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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802008176/ww6021sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802008176/ww6021Isup2.hkl
Contains datablock I

CCDC reference: 189298

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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








Computing details top

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.

(I) top
Crystal data top
(C6H16N)[SnCl2(CH3)(C6H6O4)]F(000) = 440
Mr = 436.92Dx = 1.609 Mg m3
Triclinic, P1Melting point: 333 K
a = 8.9962 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.1856 (2) ÅCell parameters from 7194 reflections
c = 10.8439 (3) Åθ = 1.0–27.4°
α = 69.9082 (9)°µ = 1.72 mm1
β = 83.7866 (10)°T = 173 K
γ = 75.1111 (13)°Prism, colourless
V = 901.63 (4) Å30.25 × 0.20 × 0.15 mm
Z = 2
Data collection top
Nonius KappaCCD
diffractometer
4031 independent reflections
Radiation source: fine-focus sealed tube3828 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
ω and φ scansθmax = 27.4°, θmin = 3.5°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 1111
Tmin = 0.673, Tmax = 0.782k = 1313
7194 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.020Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.048All 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 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.50 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.189574 (12)0.040303 (11)0.833600 (11)0.02239 (5)
Cl10.00424 (5)0.17402 (5)0.97088 (4)0.02835 (10)
Cl20.26995 (5)0.21944 (5)0.72810 (4)0.03003 (10)
O10.37415 (16)0.05150 (15)0.68864 (14)0.0360 (3)
O20.36018 (16)0.22579 (16)0.77203 (14)0.0372 (3)
O30.50707 (18)0.40535 (15)0.74894 (14)0.0369 (3)
H30.446 (3)0.334 (3)0.761 (3)0.0517 (14)*
O40.70805 (18)0.47088 (16)0.63189 (16)0.0411 (3)
C10.0234 (2)0.1327 (2)0.7178 (2)0.0306 (4)
H1A0.074 (3)0.140 (3)0.763 (3)0.0517 (14)*
H1B0.022 (3)0.119 (3)0.641 (3)0.0517 (14)*
H1C0.052 (3)0.213 (3)0.703 (3)0.0517 (14)*
C20.3373 (2)0.0967 (2)0.9908 (2)0.0330 (4)
H2A0.441 (3)0.097 (3)0.957 (3)0.0517 (14)*
H2B0.337 (3)0.193 (3)1.040 (3)0.0517 (14)*
H2C0.316 (3)0.040 (3)1.028 (3)0.0517 (14)*
C30.4146 (2)0.1606 (2)0.69195 (18)0.0267 (4)
C40.5336 (2)0.2083 (2)0.59017 (18)0.0255 (4)
H40.557 (3)0.155 (3)0.530 (3)0.0517 (14)*
C50.6127 (2)0.3067 (2)0.57648 (18)0.0262 (4)
H50.683 (3)0.320 (3)0.514 (3)0.0517 (14)*
C60.6105 (2)0.40012 (19)0.65640 (18)0.0269 (4)
N10.78734 (17)0.64472 (16)0.74679 (15)0.0239 (3)
H10.751 (3)0.581 (3)0.726 (3)0.0517 (14)*
C70.9551 (2)0.5769 (2)0.77443 (19)0.0275 (4)
H7A0.958 (3)0.490 (3)0.847 (3)0.0517 (14)*
H7B0.996 (3)0.642 (3)0.804 (3)0.0517 (14)*
C81.0451 (3)0.5471 (2)0.6571 (2)0.0384 (5)
H8A1.143 (3)0.495 (3)0.684 (3)0.0517 (14)*
H8B1.053 (3)0.636 (3)0.584 (3)0.0517 (14)*
H8C1.001 (3)0.490 (3)0.619 (3)0.0517 (14)*
C90.7589 (2)0.7789 (2)0.6277 (2)0.0312 (4)
H9A0.645 (3)0.818 (3)0.623 (3)0.0517 (14)*
H9B0.793 (3)0.749 (3)0.552 (3)0.0517 (14)*
C100.8357 (3)0.8930 (2)0.6322 (2)0.0394 (5)
H10A0.809 (3)0.976 (3)0.552 (3)0.0517 (14)*
H10B0.949 (3)0.851 (3)0.635 (3)0.0517 (14)*
H10C0.794 (3)0.922 (3)0.708 (3)0.0517 (14)*
C110.6979 (2)0.6707 (2)0.8650 (2)0.0331 (4)
H11A0.592 (3)0.721 (3)0.837 (3)0.0517 (14)*
H11B0.745 (3)0.733 (3)0.889 (3)0.0517 (14)*
C120.6976 (3)0.5321 (3)0.9757 (2)0.0471 (6)
H12A0.635 (3)0.553 (3)1.044 (3)0.0517 (14)*
H12B0.802 (3)0.482 (3)1.011 (3)0.0517 (14)*
H12C0.666 (3)0.457 (3)0.947 (3)0.0517 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02418 (8)0.02334 (7)0.02196 (8)0.00951 (5)0.00124 (5)0.00725 (5)
Cl10.0305 (2)0.0292 (2)0.0293 (2)0.01435 (17)0.00651 (18)0.01137 (17)
Cl20.0336 (2)0.0317 (2)0.0308 (2)0.01283 (18)0.00723 (18)0.01639 (18)
O10.0373 (8)0.0425 (8)0.0353 (8)0.0257 (6)0.0070 (6)0.0121 (6)
O20.0339 (7)0.0439 (8)0.0370 (8)0.0159 (6)0.0139 (6)0.0169 (6)
O30.0465 (8)0.0363 (7)0.0357 (8)0.0146 (6)0.0078 (6)0.0205 (6)
O40.0448 (8)0.0434 (8)0.0489 (9)0.0246 (7)0.0028 (7)0.0232 (7)
C10.0360 (10)0.0266 (9)0.0273 (10)0.0072 (8)0.0033 (8)0.0059 (8)
C20.0297 (10)0.0397 (11)0.0324 (11)0.0076 (8)0.0062 (8)0.0141 (9)
C30.0219 (8)0.0321 (9)0.0258 (9)0.0108 (7)0.0001 (7)0.0058 (7)
C40.0229 (8)0.0313 (9)0.0266 (9)0.0111 (7)0.0012 (7)0.0120 (7)
C50.0244 (9)0.0335 (9)0.0251 (9)0.0126 (7)0.0043 (7)0.0122 (7)
C60.0297 (9)0.0246 (8)0.0275 (9)0.0073 (7)0.0041 (7)0.0084 (7)
N10.0240 (7)0.0263 (7)0.0250 (8)0.0096 (6)0.0003 (6)0.0104 (6)
C70.0231 (9)0.0263 (9)0.0314 (10)0.0059 (7)0.0006 (7)0.0073 (8)
C80.0300 (10)0.0385 (11)0.0473 (13)0.0078 (9)0.0105 (9)0.0184 (10)
C90.0314 (10)0.0313 (10)0.0290 (10)0.0066 (8)0.0081 (8)0.0058 (8)
C100.0486 (13)0.0240 (9)0.0415 (12)0.0082 (9)0.0088 (10)0.0037 (9)
C110.0297 (10)0.0402 (11)0.0330 (11)0.0079 (8)0.0050 (8)0.0183 (9)
C120.0489 (14)0.0567 (14)0.0322 (12)0.0159 (11)0.0156 (10)0.0128 (11)
Geometric parameters (Å, º) top
Sn1—Cl12.5252 (4)N1—C71.505 (2)
Sn1—Cl22.3954 (4)N1—C91.510 (2)
Sn1—O12.3077 (13)N1—C111.504 (2)
Sn1—C12.109 (2)N1—H10.89 (3)
Sn1—C22.104 (2)C7—C81.511 (3)
O1—C31.267 (2)C7—H7A0.96 (3)
O2—C31.254 (2)C7—H7B0.99 (3)
O2—H31.47 (3)C8—H8A0.92 (3)
O3—C61.298 (2)C8—H8B0.99 (3)
O3—H30.98 (3)C8—H8C1.00 (3)
O4—C61.226 (2)C9—C101.513 (3)
C1—H1A0.96 (3)C9—H9A1.00 (3)
C1—H1B0.89 (3)C9—H9B0.97 (3)
C1—H1C0.88 (3)C10—H10A0.98 (3)
C2—H2A0.97 (3)C10—H10B1.00 (3)
C2—H2B0.94 (3)C10—H10C0.97 (3)
C2—H2C0.79 (3)C11—C121.507 (3)
C3—C41.498 (2)C11—H11A0.99 (3)
C4—C51.332 (3)C11—H11B0.97 (3)
C4—H40.96 (3)C12—H12A0.93 (3)
C5—C61.487 (3)C12—H12B0.99 (3)
C5—H50.87 (3)C12—H12C1.03 (3)
C2—Sn1—C1141.93 (9)C11—N1—H1108.0 (17)
C2—Sn1—O189.96 (7)C7—N1—H1105.6 (17)
C1—Sn1—O187.58 (7)C9—N1—H1105.2 (17)
C2—Sn1—Cl2107.85 (6)N1—C7—C8112.72 (17)
C1—Sn1—Cl2109.06 (6)N1—C7—H7A105.5 (15)
O1—Sn1—Cl279.82 (4)C8—C7—H7A111.5 (16)
C2—Sn1—Cl194.37 (6)N1—C7—H7B107.5 (15)
C1—Sn1—Cl194.78 (6)C8—C7—H7B111.4 (15)
O1—Sn1—Cl1169.56 (4)H7A—C7—H7B108 (2)
Cl2—Sn1—Cl189.807 (15)C7—C8—H8A108.1 (17)
C3—O1—Sn1120.95 (12)C7—C8—H8B113.0 (15)
C3—O2—H3109.8 (10)H8A—C8—H8B109 (2)
C6—O3—H3110.5 (15)C7—C8—H8C113.9 (16)
Sn1—C1—H1A110.4 (15)H8A—C8—H8C107 (2)
Sn1—C1—H1B107.3 (17)H8B—C8—H8C106 (2)
H1A—C1—H1B114 (2)N1—C9—C10113.87 (16)
Sn1—C1—H1C109.2 (17)N1—C9—H9A106.5 (15)
H1A—C1—H1C108 (2)C10—C9—H9A109.3 (15)
H1B—C1—H1C108 (2)N1—C9—H9B107.0 (15)
Sn1—C2—H2A109.2 (16)C10—C9—H9B111.4 (16)
Sn1—C2—H2B105.4 (16)H9A—C9—H9B108 (2)
H2A—C2—H2B106 (2)C9—C10—H10A107.9 (16)
Sn1—C2—H2C112 (2)C9—C10—H10B107.0 (15)
H2A—C2—H2C106 (3)H10A—C10—H10B110 (2)
H2B—C2—H2C118 (3)C9—C10—H10C108.1 (16)
O2—C3—O1123.87 (17)H10A—C10—H10C109 (2)
O2—C3—C4121.66 (17)H10B—C10—H10C114 (2)
O1—C3—C4114.47 (16)N1—C11—C12111.81 (17)
C5—C4—C3129.55 (18)N1—C11—H11A107.4 (16)
C5—C4—H4117.8 (16)C12—C11—H11A109.9 (15)
C3—C4—H4112.6 (16)N1—C11—H11B106.0 (16)
C4—C5—C6130.91 (17)C12—C11—H11B112.2 (15)
C4—C5—H5118.9 (18)H11A—C11—H11B109 (2)
C6—C5—H5110.1 (18)C11—C12—H12A108.6 (16)
O4—C6—O3121.84 (18)C11—C12—H12B111.9 (15)
O4—C6—C5118.15 (17)H12A—C12—H12B107 (2)
O3—C6—C5120.01 (16)C11—C12—H12C112.9 (15)
C11—N1—C7112.35 (15)H12A—C12—H12C112 (2)
C11—N1—C9111.33 (15)H12B—C12—H12C104 (2)
C7—N1—C9113.72 (14)
C2—Sn1—O1—C365.53 (15)C4—C5—C6—O4171.7 (2)
C1—Sn1—O1—C376.46 (15)C4—C5—C6—O38.5 (3)
Cl2—Sn1—O1—C3173.68 (14)C11—N1—C7—C8178.60 (16)
Cl1—Sn1—O1—C3179.84 (15)C9—N1—C7—C853.8 (2)
Sn1—O1—C3—O20.3 (3)C11—N1—C9—C1073.1 (2)
Sn1—O1—C3—C4179.06 (11)C7—N1—C9—C1055.1 (2)
O2—C3—C4—C59.2 (3)C7—N1—C11—C1263.5 (2)
O1—C3—C4—C5171.35 (19)C9—N1—C11—C12167.66 (18)
C3—C4—C5—C60.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.98 (3)1.47 (3)2.451 (2)177 (3)
N1—H1···O40.89 (3)1.89 (3)2.748 (2)162 (3)
 

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