1-[(5-Bromo­pent­yloxy)meth­yl]pyrene

Bian, X.; Cai, T.; Zhou, J.; Huang, Q.; Xiao, X.

doi:10.1107/S1600536811018253

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1456

doi:10.1107/S1600536811018253

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1-[(5-Bromopentyloxy)methyl]pyrene

Xixi Bian,^a Tongjiang Cai,^a Jin Zhou,^a Qin Huang ^a and Xunwen Xiao ^a ^*

^aNingbo University of Technology, Ningbo 315016, People's Republic of China
^*Correspondence e-mail: xunwenxiao@gmail.com

(Received 12 May 2011; accepted 13 May 2011; online 20 May 2011)

In the title compound, C₂₂H₂₁BrO, other than the Br atom, the non-H atoms are approximately co-planar [maxium deviation = 0.178 (2) Å] and the alkoxy chain shows an all-anti conformation. A weak intermolecular 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_r = 381.30
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.028
wR(F²) = 0.047
S = 0.88
3085 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.36 e Å⁻³

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) x, y-1, z+1.

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).

Supporting information

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

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

Supporting information file. DOI: 10.1107/S1600536811018253/ng5165Isup3.cml

checkCIF report

Comment top

As a fluorogenic unit, pyrene is one of the most useful fluorescene probe because of its relatively efficient excimer formation and emission. In this respect, the title compound was prepared as part of our research on the solid state structure of fluorogenic tetrathiafulvalene with possible molecular switch (Xiao et al.., 2005).

The bond lengths and bond angles of the title compound are found to have norml values (Fun et al.., 2009 Gruber et al.., 2010). Expect the Br atom and H atoms, the molecule is essentially planar with the maximum deviation from planarity being 0.1781 (21) Å. In the substitute alkoxy chain, expect the Br atom, it shows the typical all-anti conformation (Fig.1).

The crystal packing is stabilized by C—H···Br intermolecular hydrogen bonding (table.1) (Fig.2).

Related literature top

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 top

The title compound was synthesiaed according to a literature procedure (Xiao et al.., 2005). Slow evaporation of a solution in THF gave single crystals suitable for X–ray analysis.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); 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).

Figures top

	Fig. 1. The molecular structure of the title compound.Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing diagram view along the crystallographic 〈i〉b〈/i〉 axis. Dashed lines indicate the hydrogen bonding.

1-[(5-Bromopentyloxy)methyl]pyrene top

Crystal data top

C₂₂H₂₁BrO	Z = 2
M_r = 381.30	F(000) = 392
Triclinic, P1	D_x = 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

Data collection top

Rigaku Saturn diffractometer	3085 independent reflections
Radiation source: fine-focus sealed tube	2399 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 14.63 pixels mm^-1	θ_max = 25.5°, θ_min = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −9→9
T_min = 0.373, T_max = 0.616	l = −21→21
7097 measured reflections

Refinement top

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(F_o²) + (0.0129P)²] where P = (F_o² + 2F_c²)/3
3085 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₂H₂₁BrO	γ = 64.295 (12)°
M_r = 381.30	V = 861.9 (4) Å³
Triclinic, P1	Z = 2
a = 7.417 (2) Å	Mo Kα radiation
b = 7.4817 (16) Å	µ = 2.39 mm⁻¹
c = 17.545 (5) Å	T = 223 K
α = 79.924 (19)°	0.45 × 0.40 × 0.20 mm
β = 88.90 (2)°

Data collection top

Rigaku Saturn diffractometer	3085 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	2399 reflections with I > 2σ(I)
T_min = 0.373, T_max = 0.616	R_int = 0.038
7097 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.047	H-atom parameters constrained
S = 0.88	Δρ_max = 0.31 e Å⁻³
3085 reflections	Δρ_min = −0.36 e Å⁻³
218 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₁BrO
M_r	381.30
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	7.417 (2), 7.4817 (16), 17.545 (5)
α, β, γ (°)	79.924 (19), 88.90 (2), 64.295 (12)
V (Å³)	861.9 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.39
Crystal size (mm)	0.45 × 0.40 × 0.20

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.373, 0.616
No. of measured, independent and observed [I > 2σ(I)] reflections	7097, 3085, 2399
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.047, 0.88
No. of reflections	3085
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.36

Computer programs: CrystalClear (Rigaku, 2005), CrystalStructure (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z+1.

Acknowledgements

This work was supported by the NNS (20902051), the Education Committee of Zhejiang Province (Z200906833), Ningbo Natural Science (2010 A610186) and the Ministry of Education Scientific Research Foundation for Returned Overseas Scholars.

References

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