1-[2-(Trit-yloxy)phen-yl]ethanone.

In the title compound, C27H22O2, the acetyl group is nearly coplanar with the the ring to which it attacted [O-C-C-C torsion angle = -5.5 (3)°]. The three phenyl groups of the tri-phenyl-methyl substituent are mutually nearly perpendicular, making dihedral angles of 89.87 (11) and 78.29 (11) and 60.34 (11)°. Two intra-molecular C-H⋯ O hydrogen bonds occur. In the crystal, C-H⋯ O hydrogen bonds link the moleclues into chains along the b-axis direction.

Related literature

For general background to tri­phenyl­methyl, see: Casanova et al. (2006 ▶); Aldaye & Sleiman (2007 ▶).

Experimental

Crystal data

C27H22O2

M = 378.45

Orthorhombic,

a = 15.6996 (17) Å

b = 8.8767 (9) Å

c = 29.591 (3) Å

V = 4123.8 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.26 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1996 ▶) T min = 0.674, T max = 0.745

21669 measured reflections

3653 independent reflections

2496 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.128

S = 1.02

3653 reflections

263 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813012956/ds2228sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012956/ds2228Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012956/ds2228Isup3.cml

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

C27H22O2	F(000) = 1600
Mr = 378.45	Dx = 1.219 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3063 reflections
a = 15.6996 (17) Å	θ = 2.6–21.8°
b = 8.8767 (9) Å	µ = 0.08 mm−1
c = 29.591 (3) Å	T = 296 K
V = 4123.8 (7) Å3	Block, colourless
Z = 8	0.26 × 0.24 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	3653 independent reflections
Radiation source: fine-focus sealed tube	2496 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
phi and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 1996)	h = −18→15
Tmin = 0.674, Tmax = 0.745	k = −10→10
21669 measured reflections	l = −35→28

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0619P)2 + 0.751P] where P = (Fo2 + 2Fc2)/3
3653 reflections	(Δ/σ)max = 0.001
263 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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	0.83938 (14)	0.9201 (2)	0.78288 (6)	0.0885 (6)
O2	0.97143 (9)	0.99213 (14)	0.66452 (4)	0.0430 (4)
C1	0.93023 (12)	1.1103 (2)	0.68509 (6)	0.0418 (5)
C2	0.93469 (14)	1.2572 (2)	0.66877 (7)	0.0518 (6)
H2	0.9646	1.2774	0.6423	0.062*
C3	0.89509 (16)	1.3726 (3)	0.69158 (8)	0.0652 (7)
H3	0.8979	1.4703	0.6803	0.078*
C4	0.85108 (17)	1.3441 (3)	0.73112 (9)	0.0724 (8)
H4	0.8248	1.4222	0.7467	0.087*
C5	0.84667 (15)	1.1997 (3)	0.74704 (8)	0.0626 (7)
H5	0.8164	1.1812	0.7735	0.075*
C6	0.88591 (13)	1.0789 (2)	0.72507 (6)	0.0456 (5)
C7	0.87505 (15)	0.9273 (3)	0.74669 (7)	0.0537 (6)
C8	0.9036 (2)	0.7862 (3)	0.72541 (9)	0.0893 (10)
H8A	0.8850	0.7021	0.7432	0.134*
H8B	0.9647	0.7857	0.7235	0.134*
H8C	0.8799	0.7788	0.6956	0.134*
C9	0.98726 (12)	0.9888 (2)	0.61572 (6)	0.0372 (5)
C16	1.07153 (12)	1.0672 (2)	0.60443 (6)	0.0371 (4)
C21	1.11903 (13)	1.1444 (2)	0.63622 (7)	0.0488 (5)
H21	1.0994	1.1511	0.6658	0.059*
C20	1.19551 (14)	1.2119 (3)	0.62452 (8)	0.0605 (6)
H20	1.2261	1.2654	0.6461	0.073*
C19	1.22651 (15)	1.2004 (3)	0.58119 (8)	0.0604 (6)
H19	1.2777	1.2462	0.5734	0.073*
C18	1.18105 (15)	1.1206 (3)	0.54957 (8)	0.0556 (6)
H18	1.2020	1.1112	0.5203	0.067*
C17	1.10481 (13)	1.0543 (2)	0.56092 (7)	0.0462 (5)
H17	1.0749	1.0001	0.5392	0.055*
C22	0.90861 (12)	1.0482 (2)	0.59090 (6)	0.0396 (5)
C23	0.91211 (14)	1.1540 (2)	0.55649 (7)	0.0481 (5)
H23	0.9644	1.1939	0.5478	0.058*
C24	0.83844 (16)	1.2008 (3)	0.53496 (8)	0.0608 (6)
H24	0.8417	1.2712	0.5118	0.073*
C25	0.76079 (16)	1.1442 (3)	0.54752 (8)	0.0662 (7)
H25	0.7116	1.1761	0.5329	0.079*
C26	0.75589 (15)	1.0406 (3)	0.58172 (8)	0.0605 (6)
H26	0.7032	1.0027	0.5906	0.073*
C27	0.82935 (14)	0.9922 (2)	0.60313 (7)	0.0514 (5)
H27	0.8255	0.9209	0.6261	0.062*
C10	1.00059 (12)	0.8202 (2)	0.60568 (6)	0.0373 (5)
C11	0.96804 (14)	0.7533 (2)	0.56714 (7)	0.0488 (5)
H11	0.9331	0.8082	0.5479	0.059*
C12	0.98735 (15)	0.6048 (2)	0.55720 (8)	0.0612 (6)
H12	0.9649	0.5604	0.5313	0.073*
C13	1.03894 (16)	0.5228 (2)	0.58499 (8)	0.0610 (6)
H13	1.0520	0.4234	0.5779	0.073*
C14	1.07137 (16)	0.5871 (2)	0.62336 (8)	0.0586 (6)
H14	1.1060	0.5311	0.6425	0.070*
C15	1.05261 (14)	0.7353 (2)	0.63351 (7)	0.0487 (5)
H15	1.0753	0.7786	0.6595	0.058*

	U11	U22	U33	U12	U13	U23
O1	0.1163 (16)	0.1011 (14)	0.0480 (10)	−0.0199 (12)	0.0248 (10)	0.0035 (9)
O2	0.0546 (9)	0.0418 (7)	0.0326 (7)	0.0061 (7)	0.0067 (6)	−0.0006 (6)
C1	0.0427 (11)	0.0451 (12)	0.0376 (11)	0.0000 (9)	0.0046 (9)	−0.0088 (9)
C2	0.0614 (15)	0.0440 (12)	0.0498 (13)	−0.0001 (11)	0.0126 (11)	−0.0050 (10)
C3	0.0753 (17)	0.0466 (13)	0.0737 (17)	0.0049 (12)	0.0114 (14)	−0.0114 (12)
C4	0.0726 (18)	0.0660 (18)	0.0786 (18)	0.0063 (14)	0.0219 (14)	−0.0260 (14)
C5	0.0603 (15)	0.0739 (17)	0.0536 (14)	−0.0059 (13)	0.0174 (12)	−0.0186 (13)
C6	0.0415 (12)	0.0563 (13)	0.0389 (11)	−0.0042 (10)	0.0022 (9)	−0.0078 (10)
C7	0.0524 (13)	0.0711 (15)	0.0378 (12)	−0.0140 (12)	0.0019 (10)	0.0015 (11)
C8	0.132 (3)	0.0568 (16)	0.0792 (19)	0.0034 (17)	0.0404 (18)	0.0150 (14)
C9	0.0459 (12)	0.0379 (10)	0.0278 (10)	0.0026 (9)	0.0039 (8)	0.0004 (8)
C16	0.0413 (11)	0.0351 (10)	0.0348 (10)	0.0042 (9)	0.0012 (9)	0.0005 (8)
C21	0.0468 (12)	0.0596 (13)	0.0400 (11)	0.0002 (10)	−0.0012 (10)	−0.0072 (10)
C20	0.0467 (14)	0.0689 (16)	0.0659 (16)	−0.0072 (11)	−0.0061 (12)	−0.0107 (12)
C19	0.0463 (13)	0.0641 (15)	0.0709 (17)	−0.0071 (11)	0.0085 (12)	0.0025 (13)
C18	0.0578 (14)	0.0603 (14)	0.0488 (13)	−0.0042 (12)	0.0143 (11)	0.0048 (11)
C17	0.0541 (13)	0.0460 (12)	0.0386 (11)	−0.0025 (10)	0.0040 (10)	−0.0021 (9)
C22	0.0447 (12)	0.0359 (10)	0.0381 (11)	0.0047 (9)	0.0006 (9)	−0.0042 (8)
C23	0.0542 (13)	0.0427 (12)	0.0474 (12)	0.0051 (10)	−0.0029 (10)	0.0002 (10)
C24	0.0679 (17)	0.0546 (14)	0.0599 (15)	0.0125 (12)	−0.0114 (12)	0.0077 (11)
C25	0.0555 (15)	0.0696 (16)	0.0734 (17)	0.0196 (13)	−0.0160 (13)	−0.0010 (14)
C26	0.0426 (13)	0.0661 (16)	0.0730 (16)	0.0032 (11)	−0.0019 (12)	−0.0067 (13)
C27	0.0497 (13)	0.0503 (12)	0.0543 (13)	0.0022 (10)	0.0039 (11)	0.0006 (10)
C10	0.0396 (11)	0.0353 (10)	0.0369 (11)	0.0006 (9)	0.0058 (9)	0.0003 (8)
C11	0.0516 (13)	0.0473 (12)	0.0475 (12)	0.0041 (10)	−0.0032 (10)	−0.0068 (10)
C12	0.0666 (16)	0.0508 (13)	0.0662 (15)	−0.0003 (12)	0.0013 (12)	−0.0208 (12)
C13	0.0672 (16)	0.0377 (12)	0.0781 (17)	0.0027 (11)	0.0141 (13)	−0.0065 (12)
C14	0.0682 (16)	0.0435 (13)	0.0642 (15)	0.0125 (11)	0.0062 (12)	0.0096 (11)
C15	0.0546 (13)	0.0480 (12)	0.0436 (12)	0.0054 (10)	0.0005 (10)	0.0018 (10)

O1—C7	1.210 (2)	C19—C18	1.374 (3)
O2—C1	1.374 (2)	C19—H19	0.9300
O2—C9	1.466 (2)	C18—C17	1.375 (3)
C1—C2	1.393 (3)	C18—H18	0.9300
C1—C6	1.401 (3)	C17—H17	0.9300
C2—C3	1.375 (3)	C22—C23	1.386 (3)
C2—H2	0.9300	C22—C27	1.388 (3)
C3—C4	1.382 (3)	C23—C24	1.384 (3)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.367 (3)	C24—C25	1.370 (3)
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.397 (3)	C25—C26	1.370 (3)
C5—H5	0.9300	C25—H25	0.9300
C6—C7	1.500 (3)	C26—C27	1.384 (3)
C7—C8	1.472 (3)	C26—H26	0.9300
C8—H8A	0.9600	C27—H27	0.9300
C8—H8B	0.9600	C10—C15	1.383 (3)
C8—H8C	0.9600	C10—C11	1.384 (3)
C9—C22	1.530 (3)	C11—C12	1.384 (3)
C9—C16	1.532 (3)	C11—H11	0.9300
C9—C10	1.540 (3)	C12—C13	1.364 (3)
C16—C21	1.382 (3)	C12—H12	0.9300
C16—C17	1.394 (3)	C13—C14	1.369 (3)
C21—C20	1.386 (3)	C13—H13	0.9300
C21—H21	0.9300	C14—C15	1.381 (3)
C20—C19	1.375 (3)	C14—H14	0.9300
C20—H20	0.9300	C15—H15	0.9300
C1—O2—C9	122.10 (14)	C18—C19—H19	120.4
O2—C1—C2	122.52 (17)	C20—C19—H19	120.4
O2—C1—C6	117.15 (17)	C19—C18—C17	120.4 (2)
C2—C1—C6	120.27 (18)	C19—C18—H18	119.8
C3—C2—C1	120.3 (2)	C17—C18—H18	119.8
C3—C2—H2	119.8	C18—C17—C16	121.1 (2)
C1—C2—H2	119.8	C18—C17—H17	119.4
C2—C3—C4	120.3 (2)	C16—C17—H17	119.4
C2—C3—H3	119.8	C23—C22—C27	118.02 (19)
C4—C3—H3	119.8	C23—C22—C9	123.64 (18)
C5—C4—C3	119.3 (2)	C27—C22—C9	118.34 (17)
C5—C4—H4	120.4	C24—C23—C22	120.5 (2)
C3—C4—H4	120.4	C24—C23—H23	119.7
C4—C5—C6	122.4 (2)	C22—C23—H23	119.7
C4—C5—H5	118.8	C25—C24—C23	120.6 (2)
C6—C5—H5	118.8	C25—C24—H24	119.7
C5—C6—C1	117.4 (2)	C23—C24—H24	119.7
C5—C6—C7	116.10 (19)	C24—C25—C26	119.8 (2)
C1—C6—C7	126.52 (19)	C24—C25—H25	120.1
O1—C7—C8	118.4 (2)	C26—C25—H25	120.1
O1—C7—C6	118.5 (2)	C25—C26—C27	120.0 (2)
C8—C7—C6	123.11 (19)	C25—C26—H26	120.0
C7—C8—H8A	109.5	C27—C26—H26	120.0
C7—C8—H8B	109.5	C26—C27—C22	121.1 (2)
H8A—C8—H8B	109.5	C26—C27—H27	119.5
C7—C8—H8C	109.5	C22—C27—H27	119.5
H8A—C8—H8C	109.5	C15—C10—C11	118.31 (18)
H8B—C8—H8C	109.5	C15—C10—C9	119.69 (17)
O2—C9—C22	109.22 (15)	C11—C10—C9	121.75 (17)
O2—C9—C16	110.62 (15)	C10—C11—C12	120.2 (2)
C22—C9—C16	115.84 (15)	C10—C11—H11	119.9
O2—C9—C10	103.44 (14)	C12—C11—H11	119.9
C22—C9—C10	110.60 (15)	C13—C12—C11	120.6 (2)
C16—C9—C10	106.39 (14)	C13—C12—H12	119.7
C21—C16—C17	117.84 (19)	C11—C12—H12	119.7
C21—C16—C9	122.88 (17)	C12—C13—C14	119.9 (2)
C17—C16—C9	119.20 (17)	C12—C13—H13	120.1
C16—C21—C20	120.78 (19)	C14—C13—H13	120.1
C16—C21—H21	119.6	C13—C14—C15	119.9 (2)
C20—C21—H21	119.6	C13—C14—H14	120.1
C19—C20—C21	120.5 (2)	C15—C14—H14	120.1
C19—C20—H20	119.7	C14—C15—C10	121.0 (2)
C21—C20—H20	119.7	C14—C15—H15	119.5
C18—C19—C20	119.3 (2)	C10—C15—H15	119.5
C9—O2—C1—C2	−30.2 (3)	C19—C18—C17—C16	0.4 (3)
C9—O2—C1—C6	152.75 (17)	C21—C16—C17—C18	−2.1 (3)
O2—C1—C2—C3	−177.4 (2)	C9—C16—C17—C18	−178.78 (18)
C6—C1—C2—C3	−0.5 (3)	O2—C9—C22—C23	132.84 (18)
C1—C2—C3—C4	0.5 (4)	C16—C9—C22—C23	7.2 (3)
C2—C3—C4—C5	−0.6 (4)	C10—C9—C22—C23	−114.0 (2)
C3—C4—C5—C6	0.7 (4)	O2—C9—C22—C27	−47.8 (2)
C4—C5—C6—C1	−0.6 (4)	C16—C9—C22—C27	−173.50 (17)
C4—C5—C6—C7	−179.9 (2)	C10—C9—C22—C27	65.4 (2)
O2—C1—C6—C5	177.59 (18)	C27—C22—C23—C24	−0.5 (3)
C2—C1—C6—C5	0.5 (3)	C9—C22—C23—C24	178.87 (18)
O2—C1—C6—C7	−3.3 (3)	C22—C23—C24—C25	0.5 (3)
C2—C1—C6—C7	179.6 (2)	C23—C24—C25—C26	0.1 (4)
C5—C6—C7—O1	−5.5 (3)	C24—C25—C26—C27	−0.7 (4)
C1—C6—C7—O1	175.4 (2)	C25—C26—C27—C22	0.7 (3)
C5—C6—C7—C8	172.8 (2)	C23—C22—C27—C26	−0.1 (3)
C1—C6—C7—C8	−6.4 (4)	C9—C22—C27—C26	−179.52 (18)
C1—O2—C9—C22	−40.9 (2)	O2—C9—C10—C15	−45.7 (2)
C1—O2—C9—C16	87.8 (2)	C22—C9—C10—C15	−162.49 (17)
C1—O2—C9—C10	−158.66 (16)	C16—C9—C10—C15	70.9 (2)
O2—C9—C16—C21	−7.0 (2)	O2—C9—C10—C11	140.23 (18)
C22—C9—C16—C21	118.0 (2)	C22—C9—C10—C11	23.4 (2)
C10—C9—C16—C21	−118.67 (19)	C16—C9—C10—C11	−103.2 (2)
O2—C9—C16—C17	169.50 (16)	C15—C10—C11—C12	0.2 (3)
C22—C9—C16—C17	−65.5 (2)	C9—C10—C11—C12	174.41 (19)
C10—C9—C16—C17	57.8 (2)	C10—C11—C12—C13	−0.4 (3)
C17—C16—C21—C20	2.6 (3)	C11—C12—C13—C14	0.7 (4)
C9—C16—C21—C20	179.15 (19)	C12—C13—C14—C15	−0.8 (4)
C16—C21—C20—C19	−1.4 (3)	C13—C14—C15—C10	0.6 (3)
C21—C20—C19—C18	−0.3 (4)	C11—C10—C15—C14	−0.4 (3)
C20—C19—C18—C17	0.8 (4)	C9—C10—C15—C14	−174.67 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1i	0.93	2.56	3.444 (3)	158
C21—H21···O2	0.93	2.46	2.810 (3)	103
C5—H5···O1	0.93	2.36	2.701 (3)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O1i	0.93	2.56	3.444 (3)	158
C21—H21⋯O2	0.93	2.46	2.810 (3)	103
C5—H5⋯O1	0.93	2.36	2.701 (3)	101

Symmetry code: (i) .