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

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].

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.052
• wR factor = 0.121
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No '_symmetry_space_group_name_Hall' Given .....     Please Do !
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....         O2 Check
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0093 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H8     ..  H17     ..       1.97 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3B    ...     Please Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      4.566 Check

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Why ?
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          45 %
PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) .....          2 Why ?

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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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 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

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

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 U_iso(H) = 1.2 U_eq(N), and C—H = 0.93 - 0.97 Å, with U_iso(H) = 1.2 or 1.5 U_eq(C)

Computing details

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

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)

Crystal data

[Sn(CH3)2(C18H13N3O2)]	Dx = 1.619 Mg m^−3
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 mm^−1
c = 34.291 (2) Å	T = 293 K
V = 3710.1 (5) Å^3	Block, orange
Z = 8	0.35 × 0.20 × 0.15 mm
F(000) = 1808

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H-atom parameters constrained
S = 1.14	w = 1/[σ^2(Fo^2) + (0.034P)^2 + 1.7722P] where P = (Fo^2 + 2Fc^2)/3
3265 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −1.27 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1^i	0.86	2.46	3.245 (7)	152

Symmetry code: (i) −x+3/2, y+1/2, z.