catena-Poly[[triphenyl­tin(IV)]-μ-6-oxo­1,6-dihydropyridine-3-carboxyl­ato]

The title compound, [Sn(C₆H₅)₃(C₆H₄NO₃)], possesses an infinite chain structure. The SnO₂C₃ centre has distorted trigonal–bipyramidal geometry with the O atoms in the apical positions. A strong inter­molecular N—H...O hydrogen bond results in the formation of double chains.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.027
• wR factor = 0.071
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.13 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C9

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

catena-Poly[[triphenyltin(IV)]-µ-6-hydroxypyridine-3-carboxylato]

Crystal data

[Sn(C6H5)3(C6H4NO3)]	F(000) = 976
Mr = 488.09	Dx = 1.518 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5143 reflections
a = 9.5629 (17) Å	θ = 2.2–27.8°
b = 10.6579 (19) Å	µ = 1.22 mm^−1
c = 21.353 (4) Å	T = 298 K
β = 101.155 (3)°	Block, colourless
V = 2135.2 (7) Å^3	0.49 × 0.46 × 0.41 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	3755 independent reflections
Radiation source: fine-focus sealed tube	3053 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→11
Tmin = 0.586, Tmax = 0.635	k = −12→12
10839 measured reflections	l = −24→25

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.071	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.034P)^2 + 0.6145P] where P = (Fo^2 + 2Fc^2)/3
3755 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −0.47 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
Sn1	0.38463 (2)	0.22844 (2)	0.371584 (10)	0.03163 (9)
N1	0.4684 (3)	0.8383 (2)	0.31816 (13)	0.0412 (7)
H1	0.5020	0.8854	0.2919	0.049*
O1	0.3573 (2)	0.4286 (2)	0.37293 (10)	0.0406 (6)
O2	0.4407 (3)	0.4558 (2)	0.28338 (11)	0.0516 (7)
O3	0.4339 (3)	1.0117 (2)	0.37454 (12)	0.0543 (6)
C1	0.4027 (3)	0.4975 (3)	0.33130 (15)	0.0370 (7)
C2	0.4619 (4)	0.7144 (3)	0.30654 (15)	0.0385 (8)
H2	0.4940	0.6832	0.2712	0.046*
C3	0.4092 (3)	0.6339 (3)	0.34543 (14)	0.0311 (7)
C4	0.3660 (3)	0.6863 (3)	0.39925 (15)	0.0379 (8)
H4	0.3307	0.6338	0.4273	0.045*
C5	0.3746 (4)	0.8110 (3)	0.41112 (16)	0.0425 (8)
H5	0.3467	0.8419	0.4475	0.051*
C6	0.4251 (4)	0.8959 (3)	0.36931 (15)	0.0395 (8)
C7	0.2975 (3)	0.2123 (3)	0.45612 (15)	0.0366 (8)
C8	0.2362 (4)	0.1009 (4)	0.4700 (2)	0.0675 (13)
H8	0.2306	0.0339	0.4418	0.081*
C9	0.1831 (6)	0.0879 (5)	0.5256 (3)	0.0968 (19)
H9	0.1435	0.0119	0.5348	0.116*
C10	0.1886 (6)	0.1860 (6)	0.5668 (2)	0.0900 (17)
H10	0.1539	0.1766	0.6043	0.108*
C11	0.2440 (5)	0.2965 (5)	0.5536 (2)	0.0733 (14)
H11	0.2454	0.3640	0.5813	0.088*
C12	0.2991 (4)	0.3099 (4)	0.49839 (17)	0.0536 (10)
H12	0.3379	0.3865	0.4898	0.064*
C13	0.2302 (3)	0.1953 (3)	0.28674 (15)	0.0376 (8)
C14	0.2259 (4)	0.0894 (3)	0.24924 (17)	0.0528 (9)
H14	0.2989	0.0307	0.2586	0.063*
C15	0.1152 (5)	0.0684 (4)	0.19798 (19)	0.0695 (12)
H15	0.1147	−0.0035	0.1733	0.083*
C16	0.0067 (5)	0.1534 (6)	0.1837 (2)	0.0863 (16)
H16	−0.0682	0.1391	0.1496	0.104*
C17	0.0087 (5)	0.2593 (5)	0.2196 (2)	0.0890 (17)
H17	−0.0647	0.3175	0.2098	0.107*
C18	0.1192 (4)	0.2807 (4)	0.27052 (19)	0.0612 (11)
H18	0.1194	0.3537	0.2944	0.073*
C19	0.6108 (3)	0.2454 (3)	0.38611 (15)	0.0382 (8)
C20	0.6747 (4)	0.3350 (4)	0.42928 (17)	0.0531 (9)
H20	0.6178	0.3872	0.4487	0.064*
C21	0.8207 (5)	0.3483 (5)	0.4441 (2)	0.0785 (14)
H21	0.8627	0.4062	0.4746	0.094*
C22	0.9026 (5)	0.2745 (5)	0.4130 (3)	0.0827 (16)
H22	1.0011	0.2848	0.4217	0.099*
C23	0.8441 (5)	0.1876 (5)	0.3704 (2)	0.0763 (14)
H23	0.9021	0.1392	0.3496	0.092*
C24	0.6973 (4)	0.1696 (4)	0.35701 (18)	0.0539 (10)
H24	0.6574	0.1071	0.3287	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.03997 (14)	0.02032 (14)	0.03523 (13)	−0.00202 (9)	0.00883 (10)	−0.00077 (9)
N1	0.0582 (18)	0.0239 (16)	0.0461 (17)	−0.0021 (13)	0.0214 (14)	0.0053 (13)
O1	0.0616 (15)	0.0190 (12)	0.0444 (13)	−0.0018 (10)	0.0183 (12)	0.0007 (10)
O2	0.0845 (18)	0.0317 (14)	0.0465 (14)	0.0005 (12)	0.0325 (13)	−0.0098 (11)
O3	0.0843 (18)	0.0149 (13)	0.0638 (16)	0.0025 (12)	0.0149 (13)	−0.0018 (11)
C1	0.0432 (19)	0.0241 (18)	0.044 (2)	−0.0001 (14)	0.0088 (15)	−0.0005 (15)
C2	0.055 (2)	0.026 (2)	0.0373 (18)	0.0025 (15)	0.0169 (16)	−0.0022 (14)
C3	0.0409 (17)	0.0211 (17)	0.0313 (16)	0.0016 (13)	0.0074 (14)	−0.0001 (13)
C4	0.053 (2)	0.0275 (18)	0.0359 (17)	−0.0011 (15)	0.0164 (15)	0.0021 (14)
C5	0.063 (2)	0.0272 (19)	0.0408 (19)	0.0038 (17)	0.0177 (17)	−0.0025 (15)
C6	0.051 (2)	0.025 (2)	0.0397 (19)	0.0037 (15)	0.0016 (16)	0.0001 (14)
C7	0.0373 (18)	0.036 (2)	0.0374 (17)	0.0049 (14)	0.0093 (14)	0.0082 (14)
C8	0.088 (3)	0.037 (2)	0.091 (3)	0.012 (2)	0.050 (3)	0.019 (2)
C9	0.126 (4)	0.064 (3)	0.123 (5)	0.024 (3)	0.081 (4)	0.050 (3)
C10	0.101 (4)	0.118 (5)	0.064 (3)	0.035 (4)	0.049 (3)	0.039 (3)
C11	0.069 (3)	0.109 (4)	0.046 (2)	0.004 (3)	0.019 (2)	−0.015 (3)
C12	0.055 (2)	0.061 (3)	0.046 (2)	−0.007 (2)	0.0134 (18)	−0.0083 (19)
C13	0.0410 (18)	0.036 (2)	0.0371 (18)	−0.0057 (15)	0.0094 (14)	−0.0007 (15)
C14	0.066 (2)	0.043 (2)	0.046 (2)	−0.0071 (19)	0.0045 (19)	−0.0033 (17)
C15	0.080 (3)	0.072 (3)	0.053 (3)	−0.025 (3)	0.004 (2)	−0.018 (2)
C16	0.059 (3)	0.138 (5)	0.056 (3)	−0.015 (3)	−0.005 (2)	−0.013 (3)
C17	0.057 (3)	0.127 (5)	0.075 (3)	0.028 (3)	−0.008 (2)	−0.007 (3)
C18	0.056 (2)	0.069 (3)	0.055 (2)	0.015 (2)	0.0026 (19)	−0.011 (2)
C19	0.0349 (18)	0.039 (2)	0.0415 (19)	−0.0014 (15)	0.0082 (15)	0.0077 (15)
C20	0.048 (2)	0.057 (3)	0.052 (2)	−0.0094 (19)	0.0042 (18)	−0.0028 (19)
C21	0.066 (3)	0.086 (4)	0.073 (3)	−0.021 (3)	−0.012 (2)	0.010 (3)
C22	0.048 (3)	0.087 (4)	0.113 (4)	−0.006 (3)	0.018 (3)	0.040 (3)
C23	0.057 (3)	0.082 (4)	0.096 (4)	0.019 (3)	0.029 (3)	0.032 (3)
C24	0.055 (2)	0.044 (2)	0.064 (2)	0.0082 (19)	0.0164 (19)	0.0053 (19)

Geometric parameters (Å, º)

Sn1—C19	2.133 (3)	C10—H10	0.9300
Sn1—C13	2.134 (3)	C11—C12	1.388 (5)
Sn1—C7	2.137 (3)	C11—H11	0.9300
Sn1—O1	2.150 (2)	C12—H12	0.9300
Sn1—O3^i	2.356 (2)	C13—C14	1.380 (5)
N1—C2	1.343 (4)	C13—C18	1.391 (5)
N1—C6	1.385 (4)	C14—C15	1.385 (5)
N1—H1	0.8600	C14—H14	0.9300
C1—O1	1.292 (4)	C15—C16	1.367 (6)
C1—O2	1.233 (4)	C15—H15	0.9300
O3—C6	1.240 (4)	C16—C17	1.363 (7)
O3—Sn1^ii	2.356 (2)	C16—H16	0.9300
C1—C3	1.483 (4)	C17—C18	1.380 (6)
C2—C3	1.357 (4)	C17—H17	0.9300
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.410 (4)	C19—C20	1.384 (5)
C4—C5	1.353 (5)	C19—C24	1.386 (4)
C4—H4	0.9300	C20—C21	1.378 (5)
C5—C6	1.420 (5)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.369 (7)
C7—C12	1.375 (5)	C21—H21	0.9300
C7—C8	1.382 (5)	C22—C23	1.343 (7)
C8—C9	1.385 (6)	C22—H22	0.9300
C8—H8	0.9300	C23—C24	1.391 (5)
C9—C10	1.361 (7)	C23—H23	0.9300
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.344 (7)
C19—Sn1—C13	130.80 (12)	C9—C10—H10	119.8
C19—Sn1—C7	115.76 (12)	C10—C11—C12	119.9 (5)
C13—Sn1—C7	112.63 (12)	C10—C11—H11	120.1
C19—Sn1—O1	92.09 (10)	C12—C11—H11	120.1
C13—Sn1—O1	96.30 (11)	C7—C12—C11	121.5 (4)
C7—Sn1—O1	90.01 (10)	C7—C12—H12	119.3
C19—Sn1—O3^i	83.52 (11)	C11—C12—H12	119.3
C13—Sn1—O3^i	87.84 (11)	C14—C13—C18	117.1 (3)
C7—Sn1—O3^i	90.42 (10)	C14—C13—Sn1	124.5 (3)
O1—Sn1—O3^i	175.31 (9)	C18—C13—Sn1	118.2 (3)
C2—N1—C6	124.9 (3)	C13—C14—C15	121.5 (4)
C2—N1—H1	117.6	C13—C14—H14	119.2
C6—N1—H1	117.6	C15—C14—H14	119.2
C1—O1—Sn1	119.82 (19)	C16—C15—C14	120.0 (4)
C6—O3—Sn1^ii	164.4 (3)	C16—C15—H15	120.0
O2—C1—O1	123.9 (3)	C14—C15—H15	120.0
O2—C1—C3	121.0 (3)	C17—C16—C15	119.7 (4)
O1—C1—C3	115.1 (3)	C17—C16—H16	120.1
N1—C2—C3	121.2 (3)	C15—C16—H16	120.1
N1—C2—H2	119.4	C16—C17—C18	120.4 (5)
C3—C2—H2	119.4	C16—C17—H17	119.8
C2—C3—C4	116.7 (3)	C18—C17—H17	119.8
C2—C3—C1	120.1 (3)	C17—C18—C13	121.3 (4)
C4—C3—C1	123.2 (3)	C17—C18—H18	119.4
C5—C4—C3	121.7 (3)	C13—C18—H18	119.4
C5—C4—H4	119.1	C20—C19—C24	118.4 (3)
C3—C4—H4	119.1	C20—C19—Sn1	117.4 (2)
C4—C5—C6	121.6 (3)	C24—C19—Sn1	124.2 (3)
C4—C5—H5	119.2	C21—C20—C19	121.4 (4)
C6—C5—H5	119.2	C21—C20—H20	119.3
O3—C6—N1	119.1 (3)	C19—C20—H20	119.3
O3—C6—C5	127.1 (3)	C22—C21—C20	118.6 (5)
N1—C6—C5	113.8 (3)	C22—C21—H21	120.7
C12—C7—C8	117.4 (3)	C20—C21—H21	120.7
C12—C7—Sn1	122.5 (3)	C23—C22—C21	121.5 (5)
C8—C7—Sn1	120.1 (3)	C23—C22—H22	119.2
C7—C8—C9	120.8 (4)	C21—C22—H22	119.2
C7—C8—H8	119.6	C22—C23—C24	120.4 (5)
C9—C8—H8	119.6	C22—C23—H23	119.8
C10—C9—C8	120.1 (5)	C24—C23—H23	119.8
C10—C9—H9	119.9	C19—C24—C23	119.6 (4)
C8—C9—H9	119.9	C19—C24—H24	120.2
C11—C10—C9	120.3 (4)	C23—C24—H24	120.2
C11—C10—H10	119.8

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^iii	0.86	1.95	2.785 (4)	165

Symmetry code: (iii) −x+1, y+1/2, −z+1/2.