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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803028976/ac6075sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803028976/ac6075Isup2.hkl
Contains datablock I

CCDC reference: 231840

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.020
  • wR factor = 0.052
  • Data-to-parameter ratio = 19.4

checkCIF/PLATON results

No syntax errors found



Alert level C CRYSC01_ALERT_1_C The word below has not been recognised as a standard identifier. yellowish CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour. PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 9 C15 -SN1 -N2 -C8 98.00 7.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 14 C15 -SN1 -N2 -N1 -79.00 7.00 1.555 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 3899 Count of symmetry unique reflns 2239 Completeness (_total/calc) 174.14% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1660 Fraction of Friedel pairs measured 0.741 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 4 ALERT type 4 Improvement, methodology, query or suggestion

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 m3
Mr = 442.89Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 8116 reflections
a = 7.1865 (11) Åθ = 1.8–27.5°
b = 14.609 (2) ŵ = 1.82 mm1
c = 16.197 (2) ÅT = 293 K
V = 1700.6 (4) Å3Block, yellowish
Z = 40.38 × 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 tube3821 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
Detector resolution: 83.66 pixels mm-1θmax = 27.5°, θmin = 1.8°
ω scansh = 99
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1818
Tmin = 0.539, Tmax = 0.751l = 2116
11352 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.020H-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 reflectionsΔρmax = 0.27 e Å3
201 parametersΔρmin = 0.44 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.006 (18)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.02605 (2)0.074241 (10)0.422728 (10)0.03667 (6)
O10.0341 (3)0.06463 (11)0.45308 (11)0.0450 (4)
Cl10.25054 (11)0.04543 (6)0.33675 (5)0.05925 (19)
Cl20.32790 (11)0.09955 (5)0.49103 (4)0.05353 (17)
N10.1927 (3)0.08643 (14)0.32974 (13)0.0392 (5)
N20.1799 (3)0.00724 (14)0.32554 (12)0.0367 (4)
N30.1158 (3)0.18198 (14)0.33186 (13)0.0401 (5)
C10.1819 (4)0.27547 (19)0.35376 (17)0.0464 (6)
H10.23310.25300.30510.056*
C20.1779 (5)0.3686 (2)0.3682 (2)0.0589 (8)
H20.22590.40880.32910.071*
C30.1029 (4)0.40178 (18)0.4401 (2)0.0598 (8)
H30.10150.46450.44990.072*
C40.0309 (5)0.34363 (19)0.4972 (2)0.0603 (8)
H40.02090.36710.54540.072*
C50.0333 (4)0.25000 (18)0.48464 (18)0.0483 (6)
H50.01520.21050.52420.058*
C60.1097 (3)0.21556 (16)0.41174 (15)0.0373 (5)
C70.1119 (3)0.11541 (17)0.39783 (15)0.0374 (5)
C80.2492 (3)0.05165 (17)0.26449 (15)0.0395 (5)
C90.3462 (5)0.0076 (2)0.19418 (17)0.0550 (7)
H9A0.47830.01370.20120.083*
H9B0.30930.03670.14360.083*
H9C0.31390.05610.19220.083*
C100.2208 (4)0.15157 (18)0.26899 (16)0.0404 (5)
C110.0812 (4)0.27200 (18)0.33910 (17)0.0473 (6)
H110.00600.29250.38210.057*
C120.1532 (5)0.3340 (2)0.28524 (19)0.0564 (8)
H120.12800.39600.29150.068*
C130.2634 (5)0.3041 (2)0.2216 (2)0.0620 (8)
H130.31540.34570.18470.074*
C140.2962 (5)0.2117 (2)0.21291 (18)0.0538 (7)
H140.36870.19020.16950.065*
C150.1279 (5)0.1390 (2)0.51657 (19)0.0586 (8)
H15A0.04550.15780.56000.088*
H15B0.21850.09710.53820.088*
H15C0.19000.19170.49430.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.04349 (9)0.03243 (8)0.03409 (8)0.00121 (6)0.00536 (7)0.00277 (6)
O10.0617 (11)0.0333 (8)0.0400 (8)0.0022 (9)0.0137 (8)0.0012 (7)
Cl10.0477 (4)0.0666 (4)0.0634 (4)0.0037 (3)0.0037 (3)0.0106 (4)
Cl20.0554 (4)0.0534 (4)0.0519 (4)0.0008 (3)0.0116 (3)0.0014 (3)
N10.0432 (11)0.0339 (10)0.0403 (10)0.0012 (9)0.0030 (9)0.0031 (9)
N20.0400 (11)0.0365 (10)0.0336 (10)0.0004 (9)0.0020 (9)0.0018 (8)
N30.0441 (12)0.0378 (10)0.0383 (11)0.0021 (9)0.0055 (9)0.0006 (9)
C10.0498 (16)0.0396 (13)0.0496 (14)0.0047 (12)0.0024 (12)0.0049 (12)
C20.0579 (19)0.0405 (14)0.078 (2)0.0085 (14)0.0056 (17)0.0163 (15)
C30.0501 (15)0.0348 (12)0.094 (2)0.0003 (11)0.0013 (16)0.0058 (14)
C40.0530 (16)0.0468 (14)0.081 (2)0.0008 (14)0.0106 (17)0.0187 (15)
C50.0448 (13)0.0438 (12)0.0565 (15)0.0004 (12)0.0079 (13)0.0019 (11)
C60.0369 (11)0.0320 (11)0.0430 (13)0.0010 (9)0.0041 (10)0.0012 (10)
C70.0364 (12)0.0378 (12)0.0382 (12)0.0013 (10)0.0004 (9)0.0045 (10)
C80.0365 (12)0.0469 (13)0.0351 (11)0.0017 (10)0.0008 (10)0.0001 (10)
C90.0618 (18)0.0581 (16)0.0451 (15)0.0018 (15)0.0158 (14)0.0026 (13)
C100.0377 (12)0.0455 (12)0.0379 (12)0.0038 (11)0.0009 (11)0.0027 (11)
C110.0559 (16)0.0386 (12)0.0475 (14)0.0013 (12)0.0096 (12)0.0012 (12)
C120.070 (2)0.0395 (13)0.0601 (18)0.0054 (13)0.0191 (16)0.0077 (13)
C130.072 (2)0.0542 (17)0.0596 (18)0.0107 (16)0.0039 (17)0.0203 (15)
C140.0569 (17)0.0573 (16)0.0473 (15)0.0041 (14)0.0049 (13)0.0124 (14)
C150.071 (2)0.0527 (16)0.0525 (16)0.0056 (15)0.0196 (16)0.0115 (14)
Geometric parameters (Å, º) top
Sn1—O12.0883 (16)C4—H40.9300
Sn1—C152.105 (3)C5—C61.396 (4)
Sn1—N22.158 (2)C5—H50.9300
Sn1—N32.249 (2)C6—C71.480 (3)
Sn1—Cl22.4630 (8)C8—C101.476 (3)
Sn1—Cl12.4632 (8)C8—C91.482 (3)
O1—C71.290 (3)C9—H9A0.9600
N1—C71.317 (3)C9—H9B0.9600
N1—N21.373 (3)C9—H9C0.9600
N2—C81.283 (3)C10—C141.375 (4)
N3—C101.343 (3)C11—C121.359 (4)
N3—C111.344 (3)C11—H110.9300
C1—C21.381 (4)C12—C131.372 (5)
C1—C61.384 (3)C12—H120.9300
C1—H10.9300C13—C141.377 (5)
C2—C31.373 (5)C13—H130.9300
C2—H20.9300C14—H140.9300
C3—C41.358 (5)C15—H15A0.9600
C3—H30.9300C15—H15B0.9600
C4—C51.383 (4)C15—H15C0.9600
O1—Sn1—C15106.34 (10)C6—C5—H5120.5
O1—Sn1—N273.55 (7)C1—C6—C5119.6 (2)
C15—Sn1—N2179.10 (13)C1—C6—C7121.2 (2)
O1—Sn1—N3145.68 (7)C5—C6—C7119.3 (2)
C15—Sn1—N3107.98 (10)O1—C7—N1126.0 (2)
N2—Sn1—N372.14 (8)O1—C7—C6117.3 (2)
O1—Sn1—Cl290.89 (6)N1—C7—C6116.7 (2)
C15—Sn1—Cl294.08 (11)N2—C8—C10114.1 (2)
N2—Sn1—Cl286.81 (6)N2—C8—C9123.7 (2)
N3—Sn1—Cl286.35 (6)C10—C8—C9122.2 (2)
O1—Sn1—Cl189.40 (6)C8—C9—H9A109.5
C15—Sn1—Cl193.49 (11)C8—C9—H9B109.5
N2—Sn1—Cl185.62 (6)H9A—C9—H9B109.5
N3—Sn1—Cl188.91 (6)C8—C9—H9C109.5
Cl2—Sn1—Cl1172.02 (3)H9A—C9—H9C109.5
C7—O1—Sn1114.05 (15)H9B—C9—H9C109.5
C7—N1—N2109.4 (2)N3—C10—C14120.7 (3)
C8—N2—N1121.1 (2)N3—C10—C8116.3 (2)
C8—N2—Sn1122.11 (17)C14—C10—C8123.0 (3)
N1—N2—Sn1116.76 (15)N3—C11—C12121.7 (3)
C10—N3—C11119.6 (2)N3—C11—H11119.2
C10—N3—Sn1115.19 (16)C12—C11—H11119.2
C11—N3—Sn1125.1 (2)C11—C12—C13119.4 (3)
C2—C1—C6120.0 (3)C11—C12—H12120.3
C2—C1—H1120.0C13—C12—H12120.3
C6—C1—H1120.0C12—C13—C14119.2 (3)
C3—C2—C1120.0 (3)C12—C13—H13120.4
C3—C2—H2120.0C14—C13—H13120.4
C1—C2—H2120.0C10—C14—C13119.4 (3)
C4—C3—C2120.4 (3)C10—C14—H14120.3
C4—C3—H3119.8C13—C14—H14120.3
C2—C3—H3119.8Sn1—C15—H15A109.5
C3—C4—C5120.9 (3)Sn1—C15—H15B109.5
C3—C4—H4119.5H15A—C15—H15B109.5
C5—C4—H4119.5Sn1—C15—H15C109.5
C4—C5—C6119.1 (3)H15A—C15—H15C109.5
C4—C5—H5120.5H15B—C15—H15C109.5
C15—Sn1—O1—C7174.8 (2)C2—C1—C6—C50.1 (4)
N2—Sn1—O1—C74.23 (17)C2—C1—C6—C7179.9 (3)
N3—Sn1—O1—C75.8 (3)C4—C5—C6—C10.2 (4)
Cl2—Sn1—O1—C790.64 (18)C4—C5—C6—C7179.7 (3)
Cl1—Sn1—O1—C781.38 (18)Sn1—O1—C7—N14.4 (3)
C7—N1—N2—C8179.9 (2)Sn1—O1—C7—C6175.30 (17)
C7—N1—N2—Sn13.2 (3)N2—N1—C7—O10.8 (4)
O1—Sn1—N2—C8179.0 (2)N2—N1—C7—C6179.0 (2)
C15—Sn1—N2—C898 (7)C1—C6—C7—O1176.8 (2)
N3—Sn1—N2—C80.03 (19)C5—C6—C7—O13.1 (4)
Cl2—Sn1—N2—C887.16 (19)C1—C6—C7—N12.9 (4)
Cl1—Sn1—N2—C890.30 (19)C5—C6—C7—N1177.2 (2)
O1—Sn1—N2—N14.13 (17)N1—N2—C8—C10179.1 (2)
C15—Sn1—N2—N179 (7)Sn1—N2—C8—C102.4 (3)
N3—Sn1—N2—N1176.80 (19)N1—N2—C8—C90.4 (4)
Cl2—Sn1—N2—N196.01 (17)Sn1—N2—C8—C9176.3 (2)
Cl1—Sn1—N2—N186.53 (17)C11—N3—C10—C141.3 (4)
O1—Sn1—N3—C101.2 (3)Sn1—N3—C10—C14175.0 (2)
C15—Sn1—N3—C10178.2 (2)C11—N3—C10—C8178.9 (2)
N2—Sn1—N3—C102.75 (17)Sn1—N3—C10—C84.9 (3)
Cl2—Sn1—N3—C1085.07 (18)N2—C8—C10—N34.9 (3)
Cl1—Sn1—N3—C1088.50 (18)C9—C8—C10—N3173.9 (2)
O1—Sn1—N3—C11177.17 (19)N2—C8—C10—C14175.0 (3)
C15—Sn1—N3—C112.2 (3)C9—C8—C10—C146.2 (4)
N2—Sn1—N3—C11178.8 (2)C10—N3—C11—C121.4 (4)
Cl2—Sn1—N3—C1190.9 (2)Sn1—N3—C11—C12174.4 (2)
Cl1—Sn1—N3—C1195.5 (2)N3—C11—C12—C130.3 (5)
C6—C1—C2—C30.2 (5)C11—C12—C13—C141.0 (5)
C1—C2—C3—C40.6 (5)N3—C10—C14—C130.0 (5)
C2—C3—C4—C50.8 (5)C8—C10—C14—C13179.8 (3)
C3—C4—C5—C60.6 (5)C12—C13—C14—C101.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Cl1i0.932.773.587 (3)147
C9—H9C···N10.962.432.815 (4)103
Symmetry code: (i) x, y1/2, z+1/2.
 

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