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The crystal structure of the title compound, (C6H16N)[SnCl2(CH3)(C5H6O4)], is composed of strongly hydrogen-bonded pairs of anions and cations. The metal centre exhibits a distorted trigonal-bipyramidal geometry, with inequivalent Sn—Cl distances of 2.5252 (4) and 2.3954 (4) Å, identical Sn—C distances within 3σ limits [mean 2.107 (3) Å] and an Sn—O distance of 2.3077 (13) Å. The carboxyacrylate ligand forms an essentially planar seven-membered ring involving an intramolecular hydrogen bond.
Supporting information
CCDC reference: 189298
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.020
- wR factor = 0.048
- Data-to-parameter ratio = 15.7
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
(C6H16N)[SnCl2(CH3)(C6H6O4)] | F(000) = 440 |
Mr = 436.92 | Dx = 1.609 Mg m−3 |
Triclinic, P1 | Melting point: 333 K |
a = 8.9962 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.1856 (2) Å | Cell parameters from 7194 reflections |
c = 10.8439 (3) Å | θ = 1.0–27.4° |
α = 69.9082 (9)° | µ = 1.72 mm−1 |
β = 83.7866 (10)° | T = 173 K |
γ = 75.1111 (13)° | Prism, colourless |
V = 901.63 (4) Å3 | 0.25 × 0.20 × 0.15 mm |
Z = 2 | |
Data collection top
Nonius KappaCCD diffractometer | 4031 independent reflections |
Radiation source: fine-focus sealed tube | 3828 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ω and φ scans | θmax = 27.4°, θmin = 3.5° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −11→11 |
Tmin = 0.673, Tmax = 0.782 | k = −13→13 |
7194 measured reflections | l = −14→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)] = 0.020 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.048 | All H-atom parameters refined |
S = 1.08 | w = 1/[σ2(Fo2) + (0.015P)2 + 0.38P] where P = (Fo2 + 2Fc2)/3 |
4031 reflections | (Δ/σ)max = 0.002 |
257 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.50 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Sn1 | 0.189574 (12) | −0.040303 (11) | 0.833600 (11) | 0.02239 (5) | |
Cl1 | −0.00424 (5) | −0.17402 (5) | 0.97088 (4) | 0.02835 (10) | |
Cl2 | 0.26995 (5) | −0.21944 (5) | 0.72810 (4) | 0.03003 (10) | |
O1 | 0.37415 (16) | 0.05150 (15) | 0.68864 (14) | 0.0360 (3) | |
O2 | 0.36018 (16) | 0.22579 (16) | 0.77203 (14) | 0.0372 (3) | |
O3 | 0.50707 (18) | 0.40535 (15) | 0.74894 (14) | 0.0369 (3) | |
H3 | 0.446 (3) | 0.334 (3) | 0.761 (3) | 0.0517 (14)* | |
O4 | 0.70805 (18) | 0.47088 (16) | 0.63189 (16) | 0.0411 (3) | |
C1 | 0.0234 (2) | 0.1327 (2) | 0.7178 (2) | 0.0306 (4) | |
H1A | −0.074 (3) | 0.140 (3) | 0.763 (3) | 0.0517 (14)* | |
H1B | 0.022 (3) | 0.119 (3) | 0.641 (3) | 0.0517 (14)* | |
H1C | 0.052 (3) | 0.213 (3) | 0.703 (3) | 0.0517 (14)* | |
C2 | 0.3373 (2) | −0.0967 (2) | 0.9908 (2) | 0.0330 (4) | |
H2A | 0.441 (3) | −0.097 (3) | 0.957 (3) | 0.0517 (14)* | |
H2B | 0.337 (3) | −0.193 (3) | 1.040 (3) | 0.0517 (14)* | |
H2C | 0.316 (3) | −0.040 (3) | 1.028 (3) | 0.0517 (14)* | |
C3 | 0.4146 (2) | 0.1606 (2) | 0.69195 (18) | 0.0267 (4) | |
C4 | 0.5336 (2) | 0.2083 (2) | 0.59017 (18) | 0.0255 (4) | |
H4 | 0.557 (3) | 0.155 (3) | 0.530 (3) | 0.0517 (14)* | |
C5 | 0.6127 (2) | 0.3067 (2) | 0.57648 (18) | 0.0262 (4) | |
H5 | 0.683 (3) | 0.320 (3) | 0.514 (3) | 0.0517 (14)* | |
C6 | 0.6105 (2) | 0.40012 (19) | 0.65640 (18) | 0.0269 (4) | |
N1 | 0.78734 (17) | 0.64472 (16) | 0.74679 (15) | 0.0239 (3) | |
H1 | 0.751 (3) | 0.581 (3) | 0.726 (3) | 0.0517 (14)* | |
C7 | 0.9551 (2) | 0.5769 (2) | 0.77443 (19) | 0.0275 (4) | |
H7A | 0.958 (3) | 0.490 (3) | 0.847 (3) | 0.0517 (14)* | |
H7B | 0.996 (3) | 0.642 (3) | 0.804 (3) | 0.0517 (14)* | |
C8 | 1.0451 (3) | 0.5471 (2) | 0.6571 (2) | 0.0384 (5) | |
H8A | 1.143 (3) | 0.495 (3) | 0.684 (3) | 0.0517 (14)* | |
H8B | 1.053 (3) | 0.636 (3) | 0.584 (3) | 0.0517 (14)* | |
H8C | 1.001 (3) | 0.490 (3) | 0.619 (3) | 0.0517 (14)* | |
C9 | 0.7589 (2) | 0.7789 (2) | 0.6277 (2) | 0.0312 (4) | |
H9A | 0.645 (3) | 0.818 (3) | 0.623 (3) | 0.0517 (14)* | |
H9B | 0.793 (3) | 0.749 (3) | 0.552 (3) | 0.0517 (14)* | |
C10 | 0.8357 (3) | 0.8930 (2) | 0.6322 (2) | 0.0394 (5) | |
H10A | 0.809 (3) | 0.976 (3) | 0.552 (3) | 0.0517 (14)* | |
H10B | 0.949 (3) | 0.851 (3) | 0.635 (3) | 0.0517 (14)* | |
H10C | 0.794 (3) | 0.922 (3) | 0.708 (3) | 0.0517 (14)* | |
C11 | 0.6979 (2) | 0.6707 (2) | 0.8650 (2) | 0.0331 (4) | |
H11A | 0.592 (3) | 0.721 (3) | 0.837 (3) | 0.0517 (14)* | |
H11B | 0.745 (3) | 0.733 (3) | 0.889 (3) | 0.0517 (14)* | |
C12 | 0.6976 (3) | 0.5321 (3) | 0.9757 (2) | 0.0471 (6) | |
H12A | 0.635 (3) | 0.553 (3) | 1.044 (3) | 0.0517 (14)* | |
H12B | 0.802 (3) | 0.482 (3) | 1.011 (3) | 0.0517 (14)* | |
H12C | 0.666 (3) | 0.457 (3) | 0.947 (3) | 0.0517 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn1 | 0.02418 (8) | 0.02334 (7) | 0.02196 (8) | −0.00951 (5) | −0.00124 (5) | −0.00725 (5) |
Cl1 | 0.0305 (2) | 0.0292 (2) | 0.0293 (2) | −0.01435 (17) | 0.00651 (18) | −0.01137 (17) |
Cl2 | 0.0336 (2) | 0.0317 (2) | 0.0308 (2) | −0.01283 (18) | 0.00723 (18) | −0.01639 (18) |
O1 | 0.0373 (8) | 0.0425 (8) | 0.0353 (8) | −0.0257 (6) | 0.0070 (6) | −0.0121 (6) |
O2 | 0.0339 (7) | 0.0439 (8) | 0.0370 (8) | −0.0159 (6) | 0.0139 (6) | −0.0169 (6) |
O3 | 0.0465 (8) | 0.0363 (7) | 0.0357 (8) | −0.0146 (6) | 0.0078 (6) | −0.0205 (6) |
O4 | 0.0448 (8) | 0.0434 (8) | 0.0489 (9) | −0.0246 (7) | 0.0028 (7) | −0.0232 (7) |
C1 | 0.0360 (10) | 0.0266 (9) | 0.0273 (10) | −0.0072 (8) | −0.0033 (8) | −0.0059 (8) |
C2 | 0.0297 (10) | 0.0397 (11) | 0.0324 (11) | −0.0076 (8) | −0.0062 (8) | −0.0141 (9) |
C3 | 0.0219 (8) | 0.0321 (9) | 0.0258 (9) | −0.0108 (7) | −0.0001 (7) | −0.0058 (7) |
C4 | 0.0229 (8) | 0.0313 (9) | 0.0266 (9) | −0.0111 (7) | 0.0012 (7) | −0.0120 (7) |
C5 | 0.0244 (9) | 0.0335 (9) | 0.0251 (9) | −0.0126 (7) | 0.0043 (7) | −0.0122 (7) |
C6 | 0.0297 (9) | 0.0246 (8) | 0.0275 (9) | −0.0073 (7) | −0.0041 (7) | −0.0084 (7) |
N1 | 0.0240 (7) | 0.0263 (7) | 0.0250 (8) | −0.0096 (6) | −0.0003 (6) | −0.0104 (6) |
C7 | 0.0231 (9) | 0.0263 (9) | 0.0314 (10) | −0.0059 (7) | −0.0006 (7) | −0.0073 (8) |
C8 | 0.0300 (10) | 0.0385 (11) | 0.0473 (13) | −0.0078 (9) | 0.0105 (9) | −0.0184 (10) |
C9 | 0.0314 (10) | 0.0313 (10) | 0.0290 (10) | −0.0066 (8) | −0.0081 (8) | −0.0058 (8) |
C10 | 0.0486 (13) | 0.0240 (9) | 0.0415 (12) | −0.0082 (9) | −0.0088 (10) | −0.0037 (9) |
C11 | 0.0297 (10) | 0.0402 (11) | 0.0330 (11) | −0.0079 (8) | 0.0050 (8) | −0.0183 (9) |
C12 | 0.0489 (14) | 0.0567 (14) | 0.0322 (12) | −0.0159 (11) | 0.0156 (10) | −0.0128 (11) |
Geometric parameters (Å, º) top
Sn1—Cl1 | 2.5252 (4) | N1—C7 | 1.505 (2) |
Sn1—Cl2 | 2.3954 (4) | N1—C9 | 1.510 (2) |
Sn1—O1 | 2.3077 (13) | N1—C11 | 1.504 (2) |
Sn1—C1 | 2.109 (2) | N1—H1 | 0.89 (3) |
Sn1—C2 | 2.104 (2) | C7—C8 | 1.511 (3) |
O1—C3 | 1.267 (2) | C7—H7A | 0.96 (3) |
O2—C3 | 1.254 (2) | C7—H7B | 0.99 (3) |
O2—H3 | 1.47 (3) | C8—H8A | 0.92 (3) |
O3—C6 | 1.298 (2) | C8—H8B | 0.99 (3) |
O3—H3 | 0.98 (3) | C8—H8C | 1.00 (3) |
O4—C6 | 1.226 (2) | C9—C10 | 1.513 (3) |
C1—H1A | 0.96 (3) | C9—H9A | 1.00 (3) |
C1—H1B | 0.89 (3) | C9—H9B | 0.97 (3) |
C1—H1C | 0.88 (3) | C10—H10A | 0.98 (3) |
C2—H2A | 0.97 (3) | C10—H10B | 1.00 (3) |
C2—H2B | 0.94 (3) | C10—H10C | 0.97 (3) |
C2—H2C | 0.79 (3) | C11—C12 | 1.507 (3) |
C3—C4 | 1.498 (2) | C11—H11A | 0.99 (3) |
C4—C5 | 1.332 (3) | C11—H11B | 0.97 (3) |
C4—H4 | 0.96 (3) | C12—H12A | 0.93 (3) |
C5—C6 | 1.487 (3) | C12—H12B | 0.99 (3) |
C5—H5 | 0.87 (3) | C12—H12C | 1.03 (3) |
| | | |
C2—Sn1—C1 | 141.93 (9) | C11—N1—H1 | 108.0 (17) |
C2—Sn1—O1 | 89.96 (7) | C7—N1—H1 | 105.6 (17) |
C1—Sn1—O1 | 87.58 (7) | C9—N1—H1 | 105.2 (17) |
C2—Sn1—Cl2 | 107.85 (6) | N1—C7—C8 | 112.72 (17) |
C1—Sn1—Cl2 | 109.06 (6) | N1—C7—H7A | 105.5 (15) |
O1—Sn1—Cl2 | 79.82 (4) | C8—C7—H7A | 111.5 (16) |
C2—Sn1—Cl1 | 94.37 (6) | N1—C7—H7B | 107.5 (15) |
C1—Sn1—Cl1 | 94.78 (6) | C8—C7—H7B | 111.4 (15) |
O1—Sn1—Cl1 | 169.56 (4) | H7A—C7—H7B | 108 (2) |
Cl2—Sn1—Cl1 | 89.807 (15) | C7—C8—H8A | 108.1 (17) |
C3—O1—Sn1 | 120.95 (12) | C7—C8—H8B | 113.0 (15) |
C3—O2—H3 | 109.8 (10) | H8A—C8—H8B | 109 (2) |
C6—O3—H3 | 110.5 (15) | C7—C8—H8C | 113.9 (16) |
Sn1—C1—H1A | 110.4 (15) | H8A—C8—H8C | 107 (2) |
Sn1—C1—H1B | 107.3 (17) | H8B—C8—H8C | 106 (2) |
H1A—C1—H1B | 114 (2) | N1—C9—C10 | 113.87 (16) |
Sn1—C1—H1C | 109.2 (17) | N1—C9—H9A | 106.5 (15) |
H1A—C1—H1C | 108 (2) | C10—C9—H9A | 109.3 (15) |
H1B—C1—H1C | 108 (2) | N1—C9—H9B | 107.0 (15) |
Sn1—C2—H2A | 109.2 (16) | C10—C9—H9B | 111.4 (16) |
Sn1—C2—H2B | 105.4 (16) | H9A—C9—H9B | 108 (2) |
H2A—C2—H2B | 106 (2) | C9—C10—H10A | 107.9 (16) |
Sn1—C2—H2C | 112 (2) | C9—C10—H10B | 107.0 (15) |
H2A—C2—H2C | 106 (3) | H10A—C10—H10B | 110 (2) |
H2B—C2—H2C | 118 (3) | C9—C10—H10C | 108.1 (16) |
O2—C3—O1 | 123.87 (17) | H10A—C10—H10C | 109 (2) |
O2—C3—C4 | 121.66 (17) | H10B—C10—H10C | 114 (2) |
O1—C3—C4 | 114.47 (16) | N1—C11—C12 | 111.81 (17) |
C5—C4—C3 | 129.55 (18) | N1—C11—H11A | 107.4 (16) |
C5—C4—H4 | 117.8 (16) | C12—C11—H11A | 109.9 (15) |
C3—C4—H4 | 112.6 (16) | N1—C11—H11B | 106.0 (16) |
C4—C5—C6 | 130.91 (17) | C12—C11—H11B | 112.2 (15) |
C4—C5—H5 | 118.9 (18) | H11A—C11—H11B | 109 (2) |
C6—C5—H5 | 110.1 (18) | C11—C12—H12A | 108.6 (16) |
O4—C6—O3 | 121.84 (18) | C11—C12—H12B | 111.9 (15) |
O4—C6—C5 | 118.15 (17) | H12A—C12—H12B | 107 (2) |
O3—C6—C5 | 120.01 (16) | C11—C12—H12C | 112.9 (15) |
C11—N1—C7 | 112.35 (15) | H12A—C12—H12C | 112 (2) |
C11—N1—C9 | 111.33 (15) | H12B—C12—H12C | 104 (2) |
C7—N1—C9 | 113.72 (14) | | |
| | | |
C2—Sn1—O1—C3 | −65.53 (15) | C4—C5—C6—O4 | 171.7 (2) |
C1—Sn1—O1—C3 | 76.46 (15) | C4—C5—C6—O3 | −8.5 (3) |
Cl2—Sn1—O1—C3 | −173.68 (14) | C11—N1—C7—C8 | 178.60 (16) |
Cl1—Sn1—O1—C3 | 179.84 (15) | C9—N1—C7—C8 | −53.8 (2) |
Sn1—O1—C3—O2 | 0.3 (3) | C11—N1—C9—C10 | 73.1 (2) |
Sn1—O1—C3—C4 | −179.06 (11) | C7—N1—C9—C10 | −55.1 (2) |
O2—C3—C4—C5 | 9.2 (3) | C7—N1—C11—C12 | −63.5 (2) |
O1—C3—C4—C5 | −171.35 (19) | C9—N1—C11—C12 | 167.66 (18) |
C3—C4—C5—C6 | 0.4 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2 | 0.98 (3) | 1.47 (3) | 2.451 (2) | 177 (3) |
N1—H1···O4 | 0.89 (3) | 1.89 (3) | 2.748 (2) | 162 (3) |
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