Bis­[μ-furan-2-carbaldehyde (1-carboxyethylidene)hydrazonato(2–)]bis­[methanoldimethyl­tin(IV)]

In the title complex, [Sn₂(CH₃)₄(C₈H₆N₂O₄)₂(CH₄O)₂], each Sn^IV ion exists in a distorted penta­gonal–bipyramidal coordination environment, coordinated by three O atoms and one N atom from the pyruvic acid 2-furoic acid hydrazone ligands, one O atom from a methanol mol­ecule and two axial C atoms from trans methyl groups, thus forming a dimeric mol­ecule, which has crystallographic symmetry. In the dimeric structure there are also intra­molecular hydrogen bonds, which contribute to the crystal stability and compactness.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.037
• wR factor = 0.091
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O1     ..  O1      ..       2.80 Ang.

Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O4

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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

Bis[µ-pyruvic acid 2-furoic acid hydrazonato(2-)]bis[methanolbismethyltin(IV)]

Crystal data

[Sn2(CH3)4(C8H6N2O4)2(CH4O)2]	F(000) = 1488
Mr = 374.95	Dx = 1.752 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2118 reflections
a = 20.794 (19) Å	θ = 2.3–22.8°
b = 9.911 (9) Å	µ = 1.81 mm^−1
c = 14.142 (13) Å	T = 298 K
β = 102.658 (15)°	Block, colorless
V = 2844 (5) Å^3	0.23 × 0.15 × 0.12 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer	2538 independent reflections
Radiation source: fine-focus sealed tube	1798 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→17
Tmin = 0.680, Tmax = 0.812	k = −11→11
7350 measured reflections	l = −16→14

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) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0451P)^2 + 1.0171P] where P = (Fo^2 + 2Fc^2)/3
2538 reflections	(Δ/σ)max = 0.011
180 parameters	Δρmax = 0.64 e Å^−3
0 restraints	Δρmin = −0.40 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	0.067287 (17)	0.83762 (3)	0.03589 (3)	0.04206 (16)
N1	0.0107 (2)	0.6685 (4)	0.0856 (3)	0.0395 (10)
N2	0.0426 (2)	0.5493 (4)	0.1158 (3)	0.0428 (11)
O1	−0.04143 (16)	0.9006 (3)	0.0242 (3)	0.0455 (9)
O2	−0.13657 (18)	0.8428 (3)	0.0614 (3)	0.0556 (11)
O3	0.13082 (17)	0.6622 (3)	0.0738 (3)	0.0522 (10)
O4	0.2064 (2)	0.4381 (4)	0.1163 (3)	0.0724 (13)
O5	0.1720 (2)	0.9157 (5)	0.0109 (4)	0.0709 (14)
C1	−0.0791 (3)	0.8192 (5)	0.0564 (4)	0.0422 (13)
C2	−0.0501 (2)	0.6837 (5)	0.0912 (4)	0.0389 (12)
C3	−0.0898 (3)	0.5816 (5)	0.1295 (4)	0.0536 (15)
H3A	−0.1309	0.5682	0.0840	0.080*
H3B	−0.0981	0.6124	0.1901	0.080*
H3C	−0.0659	0.4979	0.1395	0.080*
C4	0.1042 (3)	0.5585 (5)	0.1061 (4)	0.0431 (13)
C5	0.1460 (2)	0.4422 (5)	0.1386 (4)	0.0405 (12)
C6	0.1358 (3)	0.3325 (5)	0.1866 (4)	0.0462 (14)
H6	0.0982	0.3111	0.2089	0.055*
C7	0.1938 (3)	0.2544 (6)	0.1969 (5)	0.0641 (18)
H8	0.2019	0.1719	0.2287	0.077*
C8	0.2340 (3)	0.3194 (7)	0.1536 (5)	0.0710 (19)
H7	0.2755	0.2890	0.1490	0.085*
C9	0.0925 (3)	0.9279 (6)	0.1719 (4)	0.0590 (16)
H9A	0.0987	1.0230	0.1645	0.089*
H9B	0.1327	0.8889	0.2082	0.089*
H9C	0.0579	0.9135	0.2059	0.089*
C11	0.2351 (3)	0.9034 (7)	0.0696 (5)	0.081 (2)
H11A	0.2492	0.9892	0.0981	0.121*
H11B	0.2651	0.8736	0.0311	0.121*
H11C	0.2343	0.8388	0.1199	0.121*
H1	0.164 (3)	0.989 (6)	−0.019 (4)	0.07 (2)*
C10	0.0477 (3)	0.8044 (5)	−0.1142 (4)	0.0567 (16)
H10A	0.0189	0.7282	−0.1302	0.085*
H10B	0.0883	0.7869	−0.1339	0.085*
H10C	0.0271	0.8829	−0.1474	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0387 (2)	0.0409 (2)	0.0486 (3)	0.00048 (17)	0.01401 (17)	0.00507 (19)
N1	0.043 (3)	0.035 (2)	0.043 (3)	0.000 (2)	0.015 (2)	0.002 (2)
N2	0.038 (3)	0.037 (2)	0.054 (3)	0.0021 (19)	0.013 (2)	0.009 (2)
O1	0.039 (2)	0.040 (2)	0.062 (3)	−0.0016 (16)	0.0197 (18)	0.0076 (18)
O2	0.040 (2)	0.052 (2)	0.080 (3)	0.0078 (18)	0.026 (2)	0.021 (2)
O3	0.042 (2)	0.046 (2)	0.074 (3)	0.0056 (17)	0.023 (2)	0.018 (2)
O4	0.058 (3)	0.068 (3)	0.100 (4)	0.009 (2)	0.036 (3)	0.021 (3)
O5	0.040 (3)	0.059 (3)	0.114 (4)	−0.002 (2)	0.018 (2)	0.035 (3)
C1	0.035 (3)	0.043 (3)	0.049 (3)	0.000 (2)	0.010 (3)	0.000 (3)
C2	0.041 (3)	0.039 (3)	0.037 (3)	−0.002 (2)	0.009 (2)	−0.001 (2)
C3	0.042 (3)	0.047 (3)	0.075 (5)	−0.005 (3)	0.021 (3)	0.009 (3)
C4	0.042 (3)	0.048 (3)	0.042 (3)	0.005 (2)	0.013 (3)	0.006 (3)
C5	0.037 (3)	0.050 (3)	0.035 (3)	0.005 (2)	0.010 (2)	0.004 (3)
C6	0.036 (3)	0.043 (3)	0.059 (4)	0.004 (3)	0.010 (3)	0.010 (3)
C7	0.069 (4)	0.042 (4)	0.078 (5)	0.002 (3)	0.010 (4)	0.008 (3)
C8	0.047 (4)	0.068 (5)	0.097 (6)	0.018 (3)	0.013 (4)	0.006 (4)
C9	0.066 (4)	0.059 (4)	0.050 (4)	−0.003 (3)	0.008 (3)	−0.005 (3)
C11	0.060 (5)	0.085 (5)	0.097 (6)	0.000 (4)	0.015 (4)	0.021 (5)
C10	0.070 (4)	0.053 (4)	0.051 (4)	0.008 (3)	0.022 (3)	0.006 (3)

Geometric parameters (Å, º)

Sn1—C9	2.082 (6)	C3—H3A	0.9600
Sn1—C10	2.098 (6)	C3—H3B	0.9600
Sn1—O3	2.178 (4)	C3—H3C	0.9600
Sn1—N1	2.248 (4)	C4—C5	1.457 (7)
Sn1—O1	2.316 (4)	C5—C6	1.323 (7)
Sn1—O5	2.409 (4)	C6—C7	1.412 (7)
Sn1—O1^i	2.747 (4)	C6—H6	0.9300
N1—C2	1.292 (6)	C7—C8	1.310 (8)
N1—N2	1.377 (5)	C7—H8	0.9300
N2—C4	1.320 (6)	C8—H7	0.9300
O1—C1	1.276 (6)	C9—H9A	0.9600
O2—C1	1.235 (6)	C9—H9B	0.9600
O3—C4	1.297 (6)	C9—H9C	0.9600
O4—C5	1.361 (6)	C11—H11A	0.9600
O4—C8	1.364 (7)	C11—H11B	0.9600
O5—C11	1.396 (7)	C11—H11C	0.9600
O5—H1	0.84 (6)	C10—H10A	0.9600
C1—C2	1.509 (7)	C10—H10B	0.9600
C2—C3	1.481 (6)	C10—H10C	0.9600
C9—Sn1—C10	163.0 (2)	C2—C3—H3B	109.5
C9—Sn1—O3	95.7 (2)	H3A—C3—H3B	109.5
C10—Sn1—O3	95.53 (19)	C2—C3—H3C	109.5
C9—Sn1—N1	94.3 (2)	H3A—C3—H3C	109.5
C10—Sn1—N1	101.60 (19)	H3B—C3—H3C	109.5
O3—Sn1—N1	70.06 (15)	O3—C4—N2	126.2 (5)
C9—Sn1—O1	89.70 (19)	O3—C4—C5	117.8 (4)
C10—Sn1—O1	90.02 (19)	N2—C4—C5	115.9 (4)
O3—Sn1—O1	139.69 (12)	C6—C5—O4	110.7 (4)
N1—Sn1—O1	69.71 (14)	C6—C5—C4	131.4 (5)
C9—Sn1—O5	86.8 (2)	O4—C5—C4	117.9 (4)
C10—Sn1—O5	83.3 (2)	C5—C6—C7	106.0 (5)
O3—Sn1—O5	76.92 (15)	C5—C6—H6	127.0
N1—Sn1—O5	146.91 (15)	C7—C6—H6	127.0
O1—Sn1—O5	143.37 (15)	C8—C7—C6	107.5 (5)
C9—Sn1—O1^i	82.67 (19)	C8—C7—H8	126.3
C10—Sn1—O1^i	81.61 (17)	C6—C7—H8	126.3
O3—Sn1—O1^i	153.79 (11)	C7—C8—O4	110.3 (5)
N1—Sn1—O1^i	136.11 (13)	C7—C8—H7	124.9
O1—Sn1—O1^i	66.51 (12)	O4—C8—H7	124.9
O5—Sn1—O1^i	76.88 (13)	Sn1—C9—H9A	109.5
C2—N1—N2	119.6 (4)	Sn1—C9—H9B	109.5
C2—N1—Sn1	121.2 (3)	H9A—C9—H9B	109.5
N2—N1—Sn1	119.1 (3)	Sn1—C9—H9C	109.5
C4—N2—N1	108.7 (4)	H9A—C9—H9C	109.5
C1—O1—Sn1	118.1 (3)	H9B—C9—H9C	109.5
C4—O3—Sn1	115.9 (3)	O5—C11—H11A	109.5
C5—O4—C8	105.6 (4)	O5—C11—H11B	109.5
C11—O5—Sn1	130.3 (4)	H11A—C11—H11B	109.5
C11—O5—H1	115 (4)	O5—C11—H11C	109.5
Sn1—O5—H1	106 (4)	H11A—C11—H11C	109.5
O2—C1—O1	125.3 (5)	H11B—C11—H11C	109.5
O2—C1—C2	118.2 (5)	Sn1—C10—H10A	109.5
O1—C1—C2	116.5 (4)	Sn1—C10—H10B	109.5
N1—C2—C3	124.9 (5)	H10A—C10—H10B	109.5
N1—C2—C1	114.2 (4)	Sn1—C10—H10C	109.5
C3—C2—C1	120.9 (4)	H10A—C10—H10C	109.5
C2—C3—H3A	109.5	H10B—C10—H10C	109.5

Symmetry code: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1···O2^i	0.84 (6)	1.82 (6)	2.643 (6)	166 (6)

Symmetry code: (i) −x, −y+2, −z.