In the title complex, [Sn
2(CH
3)
4(C
8H
6N
2O
4)
2(CH
4O)
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.
Supporting information
CCDC reference: 613747
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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)]
top
Crystal data top
[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) Å3 | 0.23 × 0.15 × 0.12 mm |
Z = 8 | |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0451P)2 + 1.0171P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—O1i | 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—O1i | 82.67 (19) | C8—C7—H8 | 126.3 |
C10—Sn1—O1i | 81.61 (17) | C6—C7—H8 | 126.3 |
O3—Sn1—O1i | 153.79 (11) | C7—C8—O4 | 110.3 (5) |
N1—Sn1—O1i | 136.11 (13) | C7—C8—H7 | 124.9 |
O1—Sn1—O1i | 66.51 (12) | O4—C8—H7 | 124.9 |
O5—Sn1—O1i | 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) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H1···O2i | 0.84 (6) | 1.82 (6) | 2.643 (6) | 166 (6) |
Symmetry code: (i) −x, −y+2, −z. |