.0930 (2)	1.1946 (16)	0.6898 (3)	0.0443 (16)
H9	0.0574	1.2319	0.6852	0.053*
C10	0.1293 (2)	1.2823 (16)	0.6427 (3)	0.0408 (15)
C11	0.1215 (3)	1.4458 (18)	0.5799 (4)	0.0493 (18)
C12	0.0673 (3)	1.5487 (19)	0.5620 (4)	0.061 (2)
H12A	0.0677	1.6526	0.5193	0.092*
H12B	0.0545	1.6948	0.5952	0.092*
H12C	0.0449	1.3647	0.5601	0.092*
C13	0.3422 (2)	0.9637 (16)	0.8539 (3)	0.0407 (15)
C14	0.3723 (2)	0.9694 (18)	0.9091 (4)	0.0526 (18)
H14	0.3613	0.8954	0.9506	0.063*
C15	0.4226 (2)	1.1009 (18)	0.8972 (4)	0.0525 (18)
H15	0.4481	1.1202	0.9299	0.063*
C16	0.4295 (2)	1.1954 (16)	0.8328 (3)	0.0422 (15)
C17	0.4751 (2)	1.3412 (19)	0.8034 (4)	0.054 (2)
C18	0.5192 (2)	1.4403 (19)	0.8494 (4)	0.059 (2)
H18A	0.5469	1.5328	0.8235	0.089*
H18B	0.5321	1.2559	0.8728	0.089*
H18C	0.5066	1.5948	0.8809	0.089*
C19	0.1897 (2)	0.3826 (13)	0.9495 (3)	0.0368 (14)
C20	0.2109 (3)	0.2717 (17)	1.0064 (4)	0.0518 (18)
H20	0.2459	0.3003	1.0172	0.062*
C21	0.1755 (3)	0.1080 (18)	1.0484 (4)	0.0546 (19)
H21	0.1845	0.0189	1.0893	0.066*
C22	0.1261 (2)	0.0966 (18)	1.0213 (3)	0.0438 (16)
C23	0.0779 (3)	−0.0513 (17)	1.0477 (4)	0.0521 (18)
C24	0.0781 (3)	−0.197 (2)	1.1158 (4)	0.072 (2)
H24A	0.0442	−0.2827	1.1254	0.108*
H24B	0.0867	−0.0357	1.1481	0.108*
H24C	0.1036	−0.3649	1.1175	0.108*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.055 (3)	0.121 (5)	0.055 (3)	0.004 (3)	0.006 (3)	0.030 (3)
O2	0.054 (3)	0.139 (6)	0.066 (4)	−0.032 (3)	0.008 (3)	0.025 (4)
O3	0.045 (3)	0.091 (4)	0.081 (4)	−0.013 (3)	0.003 (3)	0.008 (3)
S1	0.0341 (8)	0.0713 (11)	0.0405 (10)	0.0013 (8)	0.0015 (7)	0.0078 (9)
S2	0.0371 (8)	0.0809 (13)	0.0397 (10)	−0.0118 (8)	−0.0014 (8)	0.0089 (10)
S3	0.0322 (7)	0.0600 (11)	0.0448 (10)	−0.0033 (7)	0.0006 (7)	0.0038 (9)
C1	0.031 (3)	0.048 (4)	0.035 (3)	−0.003 (2)	0.002 (3)	−0.003 (3)
C2	0.033 (3)	0.054 (4)	0.037 (3)	0.001 (3)	0.001 (3)	0.004 (3)
C3	0.023 (3)	0.043 (4)	0.040 (4)	0.004 (3)	0.002 (2)	−0.004 (3)
C4	0.034 (3)	0.045 (4)	0.033 (3)	0.004 (3)	0.000 (3)	0.002 (3)
C5	0.031 (3)	0.042 (4)	0.033 (3)	0.003 (2)	−0.001 (3)	−0.003 (3)
C6	0.034 (3)	0.042 (4)	0.042 (4)	−0.005 (3)	0.000 (3)	0.000 (3)
C7	0.038 (3)	0.045 (4)	0.033 (4)	−0.004 (3)	0.001 (3)	0.000 (3)
C8	0.038 (3)	0.072 (5)	0.045 (4)	0.005 (3)	0.004 (3)	0.013 (4)
C9	0.027 (3)	0.062 (4)	0.044 (4)	0.006 (3)	−0.002 (3)	0.011 (3)
C10	0.033 (3)	0.050 (4)	0.040 (4)	0.004 (3)	−0.003 (3)	−0.005 (3)
C11	0.046 (4)	0.058 (5)	0.044 (4)	−0.004 (3)	−0.013 (3)	0.004 (3)
C12	0.056 (4)	0.072 (6)	0.056 (5)	0.001 (4)	−0.012 (4)	0.020 (4)
C13	0.036 (3)	0.048 (4)	0.038 (4)	−0.003 (3)	0.002 (3)	−0.003 (3)
C14	0.048 (4)	0.074 (5)	0.035 (4)	−0.015 (3)	0.001 (3)	0.012 (3)
C15	0.037 (3)	0.078 (5)	0.043 (4)	−0.008 (3)	−0.012 (3)	0.008 (4)
C16	0.026 (3)	0.056 (4)	0.045 (4)	0.000 (3)	0.000 (3)	0.003 (3)
C17	0.037 (4)	0.070 (6)	0.055 (5)	−0.004 (3)	0.005 (3)	0.012 (4)
C18	0.029 (3)	0.075 (5)	0.073 (6)	−0.010 (3)	0.003 (3)	−0.001 (4)
C19	0.035 (3)	0.042 (4)	0.034 (4)	−0.002 (2)	0.003 (3)	−0.002 (3)
C20	0.037 (3)	0.058 (5)	0.060 (5)	−0.008 (3)	−0.005 (3)	0.007 (4)
C21	0.049 (4)	0.067 (5)	0.048 (4)	−0.011 (3)	−0.004 (3)	0.014 (4)
C22	0.038 (3)	0.049 (4)	0.044 (4)	−0.001 (3)	0.000 (3)	0.005 (3)
C23	0.051 (4)	0.056 (5)	0.049 (4)	−0.006 (3)	0.015 (4)	−0.002 (4)
C24	0.080 (5)	0.085 (6)	0.052 (5)	−0.030 (5)	0.008 (4)	0.008 (4)

Geometric parameters (Å, º)

O1—C11	1.247 (8)	C10—C11	1.445 (10)
O2—C17	1.227 (10)	C11—C12	1.496 (9)
O3—C23	1.237 (9)	C12—H12A	0.9600
S1—C7	1.708 (6)	C12—H12B	0.9600
S1—C10	1.732 (6)	C12—H12C	0.9600
S2—C16	1.709 (6)	C13—C14	1.350 (9)
S2—C13	1.713 (7)	C14—C15	1.422 (9)
S3—C22	1.705 (7)	C14—H14	0.9300
S3—C19	1.728 (6)	C15—C16	1.361 (9)
C1—C2	1.385 (8)	C15—H15	0.9300
C1—C6	1.388 (9)	C16—C17	1.444 (9)
C1—C7	1.491 (8)	C17—C18	1.516 (10)
C2—C3	1.408 (8)	C18—H18A	0.9600
C2—H2	0.9300	C18—H18B	0.9600
C3—C4	1.382 (8)	C18—H18C	0.9600
C3—C13	1.480 (8)	C19—C20	1.347 (9)
C4—C5	1.408 (8)	C20—C21	1.413 (10)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.400 (8)	C21—C22	1.378 (9)
C5—C19	1.470 (9)	C21—H21	0.9300
C6—H6	0.9300	C22—C23	1.479 (9)
C7—C8	1.371 (8)	C23—C24	1.493 (11)
C8—C9	1.386 (9)	C24—H24A	0.9600
C8—H8	0.9300	C24—H24B	0.9600
C9—C10	1.375 (9)	C24—H24C	0.9600
C9—H9	0.9300
C7—S1—C10	92.0 (3)	C14—C13—C3	127.7 (6)
C16—S2—C13	92.6 (3)	C14—C13—S2	111.1 (4)
C22—S3—C19	92.5 (3)	C3—C13—S2	121.2 (5)
C2—C1—C6	119.4 (6)	C13—C14—C15	112.7 (6)
C2—C1—C7	121.7 (6)	C13—C14—H14	123.7
C6—C1—C7	118.8 (5)	C15—C14—H14	123.7
C1—C2—C3	120.5 (6)	C16—C15—C14	113.0 (6)
C1—C2—H2	119.7	C16—C15—H15	123.5
C3—C2—H2	119.7	C14—C15—H15	123.5
C4—C3—C2	119.3 (5)	C15—C16—C17	127.9 (6)
C4—C3—C13	120.1 (6)	C15—C16—S2	110.6 (5)
C2—C3—C13	120.4 (6)	C17—C16—S2	121.4 (5)
C3—C4—C5	121.4 (6)	O2—C17—C16	121.6 (6)
C3—C4—H4	119.3	O2—C17—C18	120.3 (6)
C5—C4—H4	119.3	C16—C17—C18	118.1 (6)
C6—C5—C4	117.7 (6)	C17—C18—H18A	109.5
C6—C5—C19	121.1 (5)	C17—C18—H18B	109.5
C4—C5—C19	121.1 (5)	H18A—C18—H18B	109.5
C1—C6—C5	121.7 (5)	C17—C18—H18C	109.5
C1—C6—H6	119.2	H18A—C18—H18C	109.5
C5—C6—H6	119.2	H18B—C18—H18C	109.5
C8—C7—C1	127.0 (6)	C20—C19—C5	130.2 (5)
C8—C7—S1	110.8 (5)	C20—C19—S3	110.3 (5)
C1—C7—S1	122.0 (4)	C5—C19—S3	119.5 (4)
C7—C8—C9	113.8 (6)	C19—C20—C21	114.3 (6)
C7—C8—H8	123.1	C19—C20—H20	122.9
C9—C8—H8	123.1	C21—C20—H20	122.9
C10—C9—C8	112.9 (5)	C22—C21—C20	111.8 (7)
C10—C9—H9	123.5	C22—C21—H21	124.1
C8—C9—H9	123.5	C20—C21—H21	124.1
C9—C10—C11	129.0 (6)	C21—C22—C23	129.9 (7)
C9—C10—S1	110.4 (5)	C21—C22—S3	111.1 (5)
C11—C10—S1	120.6 (5)	C23—C22—S3	119.1 (5)
O1—C11—C10	120.7 (6)	O3—C23—C22	118.5 (7)
O1—C11—C12	121.0 (7)	O3—C23—C24	121.8 (7)
C10—C11—C12	118.3 (6)	C22—C23—C24	119.6 (7)
C11—C12—H12A	109.5	C23—C24—H24A	109.5
C11—C12—H12B	109.5	C23—C24—H24B	109.5
H12A—C12—H12B	109.5	H24A—C24—H24B	109.5
C11—C12—H12C	109.5	C23—C24—H24C	109.5
H12A—C12—H12C	109.5	H24A—C24—H24C	109.5
H12B—C12—H12C	109.5	H24B—C24—H24C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1^i	0.93	2.52	3.399 (10)	159

Symmetry code: (i) −x+1/2, y−1, z+1/2.