A bis­[penta­iodo­bismuthate(III)] salt of 4-hydroxy­pyridinium

The crystal structure of tetra(4-hydroxy­pyridinium) di-μ-iodo-bis­[tetra­iodo­bismuthate(III)] 4-pyridone tetrasolvate, (C₅H₆NO)₄[Bi₂I₁₀]·4C₅H₅NO, has been determined. The structure contains discrete centrosymmetric [Bi₂I₁₀]⁴⁻ anions enclosed in a hydrogen-bonded array of 4-hydroxy­pyridinium cations and 4-pyridone mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.018 Å
• R factor = 0.046
• wR factor = 0.102
• Data-to-parameter ratio = 22.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_728  Alert C D-H..A  Calc      142.81, Rep      144.00, Dev.      1.19 Deg.
                     N4   -H4A  -I2      1.555   1.555   2.567


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

tetra(4-hydroxypyridinium) bis((µ₂-iodo)tetraiodobismuthate(III)) 4-pyridone tetrasolvate

Crystal data

(C5H6NO)4[Bi2I10]·4C5H5NO	Z = 1
Mr = 2451.80	F(000) = 1100
Triclinic, P1	Dx = 2.646 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.366 (3) Å	Cell parameters from 5958 reflections
b = 12.362 (3) Å	θ = 2–25°
c = 13.504 (5) Å	µ = 10.78 mm^−1
α = 116.212 (13)°	T = 173 K
β = 95.05 (2)°	Lath, red
γ = 92.914 (16)°	0.15 × 0.05 × 0.02 mm
V = 1538.6 (8) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	6960 independent reflections
Radiation source: fine-focus sealed tube	4015 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
ω scans with 0.3° frames	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.440, Tmax = 0.810	k = −16→16
15998 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 0.90	w = 1/[σ^2(Fo^2) + (0.0377P)^2] where P = (Fo^2 + 2Fc^2)/3
6960 reflections	(Δ/σ)max = 0.001
307 parameters	Δρmax = 1.87 e Å^−3
0 restraints	Δρmin = −2.67 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Bi1	0.53154 (5)	0.58465 (4)	0.69033 (4)	0.02469 (12)
I1	0.53293 (9)	0.47302 (8)	0.84481 (7)	0.0426 (2)
I2	0.23164 (8)	0.57258 (7)	0.69094 (6)	0.03209 (19)
I3	0.57605 (8)	0.84204 (7)	0.86969 (6)	0.0377 (2)
I4	0.82569 (8)	0.58151 (7)	0.69141 (6)	0.03154 (19)
I5	0.50680 (8)	0.68685 (6)	0.50912 (6)	0.02954 (19)
N1	0.3262 (11)	0.8174 (10)	1.1491 (9)	0.047 (3)
H1A	0.2549	0.7852	1.1018	0.057*
N2	0.9281 (10)	1.1400 (8)	1.1014 (7)	0.035 (2)
H2A	0.9411	1.1776	1.0605	0.042*
N3	1.0039 (12)	0.7018 (8)	1.5359 (7)	0.042 (3)
H3A	0.9945	0.6597	1.5734	0.050*
N4	−0.1625 (11)	0.5816 (9)	1.1423 (8)	0.040 (3)
H4A	−0.2176	0.5483	1.1693	0.049*
O1	0.6488 (9)	0.9703 (8)	1.3745 (7)	0.054 (3)
H1	0.7164	0.9555	1.3428	0.081*
O2	0.8628 (8)	0.9674 (7)	1.2917 (7)	0.038 (2)
O3	1.0549 (8)	0.9018 (7)	1.3715 (7)	0.042 (2)
H3	0.9837	0.9229	1.3548	0.063*
O4	0.0948 (8)	0.7446 (7)	1.0290 (6)	0.040 (2)
C1	0.4414 (13)	0.8066 (11)	1.1124 (11)	0.041 (3)
H1B	0.4468	0.7659	1.0347	0.050*
C2	0.5537 (13)	0.8542 (11)	1.1862 (11)	0.043 (3)
H2B	0.6365	0.8429	1.1600	0.051*
C3	0.5447 (13)	0.9189 (11)	1.2993 (11)	0.040 (3)
C4	0.4227 (13)	0.9296 (13)	1.3361 (11)	0.048 (3)
H4B	0.4130	0.9720	1.4128	0.058*
C5	0.3184 (13)	0.8769 (12)	1.2575 (11)	0.049 (4)
H5A	0.2345	0.8828	1.2814	0.058*
C6	1.0309 (13)	1.0989 (10)	1.1419 (10)	0.037 (3)
H6A	1.1162	1.1102	1.1252	0.045*
C7	1.0097 (12)	1.0423 (10)	1.2059 (9)	0.036 (3)
H7A	1.0812	1.0157	1.2351	0.043*
C8	0.8838 (12)	1.0222 (9)	1.2299 (9)	0.028 (3)
C9	0.7810 (13)	1.0674 (10)	1.1878 (11)	0.044 (3)
H9A	0.6947	1.0589	1.2039	0.053*
C10	0.8078 (12)	1.1223 (10)	1.1248 (10)	0.035 (3)
H10A	0.7380	1.1503	1.0950	0.042*
C11	1.1226 (14)	0.7230 (11)	1.5131 (11)	0.045 (3)
H11A	1.1948	0.6913	1.5357	0.054*
C12	1.1394 (12)	0.7899 (10)	1.4574 (9)	0.035 (3)
H12A	1.2240	0.8063	1.4422	0.042*
C13	1.0347 (13)	0.8343 (10)	1.4226 (9)	0.033 (3)
C14	0.9087 (12)	0.8083 (10)	1.4466 (9)	0.037 (3)
H14A	0.8342	0.8366	1.4230	0.045*
C15	0.8980 (13)	0.7425 (10)	1.5039 (9)	0.037 (3)
H15A	0.8152	0.7249	1.5215	0.044*
C16	−0.0347 (13)	0.5774 (10)	1.1645 (9)	0.032 (3)
H16A	−0.0061	0.5363	1.2063	0.038*
C17	0.0542 (13)	0.6312 (9)	1.1281 (9)	0.035 (3)
H17A	0.1445	0.6292	1.1461	0.042*
C18	0.0128 (12)	0.6913 (10)	1.0624 (9)	0.031 (3)
C19	−0.1247 (12)	0.6886 (10)	1.0416 (9)	0.035 (3)
H19A	−0.1584	0.7265	0.9985	0.042*
C20	−0.2099 (13)	0.6342 (11)	1.0807 (10)	0.042 (3)
H20A	−0.3011	0.6335	1.0648	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Bi1	0.0272 (3)	0.0326 (2)	0.0210 (2)	0.00192 (18)	0.00394 (17)	0.01794 (18)
I1	0.0417 (5)	0.0670 (6)	0.0400 (5)	−0.0010 (4)	0.0018 (4)	0.0440 (5)
I2	0.0284 (5)	0.0421 (5)	0.0375 (5)	0.0027 (4)	0.0057 (3)	0.0282 (4)
I3	0.0383 (5)	0.0376 (5)	0.0320 (4)	0.0016 (4)	0.0069 (4)	0.0106 (4)
I4	0.0268 (5)	0.0403 (5)	0.0348 (4)	0.0038 (3)	0.0049 (3)	0.0232 (4)
I5	0.0362 (5)	0.0327 (4)	0.0272 (4)	0.0036 (3)	0.0036 (3)	0.0202 (3)
N1	0.042 (7)	0.070 (8)	0.042 (7)	0.013 (6)	0.014 (5)	0.033 (6)
N2	0.046 (7)	0.029 (5)	0.028 (5)	−0.001 (5)	−0.002 (5)	0.014 (4)
N3	0.074 (9)	0.038 (6)	0.026 (6)	0.003 (6)	0.017 (6)	0.025 (5)
N4	0.057 (8)	0.046 (6)	0.031 (6)	0.003 (6)	0.012 (5)	0.027 (5)
O1	0.038 (6)	0.085 (7)	0.053 (6)	0.003 (5)	0.010 (5)	0.043 (6)
O2	0.042 (5)	0.040 (5)	0.042 (5)	0.005 (4)	0.004 (4)	0.027 (4)
O3	0.038 (6)	0.051 (5)	0.052 (6)	0.004 (4)	0.009 (4)	0.036 (5)
O4	0.037 (5)	0.057 (6)	0.041 (5)	−0.007 (4)	0.002 (4)	0.037 (5)
C1	0.045 (9)	0.037 (7)	0.045 (8)	−0.007 (6)	0.012 (7)	0.020 (6)
C2	0.035 (8)	0.047 (8)	0.054 (9)	0.007 (6)	0.014 (7)	0.027 (7)
C3	0.033 (8)	0.047 (8)	0.041 (8)	0.000 (6)	−0.005 (6)	0.024 (6)
C4	0.029 (8)	0.083 (10)	0.044 (8)	0.003 (7)	0.009 (6)	0.039 (8)
C5	0.039 (9)	0.072 (10)	0.050 (9)	0.007 (7)	0.015 (7)	0.039 (8)
C6	0.046 (9)	0.038 (7)	0.039 (7)	0.002 (6)	0.021 (6)	0.024 (6)
C7	0.038 (8)	0.043 (7)	0.025 (6)	0.013 (6)	0.004 (6)	0.012 (6)
C8	0.039 (8)	0.026 (6)	0.021 (6)	0.001 (5)	0.004 (5)	0.010 (5)
C9	0.049 (9)	0.037 (7)	0.061 (9)	0.002 (6)	0.008 (7)	0.035 (7)
C10	0.023 (7)	0.036 (7)	0.054 (8)	−0.001 (5)	−0.007 (6)	0.030 (6)
C11	0.047 (9)	0.042 (8)	0.050 (9)	0.009 (7)	0.003 (7)	0.022 (7)
C12	0.033 (8)	0.045 (7)	0.041 (7)	0.007 (6)	0.012 (6)	0.029 (6)
C13	0.050 (9)	0.034 (7)	0.023 (6)	0.006 (6)	0.014 (6)	0.017 (5)
C14	0.036 (8)	0.042 (7)	0.034 (7)	0.006 (6)	0.003 (6)	0.017 (6)
C15	0.040 (8)	0.038 (7)	0.027 (6)	−0.005 (6)	0.006 (6)	0.011 (6)
C16	0.047 (8)	0.036 (7)	0.019 (6)	0.005 (6)	0.008 (5)	0.017 (5)
C17	0.041 (8)	0.031 (7)	0.030 (6)	−0.009 (6)	−0.010 (6)	0.013 (5)
C18	0.035 (8)	0.030 (6)	0.031 (6)	0.003 (5)	0.005 (5)	0.016 (5)
C19	0.031 (8)	0.040 (7)	0.035 (7)	0.004 (6)	−0.001 (5)	0.019 (6)
C20	0.033 (8)	0.059 (9)	0.038 (7)	0.003 (6)	0.004 (6)	0.026 (7)

Geometric parameters (Å, º)

Bi1—I1	2.9657 (12)	C3—C4	1.390 (17)
Bi1—I3	3.0082 (12)	C4—C5	1.355 (17)
Bi1—I4	3.0502 (13)	C4—H4B	0.950
Bi1—I2	3.1056 (13)	C5—H5A	0.950
Bi1—I5	3.2099 (12)	C6—C7	1.355 (15)
Bi1—I5^i	3.2197 (12)	C6—H6A	0.950
I5—Bi1^i	3.2197 (12)	C7—C8	1.408 (16)
N1—C1	1.324 (15)	C7—H7A	0.950
N1—C5	1.329 (15)	C8—C9	1.416 (16)
N1—H1A	0.880	C9—C10	1.341 (16)
N2—C10	1.343 (14)	C9—H9A	0.950
N2—C6	1.374 (15)	C10—H10A	0.950
N2—H2A	0.880	C11—C12	1.356 (16)
N3—C11	1.335 (16)	C11—H11A	0.950
N3—C15	1.345 (15)	C12—C13	1.377 (16)
N3—H3A	0.880	C12—H12A	0.950
N4—C20	1.340 (14)	C13—C14	1.427 (16)
N4—C16	1.341 (15)	C14—C15	1.355 (16)
N4—H4A	0.880	C14—H14A	0.950
O1—C3	1.329 (14)	C15—H15A	0.950
O1—H1	0.840	C16—C17	1.357 (16)
O2—C8	1.311 (13)	C16—H16A	0.950
O3—C13	1.317 (13)	C17—C18	1.439 (15)
O3—H3	0.840	C17—H17A	0.950
O4—C18	1.279 (13)	C18—C19	1.424 (16)
C1—C2	1.379 (17)	C19—C20	1.359 (16)
C1—H1B	0.950	C19—H19A	0.950
C2—C3	1.391 (16)	C20—H20A	0.950
C2—H2B	0.950
I1—Bi1—I3	95.43 (4)	C7—C6—N2	119.5 (12)
I1—Bi1—I4	91.10 (3)	C7—C6—H6A	120.2
I3—Bi1—I4	88.77 (4)	N2—C6—H6A	120.2
I1—Bi1—I2	85.81 (3)	C6—C7—C8	121.3 (12)
I3—Bi1—I2	93.51 (4)	C6—C7—H7A	119.3
I4—Bi1—I2	176.31 (3)	C8—C7—H7A	119.3
I1—Bi1—I5	174.51 (3)	O2—C8—C7	121.5 (11)
I3—Bi1—I5	88.65 (4)	O2—C8—C9	121.1 (11)
I4—Bi1—I5	92.67 (3)	C7—C8—C9	117.3 (11)
I2—Bi1—I5	90.28 (3)	C10—C9—C8	118.6 (12)
I1—Bi1—I5^i	86.95 (4)	C10—C9—H9A	120.7
I3—Bi1—I5^i	177.04 (3)	C8—C9—H9A	120.7
I4—Bi1—I5^i	89.43 (4)	C9—C10—N2	123.5 (12)
I2—Bi1—I5^i	88.40 (4)	C9—C10—H10A	118.2
I5—Bi1—I5^i	89.09 (4)	N2—C10—H10A	118.2
Bi1—I5—Bi1^i	90.91 (4)	N3—C11—C12	119.6 (12)
C1—N1—C5	119.8 (12)	N3—C11—H11A	120.2
C1—N1—H1A	120.1	C12—C11—H11A	120.2
C5—N1—H1A	120.1	C11—C12—C13	120.5 (12)
C10—N2—C6	119.6 (10)	C11—C12—H12A	119.8
C10—N2—H2A	120.2	C13—C12—H12A	119.8
C6—N2—H2A	120.2	O3—C13—C12	119.0 (12)
C11—N3—C15	122.6 (10)	O3—C13—C14	122.5 (11)
C11—N3—H3A	118.7	C12—C13—C14	118.6 (10)
C15—N3—H3A	118.7	C15—C14—C13	118.4 (12)
C20—N4—C16	122.9 (11)	C15—C14—H14A	120.8
C20—N4—H4A	118.6	C13—C14—H14A	120.8
C16—N4—H4A	118.6	N3—C15—C14	120.4 (12)
C3—O1—H1	109.5	N3—C15—H15A	119.8
C13—O3—H3	109.5	C14—C15—H15A	119.8
N1—C1—C2	120.4 (13)	N4—C16—C17	120.7 (11)
N1—C1—H1B	119.8	N4—C16—H16A	119.6
C2—C1—H1B	119.8	C17—C16—H16A	119.6
C1—C2—C3	119.4 (12)	C16—C17—C18	120.5 (12)
C1—C2—H2B	120.3	C16—C17—H17A	119.8
C3—C2—H2B	120.3	C18—C17—H17A	119.8
O1—C3—C4	118.2 (12)	O4—C18—C19	124.0 (11)
O1—C3—C2	122.5 (12)	O4—C18—C17	121.6 (11)
C4—C3—C2	119.2 (12)	C19—C18—C17	114.4 (11)
C5—C4—C3	116.9 (13)	C20—C19—C18	122.9 (11)
C5—C4—H4B	121.5	C20—C19—H19A	118.6
C3—C4—H4B	121.5	C18—C19—H19A	118.6
N1—C5—C4	124.1 (13)	N4—C20—C19	118.6 (12)
N1—C5—H5A	117.9	N4—C20—H20A	120.7
C4—C5—H5A	117.9	C19—C20—H20A	120.7
I3—Bi1—I5—Bi1^i	178.09 (3)	C8—C9—C10—N2	−1.8 (19)
I4—Bi1—I5—Bi1^i	89.39 (3)	C6—N2—C10—C9	1.0 (18)
I2—Bi1—I5—Bi1^i	−88.40 (3)	C15—N3—C11—C12	1.3 (19)
I5^i—Bi1—I5—Bi1^i	0.000 (2)	N3—C11—C12—C13	−1.1 (19)
C5—N1—C1—C2	1.6 (18)	C11—C12—C13—O3	178.1 (11)
N1—C1—C2—C3	−3.2 (18)	C11—C12—C13—C14	0.0 (18)
C1—C2—C3—O1	−177.9 (11)	O3—C13—C14—C15	−177.2 (11)
C1—C2—C3—C4	2.9 (18)	C12—C13—C14—C15	0.9 (17)
O1—C3—C4—C5	179.6 (12)	C11—N3—C15—C14	−0.4 (18)
C2—C3—C4—C5	−1.0 (19)	C13—C14—C15—N3	−0.7 (17)
C1—N1—C5—C4	0 (2)	C20—N4—C16—C17	2.4 (17)
C3—C4—C5—N1	−1 (2)	N4—C16—C17—C18	−1.5 (17)
C10—N2—C6—C7	−0.7 (17)	C16—C17—C18—O4	178.7 (11)
N2—C6—C7—C8	1.4 (18)	C16—C17—C18—C19	0.3 (16)
C6—C7—C8—O2	179.9 (11)	O4—C18—C19—C20	−178.1 (11)
C6—C7—C8—C9	−2.2 (17)	C17—C18—C19—C20	0.2 (17)
O2—C8—C9—C10	−179.8 (11)	C16—N4—C20—C19	−1.8 (18)
C7—C8—C9—C10	2.3 (17)	C18—C19—C20—N4	0.5 (18)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4	0.88	1.78	2.646 (14)	168
N2—H2A···O4^ii	0.88	1.87	2.715 (12)	160
N3—H3A···I2^iii	0.88	3.29	3.870 (11)	126
N3—H3A···I4^iv	0.88	2.87	3.633 (10)	147
N4—H4A···I1^v	0.88	3.25	3.898 (11)	133
N4—H4A···I2^v	0.88	2.89	3.627 (9)	144
O1—H1···O2	0.84	1.75	2.567 (12)	164
O3—H3···O2	0.84	1.70	2.518 (11)	163

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