1-[(5-Bromo-pent-yloxy)meth-yl]pyrene.

In the title compound, C(22)H(21)BrO, other than the Br atom, the non-H atoms are approximately co-planar [maxium deviation = 0.178 (2) Å] and the alk-oxy chain shows an all-anti conformation. A weak inter-molecular C-H⋯Br hydrogen bond contributes to the stabilization of the crystal structure.

Related literature

For the synthesis of pyrene derivatives, see Filby & Steed (2006 ▶). For the use of pyrenes as fluorescence sensors, see: Bell & Hext (2004 ▶). For related structures, see: Fun et al. (2009 ▶); Gruber et al. (2010 ▶); Xiao et al. (2005 ▶).

Experimental

Crystal data

C22H21BrO

M = 381.30

Triclinic,

a = 7.417 (2) Å

b = 7.4817 (16) Å

c = 17.545 (5) Å

α = 79.924 (19)°

β = 88.90 (2)°

γ = 64.295 (12)°

V = 861.9 (4) Å3

Z = 2

Mo Kα radiation

μ = 2.39 mm−1

T = 223 K

0.45 × 0.40 × 0.20 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.373, T max = 0.616

7097 measured reflections

3085 independent reflections

2399 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.047

S = 0.88

3085 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 2005 ▶); 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: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018253/ng5165sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018253/ng5165Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018253/ng5165Isup3.cml

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

C22H21BrO	Z = 2
Mr = 381.30	F(000) = 392
Triclinic, P1	Dx = 1.469 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 7.417 (2) Å	Cell parameters from 4242 reflections
b = 7.4817 (16) Å	θ = 3.1–27.5°
c = 17.545 (5) Å	µ = 2.39 mm−1
α = 79.924 (19)°	T = 223 K
β = 88.90 (2)°	Block, colorless
γ = 64.295 (12)°	0.45 × 0.40 × 0.20 mm
V = 861.9 (4) Å3

Rigaku Saturn diffractometer	3085 independent reflections
Radiation source: fine-focus sealed tube	2399 reflections with I > 2σ(I)
graphite	Rint = 0.038
Detector resolution: 14.63 pixels mm-1	θmax = 25.5°, θmin = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −9→9
Tmin = 0.373, Tmax = 0.616	l = −21→21
7097 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.047	H-atom parameters constrained
S = 0.88	w = 1/[σ2(Fo2) + (0.0129P)2] where P = (Fo2 + 2Fc2)/3
3085 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.36 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	0.30010 (4)	0.85258 (4)	0.015557 (11)	0.04908 (9)
O1	0.35680 (18)	0.46204 (17)	0.40464 (6)	0.0263 (3)
C1	0.2422 (3)	0.4448 (3)	0.53439 (9)	0.0217 (4)
C2	0.3303 (3)	0.2367 (3)	0.54290 (9)	0.0246 (4)
H2	0.3941	0.1767	0.5010	0.030*
C3	0.3272 (3)	0.1144 (3)	0.61153 (9)	0.0272 (4)
H3	0.3891	−0.0266	0.6156	0.033*
C4	0.2324 (3)	0.1992 (3)	0.67517 (9)	0.0222 (4)
C5	0.2242 (3)	0.0795 (3)	0.74734 (9)	0.0278 (4)
H5	0.2844	−0.0619	0.7528	0.033*
C6	0.1319 (3)	0.1649 (3)	0.80776 (9)	0.0285 (4)
H6	0.1286	0.0818	0.8541	0.034*
C7	0.0391 (3)	0.3794 (3)	0.80237 (9)	0.0250 (4)
C8	−0.0539 (3)	0.4721 (3)	0.86452 (10)	0.0308 (5)
H8	−0.0562	0.3920	0.9119	0.037*
C9	−0.1421 (3)	0.6798 (3)	0.85704 (10)	0.0368 (5)
H9	−0.2031	0.7393	0.8994	0.044*
C10	−0.1415 (3)	0.8005 (3)	0.78816 (10)	0.0344 (5)
H10	−0.2032	0.9416	0.7840	0.041*
C11	−0.0503 (3)	0.7163 (3)	0.72412 (9)	0.0266 (4)
C12	−0.0449 (3)	0.8358 (3)	0.65197 (10)	0.0300 (4)
H12	−0.1070	0.9772	0.6464	0.036*
C13	0.0471 (3)	0.7513 (3)	0.59160 (10)	0.0274 (4)
H13	0.0481	0.8352	0.5451	0.033*
C14	0.1431 (3)	0.5368 (3)	0.59663 (9)	0.0209 (4)
C15	0.1394 (2)	0.4125 (3)	0.66725 (9)	0.0203 (4)
C16	0.0418 (3)	0.5033 (3)	0.73151 (9)	0.0218 (4)
C17	0.2486 (3)	0.5781 (3)	0.46037 (9)	0.0248 (4)
H17A	0.1114	0.6679	0.4390	0.030*
H17B	0.3122	0.6620	0.4716	0.030*
C18	0.3537 (3)	0.5952 (3)	0.33503 (9)	0.0240 (4)
H18A	0.4167	0.6799	0.3461	0.029*
H18B	0.2145	0.6839	0.3158	0.029*
C19	0.4640 (3)	0.4774 (3)	0.27364 (9)	0.0238 (4)
H19A	0.4014	0.3925	0.2625	0.029*
H19B	0.6035	0.3893	0.2925	0.029*
C20	0.4582 (3)	0.6222 (3)	0.19985 (9)	0.0254 (4)
H20A	0.3180	0.7134	0.1830	0.030*
H20B	0.5232	0.7045	0.2117	0.030*
C21	0.5605 (3)	0.5177 (3)	0.13337 (9)	0.0289 (4)
H21A	0.6977	0.4188	0.1515	0.035*
H21B	0.4890	0.4438	0.1188	0.035*
C22	0.5683 (3)	0.6598 (3)	0.06263 (10)	0.0380 (5)
H22A	0.6453	0.5811	0.0242	0.046*
H22B	0.6387	0.7348	0.0770	0.046*

	U11	U22	U33	U12	U13	U23
Br1	0.06041 (17)	0.05227 (16)	0.02991 (11)	−0.02606 (13)	−0.00843 (10)	0.00909 (9)
O1	0.0320 (8)	0.0235 (7)	0.0188 (6)	−0.0089 (6)	0.0073 (6)	−0.0022 (5)
C1	0.0203 (10)	0.0251 (11)	0.0197 (8)	−0.0110 (9)	−0.0006 (7)	−0.0007 (8)
C2	0.0273 (11)	0.0246 (11)	0.0209 (8)	−0.0098 (9)	0.0045 (8)	−0.0058 (8)
C3	0.0318 (12)	0.0187 (11)	0.0280 (9)	−0.0085 (9)	0.0022 (8)	−0.0038 (8)
C4	0.0226 (10)	0.0226 (11)	0.0210 (8)	−0.0101 (9)	−0.0007 (8)	−0.0027 (8)
C5	0.0329 (12)	0.0193 (11)	0.0274 (9)	−0.0099 (10)	−0.0009 (9)	0.0016 (8)
C6	0.0323 (12)	0.0316 (12)	0.0214 (9)	−0.0170 (10)	0.0001 (8)	0.0037 (8)
C7	0.0243 (11)	0.0351 (12)	0.0199 (8)	−0.0173 (10)	0.0025 (8)	−0.0042 (8)
C8	0.0331 (12)	0.0414 (13)	0.0229 (9)	−0.0217 (11)	0.0066 (9)	−0.0039 (9)
C9	0.0422 (13)	0.0464 (14)	0.0310 (10)	−0.0243 (12)	0.0161 (10)	−0.0184 (10)
C10	0.0384 (13)	0.0284 (12)	0.0384 (11)	−0.0135 (10)	0.0135 (10)	−0.0154 (9)
C11	0.0274 (11)	0.0275 (12)	0.0274 (9)	−0.0133 (10)	0.0052 (8)	−0.0084 (8)
C12	0.0350 (12)	0.0179 (11)	0.0333 (10)	−0.0076 (10)	0.0082 (9)	−0.0066 (8)
C13	0.0332 (11)	0.0240 (11)	0.0223 (9)	−0.0119 (10)	0.0025 (8)	0.0005 (8)
C14	0.0202 (10)	0.0225 (11)	0.0199 (8)	−0.0100 (9)	−0.0005 (7)	−0.0024 (8)
C15	0.0192 (10)	0.0236 (11)	0.0186 (8)	−0.0101 (9)	0.0003 (7)	−0.0026 (7)
C16	0.0199 (10)	0.0257 (11)	0.0214 (8)	−0.0118 (9)	0.0005 (7)	−0.0037 (8)
C17	0.0255 (11)	0.0267 (11)	0.0206 (8)	−0.0099 (9)	0.0036 (8)	−0.0044 (8)
C18	0.0272 (11)	0.0251 (11)	0.0179 (8)	−0.0114 (9)	0.0013 (8)	0.0008 (8)
C19	0.0255 (11)	0.0236 (11)	0.0215 (8)	−0.0106 (9)	0.0020 (8)	−0.0022 (8)
C20	0.0287 (11)	0.0274 (11)	0.0200 (8)	−0.0121 (9)	0.0049 (8)	−0.0054 (8)
C21	0.0320 (11)	0.0321 (12)	0.0216 (8)	−0.0139 (10)	0.0039 (8)	−0.0033 (8)
C22	0.0406 (13)	0.0491 (14)	0.0252 (9)	−0.0213 (11)	0.0063 (9)	−0.0050 (9)

Br1—C22	1.969 (2)	C11—C16	1.418 (2)
O1—C17	1.4200 (19)	C11—C12	1.427 (2)
O1—C18	1.4283 (19)	C12—C13	1.349 (2)
C1—C2	1.383 (2)	C12—H12	0.9400
C1—C14	1.414 (2)	C13—C14	1.433 (2)
C1—C17	1.506 (2)	C13—H13	0.9400
C2—C3	1.386 (2)	C14—C15	1.421 (2)
C2—H2	0.9400	C15—C16	1.437 (2)
C3—C4	1.405 (2)	C17—H17A	0.9800
C3—H3	0.9400	C17—H17B	0.9800
C4—C15	1.419 (2)	C18—C19	1.510 (2)
C4—C5	1.434 (2)	C18—H18A	0.9800
C5—C6	1.353 (2)	C18—H18B	0.9800
C5—H5	0.9400	C19—C20	1.524 (2)
C6—C7	1.432 (3)	C19—H19A	0.9800
C6—H6	0.9400	C19—H19B	0.9800
C7—C8	1.402 (2)	C20—C21	1.523 (2)
C7—C16	1.420 (2)	C20—H20A	0.9800
C8—C9	1.382 (3)	C20—H20B	0.9800
C8—H8	0.9400	C21—C22	1.504 (2)
C9—C10	1.378 (3)	C21—H21A	0.9800
C9—H9	0.9400	C21—H21B	0.9800
C10—C11	1.402 (2)	C22—H22A	0.9800
C10—H10	0.9400	C22—H22B	0.9800
C17—O1—C18	109.08 (13)	C4—C15—C14	120.57 (15)
C2—C1—C14	119.58 (16)	C4—C15—C16	119.62 (15)
C2—C1—C17	121.89 (15)	C14—C15—C16	119.80 (16)
C14—C1—C17	118.53 (16)	C11—C16—C7	120.18 (15)
C1—C2—C3	121.76 (16)	C11—C16—C15	119.89 (16)
C1—C2—H2	119.1	C7—C16—C15	119.94 (16)
C3—C2—H2	119.1	O1—C17—C1	111.32 (14)
C2—C3—C4	120.58 (17)	O1—C17—H17A	109.4
C2—C3—H3	119.7	C1—C17—H17A	109.4
C4—C3—H3	119.7	O1—C17—H17B	109.4
C3—C4—C15	118.45 (15)	C1—C17—H17B	109.4
C3—C4—C5	122.80 (16)	H17A—C17—H17B	108.0
C15—C4—C5	118.75 (15)	O1—C18—C19	110.73 (14)
C6—C5—C4	121.65 (17)	O1—C18—H18A	109.5
C6—C5—H5	119.2	C19—C18—H18A	109.5
C4—C5—H5	119.2	O1—C18—H18B	109.5
C5—C6—C7	121.20 (16)	C19—C18—H18B	109.5
C5—C6—H6	119.4	H18A—C18—H18B	108.1
C7—C6—H6	119.4	C18—C19—C20	109.88 (15)
C8—C7—C16	118.66 (17)	C18—C19—H19A	109.7
C8—C7—C6	122.51 (16)	C20—C19—H19A	109.7
C16—C7—C6	118.83 (15)	C18—C19—H19B	109.7
C9—C8—C7	120.82 (17)	C20—C19—H19B	109.7
C9—C8—H8	119.6	H19A—C19—H19B	108.2
C7—C8—H8	119.6	C21—C20—C19	113.91 (15)
C10—C9—C8	120.69 (16)	C21—C20—H20A	108.8
C10—C9—H9	119.7	C19—C20—H20A	108.8
C8—C9—H9	119.7	C21—C20—H20B	108.8
C9—C10—C11	121.02 (18)	C19—C20—H20B	108.8
C9—C10—H10	119.5	H20A—C20—H20B	107.7
C11—C10—H10	119.5	C22—C21—C20	113.79 (15)
C10—C11—C16	118.63 (16)	C22—C21—H21A	108.8
C10—C11—C12	122.79 (17)	C20—C21—H21A	108.8
C16—C11—C12	118.58 (15)	C22—C21—H21B	108.8
C13—C12—C11	121.76 (17)	C20—C21—H21B	108.8
C13—C12—H12	119.1	H21A—C21—H21B	107.7
C11—C12—H12	119.1	C21—C22—Br1	112.67 (13)
C12—C13—C14	121.56 (16)	C21—C22—H22A	109.1
C12—C13—H13	119.2	Br1—C22—H22A	109.1
C14—C13—H13	119.2	C21—C22—H22B	109.1
C1—C14—C15	119.04 (16)	Br1—C22—H22B	109.1
C1—C14—C13	122.55 (16)	H22A—C22—H22B	107.8
C15—C14—C13	118.41 (15)
C14—C1—C2—C3	−1.0 (3)	C3—C4—C15—C16	−179.80 (15)
C17—C1—C2—C3	178.85 (15)	C5—C4—C15—C16	0.8 (2)
C1—C2—C3—C4	0.3 (3)	C1—C14—C15—C4	−0.4 (2)
C2—C3—C4—C15	0.3 (2)	C13—C14—C15—C4	−179.97 (15)
C2—C3—C4—C5	179.71 (16)	C1—C14—C15—C16	179.12 (14)
C3—C4—C5—C6	−179.99 (16)	C13—C14—C15—C16	−0.5 (2)
C15—C4—C5—C6	−0.6 (2)	C10—C11—C16—C7	0.6 (3)
C4—C5—C6—C7	−0.4 (3)	C12—C11—C16—C7	−179.87 (15)
C5—C6—C7—C8	−178.58 (16)	C10—C11—C16—C15	−178.99 (15)
C5—C6—C7—C16	1.2 (3)	C12—C11—C16—C15	0.5 (2)
C16—C7—C8—C9	0.3 (3)	C8—C7—C16—C11	−0.8 (2)
C6—C7—C8—C9	−179.91 (17)	C6—C7—C16—C11	179.42 (16)
C7—C8—C9—C10	0.3 (3)	C8—C7—C16—C15	178.81 (15)
C8—C9—C10—C11	−0.5 (3)	C6—C7—C16—C15	−0.9 (2)
C9—C10—C11—C16	0.0 (3)	C4—C15—C16—C11	179.61 (15)
C9—C10—C11—C12	−179.44 (17)	C14—C15—C16—C11	0.1 (2)
C10—C11—C12—C13	178.72 (17)	C4—C15—C16—C7	0.0 (2)
C16—C11—C12—C13	−0.7 (3)	C14—C15—C16—C7	−179.54 (14)
C11—C12—C13—C14	0.4 (3)	C18—O1—C17—C1	178.43 (13)
C2—C1—C14—C15	1.0 (2)	C2—C1—C17—O1	−1.1 (2)
C17—C1—C14—C15	−178.83 (14)	C14—C1—C17—O1	178.76 (13)
C2—C1—C14—C13	−179.42 (16)	C17—O1—C18—C19	−178.88 (13)
C17—C1—C14—C13	0.7 (2)	O1—C18—C19—C20	179.77 (13)
C12—C13—C14—C1	−179.34 (16)	C18—C19—C20—C21	−178.27 (14)
C12—C13—C14—C15	0.2 (3)	C19—C20—C21—C22	−175.62 (14)
C3—C4—C15—C14	−0.3 (2)	C20—C21—C22—Br1	−63.25 (17)
C5—C4—C15—C14	−179.68 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Br1i	0.94	3.02	3.869 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Br1i	0.94	3.02	3.869 (2)	151

Symmetry code: (i) .