Bis(but-2-enoato-κO)tri­phenyl­bis­muth(V)

Andreev, P.V.; Somov, N.V.; Kalistratova, O.S.; Gushchin, A.V.; Chuprunov, E.V.

doi:10.1107/S1600536813013317

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page m333

doi:10.1107/S1600536813013317

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Bis(but-2-enoato-κO)triphenylbismuth(V)

Pavel V. Andreev,^a ^* Nikolay V. Somov,^a Olga S. Kalistratova,^b Alexey V. Gushchin ^b and Evgeny V. Chuprunov ^a

^aDepartment of Physics, N. I. Lobachevsky State University of Nizhni Novgorod, 603950, pr. Gagarina, 23-3 Nizhni Novgorod, Russian Federation, and ^bDepartment of Chemistry, N. I. Lobachevsky State University of Nizhni Novgorod, 603950, pr. Gagarina, 23-2 Nizhni Novgorod, Russian Federation
^*Correspondence e-mail: andreev@phys.unn.ru

(Received 30 April 2013; accepted 14 May 2013; online 18 May 2013)

In the title molecule, [Bi(C₆H₅)₃(C₄H₅O₂)₂], the Bi^V atom is in a distorted trigonal–bipyramidal environment with carboxylate O atoms in axial positions and phenyl C atoms in the equatorial plane. The Bi—O bond lengths are 2.283 (3) and 2.309 (2) Å, but as a result of additional long Bi⋯O interactions [2.787 (3) and 2.734 (3) Å], one of the C—Bi—C angles is 148.62 (13)°. In the crystal, weak C—H⋯O hydrogen bonds connect pairs of molecules into inversion dimers. These dimers are further connected by weak C—H⋯π interactions into chains along [100] .

Related literature

For the isotypic (C₆H₅)₃Sb(C₄H₅O₂)₂ structure, see: Gushchin et al. (2013 ). For closely related structures, see: Andreev et al. (2013 ); Belsky (1996 ). For the chemistry of triphenyantimony diacylates, see: Gushchin et al. (2011 ), for their thermodynamic properties, see: Letyanina et al. (2012 ); Markin et al. (2011 ) and for their applications, see: Dodonov & Gushchin (2004 ). For van der Waals radii, see: Batsanov (2001 ).

Experimental

Crystal data

[Bi(C₆H₅)₃(C₄H₅O₂)₂]
M_r = 610.44
Triclinic, $[P \overline 1]$
a = 10.4710 (3) Å
b = 10.4957 (3) Å
c = 11.9774 (3) Å
α = 84.941 (2)°
β = 83.633 (2)°
γ = 69.084 (3)°
V = 1220.32 (6) Å³
Z = 2
Mo Kα radiation
μ = 7.25 mm⁻¹
T = 293 K
0.09 mm (radius)

Data collection

Agilent Xcalibur (Sapphire3, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.810, T_max = 1
17262 measured reflections
4946 independent reflections
4620 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.050
S = 1.11
4946 reflections
280 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.84 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2Aⁱ	0.93	2.53	3.450 (6)	171
C4B—H4B1⋯C1Aⁱⁱ	0.96	2.74	3.683 (6)	167
C4B—H4B1⋯C2Aⁱⁱ	0.96	2.85	3.613 (7)	137
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813013317/lh5612sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013317/lh5612Isup2.hkl

checkCIF report

Comment top

Bis(but-2-enoate) triphenylbismuth C₂₆H₂₅O₄Bi belongs to the family of triphenylbismuth diacylates. Compounds of triphenylbismuth and triphenylantimony diacylates contain two double bonds C═C in the molecule, due to which they can be used for polymerization filling of polystyrene and polymethylmethacrylate. The title compound is a very promising monomer for developing metal-containing organic scintillators which have recently attracted much attention in high-energy physics. It was found that the participation of both acrylate groups in polymerization leads to cross-linking, considerably decreasing the thermooxidative destruction of the resulting polymer (Dodonov et al., 2004). Organic glasses based on triphenylantimony diacrylate and methylmethacrylate having increased fungal resistance are now available (Dodonov et al., 2004). The thermodynamic properties of triphenylantimony diacylates have been studied (Letyanina et al., 2012; Markin et al., 2011). The crystal structure and chemistry of a similar orgaonmetallic compound of antimony has been reported by Gushchin et al. (2013).

In the molecule of title compound the O—Bi—O angle is 172.64 (9)° and the C_phenyl—Bi—C_phenyl angles are 148.62 (13)°, 106.20 (13)°, 150.10 (13)°. Such a deviation for the latter from the ideal 120° is typical for triphenylantomony diacylates because of additional long Bi···O interactions. A similar geometries were observed in triphenylantomony diacylates (Gushchin et al., 2011; Gushchin et al., 2013; Andreev et al., 2013). The Bi–O2A and Bi–O2B distances are 2.787 (3) Å and 2.734 (3) Å, respectively and are significantly shorter than the sum of the van der Waals radii of these atoms (3.85 Å) (Batsanov, 2001). A similar interaction was observed in triphenylantimony dimetacrylate (Gushchin et al., 2011), bis[(E)-3-(4-methoxyphenyl)prop-2-enoato]triphenylantimony(V) (Andreev et al., 2013), triphenylantimony dicrotonate (Gushchin et al., 2013) and triphenylantimony-bis(cinnamate) (Belsky, 1996). In the crystal, weak C—H···O hydrogen bonds connect pairs of molecules into inversion dimers. These dimers are further connected by weak C—H···π interactions into chains along [100] (see Fig.2).

Related literature top

For the isotypic (C₆H₅)₃Sb(C₄H₅O₂)₂ structure, see: Gushchin et al. (2013). For closely related structures, see: Andreev et al. (2013); Belsky (1996). For the chemistry of triphenyantimony diacylates, see: Gushchin et al. (2011), for their thermodynamic properties, see: Letyanina et al. (2012); Markin et al. (2011) and for their applications, see: Dodonov & Gushchin (2004). For van der Waals radii, see: Batsanov (2001).

Experimental top

The synthesis was carried out on the oxidation addition reaction of triphenylbismuth, crotonic acid and tert-butyl hydroperoxide. To a solution of 0.56 ml of 92.6% aqueous tert-butyl hydroperoxide and 0.86 g of crotonic acid in 20 ml of diethyl ether was added a solution of 2.2 g of triphenylbismuth. The mixture was kept for 24 h at room temperature. The yellow crystals formed were filtered off and dried to obtain 1.91 g (73%) of triphenylbismuth bis(but-2-enoate). The product was recrystallized twice from chloroform-hexane mixture (1:4), m.p. 426 K. A crystal for X-ray diffraction analysis was obtained from benzene solution.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis RED (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. Part of the crystal structure with weak C—H···O and C—H···π interactions shown as dashed lines connecting moleclues along [100].

Bis(but-2-enoato-κO)triphenylbismuth(V) top

Crystal data top

[Bi(C₆H₅)₃(C₄H₅O₂)₂]	Z = 2
M_r = 610.44	F(000) = 592
Triclinic, P1	D_x = 1.661 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4710 (3) Å	Cell parameters from 9953 reflections
b = 10.4957 (3) Å	θ = 3.4–32.8°
c = 11.9774 (3) Å	µ = 7.25 mm⁻¹
α = 84.941 (2)°	T = 293 K
β = 83.633 (2)°	Sphere, colourless
γ = 69.084 (3)°	0.09 mm (radius)
V = 1220.32 (6) Å³

Data collection top

Agilent Xcalibur (Sapphire3, Gemini) diffractometer	4946 independent reflections
Graphite monochromator	4620 reflections with I > 2σ(I)
Detector resolution: 16.0302 pixels mm^-1	R_int = 0.024
ω scans	θ_max = 26.4°, θ_min = 3.4°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −13→13
T_min = 0.810, T_max = 1	k = −13→13
17262 measured reflections	l = −14→14

Refinement top

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.050	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0212P)² + 0.9058P] where P = (F_o² + 2F_c²)/3
4946 reflections	(Δ/σ)_max = 0.001
280 parameters	Δρ_max = 0.65 e Å⁻³
2 restraints	Δρ_min = −0.84 e Å⁻³

Crystal data top

[Bi(C₆H₅)₃(C₄H₅O₂)₂]	γ = 69.084 (3)°
M_r = 610.44	V = 1220.32 (6) Å³
Triclinic, P1	Z = 2
a = 10.4710 (3) Å	Mo Kα radiation
b = 10.4957 (3) Å	µ = 7.25 mm⁻¹
c = 11.9774 (3) Å	T = 293 K
α = 84.941 (2)°	0.09 mm (radius)
β = 83.633 (2)°

Data collection top

Agilent Xcalibur (Sapphire3, Gemini) diffractometer	4946 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	4620 reflections with I > 2σ(I)
T_min = 0.810, T_max = 1	R_int = 0.024
17262 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	2 restraints
wR(F²) = 0.050	H-atom parameters constrained
S = 1.11	Δρ_max = 0.65 e Å⁻³
4946 reflections	Δρ_min = −0.84 e Å⁻³
280 parameters

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 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
Bi	0.714269 (12)	0.636573 (11)	0.737494 (10)	0.03886 (5)
O1A	0.4935 (3)	0.6470 (3)	0.7972 (2)	0.0561 (7)
O1B	0.9413 (3)	0.5981 (3)	0.6880 (2)	0.0595 (7)
O2A	0.4728 (3)	0.8624 (3)	0.7607 (2)	0.0574 (7)
O2B	0.8411 (3)	0.8212 (3)	0.6718 (2)	0.0552 (6)
C1	0.6556 (3)	0.6872 (3)	0.5635 (3)	0.0416 (7)
C2	0.6338 (4)	0.8145 (4)	0.5113 (3)	0.0564 (9)
H2	0.6465	0.8833	0.5476	0.068*
C1A	0.4227 (4)	0.7768 (4)	0.7950 (3)	0.0479 (8)
C1B	0.9455 (4)	0.7179 (4)	0.6631 (3)	0.0485 (8)
C3	0.5922 (5)	0.8372 (5)	0.4026 (4)	0.0679 (12)
H3	0.5777	0.922	0.3652	0.082*
C2A	0.2745 (4)	0.8208 (5)	0.8375 (3)	0.0598 (10)
H2A	0.2218	0.9128	0.8278	0.072*
C2B	1.0828 (4)	0.7244 (5)	0.6218 (4)	0.0641 (11)
H2B	1.1585	0.644	0.6247	0.077*
C4	0.5722 (4)	0.7356 (5)	0.3504 (3)	0.0663 (12)
H4	0.5431	0.7525	0.2782	0.08*
C3A	0.2156 (5)	0.7417 (6)	0.8858 (4)	0.0697 (12)
H3A	0.2683	0.6494	0.8926	0.084*
C3B	1.1031 (4)	0.8329 (5)	0.5829 (3)	0.0617 (11)
H3B	1.0262	0.9124	0.5813	0.074*
C5	0.5947 (5)	0.6103 (5)	0.4032 (4)	0.0650 (11)
H5	0.5815	0.5421	0.3664	0.078*
C4A	0.0675 (5)	0.7837 (6)	0.9334 (4)	0.0850 (16)
H4A1	0.0634	0.753	1.0111	0.127*
H4A2	0.0192	0.7435	0.8922	0.127*
H4A3	0.0258	0.8814	0.927	0.127*
C4B	1.2384 (5)	0.8463 (6)	0.5391 (4)	0.0845 (16)
H4B3	1.2241	0.9396	0.5143	0.127*
H4B2	1.2778	0.7886	0.477	0.127*
H4B1	1.2995	0.8194	0.5979	0.127*
C6	0.6372 (4)	0.5830 (4)	0.5115 (3)	0.0553 (9)
H6	0.6529	0.4975	0.5478	0.066*
C7	0.7323 (3)	0.7074 (4)	0.9006 (3)	0.0424 (7)
C8	0.7989 (5)	0.6056 (5)	0.9773 (3)	0.0664 (11)
H8	0.8324	0.5141	0.9602	0.08*
C9	0.8137 (6)	0.6466 (7)	1.0826 (4)	0.0850 (16)
H9	0.8588	0.5815	1.1364	0.102*
C10	0.7615 (6)	0.7831 (7)	1.1063 (4)	0.0817 (16)
H10	0.7706	0.8091	1.1764	0.098*
C11	0.6975 (5)	0.8790 (6)	1.0283 (5)	0.0787 (14)
H11	0.6639	0.9705	1.0452	0.094*
C12	0.6811 (4)	0.8437 (4)	0.9245 (4)	0.0620 (11)
H12	0.6365	0.9102	0.8714	0.074*
C13	0.7740 (5)	0.4106 (4)	0.7598 (3)	0.0580 (11)
C14	0.8981 (6)	0.3282 (4)	0.7091 (4)	0.0794 (15)
H14	0.9579	0.367	0.6695	0.095*
C15	0.9322 (8)	0.1884 (5)	0.7176 (6)	0.105 (2)
H15	1.0151	0.1318	0.684	0.126*
C16	0.8411 (10)	0.1335 (6)	0.7771 (6)	0.121 (3)
H16	0.8641	0.0391	0.7828	0.145*
C17	0.7176 (8)	0.2141 (6)	0.8281 (6)	0.105 (2)
H17	0.6576	0.1751	0.8671	0.126*
C18	0.6848 (6)	0.3539 (5)	0.8202 (4)	0.0782 (15)
H18	0.6027	0.4101	0.8553	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Bi	0.04616 (8)	0.02998 (7)	0.04346 (8)	−0.01683 (5)	−0.00534 (5)	−0.00091 (5)
O1A	0.0565 (16)	0.0633 (17)	0.0606 (16)	−0.0385 (14)	−0.0047 (12)	0.0079 (13)
O1B	0.0508 (15)	0.0522 (16)	0.0720 (18)	−0.0142 (12)	0.0046 (13)	−0.0134 (14)
O2A	0.0568 (16)	0.0524 (16)	0.0637 (17)	−0.0219 (13)	−0.0041 (13)	0.0029 (13)
O2B	0.0543 (16)	0.0501 (15)	0.0643 (17)	−0.0235 (13)	−0.0009 (12)	−0.0026 (12)
C1	0.0444 (18)	0.0370 (17)	0.0413 (18)	−0.0136 (14)	−0.0008 (14)	0.0014 (14)
C2	0.064 (2)	0.046 (2)	0.060 (2)	−0.0233 (18)	−0.0027 (19)	0.0064 (18)
C1A	0.0438 (19)	0.059 (2)	0.0399 (18)	−0.0153 (17)	−0.0087 (15)	−0.0013 (16)
C1B	0.0429 (19)	0.056 (2)	0.0445 (19)	−0.0155 (17)	0.0027 (15)	−0.0108 (16)
C3	0.072 (3)	0.067 (3)	0.057 (3)	−0.021 (2)	−0.004 (2)	0.024 (2)
C2A	0.057 (2)	0.067 (3)	0.056 (2)	−0.021 (2)	−0.0122 (18)	0.003 (2)
C2B	0.045 (2)	0.067 (3)	0.078 (3)	−0.0170 (19)	0.005 (2)	−0.012 (2)
C4	0.057 (2)	0.096 (4)	0.043 (2)	−0.025 (2)	−0.0034 (18)	0.007 (2)
C3A	0.064 (3)	0.092 (3)	0.062 (3)	−0.039 (3)	−0.013 (2)	0.010 (2)
C3B	0.057 (2)	0.087 (3)	0.049 (2)	−0.036 (2)	−0.0039 (18)	0.000 (2)
C5	0.068 (3)	0.078 (3)	0.054 (2)	−0.029 (2)	−0.008 (2)	−0.011 (2)
C4A	0.052 (3)	0.129 (5)	0.078 (3)	−0.042 (3)	0.000 (2)	0.008 (3)
C4B	0.066 (3)	0.133 (5)	0.070 (3)	−0.059 (3)	0.000 (2)	0.005 (3)
C6	0.069 (3)	0.048 (2)	0.053 (2)	−0.0231 (19)	−0.0108 (19)	−0.0015 (17)
C7	0.0435 (18)	0.0462 (19)	0.0433 (18)	−0.0229 (15)	0.0007 (14)	−0.0077 (15)
C8	0.094 (3)	0.063 (3)	0.051 (2)	−0.040 (2)	−0.007 (2)	0.003 (2)
C9	0.116 (4)	0.119 (4)	0.043 (2)	−0.070 (4)	−0.014 (2)	0.011 (3)
C10	0.097 (4)	0.124 (4)	0.050 (3)	−0.071 (4)	0.021 (3)	−0.036 (3)
C11	0.068 (3)	0.089 (4)	0.086 (4)	−0.030 (3)	0.005 (3)	−0.049 (3)
C12	0.056 (2)	0.056 (2)	0.078 (3)	−0.0197 (19)	−0.006 (2)	−0.025 (2)
C13	0.092 (3)	0.0321 (18)	0.056 (2)	−0.0221 (19)	−0.034 (2)	0.0034 (16)
C14	0.111 (4)	0.039 (2)	0.081 (3)	−0.010 (2)	−0.031 (3)	−0.011 (2)
C15	0.156 (6)	0.042 (3)	0.106 (4)	−0.007 (3)	−0.048 (4)	−0.014 (3)
C16	0.206 (8)	0.043 (3)	0.126 (5)	−0.036 (4)	−0.104 (5)	0.017 (3)
C17	0.172 (6)	0.055 (3)	0.114 (5)	−0.061 (4)	−0.079 (4)	0.034 (3)
C18	0.117 (4)	0.049 (2)	0.085 (3)	−0.044 (3)	−0.043 (3)	0.022 (2)

Geometric parameters (Å, º) top

Bi—C7	2.201 (3)	C5—H5	0.93
Bi—C1	2.205 (3)	C4A—H4A1	0.96
Bi—C13	2.226 (4)	C4A—H4A2	0.96
Bi—O1B	2.283 (3)	C4A—H4A3	0.96
Bi—O1A	2.309 (2)	C4B—H4B3	0.96
Bi—O2A	2.787 (3)	C4B—H4B2	0.96
Bi—O2B	2.734 (3)	C4B—H4B1	0.96
O1A—C1A	1.297 (5)	C6—H6	0.93
O1B—C1B	1.281 (5)	C7—C12	1.380 (5)
O2A—C1A	1.215 (4)	C7—C8	1.382 (6)
O2B—C1B	1.237 (4)	C8—C9	1.409 (6)
C1—C2	1.376 (5)	C8—H8	0.93
C1—C6	1.385 (5)	C9—C10	1.381 (8)
C2—C3	1.392 (6)	C9—H9	0.93
C2—H2	0.93	C10—C11	1.352 (8)
C1A—C2A	1.495 (5)	C10—H10	0.93
C1B—C2B	1.491 (5)	C11—C12	1.373 (6)
C3—C4	1.369 (7)	C11—H11	0.93
C3—H3	0.93	C12—H12	0.93
C2A—C3A	1.268 (6)	C13—C14	1.386 (7)
C2A—H2A	0.93	C13—C18	1.386 (6)
C2B—C3B	1.271 (6)	C14—C15	1.377 (7)
C2B—H2B	0.93	C14—H14	0.93
C4—C5	1.360 (6)	C15—C16	1.385 (10)
C4—H4	0.93	C15—H15	0.93
C3A—C4A	1.511 (6)	C16—C17	1.377 (11)
C3A—H3A	0.93	C16—H16	0.93
C3B—C4B	1.506 (6)	C17—C18	1.380 (7)
C3B—H3B	0.93	C17—H17	0.93
C5—C6	1.391 (6)	C18—H18	0.93

C7—Bi—C1	148.62 (13)	C3A—C4A—H4A1	109.5
C7—Bi—C13	106.20 (13)	C3A—C4A—H4A2	109.5
C1—Bi—C13	105.10 (13)	H4A1—C4A—H4A2	109.5
C7—Bi—O1B	90.15 (11)	C3A—C4A—H4A3	109.5
C1—Bi—O1B	94.14 (11)	H4A1—C4A—H4A3	109.5
C13—Bi—O1B	86.30 (14)	H4A2—C4A—H4A3	109.5
C7—Bi—O1A	89.80 (11)	C3B—C4B—H4B3	109.5
C1—Bi—O1A	89.73 (11)	C3B—C4B—H4B2	109.5
C13—Bi—O1A	86.65 (14)	H4B3—C4B—H4B2	109.5
O1B—Bi—O1A	172.64 (9)	C3B—C4B—H4B1	109.5
C7—Bi—O2B	78.59 (10)	H4B3—C4B—H4B1	109.5
C1—Bi—O2B	80.12 (11)	H4B2—C4B—H4B1	109.5
C13—Bi—O2B	137.31 (14)	C1—C6—C5	117.9 (4)
O1B—Bi—O2B	51.02 (9)	C1—C6—H6	121
O1A—Bi—O2B	136.05 (9)	C5—C6—H6	121
C1A—O1A—Bi	104.0 (2)	C12—C7—C8	122.4 (4)
C1B—O1B—Bi	103.8 (2)	C12—C7—Bi	122.4 (3)
C1B—O2B—Bi	83.6 (2)	C8—C7—Bi	115.1 (3)
C2—C1—C6	122.2 (3)	C7—C8—C9	117.0 (5)
C2—C1—Bi	122.7 (3)	C7—C8—H8	121.5
C6—C1—Bi	115.1 (2)	C9—C8—H8	121.5
C1—C2—C3	118.0 (4)	C10—C9—C8	120.4 (5)
C1—C2—H2	121	C10—C9—H9	119.8
C3—C2—H2	121	C8—C9—H9	119.8
O2A—C1A—O1A	122.4 (3)	C11—C10—C9	120.4 (4)
O2A—C1A—C2A	119.5 (4)	C11—C10—H10	119.8
O1A—C1A—C2A	118.1 (3)	C9—C10—H10	119.8
O2B—C1B—O1B	121.6 (3)	C10—C11—C12	121.2 (5)
O2B—C1B—C2B	122.4 (4)	C10—C11—H11	119.4
O1B—C1B—C2B	115.9 (3)	C12—C11—H11	119.4
C4—C3—C2	120.5 (4)	C11—C12—C7	118.6 (5)
C4—C3—H3	119.7	C11—C12—H12	120.7
C2—C3—H3	119.7	C7—C12—H12	120.7
C3A—C2A—C1A	124.7 (4)	C14—C13—C18	120.7 (4)
C3A—C2A—H2A	117.6	C14—C13—Bi	119.4 (3)
C1A—C2A—H2A	117.6	C18—C13—Bi	119.9 (3)
C3B—C2B—C1B	124.2 (4)	C15—C14—C13	119.6 (6)
C3B—C2B—H2B	117.9	C15—C14—H14	120.2
C1B—C2B—H2B	117.9	C13—C14—H14	120.2
C5—C4—C3	120.6 (4)	C14—C15—C16	119.0 (7)
C5—C4—H4	119.7	C14—C15—H15	120.5
C3—C4—H4	119.7	C16—C15—H15	120.5
C2A—C3A—C4A	126.0 (5)	C17—C16—C15	122.1 (5)
C2A—C3A—H3A	117	C17—C16—H16	118.9
C4A—C3A—H3A	117	C15—C16—H16	118.9
C2B—C3B—C4B	126.8 (5)	C16—C17—C18	118.6 (7)
C2B—C3B—H3B	116.6	C16—C17—H17	120.7
C4B—C3B—H3B	116.6	C18—C17—H17	120.7
C4—C5—C6	120.7 (4)	C17—C18—C13	120.0 (6)
C4—C5—H5	119.6	C17—C18—H18	120
C6—C5—H5	119.6	C13—C18—H18	120

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2Aⁱ	0.93	2.53	3.450 (6)	171
C4B—H4B1···C1Aⁱⁱ	0.96	2.74	3.683 (6)	167
C4B—H4B1···C2Aⁱⁱ	0.96	2.85	3.613 (7)	137

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[Bi(C₆H₅)₃(C₄H₅O₂)₂]
M_r	610.44
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.4710 (3), 10.4957 (3), 11.9774 (3)
α, β, γ (°)	84.941 (2), 83.633 (2), 69.084 (3)
V (Å³)	1220.32 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	7.25
Crystal size (mm)	0.09 (radius)

Data collection
Diffractometer	Agilent Xcalibur (Sapphire3, Gemini) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.810, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	17262, 4946, 4620
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.050, 1.11
No. of reflections	4946
No. of parameters	280
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.84

Computer programs: CrysAlis PRO (Agilent, 2011), CrysAlis RED (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2Aⁱ	0.93	2.53	3.450 (6)	171
C4B—H4B1···C1Aⁱⁱ	0.96	2.74	3.683 (6)	167.0
C4B—H4B1···C2Aⁱⁱ	0.96	2.85	3.613 (7)	136.7

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1, y, z.

Acknowledgements

The work was supported financially by the Ministry of Education and Science of the Russian Federation, project 14.B37.21.1158.

References

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