{4-Amino-N′-[(2-oxidonaphthalen-1-yl)methyl­idene]benzohydrazidato}di­methyl­tin(IV)

Cheng, M.; Zhao, Y.; Dong, T.; Cui, J.

doi:10.1107/S1600536814014652

metal-organic compounds

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Volume 70| Part 7| July 2014| Page m283

https://doi.org/10.1107/S1600536814014652

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{4-Amino-N′-[(2-oxidonaphthalen-1-yl)methylidene]benzohydrazidato}dimethyltin(IV)

Miao Cheng,^a Yuhong Zhao,^a Tiantian Dong ^a and Jichun Cui ^a ^*

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: jchcui@163.com

(Received 10 June 2014; accepted 21 June 2014; online 25 June 2014)

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)methylidene]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 molecules into zigzag chains along [010].

Keywords: crystal structure.

CCDC reference: 1009501

Related literature

For the biological activity of organotin compounds, see: Hong et al. (2013 ). For a related crystal structure, see: Cui et al. (2013 ).

Experimental

Crystal data

[Sn(CH₃)₂(C₁₈H₁₃N₃O₂)]
M_r = 452.07
Orthorhombic, P b c a
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 ) T_min = 0.641, T_max = 0.818
8234 measured reflections
3265 independent reflections
2382 reflections with I > 2σ(I)
R_int = 0.055

Refinement

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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1ⁱ	0.86	2.46	3.245 (7)	152
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ .

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).

Supporting information

CCDC reference: 1009501

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536814014652/cv5466sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814014652/cv5466Isup2.hkl

checkCIF report

Comment top

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 Sn^IV 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].

Related literature top

For the biological activity of organotin compounds, see: Hong et al. (2013). For a related crystal structure, see: Cui et al. (2013).

Experimental top

[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%).

Structure description top

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

For the biological activity of organotin compounds, see: Hong et al. (2013). For a related crystal structure, see: Cui et al. (2013).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

Fig. 1. The molecular strucure of (I) showing showing the atomic numbering and 40% probability displacement ellipsoids. H atoms omitted for clarity.

{4-Amino-N'-[(2-oxidonaphthalen-1-yl)methylidene]benzohydrazidato}dimethyltin(IV) top

Crystal data top

[Sn(CH₃)₂(C₁₈H₁₃N₃O₂)]	D_x = 1.619 Mg m⁻³
M_r = 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 mm⁻¹
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

Data collection top

Bruker SMART 1000 diffractometer	3265 independent reflections
Radiation source: fine-focus sealed tube	2382 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
phi and ω scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→4
T_min = 0.641, T_max = 0.818	k = −8→15
8234 measured reflections	l = −33→40

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.034P)² + 1.7722P] where P = (F_o² + 2F_c²)/3
3265 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −1.27 e Å⁻³

Crystal data top

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

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.14	Δρ_max = 0.49 e Å⁻³
3265 reflections	Δρ_min = −1.27 e Å⁻³
237 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1ⁱ	0.86	2.46	3.245 (7)	152

Symmetry code: (i) −x+3/2, y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1ⁱ	0.86	2.46	3.245 (7)	152

Symmetry code: (i) −x+3/2, y+1/2, z.

Acknowledgements

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

References

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

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{4-Amino-N′-[(2-oxidonaphthalen-1-yl)methyl­­idene]benzohydrazidato}di­methyl­tin(IV)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{4-Amino-N′-[(2-oxidonaphthalen-1-yl)methylidene]benzohydrazidato}dimethyltin(IV)