The dinuclear title compound, [Sn2(CH3)2(C6H5)2(C7H3NO4)2(H2O)2]·2CHCl3, crystallizes as a dichloroform solvate; the centrosymmetric compound has Sn in a seven-coordinate, trans-pentagonal–bipyramidal geometry. The dicarboxylate unit is tetradentate; it binds through the N and the two O atoms (one from the dianion); one of the O atoms that is involved in coordination forms a bridge to the other Sn atom.
Supporting information
CCDC reference: 640479
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.007 Å
- H-atom completeness 94%
- R factor = 0.046
- wR factor = 0.132
- Data-to-parameter ratio = 23.1
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.499 0.964
Tmin(prime) and Tmax expected: 0.570 0.964
RR(prime) = 0.876
Please check that your absorption correction is appropriate.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C15
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C30 H30 Cl6 N2 O10 Sn2
Atom count from the _atom_site data: C30 H28 Cl6 N2 O10 Sn2
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
From the CIF: _cell_formula_units_Z 4
From the CIF: _chemical_formula_sum C30 H30 Cl6 N2 O10 Sn2
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 120.00 120.00 0.00
H 120.00 112.00 8.00
Cl 24.00 24.00 0.00
N 8.00 8.00 0.00
O 40.00 40.00 0.00
Sn 8.00 8.00 0.00
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
5 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
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX-II software (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.
Bis[aquamethylphenyl(µ-pyridine-2,6-dicarboxylato-
κ4O,
N,
O':
O'')tin(IV)] chloroform disolvate
top
Crystal data top
[Sn2(CH3)2(C6H5)2(C7H3NO4)2(H2O)2]·2CHCl3 | F(000) = 2024 |
Mr = 1028.64 | Dx = 1.851 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 8494 reflections |
a = 22.7306 (3) Å | θ = 2.5–32.4° |
b = 10.6253 (2) Å | µ = 1.84 mm−1 |
c = 17.1579 (3) Å | T = 173 K |
β = 117.028 (1)° | Plate, colorless |
V = 3691.4 (1) Å3 | 0.30 × 0.18 × 0.02 mm |
Z = 4 | |
Data collection top
Bruker APEX-II diffractometer | 5278 independent reflections |
Radiation source: medium-focus sealed tube | 3763 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
φ and ω scans | θmax = 30.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −21→31 |
Tmin = 0.499, Tmax = 0.964 | k = −14→14 |
17272 measured reflections | l = −21→24 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0696P)2 + 5.0368P] where P = (Fo2 + 2Fc2)/3 |
5278 reflections | (Δ/σ)max = 0.001 |
228 parameters | Δρmax = 1.90 e Å−3 |
18 restraints | Δρmin = −1.87 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Sn1 | 0.409535 (14) | 0.46852 (3) | 0.39391 (2) | 0.01197 (10) | |
Cl1 | 0.70349 (9) | 0.0009 (3) | 0.86528 (18) | 0.0937 (11) | |
Cl2 | 0.57639 (10) | −0.08996 (18) | 0.74369 (14) | 0.0533 (5) | |
Cl3 | 0.58658 (12) | 0.15302 (19) | 0.82199 (13) | 0.0599 (5) | |
O1w | 0.37540 (15) | 0.6425 (3) | 0.3100 (2) | 0.0162 (7) | |
H1w1 | 0.4025 | 0.7010 | 0.3338 | 0.024* | |
H1w2 | 0.3381 | 0.6640 | 0.3044 | 0.024* | |
O1 | 0.31310 (15) | 0.4203 (3) | 0.2870 (2) | 0.0152 (6) | |
O2 | 0.23007 (16) | 0.2842 (3) | 0.2259 (2) | 0.0210 (7) | |
O3 | 0.49671 (15) | 0.3700 (3) | 0.5217 (2) | 0.0154 (6) | |
O4 | 0.53426 (16) | 0.1900 (3) | 0.5961 (2) | 0.0217 (8) | |
N1 | 0.38628 (17) | 0.2634 (4) | 0.4086 (2) | 0.0138 (8) | |
C1 | 0.4664 (2) | 0.4262 (5) | 0.3288 (3) | 0.0197 (10) | |
H1a | 0.4371 | 0.4048 | 0.2677 | 0.030* | |
H1b | 0.4954 | 0.3546 | 0.3575 | 0.030* | |
H1c | 0.4933 | 0.4995 | 0.3309 | 0.030* | |
C2 | 0.3729 (2) | 0.5355 (4) | 0.4802 (3) | 0.0151 (8) | |
C3 | 0.3606 (3) | 0.6632 (5) | 0.4839 (4) | 0.0232 (10) | |
H3 | 0.3695 | 0.7209 | 0.4483 | 0.028* | |
C4 | 0.3355 (3) | 0.7071 (5) | 0.5393 (4) | 0.0304 (12) | |
H4 | 0.3268 | 0.7943 | 0.5403 | 0.036* | |
C5 | 0.3232 (3) | 0.6259 (6) | 0.5924 (4) | 0.0300 (13) | |
H5 | 0.3061 | 0.6567 | 0.6299 | 0.036* | |
C6 | 0.3360 (3) | 0.4987 (5) | 0.5907 (4) | 0.0277 (12) | |
H6 | 0.3277 | 0.4418 | 0.6273 | 0.033* | |
C7 | 0.3611 (2) | 0.4544 (5) | 0.5351 (3) | 0.0222 (10) | |
H7 | 0.3703 | 0.3673 | 0.5348 | 0.027* | |
C8 | 0.2858 (2) | 0.3139 (4) | 0.2822 (3) | 0.0150 (9) | |
C9 | 0.3279 (2) | 0.2182 (4) | 0.3504 (3) | 0.0153 (9) | |
C10 | 0.3089 (2) | 0.0948 (4) | 0.3532 (3) | 0.0176 (9) | |
H10 | 0.2671 | 0.0645 | 0.3113 | 0.021* | |
C11 | 0.3529 (2) | 0.0167 (4) | 0.4190 (3) | 0.0199 (10) | |
H11 | 0.3412 | −0.0681 | 0.4228 | 0.024* | |
C12 | 0.4149 (2) | 0.0642 (4) | 0.4800 (3) | 0.0185 (10) | |
H12 | 0.4460 | 0.0122 | 0.5248 | 0.022* | |
C13 | 0.4287 (2) | 0.1886 (4) | 0.4724 (3) | 0.0151 (9) | |
C14 | 0.4924 (2) | 0.2531 (4) | 0.5364 (3) | 0.0145 (9) | |
C15 | 0.6265 (3) | 0.0445 (6) | 0.7850 (4) | 0.0338 (13) | |
H15 | 0.6323 | 0.0843 | 0.7361 | 0.041* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn1 | 0.00812 (14) | 0.01176 (15) | 0.01533 (15) | 0.00030 (11) | 0.00471 (11) | −0.00010 (13) |
Cl1 | 0.0227 (9) | 0.146 (2) | 0.0909 (18) | −0.0047 (11) | 0.0071 (10) | 0.0816 (18) |
Cl2 | 0.0594 (11) | 0.0372 (9) | 0.0802 (14) | −0.0084 (8) | 0.0464 (11) | −0.0053 (9) |
Cl3 | 0.1001 (16) | 0.0453 (11) | 0.0553 (11) | −0.0027 (10) | 0.0538 (12) | −0.0084 (9) |
O1w | 0.0106 (15) | 0.0164 (16) | 0.0191 (16) | −0.0010 (12) | 0.0046 (13) | 0.0006 (13) |
O1 | 0.0109 (15) | 0.0149 (15) | 0.0171 (16) | −0.0002 (12) | 0.0040 (13) | 0.0016 (13) |
O2 | 0.0123 (16) | 0.0194 (18) | 0.0234 (18) | −0.0009 (12) | 0.0013 (14) | 0.0020 (14) |
O3 | 0.0123 (15) | 0.0116 (15) | 0.0194 (16) | −0.0010 (11) | 0.0048 (13) | −0.0008 (13) |
O4 | 0.0145 (16) | 0.0155 (17) | 0.0247 (18) | −0.0008 (12) | −0.0002 (15) | 0.0023 (14) |
N1 | 0.0083 (17) | 0.0131 (18) | 0.0167 (19) | 0.0012 (13) | 0.0029 (15) | −0.0011 (15) |
C1 | 0.018 (2) | 0.019 (2) | 0.025 (2) | 0.0006 (17) | 0.012 (2) | −0.0013 (19) |
C2 | 0.0101 (19) | 0.016 (2) | 0.016 (2) | −0.0004 (16) | 0.0034 (17) | 0.0017 (18) |
C3 | 0.026 (3) | 0.019 (2) | 0.028 (3) | 0.0041 (19) | 0.016 (2) | 0.002 (2) |
C4 | 0.040 (3) | 0.023 (3) | 0.032 (3) | 0.013 (2) | 0.019 (3) | −0.002 (2) |
C5 | 0.028 (3) | 0.039 (3) | 0.029 (3) | 0.010 (2) | 0.018 (2) | 0.000 (2) |
C6 | 0.026 (3) | 0.033 (3) | 0.027 (3) | 0.001 (2) | 0.015 (2) | 0.003 (2) |
C7 | 0.018 (2) | 0.022 (3) | 0.027 (3) | 0.0020 (18) | 0.010 (2) | 0.003 (2) |
C8 | 0.010 (2) | 0.014 (2) | 0.020 (2) | 0.0009 (15) | 0.0058 (18) | 0.0010 (17) |
C9 | 0.010 (2) | 0.015 (2) | 0.020 (2) | −0.0012 (15) | 0.0061 (18) | −0.0025 (18) |
C10 | 0.015 (2) | 0.011 (2) | 0.025 (2) | −0.0030 (16) | 0.0067 (19) | −0.0042 (18) |
C11 | 0.022 (2) | 0.007 (2) | 0.027 (3) | −0.0037 (17) | 0.008 (2) | 0.0016 (18) |
C12 | 0.017 (2) | 0.014 (2) | 0.022 (2) | −0.0003 (16) | 0.006 (2) | −0.0014 (17) |
C13 | 0.011 (2) | 0.015 (2) | 0.018 (2) | 0.0009 (15) | 0.0051 (18) | 0.0001 (17) |
C14 | 0.013 (2) | 0.012 (2) | 0.019 (2) | −0.0022 (15) | 0.0078 (18) | −0.0023 (17) |
C15 | 0.027 (3) | 0.038 (3) | 0.038 (3) | 0.002 (2) | 0.017 (3) | 0.011 (3) |
Geometric parameters (Å, º) top
Sn1—C1 | 2.106 (5) | C2—C7 | 1.389 (7) |
Sn1—C2 | 2.125 (5) | C2—C3 | 1.392 (7) |
Sn1—O1 | 2.186 (3) | C3—C4 | 1.392 (7) |
Sn1—N1 | 2.283 (4) | C3—H3 | 0.9500 |
Sn1—O3 | 2.425 (3) | C4—C5 | 1.372 (8) |
Sn1—O3i | 2.604 (3) | C4—H4 | 0.9500 |
Sn1—O1w | 2.253 (3) | C5—C6 | 1.384 (8) |
Cl1—C15 | 1.727 (6) | C5—H5 | 0.9500 |
Cl2—C15 | 1.763 (7) | C6—C7 | 1.399 (8) |
Cl3—C15 | 1.755 (7) | C6—H6 | 0.9500 |
O1w—H1w1 | 0.8400 | C7—H7 | 0.9500 |
O1w—H1w2 | 0.8400 | C8—C9 | 1.516 (6) |
O1—C8 | 1.274 (5) | C9—C10 | 1.388 (6) |
O2—C8 | 1.236 (5) | C10—C11 | 1.391 (7) |
O3—C14 | 1.280 (5) | C10—H10 | 0.9500 |
O4—C14 | 1.232 (5) | C11—C12 | 1.413 (7) |
N1—C9 | 1.336 (5) | C11—H11 | 0.9500 |
N1—C13 | 1.342 (6) | C12—C13 | 1.378 (6) |
C1—H1a | 0.9800 | C12—H12 | 0.9500 |
C1—H1b | 0.9800 | C13—C14 | 1.525 (6) |
C1—H1C | 0.9800 | C15—H15 | 1.0000 |
| | | |
C1—Sn1—C2 | 166.2 (2) | C4—C3—H3 | 119.7 |
C1—Sn1—N1 | 94.8 (2) | C5—C4—C3 | 120.8 (5) |
C1—Sn1—O1 | 97.4 (2) | C5—C4—H4 | 119.6 |
C1—Sn1—O3i | 83.8 (2) | C3—C4—H4 | 119.6 |
C1—Sn1—O3 | 86.6 (2) | C4—C5—C6 | 119.5 (5) |
C1—Sn1—O1w | 87.3 (2) | C4—C5—H5 | 120.2 |
C2—Sn1—O3 | 86.1 (1) | C6—C5—H5 | 120.2 |
C2—Sn1—O3i | 82.7 (1) | C5—C6—C7 | 119.7 (5) |
C2—Sn1—O1w | 92.3 (2) | C5—C6—H6 | 120.1 |
C2—Sn1—N1 | 93.4 (2) | C7—C6—H6 | 120.1 |
C2—Sn1—O1 | 95.9 (2) | C2—C7—C6 | 121.2 (5) |
N1—Sn1—O1 | 71.0 (1) | C2—C7—H7 | 119.4 |
N1—Sn1—O3 | 67.9 (1) | C6—C7—H7 | 119.4 |
N1—Sn1—O3i | 137.7 (1) | O2—C8—O1 | 125.0 (4) |
N1—Sn1—O1w | 145.5 (1) | O2—C8—C9 | 119.7 (4) |
O1—Sn1—O1w | 74.5 (1) | O1—C8—C9 | 115.3 (4) |
O1—Sn1—O3 | 138.9 (1) | N1—C9—C10 | 122.2 (4) |
O1—Sn1—O3i | 151.2 (1) | N1—C9—C8 | 113.5 (4) |
O3—Sn1—O3i | 69.9 (1) | C10—C9—C8 | 124.3 (4) |
O3—Sn1—O1w | 146.6 (1) | C9—C10—C11 | 118.2 (4) |
O3i—Sn1—O1w | 76.8 (1) | C9—C10—H10 | 120.9 |
Sn1—O1w—H1w1 | 109.5 | C11—C10—H10 | 120.9 |
Sn1—O1w—H1w2 | 109.5 | C10—C11—C12 | 119.6 (4) |
H1w1—O1w—H1w2 | 109.5 | C10—C11—H11 | 120.2 |
C8—O1—Sn1 | 122.3 (3) | C12—C11—H11 | 120.2 |
C14—O3—Sn1 | 119.5 (3) | C13—C12—C11 | 117.8 (4) |
C9—N1—C13 | 119.9 (4) | C13—C12—H12 | 121.1 |
C9—N1—Sn1 | 117.5 (3) | C11—C12—H12 | 121.1 |
C13—N1—Sn1 | 122.6 (3) | N1—C13—C12 | 122.3 (4) |
Sn1—C1—H1a | 109.5 | N1—C13—C14 | 114.6 (4) |
Sn1—C1—H1b | 109.5 | C12—C13—C14 | 123.0 (4) |
H1a—C1—H1b | 109.5 | O4—C14—O3 | 126.3 (4) |
Sn1—C1—H1C | 109.5 | O4—C14—C13 | 118.4 (4) |
H1a—C1—H1C | 109.5 | O3—C14—C13 | 115.2 (4) |
H1b—C1—H1C | 109.5 | Cl1—C15—Cl3 | 113.0 (4) |
C7—C2—C3 | 118.0 (5) | Cl1—C15—Cl2 | 109.8 (4) |
C7—C2—Sn1 | 121.4 (4) | Cl3—C15—Cl2 | 109.4 (3) |
C3—C2—Sn1 | 120.5 (4) | Cl1—C15—H15 | 108.2 |
C2—C3—C4 | 120.7 (5) | Cl3—C15—H15 | 108.2 |
C2—C3—H3 | 119.7 | Cl2—C15—H15 | 108.2 |
| | | |
C1—Sn1—O1—C8 | 97.2 (4) | O3i—Sn1—C2—C3 | 56.4 (4) |
C2—Sn1—O1—C8 | −86.9 (4) | C7—C2—C3—C4 | −1.9 (7) |
O1w—Sn1—O1—C8 | −177.7 (4) | Sn1—C2—C3—C4 | 178.9 (4) |
N1—Sn1—O1—C8 | 4.7 (3) | C2—C3—C4—C5 | 1.0 (9) |
O3—Sn1—O1—C8 | 3.9 (4) | C3—C4—C5—C6 | 0.0 (9) |
O3i—Sn1—O1—C8 | −172.4 (3) | C4—C5—C6—C7 | 0.0 (8) |
C1—Sn1—O3—C14 | −93.0 (4) | C3—C2—C7—C6 | 1.8 (7) |
C2—Sn1—O3—C14 | 98.8 (3) | Sn1—C2—C7—C6 | −178.9 (4) |
O1—Sn1—O3—C14 | 4.3 (4) | C5—C6—C7—C2 | −0.9 (8) |
O1w—Sn1—O3—C14 | −172.9 (3) | Sn1—O1—C8—O2 | 176.0 (4) |
N1—Sn1—O3—C14 | 3.5 (3) | Sn1—O1—C8—C9 | −6.0 (6) |
O3i—Sn1—O3—C14 | −177.6 (4) | C13—N1—C9—C10 | −0.2 (7) |
C1—Sn1—N1—C9 | −98.5 (4) | Sn1—N1—C9—C10 | 179.7 (4) |
C2—Sn1—N1—C9 | 92.7 (3) | C13—N1—C9—C8 | −179.6 (4) |
O1—Sn1—N1—C9 | −2.3 (3) | Sn1—N1—C9—C8 | 0.3 (5) |
O1w—Sn1—N1—C9 | −6.3 (5) | O2—C8—C9—N1 | −178.5 (4) |
O3—Sn1—N1—C9 | 177.1 (4) | O1—C8—C9—N1 | 3.5 (6) |
O3i—Sn1—N1—C9 | 175.6 (3) | O2—C8—C9—C10 | 2.2 (7) |
C1—Sn1—N1—C13 | 81.4 (4) | O1—C8—C9—C10 | −175.9 (5) |
C2—Sn1—N1—C13 | −87.4 (4) | N1—C9—C10—C11 | −0.1 (7) |
O1—Sn1—N1—C13 | 177.6 (4) | C8—C9—C10—C11 | 179.2 (4) |
O1w—Sn1—N1—C13 | 173.6 (3) | C9—C10—C11—C12 | −0.4 (7) |
O3—Sn1—N1—C13 | −2.9 (3) | C10—C11—C12—C13 | 1.3 (8) |
O3i—Sn1—N1—C13 | −4.5 (4) | C9—N1—C13—C12 | 1.1 (7) |
C1—Sn1—C2—C7 | −111.3 (8) | Sn1—N1—C13—C12 | −178.8 (4) |
O1—Sn1—C2—C7 | 86.1 (4) | C9—N1—C13—C14 | −177.8 (4) |
O1w—Sn1—C2—C7 | 160.7 (4) | Sn1—N1—C13—C14 | 2.3 (5) |
N1—Sn1—C2—C7 | 14.8 (4) | C11—C12—C13—N1 | −1.6 (7) |
O3—Sn1—C2—C7 | −52.7 (4) | C11—C12—C13—C14 | 177.2 (4) |
O3i—Sn1—C2—C7 | −122.9 (4) | Sn1—O3—C14—O4 | 176.4 (4) |
C1—Sn1—C2—C3 | 68.0 (9) | Sn1—O3—C14—C13 | −3.6 (5) |
O1—Sn1—C2—C3 | −94.7 (4) | N1—C13—C14—O4 | −179.0 (4) |
O1w—Sn1—C2—C3 | −20.0 (4) | C12—C13—C14—O4 | 2.1 (7) |
N1—Sn1—C2—C3 | −165.9 (4) | N1—C13—C14—O3 | 1.0 (6) |
O3—Sn1—C2—C3 | 126.6 (4) | C12—C13—C14—O3 | −177.9 (5) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w2···O2ii | 0.84 | 1.89 | 2.656 (5) | 151 |
O1w—H1w1···O4i | 0.84 | 1.81 | 2.641 (4) | 169 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y+1/2, −z+1/2. |