4-(Benz-yloxy)benzaldehyde.

The title compound, C(14)H(12)O(2), has an essentially planar conformation with the two aromatic rings forming a dihedral angle of 5.23 (9)° and the aldehyde group lying in the plane of its aromatic group [maximum deviation = 0.204 (3) Å]. Weak inter-molecular C-H⋯O contacts are found to be shortest between the aldehyde O-atom acceptor and the H atoms of the methyl-ene group.

Related literature

For discussion of C—H⋯O contacts in a related meth­oxy derivative, see: Gerkin (1999 ▶). For other related structures, see: Allwood et al. (1985 ▶); Li & Chen (2008 ▶); Liu et al. (2006 ▶, 2007 ▶); Zhen et al. (2006 ▶). For background to the anti­retroviral treatment programme of AIDS, see: UNAIDS/WHO (2009 ▶). The established non-nucleoside reverse transcriptase inhibitors (NNRTIs) are susceptible to the development of viral resistance, emanating from mutations of amino acids in RT enzymes (Jones et al., 2006 ▶). For the need for new small mol­ecules that target HIV-1 binding sites, see: Christer et al. (1998 ▶); Himmel et al. (2006 ▶). For related literature on our work in this area, see: Hunter et al. (2007 ▶); Muhanji (2006 ▶).

Experimental

Crystal data

C14H12O2

M = 212.24

Orthorhombic,

a = 11.4772 (11) Å

b = 12.9996 (12) Å

c = 7.2032 (6) Å

V = 1074.71 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 123 K

0.42 × 0.20 × 0.14 mm

Data collection

Oxford Diffraction Gemini S diffractometer

8432 measured reflections

1579 independent reflections

1130 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.071

S = 0.91

1579 reflections

150 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027200/gw2083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027200/gw2083Isup2.hkl

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

C14H12O2	Dx = 1.312 Mg m−3
Mr = 212.24	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 2444 reflections
a = 11.4772 (11) Å	θ = 2.8–29.9°
b = 12.9996 (12) Å	µ = 0.09 mm−1
c = 7.2032 (6) Å	T = 123 K
V = 1074.71 (17) Å3	Block, colourless
Z = 4	0.42 × 0.20 × 0.14 mm
F(000) = 448

Oxford Diffraction Gemini S diffractometer	Rint = 0.049
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 3.1°
graphite	h = −15→15
ω scans	k = −18→13
8432 measured reflections	l = −9→9
1579 independent reflections	3 standard reflections every 240 min
1130 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.071	w = 1/[σ2(Fo2) + (0.0342P)2] where P = (Fo2 + 2Fc2)/3
S = 0.91	(Δ/σ)max < 0.001
1579 reflections	Δρmax = 0.18 e Å−3
150 parameters	Δρmin = −0.17 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0052 (11)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.63724 (11)	0.04432 (8)	0.81224 (19)	0.0256 (3)
O2	0.81066 (12)	−0.42284 (9)	0.8002 (2)	0.0360 (4)
C1	0.53896 (16)	0.08862 (13)	0.9065 (2)	0.0232 (4)
H1A	0.5446	0.0748	1.0413	0.028*
H1B	0.4660	0.0573	0.8599	0.028*
C2	0.53725 (17)	0.20292 (13)	0.8725 (2)	0.0212 (4)
C3	0.62873 (17)	0.25573 (12)	0.7892 (3)	0.0235 (4)
H3	0.6963	0.2195	0.7503	0.028*
C4	0.62149 (18)	0.36164 (13)	0.7626 (3)	0.0276 (5)
H4	0.6838	0.3974	0.7045	0.033*
C5	0.52362 (18)	0.41501 (14)	0.8205 (3)	0.0294 (5)
H5	0.5186	0.4872	0.8019	0.035*
C6	0.43353 (18)	0.36301 (14)	0.9054 (3)	0.0293 (5)
H6	0.3670	0.3998	0.9469	0.035*
C7	0.43932 (18)	0.25775 (14)	0.9304 (2)	0.0251 (4)
H7	0.3762	0.2225	0.9874	0.030*
C8	0.65609 (17)	−0.05854 (13)	0.8365 (3)	0.0219 (4)
C9	0.75866 (17)	−0.09649 (14)	0.7567 (2)	0.0231 (4)
H9	0.8097	−0.0512	0.6926	0.028*
C10	0.78550 (16)	−0.19922 (13)	0.7712 (3)	0.0232 (4)
H10	0.8551	−0.2250	0.7170	0.028*
C11	0.71047 (16)	−0.26592 (13)	0.8657 (2)	0.0211 (4)
C12	0.60968 (17)	−0.22681 (14)	0.9451 (2)	0.0234 (4)
H12	0.5590	−0.2720	1.0102	0.028*
C13	0.58121 (17)	−0.12411 (13)	0.9319 (2)	0.0236 (4)
H13	0.5118	−0.0985	0.9869	0.028*
C14	0.73311 (19)	−0.37705 (14)	0.8791 (3)	0.0271 (5)
H14	0.6736 (19)	−0.4158 (13)	0.961 (3)	0.033 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0262 (7)	0.0207 (6)	0.0301 (8)	0.0024 (6)	0.0083 (6)	0.0016 (6)
O2	0.0320 (9)	0.0287 (8)	0.0474 (9)	0.0057 (6)	0.0023 (8)	−0.0033 (7)
C1	0.0216 (11)	0.0224 (10)	0.0255 (11)	0.0029 (8)	0.0033 (8)	0.0005 (8)
C2	0.0210 (10)	0.0224 (10)	0.0201 (10)	−0.0017 (8)	−0.0036 (8)	−0.0005 (7)
C3	0.0202 (10)	0.0248 (10)	0.0256 (11)	0.0000 (8)	0.0003 (8)	−0.0017 (9)
C4	0.0260 (12)	0.0279 (11)	0.0288 (12)	−0.0055 (8)	0.0000 (9)	0.0008 (9)
C5	0.0339 (12)	0.0203 (10)	0.0340 (11)	0.0003 (9)	−0.0044 (10)	−0.0012 (9)
C6	0.0274 (12)	0.0288 (10)	0.0316 (12)	0.0049 (9)	−0.0009 (9)	−0.0058 (9)
C7	0.0224 (11)	0.0275 (11)	0.0254 (10)	−0.0003 (8)	0.0027 (9)	−0.0002 (8)
C8	0.0234 (10)	0.0224 (10)	0.0199 (10)	0.0006 (8)	−0.0008 (8)	−0.0002 (8)
C9	0.0211 (11)	0.0243 (10)	0.0239 (10)	−0.0043 (8)	0.0033 (8)	0.0010 (8)
C10	0.0212 (10)	0.0270 (10)	0.0213 (10)	0.0006 (8)	0.0014 (8)	−0.0027 (8)
C11	0.0222 (10)	0.0216 (10)	0.0195 (9)	−0.0009 (8)	−0.0034 (8)	0.0004 (8)
C12	0.0230 (11)	0.0254 (10)	0.0217 (10)	−0.0045 (9)	0.0012 (8)	0.0044 (8)
C13	0.0217 (11)	0.0266 (10)	0.0225 (10)	0.0014 (8)	0.0028 (8)	0.0024 (8)
C14	0.0261 (12)	0.0261 (11)	0.0290 (11)	−0.0021 (9)	−0.0046 (9)	0.0009 (9)

O1—C8	1.3657 (18)	C6—H6	0.9500
O1—C1	1.437 (2)	C7—H7	0.9500
O2—C14	1.212 (2)	C8—C13	1.392 (3)
C1—C2	1.506 (2)	C8—C9	1.400 (2)
C1—H1A	0.9900	C9—C10	1.375 (2)
C1—H1B	0.9900	C9—H9	0.9500
C2—C3	1.391 (3)	C10—C11	1.399 (2)
C2—C7	1.395 (3)	C10—H10	0.9500
C3—C4	1.393 (2)	C11—C12	1.387 (2)
C3—H3	0.9500	C11—C14	1.471 (3)
C4—C5	1.385 (3)	C12—C13	1.378 (2)
C4—H4	0.9500	C12—H12	0.9500
C5—C6	1.378 (3)	C13—H13	0.9500
C5—H5	0.9500	C14—H14	1.03 (2)
C6—C7	1.382 (3)
C8—O1—C1	117.15 (13)	C6—C7—H7	119.8
O1—C1—C2	109.20 (14)	C2—C7—H7	119.8
O1—C1—H1A	109.8	O1—C8—C13	124.39 (17)
C2—C1—H1A	109.8	O1—C8—C9	115.20 (16)
O1—C1—H1B	109.8	C13—C8—C9	120.41 (16)
C2—C1—H1B	109.8	C10—C9—C8	119.99 (16)
H1A—C1—H1B	108.3	C10—C9—H9	120.0
C3—C2—C7	119.04 (16)	C8—C9—H9	120.0
C3—C2—C1	123.18 (16)	C9—C10—C11	120.08 (17)
C7—C2—C1	117.77 (16)	C9—C10—H10	120.0
C2—C3—C4	120.15 (18)	C11—C10—H10	120.0
C2—C3—H3	119.9	C12—C11—C10	119.13 (16)
C4—C3—H3	119.9	C12—C11—C14	118.69 (16)
C5—C4—C3	120.16 (18)	C10—C11—C14	122.15 (17)
C5—C4—H4	119.9	C13—C12—C11	121.64 (16)
C3—C4—H4	119.9	C13—C12—H12	119.2
C6—C5—C4	119.76 (17)	C11—C12—H12	119.2
C6—C5—H5	120.1	C12—C13—C8	118.75 (17)
C4—C5—H5	120.1	C12—C13—H13	120.6
C5—C6—C7	120.50 (19)	C8—C13—H13	120.6
C5—C6—H6	119.7	O2—C14—C11	125.5 (2)
C7—C6—H6	119.7	O2—C14—H14	120.9 (10)
C6—C7—C2	120.38 (18)	C11—C14—H14	113.5 (10)
C8—O1—C1—C2	176.49 (14)	O1—C8—C9—C10	−179.33 (17)
O1—C1—C2—C3	−9.8 (2)	C13—C8—C9—C10	0.5 (3)
O1—C1—C2—C7	171.08 (16)	C8—C9—C10—C11	0.0 (3)
C7—C2—C3—C4	−0.7 (3)	C9—C10—C11—C12	−0.5 (3)
C1—C2—C3—C4	−179.76 (16)	C9—C10—C11—C14	177.71 (18)
C2—C3—C4—C5	0.6 (3)	C10—C11—C12—C13	0.5 (3)
C3—C4—C5—C6	0.3 (3)	C14—C11—C12—C13	−177.70 (17)
C4—C5—C6—C7	−1.0 (3)	C11—C12—C13—C8	−0.1 (3)
C5—C6—C7—C2	0.9 (3)	O1—C8—C13—C12	179.39 (17)
C3—C2—C7—C6	−0.1 (3)	C9—C8—C13—C12	−0.4 (3)
C1—C2—C7—C6	179.06 (16)	C12—C11—C14—O2	171.8 (2)
C1—O1—C8—C13	6.0 (2)	C10—C11—C14—O2	−6.3 (3)
C1—O1—C8—C9	−174.23 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2i	0.99	2.50	3.324 (2)	141
C1—H1B···O2ii	0.99	2.53	3.478 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2i	0.99	2.50	3.324 (2)	141
C1—H1B⋯O2ii	0.99	2.53	3.478 (2)	160

Symmetry codes: (i) ; (ii) .