{2-[(Dimethyl-amino)-meth-yl]phen-yl}bis-(4-methyl-phen-yl)bis-muthane.

The title compound, [Bi(C(7)H(7))(2)(C(9)H(12)N)], was obtained by treating chlorodi(p-tol-yl)bis-muthane with o-lithio-N,N-dimethyl-benzyl-amine. An intra-molecular Bi⋯N nonbonding inter-action is observed in the distorted trigonal triaryl-bis-muth coordination of the title compound.

Related literature

For a review of the applications and structural chemistry of organobismuth compounds, see: Matano & Ikegami (2001 ▶); Silvestru et al. (1999 ▶). For related structural reports, see: Suzuki et al. (1993 ▶); Tokunaga et al. (2000a ▶,b ▶); Okajima et al. (2002 ▶).

Experimental

Crystal data

[Bi(C7H7)2(C9H12N)]

M = 525.43

Monoclinic,

a = 6.0991 (12) Å

b = 19.630 (4) Å

c = 8.3699 (16) Å

β = 93.073 (2)°

V = 1000.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 8.81 mm−1

T = 100 K

0.20 × 0.08 × 0.01 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.272, T max = 0.917

4908 measured reflections

3626 independent reflections

3410 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.037

S = 1.00

3626 reflections

231 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.86 e Å−3

Δρmin = −0.59 e Å−3

Absolute structure: Flack (1983 ▶), with 1544 Friedel pairs

Flack parameter: 0.412 (7)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810043655/si2298sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043655/si2298Isup2.hkl

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

[Bi(C7H7)2(C9H12N)]	F(000) = 508
Mr = 525.43	Dx = 1.744 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2yb	Cell parameters from 3137 reflections
a = 6.0991 (12) Å	θ = 2.4–26.9°
b = 19.630 (4) Å	µ = 8.81 mm−1
c = 8.3699 (16) Å	T = 100 K
β = 93.073 (2)°	Prismatic, colourless
V = 1000.6 (3) Å3	0.20 × 0.08 × 0.01 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	3626 independent reflections
Radiation source: fine-focus sealed tube	3410 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.272, Tmax = 0.917	k = −22→24
4908 measured reflections	l = −10→5

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)] = 0.019	H-atom parameters constrained
wR(F2) = 0.037	w = 1/[σ2(Fo2) + (0.0116P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
3626 reflections	Δρmax = 0.86 e Å−3
231 parameters	Δρmin = −0.59 e Å−3
1 restraint	Absolute structure: Flack (1983), with 1544 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.412 (7)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.6751 (8)	0.6439 (2)	0.4839 (6)	0.0163 (10)
C2	0.8412 (8)	0.6254 (3)	0.5966 (6)	0.0230 (12)
C3	0.8193 (8)	0.5693 (3)	0.6955 (6)	0.0232 (12)
C4	0.6268 (8)	0.5298 (2)	0.6864 (6)	0.0204 (11)
C5	0.4595 (8)	0.5495 (2)	0.5785 (6)	0.0216 (11)
C6	0.4845 (8)	0.6055 (2)	0.4787 (6)	0.0199 (11)
C7	0.6102 (9)	0.4657 (2)	0.7843 (6)	0.0261 (12)
C8	0.9474 (8)	0.7916 (2)	0.4269 (6)	0.0169 (11)
C9	0.8880 (8)	0.8577 (2)	0.4634 (6)	0.0181 (11)
C10	1.0307 (8)	0.9002 (2)	0.5535 (6)	0.0185 (11)
C11	1.2387 (8)	0.8775 (2)	0.6077 (6)	0.0158 (10)
C12	1.2973 (8)	0.8115 (2)	0.5681 (6)	0.0190 (11)
C13	1.1561 (8)	0.7696 (2)	0.4794 (6)	0.0176 (11)
C14	1.3902 (8)	0.9223 (2)	0.7087 (6)	0.0240 (12)
C15	0.9686 (7)	0.6605 (2)	0.1743 (5)	0.0134 (10)
C16	0.9732 (8)	0.5895 (2)	0.2016 (6)	0.0197 (11)
C17	1.1305 (9)	0.5485 (3)	0.1324 (6)	0.0248 (12)
C18	1.2779 (9)	0.5775 (3)	0.0349 (7)	0.0286 (13)
C19	1.2694 (8)	0.6474 (3)	0.0021 (6)	0.0220 (11)
C20	1.1185 (18)	0.6885 (5)	0.0734 (12)	0.019 (2)
C21	1.1160 (17)	0.7642 (5)	0.0378 (11)	0.0148 (19)
C22	0.9016 (9)	0.8666 (2)	0.0186 (6)	0.0234 (12)
C23	0.7809 (8)	0.7669 (2)	−0.1263 (6)	0.0248 (12)
N1	0.8969 (6)	0.79253 (18)	0.0204 (5)	0.0154 (9)
Bi1	0.70642 (2)	0.72364 (2)	0.286635 (16)	0.01465 (4)
H2	0.9692	0.6512	0.6057	0.028*
H3	0.9333	0.5577	0.7687	0.028*
H5	0.3285	0.5251	0.5724	0.026*
H6	0.3698	0.6174	0.4065	0.024*
H7A	0.6739	0.4284	0.7290	0.039*
H7B	0.4586	0.4560	0.8001	0.039*
H7C	0.6874	0.4719	0.8863	0.039*
H9	0.7511	0.8741	0.4273	0.022*
H10	0.9866	0.9442	0.5778	0.022*
H12	1.4351	0.7952	0.6022	0.023*
H13	1.2011	0.7258	0.4542	0.021*
H14A	1.3614	0.9164	0.8195	0.036*
H14B	1.3662	0.9691	0.6790	0.036*
H14C	1.5398	0.9102	0.6922	0.036*
H16	0.8711	0.5698	0.2661	0.024*
H17	1.1347	0.5019	0.1524	0.030*
H18	1.3842	0.5506	−0.0097	0.034*
H19	1.3657	0.6663	−0.0680	0.026*
H21A	1.1975	0.7878	0.1237	0.018*
H21B	1.1904	0.7721	−0.0600	0.018*
H22A	0.9813	0.8819	−0.0705	0.035*
H22B	0.9724	0.8829	0.1163	0.035*
H22C	0.7541	0.8837	0.0086	0.035*
H23A	0.8557	0.7820	−0.2180	0.037*
H23B	0.6332	0.7840	−0.1326	0.037*
H23C	0.7782	0.7180	−0.1241	0.037*

	U11	U22	U33	U12	U13	U23
C1	0.019 (3)	0.015 (2)	0.015 (3)	0.001 (2)	0.003 (2)	0.000 (2)
C2	0.019 (3)	0.030 (3)	0.019 (3)	−0.007 (2)	0.002 (2)	−0.002 (2)
C3	0.024 (3)	0.028 (3)	0.018 (3)	0.005 (2)	−0.002 (2)	0.004 (2)
C4	0.021 (3)	0.022 (3)	0.018 (3)	0.004 (2)	0.007 (2)	0.001 (2)
C5	0.018 (3)	0.021 (3)	0.027 (3)	−0.006 (2)	0.007 (2)	0.001 (2)
C6	0.017 (3)	0.019 (3)	0.024 (3)	0.004 (2)	−0.001 (2)	0.002 (2)
C7	0.034 (3)	0.018 (3)	0.026 (3)	0.002 (2)	0.009 (3)	0.002 (2)
C8	0.020 (3)	0.014 (2)	0.017 (3)	−0.0034 (19)	0.004 (2)	−0.0005 (19)
C9	0.020 (3)	0.015 (2)	0.019 (3)	0.002 (2)	−0.001 (2)	0.001 (2)
C10	0.027 (3)	0.014 (2)	0.016 (3)	0.001 (2)	0.007 (2)	0.000 (2)
C11	0.020 (3)	0.016 (2)	0.011 (3)	−0.005 (2)	0.002 (2)	0.0015 (19)
C12	0.017 (3)	0.021 (3)	0.019 (3)	0.003 (2)	−0.001 (2)	0.002 (2)
C13	0.022 (3)	0.015 (2)	0.016 (3)	0.000 (2)	0.004 (2)	−0.0033 (19)
C14	0.025 (3)	0.023 (3)	0.024 (3)	−0.005 (2)	0.004 (2)	−0.006 (2)
C15	0.013 (2)	0.015 (2)	0.013 (3)	0.0007 (19)	0.001 (2)	−0.0001 (19)
C16	0.026 (3)	0.017 (3)	0.015 (3)	−0.004 (2)	−0.004 (2)	−0.002 (2)
C17	0.031 (3)	0.017 (3)	0.026 (3)	0.003 (2)	−0.005 (3)	−0.003 (2)
C18	0.025 (3)	0.031 (3)	0.030 (3)	0.006 (2)	0.001 (3)	−0.011 (2)
C19	0.021 (3)	0.026 (3)	0.019 (3)	−0.006 (2)	0.002 (2)	−0.002 (2)
C20	0.017 (4)	0.020 (4)	0.020 (5)	0.000 (3)	−0.012 (3)	−0.004 (3)
C21	0.013 (4)	0.017 (4)	0.015 (4)	0.000 (3)	0.007 (3)	−0.001 (3)
C22	0.032 (3)	0.019 (3)	0.019 (3)	−0.001 (2)	0.004 (2)	0.006 (2)
C23	0.027 (3)	0.025 (3)	0.022 (3)	0.004 (2)	0.001 (2)	0.006 (2)
N1	0.013 (2)	0.016 (2)	0.017 (2)	−0.0011 (16)	0.0037 (17)	0.0023 (16)
Bi1	0.01336 (7)	0.01541 (7)	0.01517 (7)	0.0000 (2)	0.00051 (5)	−0.0003 (2)

C1—C6	1.384 (6)	C14—H14A	0.9600
C1—C2	1.394 (6)	C14—H14B	0.9600
C1—Bi1	2.291 (5)	C14—H14C	0.9600
C2—C3	1.389 (7)	C15—C20	1.391 (12)
C2—H2	0.9300	C15—C16	1.412 (6)
C3—C4	1.405 (7)	C15—Bi1	2.267 (5)
C3—H3	0.9300	C16—C17	1.401 (7)
C4—C5	1.381 (7)	C16—H16	0.9300
C4—C7	1.509 (7)	C17—C18	1.370 (7)
C5—C6	1.394 (7)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.400 (7)
C6—H6	0.9300	C18—H18	0.9300
C7—H7A	0.9600	C19—C20	1.383 (11)
C7—H7B	0.9600	C19—H19	0.9300
C7—H7C	0.9600	C20—C21	1.515 (7)
C8—C9	1.386 (6)	C21—N1	1.448 (10)
C8—C13	1.393 (6)	C21—H21A	0.9700
C8—Bi1	2.265 (5)	C21—H21B	0.9700
C9—C10	1.397 (6)	C22—N1	1.454 (6)
C9—H9	0.9300	C22—H22A	0.9600
C10—C11	1.397 (6)	C22—H22B	0.9600
C10—H10	0.9300	C22—H22C	0.9600
C11—C12	1.388 (6)	C23—N1	1.473 (6)
C11—C14	1.503 (6)	C23—H23A	0.9600
C12—C13	1.379 (6)	C23—H23B	0.9600
C12—H12	0.9300	C23—H23C	0.9600
C13—H13	0.9300	N1—Bi1	2.902 (4)
C6—C1—C2	117.3 (4)	C20—C15—C16	118.7 (6)
C6—C1—Bi1	116.8 (3)	C20—C15—Bi1	122.5 (5)
C2—C1—Bi1	125.4 (4)	C16—C15—Bi1	118.8 (4)
C3—C2—C1	121.3 (5)	C17—C16—C15	120.5 (5)
C3—C2—H2	119.4	C17—C16—H16	119.7
C1—C2—H2	119.4	C15—C16—H16	119.7
C2—C3—C4	120.8 (5)	C18—C17—C16	119.6 (5)
C2—C3—H3	119.6	C18—C17—H17	120.2
C4—C3—H3	119.6	C16—C17—H17	120.2
C5—C4—C3	117.9 (5)	C17—C18—C19	120.3 (5)
C5—C4—C7	121.3 (5)	C17—C18—H18	119.8
C3—C4—C7	120.7 (4)	C19—C18—H18	119.8
C4—C5—C6	120.7 (5)	C20—C19—C18	120.4 (6)
C4—C5—H5	119.6	C20—C19—H19	119.8
C6—C5—H5	119.6	C18—C19—H19	119.8
C1—C6—C5	122.0 (4)	C19—C20—C15	120.4 (8)
C1—C6—H6	119.0	C19—C20—C21	119.1 (11)
C5—C6—H6	119.0	C15—C20—C21	120.5 (10)
C4—C7—H7A	109.5	N1—C21—C20	113.4 (10)
C4—C7—H7B	109.5	N1—C21—H21A	108.9
H7A—C7—H7B	109.5	C20—C21—H21A	108.9
C4—C7—H7C	109.5	N1—C21—H21B	108.9
H7A—C7—H7C	109.5	C20—C21—H21B	108.9
H7B—C7—H7C	109.5	H21A—C21—H21B	107.7
C9—C8—C13	117.8 (4)	N1—C22—H22A	109.5
C9—C8—Bi1	119.7 (3)	N1—C22—H22B	109.5
C13—C8—Bi1	122.5 (3)	H22A—C22—H22B	109.5
C8—C9—C10	121.0 (4)	N1—C22—H22C	109.5
C8—C9—H9	119.5	H22A—C22—H22C	109.5
C10—C9—H9	119.5	H22B—C22—H22C	109.5
C9—C10—C11	120.9 (4)	N1—C23—H23A	109.5
C9—C10—H10	119.6	N1—C23—H23B	109.5
C11—C10—H10	119.6	H23A—C23—H23B	109.5
C12—C11—C10	117.4 (4)	N1—C23—H23C	109.5
C12—C11—C14	121.5 (4)	H23A—C23—H23C	109.5
C10—C11—C14	121.0 (4)	H23B—C23—H23C	109.5
C13—C12—C11	121.6 (4)	C21—N1—C22	111.6 (5)
C13—C12—H12	119.2	C21—N1—C23	110.6 (5)
C11—C12—H12	119.2	C22—N1—C23	110.0 (4)
C12—C13—C8	121.3 (4)	C21—N1—Bi1	98.6 (4)
C12—C13—H13	119.4	C22—N1—Bi1	118.9 (3)
C8—C13—H13	119.4	C23—N1—Bi1	106.7 (3)
C11—C14—H14A	109.5	C1—Bi1—C8	96.07 (16)
C11—C14—H14B	109.5	C1—Bi1—C15	90.74 (16)
H14A—C14—H14B	109.5	C1—Bi1—N1	157.55 (14)
C11—C14—H14C	109.5	C8—Bi1—C15	94.85 (17)
H14A—C14—H14C	109.5	C8—Bi1—N1	81.26 (14)
H14B—C14—H14C	109.5	C15—Bi1—N1	67.43 (13)

C1—Bi1	2.291 (5)
C8—Bi1	2.265 (5)
C15—Bi1	2.267 (5)
N1—Bi1	2.902 (4)

C1—Bi1—C8	96.07 (16)
C1—Bi1—C15	90.74 (16)
C1—Bi1—N1	157.55 (14)
C8—Bi1—C15	94.85 (17)
C8—Bi1—N1	81.26 (14)
C15—Bi1—N1	67.43 (13)