2',7'-Di-bromo-spiro-[cyclo-propane-1,9'-fluorene].

In the title compound, C15H10Br2, each mol-ecule is situated on special postion mm, so the asymmetric unit contains one-quater of a mol-ecule. The 2,7-di-bromo-9H-fluorene fragment and three spiro-cyclo-propane C atoms lie on different planes, which are perpendicular to each other. In the crystal, π-π inter-actions between aromatic rings [inter-centroid distance = 3.699 (3) Å] pack the mol-ecules into stacks extending in [001].

Related literature

For electroluminescence properties of fluorene derivatives, see: Cho et al. (2007 ▶); Jiang et al. (2005 ▶); Wei et al. (2008 ▶). For the crystal structures of related compounds, see: Jason et al. (1981 ▶); Wang et al. (2007 ▶).

Experimental

Crystal data

C15H10Br2

M = 350.05

Orthorhombic,

a = 16.9485 (17) Å

b = 11.0619 (11) Å

c = 6.8127 (10) Å

V = 1277.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 6.32 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

3276 measured reflections

640 independent reflections

471 reflections with I > 2σ(I)

R int = 0.155

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.100

S = 0.98

640 reflections

53 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.68 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814014585/cv5463sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014585/cv5463Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814014585/cv5463Isup3.cml

CCDC reference: 1009321

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H10Br2	Dx = 1.820 Mg m−3
Mr = 350.05	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Cmcm	Cell parameters from 933 reflections
a = 16.9485 (17) Å	θ = 2.2–25.0°
b = 11.0619 (11) Å	µ = 6.32 mm−1
c = 6.8127 (10) Å	T = 293 K
V = 1277.3 (3) Å3	Block, colourless
Z = 4	0.30 × 0.20 × 0.20 mm
F(000) = 680

Bruker SMART CCD area-detector diffractometer	Rint = 0.155
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.2°
phi and ω scans	h = −20→17
3276 measured reflections	k = −13→12
640 independent reflections	l = −8→7
471 reflections with I > 2σ(I)

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0438P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
640 reflections	Δρmax = 0.30 e Å−3
53 parameters	Δρmin = −0.68 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.

	x	y	z	Uiso*/Ueq
Br1	0.31110 (3)	0.12115 (5)	0.7500	0.0746 (4)
C1	0.0691 (3)	0.1592 (4)	0.7500	0.0396 (11)
C2	0.1489 (3)	0.1851 (4)	0.7500	0.0470 (12)
H2	0.1666	0.2647	0.7500	0.056*
C3	0.2011 (3)	0.0894 (5)	0.7500	0.0478 (12)
C4	0.1763 (3)	−0.0277 (4)	0.7500	0.0506 (12)
H4	0.2130	−0.0901	0.7500	0.061*
C5	0.0965 (3)	−0.0541 (4)	0.7500	0.0450 (12)
H5	0.0792	−0.1339	0.7500	0.054*
C6	0.0429 (2)	0.0393 (4)	0.7500	0.0380 (10)
C13	0.0000	0.2412 (5)	0.7500	0.0424 (16)
C14	0.0000	0.3609 (3)	0.6418 (11)	0.0725 (18)
H14	0.0485	0.3846	0.5754	0.087*

	U11	U22	U33	U12	U13	U23
Br1	0.0506 (4)	0.0657 (5)	0.1074 (6)	0.0008 (3)	0.000	0.000
C1	0.054 (3)	0.0309 (19)	0.034 (2)	−0.001 (2)	0.000	0.000
C2	0.056 (3)	0.034 (2)	0.051 (3)	−0.004 (2)	0.000	0.000
C3	0.047 (3)	0.049 (3)	0.047 (3)	0.005 (2)	0.000	0.000
C4	0.059 (3)	0.046 (3)	0.047 (3)	0.012 (2)	0.000	0.000
C5	0.063 (3)	0.031 (2)	0.041 (3)	0.003 (2)	0.000	0.000
C6	0.052 (2)	0.032 (2)	0.031 (2)	0.0006 (19)	0.000	0.000
C13	0.051 (4)	0.028 (3)	0.048 (4)	0.000	0.000	0.000
C14	0.054 (3)	0.039 (3)	0.125 (5)	0.000	0.000	0.030 (3)

Br1—C3	1.897 (5)	C5—C6	1.375 (6)
C1—C2	1.383 (6)	C5—H5	0.9299
C1—C6	1.398 (6)	C6—C6i	1.454 (8)
C1—C13	1.481 (6)	C13—C1i	1.481 (6)
C2—C3	1.380 (7)	C13—C14	1.516 (7)
C2—H2	0.9300	C13—C14ii	1.516 (7)
C3—C4	1.361 (7)	C14—C14ii	1.475 (14)
C4—C5	1.384 (6)	C14—H14	0.9741
C4—H4	0.9299
C2—C1—C6	120.5 (4)	C4—C5—H5	120.5
C2—C1—C13	130.3 (4)	C5—C6—C1	120.2 (4)
C6—C1—C13	109.3 (4)	C5—C6—C6i	131.3 (3)
C3—C2—C1	117.9 (4)	C1—C6—C6i	108.5 (3)
C3—C2—H2	121.3	C1i—C13—C1	104.5 (5)
C1—C2—H2	120.8	C1i—C13—C14	122.36 (19)
C4—C3—C2	122.1 (5)	C1—C13—C14	122.36 (19)
C4—C3—Br1	118.7 (4)	C1i—C13—C14ii	122.36 (19)
C2—C3—Br1	119.2 (4)	C1—C13—C14ii	122.36 (19)
C3—C4—C5	120.2 (4)	C14—C13—C14ii	58.2 (6)
C3—C4—H4	120.0	C14ii—C14—C13	60.9 (3)
C5—C4—H4	119.8	C14ii—C14—H14	117.6
C6—C5—C4	119.1 (4)	C13—C14—H14	117.4
C6—C5—H5	120.4
C6—C1—C2—C3	0.0	C2—C1—C6—C6i	180.0
C13—C1—C2—C3	180.0	C13—C1—C6—C6i	0.0
C1—C2—C3—C4	0.0	C2—C1—C13—C1i	180.0
C1—C2—C3—Br1	180.0	C6—C1—C13—C1i	0.0
C2—C3—C4—C5	0.0	C2—C1—C13—C14	35.1 (4)
Br1—C3—C4—C5	180.0	C6—C1—C13—C14	−144.9 (4)
C3—C4—C5—C6	0.0	C2—C1—C13—C14ii	−35.1 (4)
C4—C5—C6—C1	0.0	C6—C1—C13—C14ii	144.9 (4)
C4—C5—C6—C6i	180.0	C1i—C13—C14—C14ii	110.6 (3)
C2—C1—C6—C5	0.0	C1—C13—C14—C14ii	−110.6 (3)
C13—C1—C6—C5	180.0