(E)-3-Methyl­stilbene

In the title compound, C₁₅H₁₄, the two benzene rings and the C=C double bond are almost coplanar. In the crystal structure, mol­ecules are linked by inter­molecular C—H...π stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.066
• wR factor = 0.185
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C6     -   C7      ..      21.27 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C8     -   C9      ..      23.63 su

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   2 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 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, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(E)-3-Methylstilbene

Crystal data

C15H14	F(000) = 416
Mr = 194.26	Dx = 1.126 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.855 (1) Å	Cell parameters from 1554 reflections
b = 8.0709 (13) Å	θ = 2.7–21.1°
c = 24.255 (4) Å	µ = 0.06 mm^−1
β = 91.489 (3)°	T = 292 K
V = 1145.8 (3) Å^3	Block, colourless
Z = 4	0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1212 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 25.0°, θmin = 1.7°
φ and ω scans	h = −6→6
7927 measured reflections	k = −9→8
2005 independent reflections	l = −28→28

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.186	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0761P)^2 + 0.1919P] where P = (Fo^2 + 2Fc^2)/3
2005 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.10 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
C14	0.1080 (4)	0.2831 (3)	0.10101 (11)	0.0808 (7)
H14	0.2491	0.2351	0.1093	0.097*
C6	0.3554 (5)	0.3359 (3)	0.27899 (10)	0.0752 (7)
C9	−0.0110 (5)	0.3572 (3)	0.14275 (11)	0.0789 (7)
C1	0.5598 (5)	0.2602 (3)	0.29209 (12)	0.0871 (8)
H1	0.6302	0.1954	0.2658	0.105*
C8	0.0767 (5)	0.3732 (3)	0.20100 (14)	0.0979 (9)
H8	−0.0113	0.4354	0.2247	0.117*
C7	0.2588 (5)	0.3107 (3)	0.22128 (13)	0.0931 (9)
H7	0.3414	0.2423	0.1983	0.112*
C13	0.0238 (5)	0.2781 (3)	0.04737 (11)	0.0841 (8)
C5	0.2570 (4)	0.4326 (3)	0.31870 (12)	0.0860 (8)
H5	0.1189	0.4856	0.3108	0.103*
C10	−0.2212 (5)	0.4279 (3)	0.13022 (14)	0.0935 (8)
H10	−0.3042	0.4792	0.1576	0.112*
C3	0.5620 (6)	0.3746 (4)	0.38201 (12)	0.0977 (9)
H3	0.6310	0.3875	0.4167	0.117*
C12	−0.1850 (6)	0.3489 (4)	0.03640 (13)	0.0986 (9)
H12	−0.2452	0.3473	0.0005	0.118*
C2	0.6616 (5)	0.2783 (4)	0.34310 (13)	0.0970 (9)
H2	0.7990	0.2248	0.3513	0.116*
C11	−0.3059 (5)	0.4215 (4)	0.07702 (16)	0.1050 (10)
H11	−0.4482	0.4675	0.0686	0.126*
C4	0.3598 (6)	0.4517 (3)	0.36938 (12)	0.0971 (9)
H4	0.2915	0.5180	0.3956	0.116*
C15	0.1593 (6)	0.2023 (4)	0.00193 (12)	0.1190 (11)
H15A	0.2931	0.2680	−0.0040	0.179*
H15B	0.0672	0.1986	−0.0314	0.179*
H15C	0.2042	0.0919	0.0122	0.179*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C14	0.0713 (16)	0.0730 (16)	0.0982 (19)	−0.0104 (13)	0.0033 (14)	0.0091 (14)
C6	0.0874 (18)	0.0616 (15)	0.0771 (16)	−0.0123 (13)	0.0105 (14)	0.0015 (12)
C9	0.0819 (18)	0.0758 (17)	0.0793 (17)	−0.0227 (14)	0.0050 (14)	0.0058 (13)
C1	0.0873 (19)	0.0749 (17)	0.100 (2)	0.0029 (15)	0.0129 (15)	−0.0090 (14)
C8	0.0813 (19)	0.0754 (18)	0.138 (3)	−0.0059 (15)	0.0290 (17)	0.0033 (17)
C7	0.088 (2)	0.0667 (17)	0.125 (2)	−0.0015 (15)	0.0272 (17)	0.0051 (15)
C13	0.091 (2)	0.0666 (16)	0.095 (2)	−0.0204 (14)	0.0121 (16)	0.0085 (14)
C5	0.0832 (17)	0.0788 (18)	0.097 (2)	0.0075 (14)	0.0144 (15)	0.0108 (15)
C10	0.0768 (18)	0.0830 (19)	0.121 (2)	−0.0043 (15)	0.0153 (16)	0.0007 (16)
C3	0.127 (3)	0.0778 (19)	0.0873 (19)	−0.0064 (18)	−0.0071 (17)	−0.0012 (15)
C12	0.096 (2)	0.094 (2)	0.104 (2)	−0.0178 (18)	−0.0103 (18)	0.0185 (17)
C2	0.0892 (19)	0.0826 (19)	0.119 (2)	0.0033 (15)	−0.0068 (18)	0.0024 (17)
C11	0.0789 (19)	0.097 (2)	0.138 (3)	−0.0041 (16)	−0.012 (2)	0.025 (2)
C4	0.126 (2)	0.0770 (19)	0.089 (2)	0.0083 (17)	0.0282 (18)	−0.0021 (15)
C15	0.146 (3)	0.104 (2)	0.108 (2)	−0.023 (2)	0.027 (2)	−0.0085 (18)

Geometric parameters (Å, º)

C14—C13	1.380 (3)	C5—C4	1.363 (4)
C14—C9	1.380 (3)	C5—H5	0.9300
C14—H14	0.9300	C10—C11	1.371 (4)
C6—C1	1.373 (3)	C10—H10	0.9300
C6—C5	1.378 (3)	C3—C4	1.365 (4)
C6—C7	1.510 (4)	C3—C2	1.365 (4)
C9—C10	1.383 (4)	C3—H3	0.9300
C9—C8	1.496 (4)	C12—C11	1.361 (4)
C1—C2	1.367 (3)	C12—H12	0.9300
C1—H1	0.9300	C2—H2	0.9300
C8—C7	1.267 (4)	C11—H11	0.9300
C8—H8	0.9300	C4—H4	0.9300
C7—H7	0.9300	C15—H15A	0.9600
C13—C12	1.369 (4)	C15—H15B	0.9600
C13—C15	1.505 (4)	C15—H15C	0.9600
C13—C14—C9	122.0 (3)	C11—C10—C9	119.3 (3)
C13—C14—H14	119.0	C11—C10—H10	120.3
C9—C14—H14	119.0	C9—C10—H10	120.3
C1—C6—C5	117.9 (2)	C4—C3—C2	119.2 (3)
C1—C6—C7	117.2 (2)	C4—C3—H3	120.4
C5—C6—C7	124.8 (3)	C2—C3—H3	120.4
C14—C9—C10	118.7 (3)	C11—C12—C13	121.2 (3)
C14—C9—C8	124.2 (3)	C11—C12—H12	119.4
C10—C9—C8	117.0 (3)	C13—C12—H12	119.4
C2—C1—C6	121.2 (3)	C3—C2—C1	120.1 (3)
C2—C1—H1	119.4	C3—C2—H2	119.9
C6—C1—H1	119.4	C1—C2—H2	119.9
C7—C8—C9	126.7 (3)	C12—C11—C10	121.0 (3)
C7—C8—H8	116.7	C12—C11—H11	119.5
C9—C8—H8	116.7	C10—C11—H11	119.5
C8—C7—C6	126.7 (3)	C5—C4—C3	120.7 (3)
C8—C7—H7	116.7	C5—C4—H4	119.6
C6—C7—H7	116.7	C3—C4—H4	119.6
C12—C13—C14	117.8 (3)	C13—C15—H15A	109.5
C12—C13—C15	120.8 (3)	C13—C15—H15B	109.5
C14—C13—C15	121.4 (3)	H15A—C15—H15B	109.5
C4—C5—C6	120.8 (3)	C13—C15—H15C	109.5
C4—C5—H5	119.6	H15A—C15—H15C	109.5
C6—C5—H5	119.6	H15B—C15—H15C	109.5
C13—C14—C9—C10	0.2 (4)	C7—C6—C5—C4	−178.2 (2)
C13—C14—C9—C8	−177.0 (2)	C14—C9—C10—C11	0.4 (4)
C5—C6—C1—C2	0.8 (4)	C8—C9—C10—C11	177.8 (2)
C7—C6—C1—C2	179.0 (2)	C14—C13—C12—C11	−0.1 (4)
C14—C9—C8—C7	−6.4 (4)	C15—C13—C12—C11	−178.3 (2)
C10—C9—C8—C7	176.3 (3)	C4—C3—C2—C1	0.2 (4)
C9—C8—C7—C6	175.7 (2)	C6—C1—C2—C3	−0.8 (4)
C1—C6—C7—C8	−178.0 (3)	C13—C12—C11—C10	0.8 (4)
C5—C6—C7—C8	0.0 (4)	C9—C10—C11—C12	−0.9 (4)
C9—C14—C13—C12	−0.4 (4)	C6—C5—C4—C3	−0.4 (4)
C9—C14—C13—C15	177.8 (2)	C2—C3—C4—C5	0.4 (4)
C1—C6—C5—C4	−0.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg2^i	0.93	2.96	3.730 (3)	142

Symmetry code: (i) −x, y+1/2, −z+1/2.