1-Bromo-2,7-di-tert-butyl­pyrene

Xia, G.-M.; Liu, Z.-Q.; Lu, P.; Sun, G.-X.; Chen, H.-Y.

doi:10.1107/S1600536809054257

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o216

doi:10.1107/S1600536809054257

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1-Bromo-2,7-di-tert-butylpyrene

Guang-Ming Xia,^a ^* Zhi-Qiang Liu,^b Ping Lu,^a Guo-Xin Sun ^a and Hong-Yu Chen ^c

^aSchool of Chemistry and Chemical Engineering, University of Jinan, Ji'nan 250022, People's Republic of China, ^bState Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, Shandong Province, People's Republic of China, and ^cSchool of Chemistry and Chemical Engineering, TaiShan Medical University, Tai'an 271016, People's Republic of China
^*Correspondence e-mail: chm_xiagm@ujn.edu.cn

(Received 7 December 2009; accepted 16 December 2009; online 19 December 2009)

In the title molecule, C₂₄H₂₅Br, one of two tert-butyl groups is rotationally disordered between two orientations in a 0.59 (3):0.41 (3) ratio. The crystal packing exhibits no π–π interactions; however, relatively short intermolecular Br⋯Br contacts of 3.654 (1) Å are observed.

Related literature

For the synthesis, see: Yamato et al. (1997 ). For a related structure, see: Hazell & Lomborg (1972 ).

Experimental

Crystal data

C₂₄H₂₅Br
M_r = 393.35
Orthorhombic, P c a 2₁
a = 21.4678 (4) Å
b = 14.5221 (2) Å
c = 6.2436 (1) Å
V = 1946.49 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.12 mm⁻¹
T = 293 K
0.32 × 0.21 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.643, T_max = 0.651
15786 measured reflections
4402 independent reflections
2741 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.090
wR(F²) = 0.281
S = 1.00
4402 reflections
263 parameters
67 restraints
H-atom parameters constrained
Δρ_max = 1.01 e Å⁻³
Δρ_min = −0.84 e Å⁻³
Absolute structure: Flack (1983 ), 1930 Friedel pairs
Flack parameter: 0.05 (3)

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054257/cv2677sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809054257/cv2677Isup2.hkl

checkCIF report

Comment top

Pyrene and its derivatives are often used as fluorescent chromophores. Normally, the electrophilic substitution of pyrene occurred at positions 1, 3, 6 or 8 position, but not at other positions (2,4,5,7,9 and 10). However, the orientation in friedel-crafts tert-butylation of pyrene have been proved at positions 2 and 7. Yamato and co workers had reported that the bromination of 2,7-di-tert-butylpyrene with 1 mol equiv of bromine in carbon tetrachloride solution afford 1-bromo-2,7-di-tert-butylpyrene in high yield (Yamato et al., 1997). However, no crystal data were given as a proof. Herein, we report the crystal structure of 1-bromo-2,7-di-tert-butylpyrene, (I), which support the conclusion of Yamato.

In (I) (Fig. 1), all bond lengths and angles are normal and comparable to those reported for close compound (Hazell et al., 1972). One of two tert-butyl groups (attached to pyrene at position 7) is rotationally disordered between two orientations in a ratio 0.59 (3):0.41 (3). The crystal packing exhibits no π-π interactions, however, relatively short intermolecular Br···Br contacts of 3.654 (1) are observed.

Related literature top

For the synthesis, see: Yamato et al. (1997). For a related structure, see: Hazell et al. (1972).

Experimental top

The title compound was synthesized by the bromination of 2,7-di-tert-butylpyrene. To a solution of 2,7-di-tert-butylpyrene(314 mg, 1.0 mmol) in 30 ml CCl₄, a solution of Br₂ (200 mg, 1.1 mmol) in 10 ml CCl₄ was added at 0°C. After the reaction mixture had been stirred for 1 h at room temperature, it was poured into water and the organic layer was extracted with CH₂Cl₂ and washed with solution of sodium thiosulfate and water, dried over MgSO₄ and concentrated. The residue was purified by silica gel column chromatography with hexane as eluent t o afford a solid. Recrystallization from ethanol gave the 1-bromo-2,7-di-tert-butylpyrene(yield: 290 mg, 75%) as colorless prism crystals.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of the title compound showing the atomic numbering and 50% probability displacement ellipsoids. Only major parts of disordered atoms are shown. H atoms omitted for clarity.

1-Bromo-2,7-di-tert-butylpyrene top

Crystal data top

C₂₄H₂₅Br	F(000) = 816
M_r = 393.35	D_x = 1.342 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3661 reflections
a = 21.4678 (4) Å	θ = 2.8–21.3°
b = 14.5221 (2) Å	µ = 2.12 mm⁻¹
c = 6.2436 (1) Å	T = 293 K
V = 1946.49 (5) Å³	Prism, colourless
Z = 4	0.32 × 0.21 × 0.13 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4402 independent reflections
Radiation source: fine-focus sealed tube	2741 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (APEX2; Bruker, 2005)	h = −25→27
T_min = 0.643, T_max = 0.651	k = −18→18
15786 measured reflections	l = −8→8

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.090	H-atom parameters constrained
wR(F²) = 0.281	w = 1/[σ²(F_o²) + (0.1998P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
4402 reflections	Δρ_max = 1.01 e Å⁻³
263 parameters	Δρ_min = −0.84 e Å⁻³
67 restraints	Absolute structure: Flack (1983), 1930 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (3)

Crystal data top

C₂₄H₂₅Br	V = 1946.49 (5) Å³
M_r = 393.35	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 21.4678 (4) Å	µ = 2.12 mm⁻¹
b = 14.5221 (2) Å	T = 293 K
c = 6.2436 (1) Å	0.32 × 0.21 × 0.13 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4402 independent reflections
Absorption correction: multi-scan (APEX2; Bruker, 2005)	2741 reflections with I > 2σ(I)
T_min = 0.643, T_max = 0.651	R_int = 0.037
15786 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.090	H-atom parameters constrained
wR(F²) = 0.281	Δρ_max = 1.01 e Å⁻³
S = 1.00	Δρ_min = −0.84 e Å⁻³
4402 reflections	Absolute structure: Flack (1983), 1930 Friedel pairs
263 parameters	Absolute structure parameter: 0.05 (3)
67 restraints

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	Occ. (<1)
Br1	0.70576 (5)	0.22447 (6)	0.7036 (4)	0.0927 (5)
C1	0.5691 (4)	0.0248 (5)	0.2951 (17)	0.080 (2)
H1A	0.5861	0.0122	0.1559	0.119*
H1B	0.5318	0.0605	0.2802	0.119*
H1C	0.5596	−0.0322	0.3659	0.119*
C2	0.5941 (4)	0.0721 (5)	0.6628 (15)	0.078 (2)
H2A	0.5854	0.0088	0.6960	0.116*
H2B	0.5568	0.1078	0.6790	0.116*
H2C	0.6255	0.0950	0.7583	0.116*
C3	0.6796 (4)	0.0348 (5)	0.386 (2)	0.090 (3)
H3A	0.7120	0.0690	0.4560	0.134*
H3B	0.6872	0.0342	0.2340	0.134*
H3C	0.6793	−0.0273	0.4385	0.134*
C4	0.6175 (3)	0.0794 (4)	0.4297 (12)	0.0541 (16)
C5	0.6193 (3)	0.1826 (4)	0.3626 (10)	0.0430 (13)
C6	0.6535 (3)	0.2502 (4)	0.4644 (11)	0.0481 (15)
C7	0.6560 (3)	0.3424 (4)	0.3944 (11)	0.0445 (13)
C8	0.5863 (3)	0.2102 (4)	0.1850 (14)	0.0542 (16)
H8	0.5632	0.1657	0.1131	0.065*
C9	0.5847 (3)	0.2997 (4)	0.1046 (11)	0.0470 (14)
C10	0.6206 (2)	0.3676 (4)	0.2096 (10)	0.0412 (12)
C11	0.6917 (3)	0.4127 (5)	0.4975 (12)	0.0518 (16)
H11	0.7152	0.3976	0.6177	0.062*
C12	0.6924 (3)	0.5025 (5)	0.4239 (12)	0.0534 (16)
H12	0.7152	0.5471	0.4967	0.064*
C13	0.6581 (3)	0.5270 (4)	0.2360 (11)	0.0444 (13)
C14	0.6213 (3)	0.4595 (4)	0.1356 (9)	0.0412 (12)
C15	0.5488 (4)	0.3282 (5)	−0.0776 (13)	0.070 (2)
H15	0.5243	0.2850	−0.1480	0.084*
C16	0.5495 (4)	0.4147 (5)	−0.1491 (14)	0.068 (2)
H16	0.5260	0.4293	−0.2696	0.081*
C17	0.5850 (3)	0.4861 (5)	−0.0475 (11)	0.0513 (15)
C18	0.5874 (3)	0.5748 (4)	−0.1191 (11)	0.0519 (15)
H18	0.5638	0.5904	−0.2386	0.062*
C19	0.6590 (3)	0.6164 (4)	0.1567 (11)	0.0503 (14)
H19	0.6840	0.6599	0.2244	0.060*
C20	0.6236 (3)	0.6438 (4)	−0.0222 (11)	0.0502 (15)
C21	0.6244 (3)	0.7430 (5)	−0.1038 (9)	0.0588 (18)
C22	0.6781 (6)	0.7999 (9)	−0.009 (3)	0.067 (5)	0.59 (3)
H22A	0.6705	0.8107	0.1400	0.100*	0.59 (3)
H22B	0.6809	0.8577	−0.0832	0.100*	0.59 (3)
H22C	0.7165	0.7667	−0.0261	0.100*	0.59 (3)
C23	0.5639 (5)	0.7879 (9)	−0.031 (3)	0.064 (4)	0.59 (3)
H23A	0.5298	0.7466	−0.0558	0.096*	0.59 (3)
H23B	0.5573	0.8438	−0.1096	0.096*	0.59 (3)
H23C	0.5664	0.8017	0.1194	0.096*	0.59 (3)
C24	0.6287 (9)	0.7500 (11)	−0.3457 (14)	0.073 (5)	0.59 (3)
H24A	0.6656	0.7191	−0.3942	0.109*	0.59 (3)
H24B	0.6305	0.8137	−0.3868	0.109*	0.59 (3)
H24C	0.5927	0.7218	−0.4092	0.109*	0.59 (3)
C22'	0.6879 (9)	0.790 (3)	−0.103 (6)	0.20 (3)	0.41 (3)
H22D	0.7175	0.7511	−0.0305	0.299*	0.41 (3)
H22E	0.6850	0.8477	−0.0300	0.299*	0.41 (3)
H22F	0.7014	0.7997	−0.2477	0.299*	0.41 (3)
C23'	0.5813 (12)	0.7978 (15)	0.043 (3)	0.070 (7)	0.41 (3)
H23D	0.5419	0.7669	0.0541	0.106*	0.41 (3)
H23E	0.5751	0.8583	−0.0149	0.106*	0.41 (3)
H23F	0.5998	0.8025	0.1828	0.106*	0.41 (3)
C24'	0.5979 (14)	0.7505 (15)	−0.331 (2)	0.073 (7)	0.41 (3)
H24D	0.6186	0.7072	−0.4224	0.110*	0.41 (3)
H24E	0.6044	0.8118	−0.3841	0.110*	0.41 (3)
H24F	0.5541	0.7374	−0.3280	0.110*	0.41 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1018 (8)	0.0731 (6)	0.1033 (8)	−0.0084 (4)	−0.0434 (7)	0.0225 (5)
C1	0.100 (6)	0.045 (4)	0.094 (6)	−0.017 (4)	−0.011 (5)	−0.001 (4)
C2	0.104 (6)	0.059 (4)	0.070 (5)	−0.016 (4)	0.009 (5)	0.023 (4)
C3	0.070 (5)	0.044 (4)	0.155 (10)	0.013 (4)	0.019 (6)	0.014 (5)
C4	0.062 (4)	0.038 (3)	0.062 (4)	−0.003 (3)	0.006 (3)	0.007 (3)
C5	0.047 (3)	0.043 (3)	0.039 (3)	−0.005 (2)	0.002 (3)	0.005 (2)
C6	0.052 (3)	0.042 (3)	0.050 (4)	0.006 (3)	−0.012 (3)	0.006 (3)
C7	0.045 (3)	0.039 (3)	0.049 (3)	0.006 (2)	−0.002 (3)	0.007 (3)
C8	0.070 (4)	0.039 (3)	0.054 (4)	−0.008 (3)	0.009 (4)	0.005 (3)
C9	0.054 (3)	0.042 (3)	0.045 (3)	0.000 (3)	−0.009 (3)	−0.002 (3)
C10	0.042 (3)	0.041 (3)	0.041 (3)	0.007 (2)	−0.002 (2)	−0.005 (3)
C11	0.063 (4)	0.042 (3)	0.051 (4)	−0.002 (3)	−0.022 (3)	0.004 (3)
C12	0.065 (4)	0.043 (3)	0.053 (4)	0.001 (3)	−0.013 (3)	−0.003 (3)
C13	0.045 (3)	0.039 (3)	0.049 (3)	0.007 (2)	−0.002 (3)	−0.005 (3)
C14	0.046 (3)	0.043 (3)	0.035 (3)	0.006 (2)	0.004 (2)	0.000 (2)
C15	0.100 (6)	0.061 (4)	0.050 (4)	−0.018 (4)	−0.027 (4)	−0.002 (4)
C16	0.081 (5)	0.059 (4)	0.062 (4)	−0.008 (4)	−0.032 (4)	0.004 (3)
C17	0.054 (4)	0.056 (4)	0.045 (3)	0.004 (3)	−0.006 (3)	0.002 (3)
C18	0.056 (4)	0.050 (4)	0.050 (4)	0.009 (3)	−0.006 (3)	0.010 (3)
C19	0.057 (3)	0.037 (3)	0.057 (4)	0.002 (2)	0.006 (3)	0.001 (3)
C20	0.055 (4)	0.048 (3)	0.048 (4)	0.011 (3)	0.011 (3)	0.003 (3)
C21	0.074 (5)	0.037 (3)	0.065 (5)	0.006 (3)	0.009 (4)	0.002 (3)
C22	0.067 (6)	0.060 (6)	0.073 (6)	−0.006 (4)	−0.002 (4)	0.007 (4)
C23	0.061 (5)	0.061 (5)	0.070 (6)	0.003 (4)	−0.005 (4)	0.003 (4)
C24	0.079 (6)	0.069 (6)	0.071 (6)	−0.007 (4)	0.009 (4)	0.002 (4)
C22'	0.20 (3)	0.20 (3)	0.20 (3)	0.000 (5)	0.000 (5)	0.002 (5)
C23'	0.074 (8)	0.068 (8)	0.070 (8)	0.000 (5)	−0.001 (5)	0.000 (5)
C24'	0.077 (8)	0.071 (7)	0.071 (8)	−0.001 (5)	0.004 (5)	0.008 (5)

Geometric parameters (Å, º) top

Br1—C6	1.905 (6)	C16—C17	1.435 (10)
C1—C4	1.553 (11)	C16—H16	0.9300
C1—H1A	0.9600	C17—C18	1.363 (9)
C1—H1B	0.9600	C18—C20	1.405 (10)
C1—H1C	0.9600	C18—H18	0.9300
C2—C4	1.543 (12)	C19—C20	1.409 (10)
C2—H2A	0.9600	C19—H19	0.9300
C2—H2B	0.9600	C20—C21	1.529 (9)
C2—H2C	0.9600	C21—C24	1.516 (9)
C3—C4	1.509 (10)	C21—C23	1.524 (8)
C3—H3A	0.9600	C21—C22'	1.524 (9)
C3—H3B	0.9600	C21—C23'	1.526 (9)
C3—H3C	0.9600	C21—C24'	1.530 (9)
C4—C5	1.556 (9)	C21—C22	1.536 (8)
C5—C8	1.376 (10)	C22—H22A	0.9600
C5—C6	1.382 (9)	C22—H22B	0.9600
C6—C7	1.409 (8)	C22—H22C	0.9600
C7—C11	1.430 (9)	C23—H23A	0.9600
C7—C10	1.430 (9)	C23—H23B	0.9600
C8—C9	1.394 (9)	C23—H23C	0.9600
C8—H8	0.9300	C24—H24A	0.9600
C9—C10	1.412 (8)	C24—H24B	0.9600
C9—C15	1.436 (10)	C24—H24C	0.9600
C10—C14	1.413 (8)	C22'—H22D	0.9600
C11—C12	1.383 (10)	C22'—H22E	0.9600
C11—H11	0.9300	C22'—H22F	0.9600
C12—C13	1.431 (10)	C23'—H23D	0.9600
C12—H12	0.9300	C23'—H23E	0.9600
C13—C19	1.390 (8)	C23'—H23F	0.9600
C13—C14	1.407 (8)	C24'—H24D	0.9600
C14—C17	1.437 (9)	C24'—H24E	0.9600
C15—C16	1.333 (11)	C24'—H24F	0.9600
C15—H15	0.9300

C4—C1—H1A	109.5	C18—C17—C16	123.9 (6)
C4—C1—H1B	109.5	C18—C17—C14	119.6 (6)
H1A—C1—H1B	109.5	C16—C17—C14	116.4 (6)
C4—C1—H1C	109.5	C17—C18—C20	123.6 (6)
H1A—C1—H1C	109.5	C17—C18—H18	118.2
H1B—C1—H1C	109.5	C20—C18—H18	118.2
C4—C2—H2A	109.5	C13—C19—C20	122.5 (6)
C4—C2—H2B	109.5	C13—C19—H19	118.7
H2A—C2—H2B	109.5	C20—C19—H19	118.7
C4—C2—H2C	109.5	C18—C20—C19	116.1 (6)
H2A—C2—H2C	109.5	C18—C20—C21	122.3 (6)
H2B—C2—H2C	109.5	C19—C20—C21	121.6 (6)
C4—C3—H3A	109.5	C24—C21—C23	108.8 (6)
C4—C3—H3B	109.5	C24—C21—C22'	85.3 (11)
H3A—C3—H3B	109.5	C23—C21—C22'	124.9 (16)
C4—C3—H3C	109.5	C24—C21—C23'	126.9 (11)
H3A—C3—H3C	109.5	C23—C21—C23'	23.1 (9)
H3B—C3—H3C	109.5	C22'—C21—C23'	108.0 (8)
C3—C4—C2	115.5 (8)	C24—C21—C20	113.3 (8)
C3—C4—C1	105.8 (7)	C23—C21—C20	107.2 (7)
C2—C4—C1	104.9 (7)	C22'—C21—C20	115.3 (16)
C3—C4—C5	110.0 (6)	C23'—C21—C20	106.5 (10)
C2—C4—C5	109.2 (6)	C24—C21—C24'	25.3 (8)
C1—C4—C5	111.3 (6)	C23—C21—C24'	86.0 (9)
C8—C5—C6	116.0 (5)	C22'—C21—C24'	107.7 (8)
C8—C5—C4	119.0 (5)	C23'—C21—C24'	107.1 (7)
C6—C5—C4	125.0 (6)	C20—C21—C24'	111.8 (10)
C5—C6—C7	123.6 (6)	C24—C21—C22	107.4 (6)
C5—C6—Br1	122.3 (5)	C23—C21—C22	107.1 (6)
C7—C6—Br1	114.0 (5)	C22'—C21—C22	24.1 (11)
C6—C7—C11	124.0 (6)	C23'—C21—C22	86.8 (11)
C6—C7—C10	118.2 (5)	C20—C21—C22	112.8 (7)
C11—C7—C10	117.8 (5)	C24'—C21—C22	126.5 (11)
C5—C8—C9	125.0 (6)	C21—C22—H22A	109.5
C5—C8—H8	117.5	C21—C22—H22B	109.5
C9—C8—H8	117.5	C21—C22—H22C	109.5
C8—C9—C10	118.1 (6)	C21—C23—H23A	109.5
C8—C9—C15	124.6 (6)	C21—C23—H23B	109.5
C10—C9—C15	117.3 (6)	C21—C23—H23C	109.5
C9—C10—C14	120.9 (5)	C21—C24—H24A	109.5
C9—C10—C7	119.1 (5)	C21—C24—H24B	109.5
C14—C10—C7	120.0 (5)	C21—C24—H24C	109.5
C12—C11—C7	122.0 (6)	C21—C22'—H22D	109.5
C12—C11—H11	119.0	C21—C22'—H22E	109.5
C7—C11—H11	119.0	H22D—C22'—H22E	109.5
C11—C12—C13	120.1 (6)	C21—C22'—H22F	109.5
C11—C12—H12	119.9	H22D—C22'—H22F	109.5
C13—C12—H12	119.9	H22E—C22'—H22F	109.5
C19—C13—C14	120.1 (6)	C21—C23'—H23D	109.5
C19—C13—C12	121.1 (6)	C21—C23'—H23E	109.5
C14—C13—C12	118.8 (5)	H23D—C23'—H23E	109.5
C13—C14—C10	121.2 (5)	C21—C23'—H23F	109.5
C13—C14—C17	118.1 (5)	H23D—C23'—H23F	109.5
C10—C14—C17	120.6 (5)	H23E—C23'—H23F	109.5
C16—C15—C9	122.1 (7)	C21—C24'—H24D	109.5
C16—C15—H15	118.9	C21—C24'—H24E	109.5
C9—C15—H15	118.9	H24D—C24'—H24E	109.5
C15—C16—C17	122.6 (7)	C21—C24'—H24F	109.5
C15—C16—H16	118.7	H24D—C24'—H24F	109.5
C17—C16—H16	118.7	H24E—C24'—H24F	109.5

Experimental details

Crystal data
Chemical formula	C₂₄H₂₅Br
M_r	393.35
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	21.4678 (4), 14.5221 (2), 6.2436 (1)
V (Å³)	1946.49 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.12
Crystal size (mm)	0.32 × 0.21 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (APEX2; Bruker, 2005)
T_min, T_max	0.643, 0.651
No. of measured, independent and observed [I > 2σ(I)] reflections	15786, 4402, 2741
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.090, 0.281, 1.00
No. of reflections	4402
No. of parameters	263
No. of restraints	67
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.01, −0.84
Absolute structure	Flack (1983), 1930 Friedel pairs
Absolute structure parameter	0.05 (3)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Acknowledgements

This work was supported by the Shandong Key Scientific and Technological Project (grant No. 2008 GG30002014)

References

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