2-(4-Methoxy-phen-yl)-1H-indene.

Excluding four H atoms, the molecule of the title compound, C(16)H(14)O, is almost planar, with an r.m.s. deviation of 0.0801 (2) Å. Due to p-π conjugation, the lengths of the two single bonds attached to the O atom are significantly different.

Related literature

For related literature, see: Rayabarapu et al. (2003 ▶); Senanayake et al. (1995 ▶).

Experimental

Crystal data

C16H14O

M = 222.27

Monoclinic,

a = 5.8347 (8) Å

b = 7.5584 (10) Å

c = 26.135 (4) Å

β = 92.772 (11)°

V = 1151.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 113 (2) K

0.34 × 0.32 × 0.12 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Molecular Structure Corporation & Rigaku, 1999 ▶) T min = 0.974, T max = 0.991

10940 measured reflections

2724 independent reflections

2360 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.135

S = 1.10

2724 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 1999 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019776/wk2085sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019776/wk2085Isup2.hkl

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

C16H14O	F000 = 472
Mr = 222.27	Dx = 1.282 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 2782 reflections
a = 5.8347 (8) Å	θ = 2.8–27.9º
b = 7.5584 (10) Å	µ = 0.08 mm−1
c = 26.135 (4) Å	T = 113 (2) K
β = 92.772 (11)º	Plate, colourless
V = 1151.3 (3) Å3	0.34 × 0.32 × 0.12 mm
Z = 4

Rigaku Saturn diffractometer	2724 independent reflections
Radiation source: rotating anode	2360 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.038
Detector resolution: 7.31 pixels mm-1	θmax = 27.9º
T = 113(2) K	θmin = 2.8º
ω scans	h = −7→7
Absorption correction: multi-scan(CrystalClear; Molecular Structure Corporation & Rigaku, 1999)	k = −9→9
Tmin = 0.974, Tmax = 0.991	l = −34→34
10940 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0654P)2 + 0.4321P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2724 reflections	Δρmax = 0.32 e Å−3
155 parameters	Δρmin = −0.39 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
O1	0.06468 (18)	0.38400 (14)	0.43568 (4)	0.0246 (3)
C1	0.0999 (2)	0.37824 (18)	0.38417 (5)	0.0196 (3)
C2	−0.0458 (2)	0.29441 (18)	0.34780 (5)	0.0209 (3)
H2	−0.1824	0.2384	0.3578	0.025*
C3	0.0118 (2)	0.29399 (18)	0.29665 (5)	0.0205 (3)
H3	−0.0875	0.2366	0.2720	0.025*
C4	0.2110 (2)	0.37525 (17)	0.28040 (5)	0.0188 (3)
C5	0.3523 (2)	0.46050 (18)	0.31800 (5)	0.0207 (3)
H5	0.4884	0.5177	0.3082	0.025*
C6	0.2972 (2)	0.46277 (18)	0.36889 (5)	0.0217 (3)
H6	0.3944	0.5223	0.3935	0.026*
C7	0.2705 (2)	0.37168 (17)	0.22661 (5)	0.0191 (3)
C8	0.4701 (2)	0.44705 (18)	0.20655 (5)	0.0203 (3)
H8	0.5885	0.5082	0.2255	0.024*
C9	0.4594 (2)	0.41280 (18)	0.15079 (5)	0.0193 (3)
C10	0.6102 (3)	0.45594 (19)	0.11311 (5)	0.0234 (3)
H10	0.7468	0.5203	0.1215	0.028*
C11	0.5577 (3)	0.40313 (19)	0.06279 (6)	0.0251 (3)
H11	0.6602	0.4309	0.0368	0.030*
C12	0.3566 (3)	0.31006 (19)	0.05014 (5)	0.0246 (3)
H12	0.3239	0.2747	0.0157	0.030*
C13	0.2030 (3)	0.26833 (18)	0.08766 (5)	0.0220 (3)
H13	0.0648	0.2064	0.0790	0.026*
C14	0.2559 (2)	0.31909 (17)	0.13805 (5)	0.0188 (3)
C15	0.1310 (2)	0.29032 (18)	0.18543 (5)	0.0197 (3)
H15A	−0.0226	0.3461	0.1824	0.024*
H15B	0.1118	0.1623	0.1919	0.024*
C16	−0.1393 (3)	0.3029 (2)	0.45282 (6)	0.0311 (4)
H16A	−0.1495	0.3227	0.4897	0.047*
H16B	−0.1347	0.1755	0.4460	0.047*
H16C	−0.2736	0.3548	0.4345	0.047*

	U11	U22	U33	U12	U13	U23
O1	0.0271 (6)	0.0282 (6)	0.0184 (5)	−0.0015 (4)	0.0008 (4)	0.0018 (4)
C1	0.0221 (7)	0.0180 (6)	0.0187 (6)	0.0040 (5)	−0.0003 (5)	0.0017 (5)
C2	0.0195 (7)	0.0196 (7)	0.0237 (7)	−0.0020 (5)	0.0006 (5)	0.0014 (5)
C3	0.0205 (7)	0.0188 (6)	0.0219 (7)	−0.0012 (5)	−0.0019 (5)	−0.0009 (5)
C4	0.0197 (7)	0.0141 (6)	0.0224 (7)	0.0037 (5)	0.0004 (5)	0.0003 (5)
C5	0.0179 (7)	0.0195 (7)	0.0247 (7)	−0.0006 (5)	0.0011 (5)	−0.0011 (5)
C6	0.0205 (7)	0.0204 (7)	0.0240 (7)	0.0004 (5)	−0.0025 (5)	−0.0020 (5)
C7	0.0216 (7)	0.0139 (6)	0.0220 (7)	0.0030 (5)	0.0012 (5)	−0.0006 (5)
C8	0.0181 (7)	0.0212 (7)	0.0215 (7)	−0.0014 (5)	−0.0001 (5)	−0.0021 (5)
C9	0.0193 (7)	0.0158 (6)	0.0225 (7)	0.0011 (5)	−0.0001 (5)	−0.0001 (5)
C10	0.0229 (7)	0.0209 (7)	0.0267 (7)	−0.0024 (6)	0.0026 (6)	0.0015 (5)
C11	0.0280 (8)	0.0241 (7)	0.0235 (7)	0.0019 (6)	0.0060 (6)	0.0053 (6)
C12	0.0311 (8)	0.0230 (7)	0.0198 (7)	0.0021 (6)	0.0006 (6)	0.0011 (5)
C13	0.0242 (8)	0.0200 (7)	0.0216 (7)	−0.0013 (6)	−0.0018 (5)	0.0005 (5)
C14	0.0191 (7)	0.0157 (6)	0.0216 (7)	0.0016 (5)	0.0002 (5)	0.0011 (5)
C15	0.0192 (7)	0.0185 (6)	0.0211 (6)	0.0008 (5)	−0.0008 (5)	−0.0004 (5)
C16	0.0332 (9)	0.0371 (9)	0.0234 (7)	−0.0048 (7)	0.0043 (6)	0.0049 (6)

O1—C1	1.3724 (16)	C9—C10	1.391 (2)
O1—C16	1.4301 (19)	C9—C14	1.409 (2)
C1—C6	1.392 (2)	C10—C11	1.394 (2)
C1—C2	1.3963 (19)	C10—H10	0.9500
C2—C3	1.394 (2)	C11—C12	1.394 (2)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.399 (2)	C12—C13	1.397 (2)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.4078 (19)	C13—C14	1.3919 (19)
C4—C7	1.4645 (19)	C13—H13	0.9500
C5—C6	1.384 (2)	C14—C15	1.4829 (19)
C5—H5	0.9500	C15—H15A	0.9900
C6—H6	0.9500	C15—H15B	0.9900
C7—C8	1.419 (2)	C16—H16A	0.9800
C7—C15	1.4542 (19)	C16—H16B	0.9800
C8—C9	1.4785 (19)	C16—H16C	0.9800
C8—H8	0.9500
C1—O1—C16	117.40 (12)	C9—C10—C11	118.88 (14)
O1—C1—C6	115.60 (12)	C9—C10—H10	120.6
O1—C1—C2	124.55 (13)	C11—C10—H10	120.6
C6—C1—C2	119.85 (13)	C12—C11—C10	120.83 (14)
C3—C2—C1	119.13 (13)	C12—C11—H11	119.6
C3—C2—H2	120.4	C10—C11—H11	119.6
C1—C2—H2	120.4	C11—C12—C13	120.59 (13)
C2—C3—C4	122.18 (13)	C11—C12—H12	119.7
C2—C3—H3	118.9	C13—C12—H12	119.7
C4—C3—H3	118.9	C14—C13—C12	118.78 (14)
C3—C4—C5	117.14 (13)	C14—C13—H13	120.6
C3—C4—C7	121.50 (12)	C12—C13—H13	120.6
C5—C4—C7	121.36 (13)	C13—C14—C9	120.54 (13)
C6—C5—C4	121.43 (13)	C13—C14—C15	130.85 (13)
C6—C5—H5	119.3	C9—C14—C15	108.60 (12)
C4—C5—H5	119.3	C7—C15—C14	106.02 (12)
C5—C6—C1	120.26 (13)	C7—C15—H15A	110.5
C5—C6—H6	119.9	C14—C15—H15A	110.5
C1—C6—H6	119.9	C7—C15—H15B	110.5
C8—C7—C15	109.64 (12)	C14—C15—H15B	110.5
C8—C7—C4	125.75 (12)	H15A—C15—H15B	108.7
C15—C7—C4	124.61 (13)	O1—C16—H16A	109.5
C7—C8—C9	107.34 (12)	O1—C16—H16B	109.5
C7—C8—H8	126.3	H16A—C16—H16B	109.5
C9—C8—H8	126.3	O1—C16—H16C	109.5
C10—C9—C14	120.36 (13)	H16A—C16—H16C	109.5
C10—C9—C8	131.24 (13)	H16B—C16—H16C	109.5
C14—C9—C8	108.40 (12)
C16—O1—C1—C6	178.34 (12)	C7—C8—C9—C10	−179.34 (14)
C16—O1—C1—C2	−2.0 (2)	C7—C8—C9—C14	0.24 (15)
O1—C1—C2—C3	−178.41 (13)	C14—C9—C10—C11	−0.7 (2)
C6—C1—C2—C3	1.3 (2)	C8—C9—C10—C11	178.81 (14)
C1—C2—C3—C4	−0.1 (2)	C9—C10—C11—C12	0.6 (2)
C2—C3—C4—C5	−0.7 (2)	C10—C11—C12—C13	0.3 (2)
C2—C3—C4—C7	179.21 (13)	C11—C12—C13—C14	−0.9 (2)
C3—C4—C5—C6	0.4 (2)	C12—C13—C14—C9	0.8 (2)
C7—C4—C5—C6	−179.47 (13)	C12—C13—C14—C15	−178.47 (14)
C4—C5—C6—C1	0.7 (2)	C10—C9—C14—C13	0.0 (2)
O1—C1—C6—C5	178.17 (12)	C8—C9—C14—C13	−179.60 (12)
C2—C1—C6—C5	−1.5 (2)	C10—C9—C14—C15	179.45 (12)
C3—C4—C7—C8	−178.77 (13)	C8—C9—C14—C15	−0.18 (15)
C5—C4—C7—C8	1.1 (2)	C8—C7—C15—C14	0.09 (15)
C3—C4—C7—C15	1.7 (2)	C4—C7—C15—C14	179.70 (12)
C5—C4—C7—C15	−178.42 (13)	C13—C14—C15—C7	179.39 (14)
C15—C7—C8—C9	−0.20 (15)	C9—C14—C15—C7	0.06 (15)
C4—C7—C8—C9	−179.80 (12)

Table 1

Selected geometric parameters (Å, °)

O1—C1	1.3724 (16)
O1—C16	1.4301 (19)