Tetra­kis(μ₂-3-hydroxy­pyridine-2-carboxyl­ato-κ²O,N)di-μ₃oxo-tetra­kis[dimethyl­tin(IV)]

In the crystal structure of the title centrosymmetric distannox­ane, [Sn₄(CH₃)₈(C₆H₄NO₃)O₂], one 3-hydroxy­pyridine-2-carboxyl­ate ligand chelates through N and O atoms to an Sn atom. A singly bonded carboxyl­ate O atom coordinates weakly to another independent Sn atom [at a distance of 2.983 (4) Å], which is pseudo-chelated by the other 3-hydroxy­pyridine-2-carboxyl­ate ligand [Sn...N 2.846 (4) Å]. The μ₃-binding mode of both ligands leads to a skew-trapezoidal bipyramidal geometry [C—Sn—C 136.0 (3)°] for the six-coordinate Sn atom and a trans-penta­gonal bipyramidal geometry [C—Sn—C 148.9 (3)°] for the seven-coordinate Sn atom.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.037
• wR factor = 0.114
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C9     -   C10     ..       6.12 su
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.17 Ratio

   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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Tetrakis(µ₂-3-hydroxypyridine-2-carboxylato-κ²O,N)di-µ₃oxo- tetrakis[dimethyltin(IV)]

Crystal data

[Sn4(CH3)8(C6H4NO3)O2]	Z = 1
Mr = 1179.44	F(000) = 572
Triclinic, P1	Dx = 1.867 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.395 (1) Å	Cell parameters from 3297 reflections
b = 10.055 (1) Å	θ = 2.5–28.0°
c = 13.157 (2) Å	µ = 2.42 mm^−1
α = 89.336 (2)°	T = 295 K
β = 82.842 (2)°	Block, colourless
γ = 72.231 (1)°	0.45 × 0.37 × 0.23 mm
V = 1049.0 (2) Å^3

Data collection

Siemens SMART CCD area-detector diffractometer	4646 independent reflections
Radiation source: fine-focus sealed tube	3460 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.337, Tmax = 0.576	k = −13→12
6588 measured reflections	l = −17→11

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0585P)^2 + 0.3682P] where P = (Fo^2 + 2Fc^2)/3
4646 reflections	(Δ/σ)max = 0.001
248 parameters	Δρmax = 1.39 e Å^−3
0 restraints	Δρmin = −0.89 e Å^−3

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

	x	y	z	Uiso*/Ueq
Sn1	0.35824 (4)	0.61937 (3)	0.44093 (3)	0.0380 (1)
Sn2	0.73872 (5)	0.43905 (4)	0.27757 (3)	0.0422 (1)
O1	0.4602 (4)	0.6327 (4)	0.2707 (3)	0.048 (1)
O2	0.4658 (5)	0.6930 (5)	0.1076 (3)	0.070 (1)
O3	0.2016 (6)	0.8547 (5)	0.0419 (3)	0.074 (1)
O4	0.8998 (5)	0.3010 (4)	0.3746 (3)	0.049 (1)
O5	1.1412 (5)	0.1595 (5)	0.4145 (3)	0.062 (1)
O6	1.3957 (5)	0.0687 (5)	0.2746 (4)	0.072 (1)
O7	0.5959 (4)	0.4795 (4)	0.4149 (3)	0.043 (1)
N1	0.1405 (6)	0.8044 (5)	0.3162 (3)	0.044 (1)
N2	1.0199 (6)	0.2918 (6)	0.1776 (3)	0.057 (1)
C1	0.1978 (8)	0.5060 (6)	0.4062 (5)	0.054 (1)
C2	0.3886 (9)	0.8103 (6)	0.4823 (5)	0.059 (2)
C3	0.6259 (8)	0.3215 (7)	0.1951 (5)	0.060 (2)
C4	0.8352 (9)	0.6078 (7)	0.2467 (6)	0.074 (2)
C5	−0.0171 (7)	0.8831 (6)	0.3371 (4)	0.051 (1)
C6	−0.1121 (8)	0.9559 (6)	0.2629 (5)	0.058 (2)
C7	−0.0375 (7)	0.9458 (6)	0.1636 (5)	0.057 (2)
C8	0.1272 (7)	0.8640 (6)	0.1392 (4)	0.047 (1)
C9	0.2133 (6)	0.7946 (5)	0.2183 (4)	0.040 (1)
C10	0.3933 (8)	0.7015 (6)	0.1974 (4)	0.049 (1)
C11	1.0800 (9)	0.2842 (9)	0.0791 (6)	0.076 (2)
C12	1.244 (1)	0.210 (1)	0.0390 (6)	0.092 (3)
C13	1.3519 (9)	0.1402 (9)	0.1060 (6)	0.080 (2)
C14	1.2905 (8)	0.1408 (7)	0.2097 (5)	0.058 (2)
C15	1.1245 (7)	0.2204 (6)	0.2419 (4)	0.047 (1)
C16	1.0511 (6)	0.2256 (5)	0.3529 (5)	0.044 (1)
H3o	0.3023	0.8121	0.0397	0.088*
H6o	1.3626	0.1021	0.3328	0.087*
H1a	0.2147	0.4859	0.3338	0.081*
H1b	0.0826	0.5602	0.4266	0.081*
H1c	0.2229	0.4200	0.4423	0.081*
H2a	0.4356	0.8010	0.5459	0.089*
H2b	0.2810	0.8813	0.4902	0.089*
H2c	0.4631	0.8360	0.4299	0.089*
H3a	0.5289	0.3102	0.2369	0.091*
H3b	0.7055	0.2313	0.1768	0.091*
H3c	0.5920	0.3693	0.1341	0.091*
H4a	0.8270	0.6590	0.3093	0.112*
H4b	0.7712	0.6685	0.1994	0.112*
H4c	0.9512	0.5730	0.2174	0.112*
H5	−0.0677	0.8906	0.4047	0.061*
H6	−0.2236	1.0101	0.2806	0.069*
H7	−0.0979	0.9938	0.1128	0.068*
H11	1.0076	0.3323	0.0337	0.091*
H12	1.2787	0.2066	−0.0310	0.110*
H13	1.4643	0.0935	0.0826	0.096*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0408 (2)	0.0362 (2)	0.0333 (2)	−0.0037 (2)	−0.0118 (1)	0.0059 (1)
Sn2	0.0489 (2)	0.0507 (2)	0.0286 (2)	−0.0168 (2)	−0.0069 (2)	0.0084 (2)
O1	0.045 (2)	0.056 (2)	0.036 (2)	−0.004 (2)	−0.008 (2)	0.015 (2)
O2	0.058 (3)	0.097 (4)	0.042 (2)	−0.005 (2)	0.001 (2)	0.017 (2)
O3	0.080 (3)	0.090 (3)	0.029 (2)	0.007 (3)	−0.012 (2)	0.018 (2)
O4	0.048 (2)	0.057 (2)	0.031 (2)	−0.003 (2)	0.002 (2)	0.009 (2)
O5	0.054 (2)	0.071 (3)	0.047 (2)	0.001 (2)	−0.007 (2)	0.021 (2)
O6	0.054 (3)	0.085 (3)	0.063 (3)	−0.004 (2)	0.000 (2)	0.003 (3)
O7	0.046 (2)	0.042 (2)	0.029 (2)	0.002 (2)	−0.006 (2)	0.007 (2)
N1	0.050 (3)	0.047 (3)	0.030 (2)	−0.005 (2)	−0.007 (2)	0.011 (2)
N2	0.054 (3)	0.083 (4)	0.030 (2)	−0.019 (3)	0.001 (2)	0.006 (2)
C1	0.059 (3)	0.057 (4)	0.052 (4)	−0.021 (3)	−0.019 (3)	0.013 (3)
C2	0.081 (4)	0.040 (3)	0.056 (4)	−0.014 (3)	−0.021 (3)	0.003 (3)
C3	0.064 (4)	0.068 (4)	0.051 (4)	−0.017 (3)	−0.018 (3)	−0.013 (3)
C4	0.072 (4)	0.077 (5)	0.090 (5)	−0.039 (4)	−0.030 (4)	0.038 (4)
C5	0.053 (3)	0.051 (3)	0.038 (3)	−0.003 (3)	0.003 (2)	−0.001 (3)
C6	0.057 (3)	0.051 (3)	0.055 (4)	0.000 (3)	−0.010 (3)	0.008 (3)
C7	0.064 (4)	0.053 (4)	0.045 (3)	−0.001 (3)	−0.019 (3)	0.008 (3)
C8	0.057 (3)	0.051 (3)	0.029 (3)	−0.009 (3)	−0.011 (2)	0.009 (2)
C9	0.045 (3)	0.039 (3)	0.030 (3)	−0.005 (2)	−0.010 (2)	0.008 (2)
C10	0.063 (3)	0.056 (3)	0.034 (3)	−0.022 (3)	−0.023 (3)	0.016 (2)
C11	0.061 (4)	0.112 (6)	0.058 (4)	−0.032 (4)	−0.004 (3)	0.007 (4)
C12	0.082 (5)	0.155 (9)	0.040 (4)	−0.047 (6)	0.012 (4)	0.004 (5)
C13	0.059 (4)	0.116 (7)	0.060 (5)	−0.024 (4)	0.011 (3)	−0.014 (4)
C14	0.053 (3)	0.065 (4)	0.057 (4)	−0.021 (3)	−0.002 (3)	0.003 (3)
C15	0.044 (3)	0.054 (3)	0.041 (3)	−0.013 (3)	−0.004 (2)	0.005 (3)
C16	0.037 (3)	0.037 (3)	0.055 (3)	−0.005 (2)	−0.007 (2)	−0.005 (2)

Geometric parameters (Å, º)

Sn1—C1	2.104 (6)	C8—C9	1.398 (7)
Sn1—C2	2.099 (6)	C9—C10	1.508 (8)
Sn1—N1	2.846 (4)	C11—C12	1.39 (1)
Sn1—O1	2.314 (4)	C12—C13	1.38 (1)
Sn1—O4^i	2.983 (4)	C13—C14	1.397 (9)
Sn1—O7	2.050 (3)	C14—C15	1.394 (8)
Sn1—O7^i	2.154 (3)	C15—C16	1.508 (8)
Sn2—C3	2.107 (5)	O3—H3o	0.82
Sn2—C4	2.108 (6)	O6—H6o	0.82
Sn2—N2	2.576 (5)	C1—H1a	0.96
Sn2—O1	2.557 (3)	C1—H1b	0.96
Sn2—O4	2.152 (4)	C1—H1c	0.96
Sn2—O7	2.012 (3)	C2—H2a	0.96
O1—C10	1.267 (6)	C2—H2b	0.96
O2—C10	1.251 (7)	C2—H2c	0.96
O3—C8	1.344 (7)	C3—H3a	0.96
O4—C16	1.264 (6)	C3—H3b	0.96
O5—C16	1.226 (7)	C3—H3c	0.96
O6—C14	1.348 (8)	C4—H4a	0.96
O7—Sn1^i	2.154 (3)	C4—H4b	0.96
N1—C5	1.314 (7)	C4—H4c	0.96
N1—C9	1.346 (7)	C5—H5	0.93
N2—C11	1.325 (8)	C6—H6	0.93
N2—C15	1.337 (7)	C7—H7	0.93
C5—C6	1.395 (8)	C11—H11	0.93
C6—C7	1.368 (8)	C12—H12	0.93
C7—C8	1.376 (8)	C13—H13	0.93
C1—Sn1—C2	148.9 (3)	N1—C9—C10	116.3 (4)
C1—Sn1—N1	76.9 (2)	C8—C9—C10	121.2 (5)
C1—Sn1—O1	93.3 (2)	O2—C10—O1	123.8 (6)
C1—Sn1—O4^i	80.8 (2)	O2—C10—C9	117.8 (5)
C1—Sn1—O7	104.6 (2)	O1—C10—C9	118.3 (5)
C1—Sn1—O7^i	94.3 (2)	N2—C11—C12	124.6 (7)
C2—Sn1—N1	79.5 (2)	C13—C12—C11	118.0 (7)
C2—Sn1—O1	93.5 (2)	C12—C13—C14	118.9 (7)
C2—Sn1—O4^i	80.0 (2)	O6—C14—C15	123.0 (6)
C2—Sn1—O7^i	96.4 (2)	O6—C14—C13	118.7 (6)
C2—Sn1—O7	106.3 (2)	C15—C14—C13	118.3 (6)
N1—Sn1—O1	62.3 (1)	N2—C15—C14	123.0 (5)
N1—Sn1—O4^i	91.9 (1)	N2—C15—C16	116.2 (5)
N1—Sn1—O7	134.6 (1)	C14—C15—C16	120.7 (5)
N1—Sn1—O7^i	150.7 (1)	O5—C16—O4	125.4 (6)
O1—Sn1—O4^i	154.2 (1)	O5—C16—C15	118.6 (5)
O1—Sn1—O7	72.3 (1)	O4—C16—C15	116.0 (5)
O1—Sn1—O7^i	146.9 (1)	C8—O3—H3o	109.5
O4^i—Sn1—O7	133.5 (1)	C14—O6—H6o	109.5
O4^i—Sn1—O7^i	58.9 (1)	Sn1—C1—H1a	109.5
O7—Sn1—O7^i	74.6 (2)	Sn1—C1—H1b	109.5
C3—Sn2—C4	136.0 (3)	H1a—C1—H1b	109.5
C3—Sn2—N2	85.9 (2)	Sn1—C1—H1c	109.5
C3—Sn2—O1	83.7 (2)	H1a—C1—H1c	109.5
C3—Sn2—O4	108.6 (2)	H1b—C1—H1c	109.5
C3—Sn2—O7	104.7 (2)	Sn1—C2—H2a	109.5
C4—Sn2—N2	84.5 (3)	Sn1—C2—H2b	109.5
C4—Sn2—O1	81.3 (2)	H2a—C2—H2b	109.5
C4—Sn2—O4	107.1 (2)	Sn1—C2—H2c	109.5
C4—Sn2—O7	107.2 (3)	H2a—C2—H2c	109.5
N2—Sn2—O1	146.6 (1)	H2b—C2—H2c	109.5
N2—Sn2—O4	67.6 (1)	Sn2—C3—H3a	109.5
N2—Sn2—O7	145.8 (1)	Sn2—C3—H3b	109.5
O1—Sn2—O4	145.7 (1)	H3a—C3—H3b	109.5
O1—Sn2—O7	67.7 (1)	Sn2—C3—H3c	109.5
O4—Sn2—O7	78.2 (1)	H3a—C3—H3c	109.5
C10—O1—Sn1	132.0 (4)	H3b—C3—H3c	109.5
C10—O1—Sn2	132.4 (4)	Sn2—C4—H4a	109.5
Sn1—O1—Sn2	95.2 (1)	Sn2—C4—H4b	109.5
C16—O4—Sn2	128.8 (4)	H4a—C4—H4b	109.5
Sn2—O7—Sn1	124.8 (2)	Sn2—C4—H4c	109.5
Sn2—O7—Sn1^i	129.6 (2)	H4a—C4—H4c	109.5
Sn1—O7—Sn1^i	105.4 (2)	H4b—C4—H4c	109.5
C5—N1—C9	118.1 (4)	N1—C5—H5	118.4
C5—N1—Sn1	130.8 (4)	C6—C5—H5	118.4
C9—N1—Sn1	110.8 (3)	C7—C6—H6	120.8
C11—N2—C15	117.2 (6)	C5—C6—H6	120.8
C11—N2—Sn2	132.0 (5)	C6—C7—H7	120.2
C15—N2—Sn2	110.6 (3)	C8—C7—H7	120.2
N1—C5—C6	123.2 (5)	N2—C11—H11	117.7
C7—C6—C5	118.5 (6)	C12—C11—H11	117.7
C6—C7—C8	119.7 (5)	C13—C12—H12	121.0
O3—C8—C7	119.9 (5)	C11—C12—H12	121.0
O3—C8—C9	122.0 (5)	C12—C13—H13	120.5
C7—C8—C9	118.1 (5)	C14—C13—H13	120.5
N1—C9—C8	122.4 (5)
O7—Sn1—O1—C10	175.9 (5)	C1—Sn1—N1—C9	−97.2 (4)
C2—Sn1—O1—C10	−78.1 (5)	O7^i—Sn1—N1—C9	−172.3 (3)
C1—Sn1—O1—C10	71.6 (5)	O1—Sn1—N1—C9	3.6 (3)
O7^i—Sn1—O1—C10	174.5 (4)	O4^i—Sn1—N1—C9	−177.3 (4)
N1—Sn1—O1—C10	−1.8 (5)	O7—Sn2—N2—C11	176.6 (5)
O4^i—Sn1—O1—C10	−4.1 (7)	C3—Sn2—N2—C11	66.5 (7)
O7—Sn1—O1—Sn2	2.5 (1)	C4—Sn2—N2—C11	−70.5 (7)
C2—Sn1—O1—Sn2	108.5 (2)	O4—Sn2—N2—C11	178.5 (7)
C1—Sn1—O1—Sn2	−101.8 (2)	O1—Sn2—N2—C11	−5.5 (8)
O7^i—Sn1—O1—Sn2	1.1 (3)	O7—Sn2—N2—C15	−9.5 (6)
N1—Sn1—O1—Sn2	−175.2 (2)	C3—Sn2—N2—C15	−119.7 (4)
O4^i—Sn1—O1—Sn2	−177.5 (2)	C4—Sn2—N2—C15	103.3 (4)
O7—Sn2—O1—C10	−175.9 (5)	O4—Sn2—N2—C15	−7.6 (4)
C3—Sn2—O1—C10	−67.2 (5)	O1—Sn2—N2—C15	168.4 (3)
C4—Sn2—O1—C10	71.3 (5)	C9—N1—C5—C6	0.4 (9)
O4—Sn2—O1—C10	178.8 (4)	Sn1—N1—C5—C6	−172.2 (4)
N2—Sn2—O1—C10	5.3 (6)	N1—C5—C6—C7	0 (1)
O7—Sn2—O1—Sn1	−2.6 (1)	C5—C6—C7—C8	1 (1)
C3—Sn2—O1—Sn1	106.1 (2)	C6—C7—C8—O3	−179.4 (6)
C4—Sn2—O1—Sn1	−115.4 (3)	C6—C7—C8—C9	−0.5 (9)
O4—Sn2—O1—Sn1	−7.8 (3)	C5—N1—C9—C8	−0.4 (8)
N2—Sn2—O1—Sn1	178.7 (2)	Sn1—N1—C9—C8	173.6 (4)
O7—Sn2—O4—C16	−173.3 (5)	C5—N1—C9—C10	−179.1 (5)
C3—Sn2—O4—C16	85.1 (5)	Sn1—N1—C9—C10	−5.1 (6)
C4—Sn2—O4—C16	−68.6 (5)	O3—C8—C9—N1	179.3 (6)
O1—Sn2—O4—C16	−168.3 (4)	C7—C8—C9—N1	0.5 (9)
N2—Sn2—O4—C16	7.8 (4)	O3—C8—C9—C10	−2.0 (9)
C3—Sn2—O7—Sn1	−73.1 (3)	C7—C8—C9—C10	179.1 (5)
C4—Sn2—O7—Sn1	76.1 (3)	Sn1—O1—C10—O2	−177.5 (4)
O4—Sn2—O7—Sn1	−179.4 (3)	Sn2—O1—C10—O2	−6.5 (9)
O1—Sn2—O7—Sn1	3.56 (18)	Sn1—O1—C10—C9	−0.2 (8)
N2—Sn2—O7—Sn1	−177.7 (2)	Sn2—O1—C10—C9	170.8 (3)
C3—Sn2—O7—Sn1^i	101.2 (3)	N1—C9—C10—O2	−178.3 (5)
C4—Sn2—O7—Sn1^i	−109.6 (3)	C8—C9—C10—O2	3.0 (8)
O4—Sn2—O7—Sn1^i	−5.2 (2)	N1—C9—C10—O1	4.2 (8)
O1—Sn2—O7—Sn1^i	177.8 (3)	C8—C9—C10—O1	−174.5 (5)
N2—Sn2—O7—Sn1^i	−3.4 (4)	C15—N2—C11—C12	−1 (1)
C2—Sn1—O7—Sn2	−92.3 (3)	Sn2—N2—C11—C12	172.5 (6)
C1—Sn1—O7—Sn2	85.0 (3)	N2—C11—C12—C13	−1 (1)
O7^i—Sn1—O7—Sn2	175.4 (3)	C11—C12—C13—C14	4 (1)
O1—Sn1—O7—Sn2	−3.8 (2)	C12—C13—C14—O6	177.8 (7)
N1—Sn1—O7—Sn2	−0.9 (3)	C12—C13—C14—C15	−5 (1)
O4^i—Sn1—O7—Sn2	176.2 (2)	C11—N2—C15—C14	0.2 (9)
C2—Sn1—O7—Sn1^i	92.3 (2)	Sn2—N2—C15—C14	−174.6 (5)
C1—Sn1—O7—Sn1^i	−90.4 (2)	C11—N2—C15—C16	−177.5 (6)
O7^i—Sn1—O7—Sn1^i	0.0	Sn2—N2—C15—C16	7.6 (6)
O1—Sn1—O7—Sn1^i	−179.2 (2)	O6—C14—C15—N2	−179.8 (6)
N1—Sn1—O7—Sn1^i	−176.4 (1)	C13—C14—C15—N2	3 (1)
O4^i—Sn1—O7—Sn1^i	0.7 (3)	O6—C14—C15—C16	−2.2 (9)
O7—Sn1—N1—C5	173.5 (5)	C13—C14—C15—C16	−179.9 (6)
C2—Sn1—N1—C5	−83.8 (5)	Sn2—O4—C16—O5	172.4 (4)
C1—Sn1—N1—C5	75.8 (5)	Sn2—O4—C16—C15	−6.5 (7)
O7^i—Sn1—N1—C5	0.7 (7)	N2—C15—C16—O5	178.6 (5)
O1—Sn1—N1—C5	176.6 (6)	C14—C15—C16—O5	0.8 (9)
O4^i—Sn1—N1—C5	−4.4 (5)	N2—C15—C16—O4	−2.4 (8)
O7—Sn1—N1—C9	0.5 (5)	C14—C15—C16—O4	179.8 (5)
C2—Sn1—N1—C9	103.2 (4)

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
O3—H3o···O2	0.82	1.84	2.561 (6)	146
O6—H6o···O5	0.82	1.95	2.579 (6)	133