3,4-Dimeth-oxy-4'-methyl-biphen-yl.

In the title compound, C15H16O2, the dihedral angle between the planes of the aromatic rings is 30.5 (2)°. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds and C-H⋯π inter-actions, forming a two-dimensional network lying parallel to (100).

Related literature

For structural studies of related biphenyl derivatives, see Lahtinen et al. (2013a ▶,b ▶,c ▶); Li et al. (2012a ▶,b ▶). For details of the synthesis, see: Percec et al. (2004 ▶, 2006 ▶); Wolfe et al. (1999 ▶). For details of various cross-coupling reactions, see: Corbet & Mignani (2006 ▶); Miyaura et al. (1981 ▶); Miyaura & Suzuki (1995 ▶); Percec et al. (2004 ▶); Wolfe et al. (1999 ▶). For self-assembling supra­molecular dendrons based on 3,4-branched bi­phenyls, see: Percec et al. (2006 ▶, 2007 ▶). For hollow supra­molecular dendrimers, see Peterca et al. (2006 ▶); Percec et al. (2008 ▶). For dendritic polyaryl esters, see Nummelin et al. (2000 ▶).

Experimental

Crystal data

C15H16O2

M = 228.28

Monoclinic,

a = 17.7430 (9) Å

b = 8.7581 (3) Å

c = 8.1135 (3) Å

β = 101.795 (5)°

V = 1234.17 (9) Å3

Z = 4

Cu Kα radiation

μ = 0.64 mm−1

T = 123 K

0.36 × 0.26 × 0.04 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

Absorption correction: analytical (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.880, T max = 0.977

4273 measured reflections

2282 independent reflections

1844 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.143

S = 1.07

2282 reflections

157 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: OLEX2.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813008957/fj2625sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008957/fj2625Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008957/fj2625Isup3.cml

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

C15H16O2	F(000) = 488
Mr = 228.28	Dx = 1.229 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
a = 17.7430 (9) Å	Cell parameters from 1622 reflections
b = 8.7581 (3) Å	θ = 5.1–76.7°
c = 8.1135 (3) Å	µ = 0.64 mm−1
β = 101.795 (5)°	T = 123 K
V = 1234.17 (9) Å3	Plate, colourless
Z = 4	0.36 × 0.26 × 0.04 mm

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	2282 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1844 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
Detector resolution: 10.3953 pixels mm-1	θmax = 69.0°, θmin = 5.1°
ω scans	h = −18→21
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)	k = −10→7
Tmin = 0.880, Tmax = 0.977	l = −9→9
4273 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0735P)2 + 0.0799P] where P = (Fo2 + 2Fc2)/3
2282 reflections	(Δ/σ)max < 0.001
157 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.31 e Å−3
0 constraints

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
O16	0.89457 (7)	0.46978 (13)	0.00350 (15)	0.0335 (3)
O14	0.94276 (7)	0.60539 (14)	0.28726 (15)	0.0353 (3)
C9	0.82177 (9)	0.56204 (18)	0.37788 (19)	0.0282 (3)
H9	0.8400	0.6111	0.4829	0.034*
C11	0.84258 (10)	0.47747 (17)	0.10680 (19)	0.0283 (4)
C10	0.86951 (10)	0.55131 (17)	0.2626 (2)	0.0284 (3)
C8	0.74672 (9)	0.50130 (17)	0.34160 (19)	0.0278 (3)
C12	0.76904 (10)	0.41966 (19)	0.0695 (2)	0.0317 (4)
H12	0.7506	0.3713	−0.0358	0.038*
C13	0.72128 (10)	0.43187 (19)	0.1867 (2)	0.0310 (4)
H13	0.6705	0.3918	0.1594	0.037*
C4	0.70104 (10)	0.63163 (19)	0.58078 (19)	0.0312 (4)
H4	0.7379	0.7101	0.5799	0.037*
C3	0.65286 (10)	0.6385 (2)	0.6963 (2)	0.0344 (4)
H3	0.6577	0.7212	0.7734	0.041*
C6	0.64005 (10)	0.39913 (18)	0.4706 (2)	0.0317 (4)
H6	0.6349	0.3161	0.3937	0.038*
C7	0.59199 (10)	0.40748 (19)	0.5854 (2)	0.0340 (4)
H7	0.5543	0.3303	0.5851	0.041*
C5	0.69597 (9)	0.51097 (18)	0.46610 (19)	0.0281 (4)
C2	0.59771 (10)	0.5262 (2)	0.7009 (2)	0.0331 (4)
C1	0.54666 (11)	0.5331 (2)	0.8280 (2)	0.0418 (4)
H1A	0.5696	0.6014	0.9203	0.063*
H1B	0.5413	0.4305	0.8726	0.063*
H1C	0.4958	0.5717	0.7737	0.063*
C17	0.86955 (12)	0.3987 (2)	−0.1569 (2)	0.0401 (4)
H17A	0.8250	0.4540	−0.2208	0.060*
H17B	0.8551	0.2926	−0.1409	0.060*
H17C	0.9114	0.4009	−0.2191	0.060*
C15	0.97056 (11)	0.6901 (2)	0.4385 (2)	0.0429 (5)
H15A	1.0228	0.7267	0.4391	0.064*
H15B	0.9713	0.6241	0.5363	0.064*
H15C	0.9366	0.7775	0.4435	0.064*

	U11	U22	U33	U12	U13	U23
O16	0.0440 (7)	0.0297 (6)	0.0324 (6)	−0.0001 (5)	0.0209 (5)	−0.0024 (4)
O14	0.0392 (7)	0.0340 (6)	0.0368 (6)	−0.0065 (5)	0.0173 (5)	−0.0074 (5)
C9	0.0380 (8)	0.0238 (7)	0.0255 (7)	0.0008 (6)	0.0128 (6)	0.0006 (5)
C11	0.0389 (8)	0.0230 (7)	0.0268 (7)	0.0044 (6)	0.0159 (6)	0.0036 (5)
C10	0.0362 (8)	0.0208 (7)	0.0307 (8)	0.0001 (6)	0.0129 (6)	0.0023 (6)
C8	0.0351 (8)	0.0235 (7)	0.0273 (7)	0.0017 (6)	0.0122 (6)	0.0024 (6)
C12	0.0406 (9)	0.0304 (8)	0.0256 (7)	0.0018 (6)	0.0101 (6)	−0.0017 (6)
C13	0.0351 (8)	0.0311 (8)	0.0285 (8)	−0.0003 (6)	0.0108 (6)	−0.0009 (6)
C4	0.0396 (9)	0.0286 (8)	0.0278 (7)	−0.0017 (6)	0.0124 (6)	−0.0003 (6)
C3	0.0448 (10)	0.0336 (9)	0.0278 (8)	0.0034 (7)	0.0146 (7)	−0.0020 (6)
C6	0.0391 (9)	0.0266 (8)	0.0318 (8)	0.0004 (6)	0.0131 (6)	−0.0003 (6)
C7	0.0360 (9)	0.0315 (8)	0.0382 (9)	0.0005 (6)	0.0166 (7)	0.0048 (6)
C5	0.0344 (8)	0.0263 (8)	0.0252 (7)	0.0030 (6)	0.0101 (6)	0.0036 (6)
C2	0.0365 (8)	0.0370 (9)	0.0285 (8)	0.0065 (7)	0.0130 (6)	0.0059 (6)
C1	0.0417 (10)	0.0537 (11)	0.0347 (9)	0.0078 (8)	0.0186 (7)	0.0044 (8)
C17	0.0522 (11)	0.0454 (10)	0.0264 (8)	0.0081 (8)	0.0165 (7)	−0.0011 (7)
C15	0.0435 (10)	0.0394 (9)	0.0497 (10)	−0.0106 (7)	0.0188 (8)	−0.0172 (8)

O16—C11	1.3689 (19)	C3—H3	0.9500
O16—C17	1.429 (2)	C3—C2	1.393 (3)
O14—C10	1.359 (2)	C6—H6	0.9500
O14—C15	1.432 (2)	C6—C7	1.388 (2)
C9—H9	0.9500	C6—C5	1.400 (2)
C9—C10	1.388 (2)	C7—H7	0.9500
C9—C8	1.408 (2)	C7—C2	1.389 (3)
C11—C10	1.413 (2)	C2—C1	1.507 (2)
C11—C12	1.375 (3)	C1—H1A	0.9800
C8—C13	1.386 (2)	C1—H1B	0.9800
C8—C5	1.487 (2)	C1—H1C	0.9800
C12—H12	0.9500	C17—H17A	0.9800
C12—C13	1.401 (2)	C17—H17B	0.9800
C13—H13	0.9500	C17—H17C	0.9800
C4—H4	0.9500	C15—H15A	0.9800
C4—C3	1.393 (2)	C15—H15B	0.9800
C4—C5	1.399 (2)	C15—H15C	0.9800
C11—O16—C17	117.15 (14)	C5—C6—H6	119.5
C10—O14—C15	117.27 (13)	C6—C7—H7	119.3
C10—C9—H9	119.5	C6—C7—C2	121.46 (16)
C10—C9—C8	121.00 (15)	C2—C7—H7	119.3
C8—C9—H9	119.5	C4—C5—C8	121.97 (15)
O16—C11—C10	115.04 (14)	C4—C5—C6	117.45 (15)
O16—C11—C12	125.13 (15)	C6—C5—C8	120.57 (14)
C12—C11—C10	119.83 (14)	C3—C2—C1	120.94 (16)
O14—C10—C9	125.05 (15)	C7—C2—C3	117.72 (15)
O14—C10—C11	115.43 (14)	C7—C2—C1	121.33 (17)
C9—C10—C11	119.51 (15)	C2—C1—H1A	109.5
C9—C8—C5	120.98 (14)	C2—C1—H1B	109.5
C13—C8—C9	118.30 (14)	C2—C1—H1C	109.5
C13—C8—C5	120.72 (15)	H1A—C1—H1B	109.5
C11—C12—H12	120.0	H1A—C1—H1C	109.5
C11—C12—C13	120.10 (15)	H1B—C1—H1C	109.5
C13—C12—H12	120.0	O16—C17—H17A	109.5
C8—C13—C12	121.24 (15)	O16—C17—H17B	109.5
C8—C13—H13	119.4	O16—C17—H17C	109.5
C12—C13—H13	119.4	H17A—C17—H17B	109.5
C3—C4—H4	119.5	H17A—C17—H17C	109.5
C3—C4—C5	121.00 (16)	H17B—C17—H17C	109.5
C5—C4—H4	119.5	O14—C15—H15A	109.5
C4—C3—H3	119.4	O14—C15—H15B	109.5
C4—C3—C2	121.26 (15)	O14—C15—H15C	109.5
C2—C3—H3	119.4	H15A—C15—H15B	109.5
C7—C6—H6	119.5	H15A—C15—H15C	109.5
C7—C6—C5	121.10 (15)	H15B—C15—H15C	109.5
O16—C11—C10—O14	0.6 (2)	C4—C3—C2—C7	−0.4 (3)
O16—C11—C10—C9	−178.57 (13)	C4—C3—C2—C1	179.02 (16)
O16—C11—C12—C13	178.85 (14)	C3—C4—C5—C8	179.95 (14)
C9—C8—C13—C12	1.1 (2)	C3—C4—C5—C6	0.9 (2)
C9—C8—C5—C4	30.5 (2)	C6—C7—C2—C3	0.8 (3)
C9—C8—C5—C6	−150.44 (16)	C6—C7—C2—C1	−178.60 (16)
C11—C12—C13—C8	−0.2 (2)	C7—C6—C5—C8	−179.55 (15)
C10—C9—C8—C13	−0.7 (2)	C7—C6—C5—C4	−0.5 (2)
C10—C9—C8—C5	179.17 (14)	C5—C8—C13—C12	−178.85 (15)
C10—C11—C12—C13	−0.9 (2)	C5—C4—C3—C2	−0.4 (3)
C8—C9—C10—O14	−179.46 (15)	C5—C6—C7—C2	−0.4 (3)
C8—C9—C10—C11	−0.4 (2)	C17—O16—C11—C10	−178.82 (14)
C12—C11—C10—O14	−179.61 (14)	C17—O16—C11—C12	1.4 (2)
C12—C11—C10—C9	1.2 (2)	C15—O14—C10—C9	−5.0 (2)
C13—C8—C5—C4	−149.58 (16)	C15—O14—C10—C11	175.86 (15)
C13—C8—C5—C6	29.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O16i	0.98	2.57	3.389 (2)	141
C15—H15C···O16ii	0.98	2.42	3.356 (2)	160
C4—H4···Cg2ii	0.95	2.96	3.7807 (18)	145
C17—H17B···Cg2iii	0.98	2.83	3.7119 (19)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O16i	0.98	2.57	3.389 (2)	141
C15—H15C⋯O16ii	0.98	2.42	3.356 (2)	160
C4—H4⋯Cg2ii	0.95	2.96	3.7807 (18)	145
C17—H17B⋯Cg2iii	0.98	2.83	3.7119 (19)	150

Symmetry codes: (i) ; (ii) ; (iii) .