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{4-Amino-N'-[(2-oxidonaphthalen-1-yl)methyl-idene]benzohydrazidato}di-methyl-tin(IV).
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PMID:  25161538     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
In the title compound, [Sn(CH3)2(C18H13N3O2)], the Sn(IV) ion is coordinated by one N and two O atoms from the tridentate 4-amino-N'-[(2-oxidonaphthalen-1-yl)methyl-idene]benzohydrazidate(2-) ligand and two C atoms from methyl ligands in a distorted trigonal-bipyramidal geometry. The dihedral angle between the naphthalene ring system and the benzene ring is 19.2 (2)°. In the crystal, weak N-H⋯O hydrogen bonds link the mol-ecules into zigzag chains along [010].
Authors:
Miao Cheng; Yuhong Zhao; Tiantian Dong; Jichun Cui
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Publication Detail:
Type:  Journal Article     Date:  2014-06-25
Journal Detail:
Title:  Acta crystallographica. Section E, Structure reports online     Volume:  70     ISSN:  1600-5368     ISO Abbreviation:  Acta Crystallogr Sect E Struct Rep Online     Publication Date:  2014 Jul 
Date Detail:
Created Date:  2014-08-27     Completed Date:  2014-08-27     Revised Date:  2014-08-29    
Medline Journal Info:
Nlm Unique ID:  101089178     Medline TA:  Acta Crystallogr Sect E Struct Rep Online     Country:  United States    
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Languages:  eng     Pagination:  m283     Citation Subset:  -    
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Journal Information
Journal ID (nlm-ta): Acta Crystallogr Sect E Struct Rep Online
Journal ID (iso-abbrev): Acta Crystallogr Sect E Struct Rep Online
Journal ID (publisher-id): Acta Cryst. E
ISSN: 1600-5368
Publisher: International Union of Crystallography
Article Information
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A full version of this article is available from Crystallography Journals Online.© Cheng et al. 2014
open-access:
Received Day: 10 Month: 6 Year: 2014
Accepted Day: 21 Month: 6 Year: 2014
collection publication date: Day: 01 Month: 7 Year: 2014
Electronic publication date: Day: 25 Month: 6 Year: 2014
pmc-release publication date: Day: 25 Month: 6 Year: 2014
Volume: 70 Issue: Pt 7
First Page: m283 Last Page: m283
PubMed Id: 25161538
ID: 4120628
Publisher Id: cv5466
DOI: 10.1107/S1600536814014652
Coden: ACSEBH
Publisher Item Identifier: S1600536814014652

{4-Amino-N′-[(2-oxidonaphthalen-1-yl)methyl­idene]benzohydrazidato}di­methyl­tin(IV) Alternate Title:[Sn(CH3)2(C18H13N3O2)]
Miao Chenga
Yuhong Zhaoa
Tiantian Donga
Jichun Cuia*
aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People’s Republic of China
Correspondence: Correspondence e-mail: jchcui@163.com

Related literature  

For the biological activity of organotin compounds, see: Hong et al. (2013). For a related crystal structure, see: Cui et al. (2013).[Chemical Structure ID: scheme1]


Experimental  
Crystal data  

  • [Sn(CH3)2(C18H13N3O2)]
  • Mr = 452.07
  • Orthorhombic,
  • a = 8.3545 (7) Å
  • b = 12.9503 (11) Å
  • c = 34.291 (2) Å
  • V = 3710.1 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.40 mm−1
  • T = 293 K
  • 0.35 × 0.20 × 0.15 mm

Data collection  

  • Bruker SMART 1000 diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2007) Tmin = 0.641, Tmax = 0.818
  • 8234 measured reflections
  • 3265 independent reflections
  • 2382 reflections with I > 2σ(I)
  • Rint = 0.055

Refinement  

  • R[F2 > 2σ(F2)] = 0.052
  • wR(F2) = 0.121
  • S = 1.14
  • 3265 reflections
  • 237 parameters
  • H-atom parameters constrained
  • Δρmax = 0.49 e Å−3
  • Δρmin = −1.27 e Å−3

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).


Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814014652/cv5466sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014652/cv5466Isup2.hkl

CCDC reference: 1009501

Additional supporting information: crystallographic information; 3D view; checkCIF report


Notes

fnu1Supporting information for this paper is available from the IUCr electronic archives (Reference: CV5466).

We acknowledge the Students Science and Technology Innovation Fund of Liaocheng University (SF2012053).

supplementary crystallographic information
S1. Comment

The chemistry of organotin(IV) derivatives is a subject of study with growing interest due to their significant antimicrobial properties as well as antitumor activities (Hong et al., 2013). As a part of our ongoing investigations in this field (Cui et al., 2013) we have synthesized the title compound, (I), and present its crystal structure here.

In (I) (Fig. 1), the SnIV ion has distorted trigonal-bipyramidal coordination geometry, with atoms O1 and O2 in axial positions [O1—Sn1—O3 = 154.81 (18) °] and the atoms C19, C20 and N2 in equatorial positions. This coordination geometry is similar to that observed in the related compound {4-chloro-N'-[(2-oxidonaphthalen-1-ylκO) methylidene]benzohydrazidato-κ2N',O}dimethyltin(IV) (Cui et al., 2013).

In the crystal, weak intermolecular N—H···O hydrogen bonds (Table 1) link molecules into zigzag chains in [010].

S2. Experimental

[4-Azyl-N'-(2-hydroxy-1-naphthaldehyde)benzohydrazide (1 mmol) and sodium ethoxide (2 mmol) were added to the solution of dry methanol(30 ml) and stirred for 10 min. Dimethyltin(IV) dichloride (1 mmol) was then added to the reactor and the reaction mixture was stirred for 4 h. The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/ethanol(1:1) to yield orange blocks of the title compound (yield 86%).

S3. Refinement

The H atoms were fixed geometrically and treated as riding atoms: N—H = 0.86 Å, with Uiso(H) = 1.2 Ueq(N), and C—H = 0.93 - 0.97 Å, with Uiso(H) = 1.2 or 1.5 Ueq(C)

Figures
Crystal data
Data collection
Refinement
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
Atomic displacement parameters (Å2)
Geometric parameters (Å, º)
Hydrogen-bond geometry (Å, º)

Symmetry code: (i) −x+3/2, y+1/2, z.


References
Bruker (2007). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
Cui, J., Qiao, Y. & Wang, F. (2013). Acta Cryst. E69, m688.
Hong, M., Yin, H., Zhang, X., Li, C., Yue, C. & Cheng, S. (2013). J. Organomet. Chem.724, 23–31.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Figures

[Figure ID: Fap1]
Fig. 1. 

The molecular strucure of (I) showing showing the atomic numbering and 40% probability displacement ellipsoids. H atoms omitted for clarity.



Tables
[TableWrap ID: d1e143]
[Sn(CH3)2(C18H13N3O2)] Dx = 1.619 Mg m3
Mr = 452.07 Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca Cell parameters from 1667 reflections
a = 8.3545 (7) Å θ = 2.7–28.4°
b = 12.9503 (11) Å µ = 1.40 mm1
c = 34.291 (2) Å T = 293 K
V = 3710.1 (5) Å3 Block, orange
Z = 8 0.35 × 0.20 × 0.15 mm
F(000) = 1808

[TableWrap ID: d1e274]
Bruker SMART 1000 diffractometer 3265 independent reflections
Radiation source: fine-focus sealed tube 2382 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.055
phi and ω scans θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007) h = −9→4
Tmin = 0.641, Tmax = 0.818 k = −8→15
8234 measured reflections l = −33→40

[TableWrap ID: d1e389]
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)] = 0.052 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121 H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.034P)2 + 1.7722P] where P = (Fo2 + 2Fc2)/3
3265 reflections (Δ/σ)max < 0.001
237 parameters Δρmax = 0.49 e Å3
0 restraints Δρmin = −1.27 e Å3

[TableWrap ID: d1e549]
x y z Uiso*/Ueq
Sn1 0.22653 (5) 0.82846 (3) 0.350360 (13) 0.03635 (18)
C1 0.6096 (7) 1.0398 (4) 0.31885 (17) 0.0282 (13)
C2 0.6565 (7) 1.1338 (4) 0.33421 (18) 0.0333 (14)
H2 0.6144 1.1553 0.3580 0.040*
C3 0.7651 (7) 1.1966 (5) 0.3149 (2) 0.0357 (16)
H3 0.7940 1.2599 0.3256 0.043*
C4 0.8311 (7) 1.1654 (5) 0.27934 (19) 0.0346 (14)
C5 0.7822 (7) 1.0706 (5) 0.26347 (19) 0.0361 (15)
H5 0.8241 1.0488 0.2397 0.043*
C6 0.6718 (7) 1.0092 (4) 0.28297 (18) 0.0326 (14)
H6 0.6391 0.9471 0.2720 0.039*
C7 0.4895 (7) 0.9742 (5) 0.33911 (19) 0.0337 (15)
C8 0.3081 (8) 0.9472 (4) 0.4283 (2) 0.0358 (15)
H8 0.3624 1.0011 0.4404 0.043*
C9 0.1988 (7) 0.8916 (5) 0.45182 (18) 0.0331 (15)
C10 0.1039 (7) 0.8101 (4) 0.43669 (19) 0.0365 (15)
C18 0.1849 (7) 0.9175 (5) 0.4931 (2) 0.0366 (15)
C11 0.0086 (9) 0.7509 (5) 0.4619 (2) 0.052 (2)
H11 −0.0513 0.6962 0.4521 0.062*
C12 0.0036 (9) 0.7732 (6) 0.5005 (2) 0.057 (2)
H12 −0.0591 0.7321 0.5167 0.069*
C13 0.0892 (8) 0.8557 (5) 0.5173 (2) 0.0456 (18)
C14 0.0800 (10) 0.8798 (7) 0.5574 (2) 0.065 (2)
H14 0.0174 0.8382 0.5734 0.078*
C15 0.1576 (10) 0.9600 (7) 0.5734 (2) 0.067 (2)
H15 0.1495 0.9737 0.5999 0.081*
C16 0.2504 (9) 1.0222 (7) 0.5491 (2) 0.058 (2)
H16 0.3037 1.0788 0.5596 0.070*
C17 0.2644 (8) 1.0012 (6) 0.5102 (2) 0.0485 (19)
H17 0.3282 1.0435 0.4948 0.058*
C19 0.0383 (9) 0.9080 (5) 0.3224 (2) 0.057 (2)
H19A −0.0545 0.9080 0.3389 0.085*
H19B 0.0132 0.8742 0.2982 0.085*
H19C 0.0705 0.9778 0.3173 0.085*
C20 0.3138 (9) 0.6763 (5) 0.3414 (2) 0.056 (2)
H20A 0.2512 0.6286 0.3564 0.084*
H20B 0.4237 0.6726 0.3495 0.084*
H20C 0.3059 0.6590 0.3142 0.084*
N1 0.4605 (6) 0.9964 (3) 0.37632 (14) 0.0331 (12)
N2 0.3417 (6) 0.9318 (3) 0.39137 (15) 0.0323 (12)
N3 0.9344 (7) 1.2295 (4) 0.25953 (17) 0.0493 (15)
H3A 0.9585 1.2890 0.2690 0.059*
H3B 0.9749 1.2101 0.2377 0.059*
O1 0.4219 (5) 0.9000 (3) 0.31939 (12) 0.0393 (11)
O2 0.0996 (6) 0.7846 (4) 0.39985 (14) 0.0609 (15)

[TableWrap ID: d1e1135]
U11 U22 U33 U12 U13 U23
Sn1 0.0369 (3) 0.0357 (3) 0.0364 (3) −0.00536 (19) 0.0007 (2) −0.0002 (2)
C1 0.029 (3) 0.032 (3) 0.023 (3) 0.000 (3) 0.002 (3) 0.004 (3)
C2 0.032 (3) 0.040 (3) 0.027 (3) 0.003 (3) 0.004 (3) −0.005 (3)
C3 0.041 (3) 0.030 (3) 0.036 (4) −0.002 (3) 0.007 (3) 0.003 (3)
C4 0.024 (3) 0.039 (3) 0.041 (4) 0.004 (3) −0.002 (3) 0.002 (3)
C5 0.034 (3) 0.048 (4) 0.026 (3) 0.003 (3) 0.004 (3) 0.004 (3)
C6 0.032 (3) 0.033 (3) 0.033 (4) −0.002 (3) −0.003 (3) 0.003 (3)
C7 0.026 (3) 0.035 (3) 0.040 (4) 0.007 (3) −0.002 (3) 0.006 (3)
C8 0.043 (3) 0.027 (3) 0.037 (4) −0.004 (3) −0.003 (3) 0.009 (3)
C9 0.036 (3) 0.039 (3) 0.024 (3) −0.001 (3) 0.001 (3) 0.007 (3)
C10 0.032 (3) 0.039 (3) 0.039 (4) −0.003 (3) 0.005 (3) 0.007 (3)
C18 0.033 (3) 0.038 (4) 0.038 (4) 0.009 (3) −0.001 (3) 0.006 (3)
C11 0.054 (4) 0.043 (4) 0.057 (6) −0.014 (4) 0.008 (4) 0.005 (4)
C12 0.048 (4) 0.064 (5) 0.060 (6) −0.006 (4) 0.018 (4) 0.026 (4)
C13 0.039 (4) 0.062 (5) 0.036 (4) 0.009 (3) 0.005 (4) 0.013 (4)
C14 0.053 (5) 0.086 (6) 0.055 (6) 0.010 (5) 0.017 (5) 0.018 (5)
C15 0.073 (6) 0.097 (7) 0.032 (4) 0.015 (5) 0.006 (5) −0.005 (5)
C16 0.059 (5) 0.071 (5) 0.044 (5) 0.014 (4) −0.010 (4) −0.013 (4)
C17 0.052 (4) 0.054 (4) 0.039 (4) 0.005 (3) 0.001 (4) 0.000 (4)
C19 0.053 (4) 0.052 (4) 0.066 (5) 0.001 (4) −0.010 (4) 0.007 (4)
C20 0.055 (4) 0.038 (4) 0.075 (6) 0.002 (4) 0.005 (4) −0.004 (4)
N1 0.035 (3) 0.041 (3) 0.023 (3) −0.013 (2) 0.000 (3) 0.005 (2)
N2 0.030 (3) 0.037 (3) 0.030 (3) −0.007 (2) 0.002 (3) 0.004 (2)
N3 0.050 (3) 0.043 (3) 0.054 (4) −0.004 (3) 0.020 (3) 0.006 (3)
O1 0.048 (2) 0.037 (2) 0.033 (3) −0.014 (2) 0.006 (2) −0.005 (2)
O2 0.075 (4) 0.065 (3) 0.043 (3) −0.039 (3) 0.012 (3) −0.001 (3)

[TableWrap ID: d1e1626]
Sn1—O2 2.080 (5) C10—C11 1.403 (9)
Sn1—C19 2.110 (7) C18—C17 1.401 (9)
Sn1—C20 2.123 (6) C18—C13 1.402 (9)
Sn1—O1 2.157 (4) C11—C12 1.356 (10)
Sn1—N2 2.167 (5) C11—H11 0.9300
C1—C2 1.383 (8) C12—C13 1.409 (10)
C1—C6 1.393 (8) C12—H12 0.9300
C1—C7 1.487 (8) C13—C14 1.412 (10)
C2—C3 1.388 (8) C14—C15 1.342 (11)
C2—H2 0.9300 C14—H14 0.9300
C3—C4 1.397 (9) C15—C16 1.394 (11)
C3—H3 0.9300 C15—H15 0.9300
C4—N3 1.377 (8) C16—C17 1.366 (10)
C4—C5 1.403 (8) C16—H16 0.9300
C5—C6 1.389 (8) C17—H17 0.9300
C5—H5 0.9300 C19—H19A 0.9600
C6—H6 0.9300 C19—H19B 0.9600
C7—O1 1.304 (7) C19—H19C 0.9600
C7—N1 1.330 (8) C20—H20A 0.9600
C8—N2 1.311 (8) C20—H20B 0.9600
C8—C9 1.416 (8) C20—H20C 0.9600
C8—H8 0.9300 N1—N2 1.397 (6)
C9—C10 1.418 (8) N3—H3A 0.8600
C9—C18 1.458 (9) N3—H3B 0.8600
C10—O2 1.306 (7)
O2—Sn1—C19 97.1 (3) C12—C11—C10 120.2 (7)
O2—Sn1—C20 92.3 (3) C12—C11—H11 119.9
C19—Sn1—C20 130.0 (3) C10—C11—H11 119.9
O2—Sn1—O1 154.81 (18) C11—C12—C13 122.9 (7)
C19—Sn1—O1 97.5 (2) C11—C12—H12 118.5
C20—Sn1—O1 93.9 (2) C13—C12—H12 118.5
O2—Sn1—N2 82.28 (18) C18—C13—C12 118.8 (7)
C19—Sn1—N2 108.9 (2) C18—C13—C14 118.8 (7)
C20—Sn1—N2 121.0 (2) C12—C13—C14 122.5 (7)
O1—Sn1—N2 73.63 (17) C15—C14—C13 122.9 (8)
C2—C1—C6 118.8 (5) C15—C14—H14 118.5
C2—C1—C7 121.0 (5) C13—C14—H14 118.5
C6—C1—C7 120.1 (5) C14—C15—C16 118.1 (7)
C1—C2—C3 121.3 (6) C14—C15—H15 120.9
C1—C2—H2 119.4 C16—C15—H15 120.9
C3—C2—H2 119.4 C17—C16—C15 121.0 (8)
C2—C3—C4 120.3 (6) C17—C16—H16 119.5
C2—C3—H3 119.8 C15—C16—H16 119.5
C4—C3—H3 119.8 C16—C17—C18 121.6 (8)
N3—C4—C3 120.2 (6) C16—C17—H17 119.2
N3—C4—C5 121.2 (6) C18—C17—H17 119.2
C3—C4—C5 118.5 (6) Sn1—C19—H19A 109.5
C6—C5—C4 120.4 (6) Sn1—C19—H19B 109.5
C6—C5—H5 119.8 H19A—C19—H19B 109.5
C4—C5—H5 119.8 Sn1—C19—H19C 109.5
C5—C6—C1 120.7 (6) H19A—C19—H19C 109.5
C5—C6—H6 119.7 H19B—C19—H19C 109.5
C1—C6—H6 119.7 Sn1—C20—H20A 109.5
O1—C7—N1 125.3 (5) Sn1—C20—H20B 109.5
O1—C7—C1 118.1 (5) H20A—C20—H20B 109.5
N1—C7—C1 116.6 (5) Sn1—C20—H20C 109.5
N2—C8—C9 127.7 (6) H20A—C20—H20C 109.5
N2—C8—H8 116.2 H20B—C20—H20C 109.5
C9—C8—H8 116.2 C7—N1—N2 110.8 (5)
C8—C9—C10 122.0 (6) C8—N2—N1 114.7 (5)
C8—C9—C18 119.2 (6) C8—N2—Sn1 128.7 (4)
C10—C9—C18 118.8 (6) N1—N2—Sn1 116.5 (4)
O2—C10—C11 116.2 (6) C4—N3—H3A 120.0
O2—C10—C9 123.9 (6) C4—N3—H3B 120.0
C11—C10—C9 119.9 (6) H3A—N3—H3B 120.0
C17—C18—C13 117.6 (7) C7—O1—Sn1 112.9 (4)
C17—C18—C9 123.2 (6) C10—O2—Sn1 134.9 (4)
C13—C18—C9 119.2 (6)

[TableWrap ID: d1e2261]
D—H···A D—H H···A D···A D—H···A
N3—H3A···O1i 0.86 2.46 3.245 (7) 152


Article Categories:
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Keywords: crystal structure.

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