catena-Poly[[ethyl­diphenyl­tin(IV)]-μ-isonicotinato-κ²O:N′]

In the title compound, [Sn(C₂H₅)(C₆H₅)₂(C₆H₄NO₂)]_n, the isonicotinate group functions in an N,O-bridging mode to link adjacent triorganotin groups into an infinite chain. The metal centre shows SnC₃NO trigonal–bipyramidal coordination, with the N and O atoms in axial positions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.028
• wR factor = 0.089
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.15
PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) .....         10 Ang.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.20 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.26 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.04
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C15    -   C16    ...       1.53 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

catena-Poly[[ethyldiphenyltin(IV)]-µ-isonicotinato-κ²O:N']

Crystal data

[Sn(C2H5)(C6H5)2(C6H4NO2)]	Z = 2
Mr = 424.05	F(000) = 424
Triclinic, P1	Dx = 1.543 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7562 (1) Å	Cell parameters from 6986 reflections
b = 9.9711 (1) Å	θ = 2.6–33.3°
c = 10.2908 (1) Å	µ = 1.41 mm^−1
α = 78.990 (1)°	T = 173 K
β = 77.066 (1)°	Plate, colourless
γ = 70.622 (1)°	0.38 × 0.20 × 0.10 mm
V = 912.97 (2) Å^3

Data collection

Bruker APEXII CCD area-detector diffractometer	4146 independent reflections
Radiation source: fine-focus sealed tube	3983 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.616, Tmax = 0.872	k = −12→12
13345 measured reflections	l = −13→13

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.061P)^2 + 0.7851P] where P = (Fo^2 + 2Fc^2)/3
4146 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 2.36 e Å^−3
1 restraint	Δρmin = −1.10 e Å^−3

Special details

Experimental. ¹H NMR (CDCl₃, δ, p.p.m.): –CH₃ (1.48–1.51, triplet), –CH₂ (1.80–1.88, quartet), –C₆H₅ (7.46–7.77, multiplet) and –C₅H₄N (7.90–8.75, multiplet); ¹⁹Sn NMR (CDCl₃): -12.8 p.p.m.

The crystal was measured to a 2θ_max of 66° but only the reflections below 55° were used in the refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Sn1	0.237601 (16)	0.752294 (16)	0.808295 (15)	0.01265 (8)
O1	0.4750 (2)	0.7242 (2)	0.7935 (2)	0.0160 (4)
O2	0.4087 (2)	0.9411 (2)	0.8670 (2)	0.0201 (4)
N1	0.9689 (2)	0.7820 (3)	0.8049 (2)	0.0159 (4)
C1	0.2946 (3)	0.5438 (3)	0.7448 (3)	0.0145 (5)
C2	0.3259 (3)	0.5202 (3)	0.6081 (3)	0.0171 (5)
C3	0.3673 (3)	0.3814 (3)	0.5710 (3)	0.0213 (5)
C4	0.3770 (3)	0.2627 (3)	0.6717 (3)	0.0213 (5)
C5	0.3454 (3)	0.2832 (3)	0.8084 (3)	0.0199 (5)
C6	0.3037 (3)	0.4222 (3)	0.8443 (3)	0.0167 (5)
C7	0.1881 (3)	0.7271 (3)	1.0279 (3)	0.0156 (5)
C8	0.3059 (3)	0.6940 (3)	1.1003 (3)	0.0183 (5)
C9	0.2823 (3)	0.6684 (3)	1.2419 (3)	0.0217 (5)
C10	0.1398 (3)	0.6743 (3)	1.3147 (3)	0.0204 (5)
C11	0.0230 (3)	0.7040 (3)	1.2454 (3)	0.0206 (5)
C12	0.0463 (3)	0.7307 (3)	1.1035 (3)	0.0192 (5)
C13	0.2042 (4)	0.9442 (3)	0.6636 (3)	0.0255 (6)
C14	0.1409 (9)	0.9505 (8)	0.5389 (6)	0.041 (2)	0.54 (1)
C14'	0.3152 (7)	0.9458 (7)	0.5414 (6)	0.022 (2)	0.46 (1)
C15	0.5034 (3)	0.8322 (3)	0.8259 (3)	0.0140 (5)
C16	0.6680 (3)	0.8152 (3)	0.8127 (3)	0.0132 (5)
C17	0.7114 (3)	0.9273 (3)	0.8393 (3)	0.0156 (5)
C18	0.8621 (3)	0.9067 (3)	0.8330 (3)	0.0175 (5)
C19	0.9263 (3)	0.6752 (3)	0.7780 (3)	0.0178 (5)
C20	0.7778 (3)	0.6872 (3)	0.7806 (3)	0.0159 (5)
H2	0.3187	0.5999	0.5398	0.021*
H3	0.3884	0.3680	0.4789	0.026*
H4	0.4049	0.1688	0.6475	0.026*
H5	0.3522	0.2031	0.8762	0.024*
H6	0.2812	0.4350	0.9366	0.020*
H8	0.4023	0.6892	1.0523	0.022*
H9	0.3624	0.6471	1.2883	0.026*
H10	0.1235	0.6581	1.4101	0.024*
H11	−0.0727	0.7064	1.2940	0.025*
H12	−0.0343	0.7513	1.0579	0.023*
H13a	0.1385	1.0250	0.7123	0.031*	0.54 (1)
H13b	0.3008	0.9625	0.6323	0.031*	0.54 (1)
H13c	0.1080	0.9633	0.6358	0.031*	0.46 (1)
H13d	0.1961	1.0252	0.7104	0.031*	0.46 (1)
H14a	0.1323	1.0442	0.4847	0.062*	0.54 (1)
H14b	0.0431	0.9366	0.5664	0.062*	0.54 (1)
H14c	0.2065	0.8749	0.4856	0.062*	0.54 (1)
H14d	0.2861	1.0384	0.4854	0.034*	0.46 (1)
H14e	0.3227	0.8688	0.4911	0.034*	0.46 (1)
H14f	0.4110	0.9314	0.5659	0.034*	0.46 (1)
H17	0.6400	1.0152	0.8610	0.019*
H18	0.8911	0.9832	0.8492	0.021*
H19	0.9999	0.5885	0.7565	0.021*
H20	0.7522	0.6102	0.7610	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0069 (1)	0.0133 (1)	0.0187 (1)	−0.0031 (1)	−0.0044 (1)	−0.0015 (1)
O1	0.008 (1)	0.018 (1)	0.025 (1)	−0.005 (1)	−0.004 (1)	−0.004 (1)
O2	0.011 (1)	0.018 (1)	0.031 (1)	−0.003 (1)	−0.004 (1)	−0.006 (1)
N1	0.010 (1)	0.017 (1)	0.023 (1)	−0.005 (1)	−0.005 (1)	−0.003 (1)
C1	0.007 (1)	0.018 (1)	0.020 (1)	−0.004 (1)	−0.004 (1)	−0.001 (1)
C2	0.013 (1)	0.018 (1)	0.021 (1)	−0.005 (1)	−0.006 (1)	0.000 (1)
C3	0.015 (1)	0.027 (2)	0.024 (1)	−0.008 (1)	−0.003 (1)	−0.008 (1)
C4	0.014 (1)	0.017 (1)	0.035 (2)	−0.004 (1)	−0.005 (1)	−0.008 (1)
C5	0.013 (1)	0.017 (1)	0.030 (1)	−0.005 (1)	−0.005 (1)	0.001 (1)
C6	0.010 (1)	0.020 (1)	0.020 (1)	−0.004 (1)	−0.004 (1)	−0.001 (1)
C7	0.010 (1)	0.015 (1)	0.022 (1)	−0.003 (1)	−0.004 (1)	−0.003 (1)
C8	0.011 (1)	0.022 (1)	0.023 (1)	−0.006 (1)	−0.005 (1)	−0.002 (1)
C9	0.017 (1)	0.027 (2)	0.025 (1)	−0.008 (1)	−0.008 (1)	−0.002 (1)
C10	0.020 (1)	0.023 (1)	0.018 (1)	−0.006 (1)	−0.004 (1)	−0.002 (1)
C11	0.011 (1)	0.023 (1)	0.025 (1)	−0.003 (1)	−0.001 (1)	−0.003 (1)
C12	0.010 (1)	0.023 (1)	0.025 (1)	−0.003 (1)	−0.006 (1)	−0.003 (1)
C13	0.026 (2)	0.023 (2)	0.032 (2)	−0.011 (1)	−0.016 (1)	0.004 (1)
C14	0.052 (4)	0.048 (4)	0.033 (3)	−0.027 (3)	−0.021 (3)	0.010 (3)
C14'	0.020 (3)	0.024 (3)	0.020 (3)	−0.007 (2)	0.000 (2)	0.001 (2)
C15	0.009 (1)	0.015 (1)	0.019 (1)	−0.004 (1)	−0.005 (1)	0.000 (1)
C16	0.008 (1)	0.015 (1)	0.016 (1)	−0.004 (1)	−0.004 (1)	0.000 (1)
C17	0.010 (1)	0.016 (1)	0.022 (1)	−0.003 (1)	−0.005 (1)	−0.004 (1)
C18	0.012 (1)	0.018 (1)	0.026 (1)	−0.006 (1)	−0.006 (1)	−0.005 (1)
C19	0.008 (1)	0.017 (1)	0.029 (1)	−0.003 (1)	−0.004 (1)	−0.005 (1)
C20	0.0105 (1)	0.015 (1)	0.025 (1)	−0.005 (1)	−0.004 (1)	−0.005 (1)

Geometric parameters (Å, º)

Sn1—C1	2.155 (3)	C17—C18	1.404 (3)
Sn1—C7	2.186 (3)	C19—C20	1.408 (4)
Sn1—C13	2.168 (3)	C2—H2	0.95
Sn1—N1^i	2.546 (2)	C3—H3	0.95
Sn1—O1	2.212 (2)	C4—H4	0.95
C15—O1	1.313 (3)	C5—H5	0.95
C15—O2	1.243 (3)	C6—H6	0.95
N1—C19	1.357 (4)	C8—H8	0.95
N1—C18	1.363 (4)	C9—H9	0.95
C1—C2	1.420 (4)	C10—H10	0.95
C1—C6	1.422 (4)	C11—H11	0.95
C2—C3	1.409 (4)	C12—H12	0.95
C3—C4	1.408 (4)	C13—H13a	0.99
C4—C5	1.410 (4)	C13—H13b	0.99
C5—C6	1.406 (4)	C13—H13c	0.99
C7—C12	1.420 (4)	C13—H13d	0.99
C7—C8	1.422 (4)	C14—H14a	0.98
C8—C9	1.410 (4)	C14—H14b	0.98
C9—C10	1.412 (4)	C14—H14c	0.98
C10—C11	1.398 (4)	C14'—H14d	0.98
C11—C12	1.414 (4)	C14'—H14e	0.98
C13—C14'	1.465 (6)	C14'—H14f	0.98
C13—C14	1.527 (6)	C17—H17	0.95
C15—C16	1.535 (3)	C18—H18	0.95
C16—C20	1.407 (4)	C19—H19	0.95
C16—C17	1.410 (4)	C20—H20	0.95
C1—Sn1—C7	107.9 (1)	C5—C4—H4	120.0
C1—Sn1—C13	120.8 (1)	C6—C5—H5	120.0
C1—Sn1—O1	89.3 (1)	C4—C5—H5	120.0
C1—Sn1—N1^i	88.2 (1)	C5—C6—H6	119.4
C7—Sn1—C13	130.5 (1)	C1—C6—H6	119.4
C7—Sn1—O1	95.5 (1)	C9—C8—H8	119.4
C7—Sn1—N1^i	89.1 (1)	C7—C8—H8	119.4
C13—Sn1—O1	93.6 (1)	C8—C9—H9	120.0
C13—Sn1—N1^i	84.2 (1)	C10—C9—H9	120.0
N1^i—Sn1—O1	175.3 (1)	C11—C10—H10	120.2
C15—O1—Sn1	114.5 (2)	C9—C10—H10	120.2
C19—N1—C18	117.8 (2)	C10—C11—H11	119.8
C19—N1—Sn1^ii	121.9 (2)	C12—C11—H11	119.8
C18—N1—Sn1^ii	120.3 (2)	C11—C12—H12	119.4
C2—C1—C6	117.6 (2)	C7—C12—H12	119.4
C2—C1—Sn1	123.6 (2)	C14—C13—H13a	107.4
C6—C1—Sn1	118.8 (2)	Sn1—C13—H13a	107.4
C3—C2—C1	121.7 (2)	C14—C13—H13b	107.4
C4—C3—C2	119.5 (3)	Sn1—C13—H13b	107.4
C3—C4—C5	120.1 (3)	H13a—C13—H13b	106.9
C6—C5—C4	120.0 (3)	C14'—C13—H13c	107.7
C5—C6—C1	121.2 (3)	Sn1—C13—H13c	107.7
C12—C7—C8	117.5 (2)	C14'—C13—H13d	107.7
C12—C7—Sn1	123.7 (2)	C14—C13—H13d	127.5
C8—C7—Sn1	118.6 (2)	Sn1—C13—H13d	107.7
C9—C8—C7	121.3 (2)	H13c—C13—H13d	107.1
C8—C9—C10	120.1 (3)	C13—C14—H14a	109.5
C11—C10—C9	119.6 (3)	C13—C14—H14b	109.5
C10—C11—C12	120.4 (2)	H14a—C14—H14b	109.5
C11—C12—C7	121.2 (2)	C13—C14—H14c	109.5
C14'—C13—Sn1	118.3 (3)	H14a—C14—H14c	109.5
C14—C13—Sn1	119.8 (3)	H14b—C14—H14c	109.5
O2—C15—O1	125.0 (2)	C13—C14'—H14d	109.5
O2—C15—C16	120.1 (2)	C13—C14'—H14e	109.5
O1—C15—C16	114.9 (2)	H14d—C14'—H14e	109.5
C20—C16—C17	118.6 (2)	C13—C14'—H14f	109.5
C20—C16—C15	121.7 (2)	H14d—C14'—H14f	109.5
C17—C16—C15	119.7 (2)	H14e—C14'—H14f	109.5
C18—C17—C16	118.7 (2)	C18—C17—H17	120.6
N1—C18—C17	123.1 (2)	C16—C17—H17	120.6
N1—C19—C20	122.9 (2)	N1—C18—H18	118.5
C16—C20—C19	118.9 (2)	C17—C18—H18	118.5
C3—C2—H2	119.2	N1—C19—H19	118.6
C1—C2—H2	119.2	C20—C19—H19	118.6
C4—C3—H3	120.3	C16—C20—H20	120.5
C2—C3—H3	120.3	C19—C20—H20	120.5
C3—C4—H4	120.0
C1—Sn1—O1—C15	−179.6 (2)	C8—C9—C10—C11	0.7 (4)
C13—Sn1—O1—C15	59.6 (2)	C9—C10—C11—C12	−1.1 (4)
C7—Sn1—O1—C15	−71.6 (2)	C10—C11—C12—C7	0.4 (4)
C13—Sn1—C1—C2	5.9 (2)	C8—C7—C12—C11	0.7 (4)
C7—Sn1—C1—C2	176.6 (2)	Sn1—C7—C12—C11	175.7 (2)
O1—Sn1—C1—C2	−87.8 (2)	C1—Sn1—C13—C14'	−48.2 (4)
N1^i—Sn1—C1—C2	88.1 (2)	C7—Sn1—C13—C14'	143.5 (3)
C13—Sn1—C1—C6	−175.0 (2)	O1—Sn1—C13—C14'	43.2 (4)
C7—Sn1—C1—C6	−4.3 (2)	N1^i—Sn1—C13—C14'	−132.7 (4)
O1—Sn1—C1—C6	91.3 (2)	C1—Sn1—C13—C14	32.3 (5)
N1^i—Sn1—C1—C6	−92.8 (2)	C7—Sn1—C13—C14	−135.9 (4)
C6—C1—C2—C3	−1.2 (4)	O1—Sn1—C13—C14	123.7 (4)
Sn1—C1—C2—C3	177.9 (2)	N1^i—Sn1—C13—C14	−52.1 (4)
C1—C2—C3—C4	0.5 (4)	Sn1—O1—C15—O2	2.7 (3)
C2—C3—C4—C5	0.0 (4)	Sn1—O1—C15—C16	−178.6 (2)
C3—C4—C5—C6	0.2 (4)	O2—C15—C16—C20	173.0 (3)
C4—C5—C6—C1	−0.9 (4)	O1—C15—C16—C20	−5.7 (4)
C2—C1—C6—C5	1.4 (4)	O2—C15—C16—C17	−3.9 (4)
Sn1—C1—C6—C5	−177.8 (2)	O1—C15—C16—C17	177.3 (2)
C1—Sn1—C7—C12	−87.2 (2)	C20—C16—C17—C18	−0.1 (4)
C13—Sn1—C7—C12	82.2 (3)	C15—C16—C17—C18	176.9 (2)
O1—Sn1—C7—C12	−178.3 (2)	C19—N1—C18—C17	2.0 (4)
N1^i—Sn1—C7—C12	0.6 (2)	Sn1^ii—N1—C18—C17	−176.8 (2)
C1—Sn1—C7—C8	87.6 (2)	C16—C17—C18—N1	−1.3 (4)
C13—Sn1—C7—C8	−102.9 (2)	C18—N1—C19—C20	−1.3 (4)
O1—Sn1—C7—C8	−3.4 (2)	Sn1^ii—N1—C19—C20	177.5 (2)
N1^i—Sn1—C7—C8	175.5 (2)	C17—C16—C20—C19	0.8 (4)
C12—C7—C8—C9	−1.1 (4)	C15—C16—C20—C19	−176.2 (2)
Sn1—C7—C8—C9	−176.3 (2)	N1—C19—C20—C16	−0.1 (4)
C7—C8—C9—C10	0.4 (4)

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