Di-μ-bromido-bis-[(diethyl ether-κO)(2,4,6-tri-methyl-phen-yl)magnesium]: the mesityl Grignard reagent.

The crystal structure of the title compound, [Mg2Br2(C9H11)2(C4H10O)2], features a centrosymmetric two-centre magnesium complex with half a mol-ecule in the asymmetric unit. The Mg atom is in a considerably distorted Br2CO coordination. Bond lengths and angles are comparable with already published values. The crystal packing is stabilized by C-H⋯π inter-actions linking the complexes into sheets parallel to (0-11).

Related literature

For literature on other Grignard reagents, see: Blasberg et al. (2012 ▶); Bock et al. (1996 ▶); Cole et al. (2003 ▶); Ellison & Power (1996 ▶); Hübner et al. (2010 ▶); Hayashi et al. (2011 ▶); Sakamoto et al. (2001 ▶); Waggoner & Power (1992 ▶).

Experimental

Crystal data

[Mg2Br2(C9H11)2(C4H10O)2]

M = 595.03

Triclinic,

a = 7.8516 (6) Å

b = 8.8285 (6) Å

c = 12.1356 (8) Å

α = 87.285 (6)°

β = 82.516 (6)°

γ = 65.396 (5)°

V = 758.30 (10) Å3

Z = 1

Mo Kα radiation

μ = 2.73 mm−1

T = 173 K

0.23 × 0.19 × 0.13 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001 ▶) T min = 0.572, T max = 0.718

18010 measured reflections

4227 independent reflections

3839 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.06

4227 reflections

148 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.55 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2012 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813017108/ng5334sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017108/ng5334Isup2.hkl

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

[Mg2Br2(C9H11)2(C4H10O)2]	Z = 1
Mr = 595.03	F(000) = 308
Triclinic, P1	Dx = 1.303 Mg m−3
a = 7.8516 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8285 (6) Å	Cell parameters from 29361 reflections
c = 12.1356 (8) Å	θ = 3.4–30.1°
α = 87.285 (6)°	µ = 2.73 mm−1
β = 82.516 (6)°	T = 173 K
γ = 65.396 (5)°	Plate, colourless
V = 758.30 (10) Å3	0.23 × 0.19 × 0.13 mm

Stoe IPDS II two-circle diffractometer	3839 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.048
ω scans	θmax = 29.7°, θmin = 3.2°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −10→10
Tmin = 0.572, Tmax = 0.718	k = −12→12
18010 measured reflections	l = −16→14
4227 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0555P)2 + 0.1885P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
4227 reflections	Δρmax = 0.70 e Å−3
148 parameters	Δρmin = −0.55 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	0.47162 (3)	0.70177 (2)	0.43643 (2)	0.04331 (8)
Mg1	0.56669 (9)	0.40755 (8)	0.36418 (5)	0.03510 (14)
O1	0.3353 (2)	0.4088 (2)	0.30685 (13)	0.0454 (3)
C1	0.1452 (4)	0.4898 (4)	0.3613 (2)	0.0646 (7)
H1A	0.1459	0.5477	0.4290	0.077*
H1B	0.0966	0.4047	0.3844	0.077*
C2	0.0172 (5)	0.6124 (4)	0.2880 (3)	0.0745 (8)
H2A	−0.1102	0.6646	0.3281	0.112*
H2B	0.0139	0.5553	0.2215	0.112*
H2C	0.0634	0.6981	0.2660	0.112*
C3	0.3630 (4)	0.2712 (3)	0.2340 (2)	0.0549 (6)
H3A	0.4537	0.2676	0.1682	0.066*
H3B	0.2416	0.2902	0.2077	0.066*
C4	0.4358 (4)	0.1090 (4)	0.2927 (3)	0.0650 (7)
H4A	0.4529	0.0192	0.2420	0.097*
H4B	0.3452	0.1118	0.3572	0.097*
H4C	0.5571	0.0891	0.3177	0.097*
C11	0.8009 (3)	0.2966 (3)	0.24069 (16)	0.0376 (4)
C12	0.8019 (3)	0.3733 (3)	0.13610 (18)	0.0435 (4)
C13	0.9428 (4)	0.2965 (4)	0.04831 (19)	0.0517 (5)
H13	0.9401	0.3527	−0.0206	0.062*
C14	1.0863 (3)	0.1401 (3)	0.0595 (2)	0.0509 (5)
C15	1.0878 (3)	0.0633 (3)	0.1619 (2)	0.0479 (5)
H15	1.1845	−0.0441	0.1716	0.057*
C16	0.9509 (3)	0.1396 (3)	0.25080 (18)	0.0404 (4)
C17	0.6470 (4)	0.5430 (3)	0.1164 (2)	0.0579 (6)
H17A	0.6757	0.5828	0.0425	0.087*
H17B	0.6391	0.6219	0.1731	0.087*
H17C	0.5260	0.5339	0.1207	0.087*
C18	1.2346 (4)	0.0568 (5)	−0.0371 (3)	0.0665 (8)
H18A	1.3152	0.1171	−0.0534	0.100*
H18B	1.1729	0.0580	−0.1025	0.100*
H18C	1.3118	−0.0586	−0.0178	0.100*
C19	0.9662 (4)	0.0501 (3)	0.3609 (2)	0.0531 (5)
H19A	0.8588	0.0200	0.3788	0.080*
H19B	0.9656	0.1233	0.4193	0.080*
H19C	1.0840	−0.0512	0.3560	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.05753 (14)	0.03546 (11)	0.03474 (11)	−0.01729 (8)	−0.00527 (8)	0.00114 (7)
Mg1	0.0392 (3)	0.0381 (3)	0.0299 (3)	−0.0168 (3)	−0.0070 (2)	−0.0023 (2)
O1	0.0436 (7)	0.0608 (9)	0.0388 (7)	−0.0271 (7)	−0.0068 (6)	−0.0099 (6)
C1	0.0522 (14)	0.096 (2)	0.0501 (14)	−0.0355 (14)	−0.0017 (11)	−0.0116 (14)
C2	0.0584 (16)	0.0700 (18)	0.096 (3)	−0.0244 (14)	−0.0198 (16)	−0.0042 (17)
C3	0.0679 (15)	0.0638 (14)	0.0474 (12)	−0.0386 (12)	−0.0135 (11)	−0.0086 (10)
C4	0.0670 (16)	0.0671 (16)	0.0712 (18)	−0.0358 (14)	−0.0158 (14)	0.0015 (14)
C11	0.0418 (9)	0.0448 (9)	0.0318 (9)	−0.0230 (8)	−0.0050 (7)	−0.0035 (7)
C12	0.0525 (11)	0.0531 (11)	0.0341 (9)	−0.0302 (9)	−0.0079 (8)	0.0011 (8)
C13	0.0634 (14)	0.0732 (15)	0.0318 (9)	−0.0425 (12)	−0.0006 (9)	−0.0049 (9)
C14	0.0490 (12)	0.0728 (15)	0.0440 (12)	−0.0389 (11)	0.0046 (9)	−0.0200 (10)
C15	0.0406 (10)	0.0548 (12)	0.0515 (12)	−0.0225 (9)	−0.0015 (9)	−0.0166 (10)
C16	0.0396 (9)	0.0466 (10)	0.0389 (10)	−0.0208 (8)	−0.0056 (8)	−0.0051 (8)
C17	0.0731 (16)	0.0603 (14)	0.0420 (12)	−0.0291 (12)	−0.0121 (11)	0.0120 (10)
C18	0.0574 (14)	0.098 (2)	0.0557 (15)	−0.0463 (15)	0.0119 (12)	−0.0291 (14)
C19	0.0505 (12)	0.0512 (12)	0.0490 (13)	−0.0127 (10)	−0.0075 (10)	0.0047 (10)

Br1—Mg1	2.5503 (7)	C11—C12	1.411 (3)
Br1—Mg1i	2.5900 (7)	C12—C13	1.399 (3)
Mg1—O1	2.0243 (16)	C12—C17	1.518 (4)
Mg1—C11	2.123 (2)	C13—C14	1.386 (4)
Mg1—Br1i	2.5900 (7)	C13—H13	0.9500
O1—C1	1.440 (3)	C14—C15	1.385 (4)
O1—C3	1.462 (3)	C14—C18	1.511 (3)
C1—C2	1.486 (5)	C15—C16	1.392 (3)
C1—H1A	0.9900	C15—H15	0.9500
C1—H1B	0.9900	C16—C19	1.513 (3)
C2—H2A	0.9800	C17—H17A	0.9800
C2—H2B	0.9800	C17—H17B	0.9800
C2—H2C	0.9800	C17—H17C	0.9800
C3—C4	1.488 (4)	C18—H18A	0.9800
C3—H3A	0.9900	C18—H18B	0.9800
C3—H3B	0.9900	C18—H18C	0.9800
C4—H4A	0.9800	C19—H19A	0.9800
C4—H4B	0.9800	C19—H19B	0.9800
C4—H4C	0.9800	C19—H19C	0.9800
C11—C16	1.409 (3)
Mg1—Br1—Mg1i	88.28 (2)	H4B—C4—H4C	109.5
O1—Mg1—C11	108.18 (7)	C16—C11—C12	115.81 (19)
O1—Mg1—Br1	105.96 (5)	C16—C11—Mg1	124.39 (15)
C11—Mg1—Br1	121.22 (6)	C12—C11—Mg1	119.46 (16)
O1—Mg1—Br1i	100.23 (5)	C13—C12—C11	121.6 (2)
C11—Mg1—Br1i	126.30 (6)	C13—C12—C17	118.3 (2)
Br1—Mg1—Br1i	91.72 (2)	C11—C12—C17	120.1 (2)
O1—Mg1—Mg1i	108.92 (5)	C14—C13—C12	121.5 (2)
C11—Mg1—Mg1i	142.89 (6)	C14—C13—H13	119.3
Br1—Mg1—Mg1i	46.315 (16)	C12—C13—H13	119.3
Br1i—Mg1—Mg1i	45.403 (16)	C15—C14—C13	117.6 (2)
C1—O1—C3	113.41 (19)	C15—C14—C18	121.5 (3)
C1—O1—Mg1	124.89 (15)	C13—C14—C18	120.8 (3)
C3—O1—Mg1	117.26 (15)	C14—C15—C16	121.6 (2)
O1—C1—C2	112.1 (3)	C14—C15—H15	119.2
O1—C1—H1A	109.2	C16—C15—H15	119.2
C2—C1—H1A	109.2	C15—C16—C11	121.9 (2)
O1—C1—H1B	109.2	C15—C16—C19	118.4 (2)
C2—C1—H1B	109.2	C11—C16—C19	119.79 (19)
H1A—C1—H1B	107.9	C12—C17—H17A	109.5
C1—C2—H2A	109.5	C12—C17—H17B	109.5
C1—C2—H2B	109.5	H17A—C17—H17B	109.5
H2A—C2—H2B	109.5	C12—C17—H17C	109.5
C1—C2—H2C	109.5	H17A—C17—H17C	109.5
H2A—C2—H2C	109.5	H17B—C17—H17C	109.5
H2B—C2—H2C	109.5	C14—C18—H18A	109.5
O1—C3—C4	111.2 (2)	C14—C18—H18B	109.5
O1—C3—H3A	109.4	H18A—C18—H18B	109.5
C4—C3—H3A	109.4	C14—C18—H18C	109.5
O1—C3—H3B	109.4	H18A—C18—H18C	109.5
C4—C3—H3B	109.4	H18B—C18—H18C	109.5
H3A—C3—H3B	108.0	C16—C19—H19A	109.5
C3—C4—H4A	109.5	C16—C19—H19B	109.5
C3—C4—H4B	109.5	H19A—C19—H19B	109.5
H4A—C4—H4B	109.5	C16—C19—H19C	109.5
C3—C4—H4C	109.5	H19A—C19—H19C	109.5
H4A—C4—H4C	109.5	H19B—C19—H19C	109.5
C3—O1—C1—C2	−81.3 (3)	C12—C13—C14—C15	−1.3 (3)
Mg1—O1—C1—C2	123.2 (2)	C12—C13—C14—C18	178.4 (2)
C1—O1—C3—C4	−94.6 (3)	C13—C14—C15—C16	−0.2 (3)
Mg1—O1—C3—C4	62.9 (3)	C18—C14—C15—C16	−179.8 (2)
C16—C11—C12—C13	0.5 (3)	C14—C15—C16—C11	1.8 (3)
Mg1—C11—C12—C13	−173.11 (16)	C14—C15—C16—C19	−178.0 (2)
C16—C11—C12—C17	−179.8 (2)	C12—C11—C16—C15	−1.9 (3)
Mg1—C11—C12—C17	6.6 (3)	Mg1—C11—C16—C15	171.33 (15)
C11—C12—C13—C14	1.1 (3)	C12—C11—C16—C19	177.86 (19)
C17—C12—C13—C14	−178.6 (2)	Mg1—C11—C16—C19	−8.9 (3)

D—H···A	D—H	H···A	D—H···A
C3—H3B···Cg1ii	0.99	2.83	159
C18—H18B···Cg1iii	0.98	3.05	122

	Mg—O	Mg—C	Mg—Br	Mg—Br
Title compound	2.0243 (16)	2.123 (2)	2.5503 (7)	2.5900 (7)
RUGNEM	2.011	2.131	2.558	2.580
TATNAD	2.024	2.130	2.572	2.582
CSD	2.02 (6)	2.17 (5)	2.57 (8)

Br1—Mg1	2.5503 (7)
Br1—Mg1i	2.5900 (7)
Mg1—O1	2.0243 (16)
Mg1—C11	2.123 (2)

O1—Mg1—C11	108.18 (7)
O1—Mg1—Br1	105.96 (5)
C11—Mg1—Br1	121.22 (6)
O1—Mg1—Br1i	100.23 (5)
C11—Mg1—Br1i	126.30 (6)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D—H⋯A
C3—H3B⋯Cg1ii	0.99	2.83	159
C18—H18B⋯Cg1iii	0.98	3.05	122

Symmetry codes: (ii) ; (iii) .