9-Chloro-methyl-9-[(9H-fluoren-9-yl)meth-yl]-9H-fluorene.

In the title compound, C(28)H(21)Cl, the dihedral angle between the two fluorene ring systems is 71.97 (4)°. There is an intra-molecular 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 inter-actions 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 = 392.90

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.133

S = 1.08

3646 reflections

263 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.26 e Å−3

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 ▶).

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

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

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

C28H21Cl	F000 = 824
Mr = 392.90	Dx = 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 = 3.1–27.4º
b = 26.368 (5) Å	µ = 0.20 mm−1
c = 9.1162 (18) Å	T = 298 (2) K
β = 94.08 (3)º	Chunk, colorless
V = 2022.3 (7) Å3	0.35 × 0.29 × 0.22 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	2747 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Monochromator: graphite	θmax = 25.3º
T = 298(2) K	θmin = 3.1º
φ and ω scans	h = −10→10
Absorption correction: none	k = −31→31
16094 measured reflections	l = −10→10
3646 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040	w = 1/[σ2(Fo2) + (0.0595P)2 + 0.3188P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.133	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.22 e Å−3
3646 reflections	Δρmin = −0.25 e Å−3
263 parameters	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)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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