4,4,5,5-Tetra-methyl-2-[1,3,6,8-tetra-bromo-7-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)pyren-2-yl]-1,3,2-dioxaborolane.

The complete mol-ecule of the title compound, C(28)H(28)B(2)Br(4)O(4), is generated by the application of a centre of inversion. In the mol-ecule, the BO(2) plane is perpendicular to that through the pyrene ring [dihedral angle = 86.27 (13)°]. In the crystal, mol-ecules stack into columns along the b axis, the closest contact between these being of the type C-Br⋯π.

Related literature

For background to the reactions of pyrene, see: Miura & Yamano (1995 ▶). For the structure of the non-brominated derivative, see: Coventry et al. (2005 ▶).

Experimental

Crystal data

C28H28B2Br4O4

M = 769.76

Monoclinic,

a = 15.5047 (10) Å

b = 7.5136 (5) Å

c = 13.9191 (9) Å

β = 113.961 (1)°

V = 1481.78 (17) Å3

Z = 2

Mo Kα radiation

μ = 5.46 mm−1

T = 296 K

0.34 × 0.24 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.258, T max = 0.475

8745 measured reflections

3344 independent reflections

2488 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.109

S = 1.01

3344 reflections

176 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.67 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX-2 (Dolomanov et al., 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812006095/tk5049sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006095/tk5049Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006095/tk5049Isup3.cml

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

C28H28B2Br4O4	F(000) = 756
Mr = 769.76	Dx = 1.725 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3344 reflections
a = 15.5047 (10) Å	θ = 2.9–27.4°
b = 7.5136 (5) Å	µ = 5.46 mm−1
c = 13.9191 (9) Å	T = 296 K
β = 113.961 (1)°	Pod, colourless
V = 1481.78 (17) Å3	0.34 × 0.24 × 0.16 mm
Z = 2

Bruker APEXII CCD diffractometer	3344 independent reflections
Radiation source: fine-focus sealed tube	2488 reflections with i > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→18
Tmin = 0.258, Tmax = 0.475	k = −9→9
8745 measured reflections	l = −9→18

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0653P)2 + 0.4343P] where P = (Fo2 + 2Fc2)/3
3344 reflections	(Δ/σ)max = 0.007
176 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.67 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.

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.

	x	y	z	Uiso*/Ueq
Br1	0.77662 (3)	0.70726 (6)	0.97202 (4)	0.07199 (18)
Br2	0.58141 (3)	0.07842 (5)	0.79828 (3)	0.06680 (17)
O1	0.73711 (17)	0.4128 (3)	0.75325 (18)	0.0521 (6)
O2	0.81831 (17)	0.2540 (4)	0.89972 (18)	0.0603 (7)
C1	0.8075 (4)	0.3192 (8)	0.6352 (3)	0.0949 (17)
H1A	0.7619	0.2248	0.6114	0.142*
H1B	0.8652	0.2812	0.6316	0.142*
H1C	0.7835	0.4218	0.5914	0.142*
C2	0.8258 (2)	0.3653 (5)	0.7461 (3)	0.0537 (9)
C3	0.6666 (2)	0.4017 (4)	0.8923 (2)	0.0380 (6)
C4	0.5917 (2)	0.2876 (4)	0.8788 (2)	0.0395 (7)
C5	0.5247 (2)	0.3199 (4)	0.9201 (2)	0.0377 (6)
C6	0.4480 (2)	0.2033 (4)	0.9060 (3)	0.0503 (8)
H6	0.4417	0.0985	0.8681	0.060*
C7	0.3844 (2)	0.2413 (5)	0.9460 (3)	0.0522 (9)
H7	0.3348	0.1628	0.9345	0.063*
C8	0.6087 (2)	0.6003 (4)	0.9941 (2)	0.0404 (7)
C9	0.6728 (2)	0.5543 (4)	0.9499 (3)	0.0424 (7)
C10	0.8662 (3)	0.2212 (5)	0.8302 (3)	0.0588 (10)
C11	0.8343 (5)	0.0358 (6)	0.7828 (6)	0.119 (2)
H11A	0.8451	−0.0486	0.8382	0.178*
H11B	0.8697	0.0015	0.7429	0.178*
H11C	0.7683	0.0387	0.7375	0.178*
C12	0.8844 (4)	0.5382 (7)	0.7748 (5)	0.0971 (17)
H12A	0.8460	0.6359	0.7364	0.146*
H12B	0.9378	0.5261	0.7571	0.146*
H12C	0.9059	0.5600	0.8489	0.146*
C13	0.9711 (3)	0.2251 (10)	0.8940 (4)	0.113 (2)
H13A	0.9882	0.3348	0.9325	0.169*
H13B	1.0032	0.2160	0.8479	0.169*
H13C	0.9889	0.1269	0.9423	0.169*
C14	0.53370 (18)	0.4799 (4)	0.9788 (2)	0.0340 (6)
B1	0.7425 (2)	0.3542 (5)	0.8473 (3)	0.0397 (7)

	U11	U22	U33	U12	U13	U23
Br1	0.0592 (3)	0.0748 (3)	0.1085 (4)	−0.02956 (19)	0.0614 (3)	−0.0371 (2)
Br2	0.0623 (3)	0.0677 (3)	0.0883 (3)	−0.01639 (18)	0.0490 (2)	−0.0388 (2)
O1	0.0482 (13)	0.0696 (15)	0.0472 (13)	0.0173 (11)	0.0281 (11)	0.0108 (11)
O2	0.0525 (14)	0.0954 (19)	0.0458 (13)	0.0283 (13)	0.0331 (12)	0.0213 (13)
C1	0.124 (4)	0.122 (4)	0.058 (3)	0.044 (4)	0.056 (3)	0.016 (3)
C2	0.053 (2)	0.070 (2)	0.0533 (19)	0.0117 (17)	0.0365 (17)	0.0064 (17)
C3	0.0304 (14)	0.0502 (17)	0.0361 (15)	0.0019 (12)	0.0164 (12)	−0.0025 (13)
C4	0.0353 (15)	0.0459 (16)	0.0396 (15)	0.0015 (12)	0.0175 (13)	−0.0087 (13)
C5	0.0303 (14)	0.0468 (16)	0.0389 (15)	−0.0028 (12)	0.0171 (13)	−0.0058 (13)
C6	0.0470 (18)	0.0480 (19)	0.066 (2)	−0.0136 (14)	0.0337 (17)	−0.0207 (16)
C7	0.0449 (18)	0.0520 (19)	0.072 (2)	−0.0169 (15)	0.0358 (18)	−0.0202 (17)
C8	0.0342 (15)	0.0481 (17)	0.0442 (16)	−0.0061 (13)	0.0213 (13)	−0.0086 (13)
C9	0.0312 (15)	0.0519 (18)	0.0493 (18)	−0.0071 (13)	0.0218 (14)	−0.0045 (14)
C10	0.054 (2)	0.073 (2)	0.070 (2)	0.0207 (18)	0.0466 (19)	0.0189 (19)
C11	0.192 (7)	0.055 (3)	0.183 (6)	0.007 (3)	0.153 (6)	0.004 (3)
C12	0.103 (4)	0.078 (3)	0.144 (5)	−0.016 (3)	0.086 (4)	−0.003 (3)
C13	0.057 (3)	0.197 (7)	0.090 (4)	0.045 (4)	0.035 (3)	0.029 (4)
C14	0.0288 (13)	0.0408 (15)	0.0354 (15)	−0.0024 (11)	0.0162 (12)	−0.0050 (12)
B1	0.0338 (17)	0.0473 (19)	0.0427 (19)	0.0011 (14)	0.0204 (15)	−0.0029 (15)

Br1—C9	1.899 (3)	C6—H6	0.9300
Br2—C4	1.899 (3)	C7—C8i	1.432 (4)
O1—B1	1.351 (4)	C7—H7	0.9300
O1—C2	1.463 (4)	C8—C9	1.408 (4)
O2—B1	1.336 (4)	C8—C14	1.419 (4)
O2—C10	1.460 (4)	C8—C7i	1.432 (4)
C1—C2	1.492 (5)	C10—C13	1.504 (6)
C1—H1A	0.9600	C10—C11	1.535 (7)
C1—H1B	0.9600	C11—H11A	0.9600
C1—H1C	0.9600	C11—H11B	0.9600
C2—C10	1.530 (5)	C11—H11C	0.9600
C2—C12	1.542 (6)	C12—H12A	0.9600
C3—C9	1.380 (4)	C12—H12B	0.9600
C3—C4	1.394 (4)	C12—H12C	0.9600
C3—B1	1.583 (4)	C13—H13A	0.9600
C4—C5	1.397 (4)	C13—H13B	0.9600
C5—C6	1.425 (4)	C13—H13C	0.9600
C5—C14	1.428 (4)	C14—C14i	1.426 (5)
C6—C7	1.345 (4)
B1—O1—C2	107.2 (3)	C3—C9—Br1	116.9 (2)
B1—O2—C10	107.7 (2)	C8—C9—Br1	118.9 (2)
C2—C1—H1A	109.5	O2—C10—C13	109.0 (3)
C2—C1—H1B	109.5	O2—C10—C2	103.1 (2)
H1A—C1—H1B	109.5	C13—C10—C2	116.5 (4)
C2—C1—H1C	109.5	O2—C10—C11	106.1 (3)
H1A—C1—H1C	109.5	C13—C10—C11	110.7 (5)
H1B—C1—H1C	109.5	C2—C10—C11	110.7 (4)
O1—C2—C1	109.7 (3)	C10—C11—H11A	109.5
O1—C2—C10	103.0 (2)	C10—C11—H11B	109.5
C1—C2—C10	118.3 (4)	H11A—C11—H11B	109.5
O1—C2—C12	104.4 (3)	C10—C11—H11C	109.5
C1—C2—C12	108.0 (4)	H11A—C11—H11C	109.5
C10—C2—C12	112.5 (4)	H11B—C11—H11C	109.5
C9—C3—C4	116.6 (3)	C2—C12—H12A	109.5
C9—C3—B1	122.0 (3)	C2—C12—H12B	109.5
C4—C3—B1	121.4 (3)	H12A—C12—H12B	109.5
C3—C4—C5	123.7 (3)	C2—C12—H12C	109.5
C3—C4—Br2	117.0 (2)	H12A—C12—H12C	109.5
C5—C4—Br2	119.2 (2)	H12B—C12—H12C	109.5
C4—C5—C6	123.7 (3)	C10—C13—H13A	109.5
C4—C5—C14	117.7 (2)	C10—C13—H13B	109.5
C6—C5—C14	118.6 (2)	H13A—C13—H13B	109.5
C7—C6—C5	121.6 (3)	C10—C13—H13C	109.5
C7—C6—H6	119.2	H13A—C13—H13C	109.5
C5—C6—H6	119.2	H13B—C13—H13C	109.5
C6—C7—C8i	121.6 (3)	C8—C14—C14i	119.8 (3)
C6—C7—H7	119.2	C8—C14—C5	120.4 (2)
C8i—C7—H7	119.2	C14i—C14—C5	119.8 (3)
C9—C8—C14	117.3 (3)	O2—B1—O1	114.1 (3)
C9—C8—C7i	124.0 (3)	O2—B1—C3	122.8 (3)
C14—C8—C7i	118.6 (3)	O1—B1—C3	123.1 (3)
C3—C9—C8	124.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—Br2···Cg1ii	1.90 (1)	3.48 (1)	4.921 (3)	130 (1)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3–C5/C8/C9/C14 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—Br2⋯Cg1i	1.90 (1)	3.48 (1)	4.921 (3)	130 (1)

Symmetry code: (i) .