2-(2-Pyrid­yl)pyridinium (2,2′-bipyridine-κ2N,N′)tetra­kis­(nitrato-κ2O,O′)bis­muthate(III)

Meng, Z.-H.; Zhang, S.-S.

doi:10.1107/S160053681103769X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 10| October 2011| Pages m1402-m1403

https://doi.org/10.1107/S160053681103769X

Open

access

2-(2-Pyridyl)pyridinium (2,2′-bipyridine-κ²N,N′)tetrakis(nitrato-κ²O,O′)bismuthate(III)

Zhao-Hui Meng ^a ^* and Shu-Shen Zhang ^a

^aCollege of Chemistry and Pharmacy Engineering, Nanyang Normal University, Nanyang 473061, People's Republic of China
^*Correspondence e-mail: nysymzh@126.com

(Received 10 August 2011; accepted 15 September 2011; online 20 September 2011)

The structure of the title compound, (C₁₀H₉N₂)[Bi(NO₃)₄(C₁₀H₈N₂)], consists of 2-(2-pyridyl)pyridinium cations and anions [Bi(NO₃)₄(C₁₀H₈N₂)]⁻. The Bi³⁺ ion lies on the twofold axis. It is coordinated by two nitrogen atoms from one 2,2′-bipyridine ligand and eight oxygen atoms from four NO₃⁻ anions. The disordered cation is positioned at the inversion centre. The [Bi(NO₃)₄(C₁₀H₈N₂)]⁻ anions and 2-(2-pyridyl)pyridinium cations are connected via N—H⋯O hydrogen bonds into chains. Moreover, these chains are further linked into a two-dimensional layered structure through π–π stacking interactions between bipyridine ligands along the c axis [centroid–centroid distance = 2.868 (4) Å].

Related literature

For potential applications of bismuth(III) coordination compounds in medical chemistry, see: Sun & Szeto (2003 ); Sun et al. (2004 ). For reported bismuth(III) coordination compounds, see: Andrews et al. (2006 ); Boitrel et al. (2003 ); Marsh (2002 ); Wullens et al. (1998 ); Yang et al. (2006 , 2007 ). For the structure of disordered protonated 2,2′-bipyridine, see: Bowmaker et al. (1998 ). For the bond-strength calculations, see: Brown & Altermatt (1985 ); Brese & O'Keeffe (1991 ).

Experimental

Crystal data

(C₁₀H₉N₂)[Bi(NO₃)₄(C₁₀H₈N₂)]
M_r = 770.40
Monoclinic, C 2/c
a = 14.711 (5) Å
b = 10.169 (3) Å
c = 16.832 (5) Å
β = 97.275 (6)°
V = 2497.7 (13) Å³
Z = 4
Mo Kα radiation
μ = 7.14 mm⁻¹
T = 293 K
0.26 × 0.24 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.258, T_max = 0.360
5998 measured reflections
2224 independent reflections
1895 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.084
S = 1.02
2224 reflections
194 parameters
11 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.13 e Å⁻³
Δρ_min = −1.43 e Å⁻³

Table 1
Selected bond lengths (Å)

Bi1—N3	2.444 (5)
Bi1—O5	2.470 (6)
Bi1—O2	2.564 (6)
Bi1—O4	2.626 (6)
Bi1—O1	2.703 (8)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H7⋯O4	0.93	2.31	3.145 (10)	149

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablock global. DOI: https://doi.org/10.1107/S160053681103769X/yk2019sup1.cif

checkCIF report

Comment top

The bismuth (III) coordination compounds have attracted considerable attention in recent years due to their fascinating structural architectures and potential applications in chemical industry, bioengineering, medical chemistry and so on. Up to now, a large number of bismuth (III) coordination compounds with various structural motifs and dimensionalities have been reported. As an expansion of such class of compounds, we have successfully isolated a novel bismuth (III) compound (C₁₀H₉N₂)[Bi(C₁₀H₈N₂)(NO₃)₄] which exhibits a two-dimensional layered structure built up from monoprotonated 2,2-bipyridines and [Bi(C₁₀H₈N₂)(NO₃)₄]^-coordination anions, connected through hydrogen bonds and π–π stacking interactions.

The formula unit of the title compound consists of one coordination anion, [Bi(C₁₀H₈N₂)(NO₃)₄]^-, which has a crystallographic twofold axis symmetry, and one disordered monoprotonated 2,2-bipyridine (Fig. 1). The disordered protonated 2,2-bipyridine in the structure of title compound is similar to that found in the compound (C₁₀H₉N₂)(BiI₄). In the coordination anion, the Bi(III) center is coordinated by two nitrogen atoms from one C₁₀H₈N₂ ligand and eight oxygen atoms from four NO₃^- anions with two Bi—N equal distances of 2.444 (5) Å and Bi—O distances ranging from 2.470 (6) to 2.703 (8) Å. On the basis of bond strength calculations, the bond valence sum (BVS) for Bi1 is 3.30 which suggests that Bi has the +3 oxidation state.

Besides electrostatic interactions, the coordination anions [Bi(C₁₀H₈N₂)(NO₃)₄]^-and protonated 2,2-bipyridines are connected via N—H···O hydrogen bonds [N4—H7···O4, 3.145 (10) Å, 149°] into chains. These chains are further linked into two-dimensional layered structure through the π–π stacking interactions between bipy ligands along the c axis (Fig. 2). Interacting aromatic rings of bipy ligands in these stacks are parallel to each other with the interplanar distance of 2.868 (4) Å.

Related literature top

For potential applications of bismuth(III) coordination compounds in medical chemistry, see: Sun & Szeto (2003); Sun et al. (2004). For reported bismuth(III) coordination compounds, see: Andrews et al. (2006); Boitrel et al. (2003); Marsh (2002); Wullens et al. (1998); Yang et al. (2006, 2007). For [the structure of?] disordered protonated 2,2'-bipyridine, see: Bowmaker et al. (1998). For the bond-strength calculations, see: Brown & Altermatt (1985); Brese & O'Keeffe (1991).

Experimental top

All chemicals were of reagent grade quality obtained from commercial sources and used without further purification. The 10 ml portions of ethanol solutions of C₁₀H₈N₂ (0.16 g, 1 mmol) and 2,6-pyridinedicarboxylic acid (1 mmol, 0.17 g) were mixed, then 12 ml of ethanol solution of Bi(NO₃)₃.5H₂O (0.49 g, 1 mmol) was added. After stirring for half an hour, the solution was filtered and left for slowly evaporation at room temperature to obtain colorless block crystals suitable for X-ray structure determination. Yield: 70% (based on Bi). Anal. calcd. (%) for C₂₀H₁₇BiN₈O₁₂: C, 31.18; H, 2.22; N, 14.55. Found (%): C, 31.26; H, 2.09; N, 14.71.

Structure description top

For potential applications of bismuth(III) coordination compounds in medical chemistry, see: Sun & Szeto (2003); Sun et al. (2004). For reported bismuth(III) coordination compounds, see: Andrews et al. (2006); Boitrel et al. (2003); Marsh (2002); Wullens et al. (1998); Yang et al. (2006, 2007). For [the structure of?] disordered protonated 2,2'-bipyridine, see: Bowmaker et al. (1998). For the bond-strength calculations, see: Brown & Altermatt (1985); Brese & O'Keeffe (1991).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 2008); software used to prepare material for publication: SHELXTL (Bruker, 2008).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 30% probability level (symmetry codes: (i) -x, y, -z + 1/2; (ii) -x, -y, -z).
	Fig. 2. Crystal packing viewed along the c axis. For clarity, H atoms bound to C atoms are omitted, and only H atoms bound to N atoms are shown.

2-(2-Pyridyl)pyridinium (2,2'-bipyridine-κ²N,N')tetrakis(nitrato- κ²O,O')bismuthate(III) top

Crystal data top

(C₁₀H₉N₂)[Bi(NO₃)₄(C₁₀H₈N₂)]	F(000) = 1488
M_r = 770.40	D_x = 2.049 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2470 reflections
a = 14.711 (5) Å	θ = 2.4–22.5°
b = 10.169 (3) Å	µ = 7.14 mm⁻¹
c = 16.832 (5) Å	T = 293 K
β = 97.275 (6)°	Block, colorless
V = 2497.7 (13) Å³	0.26 × 0.24 × 0.18 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2224 independent reflections
Radiation source: fine-focus sealed tube	1895 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 25.1°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→17
T_min = 0.258, T_max = 0.360	k = −12→12
5998 measured reflections	l = −20→17

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0459P)² + 9.2649P] where P = (F_o² + 2F_c²)/3
2224 reflections	(Δ/σ)_max < 0.001
194 parameters	Δρ_max = 1.13 e Å⁻³
11 restraints	Δρ_min = −1.43 e Å⁻³

Crystal data top

(C₁₀H₉N₂)[Bi(NO₃)₄(C₁₀H₈N₂)]	V = 2497.7 (13) Å³
M_r = 770.40	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 14.711 (5) Å	µ = 7.14 mm⁻¹
b = 10.169 (3) Å	T = 293 K
c = 16.832 (5) Å	0.26 × 0.24 × 0.18 mm
β = 97.275 (6)°

Data collection top

Bruker APEXII CCD diffractometer	2224 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	1895 reflections with I > 2σ(I)
T_min = 0.258, T_max = 0.360	R_int = 0.036
5998 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	11 restraints
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 1.13 e Å⁻³
2224 reflections	Δρ_min = −1.43 e Å⁻³
194 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 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Bi1	0.0000	0.43500 (3)	0.2500	0.03845 (15)
C1	−0.1200 (5)	0.6312 (8)	0.3579 (4)	0.0481 (18)
H1	−0.1338	0.5504	0.3794	0.058*
C2	−0.1652 (5)	0.7417 (7)	0.3805 (4)	0.0487 (18)
H2	−0.2072	0.7358	0.4173	0.058*
C3	−0.1466 (5)	0.8595 (7)	0.3475 (4)	0.0508 (19)
H3	−0.1785	0.9348	0.3589	0.061*
C4	−0.0802 (5)	0.8654 (7)	0.2972 (4)	0.0437 (17)
H4	−0.0650	0.9462	0.2767	0.052*
C5	−0.0351 (4)	0.7518 (6)	0.2764 (4)	0.0335 (14)
C6	0.0361 (5)	0.0371 (7)	−0.0162 (4)	0.0473 (18)
C7	0.0484 (6)	0.1654 (8)	0.0057 (4)	0.063 (2)	0.50
H4A	0.0131	0.2045	0.0413	0.075*	0.25
H7	0.0132	0.2045	0.0413	0.075*	0.50
C8	0.1149 (10)	0.2352 (12)	−0.0267 (8)	0.094 (4)
H8	0.100 (6)	0.315 (5)	−0.006 (5)	0.07 (3)*
C9	0.1650 (8)	0.179 (2)	−0.0789 (8)	0.111 (5)
H9	0.2086	0.2271	−0.1017	0.134*
C10	0.1511 (9)	0.0488 (18)	−0.0982 (7)	0.098 (4)
H10	0.162 (10)	0.000 (13)	−0.143 (6)	0.15 (6)*
C11	0.0859 (6)	−0.0230 (9)	−0.0674 (5)	0.067 (2)	0.50
H5	0.0760	−0.1109	−0.0813	0.080*	0.25
H11	0.0760	−0.1109	−0.0813	0.080*	0.50
O1	−0.1017 (5)	0.2143 (8)	0.2235 (4)	0.095 (2)
O2	−0.1374 (4)	0.3450 (6)	0.3126 (4)	0.0784 (19)
O3	−0.2044 (5)	0.1589 (7)	0.2956 (5)	0.101 (2)
O4	−0.0397 (5)	0.3946 (7)	0.0954 (4)	0.0789 (18)
O5	−0.1352 (4)	0.5005 (6)	0.1561 (3)	0.0635 (15)
O6	−0.1767 (5)	0.4407 (7)	0.0349 (4)	0.094 (2)
N1	−0.1488 (5)	0.2376 (7)	0.2795 (5)	0.0631 (19)
N2	−0.1182 (5)	0.4426 (7)	0.0941 (4)	0.0593 (18)
N3	−0.0577 (4)	0.6348 (5)	0.3070 (3)	0.0365 (12)
N4	0.0484 (6)	0.1654 (8)	0.0057 (4)	0.063 (2)	0.50
N5	0.0859 (6)	−0.0230 (9)	−0.0674 (5)	0.067 (2)	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Bi1	0.0478 (2)	0.0270 (2)	0.0448 (2)	0.000	0.02219 (16)	0.000
C1	0.055 (5)	0.047 (4)	0.047 (4)	−0.004 (4)	0.023 (4)	0.000 (4)
C2	0.052 (4)	0.052 (5)	0.046 (4)	0.010 (3)	0.022 (3)	−0.005 (4)
C3	0.061 (5)	0.042 (4)	0.053 (5)	0.017 (4)	0.017 (4)	−0.006 (4)
C4	0.063 (5)	0.026 (4)	0.040 (4)	0.009 (3)	0.002 (3)	0.002 (3)
C5	0.041 (4)	0.029 (3)	0.032 (3)	0.002 (3)	0.012 (3)	−0.005 (3)
C6	0.047 (4)	0.053 (5)	0.040 (4)	0.011 (3)	0.000 (3)	−0.002 (3)
C7	0.076 (5)	0.053 (5)	0.059 (5)	0.000 (4)	0.006 (4)	−0.004 (4)
C8	0.116 (10)	0.066 (8)	0.093 (8)	−0.020 (7)	−0.018 (8)	0.003 (7)
C9	0.062 (7)	0.181 (15)	0.089 (9)	−0.025 (9)	−0.001 (6)	0.065 (10)
C10	0.070 (7)	0.164 (14)	0.062 (7)	0.047 (9)	0.012 (6)	0.023 (9)
C11	0.069 (5)	0.080 (6)	0.052 (4)	0.026 (4)	0.011 (4)	−0.002 (4)
O1	0.096 (2)	0.094 (2)	0.097 (2)	−0.0016 (10)	0.0153 (10)	−0.0016 (10)
O2	0.092 (5)	0.055 (4)	0.097 (5)	−0.028 (3)	0.048 (4)	−0.016 (3)
O3	0.093 (5)	0.064 (4)	0.152 (7)	−0.031 (4)	0.039 (5)	0.020 (4)
O4	0.085 (5)	0.087 (5)	0.071 (4)	−0.001 (4)	0.034 (4)	−0.023 (3)
O5	0.064 (4)	0.073 (4)	0.054 (3)	0.006 (3)	0.008 (3)	−0.015 (3)
O6	0.103 (5)	0.121 (6)	0.053 (4)	−0.031 (4)	−0.009 (4)	−0.013 (4)
N1	0.062 (4)	0.046 (4)	0.087 (5)	−0.007 (3)	0.031 (4)	0.017 (4)
N2	0.071 (5)	0.058 (4)	0.053 (4)	−0.013 (4)	0.021 (4)	−0.010 (4)
N3	0.046 (3)	0.027 (3)	0.039 (3)	0.004 (2)	0.013 (3)	0.001 (2)
N4	0.076 (5)	0.053 (5)	0.059 (5)	0.000 (4)	0.006 (4)	−0.004 (4)
N5	0.069 (5)	0.080 (6)	0.052 (4)	0.026 (4)	0.011 (4)	−0.002 (4)

Geometric parameters (Å, º) top

Bi1—N3	2.444 (5)	C6—C11	1.346 (10)
Bi1—N3ⁱ	2.444 (5)	C6—C7	1.362 (10)
Bi1—O5ⁱ	2.470 (6)	C6—C6ⁱⁱ	1.463 (15)
Bi1—O5	2.470 (6)	C7—C8	1.376 (15)
Bi1—O2	2.564 (6)	C7—H4A	0.9300
Bi1—O2ⁱ	2.564 (6)	C7—H7	0.9300
Bi1—O4	2.626 (6)	C8—C9	1.345 (19)
Bi1—O4ⁱ	2.626 (6)	C8—H8	0.92 (2)
Bi1—O1	2.703 (8)	C9—C10	1.368 (19)
Bi1—O1ⁱ	2.703 (8)	C9—H9	0.9300
C1—N3	1.333 (8)	C10—C11	1.359 (17)
C1—C2	1.383 (10)	C10—H10	0.93 (2)
C1—H1	0.9300	C11—H5	0.9300
C2—C3	1.363 (10)	C11—H11	0.9299
C2—H2	0.9300	O1—N1	1.261 (9)
C3—C4	1.372 (10)	O2—N1	1.228 (8)
C3—H3	0.9300	O3—N1	1.200 (8)
C4—C5	1.399 (9)	O4—N2	1.252 (9)
C4—H4	0.9300	O5—N2	1.250 (8)
C5—N3	1.353 (8)	O6—N2	1.232 (10)
C5—C5ⁱ	1.445 (12)

N3—Bi1—N3ⁱ	67.5 (2)	C3—C2—H2	120.8
N3—Bi1—O5ⁱ	79.4 (2)	C1—C2—H2	120.8
N3ⁱ—Bi1—O5ⁱ	74.64 (18)	C2—C3—C4	119.0 (6)
N3—Bi1—O5	74.64 (18)	C2—C3—H3	120.5
N3ⁱ—Bi1—O5	79.4 (2)	C4—C3—H3	120.5
O5ⁱ—Bi1—O5	148.7 (3)	C3—C4—C5	121.1 (7)
N3—Bi1—O2	78.73 (19)	C3—C4—H4	119.5
N3ⁱ—Bi1—O2	142.1 (2)	C5—C4—H4	119.5
O5ⁱ—Bi1—O2	116.5 (2)	N3—C5—C4	118.9 (6)
O5—Bi1—O2	75.3 (2)	N3—C5—C5ⁱ	117.6 (3)
N3—Bi1—O2ⁱ	142.1 (2)	C4—C5—C5ⁱ	123.5 (4)
N3ⁱ—Bi1—O2ⁱ	78.73 (19)	C11—C6—C7	122.9 (8)
O5ⁱ—Bi1—O2ⁱ	75.3 (2)	C11—C6—C6ⁱⁱ	119.0 (9)
O5—Bi1—O2ⁱ	116.5 (2)	C7—C6—C6ⁱⁱ	118.1 (8)
O2—Bi1—O2ⁱ	138.2 (3)	C6—C7—C8	117.7 (9)
N3—Bi1—O4	118.3 (2)	C6—C7—H4A	121.2
N3ⁱ—Bi1—O4	77.65 (19)	C8—C7—H4A	121.2
O5ⁱ—Bi1—O4	137.4 (2)	C6—C7—H7	121.2
O5—Bi1—O4	49.3 (2)	C8—C7—H7	121.2
O2—Bi1—O4	105.3 (2)	H4A—C7—H7	0.0
O2ⁱ—Bi1—O4	68.0 (2)	C9—C8—C7	120.8 (11)
N3—Bi1—O4ⁱ	77.65 (19)	C9—C8—H8	143 (6)
N3ⁱ—Bi1—O4ⁱ	118.3 (2)	C7—C8—H8	95 (6)
O5ⁱ—Bi1—O4ⁱ	49.3 (2)	C8—C9—C10	119.4 (11)
O5—Bi1—O4ⁱ	137.4 (2)	C8—C9—H9	120.3
O2—Bi1—O4ⁱ	68.0 (2)	C10—C9—H9	120.3
O2ⁱ—Bi1—O4ⁱ	105.3 (2)	C11—C10—C9	121.3 (11)
O4—Bi1—O4ⁱ	162.0 (3)	C11—C10—H10	103 (10)
N3—Bi1—O1	122.9 (2)	C9—C10—H10	132 (10)
N3ⁱ—Bi1—O1	147.0 (2)	C6—C11—C10	117.8 (10)
O5ⁱ—Bi1—O1	135.5 (2)	C6—C11—H5	121.1
O5—Bi1—O1	74.6 (2)	C10—C11—H5	121.1
O2—Bi1—O1	47.4 (2)	C6—C11—H11	121.1
O2ⁱ—Bi1—O1	94.8 (2)	C10—C11—H11	121.1
O4—Bi1—O1	70.0 (2)	H5—C11—H11	0.1
O4ⁱ—Bi1—O1	94.7 (2)	N1—O1—Bi1	93.8 (5)
N3—Bi1—O1ⁱ	147.0 (2)	N1—O2—Bi1	101.6 (5)
N3ⁱ—Bi1—O1ⁱ	122.9 (2)	N2—O4—Bi1	92.6 (4)
O5ⁱ—Bi1—O1ⁱ	74.6 (2)	N2—O5—Bi1	100.2 (5)
O5—Bi1—O1ⁱ	135.5 (2)	O3—N1—O2	123.3 (8)
O2—Bi1—O1ⁱ	94.8 (2)	O3—N1—O1	119.9 (8)
O2ⁱ—Bi1—O1ⁱ	47.4 (2)	O2—N1—O1	116.7 (7)
O4—Bi1—O1ⁱ	94.7 (2)	O6—N2—O5	119.3 (8)
O4ⁱ—Bi1—O1ⁱ	70.0 (2)	O6—N2—O4	123.8 (7)
O1—Bi1—O1ⁱ	67.7 (3)	O5—N2—O4	116.8 (7)
N3—C1—C2	123.2 (7)	C1—N3—C5	119.4 (6)
N3—C1—H1	118.4	C1—N3—Bi1	122.0 (5)
C2—C1—H1	118.4	C5—N3—Bi1	117.8 (4)
C3—C2—C1	118.3 (6)

N3—C1—C2—C3	1.6 (12)	N3ⁱ—Bi1—O5—N2	88.9 (5)
C1—C2—C3—C4	−3.9 (11)	O5ⁱ—Bi1—O5—N2	123.2 (5)
C2—C3—C4—C5	3.3 (11)	O2—Bi1—O5—N2	−119.6 (5)
C3—C4—C5—N3	−0.2 (10)	O2ⁱ—Bi1—O5—N2	17.3 (5)
C3—C4—C5—C5ⁱ	179.7 (8)	O4—Bi1—O5—N2	6.1 (4)
C11—C6—C7—C8	0.1 (12)	O4ⁱ—Bi1—O5—N2	−150.5 (4)
C6ⁱⁱ—C6—C7—C8	−178.4 (9)	O1—Bi1—O5—N2	−70.5 (5)
C6—C7—C8—C9	0.8 (15)	O1ⁱ—Bi1—O5—N2	−37.8 (6)
C7—C8—C9—C10	−1.8 (18)	Bi1—O2—N1—O3	175.6 (7)
C8—C9—C10—C11	2.0 (17)	Bi1—O2—N1—O1	−7.8 (8)
C7—C6—C11—C10	0.0 (12)	Bi1—O1—N1—O3	−176.0 (7)
C6ⁱⁱ—C6—C11—C10	178.5 (9)	Bi1—O1—N1—O2	7.3 (8)
C9—C10—C11—C6	−1.0 (15)	Bi1—O5—N2—O6	172.3 (6)
N3—Bi1—O1—N1	−28.6 (6)	Bi1—O5—N2—O4	−11.0 (8)
N3ⁱ—Bi1—O1—N1	−127.7 (5)	Bi1—O4—N2—O6	−173.2 (7)
O5ⁱ—Bi1—O1—N1	81.7 (6)	Bi1—O4—N2—O5	10.2 (7)
O5—Bi1—O1—N1	−88.2 (5)	C2—C1—N3—C5	1.5 (11)
O2—Bi1—O1—N1	−4.2 (5)	C2—C1—N3—Bi1	−168.7 (6)
O2ⁱ—Bi1—O1—N1	155.6 (5)	C4—C5—N3—C1	−2.2 (10)
O4—Bi1—O1—N1	−140.0 (5)	C5ⁱ—C5—N3—C1	177.9 (7)
O4ⁱ—Bi1—O1—N1	49.8 (5)	C4—C5—N3—Bi1	168.4 (5)
O1ⁱ—Bi1—O1—N1	115.9 (6)	C5ⁱ—C5—N3—Bi1	−11.5 (9)
N3—Bi1—O2—N1	163.7 (6)	N3ⁱ—Bi1—N3—C1	174.4 (7)
N3ⁱ—Bi1—O2—N1	136.6 (5)	O5ⁱ—Bi1—N3—C1	−107.9 (5)
O5ⁱ—Bi1—O2—N1	−124.2 (5)	O5—Bi1—N3—C1	89.8 (6)
O5—Bi1—O2—N1	86.8 (5)	O2—Bi1—N3—C1	12.1 (5)
O2ⁱ—Bi1—O2—N1	−26.7 (5)	O2ⁱ—Bi1—N3—C1	−156.7 (5)
O4—Bi1—O2—N1	47.2 (6)	O4—Bi1—N3—C1	113.5 (5)
O4ⁱ—Bi1—O2—N1	−115.2 (6)	O4ⁱ—Bi1—N3—C1	−57.6 (5)
O1—Bi1—O2—N1	4.4 (5)	O1—Bi1—N3—C1	30.1 (6)
O1ⁱ—Bi1—O2—N1	−49.0 (6)	O1ⁱ—Bi1—N3—C1	−69.4 (7)
N3—Bi1—O4—N2	−36.8 (5)	N3ⁱ—Bi1—N3—C5	4.1 (3)
N3ⁱ—Bi1—O4—N2	−92.6 (5)	O5ⁱ—Bi1—N3—C5	81.7 (5)
O5ⁱ—Bi1—O4—N2	−142.9 (4)	O5—Bi1—N3—C5	−80.6 (5)
O5—Bi1—O4—N2	−6.0 (4)	O2—Bi1—N3—C5	−158.3 (5)
O2—Bi1—O4—N2	48.4 (5)	O2ⁱ—Bi1—N3—C5	33.0 (6)
O2ⁱ—Bi1—O4—N2	−175.3 (5)	O4—Bi1—N3—C5	−56.9 (5)
O4ⁱ—Bi1—O4—N2	113.7 (5)	O4ⁱ—Bi1—N3—C5	132.1 (5)
O1—Bi1—O4—N2	80.5 (5)	O1—Bi1—N3—C5	−140.3 (5)
O1ⁱ—Bi1—O4—N2	144.7 (5)	O1ⁱ—Bi1—N3—C5	120.3 (5)
N3—Bi1—O5—N2	158.3 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H7···O4	0.93	2.31	3.145 (10)	149

Experimental details

Crystal data
Chemical formula	(C₁₀H₉N₂)[Bi(NO₃)₄(C₁₀H₈N₂)]
M_r	770.40
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	14.711 (5), 10.169 (3), 16.832 (5)
β (°)	97.275 (6)
V (Å³)	2497.7 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	7.14
Crystal size (mm)	0.26 × 0.24 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.258, 0.360
No. of measured, independent and observed [I > 2σ(I)] reflections	5998, 2224, 1895
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.084, 1.02
No. of reflections	2224
No. of parameters	194
No. of restraints	11
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.13, −1.43

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Bruker, 2008).

Selected bond lengths (Å) top

Bi1—N3	2.444 (5)	Bi1—O4	2.626 (6)
Bi1—O5	2.470 (6)	Bi1—O1	2.703 (8)
Bi1—O2	2.564 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H7···O4	0.93	2.31	3.145 (10)	149

References

Andrews, P. C., Deacon, G. B., Junk, P. C., Kumar, I. & Silberstein, M. (2006). Dalton Trans. pp. 4852–4858. Web of Science CSD CrossRef Google Scholar
Boitrel, B., Halime, Z., Michaudet, L., Lachkar, M. & Toupet, L. (2003). Chem. Commun. pp. 2670–2671. Web of Science CSD CrossRef Google Scholar
Bowmaker, G. A., Junk, P. C., Lee, A. M., Skelton, B. W. & White, A. H. (1998). Aust. J. Chem. 51, 293–309. Web of Science CSD CrossRef CAS Google Scholar
Brese, N. E. & O'Keeffe, M. (1991). Acta Cryst. B47, 192–197. CrossRef CAS Web of Science IUCr Journals Google Scholar
Brown, I. D. & Altermatt, D. (1985). Acta Cryst. B41, 244–247. CrossRef CAS Web of Science IUCr Journals Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Marsh, R. E. (2002). Acta Cryst. B58, 893–899. CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, H. Z. & Szeto, K. Y. (2003). J. Inorg. Biochem. 94, 114–120. Web of Science CrossRef PubMed CAS Google Scholar
Sun, H. Z., Zhang, L. & Szeto, K. Y. (2004). Met. Ions Biol. Syst. 41, 333–378. PubMed CAS Google Scholar
Wullens, H., Devillers, M., Tinant, B. & Declercq, J.-P. (1998). Acta Cryst. C54, 770–773. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Yang, J.-Y., Fu, Y.-L., Chu, J. & Ng, S. W. (2006). Acta Cryst. E62, m2310–m2312. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yang, N., Tanner, J. A., Wang, Z., Huang, J. D., Zheng, B. J., Zhu, N. Y. & Sun, H. Z. (2007). Chem. Commun. pp. 4413–4415. Web of Science CSD CrossRef Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 10| October 2011| Pages m1402-m1403

https://doi.org/10.1107/S160053681103769X

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)