(Biphenyl-2-yl)bromidobis(2-methyl­tetra­hydro­furan-κO)magnesium(II)

Nordschild, S.; Wohlgemuth, D.; Bolte, M.

doi:10.1107/S1600536809012185

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m493

doi:10.1107/S1600536809012185

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(Biphenyl-2-yl)bromidobis(2-methyltetrahydrofuran-κO)magnesium(II)

Simon Nordschild,^a D. Wohlgemuth ^a and Michael Bolte ^b ^*

^aChemetall GmbH, Lithium Division, Trakehner Strasse 3, 60487 Frankfurt am Main, Germany, and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 23 March 2009; accepted 1 April 2009; online 8 April 2009)

In the title Grignard reagent, [MgBr(C₁₂H₉)(C₅H₁₀O)₂], the Mg centre adopts a distorted tetrahedral MgCO₂Br arrangement. The dihedral angle between the two aromatic rings of the biphenyl residue is 44.00 (14)°. Each molecule incorporates one R- and one S-configured 2-methyltetrahydrofuran molecule.

Related literature

For background to Grignard-type compounds, see Elschenbroich (2008 ); Schwetlick (1996 ); Silverman & Rakita (1996 ).

Experimental

Crystal data

[MgBr(C₁₂H₉)(C₅H₁₀O)₂]
M_r = 429.67
Monoclinic, P 2₁ /n
a = 11.6887 (5) Å
b = 16.8061 (9) Å
c = 11.7888 (5) Å
β = 103.757 (4)°
V = 2249.38 (18) Å³
Z = 4
Mo Kα radiation
μ = 1.87 mm⁻¹
T = 173 K
0.29 × 0.28 × 0.26 mm

Data collection

Stoe IPDSII two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2003 ; Blessing, 1995 ) T_min = 0.614, T_max = 0.642
54470 measured reflections
4107 independent reflections
3484 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.108
S = 1.05
4107 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Mg1—O1	2.022 (2)
Mg1—O11	2.030 (2)
Mg1—C21	2.143 (3)
Mg1—Br1	2.4750 (10)

O1—Mg1—O11	97.02 (10)
O1—Mg1—C21	114.41 (11)
O11—Mg1—C21	106.87 (11)
O1—Mg1—Br1	109.97 (9)
O11—Mg1—Br1	104.75 (7)
C21—Mg1—Br1	120.53 (8)

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: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809012185/hb2933sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012185/hb2933Isup2.hkl

checkCIF report

Comment top

The title compound is a Grignard reagent, a kind of compounds which is widely used for C—C bond formation or as base in organic chemistry. The Mg centre is four coordinate in a distorted tetrahedral fashion. The bond angles range from 97.02 (1)° for O—Mg—O to 120.53 (8)° for C—Mg—Br. The bond lengths are 2.4750 (10)Å for Mg—Br, 2.143 (3)Å for Mg—C and 2.022 (2)° and 2.030 (2)Å for the Mg—O bonds. The dihedral angles between the two aromatic rings of the biphenyl residue is 44.00 (14)°.

Related literature top

For background to Grignard-type compounds, see Elschenbroich (2008); Schwetlick (1996); Silverman & Rakita (1996).

Experimental top

This compound is commercially available from Chemetall GmbH (CAS 82214–69-5, Product No. 408562). Colourless blocks of (I) were obtained from a solution due to long term storage at ambient temperature.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Perspective view of (I) with displacement ellipsoids drawn at the 50% probability level; H atoms omitted for clarity.

(Biphenyl-2-yl)bromidobis(2-methyltetrahydrofuran-κO)magnesium(II) top

Crystal data top

[MgBr(C₁₂H₉)(C₅H₁₀O)₂]	F(000) = 896
M_r = 429.67	D_x = 1.269 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 40381 reflections
a = 11.6887 (5) Å	θ = 3.6–26.6°
b = 16.8061 (9) Å	µ = 1.87 mm⁻¹
c = 11.7888 (5) Å	T = 173 K
β = 103.757 (4)°	Block, colourless
V = 2249.38 (18) Å³	0.29 × 0.28 × 0.26 mm
Z = 4

Data collection top

Stoe IPDSII two-circle diffractometer	4107 independent reflections
Radiation source: fine-focus sealed tube	3484 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
ω scans	θ_max = 25.4°, θ_min = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −14→14
T_min = 0.614, T_max = 0.642	k = −20→20
54470 measured reflections	l = −14→14

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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.0462P)² + 2.3133P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4107 reflections	Δρ_max = 0.76 e Å⁻³
236 parameters	Δρ_min = −0.41 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0043 (6)

Crystal data top

[MgBr(C₁₂H₉)(C₅H₁₀O)₂]	V = 2249.38 (18) Å³
M_r = 429.67	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.6887 (5) Å	µ = 1.87 mm⁻¹
b = 16.8061 (9) Å	T = 173 K
c = 11.7888 (5) Å	0.29 × 0.28 × 0.26 mm
β = 103.757 (4)°

Data collection top

Stoe IPDSII two-circle diffractometer	4107 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	3484 reflections with I > 2σ(I)
T_min = 0.614, T_max = 0.642	R_int = 0.069
54470 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.05	Δρ_max = 0.76 e Å⁻³
4107 reflections	Δρ_min = −0.41 e Å⁻³
236 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Mg1	0.56815 (8)	0.31486 (6)	0.70780 (8)	0.0349 (2)
Br1	0.60093 (3)	0.24360 (2)	0.89652 (3)	0.05398 (15)
O1	0.4214 (2)	0.38260 (15)	0.6841 (2)	0.0572 (6)
C2	0.4112 (4)	0.4578 (4)	0.6045 (5)	0.0967 (17)
H2A	0.4898	0.4781	0.6011	0.116*
H2B	0.3649	0.4465	0.5243	0.116*
C3	0.3515 (7)	0.5122 (4)	0.6625 (8)	0.159 (4)
H3A	0.3114	0.5542	0.6085	0.190*
H3B	0.4067	0.5376	0.7296	0.190*
C4	0.2618 (6)	0.4595 (5)	0.7036 (7)	0.145 (3)
H4A	0.2312	0.4860	0.7653	0.173*
H4B	0.1951	0.4450	0.6379	0.173*
C5	0.3367 (5)	0.3866 (6)	0.7512 (5)	0.143 (3)
H5	0.3763	0.3948	0.8354	0.172*
C6	0.2702 (6)	0.3147 (6)	0.7372 (7)	0.170 (4)
H6A	0.3212	0.2705	0.7720	0.256*
H6B	0.2383	0.3044	0.6539	0.256*
H6C	0.2052	0.3199	0.7762	0.256*
O11	0.50159 (19)	0.23129 (11)	0.58553 (18)	0.0412 (5)
C12	0.4587 (3)	0.2531 (2)	0.4632 (3)	0.0536 (8)
H12A	0.4940	0.3040	0.4464	0.064*
H12B	0.3718	0.2587	0.4430	0.064*
C13	0.4955 (5)	0.1870 (3)	0.3968 (4)	0.0852 (15)
H13A	0.4355	0.1777	0.3231	0.102*
H13B	0.5713	0.1998	0.3774	0.102*
C14	0.5080 (4)	0.1158 (2)	0.4719 (4)	0.0672 (11)
H14A	0.5833	0.0884	0.4732	0.081*
H14B	0.4426	0.0782	0.4422	0.081*
C15	0.5056 (3)	0.14444 (18)	0.5944 (3)	0.0521 (9)
H15	0.5799	0.1279	0.6508	0.063*
C16	0.4023 (4)	0.1148 (3)	0.6359 (4)	0.0790 (13)
H16A	0.4065	0.1351	0.7147	0.119*
H16B	0.4032	0.0565	0.6373	0.119*
H16C	0.3294	0.1334	0.5829	0.119*
C21	0.7121 (2)	0.37048 (16)	0.6550 (2)	0.0341 (6)
C22	0.7636 (2)	0.44648 (17)	0.6866 (3)	0.0395 (7)
C23	0.8611 (3)	0.4719 (2)	0.6460 (3)	0.0549 (9)
H23	0.8928	0.5234	0.6666	0.066*
C24	0.9121 (3)	0.4234 (3)	0.5767 (4)	0.0627 (11)
H24	0.9794	0.4411	0.5518	0.075*
C25	0.8648 (3)	0.3495 (2)	0.5439 (3)	0.0542 (9)
H25	0.8986	0.3159	0.4959	0.065*
C26	0.7668 (3)	0.32490 (18)	0.5821 (3)	0.0419 (7)
H26	0.7345	0.2741	0.5577	0.050*
C31	0.6804 (3)	0.4711 (2)	0.8611 (3)	0.0483 (8)
H31	0.6914	0.4163	0.8802	0.058*
C32	0.7136 (3)	0.50025 (17)	0.7624 (3)	0.0442 (8)
C33	0.6971 (4)	0.5819 (2)	0.7384 (3)	0.0638 (11)
H33	0.7205	0.6039	0.6732	0.077*
C34	0.6474 (5)	0.6307 (2)	0.8081 (4)	0.0854 (16)
H34	0.6354	0.6855	0.7890	0.102*
C35	0.6154 (4)	0.6014 (3)	0.9041 (4)	0.0853 (16)
H35	0.5821	0.6356	0.9517	0.102*
C36	0.6318 (4)	0.5206 (2)	0.9319 (3)	0.0656 (11)
H36	0.6099	0.4997	0.9986	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mg1	0.0308 (5)	0.0364 (5)	0.0377 (5)	−0.0051 (4)	0.0085 (4)	−0.0023 (4)
Br1	0.0496 (2)	0.0716 (3)	0.0401 (2)	−0.01271 (17)	0.00923 (14)	0.00894 (16)
O1	0.0412 (13)	0.0673 (16)	0.0586 (15)	0.0132 (11)	0.0029 (11)	−0.0154 (12)
C2	0.059 (3)	0.116 (4)	0.106 (4)	0.027 (3)	0.002 (3)	0.014 (3)
C3	0.129 (6)	0.114 (5)	0.174 (8)	0.051 (5)	−0.082 (6)	−0.039 (5)
C4	0.103 (5)	0.204 (8)	0.133 (6)	0.102 (6)	0.039 (4)	−0.001 (5)
C5	0.080 (4)	0.269 (10)	0.082 (4)	0.081 (5)	0.023 (3)	−0.001 (5)
C6	0.086 (5)	0.277 (12)	0.145 (7)	−0.072 (6)	0.022 (4)	0.027 (7)
O11	0.0477 (12)	0.0308 (11)	0.0408 (11)	−0.0064 (9)	0.0017 (9)	0.0021 (8)
C12	0.065 (2)	0.0477 (19)	0.0407 (17)	−0.0002 (17)	−0.0019 (15)	0.0043 (15)
C13	0.137 (5)	0.065 (3)	0.054 (2)	−0.002 (3)	0.024 (3)	−0.013 (2)
C14	0.072 (3)	0.050 (2)	0.075 (3)	0.0072 (19)	0.009 (2)	−0.0172 (19)
C15	0.054 (2)	0.0317 (16)	0.061 (2)	−0.0068 (14)	−0.0061 (16)	0.0057 (15)
C16	0.090 (3)	0.069 (3)	0.073 (3)	−0.043 (2)	0.010 (2)	0.003 (2)
C21	0.0299 (13)	0.0292 (14)	0.0409 (15)	0.0013 (11)	0.0038 (11)	0.0036 (12)
C22	0.0312 (14)	0.0343 (15)	0.0451 (17)	−0.0061 (12)	−0.0063 (12)	0.0082 (13)
C23	0.0436 (19)	0.054 (2)	0.058 (2)	−0.0204 (16)	−0.0055 (16)	0.0150 (17)
C24	0.0345 (17)	0.086 (3)	0.067 (2)	−0.0100 (18)	0.0113 (16)	0.025 (2)
C25	0.0435 (18)	0.066 (2)	0.057 (2)	0.0104 (17)	0.0198 (16)	0.0174 (18)
C26	0.0397 (16)	0.0364 (16)	0.0507 (18)	0.0063 (13)	0.0129 (14)	0.0064 (13)
C31	0.0481 (18)	0.0392 (17)	0.0478 (19)	0.0046 (14)	−0.0079 (14)	−0.0072 (14)
C32	0.0417 (16)	0.0341 (16)	0.0450 (18)	−0.0045 (13)	−0.0132 (13)	−0.0052 (13)
C33	0.082 (3)	0.0333 (18)	0.055 (2)	−0.0038 (17)	−0.0242 (19)	−0.0040 (16)
C34	0.124 (4)	0.038 (2)	0.065 (3)	0.015 (2)	−0.035 (3)	−0.017 (2)
C35	0.103 (4)	0.064 (3)	0.066 (3)	0.033 (2)	−0.025 (3)	−0.034 (2)
C36	0.069 (2)	0.068 (2)	0.049 (2)	0.013 (2)	−0.0076 (18)	−0.0172 (18)

Geometric parameters (Å, º) top

Mg1—O1	2.022 (2)	C14—H14A	0.9900
Mg1—O11	2.030 (2)	C14—H14B	0.9900
Mg1—C21	2.143 (3)	C15—C16	1.492 (5)
Mg1—Br1	2.4750 (10)	C15—H15	1.0000
O1—C5	1.408 (6)	C16—H16A	0.9800
O1—C2	1.562 (6)	C16—H16B	0.9800
C2—C3	1.421 (9)	C16—H16C	0.9800
C2—H2A	0.9900	C21—C26	1.412 (4)
C2—H2B	0.9900	C21—C22	1.424 (4)
C3—C4	1.536 (11)	C22—C23	1.403 (5)
C3—H3A	0.9900	C22—C32	1.485 (5)
C3—H3B	0.9900	C23—C24	1.385 (6)
C4—C5	1.533 (9)	C23—H23	0.9500
C4—H4A	0.9900	C24—C25	1.377 (6)
C4—H4B	0.9900	C24—H24	0.9500
C5—C6	1.425 (11)	C25—C26	1.390 (4)
C5—H5	1.0000	C25—H25	0.9500
C6—H6A	0.9800	C26—H26	0.9500
C6—H6B	0.9800	C31—C36	1.393 (5)
C6—H6C	0.9800	C31—C32	1.399 (5)
O11—C12	1.456 (4)	C31—H31	0.9500
O11—C15	1.463 (4)	C32—C33	1.404 (4)
C12—C13	1.481 (5)	C33—C34	1.384 (6)
C12—H12A	0.9900	C33—H33	0.9500
C12—H12B	0.9900	C34—C35	1.366 (7)
C13—C14	1.475 (6)	C34—H34	0.9500
C13—H13A	0.9900	C35—C36	1.398 (6)
C13—H13B	0.9900	C35—H35	0.9500
C14—C15	1.529 (5)	C36—H36	0.9500

O1—Mg1—O11	97.02 (10)	C13—C14—C15	106.8 (3)
O1—Mg1—C21	114.41 (11)	C13—C14—H14A	110.4
O11—Mg1—C21	106.87 (11)	C15—C14—H14A	110.4
O1—Mg1—Br1	109.97 (9)	C13—C14—H14B	110.4
O11—Mg1—Br1	104.75 (7)	C15—C14—H14B	110.4
C21—Mg1—Br1	120.53 (8)	H14A—C14—H14B	108.6
C5—O1—C2	109.6 (4)	O11—C15—C16	110.0 (3)
C5—O1—Mg1	129.5 (3)	O11—C15—C14	104.7 (3)
C2—O1—Mg1	118.7 (2)	C16—C15—C14	113.8 (3)
C3—C2—O1	102.0 (5)	O11—C15—H15	109.4
C3—C2—H2A	111.4	C16—C15—H15	109.4
O1—C2—H2A	111.4	C14—C15—H15	109.4
C3—C2—H2B	111.4	C15—C16—H16A	109.5
O1—C2—H2B	111.4	C15—C16—H16B	109.5
H2A—C2—H2B	109.2	H16A—C16—H16B	109.5
C2—C3—C4	103.3 (6)	C15—C16—H16C	109.5
C2—C3—H3A	111.1	H16A—C16—H16C	109.5
C4—C3—H3A	111.1	H16B—C16—H16C	109.5
C2—C3—H3B	111.1	C26—C21—C22	114.9 (3)
C4—C3—H3B	111.1	C26—C21—Mg1	116.1 (2)
H3A—C3—H3B	109.1	C22—C21—Mg1	128.9 (2)
C5—C4—C3	101.7 (5)	C23—C22—C21	120.8 (3)
C5—C4—H4A	111.4	C23—C22—C32	119.2 (3)
C3—C4—H4A	111.4	C21—C22—C32	120.0 (3)
C5—C4—H4B	111.4	C24—C23—C22	121.3 (3)
C3—C4—H4B	111.4	C24—C23—H23	119.3
H4A—C4—H4B	109.3	C22—C23—H23	119.3
O1—C5—C6	109.4 (6)	C25—C24—C23	119.7 (3)
O1—C5—C4	104.4 (6)	C25—C24—H24	120.1
C6—C5—C4	112.8 (7)	C23—C24—H24	120.1
O1—C5—H5	110.0	C24—C25—C26	119.0 (3)
C6—C5—H5	110.0	C24—C25—H25	120.5
C4—C5—H5	110.0	C26—C25—H25	120.5
C5—C6—H6A	109.5	C25—C26—C21	124.2 (3)
C5—C6—H6B	109.5	C25—C26—H26	117.9
H6A—C6—H6B	109.5	C21—C26—H26	117.9
C5—C6—H6C	109.5	C36—C31—C32	121.6 (3)
H6A—C6—H6C	109.5	C36—C31—H31	119.2
H6B—C6—H6C	109.5	C32—C31—H31	119.2
C12—O11—C15	108.6 (2)	C31—C32—C33	117.2 (3)
C12—O11—Mg1	120.80 (18)	C31—C32—C22	121.0 (3)
C15—O11—Mg1	129.73 (19)	C33—C32—C22	121.8 (3)
O11—C12—C13	105.0 (3)	C34—C33—C32	121.1 (4)
O11—C12—H12A	110.7	C34—C33—H33	119.5
C13—C12—H12A	110.7	C32—C33—H33	119.5
O11—C12—H12B	110.7	C35—C34—C33	121.0 (4)
C13—C12—H12B	110.7	C35—C34—H34	119.5
H12A—C12—H12B	108.8	C33—C34—H34	119.5
C14—C13—C12	106.9 (3)	C34—C35—C36	119.7 (4)
C14—C13—H13A	110.3	C34—C35—H35	120.1
C12—C13—H13A	110.3	C36—C35—H35	120.1
C14—C13—H13B	110.3	C31—C36—C35	119.4 (4)
C12—C13—H13B	110.3	C31—C36—H36	120.3
H13A—C13—H13B	108.6	C35—C36—H36	120.3

O11—Mg1—O1—C5	101.5 (5)	C13—C14—C15—C16	115.6 (4)
C21—Mg1—O1—C5	−146.4 (5)	O1—Mg1—C21—C26	−130.5 (2)
Br1—Mg1—O1—C5	−7.1 (5)	O11—Mg1—C21—C26	−24.4 (2)
O11—Mg1—O1—C2	−97.5 (3)	Br1—Mg1—C21—C26	94.8 (2)
C21—Mg1—O1—C2	14.7 (3)	O1—Mg1—C21—C22	52.0 (3)
Br1—Mg1—O1—C2	154.0 (3)	O11—Mg1—C21—C22	158.2 (2)
C5—O1—C2—C3	20.6 (6)	Br1—Mg1—C21—C22	−82.6 (3)
Mg1—O1—C2—C3	−144.0 (4)	C26—C21—C22—C23	0.3 (4)
O1—C2—C3—C4	−38.6 (5)	Mg1—C21—C22—C23	177.7 (2)
C2—C3—C4—C5	43.7 (7)	C26—C21—C22—C32	179.6 (3)
C2—O1—C5—C6	127.7 (6)	Mg1—C21—C22—C32	−2.9 (4)
Mg1—O1—C5—C6	−69.9 (7)	C21—C22—C23—C24	−1.6 (5)
C2—O1—C5—C4	6.8 (7)	C32—C22—C23—C24	179.0 (3)
Mg1—O1—C5—C4	169.2 (4)	C22—C23—C24—C25	1.7 (5)
C3—C4—C5—O1	−29.7 (8)	C23—C24—C25—C26	−0.4 (5)
C3—C4—C5—C6	−148.4 (7)	C24—C25—C26—C21	−1.0 (5)
O1—Mg1—O11—C12	60.3 (3)	C22—C21—C26—C25	1.1 (4)
C21—Mg1—O11—C12	−57.9 (3)	Mg1—C21—C26—C25	−176.7 (2)
Br1—Mg1—O11—C12	173.1 (2)	C36—C31—C32—C33	0.8 (5)
O1—Mg1—O11—C15	−131.4 (3)	C36—C31—C32—C22	−179.0 (3)
C21—Mg1—O11—C15	110.4 (3)	C23—C22—C32—C31	−136.9 (3)
Br1—Mg1—O11—C15	−18.6 (3)	C21—C22—C32—C31	43.7 (4)
C15—O11—C12—C13	−28.8 (4)	C23—C22—C32—C33	43.3 (4)
Mg1—O11—C12—C13	141.7 (3)	C21—C22—C32—C33	−136.1 (3)
O11—C12—C13—C14	25.2 (5)	C31—C32—C33—C34	−1.6 (5)
C12—C13—C14—C15	−12.7 (5)	C22—C32—C33—C34	178.2 (3)
C12—O11—C15—C16	−102.0 (3)	C32—C33—C34—C35	1.6 (6)
Mg1—O11—C15—C16	88.6 (3)	C33—C34—C35—C36	−0.7 (7)
C12—O11—C15—C14	20.7 (4)	C32—C31—C36—C35	0.1 (5)
Mg1—O11—C15—C14	−148.7 (2)	C34—C35—C36—C31	−0.1 (6)
C13—C14—C15—O11	−4.6 (4)

Experimental details

Crystal data
Chemical formula	[MgBr(C₁₂H₉)(C₅H₁₀O)₂]
M_r	429.67
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	11.6887 (5), 16.8061 (9), 11.7888 (5)
β (°)	103.757 (4)
V (Å³)	2249.38 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.87
Crystal size (mm)	0.29 × 0.28 × 0.26

Data collection
Diffractometer	Stoe IPDSII two-circle diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2003; Blessing, 1995)
T_min, T_max	0.614, 0.642
No. of measured, independent and observed [I > 2σ(I)] reflections	54470, 4107, 3484
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.108, 1.05
No. of reflections	4107
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.41

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL-Plus (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Mg1—O1	2.022 (2)	Mg1—C21	2.143 (3)
Mg1—O11	2.030 (2)	Mg1—Br1	2.4750 (10)

O1—Mg1—O11	97.02 (10)	O1—Mg1—Br1	109.97 (9)
O1—Mg1—C21	114.41 (11)	O11—Mg1—Br1	104.75 (7)
O11—Mg1—C21	106.87 (11)	C21—Mg1—Br1	120.53 (8)

References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Elschenbroich, C. (2008). In Organometallchemie. Stuttgart: Teubner BG. Google Scholar
Schwetlick, K. (1996). In Organikum. Heidelberg: Johann Ambrosius Barth. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Silverman, G. S. & Rakita, P. E. (1996). In Handbook of Grignard Reagents. New York: Dekker. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar