4-Vinyl­benzoic acid and 9-vinyl­anthracene

The crystal structures of two styrene analogues, 4-vinyl­benzoic acid, C₉H₈O₂, (I), and 9-vinyl­anthracene, C₁₆H₁₂, (II), were determined by X-ray analyses at 108 and 293 K for (I) and at 123 and 293 K for (II). In (I), a pair of mol­ecules around an inversion center form a dimer connected by two carboxyl groups. The anthracene planes of two mol­ecules in (II) are antiparallel to each other around an inversion center. The vinyl group of (I) is almost coplanar with the phenyl ring, whereas the vinyl group of (II) is nearly perpendicular to the anthracene plane. In (I), the bond length of the vinyl group at 293 K is significantly shorter than that at 108 K [1.288 (2) versus 1.3248 (14) Å] suggesting a bias of the thermal motion, whereas the bond lengths are not so different between the two temperatures in (II) [1.3266 (15) versus 1.310 (2) Å].

Computing details

For all compounds, data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Rigaku, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1998); software used to prepare material for publication: SHELXL97.

(I_108K) 4-vinylbenzoic acid

Crystal data

C9H8O2	Dx = 1.357 Mg m^−3
Mr = 148.15	Melting point: 416 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.3945 (9) Å	Cell parameters from 9603 reflections
b = 6.4096 (7) Å	θ = 2.6–27.5°
c = 13.8798 (14) Å	µ = 0.10 mm^−1
β = 103.899 (4)°	T = 108 K
V = 724.94 (13) Å^3	Prism, colorless
Z = 4	0.50 × 0.40 × 0.30 mm
F(000) = 312

Data collection

Rigaku RAXIS-RAPID Imaging Plate diffractometer	1653 independent reflections
Radiation source: Rigaku ratating anode Ultrax18	1567 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 10 pixels mm^-1	θmax = 27.5°, θmin = 2.6°
Oscillation Photograph scans	h = −10→10
Absorption correction: multi-scan ABSCOR (Higashi, 1995)	k = −8→8
Tmin = 0.952, Tmax = 0.972	l = −18→17
6316 measured reflections

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)] = 0.039	Only H-atom coordinates refined
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0635P)^2 + 0.1621P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1653 reflections	Δρmax = 0.38 e Å^−3
129 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.045 (6)

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)
O1	0.69007 (10)	0.51215 (12)	0.47417 (6)	0.0283 (2)
HO1	0.627 (4)	0.592 (5)	0.503 (2)	0.034*	0.51 (2)
O2	0.50393 (9)	0.25638 (13)	0.44913 (6)	0.0257 (2)
HO2	0.452 (4)	0.335 (5)	0.475 (2)	0.031*	0.49 (2)
C1	0.98244 (11)	−0.06138 (15)	0.34383 (7)	0.0194 (2)
C2	1.02545 (11)	0.14209 (16)	0.37601 (7)	0.0214 (2)
H2	1.1320 (16)	0.195 (2)	0.3756 (10)	0.026*
C3	0.91517 (12)	0.26869 (16)	0.40778 (7)	0.0209 (2)
H3	0.9440 (16)	0.409 (2)	0.4296 (10)	0.025*
C4	0.75938 (11)	0.19427 (15)	0.40953 (7)	0.0188 (2)
C5	0.71481 (11)	−0.00747 (15)	0.37755 (7)	0.0201 (2)
H5	0.6087 (16)	−0.059 (2)	0.3796 (10)	0.024*
C6	0.82498 (12)	−0.13235 (15)	0.34379 (7)	0.0202 (2)
H6	0.7948 (16)	−0.273 (2)	0.3223 (10)	0.024*
C7	1.09875 (12)	−0.20408 (16)	0.31316 (7)	0.0226 (2)
H7	1.0512 (16)	−0.329 (2)	0.2846 (10)	0.027*
C8	1.25780 (13)	−0.17151 (18)	0.32344 (8)	0.0261 (3)
H8A	1.3130 (18)	−0.044 (2)	0.3520 (11)	0.031*
H8B	1.3260 (18)	−0.276 (2)	0.3040 (11)	0.031*
C9	0.64314 (12)	0.32874 (15)	0.44628 (7)	0.0198 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0320 (4)	0.0198 (4)	0.0366 (4)	−0.0013 (3)	0.0151 (3)	−0.0032 (3)
O2	0.0192 (4)	0.0282 (4)	0.0310 (4)	−0.0003 (3)	0.0083 (3)	−0.0032 (3)
C1	0.0184 (4)	0.0226 (5)	0.0168 (4)	0.0003 (3)	0.0034 (3)	−0.0001 (3)
C2	0.0180 (4)	0.0248 (5)	0.0212 (5)	−0.0038 (4)	0.0044 (3)	−0.0023 (4)
C3	0.0208 (5)	0.0212 (5)	0.0204 (5)	−0.0036 (4)	0.0045 (3)	−0.0023 (3)
C4	0.0185 (5)	0.0202 (5)	0.0173 (4)	0.0006 (3)	0.0032 (3)	0.0010 (3)
C5	0.0169 (4)	0.0216 (5)	0.0211 (4)	−0.0009 (3)	0.0032 (3)	0.0013 (3)
C6	0.0195 (4)	0.0191 (5)	0.0210 (4)	−0.0015 (3)	0.0028 (3)	−0.0004 (3)
C7	0.0224 (5)	0.0238 (5)	0.0217 (5)	0.0003 (4)	0.0054 (4)	−0.0032 (4)
C8	0.0224 (5)	0.0298 (5)	0.0270 (5)	0.0022 (4)	0.0077 (4)	−0.0020 (4)
C9	0.0203 (4)	0.0196 (5)	0.0193 (5)	0.0003 (3)	0.0044 (3)	0.0013 (3)

Geometric parameters (Å, º)

O1—HO1	0.89 (4)	C3—C4	1.3978 (13)
O1—C9	1.2703 (12)	C4—C5	1.3890 (13)
O2—HO2	0.80 (4)	C4—C9	1.4813 (13)
O2—C9	1.2667 (12)	C5—H5	0.958 (13)
C1—C2	1.3975 (14)	C5—C6	1.3869 (14)
C1—C6	1.3978 (13)	C6—H6	0.966 (14)
C1—C7	1.4734 (14)	C7—H7	0.939 (15)
C2—H2	0.958 (14)	C7—C8	1.3248 (14)
C2—C3	1.3806 (14)	C8—H8B	0.963 (15)
C3—H3	0.961 (14)	C8—H8A	0.975 (15)
HO1—O1—C9	119.6 (19)	H5—C5—C4	119.6 (8)
HO2—O2—C9	113 (2)	C6—C5—C4	119.67 (9)
C2—C1—C6	118.39 (9)	H6—C6—C5	119.8 (8)
C2—C1—C7	122.23 (9)	H6—C6—C1	118.8 (8)
C6—C1—C7	119.34 (9)	C5—C6—C1	121.28 (9)
H2—C2—C3	119.5 (8)	H7—C7—C8	119.7 (8)
H2—C2—C1	119.9 (8)	H7—C7—C1	114.1 (8)
C3—C2—C1	120.59 (9)	C8—C7—C1	126.28 (10)
H3—C3—C2	120.9 (8)	H8B—C8—H8A	116.3 (12)
H3—C3—C4	118.7 (8)	H8B—C8—C7	120.8 (9)
C2—C3—C4	120.46 (9)	H8A—C8—C7	123.0 (9)
C5—C4—C3	119.57 (9)	O2—C9—O1	123.38 (9)
C5—C4—C9	120.17 (8)	O2—C9—C4	119.12 (9)
C3—C4—C9	120.26 (9)	O1—C9—C4	117.50 (9)
H5—C5—C6	120.7 (8)
C8—C7—C1—C2	9.06 (16)	O2—C9—C4—C3	−178.52 (8)
O1—C9—C4—C3	0.99 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—HO1···O2^i	0.89 (4)	1.72 (4)	2.6114 (11)	176 (3)
O2—HO2···O1^i	0.80 (4)	1.82 (4)	2.6114 (11)	172 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

(I_293K) 4-vinylbenzoic acid

Crystal data

C9H8O2	Dx = 1.304 Mg m^−3
Mr = 148.15	Melting point: 416 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.2876 (16) Å	Cell parameters from 8554 reflections
b = 6.5504 (12) Å	θ = 1.5–27.5°
c = 14.247 (2) Å	µ = 0.09 mm^−1
β = 102.651 (8)°	T = 293 K
V = 754.7 (2) Å^3	Prism, colorless
Z = 4	0.50 × 0.40 × 0.30 mm
F(000) = 312

Data collection

Rigaku RAXIS-RAPID Imaging Plate diffractometer	1718 independent reflections
Radiation source: Rigaku ratating anode Ultrax18	1396 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
Detector resolution: 10 pixels mm^-1	θmax = 27.5°, θmin = 2.9°
Oscillation Photograph scans	h = −10→10
Absorption correction: multi-scan ABSCOR (Higashi, 1995)	k = −7→8
Tmin = 0.982, Tmax = 0.991	l = −18→18
5865 measured reflections

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)] = 0.051	Only H-atom coordinates refined
wR(F^2) = 0.139	w = 1/[σ^2(Fo^2) + (0.0661P)^2 + 0.0872P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1718 reflections	Δρmax = 0.18 e Å^−3
129 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.070 (11)

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)
O1	0.68953 (16)	0.50975 (19)	0.47359 (11)	0.0823 (4)
HO1	0.636 (7)	0.576 (8)	0.507 (3)	0.099*	0.53 (4)
O2	0.50421 (13)	0.26183 (19)	0.44964 (9)	0.0748 (4)
HO2	0.443 (7)	0.346 (8)	0.474 (3)	0.090*	0.47 (4)
C1	0.98094 (16)	−0.0523 (2)	0.34578 (10)	0.0592 (4)
C2	1.02382 (18)	0.1451 (3)	0.37687 (11)	0.0668 (4)
H2	1.128 (2)	0.196 (3)	0.3759 (13)	0.080*
C3	0.91465 (19)	0.2704 (3)	0.40793 (11)	0.0652 (4)
H3	0.945 (2)	0.404 (3)	0.4317 (13)	0.078*
C4	0.75887 (16)	0.1997 (2)	0.41002 (9)	0.0565 (4)
C5	0.71478 (17)	0.0041 (2)	0.37877 (11)	0.0615 (4)
H5	0.607 (2)	−0.045 (3)	0.3777 (12)	0.074*
C6	0.82395 (18)	−0.1187 (2)	0.34586 (11)	0.0633 (4)
H6	0.794 (2)	−0.256 (3)	0.3244 (12)	0.076*
C7	1.0970 (2)	−0.1924 (3)	0.31540 (12)	0.0726 (5)
H7	1.053 (2)	−0.321 (3)	0.2899 (14)	0.087*
C8	1.2534 (2)	−0.1638 (4)	0.32423 (15)	0.0854 (6)
H8A	1.309 (3)	−0.033 (3)	0.3567 (16)	0.103*
H8B	1.312 (3)	−0.273 (3)	0.3020 (16)	0.103*
C9	0.64365 (17)	0.3318 (2)	0.44629 (10)	0.0599 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0794 (8)	0.0614 (7)	0.1171 (10)	−0.0111 (6)	0.0456 (7)	−0.0109 (6)
O2	0.0557 (6)	0.0739 (8)	0.0991 (9)	−0.0073 (5)	0.0266 (5)	−0.0108 (6)
C1	0.0544 (7)	0.0691 (9)	0.0543 (7)	−0.0025 (6)	0.0125 (5)	−0.0005 (6)
C2	0.0516 (7)	0.0827 (11)	0.0688 (9)	−0.0153 (7)	0.0189 (6)	−0.0087 (7)
C3	0.0611 (8)	0.0679 (9)	0.0692 (9)	−0.0155 (7)	0.0204 (6)	−0.0094 (7)
C4	0.0529 (7)	0.0598 (8)	0.0571 (7)	−0.0038 (6)	0.0127 (5)	0.0033 (6)
C5	0.0492 (7)	0.0603 (8)	0.0751 (9)	−0.0072 (6)	0.0140 (6)	0.0026 (6)
C6	0.0580 (8)	0.0593 (8)	0.0723 (9)	−0.0065 (6)	0.0135 (6)	−0.0025 (7)
C7	0.0659 (9)	0.0822 (11)	0.0715 (9)	−0.0042 (8)	0.0186 (7)	−0.0102 (8)
C8	0.0665 (10)	0.1012 (14)	0.0932 (12)	0.0028 (10)	0.0274 (8)	−0.0135 (11)
C9	0.0563 (7)	0.0588 (8)	0.0660 (8)	−0.0053 (6)	0.0166 (6)	0.0028 (6)

Geometric parameters (Å, º)

O1—HO1	0.83 (6)	C3—C4	1.3780 (19)
O1—C9	1.2611 (19)	C4—C5	1.379 (2)
O2—HO2	0.87 (7)	C4—C9	1.464 (2)
O2—C9	1.2537 (17)	C5—H5	0.949 (18)
C1—C6	1.372 (2)	C5—C6	1.368 (2)
C1—C2	1.388 (2)	C6—H6	0.966 (17)
C1—C7	1.462 (2)	C7—H7	0.96 (2)
C2—H2	0.930 (19)	C7—C8	1.288 (2)
C2—C3	1.365 (2)	C8—H8B	0.96 (2)
C3—H3	0.95 (2)	C8—H8A	1.03 (2)
HO1—O1—C9	120 (3)	H5—C5—C4	120.1 (11)
HO2—O2—C9	114 (3)	C6—C5—C4	120.56 (13)
C6—C1—C2	118.13 (14)	H6—C6—C5	120.7 (10)
C6—C1—C7	119.16 (15)	H6—C6—C1	118.4 (10)
C2—C1—C7	122.70 (14)	C5—C6—C1	120.85 (14)
H2—C2—C3	118.2 (12)	H7—C7—C8	117.0 (12)
H2—C2—C1	120.3 (12)	H7—C7—C1	116.5 (12)
C3—C2—C1	121.49 (14)	C8—C7—C1	126.40 (18)
H3—C3—C2	121.9 (11)	H8B—C8—H8A	123.8 (19)
H3—C3—C4	118.3 (11)	H8B—C8—C7	115.7 (14)
C2—C3—C4	119.70 (15)	H8A—C8—C7	120.4 (12)
C3—C4—C5	119.24 (14)	O2—C9—O1	122.98 (14)
C3—C4—C9	119.72 (14)	O2—C9—C4	118.39 (14)
C5—C4—C9	121.04 (12)	O1—C9—C4	118.63 (13)
H5—C5—C6	119.3 (10)
C8—C7—C1—C2	9.1 (3)	O2—C9—C4—C3	−178.24 (13)
O1—C9—C4—C3	1.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—HO1···O2^i	0.83 (6)	1.79 (6)	2.6043 (17)	166 (5)
O2—HO2···O1^i	0.87 (7)	1.74 (7)	2.6043 (17)	173 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.

(II_123K) 9-vinylanthracene

Crystal data

C16H12	Dx = 1.269 Mg m^−3
Mr = 204.26	Melting point: 338 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.3213 (3) Å	Cell parameters from 12209 reflections
b = 13.6798 (4) Å	θ = 2.7–27.5°
c = 8.8957 (3) Å	µ = 0.07 mm^−1
β = 109.467 (1)°	T = 123 K
V = 1069.48 (6) Å^3	Prism, yellow
Z = 4	0.20 × 0.20 × 0.20 mm
F(000) = 432

Data collection

Rigaku RAXIS-RAPID Imaging Plate diffractometer	2459 independent reflections
Radiation source: Rigaku ratating anode Ultrax18	2231 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 10 pixels mm^-1	θmax = 27.5°, θmin = 2.3°
Oscillation Photograph scans	h = −12→12
Absorption correction: multi-scan ABSCOR (Higashi, 1995)	k = −17→17
Tmin = 0.975, Tmax = 0.986	l = −11→11
10703 measured reflections

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)] = 0.041	Only H-atom coordinates refined
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0626P)^2 + 0.2677P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2459 reflections	Δρmax = 0.31 e Å^−3
182 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.062 (6)

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
C1	0.00703 (11)	0.84752 (7)	0.04917 (11)	0.0174 (2)
C2	0.09567 (11)	0.91479 (7)	0.16326 (11)	0.0174 (2)
C3	0.02333 (11)	0.97660 (7)	0.24759 (11)	0.0186 (2)
C4	−0.13356 (11)	0.97049 (7)	0.21476 (11)	0.0199 (2)
H4	−0.1818 (14)	1.0139 (10)	0.2736 (15)	0.024*
C5	−0.22284 (11)	0.90650 (7)	0.09986 (11)	0.0186 (2)
C6	−0.15251 (11)	0.84437 (7)	0.01435 (11)	0.0175 (2)
C7	0.07801 (11)	0.77923 (7)	−0.03495 (12)	0.0212 (2)
H7	0.0362 (14)	0.7799 (9)	−0.1535 (16)	0.025*
C8	0.18792 (12)	0.71643 (8)	0.03694 (13)	0.0252 (3)
H8A	0.2284 (15)	0.7129 (10)	0.1544 (17)	0.030*
H8B	0.2292 (15)	0.6710 (10)	−0.0237 (16)	0.030*
C9	0.25644 (11)	0.92662 (7)	0.19731 (11)	0.0200 (2)
H9	0.3070 (14)	0.8881 (10)	0.1378 (15)	0.024*
C10	0.33823 (11)	0.99190 (8)	0.30849 (12)	0.0228 (2)
H10	0.4481 (15)	1.0015 (10)	0.3274 (15)	0.027*
C11	0.26629 (12)	1.05084 (8)	0.39421 (12)	0.0243 (2)
H11	0.3270 (15)	1.0978 (10)	0.4729 (16)	0.029*
C12	0.11382 (12)	1.04364 (7)	0.36417 (11)	0.0223 (2)
H12	0.0618 (14)	1.0853 (10)	0.4200 (16)	0.027*
C13	−0.24862 (11)	0.78011 (7)	−0.10311 (12)	0.0212 (2)
H13	−0.2028 (14)	0.7375 (10)	−0.1619 (16)	0.025*
C14	−0.40229 (12)	0.77840 (8)	−0.13440 (13)	0.0247 (2)
H14	−0.4669 (15)	0.7358 (10)	−0.2178 (16)	0.030*
C15	−0.47103 (12)	0.83928 (8)	−0.04860 (13)	0.0251 (2)
H15	−0.5807 (16)	0.8363 (10)	−0.0717 (16)	0.030*
C16	−0.38401 (11)	0.90093 (8)	0.06536 (12)	0.0227 (2)
H16	−0.4304 (15)	0.9431 (10)	0.1245 (16)	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0204 (5)	0.0166 (4)	0.0158 (4)	0.0022 (3)	0.0067 (4)	0.0020 (3)
C2	0.0201 (5)	0.0167 (4)	0.0152 (4)	0.0017 (3)	0.0058 (3)	0.0027 (3)
C3	0.0238 (5)	0.0168 (4)	0.0149 (4)	0.0024 (3)	0.0063 (4)	0.0021 (3)
C4	0.0241 (5)	0.0195 (5)	0.0176 (4)	0.0047 (4)	0.0090 (4)	0.0015 (3)
C5	0.0209 (5)	0.0182 (4)	0.0179 (4)	0.0032 (3)	0.0080 (4)	0.0044 (3)
C6	0.0202 (5)	0.0160 (4)	0.0164 (4)	0.0015 (3)	0.0063 (4)	0.0028 (3)
C7	0.0208 (5)	0.0228 (5)	0.0205 (5)	−0.0011 (4)	0.0078 (4)	−0.0044 (4)
C8	0.0232 (5)	0.0223 (5)	0.0305 (6)	0.0005 (4)	0.0095 (4)	−0.0060 (4)
C9	0.0211 (5)	0.0204 (5)	0.0188 (4)	0.0011 (4)	0.0073 (4)	0.0016 (4)
C10	0.0214 (5)	0.0232 (5)	0.0215 (5)	−0.0019 (4)	0.0043 (4)	0.0018 (4)
C11	0.0287 (5)	0.0208 (5)	0.0197 (5)	−0.0021 (4)	0.0031 (4)	−0.0024 (4)
C12	0.0289 (5)	0.0195 (5)	0.0175 (5)	0.0029 (4)	0.0062 (4)	−0.0010 (4)
C13	0.0230 (5)	0.0186 (5)	0.0215 (5)	−0.0005 (4)	0.0069 (4)	−0.0002 (4)
C14	0.0234 (5)	0.0230 (5)	0.0253 (5)	−0.0036 (4)	0.0052 (4)	−0.0002 (4)
C15	0.0185 (5)	0.0295 (5)	0.0276 (5)	0.0002 (4)	0.0080 (4)	0.0048 (4)
C16	0.0212 (5)	0.0255 (5)	0.0234 (5)	0.0040 (4)	0.0102 (4)	0.0041 (4)

Geometric parameters (Å, º)

C1—C2	1.4145 (13)	C8—H8A	0.987 (14)
C1—C6	1.4150 (13)	C9—H9	0.972 (13)
C1—C7	1.4834 (13)	C9—C10	1.3617 (14)
C2—C9	1.4357 (13)	C10—H10	0.990 (14)
C2—C3	1.4386 (13)	C10—C11	1.4220 (15)
C3—C4	1.3951 (14)	C11—H11	0.979 (14)
C3—C12	1.4299 (13)	C11—C12	1.3594 (15)
C4—H4	0.993 (13)	C12—H12	0.983 (13)
C4—C5	1.3916 (14)	C13—H13	0.972 (14)
C5—C16	1.4316 (13)	C13—C14	1.3652 (14)
C5—C6	1.4364 (13)	C14—H14	0.977 (14)
C6—C13	1.4294 (13)	C14—C15	1.4187 (15)
C7—H7	0.995 (13)	C15—H15	0.974 (14)
C7—C8	1.3266 (15)	C15—C16	1.3597 (15)
C8—H8B	0.982 (14)	C16—H16	0.974 (14)
C2—C1—C6	119.79 (8)	H9—C9—C10	119.6 (7)
C2—C1—C7	121.31 (8)	H9—C9—C2	119.0 (7)
C6—C1—C7	118.90 (8)	C10—C9—C2	121.30 (9)
C1—C2—C9	122.94 (9)	H10—C10—C9	120.5 (8)
C1—C2—C3	119.56 (9)	H10—C10—C11	118.7 (8)
C9—C2—C3	117.48 (9)	C9—C10—C11	120.76 (9)
C4—C3—C12	120.93 (9)	H11—C11—C12	120.3 (8)
C4—C3—C2	119.76 (9)	H11—C11—C10	119.5 (8)
C12—C3—C2	119.30 (9)	C12—C11—C10	120.16 (9)
H4—C4—C5	119.9 (7)	H12—C12—C11	121.2 (8)
H4—C4—C3	118.7 (7)	H12—C12—C3	117.8 (8)
C5—C4—C3	121.33 (9)	C11—C12—C3	120.96 (9)
C4—C5—C16	121.26 (9)	H13—C13—C14	120.0 (8)
C4—C5—C6	119.63 (9)	H13—C13—C6	118.8 (8)
C16—C5—C6	119.11 (9)	C14—C13—C6	121.26 (9)
C1—C6—C13	122.39 (9)	H14—C14—C13	120.3 (8)
C1—C6—C5	119.86 (9)	H14—C14—C15	118.9 (8)
C13—C6—C5	117.74 (9)	C13—C14—C15	120.77 (10)
H7—C7—C8	118.9 (7)	H15—C15—C16	120.5 (8)
H7—C7—C1	116.5 (7)	H15—C15—C14	119.5 (8)
C8—C7—C1	124.56 (9)	C16—C15—C14	120.07 (9)
H8B—C8—H8A	118.0 (11)	H16—C16—C15	120.5 (8)
H8B—C8—C7	121.8 (8)	H16—C16—C5	118.4 (8)
H8A—C8—C7	120.2 (8)	C15—C16—C5	121.03 (9)
C2—C1—C7—C8	56.15 (14)

(II_293K) 9-vinylanthracene

Crystal data

C16H12	Dx = 1.225 Mg m^−3
Mr = 204.26	Melting point: 338 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.3873 (5) Å	Cell parameters from 10475 reflections
b = 13.9756 (10) Å	θ = 2.7–27.5°
c = 8.9889 (7) Å	µ = 0.07 mm^−1
β = 110.066 (1)°	T = 293 K
V = 1107.70 (13) Å^3	Prism, yellow
Z = 4	0.40 × 0.30 × 0.30 mm
F(000) = 432

Data collection

Rigaku RAXIS-RAPID Imaging Plate diffractometer	2538 independent reflections
Radiation source: Rigaku ratating anode Ultrax18	2010 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 10 pixels mm^-1	θmax = 27.5°, θmin = 2.7°
Oscillation Photograph scans	h = −12→11
Absorption correction: multi-scan ABSCOR (Higashi, 1995)	k = −18→18
Tmin = 0.968, Tmax = 0.976	l = −11→11
10621 measured reflections

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)] = 0.056	Only H-atom coordinates refined
wR(F^2) = 0.151	w = 1/[σ^2(Fo^2) + (0.0685P)^2 + 0.1928P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2538 reflections	Δρmax = 0.25 e Å^−3
182 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.109 (10)

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
C1	0.00702 (15)	0.84764 (9)	0.05231 (15)	0.0430 (3)
C2	0.09515 (16)	0.91436 (9)	0.16424 (15)	0.0429 (3)
C3	0.02277 (17)	0.97528 (10)	0.24666 (16)	0.0470 (4)
C4	−0.13200 (18)	0.96879 (11)	0.21364 (17)	0.0512 (4)
H4	−0.1780 (18)	1.0117 (13)	0.270 (2)	0.061*
C5	−0.22145 (16)	0.90549 (10)	0.10070 (16)	0.0473 (4)
C6	−0.15131 (16)	0.84395 (9)	0.01761 (16)	0.0445 (3)
C7	0.07746 (17)	0.78048 (11)	−0.03034 (19)	0.0533 (4)
H7	0.0357 (19)	0.7839 (12)	−0.149 (2)	0.064*
C8	0.18362 (19)	0.71803 (12)	0.0388 (2)	0.0633 (5)
H8A	0.226 (2)	0.7160 (14)	0.160 (3)	0.076*
H8B	0.223 (2)	0.6742 (15)	−0.021 (2)	0.076*
C9	0.25412 (17)	0.92666 (11)	0.19802 (17)	0.0502 (4)
H9	0.3049 (19)	0.8860 (13)	0.141 (2)	0.060*
C10	0.33499 (19)	0.99125 (12)	0.30695 (19)	0.0599 (4)
H10	0.443 (2)	1.0013 (14)	0.324 (2)	0.072*
C11	0.2637 (2)	1.04895 (12)	0.3903 (2)	0.0649 (5)
H11	0.323 (2)	1.0932 (15)	0.463 (2)	0.078*
C12	0.1137 (2)	1.04172 (11)	0.36089 (18)	0.0582 (4)
H12	0.062 (2)	1.0826 (13)	0.415 (2)	0.070*
C13	−0.24718 (18)	0.78051 (11)	−0.09750 (19)	0.0551 (4)
H13	−0.199 (2)	0.7372 (13)	−0.151 (2)	0.066*
C14	−0.3991 (2)	0.77874 (13)	−0.1286 (2)	0.0657 (5)
H14	−0.462 (2)	0.7370 (15)	−0.211 (2)	0.079*
C15	−0.4670 (2)	0.83883 (14)	−0.0457 (2)	0.0682 (5)
H15	−0.576 (2)	0.8356 (15)	−0.072 (2)	0.082*
C16	−0.38105 (18)	0.89963 (13)	0.0657 (2)	0.0599 (4)
H16	−0.426 (2)	0.9435 (14)	0.124 (2)	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0504 (7)	0.0431 (7)	0.0382 (7)	0.0045 (5)	0.0185 (6)	0.0037 (5)
C2	0.0512 (7)	0.0435 (7)	0.0351 (6)	0.0039 (5)	0.0162 (5)	0.0051 (5)
C3	0.0603 (9)	0.0449 (7)	0.0359 (7)	0.0070 (6)	0.0165 (6)	0.0040 (5)
C4	0.0617 (9)	0.0522 (8)	0.0448 (8)	0.0142 (7)	0.0248 (7)	0.0027 (6)
C5	0.0525 (8)	0.0493 (7)	0.0439 (7)	0.0091 (6)	0.0216 (6)	0.0092 (6)
C6	0.0507 (7)	0.0433 (7)	0.0416 (7)	0.0037 (6)	0.0184 (6)	0.0064 (5)
C7	0.0535 (8)	0.0603 (9)	0.0485 (8)	0.0021 (7)	0.0207 (6)	−0.0105 (7)
C8	0.0580 (9)	0.0578 (9)	0.0747 (11)	0.0067 (7)	0.0237 (8)	−0.0157 (8)
C9	0.0519 (8)	0.0537 (8)	0.0463 (8)	0.0005 (6)	0.0185 (6)	0.0030 (6)
C10	0.0565 (9)	0.0624 (9)	0.0552 (9)	−0.0066 (7)	0.0119 (7)	0.0016 (7)
C11	0.0759 (11)	0.0566 (9)	0.0513 (9)	−0.0054 (8)	0.0079 (8)	−0.0086 (7)
C12	0.0737 (11)	0.0531 (8)	0.0440 (8)	0.0066 (7)	0.0152 (7)	−0.0060 (6)
C13	0.0570 (9)	0.0518 (8)	0.0563 (9)	−0.0012 (7)	0.0191 (7)	−0.0021 (7)
C14	0.0584 (9)	0.0661 (10)	0.0671 (11)	−0.0104 (8)	0.0146 (8)	−0.0012 (8)
C15	0.0498 (9)	0.0813 (12)	0.0741 (12)	−0.0014 (8)	0.0218 (8)	0.0089 (9)
C16	0.0546 (9)	0.0696 (10)	0.0617 (10)	0.0108 (7)	0.0277 (8)	0.0096 (8)

Geometric parameters (Å, º)

C1—C6	1.411 (2)	C8—H8A	1.02 (2)
C1—C2	1.4124 (19)	C9—H9	0.990 (18)
C1—C7	1.4857 (19)	C9—C10	1.356 (2)
C2—C9	1.428 (2)	C10—H10	0.98 (2)
C2—C3	1.4425 (19)	C10—C11	1.416 (3)
C3—C4	1.382 (2)	C11—H11	0.94 (2)
C3—C12	1.430 (2)	C11—C12	1.344 (3)
C4—H4	0.974 (18)	C12—H12	0.979 (19)
C4—C5	1.390 (2)	C13—H13	0.98 (2)
C5—C16	1.424 (2)	C13—C14	1.356 (2)
C5—C6	1.4382 (19)	C14—H14	0.97 (2)
C6—C13	1.424 (2)	C14—C15	1.412 (3)
C7—H7	1.005 (19)	C15—H15	0.97 (2)
C7—C8	1.310 (2)	C15—C16	1.349 (3)
C8—H8B	0.97 (2)	C16—H16	0.99 (2)
C6—C1—C2	119.79 (12)	H9—C9—C10	120.4 (10)
C6—C1—C7	118.82 (12)	H9—C9—C2	118.3 (10)
C2—C1—C7	121.39 (13)	C10—C9—C2	121.26 (15)
C1—C2—C9	123.03 (13)	H10—C10—C9	119.8 (11)
C1—C2—C3	119.44 (13)	H10—C10—C11	119.2 (11)
C9—C2—C3	117.51 (13)	C9—C10—C11	120.80 (16)
C4—C3—C12	121.43 (13)	H11—C11—C12	121.5 (13)
C4—C3—C2	119.77 (13)	H11—C11—C10	118.0 (13)
C12—C3—C2	118.80 (14)	C12—C11—C10	120.43 (15)
H4—C4—C3	117.9 (10)	H12—C12—C11	121.6 (11)
H4—C4—C5	120.3 (10)	H12—C12—C3	117.2 (11)
C3—C4—C5	121.69 (13)	C11—C12—C3	121.16 (15)
C4—C5—C16	121.60 (14)	H13—C13—C14	121.4 (10)
C4—C5—C6	119.36 (13)	H13—C13—C6	117.4 (10)
C16—C5—C6	119.04 (14)	C14—C13—C6	121.26 (16)
C1—C6—C13	122.59 (13)	H14—C14—C13	119.7 (12)
C1—C6—C5	119.90 (13)	H14—C14—C15	119.4 (12)
C13—C6—C5	117.51 (13)	C13—C14—C15	120.91 (17)
H7—C7—C8	119.5 (10)	H15—C15—C16	121.5 (12)
H7—C7—C1	115.1 (10)	H15—C15—C14	118.3 (12)
C8—C7—C1	125.46 (15)	C16—C15—C14	120.21 (16)
H8B—C8—H8A	119.4 (16)	H16—C16—C15	121.8 (11)
H8B—C8—C7	121.9 (11)	H16—C16—C5	117.2 (11)
H8A—C8—C7	118.7 (11)	C15—C16—C5	121.06 (16)
C2—C1—C7—C8	58.4 (2)