A flip-disorder in the structure of 3-[2-(anthracen-9-yl)ethen­yl]thio­phene

In the crystal structure of the title compound, C₂₀H₁₄S, the thio­phene rings are disordered; such a flip-type disorder is typical for simple, monosubstituted thio­phene derivatives. Two planar fragments, the thio­phene and the anthracene units, are almost perpendicular in order to relieve the H...H steric strains. The crystal packing is determined by van der Waals inter­actions, π–π stacking between the anthracene fragments, and some weak C—H...S and C—H...π short directional contacts.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.060
• wR factor = 0.110
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.54 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C17
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        S17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        S13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C14    -   C15    ...       1.38 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  S13     ..       3.02 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8     ..  S13     ..       2.94 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  S17     ..       3.11 Ang.

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL023_ALERT_1_A There is a mismatched ^ on line 213
              close to each other, which influence their <i>U</i>ij^ values. The
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989); software used to prepare material for publication: SHELXL97.

3-[2-(anthracen-9-yl)ethenyl]thiophene

Crystal data

C20H14S	F(000) = 600
Mr = 286.37	Dx = 1.329 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1986 reflections
a = 5.4991 (9) Å	θ = 2.5–28.9°
b = 23.968 (4) Å	µ = 0.22 mm^−1
c = 10.9768 (18) Å	T = 100 K
β = 98.478 (14)°	Block, colourless
V = 1431.0 (4) Å^3	0.3 × 0.07 × 0.05 mm
Z = 4

Data collection

Kuma KM-4-CCD four-circle diffractometer	1419 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.074
Graphite monochromator	θmax = 26.0°, θmin = 3.4°
ω scans	h = −6→6
6934 measured reflections	k = −29→29
2710 independent reflections	l = −13→11

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.04P)^2] where P = (Fo^2 + 2Fc^2)/3
2710 reflections	(Δ/σ)max = 0.001
197 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.32 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	Occ. (<1)
S13	0.0097 (8)	0.04639 (19)	0.6482 (4)	0.0203 (6)	0.689 (3)
C17	0.248 (5)	0.0658 (11)	0.557 (2)	0.0502 (12)	0.689 (3)
H17	0.3513	0.0413	0.5200	0.060*	0.689 (3)
S17	0.252 (3)	0.0583 (6)	0.5632 (14)	0.0502 (12)	0.311 (3)
C13	0.029 (7)	0.0514 (17)	0.643 (3)	0.0203 (6)	0.311 (3)
H13	−0.0335	0.0173	0.6694	0.024*	0.311 (3)
C14	−0.0670 (5)	0.11218 (12)	0.6675 (2)	0.0286 (8)
H14	−0.1961	0.1224	0.7118	0.034*
C15	0.0707 (5)	0.15122 (12)	0.6144 (2)	0.0219 (7)
C16	0.2485 (5)	0.12428 (12)	0.5538 (2)	0.0223 (7)
H16	0.3613	0.1446	0.5132	0.027*
C12	0.0325 (5)	0.21124 (12)	0.6215 (2)	0.0249 (7)
H12	−0.1068	0.2231	0.6566	0.030*
C11	0.1716 (5)	0.25112 (12)	0.5841 (2)	0.0235 (7)
H11	0.3097	0.2397	0.5476	0.028*
C1	0.4565 (5)	0.43483 (11)	0.7597 (2)	0.0225 (7)
H1	0.4370	0.4740	0.7668	0.027*
C2	0.6556 (5)	0.40997 (12)	0.8238 (2)	0.0256 (7)
H2	0.7742	0.4317	0.8747	0.031*
C3	0.6885 (5)	0.35094 (12)	0.8153 (2)	0.0254 (7)
H3	0.8292	0.3336	0.8602	0.030*
C4	0.5185 (5)	0.31972 (12)	0.7428 (2)	0.0229 (7)
H4	0.5412	0.2805	0.7393	0.027*
C4A	0.3064 (5)	0.34417 (12)	0.6718 (2)	0.0200 (7)
C5	0.1304 (5)	0.31238 (11)	0.5943 (2)	0.0197 (7)
C5A	−0.0778 (5)	0.33852 (12)	0.5252 (2)	0.0203 (7)
C6	−0.2630 (5)	0.30907 (12)	0.4459 (2)	0.0224 (7)
H6	−0.2442	0.2700	0.4353	0.027*
C7	−0.4648 (5)	0.33474 (12)	0.3850 (2)	0.0250 (8)
H7	−0.5856	0.3136	0.3340	0.030*
C8	−0.4963 (5)	0.39327 (12)	0.3973 (2)	0.0258 (8)
H8	−0.6384	0.4112	0.3552	0.031*
C9	−0.3216 (5)	0.42337 (12)	0.4697 (2)	0.0245 (7)
H9	−0.3423	0.4626	0.4761	0.029*
C9A	−0.1088 (5)	0.39787 (12)	0.5362 (2)	0.0205 (7)
C10	0.0677 (5)	0.42868 (11)	0.6134 (2)	0.0231 (7)
H10	0.0464	0.4678	0.6197	0.028*
C1A	0.2740 (5)	0.40376 (11)	0.6813 (2)	0.0200 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S13	0.0211 (9)	0.0181 (11)	0.0207 (6)	−0.0032 (7)	−0.0003 (5)	0.0015 (6)
C17	0.0480 (13)	0.063 (3)	0.0364 (17)	−0.011 (2)	−0.0036 (12)	0.0106 (19)
S17	0.0480 (13)	0.063 (3)	0.0364 (17)	−0.011 (2)	−0.0036 (12)	0.0106 (19)
C13	0.0211 (9)	0.0181 (11)	0.0207 (6)	−0.0032 (7)	−0.0003 (5)	0.0015 (6)
C14	0.026 (2)	0.037 (2)	0.0199 (15)	−0.0048 (15)	−0.0041 (14)	0.0009 (14)
C15	0.0235 (19)	0.0225 (17)	0.0164 (14)	0.0025 (15)	−0.0077 (13)	0.0014 (13)
C16	0.0192 (18)	0.0225 (18)	0.0236 (15)	−0.0041 (14)	−0.0027 (13)	0.0000 (13)
C12	0.0213 (19)	0.0299 (19)	0.0228 (16)	0.0049 (15)	0.0009 (14)	0.0032 (14)
C11	0.0179 (19)	0.032 (2)	0.0191 (15)	−0.0010 (15)	−0.0022 (13)	−0.0023 (13)
C1	0.0224 (19)	0.0228 (18)	0.0227 (15)	−0.0036 (15)	0.0042 (14)	−0.0027 (13)
C2	0.027 (2)	0.029 (2)	0.0205 (15)	−0.0075 (15)	0.0023 (15)	−0.0056 (14)
C3	0.0199 (19)	0.036 (2)	0.0185 (15)	−0.0019 (15)	−0.0027 (14)	0.0011 (13)
C4	0.0218 (19)	0.0246 (18)	0.0223 (15)	0.0003 (15)	0.0033 (14)	0.0015 (14)
C4A	0.0195 (19)	0.0243 (18)	0.0162 (15)	−0.0022 (15)	0.0032 (13)	0.0013 (13)
C5	0.0206 (19)	0.0203 (18)	0.0185 (14)	−0.0033 (14)	0.0039 (13)	−0.0001 (13)
C5A	0.0177 (19)	0.0262 (19)	0.0173 (15)	−0.0017 (14)	0.0033 (14)	−0.0012 (12)
C6	0.0224 (19)	0.0267 (18)	0.0179 (14)	0.0001 (15)	0.0022 (14)	0.0018 (13)
C7	0.025 (2)	0.033 (2)	0.0167 (15)	−0.0024 (15)	0.0003 (14)	0.0010 (13)
C8	0.023 (2)	0.034 (2)	0.0194 (15)	0.0040 (15)	0.0019 (15)	0.0036 (13)
C9	0.025 (2)	0.0272 (18)	0.0222 (15)	0.0033 (15)	0.0068 (15)	0.0041 (14)
C9A	0.0201 (18)	0.0253 (18)	0.0167 (14)	0.0003 (14)	0.0042 (13)	0.0019 (13)
C10	0.027 (2)	0.0212 (17)	0.0229 (15)	−0.0001 (15)	0.0083 (15)	−0.0011 (13)
C1A	0.0212 (19)	0.0228 (18)	0.0163 (15)	−0.0022 (15)	0.0038 (14)	−0.0003 (13)

Geometric parameters (Å, º)

S13—C14	1.654 (6)	C2—H2	0.9500
S13—C17	1.82 (3)	C3—C4	1.359 (4)
C17—C16	1.40 (2)	C3—H3	0.9500
C17—H17	0.9500	C4—C4A	1.430 (4)
S17—C16	1.585 (16)	C4—H4	0.9500
S17—C13	1.62 (4)	C4A—C5	1.414 (4)
C13—C14	1.59 (4)	C4A—C1A	1.445 (3)
C13—H13	0.9500	C5—C5A	1.422 (3)
C14—C15	1.385 (4)	C5A—C6	1.426 (4)
C14—H14	0.9500	C5A—C9A	1.440 (4)
C15—C16	1.417 (4)	C6—C7	1.356 (3)
C15—C12	1.458 (4)	C6—H6	0.9500
C16—H16	0.9500	C7—C8	1.422 (4)
C12—C11	1.327 (4)	C7—H7	0.9500
C12—H12	0.9500	C8—C9	1.360 (4)
C11—C5	1.492 (4)	C8—H8	0.9500
C11—H11	0.9500	C9—C9A	1.422 (4)
C1—C2	1.349 (4)	C9—H9	0.9500
C1—C1A	1.431 (4)	C9A—C10	1.401 (4)
C1—H1	0.9500	C10—C1A	1.396 (4)
C2—C3	1.431 (4)	C10—H10	0.9500
C14—S13—C17	92.6 (8)	C2—C3—H3	120.0
C16—C17—S13	105.9 (17)	C3—C4—C4A	121.9 (3)
C16—C17—H17	127.1	C3—C4—H4	119.0
S13—C17—H17	127.1	C4A—C4—H4	119.0
C16—S17—C13	97.6 (17)	C5—C4A—C4	122.6 (3)
C14—C13—S17	107 (2)	C5—C4A—C1A	119.7 (3)
C14—C13—H13	126.3	C4—C4A—C1A	117.7 (2)
S17—C13—H13	126.3	C4A—C5—C5A	120.6 (3)
C15—C14—C13	109.4 (14)	C4A—C5—C11	118.5 (2)
C15—C14—S13	115.1 (3)	C5A—C5—C11	120.9 (2)
C15—C14—H14	122.4	C5—C5A—C6	123.6 (3)
C13—C14—H14	128.2	C5—C5A—C9A	119.1 (3)
S13—C14—H14	122.4	C6—C5A—C9A	117.2 (3)
C14—C15—C16	110.3 (3)	C7—C6—C5A	122.4 (3)
C14—C15—C12	123.5 (3)	C7—C6—H6	118.8
C16—C15—C12	126.1 (3)	C5A—C6—H6	118.8
C17—C16—C15	116.0 (12)	C6—C7—C8	120.2 (3)
C15—C16—S17	115.3 (6)	C6—C7—H7	119.9
C17—C16—H16	122.0	C8—C7—H7	119.9
C15—C16—H16	122.0	C9—C8—C7	119.5 (3)
S17—C16—H16	122.7	C9—C8—H8	120.2
C11—C12—C15	126.9 (3)	C7—C8—H8	120.2
C11—C12—H12	116.6	C8—C9—C9A	121.9 (3)
C15—C12—H12	116.6	C8—C9—H9	119.0
C12—C11—C5	125.8 (3)	C9A—C9—H9	119.0
C12—C11—H11	117.1	C10—C9A—C9	121.9 (3)
C5—C11—H11	117.1	C10—C9A—C5A	119.4 (3)
C2—C1—C1A	121.8 (3)	C9—C9A—C5A	118.7 (3)
C2—C1—H1	119.1	C1A—C10—C9A	122.2 (3)
C1A—C1—H1	119.1	C1A—C10—H10	118.9
C1—C2—C3	120.2 (3)	C9A—C10—H10	118.9
C1—C2—H2	119.9	C10—C1A—C1	122.8 (3)
C3—C2—H2	119.9	C10—C1A—C4A	118.9 (2)
C4—C3—C2	120.0 (3)	C1—C1A—C4A	118.4 (3)
C4—C3—H3	120.0
C14—S13—C17—C16	1.6 (13)	C12—C11—C5—C5A	−66.9 (4)
C16—S17—C13—C14	0 (2)	C4A—C5—C5A—C6	−179.7 (2)
S17—C13—C14—C15	0 (2)	C11—C5—C5A—C6	2.0 (4)
C17—S13—C14—C15	−1.2 (8)	C4A—C5—C5A—C9A	−0.7 (3)
C13—C14—C15—C16	1.0 (15)	C11—C5—C5A—C9A	−179.0 (2)
S13—C14—C15—C16	0.4 (3)	C5—C5A—C6—C7	177.2 (3)
C13—C14—C15—C12	−179.2 (15)	C9A—C5A—C6—C7	−1.8 (4)
S13—C14—C15—C12	−179.7 (3)	C5A—C6—C7—C8	1.1 (4)
S13—C17—C16—C15	−1.7 (16)	C6—C7—C8—C9	0.5 (4)
C14—C15—C16—C17	1.0 (12)	C7—C8—C9—C9A	−1.3 (4)
C12—C15—C16—C17	−178.9 (11)	C8—C9—C9A—C10	−178.2 (3)
C14—C15—C16—S17	−1.3 (7)	C8—C9—C9A—C5A	0.5 (4)
C12—C15—C16—S17	178.9 (7)	C5—C5A—C9A—C10	0.7 (3)
C13—S17—C16—C15	1.0 (15)	C6—C5A—C9A—C10	179.8 (2)
C14—C15—C12—C11	172.7 (3)	C5—C5A—C9A—C9	−178.0 (2)
C16—C15—C12—C11	−7.5 (5)	C6—C5A—C9A—C9	1.0 (3)
C15—C12—C11—C5	−179.0 (2)	C9—C9A—C10—C1A	178.4 (2)
C1A—C1—C2—C3	−0.4 (4)	C5A—C9A—C10—C1A	−0.4 (4)
C1—C2—C3—C4	−0.2 (4)	C9A—C10—C1A—C1	179.5 (2)
C2—C3—C4—C4A	1.2 (4)	C9A—C10—C1A—C4A	−0.1 (4)
C3—C4—C4A—C5	178.8 (3)	C2—C1—C1A—C10	−179.4 (3)
C3—C4—C4A—C1A	−1.4 (4)	C2—C1—C1A—C4A	0.1 (4)
C4—C4A—C5—C5A	−180.0 (2)	C5—C4A—C1A—C10	0.1 (4)
C1A—C4A—C5—C5A	0.3 (4)	C4—C4A—C1A—C10	−179.7 (2)
C4—C4A—C5—C11	−1.6 (4)	C5—C4A—C1A—C1	−179.5 (2)
C1A—C4A—C5—C11	178.6 (2)	C4—C4A—C1A—C1	0.8 (3)
C12—C11—C5—C4A	114.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···S13^i	0.95	3.02	3.742 (6)	134
C8—H8···S13^ii	0.95	2.94	3.841 (5)	159
C2—H2···S17^iii	0.95	3.11	3.963 (16)	151
C14—H14···Cg4^ii	0.95	2.86	3.632	140
C8—H8···Cg1^iv	0.95	2.88	3.589	132

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1, −y+1/2, z−1/2; (iii) x+1, −y+1/2, z+1/2; (iv) x, −y+1/2, z+1/2.