(E)-{[But-2-ene-1,4-diylbis(-oxy)]bis-(4,1-phenyl-ene)}bis-(phenyl-methanone).

The title mol-ecule, C(30)H(24)O(4), lies about an inversion center located at the mid-point of the central C=C bond. The diphenyl-methanone unit adopts an all-trans conformation. The dihedral angle between the adjacent rings is 53.57 (4)°.

Related literature

For sterically hindered phenols and secondary aromatic amines as anti­oxidants, see: Rabek (1990 ▶); Pospisil et al. (2003 ▶); Wolf & Kaul, (1992 ▶). For synthetic phenolic anti­oxidants, such as butyl­ated hy­droxy­toluene (BHT), butyl­ated hy­droxy­anisole (BHA) or butyl­ated hy­droxy­quinone (TBHQ) as anti­oxidants, see: Omura (1995 ▶). For the ability of phenols to stop the propagation chain during the oxidation process, see: Kumar & Naik (2010 ▶); Findik et al. (2011 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For the synthesis of the title compound, see: Er et al. (2009 ▶).

Experimental

Crystal data

C30H24O4

M = 448.49

Monoclinic,

a = 24.913 (1) Å

b = 7.2586 (3) Å

c = 6.1359 (2) Å

β = 95.012 (4)°

V = 1105.33 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 123 K

0.44 × 0.37 × 0.22 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical [CrysAlis PRO (Agilent, 2012 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.976, T max = 0.989

8112 measured reflections

2409 independent reflections

1964 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.129

S = 1.09

2409 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812033624/ds2209sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033624/ds2209Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033624/ds2209Isup3.cml

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

C30H24O4	F(000) = 472
Mr = 448.49	Dx = 1.348 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3302 reflections
a = 24.913 (1) Å	θ = 3.3–28.6°
b = 7.2586 (3) Å	µ = 0.09 mm−1
c = 6.1359 (2) Å	T = 123 K
β = 95.012 (4)°	Pyrimidal, colorless
V = 1105.33 (7) Å3	0.44 × 0.37 × 0.22 mm
Z = 2

Agilent Xcalibur Ruby Gemini diffractometer	2409 independent reflections
Radiation source: fine-focus sealed tube	1964 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 10.5081 pixels mm-1	θmax = 28.6°, θmin = 3.3°
ω scans	h = −27→31
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012), based on expressions derived by Clark & Reid (1995)]	k = −9→7
Tmin = 0.976, Tmax = 0.989	l = −8→7
8112 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.5741P] where P = (Fo2 + 2Fc2)/3
2409 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Experimental. Absorption correction: analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995).

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	0.71419 (5)	0.00150 (18)	0.81909 (19)	0.0279 (3)
O2	0.92164 (4)	−0.01342 (16)	0.31446 (19)	0.0240 (3)
C1	0.65514 (7)	−0.0714 (2)	0.2731 (3)	0.0214 (4)
H1A	0.6853	−0.1202	0.2080	0.026*
C2	0.60418 (7)	−0.0791 (2)	0.1610 (3)	0.0243 (4)
H2A	0.5994	−0.1345	0.0203	0.029*
C3	0.56033 (7)	−0.0055 (2)	0.2551 (3)	0.0264 (4)
H3A	0.5254	−0.0123	0.1796	0.032*
C4	0.56713 (7)	0.0778 (2)	0.4592 (3)	0.0255 (4)
H4A	0.5371	0.1313	0.5209	0.031*
C5	0.61760 (6)	0.0832 (2)	0.5730 (3)	0.0222 (4)
H5A	0.6221	0.1381	0.7139	0.027*
C6	0.66211 (6)	0.0077 (2)	0.4805 (3)	0.0193 (4)
C7	0.71442 (6)	0.0017 (2)	0.6198 (3)	0.0196 (4)
C8	0.76709 (6)	−0.0056 (2)	0.5208 (3)	0.0189 (4)
C9	0.81067 (6)	−0.0885 (2)	0.6439 (3)	0.0203 (4)
H9A	0.8053	−0.1436	0.7808	0.024*
C10	0.86106 (6)	−0.0910 (2)	0.5686 (3)	0.0207 (4)
H10A	0.8900	−0.1516	0.6505	0.025*
C11	0.86966 (6)	−0.0043 (2)	0.3717 (3)	0.0195 (4)
C12	0.82714 (6)	0.0799 (2)	0.2468 (3)	0.0207 (4)
H12A	0.8330	0.1391	0.1128	0.025*
C13	0.77587 (6)	0.0758 (2)	0.3220 (3)	0.0195 (4)
H13A	0.7465	0.1297	0.2357	0.023*
C14	0.93354 (7)	0.0764 (3)	0.1161 (3)	0.0251 (4)
H14A	0.9271	0.2106	0.1262	0.030*
H14B	0.9103	0.0271	−0.0097	0.030*
C15	0.99148 (7)	0.0394 (3)	0.0874 (3)	0.0265 (4)
H15A	1.0176	0.0748	0.2019	0.032*

	U11	U22	U33	U12	U13	U23
O1	0.0252 (7)	0.0416 (8)	0.0173 (6)	−0.0015 (5)	0.0036 (5)	−0.0004 (5)
O2	0.0154 (6)	0.0328 (7)	0.0242 (6)	0.0014 (5)	0.0045 (5)	0.0017 (5)
C1	0.0218 (8)	0.0217 (8)	0.0215 (8)	−0.0006 (6)	0.0055 (7)	0.0005 (7)
C2	0.0264 (9)	0.0263 (9)	0.0201 (8)	−0.0031 (7)	0.0013 (7)	0.0000 (7)
C3	0.0207 (8)	0.0305 (10)	0.0276 (9)	−0.0018 (7)	−0.0002 (7)	0.0048 (7)
C4	0.0185 (8)	0.0290 (9)	0.0301 (9)	−0.0005 (7)	0.0076 (7)	0.0020 (7)
C5	0.0214 (8)	0.0248 (9)	0.0211 (8)	−0.0021 (7)	0.0064 (7)	−0.0010 (7)
C6	0.0179 (8)	0.0207 (8)	0.0198 (8)	−0.0017 (6)	0.0050 (6)	0.0019 (6)
C7	0.0199 (8)	0.0198 (8)	0.0195 (8)	−0.0017 (6)	0.0036 (6)	−0.0007 (6)
C8	0.0191 (8)	0.0188 (8)	0.0191 (8)	−0.0011 (6)	0.0024 (6)	−0.0023 (6)
C9	0.0231 (8)	0.0216 (8)	0.0162 (8)	−0.0024 (6)	0.0009 (6)	−0.0003 (6)
C10	0.0199 (8)	0.0215 (9)	0.0201 (8)	0.0004 (6)	−0.0021 (6)	−0.0008 (6)
C11	0.0167 (8)	0.0212 (8)	0.0208 (8)	−0.0015 (6)	0.0025 (6)	−0.0053 (6)
C12	0.0205 (8)	0.0220 (8)	0.0199 (8)	−0.0008 (6)	0.0045 (6)	0.0013 (6)
C13	0.0187 (8)	0.0212 (8)	0.0185 (8)	0.0013 (6)	0.0012 (6)	−0.0001 (6)
C14	0.0204 (8)	0.0331 (10)	0.0225 (9)	0.0002 (7)	0.0058 (7)	0.0010 (7)
C15	0.0174 (8)	0.0357 (10)	0.0267 (9)	−0.0029 (7)	0.0039 (7)	−0.0015 (7)

O1—C7	1.223 (2)	C8—C13	1.390 (2)
O2—C11	1.3726 (19)	C8—C9	1.403 (2)
O2—C14	1.435 (2)	C9—C10	1.376 (2)
C1—C2	1.391 (2)	C9—H9A	0.9500
C1—C6	1.393 (2)	C10—C11	1.395 (2)
C1—H1A	0.9500	C10—H10A	0.9500
C2—C3	1.387 (3)	C11—C12	1.393 (2)
C2—H2A	0.9500	C12—C13	1.395 (2)
C3—C4	1.388 (3)	C12—H12A	0.9500
C3—H3A	0.9500	C13—H13A	0.9500
C4—C5	1.384 (2)	C14—C15	1.494 (2)
C4—H4A	0.9500	C14—H14A	0.9900
C5—C6	1.401 (2)	C14—H14B	0.9900
C5—H5A	0.9500	C15—C15i	1.318 (4)
C6—C7	1.496 (2)	C15—H15A	0.9500
C7—C8	1.494 (2)
C11—O2—C14	117.70 (12)	C10—C9—C8	120.69 (15)
C2—C1—C6	120.26 (16)	C10—C9—H9A	119.7
C2—C1—H1A	119.9	C8—C9—H9A	119.7
C6—C1—H1A	119.9	C9—C10—C11	119.94 (14)
C3—C2—C1	119.77 (16)	C9—C10—H10A	120.0
C3—C2—H2A	120.1	C11—C10—H10A	120.0
C1—C2—H2A	120.1	O2—C11—C12	124.69 (15)
C2—C3—C4	120.35 (16)	O2—C11—C10	114.82 (14)
C2—C3—H3A	119.8	C12—C11—C10	120.48 (15)
C4—C3—H3A	119.8	C11—C12—C13	118.87 (15)
C5—C4—C3	120.08 (16)	C11—C12—H12A	120.6
C5—C4—H4A	120.0	C13—C12—H12A	120.6
C3—C4—H4A	120.0	C8—C13—C12	121.18 (15)
C4—C5—C6	120.06 (16)	C8—C13—H13A	119.4
C4—C5—H5A	120.0	C12—C13—H13A	119.4
C6—C5—H5A	120.0	O2—C14—C15	106.96 (13)
C1—C6—C5	119.44 (15)	O2—C14—H14A	110.3
C1—C6—C7	122.90 (15)	C15—C14—H14A	110.3
C5—C6—C7	117.43 (15)	O2—C14—H14B	110.3
O1—C7—C8	119.17 (14)	C15—C14—H14B	110.3
O1—C7—C6	119.44 (15)	H14A—C14—H14B	108.6
C8—C7—C6	121.38 (14)	C15i—C15—C14	123.9 (2)
C13—C8—C9	118.77 (15)	C15i—C15—H15A	118.1
C13—C8—C7	123.58 (14)	C14—C15—H15A	118.1
C9—C8—C7	117.50 (14)
C6—C1—C2—C3	0.8 (3)	C6—C7—C8—C9	−152.96 (15)
C1—C2—C3—C4	0.9 (3)	C13—C8—C9—C10	−0.7 (2)
C2—C3—C4—C5	−1.9 (3)	C7—C8—C9—C10	−176.32 (15)
C3—C4—C5—C6	1.3 (3)	C8—C9—C10—C11	2.4 (2)
C2—C1—C6—C5	−1.5 (2)	C14—O2—C11—C12	2.6 (2)
C2—C1—C6—C7	173.00 (15)	C14—O2—C11—C10	−178.67 (14)
C4—C5—C6—C1	0.4 (2)	C9—C10—C11—O2	179.11 (14)
C4—C5—C6—C7	−174.34 (15)	C9—C10—C11—C12	−2.1 (2)
C1—C6—C7—O1	−150.21 (16)	O2—C11—C12—C13	178.62 (15)
C5—C6—C7—O1	24.4 (2)	C10—C11—C12—C13	−0.1 (2)
C1—C6—C7—C8	29.3 (2)	C9—C8—C13—C12	−1.5 (2)
C5—C6—C7—C8	−156.15 (15)	C7—C8—C13—C12	173.86 (15)
O1—C7—C8—C13	−148.92 (17)	C11—C12—C13—C8	1.9 (2)
C6—C7—C8—C13	31.6 (2)	C11—O2—C14—C15	−177.68 (14)
O1—C7—C8—C9	26.5 (2)	O2—C14—C15—C15i	123.3 (2)