1,3-Dibenz-yloxy-5-(bromo-meth-yl)benzene.

In the title compound, C(21)H(19)BrO(2), the dihedral angles between the central benzene ring and the two peripheral rings are 50.28 (5) and 69.75 (2)°. The O-CH(2) bonds lie in the plane of the central ring and adopt a syn-anti conformation.

Related literature

For related compounds, see: Pan et al. (2005 ▶); Xiao et al. (2007 ▶); For the synthesis, see: Hawker & Fréchet (1990 ▶).

Experimental

Crystal data

C21H19BrO2

M = 383.27

Triclinic,

a = 4.4449 (17) Å

b = 11.982 (5) Å

c = 16.726 (6) Å

α = 86.834 (7)°

β = 87.509 (7)°

γ = 86.524 (7)°

V = 887.1 (6) Å3

Z = 2

Mo Kα radiation

μ = 2.33 mm−1

T = 298 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.653, T max = 0.801

4223 measured reflections

3030 independent reflections

2199 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.090

S = 1.02

3030 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: XP in SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009672/hg2488sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009672/hg2488Isup2.hkl

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

C21H19BrO2	Z = 2
Mr = 383.27	F(000) = 392
Triclinic, P1	Dx = 1.435 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.4449 (17) Å	Cell parameters from 1804 reflections
b = 11.982 (5) Å	θ = 2.4–25.7°
c = 16.726 (6) Å	µ = 2.33 mm−1
α = 86.834 (7)°	T = 298 K
β = 87.509 (7)°	Needle, colorless
γ = 86.524 (7)°	0.20 × 0.15 × 0.10 mm
V = 887.1 (6) Å3

Bruker APEXII CCD area-detector diffractometer	3030 independent reflections
Radiation source: fine-focus sealed tube	2199 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 0 pixels mm-1	θmax = 25.0°, θmin = 2.2°
φ and ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −13→14
Tmin = 0.653, Tmax = 0.801	l = −19→16
4223 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0439P)2] where P = (Fo2 + 2Fc2)/3
3030 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.40 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
Br1	1.29871 (8)	0.68293 (3)	0.023543 (18)	0.07695 (18)
O1	0.8518 (4)	0.63235 (14)	0.34038 (10)	0.0550 (5)
O2	0.9591 (4)	0.27865 (14)	0.22300 (11)	0.0564 (5)
C19	0.7393 (9)	−0.1122 (3)	0.2047 (3)	0.0876 (12)
H19	0.6533	−0.1810	0.2129	0.105*
C5	0.9054 (6)	0.4506 (2)	0.28173 (14)	0.0425 (6)
H5	0.7738	0.4187	0.3200	0.051*
C12	0.4165 (10)	0.8523 (4)	0.5579 (2)	0.0898 (12)
H12	0.3621	0.9099	0.5917	0.108*
C6	1.0397 (6)	0.3871 (2)	0.22160 (15)	0.0428 (6)
C2	1.2996 (5)	0.5448 (2)	0.16780 (14)	0.0402 (6)
C4	0.9692 (6)	0.5614 (2)	0.28420 (14)	0.0422 (6)
C9	0.5721 (6)	0.6814 (2)	0.45747 (15)	0.0467 (6)
C16	0.9864 (6)	0.0932 (2)	0.18116 (17)	0.0502 (7)
C7	1.2350 (6)	0.4338 (2)	0.16442 (14)	0.0425 (6)
H7	1.3223	0.3908	0.1240	0.051*
C3	1.1667 (6)	0.6085 (2)	0.22694 (14)	0.0427 (6)
H3	1.2089	0.6834	0.2287	0.051*
C10	0.3915 (7)	0.7726 (3)	0.43176 (19)	0.0670 (9)
H10	0.3194	0.7761	0.3803	0.080*
C8	0.6577 (6)	0.5895 (2)	0.40320 (15)	0.0493 (7)
H8A	0.7606	0.5275	0.4326	0.059*
H8B	0.4789	0.5627	0.3812	0.059*
C17	0.9854 (8)	0.0362 (3)	0.2548 (2)	0.0673 (9)
H17	1.0693	0.0677	0.2976	0.081*
C15	1.1188 (7)	0.2048 (2)	0.16995 (17)	0.0560 (7)
H15A	1.3311	0.1981	0.1818	0.067*
H15B	1.1004	0.2336	0.1149	0.067*
C18	0.8630 (9)	−0.0662 (3)	0.2663 (2)	0.0809 (10)
H18	0.8654	−0.1037	0.3165	0.097*
C14	0.6715 (8)	0.6790 (3)	0.53462 (17)	0.0669 (8)
H14	0.7948	0.6184	0.5531	0.080*
C13	0.5932 (10)	0.7634 (3)	0.5845 (2)	0.0875 (12)
H13	0.6611	0.7597	0.6364	0.105*
C11	0.3172 (9)	0.8579 (3)	0.4810 (2)	0.0894 (11)
H11	0.1990	0.9199	0.4626	0.107*
C1	1.5149 (6)	0.5949 (2)	0.10714 (15)	0.0523 (7)
H1A	1.6408	0.5358	0.0831	0.063*
H1B	1.6449	0.6426	0.1333	0.063*
C20	0.7390 (10)	−0.0585 (3)	0.1296 (3)	0.0965 (13)
H20	0.6564	−0.0909	0.0870	0.116*
C21	0.8642 (9)	0.0451 (3)	0.1187 (2)	0.0784 (10)
H21	0.8649	0.0821	0.0683	0.094*

	U11	U22	U33	U12	U13	U23
Br1	0.0785 (3)	0.0946 (3)	0.0517 (2)	0.01328 (19)	0.01038 (15)	0.02101 (17)
O1	0.0725 (13)	0.0473 (11)	0.0460 (11)	−0.0111 (10)	0.0159 (9)	−0.0164 (9)
O2	0.0716 (13)	0.0400 (11)	0.0572 (12)	−0.0051 (9)	0.0170 (10)	−0.0124 (9)
C19	0.083 (3)	0.052 (2)	0.129 (4)	−0.0135 (19)	0.010 (2)	−0.024 (2)
C5	0.0473 (16)	0.0435 (15)	0.0366 (14)	−0.0023 (12)	0.0006 (11)	−0.0030 (11)
C12	0.108 (3)	0.085 (3)	0.080 (3)	−0.019 (2)	0.034 (2)	−0.050 (2)
C6	0.0455 (15)	0.0430 (16)	0.0404 (14)	0.0007 (12)	−0.0035 (12)	−0.0077 (12)
C2	0.0348 (14)	0.0499 (16)	0.0364 (13)	−0.0010 (12)	−0.0070 (11)	−0.0034 (12)
C4	0.0452 (15)	0.0466 (16)	0.0353 (13)	0.0001 (12)	−0.0032 (11)	−0.0088 (12)
C9	0.0504 (17)	0.0514 (16)	0.0380 (14)	−0.0055 (13)	0.0068 (12)	−0.0046 (12)
C16	0.0511 (17)	0.0415 (16)	0.0582 (18)	0.0036 (13)	0.0017 (13)	−0.0140 (14)
C7	0.0461 (16)	0.0450 (16)	0.0363 (14)	0.0047 (12)	−0.0003 (11)	−0.0096 (11)
C3	0.0459 (15)	0.0436 (15)	0.0392 (14)	−0.0052 (12)	−0.0025 (12)	−0.0053 (12)
C10	0.071 (2)	0.071 (2)	0.0597 (19)	0.0100 (18)	−0.0068 (16)	−0.0173 (17)
C8	0.0568 (18)	0.0486 (16)	0.0419 (15)	−0.0026 (14)	0.0053 (13)	−0.0030 (12)
C17	0.081 (2)	0.058 (2)	0.065 (2)	−0.0096 (17)	−0.0008 (17)	−0.0114 (16)
C15	0.0654 (19)	0.0506 (17)	0.0520 (17)	−0.0011 (15)	0.0092 (14)	−0.0154 (14)
C18	0.095 (3)	0.060 (2)	0.086 (3)	−0.003 (2)	0.010 (2)	−0.004 (2)
C14	0.090 (2)	0.065 (2)	0.0463 (17)	−0.0059 (17)	−0.0089 (15)	−0.0032 (15)
C13	0.130 (3)	0.091 (3)	0.0449 (19)	−0.025 (3)	0.004 (2)	−0.019 (2)
C11	0.096 (3)	0.069 (2)	0.102 (3)	0.019 (2)	0.007 (2)	−0.029 (2)
C1	0.0479 (17)	0.0649 (18)	0.0443 (15)	−0.0028 (14)	−0.0011 (12)	−0.0059 (14)
C20	0.108 (3)	0.074 (3)	0.115 (4)	−0.012 (2)	−0.026 (3)	−0.045 (3)
C21	0.100 (3)	0.063 (2)	0.075 (2)	0.004 (2)	−0.0199 (19)	−0.0196 (18)

Br1—C1	1.955 (3)	C16—C17	1.374 (4)
O1—C4	1.368 (3)	C16—C15	1.493 (4)
O1—C8	1.424 (3)	C7—H7	0.9300
O2—C6	1.368 (3)	C3—H3	0.9300
O2—C15	1.425 (3)	C10—C11	1.364 (4)
C19—C18	1.348 (5)	C10—H10	0.9300
C19—C20	1.379 (6)	C8—H8A	0.9700
C19—H19	0.9300	C8—H8B	0.9700
C5—C4	1.377 (4)	C17—C18	1.372 (5)
C5—C6	1.387 (3)	C17—H17	0.9300
C5—H5	0.9300	C15—H15A	0.9700
C12—C13	1.352 (5)	C15—H15B	0.9700
C12—C11	1.375 (5)	C18—H18	0.9300
C12—H12	0.9300	C14—C13	1.365 (4)
C6—C7	1.381 (4)	C14—H14	0.9300
C2—C3	1.374 (3)	C13—H13	0.9300
C2—C7	1.383 (4)	C11—H11	0.9300
C2—C1	1.491 (4)	C1—H1A	0.9700
C4—C3	1.391 (4)	C1—H1B	0.9700
C9—C10	1.376 (4)	C20—C21	1.390 (5)
C9—C14	1.380 (4)	C20—H20	0.9300
C9—C8	1.487 (3)	C21—H21	0.9300
C16—C21	1.368 (4)
C4—O1—C8	118.8 (2)	C9—C8—H8A	110.1
C6—O2—C15	118.0 (2)	O1—C8—H8B	110.1
C18—C19—C20	120.7 (4)	C9—C8—H8B	110.1
C18—C19—H19	119.7	H8A—C8—H8B	108.4
C20—C19—H19	119.7	C18—C17—C16	121.3 (3)
C4—C5—C6	119.3 (3)	C18—C17—H17	119.3
C4—C5—H5	120.4	C16—C17—H17	119.3
C6—C5—H5	120.4	O2—C15—C16	108.0 (2)
C13—C12—C11	120.1 (3)	O2—C15—H15A	110.1
C13—C12—H12	119.9	C16—C15—H15A	110.1
C11—C12—H12	119.9	O2—C15—H15B	110.1
O2—C6—C7	123.9 (2)	C16—C15—H15B	110.1
O2—C6—C5	115.2 (2)	H15A—C15—H15B	108.4
C7—C6—C5	120.8 (2)	C19—C18—C17	119.8 (4)
C3—C2—C7	120.1 (2)	C19—C18—H18	120.1
C3—C2—C1	120.2 (2)	C17—C18—H18	120.1
C7—C2—C1	119.7 (2)	C13—C14—C9	121.6 (3)
O1—C4—C5	124.8 (2)	C13—C14—H14	119.2
O1—C4—C3	115.2 (2)	C9—C14—H14	119.2
C5—C4—C3	120.1 (2)	C12—C13—C14	119.6 (3)
C10—C9—C14	117.8 (3)	C12—C13—H13	120.2
C10—C9—C8	120.6 (2)	C14—C13—H13	120.2
C14—C9—C8	121.6 (3)	C10—C11—C12	120.2 (4)
C21—C16—C17	118.5 (3)	C10—C11—H11	119.9
C21—C16—C15	121.0 (3)	C12—C11—H11	119.9
C17—C16—C15	120.5 (3)	C2—C1—Br1	110.84 (18)
C6—C7—C2	119.5 (2)	C2—C1—H1A	109.5
C6—C7—H7	120.3	Br1—C1—H1A	109.5
C2—C7—H7	120.3	C2—C1—H1B	109.5
C2—C3—C4	120.2 (2)	Br1—C1—H1B	109.5
C2—C3—H3	119.9	H1A—C1—H1B	108.1
C4—C3—H3	119.9	C19—C20—C21	118.9 (4)
C11—C10—C9	120.7 (3)	C19—C20—H20	120.5
C11—C10—H10	119.7	C21—C20—H20	120.5
C9—C10—H10	119.7	C16—C21—C20	120.7 (4)
O1—C8—C9	108.1 (2)	C16—C21—H21	119.6
O1—C8—H8A	110.1	C20—C21—H21	119.6