Dieth­yl[N-(3-meth­oxy-2-oxidobenzyl­idene)-N′-(oxidomethyl­ene)hydrazine-κ3O,N,O′]tin(IV)

Shuja, S.; Tahir, M.N.; Ali, S.; Khalid, N.

doi:10.1107/S1600536808018953

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Pages m963-m964

doi:10.1107/S1600536808018953

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Diethyl[N-(3-methoxy-2-oxidobenzylidene)-N′-(oxidomethylene)hydrazine-κ³O,N,O′]tin(IV)

Shaukat Shuja,^a M. Nawaz Tahir,^b ^* Saqib Ali ^a and Nasir Khalid ^c

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, ^bUniversity of Sargodha, Department of Physics, Sagrodha, Pakistan, and ^cChemistry Division, Pakistan Institute of Nuclear Science and Technology, PO Nilore, Islamabad, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 20 June 2008; accepted 23 June 2008; online 28 June 2008)

In the molecule of the title compound, [Sn(C₂H₅)₂(C₉H₈N₂O₃)], the Sn atom is five-coordinated in a distorted trigonal-bipyramidal configuration by two O and one N atoms of the tridentate Schiff base ligand in the equatorial plane, and by two C atoms of ethyl groups in the axial positions. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For related literature, see: Chen et al. (2006 ); Shuja et al. (2007a ,b ,c ); Shuja et al. (2008 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

[Sn(C₂H₅)₂(C₉H₈N₂O₃)]
M_r = 368.98
Triclinic, $[P \overline 1]$
a = 8.2485 (3) Å
b = 9.8609 (4) Å
c = 10.4501 (4) Å
α = 63.521 (2)°
β = 68.967 (1)°
γ = 77.803 (2)°
V = 708.79 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.81 mm⁻¹
T = 296 (2) K
0.30 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.650, T_max = 0.720
14275 measured reflections
3603 independent reflections
3458 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.016
wR(F²) = 0.063
S = 1.02
3603 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—C11	2.1216 (19)
Sn1—C9	2.1217 (18)
Sn1—O1	2.1888 (13)
Sn1—O2	2.2162 (14)
Sn1—N1	2.2271 (15)

C11—Sn1—C9	153.45 (9)
C11—Sn1—O1	97.19 (7)
C9—Sn1—O1	93.40 (7)
C11—Sn1—O2	92.71 (8)
C9—Sn1—O2	88.78 (7)
O1—Sn1—O2	152.79 (5)
C11—Sn1—N1	99.42 (7)
C9—Sn1—N1	106.13 (7)
O1—Sn1—N1	82.07 (5)
O2—Sn1—N1	71.30 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O2ⁱ	0.96	2.34	3.068 (4)	132
Symmetry code: (i) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: APEX2; 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: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018953/hk2477sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018953/hk2477Isup2.hkl

checkCIF report

Comment top

In continuation of our efforts to synthesize various Schiff base ligands of substituted salicylaldehydes with hydrazides, aminoacids and their organotin derivatives (Shuja et al., 2007a,b,c; Shuja et al., 2008), we report herein the crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), the Sn atom is five-coordinated in distorted trigonal bipyramidal configuration (Table 1) by two O and one N atoms of the tridentate Schiff base ligand in the equatorial plane, and two C atoms of diethyl groups in the axial positions. The bond lengths and angles are within normal ranges, which are comparable with the corresponding values in (3-methoxy-2-oxidobenzaldehyde benzoylhydrazonato)dimethyltin(IV), (II) (Chen et al., 2006) and (2,2'-bipyridine-κ²N,N'){[(3-methoxy-2-oxidobenzylidene -κO²)hydrazono]methanolato-κ²N²,O}dimethyltin(IV), (III) (Shuja et al., 2008). The Sn1-C9 [2.1217 (18) Å] and Sn1-C11 [2.1219 (19) Å] bonds in (I) are reported as 2.099 (4) and 2.102 (4) Å in (II) and 2.097 (3) and 2.098 (3) Å in (III). On the other hand, the Sn1-O1 [2.1888 (13) Å] and Sn1-O2 [2.2162 (14) Å] bonds in (I) are reported as 2.131 (3) and 2.178 (3) Å in (II) and 2.1572 (14) and 2.2658 (15) Å in (III), while the Sn1-N1 [2.2271 (15) Å] bond in (I) is reported as 2.188 (3) Å in (II) and 2.2980 (18) Å in (III).

Rings A (Sn1/O2/N1/N2/C8) and C (C1-C6) are, of course, planar, and the dihedral angle between them is A/C = 7.96 (3)°. Ring B (Sn1/O1/N1/C1/C6/C7) adopts flattened-boat [ϕ = -57.24 (2)° and θ = 107.39 (3)°] conformation, having total puckering amplitude, Q_T, of 0.453 (3) Å (Cremer & Pople, 1975).

In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 2) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For related literature, see: Chen et al. (2006); Shuja et al. (2007a,b,c); Shuja et al. (2008). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

For the preparation of the title compound, N-(3-methoxy-2-hydroxybenzylidene)- formichydrazide (0.58 g, 3.0 mmol) and Et₃N (0.84 ml, 6 mmol) were added to dry toluene (100 ml) in a 250 ml round bottom flask equipped with a reflux condenser. Diethyltin(IV) dichloride (0.74 g, 3.0 mmol) dissolved in dry toluene (20 ml) was then added. The reaction mixture was stirred at room temperature for 5 h and allowed to stand overnight. The formed Et₃N-HCl was filtered off and the clear yellow solution was evaporated on a rotary evaporator under reduced pressure. Crystals of (I) were obtained by recrystallization from a chloroform solution.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines.

Diethyl[N-(3-methoxy-2-oxidobenzylidene)-N'- (oxidomethylene)hydrazine-κ³O,N,O']tin(IV) top

Crystal data top

[Sn(C₂H₅)₂(C₉H₈N₂O₃)]	Z = 2
M_r = 368.98	F(000) = 368
Triclinic, P1	D_x = 1.729 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2485 (3) Å	Cell parameters from 3603 reflections
b = 9.8609 (4) Å	θ = 2.3–28.7°
c = 10.4501 (4) Å	µ = 1.81 mm⁻¹
α = 63.521 (2)°	T = 296 K
β = 68.967 (1)°	Prismatic, yellow
γ = 77.803 (2)°	0.30 × 0.20 × 0.18 mm
V = 708.79 (5) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	3603 independent reflections
Radiation source: fine-focus sealed tube	3458 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 7.4 pixels mm^-1	θ_max = 28.7°, θ_min = 2.3°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
T_min = 0.650, T_max = 0.720	l = −14→14
14275 measured reflections

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)] = 0.016	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0503P)² + 0.0901P] where P = (F_o² + 2F_c²)/3
3603 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Sn(C₂H₅)₂(C₉H₈N₂O₃)]	γ = 77.803 (2)°
M_r = 368.98	V = 708.79 (5) Å³
Triclinic, P1	Z = 2
a = 8.2485 (3) Å	Mo Kα radiation
b = 9.8609 (4) Å	µ = 1.81 mm⁻¹
c = 10.4501 (4) Å	T = 296 K
α = 63.521 (2)°	0.30 × 0.20 × 0.18 mm
β = 68.967 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3603 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3458 reflections with I > 2σ(I)
T_min = 0.650, T_max = 0.720	R_int = 0.023
14275 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.016	0 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 1.02	Δρ_max = 0.39 e Å⁻³
3603 reflections	Δρ_min = −0.59 e Å⁻³
226 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Sn1	0.134568 (12)	0.080659 (11)	0.280902 (10)	0.02876 (6)
O1	0.07311 (18)	0.14980 (15)	0.46603 (15)	0.0333 (3)
O2	0.2427 (2)	0.11910 (19)	0.04108 (16)	0.0510 (4)
O3	−0.04789 (19)	0.17238 (16)	0.73028 (15)	0.0400 (3)
N1	0.2910 (2)	0.28451 (17)	0.15785 (16)	0.0343 (3)
N2	0.3750 (3)	0.3247 (2)	0.0026 (2)	0.0446 (4)
C1	0.1382 (2)	0.25342 (18)	0.47969 (19)	0.0276 (3)
C2	0.0784 (2)	0.26822 (19)	0.6190 (2)	0.0303 (3)
C3	0.1440 (3)	0.3722 (2)	0.6396 (2)	0.0396 (4)
H3	0.1024	0.3790	0.7320	0.048*
C4	0.2714 (3)	0.4670 (3)	0.5238 (3)	0.0478 (5)
H4	0.3166	0.5354	0.5392	0.057*
C5	0.3298 (3)	0.4587 (2)	0.3872 (3)	0.0447 (4)
H5	0.4144	0.5225	0.3095	0.054*
C6	0.2634 (2)	0.3545 (2)	0.3624 (2)	0.0334 (3)
C7	0.3300 (3)	0.3656 (2)	0.2102 (2)	0.0365 (4)
H7	0.4095	0.4390	0.1427	0.044*
C8	0.3378 (3)	0.2327 (3)	−0.0403 (2)	0.0443 (4)
H8	0.3857	0.2517	−0.1416	0.053*
C9	−0.1144 (2)	0.1569 (2)	0.2494 (2)	0.0394 (4)
H9A	−0.1301	0.1149	0.1869	0.047*
H9B	−0.2029	0.1188	0.3460	0.047*
C10	−0.1400 (4)	0.3268 (3)	0.1781 (5)	0.0777 (9)
H10A	−0.2545	0.3544	0.1668	0.116*
H10B	−0.0547	0.3653	0.0813	0.116*
H10C	−0.1274	0.3692	0.2405	0.116*
C11	0.3323 (3)	−0.0893 (2)	0.3408 (2)	0.0413 (4)
H11A	0.2880	−0.1564	0.4457	0.050*
H11B	0.3580	−0.1491	0.2824	0.050*
C12	0.4986 (3)	−0.0295 (3)	0.3172 (4)	0.0713 (8)
H12A	0.5810	−0.1129	0.3468	0.107*
H12B	0.4755	0.0276	0.3767	0.107*
H12C	0.5456	0.0350	0.2132	0.107*
C13	−0.1177 (4)	0.1920 (3)	0.8682 (2)	0.0545 (6)
H13A	−0.2039	0.1197	0.9374	0.082*
H13B	−0.1702	0.2930	0.8493	0.082*
H13C	−0.0259	0.1764	0.9103	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.02673 (8)	0.03389 (8)	0.02623 (8)	−0.00313 (5)	−0.00603 (5)	−0.01366 (6)
O1	0.0369 (7)	0.0368 (6)	0.0307 (6)	−0.0122 (5)	−0.0037 (5)	−0.0182 (5)
O2	0.0609 (10)	0.0622 (10)	0.0326 (7)	−0.0265 (8)	0.0021 (6)	−0.0241 (7)
O3	0.0483 (8)	0.0442 (7)	0.0324 (6)	−0.0180 (6)	−0.0017 (6)	−0.0213 (6)
N1	0.0332 (7)	0.0351 (7)	0.0284 (7)	−0.0083 (6)	−0.0023 (6)	−0.0103 (6)
N2	0.0493 (10)	0.0467 (9)	0.0286 (8)	−0.0174 (8)	0.0030 (7)	−0.0126 (7)
C1	0.0275 (7)	0.0272 (7)	0.0323 (7)	−0.0016 (6)	−0.0111 (6)	−0.0139 (6)
C2	0.0313 (8)	0.0292 (8)	0.0339 (8)	−0.0025 (6)	−0.0118 (7)	−0.0140 (7)
C3	0.0465 (10)	0.0410 (9)	0.0420 (9)	−0.0065 (8)	−0.0148 (8)	−0.0233 (8)
C4	0.0537 (12)	0.0470 (11)	0.0559 (12)	−0.0178 (9)	−0.0141 (10)	−0.0276 (10)
C5	0.0468 (11)	0.0409 (10)	0.0481 (11)	−0.0190 (8)	−0.0081 (9)	−0.0172 (9)
C6	0.0321 (8)	0.0319 (8)	0.0376 (8)	−0.0059 (6)	−0.0095 (7)	−0.0143 (7)
C7	0.0354 (9)	0.0332 (8)	0.0356 (9)	−0.0105 (7)	−0.0023 (7)	−0.0123 (7)
C8	0.0459 (10)	0.0511 (11)	0.0283 (8)	−0.0121 (9)	0.0007 (7)	−0.0149 (8)
C9	0.0319 (8)	0.0483 (10)	0.0361 (9)	−0.0043 (7)	−0.0132 (7)	−0.0124 (8)
C10	0.0660 (17)	0.0505 (14)	0.112 (3)	0.0168 (13)	−0.0459 (18)	−0.0229 (16)
C11	0.0344 (9)	0.0382 (9)	0.0488 (10)	0.0038 (7)	−0.0101 (8)	−0.0200 (8)
C12	0.0440 (13)	0.0669 (16)	0.118 (3)	0.0075 (11)	−0.0433 (15)	−0.0406 (17)
C13	0.0744 (16)	0.0556 (12)	0.0370 (10)	−0.0203 (11)	−0.0005 (10)	−0.0274 (10)

Geometric parameters (Å, º) top

Sn1—C11	2.1216 (19)	C5—H5	0.9300
Sn1—C9	2.1217 (18)	C6—C7	1.444 (3)
Sn1—O1	2.1888 (13)	C7—H7	0.9300
Sn1—O2	2.2162 (14)	C8—H8	0.9300
Sn1—N1	2.2271 (15)	C9—C10	1.502 (3)
O1—C1	1.3304 (19)	C9—H9A	0.9700
O2—C8	1.278 (3)	C9—H9B	0.9700
O3—C2	1.377 (2)	C10—H10A	0.9600
O3—C13	1.433 (2)	C10—H10B	0.9600
N1—C7	1.291 (2)	C10—H10C	0.9600
N1—N2	1.416 (2)	C11—C12	1.504 (3)
N2—C8	1.304 (3)	C11—H11A	0.9700
C1—C6	1.414 (2)	C11—H11B	0.9700
C1—C2	1.424 (2)	C12—H12A	0.9600
C2—C3	1.380 (2)	C12—H12B	0.9600
C3—C4	1.392 (3)	C12—H12C	0.9600
C3—H3	0.9300	C13—H13A	0.9600
C4—C5	1.368 (3)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C5—C6	1.414 (2)

C11—Sn1—C9	153.45 (9)	N1—C7—H7	116.5
C11—Sn1—O1	97.19 (7)	C6—C7—H7	116.5
C9—Sn1—O1	93.40 (7)	O2—C8—N2	127.32 (18)
C11—Sn1—O2	92.71 (8)	O2—C8—H8	116.3
C9—Sn1—O2	88.78 (7)	N2—C8—H8	116.3
O1—Sn1—O2	152.79 (5)	C10—C9—Sn1	113.26 (16)
C11—Sn1—N1	99.42 (7)	C10—C9—H9A	108.9
C9—Sn1—N1	106.13 (7)	Sn1—C9—H9A	108.9
O1—Sn1—N1	82.07 (5)	C10—C9—H9B	108.9
O2—Sn1—N1	71.30 (6)	Sn1—C9—H9B	108.9
C1—O1—Sn1	131.78 (11)	H9A—C9—H9B	107.7
C8—O2—Sn1	114.11 (13)	C9—C10—H10A	109.5
C2—O3—C13	116.47 (15)	C9—C10—H10B	109.5
C7—N1—N2	113.77 (15)	H10A—C10—H10B	109.5
C7—N1—Sn1	129.00 (12)	C9—C10—H10C	109.5
N2—N1—Sn1	116.91 (12)	H10A—C10—H10C	109.5
C8—N2—N1	110.32 (16)	H10B—C10—H10C	109.5
O1—C1—C6	124.13 (15)	C12—C11—Sn1	114.55 (16)
O1—C1—C2	119.40 (15)	C12—C11—H11A	108.6
C6—C1—C2	116.45 (15)	Sn1—C11—H11A	108.6
O3—C2—C3	122.78 (16)	C12—C11—H11B	108.6
O3—C2—C1	115.59 (14)	Sn1—C11—H11B	108.6
C3—C2—C1	121.62 (17)	H11A—C11—H11B	107.6
C2—C3—C4	120.80 (18)	C11—C12—H12A	109.5
C2—C3—H3	119.6	C11—C12—H12B	109.5
C4—C3—H3	119.6	H12A—C12—H12B	109.5
C5—C4—C3	119.43 (17)	C11—C12—H12C	109.5
C5—C4—H4	120.3	H12A—C12—H12C	109.5
C3—C4—H4	120.3	H12B—C12—H12C	109.5
C4—C5—C6	120.97 (19)	O3—C13—H13A	109.5
C4—C5—H5	119.5	O3—C13—H13B	109.5
C6—C5—H5	119.5	H13A—C13—H13B	109.5
C1—C6—C5	120.65 (17)	O3—C13—H13C	109.5
C1—C6—C7	124.88 (16)	H13A—C13—H13C	109.5
C5—C6—C7	114.44 (17)	H13B—C13—H13C	109.5
N1—C7—C6	126.99 (17)

C11—Sn1—O1—C1	89.09 (16)	C6—C1—C2—C3	−2.2 (3)
C9—Sn1—O1—C1	−115.31 (16)	O3—C2—C3—C4	−179.90 (19)
O2—Sn1—O1—C1	−21.4 (2)	C1—C2—C3—C4	0.1 (3)
N1—Sn1—O1—C1	−9.48 (15)	C2—C3—C4—C5	1.3 (3)
C11—Sn1—O2—C8	−97.99 (17)	C3—C4—C5—C6	−0.5 (4)
C9—Sn1—O2—C8	108.54 (17)	O1—C1—C6—C5	−178.21 (17)
O1—Sn1—O2—C8	13.5 (3)	C2—C1—C6—C5	3.0 (3)
N1—Sn1—O2—C8	1.05 (16)	O1—C1—C6—C7	3.8 (3)
C11—Sn1—N1—C7	−85.14 (18)	C2—C1—C6—C7	−175.00 (18)
C9—Sn1—N1—C7	102.15 (18)	C4—C5—C6—C1	−1.7 (3)
O1—Sn1—N1—C7	10.88 (17)	C4—C5—C6—C7	176.4 (2)
O2—Sn1—N1—C7	−174.82 (19)	N2—N1—C7—C6	178.61 (19)
C11—Sn1—N1—N2	87.99 (15)	Sn1—N1—C7—C6	−8.1 (3)
C9—Sn1—N1—N2	−84.72 (15)	C1—C6—C7—N1	−1.9 (3)
O1—Sn1—N1—N2	−175.99 (16)	C5—C6—C7—N1	−180.0 (2)
O2—Sn1—N1—N2	−1.69 (14)	Sn1—O2—C8—N2	−0.3 (3)
C7—N1—N2—C8	176.23 (19)	N1—N2—C8—O2	−1.2 (3)
Sn1—N1—N2—C8	2.1 (2)	C11—Sn1—C9—C10	−173.4 (2)
Sn1—O1—C1—C6	4.8 (3)	O1—Sn1—C9—C10	73.0 (2)
Sn1—O1—C1—C2	−176.49 (12)	O2—Sn1—C9—C10	−79.8 (2)
C13—O3—C2—C3	3.9 (3)	N1—Sn1—C9—C10	−9.7 (2)
C13—O3—C2—C1	−176.17 (18)	C9—Sn1—C11—C12	176.3 (2)
O1—C1—C2—O3	−1.0 (2)	O1—Sn1—C11—C12	−71.0 (2)
C6—C1—C2—O3	177.81 (15)	O2—Sn1—C11—C12	83.6 (2)
O1—C1—C2—C3	178.91 (17)	N1—Sn1—C11—C12	12.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O2ⁱ	0.96	2.34	3.068 (4)	132

Symmetry code: (i) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Sn(C₂H₅)₂(C₉H₈N₂O₃)]
M_r	368.98
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.2485 (3), 9.8609 (4), 10.4501 (4)
α, β, γ (°)	63.521 (2), 68.967 (1), 77.803 (2)
V (Å³)	708.79 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.81
Crystal size (mm)	0.30 × 0.20 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.650, 0.720
No. of measured, independent and observed [I > 2σ(I)] reflections	14275, 3603, 3458
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.675

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.016, 0.063, 1.02
No. of reflections	3603
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.59

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

Sn1—C11	2.1216 (19)	Sn1—O2	2.2162 (14)
Sn1—C9	2.1217 (18)	Sn1—N1	2.2271 (15)
Sn1—O1	2.1888 (13)

C11—Sn1—C9	153.45 (9)	O1—Sn1—O2	152.79 (5)
C11—Sn1—O1	97.19 (7)	C11—Sn1—N1	99.42 (7)
C9—Sn1—O1	93.40 (7)	C9—Sn1—N1	106.13 (7)
C11—Sn1—O2	92.71 (8)	O1—Sn1—N1	82.07 (5)
C9—Sn1—O2	88.78 (7)	O2—Sn1—N1	71.30 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O2ⁱ	0.96	2.34	3.068 (4)	132.00

Symmetry code: (i) −x, −y, −z+1.

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore, and for financial support to SS for PhD studies under the Indigenous Scholarship Scheme (PIN Code: 042–111889).

References

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