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ISSN: 2056-9890

{2-[(Di­methyl­amino)­meth­yl]phen­yl}bis­­(4-methyl­phen­yl)bis­­muthane

aFaculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, Shido, Sanuki 769-2193, Japan, and bFaculty of Pharmaceutical Sciences, Hokuriku University, Kanagawa-machi, Kanazawa 920-1181, Japan
*Correspondence e-mail: j-kurita@hokuriku-u.ac.jp

(Received 4 October 2010; accepted 26 October 2010; online 4 December 2010)

The title compound, [Bi(C7H7)2(C9H12N)], was obtained by treating chlorodi(p-tol­yl)bis­muthane with o-lithio-N,N-dimethyl­benzyl­amine. An intra­molecular Bi⋯N nonbonding inter­action is observed in the distorted trigonal triaryl­bis­muth coordination of the title compound.

Related literature

For a review of the applications and structural chemistry of organobismuth compounds, see: Matano & Ikegami (2001[Matano, Y. & Ikegami, T. (2001). Organobismuth Chemistry, edited by H. Suzuki & Y. Matano, pp. 21-246. Amsterdam: Elsevier.]); Silvestru et al. (1999[Silvestru, C., Breunig, H. J. & Althaus, H. (1999). Chem. Rev. 99, 3277-3327.]). For related structural reports, see: Suzuki et al. (1993[Suzuki, H., Murafuji, T., Matano, Y. & Azuma, N. (1993). J. Chem. Soc. Perkin Trans. 1, pp. 2969-2973.]); Tokunaga et al. (2000a[Tokunaga, T., Seki, H., Yasuike, S., Ikoma, M., Kurita, J. & Yamaguchi, K. (2000a). Tetrahedron, 56, 8833-8839.],b[Tokunaga, T., Seki, H., Yasuike, S., Ikoma, M., Kurita, J. & Yamaguchi, K. (2000b). Tetrahedron Lett. 41, 1031-1034.]); Okajima et al. (2002[Okajima, S., Yasuike, S., Kakuswa, N., Osada, A., Yamaguchi, K., Seki, H. & Kurita, J. (2002). J. Organomet. Chem. 656, 234-242.]).

[Scheme 1]

Experimental

Crystal data
  • [Bi(C7H7)2(C9H12N)]

  • Mr = 525.43

  • Monoclinic, P 21

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.272, Tmax = 0.917

  • 4908 measured reflections

  • 3626 independent reflections

  • 3410 reflections with I > 2σ(I)

  • Rint = 0.016

Refinement
  • R[F2 > 2σ(F2)] = 0.019

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), with 1544 Friedel pairs

  • Flack parameter: 0.412 (7)

Table 1
Selected geometric parameters (Å, °)

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)

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

Interest in the chemistry of organobisumuth(III) compounds has increased in recent years, due to the potential reagents and catalysts in organic synthesis as well as biological activity (Matano & Ikegami, 2001). Among these, the structural chemistry of bismuth compounds, including intramolecular interaction between bismuth and heteroatoms, has been widely reported in a review (Silvestru et al. 1999). On the other hand, we have recently reported the synthesis and structure of various organoantimony(III) compounds, such as 1-[8-(N,N-dimethylaminomethyl)naphthyl]bis(4-methylphenyl)stibane (Tokunaga et al., 2000a), [2-(N,N-dimethylaminomethyl)phenyl]bis(4-methylphenyl)stibane (Tokunaga et al., 2000b), and Sb(S)-[2-(S)-(N,N-dimethylaminomethyl)phenyl](1-naphthyl)(4-methylphenyl)stibane (Okajima et al., 2002), bearing the CH2NMe2 moiety adjacent to the Sb atom as a pendant arm. X-ray crystal analyses of these compounds revealed the presence of intramolecular coordination between the Sb and N atoms. Here we report the synthesis and structure of the title compound, in which the central Sb atom of the [2-(N,N-dimethylaminomethyl)phenyl]bis(4-methylphenyl)stibane is replaced with Bi atom. The molecular structure and atom-numbering of the title compound are shown in Fig. 1. Selected geometric parameters are presented in Table 1. The analysis revealed that the Bi and three C (C1, C8, and C15) atoms exhibit a distorted trigonal-pyramidal arrangement with the Bi atom being far from the basal three-carbon plane (1.220 (3) Å). In addition, an intramolecular coordination between the Bi and N atoms is observed; the distance between the Bi and N atoms is 2.902 (4) Å, which corresponds to 74% of the sum of the van der Waals radii of both elements (3.94 Å) and accords with 131% of the covalent bond length (2.22 Å). It should be noted that the bond angle for C1—Bi1—N1 [157.55 (14)°] is significantly larger than those for C8—Bi1—N1 [81.26 (14)°] and C15—Bi1—N1 [67.43 (13)°], and the bond distance between Bi1 and C1 [2.291 (5) Å] is obviously longer than those for Bi1–C8 [2.265 (5) Å] and C15 [2.267 (5) Å]. The results imply that the central Bi atom is distorted equatorial vacant trigonal bipyramidal configuration with the N1 of the pendant arm and the C1 of the tolyl group being apical positions, similar to the geometry of chloro[2-(N,N-dimethylaminomethyl)phenyl](4-methylphenyl)bismuthane (Suzuki et al., 1993). These results showed that the title compound is a hypervalent compound with 10-Bi-4 system, by analogy with the 10-Sb-4 system of the organoantimony compounds (Tokunaga et al., 2000a,b; Okajima et al., 2002).

Related literature top

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 top

The title compound was synthesized as follows: To a solution of N,N-dimethylbenzylamine (1.89 g, 14.0 mmol) in ether (25 ml) was added n-butyllithium (1.65 M in hexane, 10.2 ml, 16.8 mmol) at 273 K under an argon atmosphere, and the mixture was stirred for 24 h at room temperature. To this solution was added a suspension of chlorobis(4-methylphenyl)bismuthane [prepared by the redistribution reaction on the treatment of tris(4-methylphenyl)bismuthane (2.31 g, 4.8 mmol) and trichlorobismuthane (756 mg, 2.4 mmol) in ether (20 ml) at room temperature for 2 h] over 10 min at 273 K, and the mixture was stirred for 24 h at the same temperature. The mixture was quenched with water (100 ml) and diluted with CH2Cl2 (100 ml), and insoluble substances were removed by filtration. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (50 ml). The combined organic layer was washed with brine, dried and evaporated in vacuo. Purification of the residue by recrystallization from CH3CN gave 2-(N,N-dimethylaminomethyl)phenylbis(4-methylphenyl)bismuthane as colourless prisms (2.0 g, 53% yield; m.p. 372–374 K; 1H NMR (CDCl3): δ 1.98 (s, 6H), 2.30 (s, 6H), 3.40 (s, 2H), 7.14 (d, J = 7.3 Hz, 4H), 7.16 (m, 1H), 7.25 (m, 2H), 7.62 (d, J = 7.3 Hz, 4H), 7.80 (d, J = 6.9 Hz, 1H); 13C NMR (CDCl3): δ 21.5 (q), 44.5 (q), 67.1 (t), 127.2 (d), 129.3 (d), 129.6 (d), 130.8 (d), 136.5 (s), 137.7 (d), 139.6 (d), 145.1 (s), 155.9 (s), 158.5 (s); analysis calculated for C23H26BiN: C 52.58, H 4.99, N 2.67%; found: C 52.57, H 4.92, N 2.63%.

Refinement top

The H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and were included in the refinement in the riding model approximation, with Uiso(H) = xUeq(C, N), where x = 1.5 for methyl and x = 1.2 for all other H atoms. The crystal studied was a twin with the refined BASF ratio of 0.412 (7)/0.588 (7). The Flack parameter = 0.412 (7) was refined in the full matrix least-squares process using the TWIN/BASF option.

Structure description top

Interest in the chemistry of organobisumuth(III) compounds has increased in recent years, due to the potential reagents and catalysts in organic synthesis as well as biological activity (Matano & Ikegami, 2001). Among these, the structural chemistry of bismuth compounds, including intramolecular interaction between bismuth and heteroatoms, has been widely reported in a review (Silvestru et al. 1999). On the other hand, we have recently reported the synthesis and structure of various organoantimony(III) compounds, such as 1-[8-(N,N-dimethylaminomethyl)naphthyl]bis(4-methylphenyl)stibane (Tokunaga et al., 2000a), [2-(N,N-dimethylaminomethyl)phenyl]bis(4-methylphenyl)stibane (Tokunaga et al., 2000b), and Sb(S)-[2-(S)-(N,N-dimethylaminomethyl)phenyl](1-naphthyl)(4-methylphenyl)stibane (Okajima et al., 2002), bearing the CH2NMe2 moiety adjacent to the Sb atom as a pendant arm. X-ray crystal analyses of these compounds revealed the presence of intramolecular coordination between the Sb and N atoms. Here we report the synthesis and structure of the title compound, in which the central Sb atom of the [2-(N,N-dimethylaminomethyl)phenyl]bis(4-methylphenyl)stibane is replaced with Bi atom. The molecular structure and atom-numbering of the title compound are shown in Fig. 1. Selected geometric parameters are presented in Table 1. The analysis revealed that the Bi and three C (C1, C8, and C15) atoms exhibit a distorted trigonal-pyramidal arrangement with the Bi atom being far from the basal three-carbon plane (1.220 (3) Å). In addition, an intramolecular coordination between the Bi and N atoms is observed; the distance between the Bi and N atoms is 2.902 (4) Å, which corresponds to 74% of the sum of the van der Waals radii of both elements (3.94 Å) and accords with 131% of the covalent bond length (2.22 Å). It should be noted that the bond angle for C1—Bi1—N1 [157.55 (14)°] is significantly larger than those for C8—Bi1—N1 [81.26 (14)°] and C15—Bi1—N1 [67.43 (13)°], and the bond distance between Bi1 and C1 [2.291 (5) Å] is obviously longer than those for Bi1–C8 [2.265 (5) Å] and C15 [2.267 (5) Å]. The results imply that the central Bi atom is distorted equatorial vacant trigonal bipyramidal configuration with the N1 of the pendant arm and the C1 of the tolyl group being apical positions, similar to the geometry of chloro[2-(N,N-dimethylaminomethyl)phenyl](4-methylphenyl)bismuthane (Suzuki et al., 1993). These results showed that the title compound is a hypervalent compound with 10-Bi-4 system, by analogy with the 10-Sb-4 system of the organoantimony compounds (Tokunaga et al., 2000a,b; Okajima et al., 2002).

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).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top
[Figure 1] Fig. 1. View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radii.
{2-[(Dimethylamino)methyl]phenyl}bis(4-methylphenyl)bismuthane top
Crystal data top
[Bi(C7H7)2(C9H12N)]F(000) = 508
Mr = 525.43Dx = 1.744 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2ybCell parameters from 3137 reflections
a = 6.0991 (12) Åθ = 2.4–26.9°
b = 19.630 (4) ŵ = 8.81 mm1
c = 8.3699 (16) ÅT = 100 K
β = 93.073 (2)°Prismatic, colourless
V = 1000.6 (3) Å30.20 × 0.08 × 0.01 mm
Z = 2
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3626 independent reflections
Radiation source: fine-focus sealed tube3410 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
φ and ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 77
Tmin = 0.272, Tmax = 0.917k = 2224
4908 measured reflectionsl = 105
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.019H-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 reflectionsΔρmax = 0.86 e Å3
231 parametersΔρmin = 0.59 e Å3
1 restraintAbsolute structure: Flack (1983), with 1544 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.412 (7)
Crystal data top
[Bi(C7H7)2(C9H12N)]V = 1000.6 (3) Å3
Mr = 525.43Z = 2
Monoclinic, P21Mo Kα radiation
a = 6.0991 (12) ŵ = 8.81 mm1
b = 19.630 (4) ÅT = 100 K
c = 8.3699 (16) Å0.20 × 0.08 × 0.01 mm
β = 93.073 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3626 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3410 reflections with I > 2σ(I)
Tmin = 0.272, Tmax = 0.917Rint = 0.016
4908 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.019H-atom parameters constrained
wR(F2) = 0.037Δρmax = 0.86 e Å3
S = 1.00Δρmin = 0.59 e Å3
3626 reflectionsAbsolute structure: Flack (1983), with 1544 Friedel pairs
231 parametersAbsolute structure parameter: 0.412 (7)
1 restraint
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.6751 (8)0.6439 (2)0.4839 (6)0.0163 (10)
C20.8412 (8)0.6254 (3)0.5966 (6)0.0230 (12)
C30.8193 (8)0.5693 (3)0.6955 (6)0.0232 (12)
C40.6268 (8)0.5298 (2)0.6864 (6)0.0204 (11)
C50.4595 (8)0.5495 (2)0.5785 (6)0.0216 (11)
C60.4845 (8)0.6055 (2)0.4787 (6)0.0199 (11)
C70.6102 (9)0.4657 (2)0.7843 (6)0.0261 (12)
C80.9474 (8)0.7916 (2)0.4269 (6)0.0169 (11)
C90.8880 (8)0.8577 (2)0.4634 (6)0.0181 (11)
C101.0307 (8)0.9002 (2)0.5535 (6)0.0185 (11)
C111.2387 (8)0.8775 (2)0.6077 (6)0.0158 (10)
C121.2973 (8)0.8115 (2)0.5681 (6)0.0190 (11)
C131.1561 (8)0.7696 (2)0.4794 (6)0.0176 (11)
C141.3902 (8)0.9223 (2)0.7087 (6)0.0240 (12)
C150.9686 (7)0.6605 (2)0.1743 (5)0.0134 (10)
C160.9732 (8)0.5895 (2)0.2016 (6)0.0197 (11)
C171.1305 (9)0.5485 (3)0.1324 (6)0.0248 (12)
C181.2779 (9)0.5775 (3)0.0349 (7)0.0286 (13)
C191.2694 (8)0.6474 (3)0.0021 (6)0.0220 (11)
C201.1185 (18)0.6885 (5)0.0734 (12)0.019 (2)
C211.1160 (17)0.7642 (5)0.0378 (11)0.0148 (19)
C220.9016 (9)0.8666 (2)0.0186 (6)0.0234 (12)
C230.7809 (8)0.7669 (2)0.1263 (6)0.0248 (12)
N10.8969 (6)0.79253 (18)0.0204 (5)0.0154 (9)
Bi10.70642 (2)0.72364 (2)0.286635 (16)0.01465 (4)
H20.96920.65120.60570.028*
H30.93330.55770.76870.028*
H50.32850.52510.57240.026*
H60.36980.61740.40650.024*
H7A0.67390.42840.72900.039*
H7B0.45860.45600.80010.039*
H7C0.68740.47190.88630.039*
H90.75110.87410.42730.022*
H100.98660.94420.57780.022*
H121.43510.79520.60220.023*
H131.20110.72580.45420.021*
H14A1.36140.91640.81950.036*
H14B1.36620.96910.67900.036*
H14C1.53980.91020.69220.036*
H160.87110.56980.26610.024*
H171.13470.50190.15240.030*
H181.38420.55060.00970.034*
H191.36570.66630.06800.026*
H21A1.19750.78780.12370.018*
H21B1.19040.77210.06000.018*
H22A0.98130.88190.07050.035*
H22B0.97240.88290.11630.035*
H22C0.75410.88370.00860.035*
H23A0.85570.78200.21800.037*
H23B0.63320.78400.13260.037*
H23C0.77820.71800.12410.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.019 (3)0.015 (2)0.015 (3)0.001 (2)0.003 (2)0.000 (2)
C20.019 (3)0.030 (3)0.019 (3)0.007 (2)0.002 (2)0.002 (2)
C30.024 (3)0.028 (3)0.018 (3)0.005 (2)0.002 (2)0.004 (2)
C40.021 (3)0.022 (3)0.018 (3)0.004 (2)0.007 (2)0.001 (2)
C50.018 (3)0.021 (3)0.027 (3)0.006 (2)0.007 (2)0.001 (2)
C60.017 (3)0.019 (3)0.024 (3)0.004 (2)0.001 (2)0.002 (2)
C70.034 (3)0.018 (3)0.026 (3)0.002 (2)0.009 (3)0.002 (2)
C80.020 (3)0.014 (2)0.017 (3)0.0034 (19)0.004 (2)0.0005 (19)
C90.020 (3)0.015 (2)0.019 (3)0.002 (2)0.001 (2)0.001 (2)
C100.027 (3)0.014 (2)0.016 (3)0.001 (2)0.007 (2)0.000 (2)
C110.020 (3)0.016 (2)0.011 (3)0.005 (2)0.002 (2)0.0015 (19)
C120.017 (3)0.021 (3)0.019 (3)0.003 (2)0.001 (2)0.002 (2)
C130.022 (3)0.015 (2)0.016 (3)0.000 (2)0.004 (2)0.0033 (19)
C140.025 (3)0.023 (3)0.024 (3)0.005 (2)0.004 (2)0.006 (2)
C150.013 (2)0.015 (2)0.013 (3)0.0007 (19)0.001 (2)0.0001 (19)
C160.026 (3)0.017 (3)0.015 (3)0.004 (2)0.004 (2)0.002 (2)
C170.031 (3)0.017 (3)0.026 (3)0.003 (2)0.005 (3)0.003 (2)
C180.025 (3)0.031 (3)0.030 (3)0.006 (2)0.001 (3)0.011 (2)
C190.021 (3)0.026 (3)0.019 (3)0.006 (2)0.002 (2)0.002 (2)
C200.017 (4)0.020 (4)0.020 (5)0.000 (3)0.012 (3)0.004 (3)
C210.013 (4)0.017 (4)0.015 (4)0.000 (3)0.007 (3)0.001 (3)
C220.032 (3)0.019 (3)0.019 (3)0.001 (2)0.004 (2)0.006 (2)
C230.027 (3)0.025 (3)0.022 (3)0.004 (2)0.001 (2)0.006 (2)
N10.013 (2)0.016 (2)0.017 (2)0.0011 (16)0.0037 (17)0.0023 (16)
Bi10.01336 (7)0.01541 (7)0.01517 (7)0.0000 (2)0.00051 (5)0.0003 (2)
Geometric parameters (Å, º) top
C1—C61.384 (6)C14—H14A0.9600
C1—C21.394 (6)C14—H14B0.9600
C1—Bi12.291 (5)C14—H14C0.9600
C2—C31.389 (7)C15—C201.391 (12)
C2—H20.9300C15—C161.412 (6)
C3—C41.405 (7)C15—Bi12.267 (5)
C3—H30.9300C16—C171.401 (7)
C4—C51.381 (7)C16—H160.9300
C4—C71.509 (7)C17—C181.370 (7)
C5—C61.394 (7)C17—H170.9300
C5—H50.9300C18—C191.400 (7)
C6—H60.9300C18—H180.9300
C7—H7A0.9600C19—C201.383 (11)
C7—H7B0.9600C19—H190.9300
C7—H7C0.9600C20—C211.515 (7)
C8—C91.386 (6)C21—N11.448 (10)
C8—C131.393 (6)C21—H21A0.9700
C8—Bi12.265 (5)C21—H21B0.9700
C9—C101.397 (6)C22—N11.454 (6)
C9—H90.9300C22—H22A0.9600
C10—C111.397 (6)C22—H22B0.9600
C10—H100.9300C22—H22C0.9600
C11—C121.388 (6)C23—N11.473 (6)
C11—C141.503 (6)C23—H23A0.9600
C12—C131.379 (6)C23—H23B0.9600
C12—H120.9300C23—H23C0.9600
C13—H130.9300N1—Bi12.902 (4)
C6—C1—C2117.3 (4)C20—C15—C16118.7 (6)
C6—C1—Bi1116.8 (3)C20—C15—Bi1122.5 (5)
C2—C1—Bi1125.4 (4)C16—C15—Bi1118.8 (4)
C3—C2—C1121.3 (5)C17—C16—C15120.5 (5)
C3—C2—H2119.4C17—C16—H16119.7
C1—C2—H2119.4C15—C16—H16119.7
C2—C3—C4120.8 (5)C18—C17—C16119.6 (5)
C2—C3—H3119.6C18—C17—H17120.2
C4—C3—H3119.6C16—C17—H17120.2
C5—C4—C3117.9 (5)C17—C18—C19120.3 (5)
C5—C4—C7121.3 (5)C17—C18—H18119.8
C3—C4—C7120.7 (4)C19—C18—H18119.8
C4—C5—C6120.7 (5)C20—C19—C18120.4 (6)
C4—C5—H5119.6C20—C19—H19119.8
C6—C5—H5119.6C18—C19—H19119.8
C1—C6—C5122.0 (4)C19—C20—C15120.4 (8)
C1—C6—H6119.0C19—C20—C21119.1 (11)
C5—C6—H6119.0C15—C20—C21120.5 (10)
C4—C7—H7A109.5N1—C21—C20113.4 (10)
C4—C7—H7B109.5N1—C21—H21A108.9
H7A—C7—H7B109.5C20—C21—H21A108.9
C4—C7—H7C109.5N1—C21—H21B108.9
H7A—C7—H7C109.5C20—C21—H21B108.9
H7B—C7—H7C109.5H21A—C21—H21B107.7
C9—C8—C13117.8 (4)N1—C22—H22A109.5
C9—C8—Bi1119.7 (3)N1—C22—H22B109.5
C13—C8—Bi1122.5 (3)H22A—C22—H22B109.5
C8—C9—C10121.0 (4)N1—C22—H22C109.5
C8—C9—H9119.5H22A—C22—H22C109.5
C10—C9—H9119.5H22B—C22—H22C109.5
C9—C10—C11120.9 (4)N1—C23—H23A109.5
C9—C10—H10119.6N1—C23—H23B109.5
C11—C10—H10119.6H23A—C23—H23B109.5
C12—C11—C10117.4 (4)N1—C23—H23C109.5
C12—C11—C14121.5 (4)H23A—C23—H23C109.5
C10—C11—C14121.0 (4)H23B—C23—H23C109.5
C13—C12—C11121.6 (4)C21—N1—C22111.6 (5)
C13—C12—H12119.2C21—N1—C23110.6 (5)
C11—C12—H12119.2C22—N1—C23110.0 (4)
C12—C13—C8121.3 (4)C21—N1—Bi198.6 (4)
C12—C13—H13119.4C22—N1—Bi1118.9 (3)
C8—C13—H13119.4C23—N1—Bi1106.7 (3)
C11—C14—H14A109.5C1—Bi1—C896.07 (16)
C11—C14—H14B109.5C1—Bi1—C1590.74 (16)
H14A—C14—H14B109.5C1—Bi1—N1157.55 (14)
C11—C14—H14C109.5C8—Bi1—C1594.85 (17)
H14A—C14—H14C109.5C8—Bi1—N181.26 (14)
H14B—C14—H14C109.5C15—Bi1—N167.43 (13)

Experimental details

Crystal data
Chemical formula[Bi(C7H7)2(C9H12N)]
Mr525.43
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)6.0991 (12), 19.630 (4), 8.3699 (16)
β (°) 93.073 (2)
V3)1000.6 (3)
Z2
Radiation typeMo Kα
µ (mm1)8.81
Crystal size (mm)0.20 × 0.08 × 0.01
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.272, 0.917
No. of measured, independent and
observed [I > 2σ(I)] reflections
4908, 3626, 3410
Rint0.016
(sin θ/λ)max1)0.640
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.019, 0.037, 1.00
No. of reflections3626
No. of parameters231
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.86, 0.59
Absolute structureFlack (1983), with 1544 Friedel pairs
Absolute structure parameter0.412 (7)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
C1—Bi12.291 (5)C15—Bi12.267 (5)
C8—Bi12.265 (5)N1—Bi12.902 (4)
C1—Bi1—C896.07 (16)C8—Bi1—C1594.85 (17)
C1—Bi1—C1590.74 (16)C8—Bi1—N181.26 (14)
C1—Bi1—N1157.55 (14)C15—Bi1—N167.43 (13)
 

Footnotes

Also at: Organization for Frontier Research in Preventive Pharmaceutical Sciences, Hokuriku University.

Acknowledgements

This work was supported by a Grant-in Aid for Scientific Research (C) (to JK), and by the `Academic Frontier' Project for Private Universities from the Ministry of Education, Culture, Sports, Science and Technology of Japan (to SY). Financial support was also provided by the Specific Research Fund of Hokuriku University. All are gratefully acknowledged.

References

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