metal-organic compounds
The chelate Sn-O-C-N-N-C-C-N fragment, together with the substituent methyl C atom, in the title complex, [SnCl2(CH3)(C14H12N3O)], is planar, allowing the tridentate O,N,N-donor atoms and the methyl ligand C atom to occupy the equatorial positions in an octahedral environment. The geometry of the Sn atom is distorted octahedral, with a Cl-Sn-Cl axial bond angle of 172.02 (3)°.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803028976/ac6075sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803028976/ac6075Isup2.hkl |
CCDC reference: 231840
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
Dichloromethyl[1-(2-pyridyl)ethanone benzoylhydrazonato]tin(IV) top
Crystal data top
[SnCl2(CH3)(C14H12N3O)] | Dx = 1.730 Mg m−3 |
Mr = 442.89 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 8116 reflections |
a = 7.1865 (11) Å | θ = 1.8–27.5° |
b = 14.609 (2) Å | µ = 1.82 mm−1 |
c = 16.197 (2) Å | T = 293 K |
V = 1700.6 (4) Å3 | Block, yellowish |
Z = 4 | 0.38 × 0.17 × 0.16 mm |
F(000) = 872 |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3899 independent reflections |
Radiation source: fine-focus sealed tube | 3821 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
Detector resolution: 83.66 pixels mm-1 | θmax = 27.5°, θmin = 1.8° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −18→18 |
Tmin = 0.539, Tmax = 0.751 | l = −21→16 |
11352 measured reflections |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.020 | H-atom parameters constrained |
wR(F2) = 0.052 | w = 1/[σ2(Fo2) + (0.0301P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
3899 reflections | Δρmax = 0.27 e Å−3 |
201 parameters | Δρmin = −0.44 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.006 (18) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.02605 (2) | 0.074241 (10) | 0.422728 (10) | 0.03667 (6) | |
O1 | 0.0341 (3) | −0.06463 (11) | 0.45308 (11) | 0.0450 (4) | |
Cl1 | −0.25054 (11) | 0.04543 (6) | 0.33675 (5) | 0.05925 (19) | |
Cl2 | 0.32790 (11) | 0.09955 (5) | 0.49103 (4) | 0.05353 (17) | |
N1 | 0.1927 (3) | −0.08643 (14) | 0.32974 (13) | 0.0392 (5) | |
N2 | 0.1799 (3) | 0.00724 (14) | 0.32554 (12) | 0.0367 (4) | |
N3 | 0.1158 (3) | 0.18198 (14) | 0.33186 (13) | 0.0401 (5) | |
C1 | 0.1819 (4) | −0.27547 (19) | 0.35376 (17) | 0.0464 (6) | |
H1 | 0.2331 | −0.2530 | 0.3051 | 0.056* | |
C2 | 0.1779 (5) | −0.3686 (2) | 0.3682 (2) | 0.0589 (8) | |
H2 | 0.2259 | −0.4088 | 0.3291 | 0.071* | |
C3 | 0.1029 (4) | −0.40178 (18) | 0.4401 (2) | 0.0598 (8) | |
H3 | 0.1015 | −0.4645 | 0.4499 | 0.072* | |
C4 | 0.0309 (5) | −0.34363 (19) | 0.4972 (2) | 0.0603 (8) | |
H4 | −0.0209 | −0.3671 | 0.5454 | 0.072* | |
C5 | 0.0333 (4) | −0.25000 (18) | 0.48464 (18) | 0.0483 (6) | |
H5 | −0.0152 | −0.2105 | 0.5242 | 0.058* | |
C6 | 0.1097 (3) | −0.21556 (16) | 0.41174 (15) | 0.0373 (5) | |
C7 | 0.1119 (3) | −0.11541 (17) | 0.39783 (15) | 0.0374 (5) | |
C8 | 0.2492 (3) | 0.05165 (17) | 0.26449 (15) | 0.0395 (5) | |
C9 | 0.3462 (5) | 0.0076 (2) | 0.19418 (17) | 0.0550 (7) | |
H9A | 0.4783 | 0.0137 | 0.2012 | 0.083* | |
H9B | 0.3093 | 0.0367 | 0.1436 | 0.083* | |
H9C | 0.3139 | −0.0561 | 0.1922 | 0.083* | |
C10 | 0.2208 (4) | 0.15157 (18) | 0.26899 (16) | 0.0404 (5) | |
C11 | 0.0812 (4) | 0.27200 (18) | 0.33910 (17) | 0.0473 (6) | |
H11 | 0.0060 | 0.2925 | 0.3821 | 0.057* | |
C12 | 0.1532 (5) | 0.3340 (2) | 0.28524 (19) | 0.0564 (8) | |
H12 | 0.1280 | 0.3960 | 0.2915 | 0.068* | |
C13 | 0.2634 (5) | 0.3041 (2) | 0.2216 (2) | 0.0620 (8) | |
H13 | 0.3154 | 0.3457 | 0.1847 | 0.074* | |
C14 | 0.2962 (5) | 0.2117 (2) | 0.21291 (18) | 0.0538 (7) | |
H14 | 0.3687 | 0.1902 | 0.1695 | 0.065* | |
C15 | −0.1279 (5) | 0.1390 (2) | 0.51657 (19) | 0.0586 (8) | |
H15A | −0.0455 | 0.1578 | 0.5600 | 0.088* | |
H15B | −0.2185 | 0.0971 | 0.5382 | 0.088* | |
H15C | −0.1900 | 0.1917 | 0.4943 | 0.088* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.04349 (9) | 0.03243 (8) | 0.03409 (8) | 0.00121 (6) | 0.00536 (7) | −0.00277 (6) |
O1 | 0.0617 (11) | 0.0333 (8) | 0.0400 (8) | 0.0022 (9) | 0.0137 (8) | −0.0012 (7) |
Cl1 | 0.0477 (4) | 0.0666 (4) | 0.0634 (4) | −0.0037 (3) | −0.0037 (3) | −0.0106 (4) |
Cl2 | 0.0554 (4) | 0.0534 (4) | 0.0519 (4) | −0.0008 (3) | −0.0116 (3) | −0.0014 (3) |
N1 | 0.0432 (11) | 0.0339 (10) | 0.0403 (10) | 0.0012 (9) | 0.0030 (9) | −0.0031 (9) |
N2 | 0.0400 (11) | 0.0365 (10) | 0.0336 (10) | 0.0004 (9) | 0.0020 (9) | −0.0018 (8) |
N3 | 0.0441 (12) | 0.0378 (10) | 0.0383 (11) | −0.0021 (9) | −0.0055 (9) | 0.0006 (9) |
C1 | 0.0498 (16) | 0.0396 (13) | 0.0496 (14) | 0.0047 (12) | −0.0024 (12) | −0.0049 (12) |
C2 | 0.0579 (19) | 0.0405 (14) | 0.078 (2) | 0.0085 (14) | −0.0056 (17) | −0.0163 (15) |
C3 | 0.0501 (15) | 0.0348 (12) | 0.094 (2) | 0.0003 (11) | −0.0013 (16) | 0.0058 (14) |
C4 | 0.0530 (16) | 0.0468 (14) | 0.081 (2) | 0.0008 (14) | 0.0106 (17) | 0.0187 (15) |
C5 | 0.0448 (13) | 0.0438 (12) | 0.0565 (15) | −0.0004 (12) | 0.0079 (13) | 0.0019 (11) |
C6 | 0.0369 (11) | 0.0320 (11) | 0.0430 (13) | 0.0010 (9) | −0.0041 (10) | −0.0012 (10) |
C7 | 0.0364 (12) | 0.0378 (12) | 0.0382 (12) | 0.0013 (10) | −0.0004 (9) | −0.0045 (10) |
C8 | 0.0365 (12) | 0.0469 (13) | 0.0351 (11) | −0.0017 (10) | 0.0008 (10) | 0.0001 (10) |
C9 | 0.0618 (18) | 0.0581 (16) | 0.0451 (15) | 0.0018 (15) | 0.0158 (14) | −0.0026 (13) |
C10 | 0.0377 (12) | 0.0455 (12) | 0.0379 (12) | −0.0038 (11) | −0.0009 (11) | 0.0027 (11) |
C11 | 0.0559 (16) | 0.0386 (12) | 0.0475 (14) | 0.0013 (12) | −0.0096 (12) | −0.0012 (12) |
C12 | 0.070 (2) | 0.0395 (13) | 0.0601 (18) | −0.0054 (13) | −0.0191 (16) | 0.0077 (13) |
C13 | 0.072 (2) | 0.0542 (17) | 0.0596 (18) | −0.0107 (16) | −0.0039 (17) | 0.0203 (15) |
C14 | 0.0569 (17) | 0.0573 (16) | 0.0473 (15) | −0.0041 (14) | 0.0049 (13) | 0.0124 (14) |
C15 | 0.071 (2) | 0.0527 (16) | 0.0525 (16) | 0.0056 (15) | 0.0196 (16) | −0.0115 (14) |
Geometric parameters (Å, º) top
Sn1—O1 | 2.0883 (16) | C4—H4 | 0.9300 |
Sn1—C15 | 2.105 (3) | C5—C6 | 1.396 (4) |
Sn1—N2 | 2.158 (2) | C5—H5 | 0.9300 |
Sn1—N3 | 2.249 (2) | C6—C7 | 1.480 (3) |
Sn1—Cl2 | 2.4630 (8) | C8—C10 | 1.476 (3) |
Sn1—Cl1 | 2.4632 (8) | C8—C9 | 1.482 (3) |
O1—C7 | 1.290 (3) | C9—H9A | 0.9600 |
N1—C7 | 1.317 (3) | C9—H9B | 0.9600 |
N1—N2 | 1.373 (3) | C9—H9C | 0.9600 |
N2—C8 | 1.283 (3) | C10—C14 | 1.375 (4) |
N3—C10 | 1.343 (3) | C11—C12 | 1.359 (4) |
N3—C11 | 1.344 (3) | C11—H11 | 0.9300 |
C1—C2 | 1.381 (4) | C12—C13 | 1.372 (5) |
C1—C6 | 1.384 (3) | C12—H12 | 0.9300 |
C1—H1 | 0.9300 | C13—C14 | 1.377 (5) |
C2—C3 | 1.373 (5) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C14—H14 | 0.9300 |
C3—C4 | 1.358 (5) | C15—H15A | 0.9600 |
C3—H3 | 0.9300 | C15—H15B | 0.9600 |
C4—C5 | 1.383 (4) | C15—H15C | 0.9600 |
O1—Sn1—C15 | 106.34 (10) | C6—C5—H5 | 120.5 |
O1—Sn1—N2 | 73.55 (7) | C1—C6—C5 | 119.6 (2) |
C15—Sn1—N2 | 179.10 (13) | C1—C6—C7 | 121.2 (2) |
O1—Sn1—N3 | 145.68 (7) | C5—C6—C7 | 119.3 (2) |
C15—Sn1—N3 | 107.98 (10) | O1—C7—N1 | 126.0 (2) |
N2—Sn1—N3 | 72.14 (8) | O1—C7—C6 | 117.3 (2) |
O1—Sn1—Cl2 | 90.89 (6) | N1—C7—C6 | 116.7 (2) |
C15—Sn1—Cl2 | 94.08 (11) | N2—C8—C10 | 114.1 (2) |
N2—Sn1—Cl2 | 86.81 (6) | N2—C8—C9 | 123.7 (2) |
N3—Sn1—Cl2 | 86.35 (6) | C10—C8—C9 | 122.2 (2) |
O1—Sn1—Cl1 | 89.40 (6) | C8—C9—H9A | 109.5 |
C15—Sn1—Cl1 | 93.49 (11) | C8—C9—H9B | 109.5 |
N2—Sn1—Cl1 | 85.62 (6) | H9A—C9—H9B | 109.5 |
N3—Sn1—Cl1 | 88.91 (6) | C8—C9—H9C | 109.5 |
Cl2—Sn1—Cl1 | 172.02 (3) | H9A—C9—H9C | 109.5 |
C7—O1—Sn1 | 114.05 (15) | H9B—C9—H9C | 109.5 |
C7—N1—N2 | 109.4 (2) | N3—C10—C14 | 120.7 (3) |
C8—N2—N1 | 121.1 (2) | N3—C10—C8 | 116.3 (2) |
C8—N2—Sn1 | 122.11 (17) | C14—C10—C8 | 123.0 (3) |
N1—N2—Sn1 | 116.76 (15) | N3—C11—C12 | 121.7 (3) |
C10—N3—C11 | 119.6 (2) | N3—C11—H11 | 119.2 |
C10—N3—Sn1 | 115.19 (16) | C12—C11—H11 | 119.2 |
C11—N3—Sn1 | 125.1 (2) | C11—C12—C13 | 119.4 (3) |
C2—C1—C6 | 120.0 (3) | C11—C12—H12 | 120.3 |
C2—C1—H1 | 120.0 | C13—C12—H12 | 120.3 |
C6—C1—H1 | 120.0 | C12—C13—C14 | 119.2 (3) |
C3—C2—C1 | 120.0 (3) | C12—C13—H13 | 120.4 |
C3—C2—H2 | 120.0 | C14—C13—H13 | 120.4 |
C1—C2—H2 | 120.0 | C10—C14—C13 | 119.4 (3) |
C4—C3—C2 | 120.4 (3) | C10—C14—H14 | 120.3 |
C4—C3—H3 | 119.8 | C13—C14—H14 | 120.3 |
C2—C3—H3 | 119.8 | Sn1—C15—H15A | 109.5 |
C3—C4—C5 | 120.9 (3) | Sn1—C15—H15B | 109.5 |
C3—C4—H4 | 119.5 | H15A—C15—H15B | 109.5 |
C5—C4—H4 | 119.5 | Sn1—C15—H15C | 109.5 |
C4—C5—C6 | 119.1 (3) | H15A—C15—H15C | 109.5 |
C4—C5—H5 | 120.5 | H15B—C15—H15C | 109.5 |
C15—Sn1—O1—C7 | 174.8 (2) | C2—C1—C6—C5 | 0.1 (4) |
N2—Sn1—O1—C7 | −4.23 (17) | C2—C1—C6—C7 | −179.9 (3) |
N3—Sn1—O1—C7 | −5.8 (3) | C4—C5—C6—C1 | −0.2 (4) |
Cl2—Sn1—O1—C7 | −90.64 (18) | C4—C5—C6—C7 | 179.7 (3) |
Cl1—Sn1—O1—C7 | 81.38 (18) | Sn1—O1—C7—N1 | 4.4 (3) |
C7—N1—N2—C8 | 179.9 (2) | Sn1—O1—C7—C6 | −175.30 (17) |
C7—N1—N2—Sn1 | −3.2 (3) | N2—N1—C7—O1 | −0.8 (4) |
O1—Sn1—N2—C8 | −179.0 (2) | N2—N1—C7—C6 | 179.0 (2) |
C15—Sn1—N2—C8 | 98 (7) | C1—C6—C7—O1 | 176.8 (2) |
N3—Sn1—N2—C8 | 0.03 (19) | C5—C6—C7—O1 | −3.1 (4) |
Cl2—Sn1—N2—C8 | −87.16 (19) | C1—C6—C7—N1 | −2.9 (4) |
Cl1—Sn1—N2—C8 | 90.30 (19) | C5—C6—C7—N1 | 177.2 (2) |
O1—Sn1—N2—N1 | 4.13 (17) | N1—N2—C8—C10 | 179.1 (2) |
C15—Sn1—N2—N1 | −79 (7) | Sn1—N2—C8—C10 | 2.4 (3) |
N3—Sn1—N2—N1 | −176.80 (19) | N1—N2—C8—C9 | 0.4 (4) |
Cl2—Sn1—N2—N1 | 96.01 (17) | Sn1—N2—C8—C9 | −176.3 (2) |
Cl1—Sn1—N2—N1 | −86.53 (17) | C11—N3—C10—C14 | 1.3 (4) |
O1—Sn1—N3—C10 | −1.2 (3) | Sn1—N3—C10—C14 | −175.0 (2) |
C15—Sn1—N3—C10 | 178.2 (2) | C11—N3—C10—C8 | −178.9 (2) |
N2—Sn1—N3—C10 | −2.75 (17) | Sn1—N3—C10—C8 | 4.9 (3) |
Cl2—Sn1—N3—C10 | 85.07 (18) | N2—C8—C10—N3 | −4.9 (3) |
Cl1—Sn1—N3—C10 | −88.50 (18) | C9—C8—C10—N3 | 173.9 (2) |
O1—Sn1—N3—C11 | −177.17 (19) | N2—C8—C10—C14 | 175.0 (3) |
C15—Sn1—N3—C11 | 2.2 (3) | C9—C8—C10—C14 | −6.2 (4) |
N2—Sn1—N3—C11 | −178.8 (2) | C10—N3—C11—C12 | −1.4 (4) |
Cl2—Sn1—N3—C11 | −90.9 (2) | Sn1—N3—C11—C12 | 174.4 (2) |
Cl1—Sn1—N3—C11 | 95.5 (2) | N3—C11—C12—C13 | 0.3 (5) |
C6—C1—C2—C3 | −0.2 (5) | C11—C12—C13—C14 | 1.0 (5) |
C1—C2—C3—C4 | 0.6 (5) | N3—C10—C14—C13 | 0.0 (5) |
C2—C3—C4—C5 | −0.8 (5) | C8—C10—C14—C13 | −179.8 (3) |
C3—C4—C5—C6 | 0.6 (5) | C12—C13—C14—C10 | −1.2 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cl1i | 0.93 | 2.77 | 3.587 (3) | 147 |
C9—H9C···N1 | 0.96 | 2.43 | 2.815 (4) | 103 |
Symmetry code: (i) −x, y−1/2, −z+1/2. |