9-Chloro­methyl-9-[(9H-fluoren-9-yl)meth­yl]-9H-fluorene

Shen, Q.; Yu, S.-Q.; Hu, B.-B.; Lu, P.

doi:10.1107/S1600536808012117

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o996

doi:10.1107/S1600536808012117

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9-Chloromethyl-9-[(9H-fluoren-9-yl)methyl]-9H-fluorene

Qun Shen,^a Shu-Qiang Yu,^a Bin-Bin Hu ^a and Ping Lu ^a ^*

^aDepartment of Chemistry, Zhejiang University, Yuquan Campus, Hangzhou 310027, People's Republic of China
^*Correspondence e-mail: pinglu@zju.edu.cn

(Received 13 April 2008; accepted 26 April 2008; online 3 May 2008)

In the title compound, C₂₈H₂₁Cl, the dihedral angle between the two fluorene ring systems is 71.97 (4)°. There is an intramolecular C—H⋯Cl hydrogen bond. In the crystal structure, the centroid-to-centroid distance between stacked fluorene ring systems is ca 4.22 Å, which indicates that there are no π–π stacking interactions between them.

Related literature

For general background, see: Chun et al. (2003 ); Kim et al. (1998 ); Muller et al. (2003 ); Saragi et al. (2004 ).

Experimental

Crystal data

C₂₈H₂₁Cl
M_r = 392.90
Monoclinic, P 2₁ /c
a = 8.4346 (17) Å
b = 26.368 (5) Å
c = 9.1162 (18) Å
β = 94.08 (3)°
V = 2022.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 298 (2) K
0.35 × 0.29 × 0.22 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: none
16094 measured reflections
3646 independent reflections
2747 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.133
S = 1.08
3646 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C27—H27A⋯Cl1	0.97	2.68	3.075 (2)	105

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012117/xu2420sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012117/xu2420Isup2.hkl

checkCIF report

Comment top

Fluorene derivatives, have attracted much attention due to their potential utilities in organic lightemitting devices (Muller et al., 2003), organic phototransistors (Saragi et al., 2004), nonlinear optics (Kim et al., 1998) and photochromic materials (Chun et al., 2003). The title compound (hereinafter abbreviated to fmcf) is one of fluorene derivatives.

The asymmetric unit of the title compound contains one fmcf molecule (Fig. 1). The chloromethyl group is attached on the C-9 position of one fluorene ring. Two fluorene rings are linked together through a methylene carbon atom, and the dihedral angle between the two fluorene rings is 71.97 (4)°. There is intramolecular C–H···Cl hydrogen bond with distance of 3.075 (2) Å (Table 1), while the intermolecular C–H···Cl contacts are of 3.573 (2) Å, which is not viewed as C–H···Cl hydrogen bond. The centroid to centroid distance between stacked fluorene rings is ca. 4.22 Å, which is very long and prevents π···π stacking (Fig. 2). All bond lengths and angles are normal.

Related literature top

For general background, see: Chun et al. (2003); Kim et al. (1998); Muller et al. (2003); Saragi et al. (2004).

Experimental top

All chemicals were of analytic grade quality obtained from commercial sources and used as received, unless stated otherwise. To a solution of fluorene (1.66 g, 10 mmol) in dry THF (40 ml) was added a hexane solution of n-butylithium (4 ml, 2.5 M, 10 mmol) under nitrogen at -78 °C, the mixture was stirred for 1 h. A solution of PCl₃ (2 mmol) in THF (10 ml) was then added. After stirring for another 1 h, the mixture was cooling slowly to room temperature, and kept stirring overnight. To the mixture was added dichloromethane (20 ml) and stirred for 1 h. The solvent was evaporated under reduced pressure. The crude products were purified by columnchromatography (silica gel) using n-hexane/dichloromethane as eluent. The title compound was obtained as white solid in 31% yield. Colorless single crystals were grown from a CH₂Cl₂ solution of the compound.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2008).

Figures top

	Fig. 1. The molecular structure showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Partial packing view of the title compound. H atoms are omitted for clarity.

9-Chloromethyl-9-[(9H-fluoren-9-yl)methyl]-9H-fluorene top

Crystal data top

C₂₈H₂₁Cl	F(000) = 824
M_r = 392.90	D_x = 1.290 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12994 reflections
a = 8.4346 (17) Å	θ = 3.1–27.4°
b = 26.368 (5) Å	µ = 0.20 mm⁻¹
c = 9.1162 (18) Å	T = 298 K
β = 94.08 (3)°	Chunk, colorless
V = 2022.3 (7) Å³	0.35 × 0.29 × 0.22 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2747 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 25.3°, θ_min = 3.1°
ϕ and ω scans	h = −10→10
16094 measured reflections	k = −31→31
3646 independent reflections	l = −10→10

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)] = 0.040	H-atom parameters constrained
wR(F²) = 0.133	w = 1/[σ²(F_o²) + (0.0595P)² + 0.3188P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
3646 reflections	Δρ_max = 0.22 e Å⁻³
263 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (2)

Crystal data top

C₂₈H₂₁Cl	V = 2022.3 (7) Å³
M_r = 392.90	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4346 (17) Å	µ = 0.20 mm⁻¹
b = 26.368 (5) Å	T = 298 K
c = 9.1162 (18) Å	0.35 × 0.29 × 0.22 mm
β = 94.08 (3)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2747 reflections with I > 2σ(I)
16094 measured reflections	R_int = 0.025
3646 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.08	Δρ_max = 0.22 e Å⁻³
3646 reflections	Δρ_min = −0.26 e Å⁻³
263 parameters

Special details top

Experimental. ¹HNMR (500 MHz, δ in p.p.m., CDCl₃): 2.90 (d, 2H, J = 5.5 Hz), 3.19 (t, 1H,J= 4.5 Hz), 3.86 (s, 2H), 6.62 (d, 2H, J = 7.0 Hz), 7.02 (t, 2H, J= 7.5 Hz), 7.19 (t, 2H, J = 7.5 Hz), 7.39 (t, 2H, J = 7.5 Hz), 7.46 (t, 2H, J = 7.5 Hz), 7.54 (d, 2H,J = 7.5 Hz), 7.67 (d, 2H, J = 7.5 Hz), 7.78 (d, 2H, J= 7.0 Hz); ¹³C NMR (125 MHz, δ in p.p.m., CDCl₃): 40.64, 44.45, 53.35, 55.55, 119.52, 120.75, 125.06, 125.18, 126.86, 126.92, 127.66,128.74, 140.70, 141.48, 146.99, 148.22; MS (EI): calcd for C₂₈H₂₁Cl, 392; found: 392 (M⁺), 356, 191 (100), 179, 165, 152.

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
Cl1	0.14417 (6)	0.73515 (2)	0.46199 (7)	0.0815 (2)
C1	0.38752 (16)	0.68247 (6)	0.60052 (19)	0.0421 (4)
C2	0.30669 (16)	0.65243 (5)	0.72229 (18)	0.0407 (4)
C3	0.16272 (18)	0.63563 (7)	0.7173 (2)	0.0546 (5)
H3	0.0926	0.6402	0.6349	0.066*
C4	0.1160 (2)	0.60914 (7)	0.8475 (3)	0.0671 (6)
H4	0.0121	0.5971	0.8434	0.080*
C5	0.2094 (2)	0.59950 (7)	0.9791 (3)	0.0651 (5)
H5	0.1692	0.5821	1.0571	0.078*
C6	0.3524 (2)	0.61602 (7)	0.9853 (2)	0.0547 (5)
H6	0.4216	0.6113	1.0682	0.066*
C7	0.40065 (17)	0.64228 (5)	0.85735 (18)	0.0410 (4)
C8	0.54497 (17)	0.66472 (6)	0.83543 (19)	0.0427 (4)
C9	0.6747 (2)	0.66400 (7)	0.9329 (2)	0.0581 (5)
H9	0.6787	0.6472	1.0228	0.070*
C10	0.7950 (2)	0.69009 (8)	0.8846 (3)	0.0731 (7)
H10	0.8899	0.6913	0.9430	0.088*
C11	0.7859 (2)	0.71698 (9)	0.7450 (3)	0.0778 (7)
H11	0.8749	0.7353	0.7215	0.093*
C12	0.6578 (2)	0.71744 (7)	0.6465 (3)	0.0635 (5)
H12	0.6545	0.7349	0.5576	0.076*
C13	0.53712 (17)	0.69020 (6)	0.6907 (2)	0.0455 (4)
C14	0.47723 (18)	0.60085 (6)	0.46017 (19)	0.0461 (4)
H14	0.5053	0.5943	0.5646	0.055*
C15	0.38570 (18)	0.55633 (6)	0.39464 (19)	0.0460 (4)
C16	0.2451 (2)	0.54170 (7)	0.4245 (2)	0.0573 (5)
H16	0.1867	0.5592	0.4909	0.069*
C17	0.1854 (2)	0.49837 (7)	0.3523 (2)	0.0637 (5)
H17	0.0848	0.4874	0.3737	0.076*
C18	0.2642 (2)	0.47010 (7)	0.2507 (3)	0.0659 (5)
H18	0.2167	0.4416	0.2063	0.079*
C19	0.4057 (2)	0.48432 (7)	0.2191 (2)	0.0593 (5)
H19	0.4628	0.4668	0.1516	0.071*
C20	0.46626 (18)	0.52716 (6)	0.29204 (19)	0.0473 (4)
C21	0.61091 (18)	0.55048 (7)	0.28235 (19)	0.0497 (4)
C22	0.7292 (2)	0.53544 (8)	0.1985 (2)	0.0626 (5)
H22	0.7211	0.5070	0.1383	0.075*
C23	0.8541 (2)	0.56413 (10)	0.2096 (3)	0.0737 (6)
H23	0.9398	0.5561	0.1552	0.088*
C24	0.8643 (2)	0.60722 (9)	0.3016 (3)	0.0766 (6)
H24	0.9573	0.6262	0.3044	0.092*
C25	0.7467 (2)	0.62294 (9)	0.3868 (2)	0.0666 (6)
H25	0.7561	0.6515	0.4466	0.080*
C26	0.61912 (18)	0.59411 (7)	0.37704 (19)	0.0501 (4)
C27	0.40233 (18)	0.65354 (6)	0.44306 (19)	0.0472 (4)
H27A	0.2972	0.6503	0.3934	0.057*
H27B	0.4661	0.6741	0.3816	0.057*
C28	0.3207 (2)	0.73528 (7)	0.5688 (2)	0.0576 (5)
H28A	0.3983	0.7549	0.5193	0.069*
H28B	0.3045	0.7520	0.6613	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0610 (3)	0.0870 (4)	0.0956 (5)	0.0332 (3)	−0.0002 (3)	0.0213 (3)
C1	0.0348 (7)	0.0412 (8)	0.0506 (10)	0.0036 (6)	0.0054 (7)	0.0058 (7)
C2	0.0311 (7)	0.0375 (8)	0.0540 (10)	0.0019 (6)	0.0063 (7)	−0.0014 (7)
C3	0.0342 (8)	0.0576 (10)	0.0720 (13)	−0.0010 (7)	0.0043 (8)	−0.0049 (9)
C4	0.0415 (9)	0.0611 (11)	0.1018 (17)	−0.0098 (8)	0.0271 (10)	−0.0070 (11)
C5	0.0605 (11)	0.0605 (11)	0.0774 (15)	−0.0026 (9)	0.0271 (10)	0.0139 (10)
C6	0.0519 (10)	0.0536 (10)	0.0593 (12)	0.0054 (8)	0.0092 (8)	0.0090 (9)
C7	0.0390 (8)	0.0344 (7)	0.0503 (10)	0.0048 (6)	0.0075 (7)	0.0000 (7)
C8	0.0333 (7)	0.0382 (8)	0.0563 (11)	0.0045 (6)	0.0020 (7)	−0.0065 (7)
C9	0.0454 (9)	0.0554 (10)	0.0720 (13)	0.0096 (8)	−0.0072 (9)	−0.0139 (9)
C10	0.0352 (9)	0.0727 (13)	0.1100 (19)	0.0001 (9)	−0.0045 (10)	−0.0327 (13)
C11	0.0392 (9)	0.0748 (13)	0.121 (2)	−0.0183 (9)	0.0167 (11)	−0.0319 (14)
C12	0.0499 (10)	0.0556 (10)	0.0871 (15)	−0.0133 (8)	0.0188 (10)	−0.0032 (10)
C13	0.0351 (7)	0.0404 (8)	0.0616 (11)	−0.0011 (6)	0.0087 (7)	−0.0031 (8)
C14	0.0401 (8)	0.0526 (9)	0.0453 (10)	0.0095 (7)	0.0015 (7)	0.0017 (7)
C15	0.0412 (8)	0.0476 (9)	0.0488 (10)	0.0104 (7)	0.0018 (7)	0.0071 (7)
C16	0.0467 (9)	0.0584 (10)	0.0678 (13)	0.0059 (8)	0.0118 (8)	0.0026 (9)
C17	0.0487 (10)	0.0574 (11)	0.0854 (15)	−0.0004 (8)	0.0075 (10)	0.0087 (11)
C18	0.0600 (11)	0.0501 (10)	0.0869 (15)	0.0005 (9)	0.0005 (10)	−0.0018 (10)
C19	0.0562 (10)	0.0511 (10)	0.0705 (13)	0.0136 (8)	0.0047 (9)	−0.0029 (9)
C20	0.0426 (8)	0.0471 (9)	0.0519 (11)	0.0125 (7)	0.0002 (7)	0.0067 (8)
C21	0.0418 (8)	0.0574 (10)	0.0496 (10)	0.0171 (7)	0.0013 (7)	0.0059 (8)
C22	0.0470 (10)	0.0744 (12)	0.0663 (13)	0.0196 (9)	0.0045 (9)	−0.0018 (10)
C23	0.0406 (10)	0.1029 (17)	0.0786 (15)	0.0206 (10)	0.0110 (9)	0.0027 (13)
C24	0.0348 (9)	0.1053 (17)	0.0897 (17)	0.0044 (10)	0.0036 (10)	−0.0003 (14)
C25	0.0412 (9)	0.0843 (14)	0.0737 (14)	0.0025 (9)	−0.0006 (9)	−0.0097 (11)
C26	0.0349 (8)	0.0629 (10)	0.0515 (11)	0.0120 (7)	−0.0029 (7)	0.0022 (8)
C27	0.0383 (8)	0.0532 (9)	0.0499 (10)	0.0097 (7)	0.0024 (7)	0.0078 (8)
C28	0.0527 (10)	0.0496 (10)	0.0714 (13)	0.0093 (8)	0.0104 (9)	0.0101 (9)

Geometric parameters (Å, º) top

Cl1—C28	1.720 (2)	C14—C27	1.530 (2)
C1—C13	1.470 (2)	C14—H14	0.9800
C1—C28	1.522 (2)	C15—C16	1.294 (2)
C1—C2	1.560 (2)	C15—C20	1.421 (2)
C1—C27	1.638 (2)	C16—C17	1.395 (3)
C2—C3	1.290 (2)	C16—H16	0.9300
C2—C7	1.441 (2)	C17—C18	1.394 (3)
C3—C4	1.455 (3)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.302 (3)
C4—C5	1.411 (3)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.390 (3)
C5—C6	1.280 (3)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.375 (2)
C6—C7	1.440 (2)	C21—C22	1.358 (2)
C6—H6	0.9300	C21—C26	1.437 (3)
C7—C8	1.381 (2)	C22—C23	1.295 (3)
C8—C9	1.360 (2)	C22—H22	0.9300
C8—C13	1.478 (2)	C23—C24	1.411 (3)
C9—C10	1.326 (3)	C23—H23	0.9300
C9—H9	0.9300	C24—C25	1.367 (3)
C10—C11	1.454 (4)	C24—H24	0.9300
C10—H10	0.9300	C25—C26	1.315 (3)
C11—C12	1.355 (3)	C25—H25	0.9300
C11—H11	0.9300	C27—H27A	0.9700
C12—C13	1.331 (2)	C27—H27B	0.9700
C12—H12	0.9300	C28—H28A	0.9700
C14—C26	1.472 (2)	C28—H28B	0.9700
C14—C15	1.505 (2)

C13—C1—C28	105.72 (13)	C16—C15—C20	117.73 (17)
C13—C1—C2	94.22 (12)	C16—C15—C14	126.93 (17)
C28—C1—C2	115.17 (13)	C20—C15—C14	115.32 (14)
C13—C1—C27	116.01 (12)	C15—C16—C17	116.78 (18)
C28—C1—C27	108.04 (14)	C15—C16—H16	121.6
C2—C1—C27	116.85 (12)	C17—C16—H16	121.6
C3—C2—C7	115.17 (16)	C18—C17—C16	125.34 (18)
C3—C2—C1	127.39 (16)	C18—C17—H17	117.3
C7—C2—C1	117.44 (13)	C16—C17—H17	117.3
C2—C3—C4	116.40 (17)	C19—C18—C17	118.73 (19)
C2—C3—H3	121.8	C19—C18—H18	120.6
C4—C3—H3	121.8	C17—C18—H18	120.6
C5—C4—C3	127.81 (16)	C18—C19—C20	116.08 (18)
C5—C4—H4	116.1	C18—C19—H19	122.0
C3—C4—H4	116.1	C20—C19—H19	122.0
C6—C5—C4	116.31 (19)	C21—C20—C19	129.09 (16)
C6—C5—H5	121.8	C21—C20—C15	105.57 (15)
C4—C5—H5	121.8	C19—C20—C15	125.33 (16)
C5—C6—C7	116.61 (19)	C22—C21—C20	126.61 (18)
C5—C6—H6	121.7	C22—C21—C26	124.45 (17)
C7—C6—H6	121.7	C20—C21—C26	108.94 (15)
C8—C7—C6	128.77 (16)	C23—C22—C21	114.3 (2)
C8—C7—C2	103.51 (14)	C23—C22—H22	122.8
C6—C7—C2	127.70 (15)	C21—C22—H22	122.8
C9—C8—C7	125.19 (17)	C22—C23—C24	122.10 (19)
C9—C8—C13	124.93 (16)	C22—C23—H23	118.9
C7—C8—C13	109.88 (14)	C24—C23—H23	118.9
C10—C9—C8	112.0 (2)	C25—C24—C23	124.5 (2)
C10—C9—H9	124.0	C25—C24—H24	117.8
C8—C9—H9	124.0	C23—C24—H24	117.8
C9—C10—C11	123.34 (18)	C26—C25—C24	114.1 (2)
C9—C10—H10	118.3	C26—C25—H25	122.9
C11—C10—H10	118.3	C24—C25—H25	122.9
C12—C11—C10	125.04 (19)	C25—C26—C21	120.52 (17)
C12—C11—H11	117.5	C25—C26—C14	125.89 (18)
C10—C11—H11	117.5	C21—C26—C14	113.56 (15)
C13—C12—C11	112.7 (2)	C14—C27—C1	112.98 (13)
C13—C12—H12	123.7	C14—C27—H27A	109.0
C11—C12—H12	123.7	C1—C27—H27A	109.0
C12—C13—C1	123.32 (17)	C14—C27—H27B	109.0
C12—C13—C8	121.94 (17)	C1—C27—H27B	109.0
C1—C13—C8	114.73 (13)	H27A—C27—H27B	107.8
C26—C14—C15	96.56 (14)	C1—C28—Cl1	113.56 (13)
C26—C14—C27	113.72 (15)	C1—C28—H28A	108.9
C15—C14—C27	118.13 (13)	Cl1—C28—H28A	108.9
C26—C14—H14	109.2	C1—C28—H28B	108.9
C15—C14—H14	109.2	Cl1—C28—H28B	108.9
C27—C14—H14	109.2	H28A—C28—H28B	107.7

C13—C1—C2—C3	176.17 (17)	C26—C14—C15—C20	1.81 (17)
C28—C1—C2—C3	66.6 (2)	C27—C14—C15—C20	123.19 (16)
C27—C1—C2—C3	−61.8 (2)	C20—C15—C16—C17	−0.1 (3)
C13—C1—C2—C7	−3.14 (16)	C14—C15—C16—C17	−178.46 (16)
C28—C1—C2—C7	−112.70 (16)	C15—C16—C17—C18	−0.5 (3)
C27—C1—C2—C7	118.88 (14)	C16—C17—C18—C19	0.4 (3)
C7—C2—C3—C4	0.1 (2)	C17—C18—C19—C20	0.4 (3)
C1—C2—C3—C4	−179.23 (15)	C18—C19—C20—C21	179.31 (19)
C2—C3—C4—C5	−0.1 (3)	C18—C19—C20—C15	−1.0 (3)
C3—C4—C5—C6	0.1 (3)	C16—C15—C20—C21	−179.38 (16)
C4—C5—C6—C7	−0.1 (3)	C14—C15—C20—C21	−0.83 (19)
C5—C6—C7—C8	178.42 (17)	C16—C15—C20—C19	0.9 (3)
C5—C6—C7—C2	0.2 (3)	C14—C15—C20—C19	179.43 (16)
C3—C2—C7—C8	−178.76 (14)	C19—C20—C21—C22	−1.2 (3)
C1—C2—C7—C8	0.64 (17)	C15—C20—C21—C22	179.06 (17)
C3—C2—C7—C6	−0.2 (2)	C19—C20—C21—C26	179.09 (17)
C1—C2—C7—C6	179.23 (15)	C15—C20—C21—C26	−0.64 (18)
C6—C7—C8—C9	3.1 (3)	C20—C21—C22—C23	−179.87 (19)
C2—C7—C8—C9	−178.30 (15)	C26—C21—C22—C23	−0.2 (3)
C6—C7—C8—C13	−176.25 (15)	C21—C22—C23—C24	0.0 (3)
C2—C7—C8—C13	2.33 (16)	C22—C23—C24—C25	0.1 (4)
C7—C8—C9—C10	−177.88 (16)	C23—C24—C25—C26	0.1 (3)
C13—C8—C9—C10	1.4 (2)	C24—C25—C26—C21	−0.3 (3)
C8—C9—C10—C11	1.2 (3)	C24—C25—C26—C14	177.61 (17)
C9—C10—C11—C12	−2.2 (3)	C22—C21—C26—C25	0.4 (3)
C10—C11—C12—C13	0.1 (3)	C20—C21—C26—C25	−179.91 (18)
C11—C12—C13—C1	−176.77 (16)	C22—C21—C26—C14	−177.76 (16)
C11—C12—C13—C8	2.5 (3)	C20—C21—C26—C14	2.0 (2)
C28—C1—C13—C12	−58.6 (2)	C15—C14—C26—C25	179.82 (19)
C2—C1—C13—C12	−176.21 (16)	C27—C14—C26—C25	55.1 (3)
C27—C1—C13—C12	61.1 (2)	C15—C14—C26—C21	−2.17 (17)
C28—C1—C13—C8	122.11 (15)	C27—C14—C26—C21	−126.84 (16)
C2—C1—C13—C8	4.48 (15)	C26—C14—C27—C1	−123.54 (15)
C27—C1—C13—C8	−118.20 (15)	C15—C14—C27—C1	124.34 (16)
C9—C8—C13—C12	−3.6 (3)	C13—C1—C27—C14	58.35 (18)
C7—C8—C13—C12	175.79 (16)	C28—C1—C27—C14	176.78 (13)
C9—C8—C13—C1	175.74 (15)	C2—C1—C27—C14	−51.45 (17)
C7—C8—C13—C1	−4.88 (18)	C13—C1—C28—Cl1	179.50 (12)
C26—C14—C15—C16	−179.80 (18)	C2—C1—C28—Cl1	−77.98 (18)
C27—C14—C15—C16	−58.4 (2)	C27—C1—C28—Cl1	54.69 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27A···Cl1	0.97	2.68	3.075 (2)	105
C10—H10···Cl1ⁱ	0.93	2.89	3.573 (2)	131

Symmetry code: (i) x+1, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₁Cl
M_r	392.90
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.4346 (17), 26.368 (5), 9.1162 (18)
β (°)	94.08 (3)
V (Å³)	2022.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.35 × 0.29 × 0.22

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16094, 3646, 2747
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.133, 1.08
No. of reflections	3646
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.26

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27A···Cl1	0.97	2.68	3.075 (2)	104.9

Acknowledgements

The authors thank the National Natural Science Foundation of China (20674070) and the Natural Science Foundation of Zhejiang Province, China (R404109).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chun, C., Kim, M.-J., Vak, D. & Kim, D. Y. (2003). J. Mater. Chem. 13, 2904–2909. Web of Science CrossRef CAS Google Scholar
Kim, S. Y., Lee, M. & Boo, B. H. (1998). J. Chem. Phys. 109, 2593–2595. Web of Science CrossRef CAS Google Scholar
Muller, C. D., Falcou, A., Reckefuss, N., Rojahn, M., Wiederhirn, V., Rudati, P., Frohne, H., Nuyken, O., Becker, H. & Meerholz, K. (2003). Nature (London), 421, 829–833. Web of Science CrossRef PubMed Google Scholar
Saragi, T. P. I., Pudzich, R., Fuhrmann, T. & Salbeck, J. (2004). Appl. Phys. Lett. 84, 2334–2336. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar