(2,2′-Bipyridine-κ2N,N′){[(3-meth­oxy-2-oxidobenzyl­idene-κO2)hydrazono]methano­lato-κ2N2,O}dimethyl­tin(IV)

Shuja, S.; Ali, S.; Tahir, M.N.; Khalid, N.; Khan, I.U.

doi:10.1107/S1600536808006090

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Pages m531-m532

doi:10.1107/S1600536808006090

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(2,2′-Bipyridine-κ²N,N′){[(3-methoxy-2-oxidobenzylidene-κO²)hydrazono]methanolato-κ²N²,O}dimethyltin(IV)

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

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

(Received 28 February 2008; accepted 5 March 2008; online 7 March 2008)

In the crystal structure of the title compound, [Sn(CH₃)₂(C₉H₈N₂O₃)(C₁₀H₈N₂)], the Sn atom exhibits a pentagonal bipyramidal coordination geometry defined by two C, three N and two O atoms. The bond distances for Sn—C, Sn—N and Sn—O are in the ranges 2.097 (3)–2.098 (3), 2.298 (2)–2.623 (2) and 2.157 (2)–2.266 (2) Å, respectively. The molecular structure of the monomeric compound is stabilized by three intramolecular C—H⋯O hydrogen bonds, all involving bipyridine C—H groups.

Related literature

For related literature, see: Chen et al. (2006 ); Diouf et al. (2004 ); Shuja et al. (2007a ,b , 2007c ). For bond-length data, see: Allen (2002 ).

Experimental

Crystal data

[Sn(CH₃)₂(C₉H₈N₂O₃)(C₁₀H₈N₂)]
M_r = 497.12
Monoclinic, P 2₁ /c
a = 12.3834 (3) Å
b = 9.9094 (2) Å
c = 17.1730 (4) Å
β = 103.302 (1)°
V = 2050.80 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.28 mm⁻¹
T = 296 (2) K
0.25 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.749, T_max = 0.820
24401 measured reflections
5524 independent reflections
4407 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.066
S = 1.04
5524 reflections
280 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.12 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—C9	2.097 (3)
Sn1—C10	2.098 (3)
Sn1—O1	2.1572 (14)
Sn1—O2	2.2658 (15)
Sn1—N1	2.2980 (18)
Sn1—N3	2.5825 (18)
Sn1—N4	2.6231 (19)

C9—Sn1—C10	169.76 (11)
C9—Sn1—O1	93.97 (9)
C10—Sn1—O1	90.20 (9)
C9—Sn1—O2	94.23 (9)
C10—Sn1—O2	87.60 (11)
O1—Sn1—O2	145.23 (6)
C9—Sn1—N1	94.39 (9)
C10—Sn1—N1	95.65 (10)
O1—Sn1—N1	77.12 (6)
O2—Sn1—N1	68.60 (6)
C9—Sn1—N3	80.37 (9)
C10—Sn1—N3	90.33 (9)
O1—Sn1—N3	138.83 (6)
O2—Sn1—N3	75.90 (6)
N1—Sn1—N3	143.65 (6)
O1—Sn1—N4	76.91 (6)
O2—Sn1—N4	136.43 (6)
N1—Sn1—N4	153.65 (6)
N3—Sn1—N4	62.68 (6)
N4—Sn1—C9	91.77 (9)
N4—Sn1—C10	80.06 (10)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2	0.93	2.40	2.993 (3)	121
C21—H21⋯O1	0.93	2.36	2.968 (3)	123
C21—H21⋯O3	0.93	2.50	3.390 (3)	161

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 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808006090/im2056sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808006090/im2056Isup2.hkl

checkCIF report

Comment top

Diorganotin(IV) complexes of Schiff base ligands derived from 3-methoxysalicylaldehyde and hydrazine derivatives are limited in number (Chen et al., 2006, Diouf et al., 2004). In continuation of our efforts to synthesize various Schiff base ligands of substituted salicylaldehydes with hydrazines or amino acids as well as the corresponding organotin derivatives (Shuja et al., 2007a, 2007b, 2007c), we herein report the structure of the title compound (I).

In the monomeric structure of the title compound (I), the coordination around Sn consists of two O-atoms and one N-atom of the Schiff base ligand [N-Formyl-N'-(3-methoxy-2-oxidobenzylidene)hydrazine], two N-atoms of 2,2'-bipyridine and two C-atoms of methyl groups. The shortest bond of Sn is realised with the methyl C-atoms showing nearly equal values (2.097 (3) and 2.098 (3) Å) corresponding very well with the bond lengths observed in [(3-Methoxy-2-oxidobenzaldehyde benzoylhydrazonato)dimethyltin(IV)] (Chen et al., 2006). The Sn1—O1 bond distance of 2.157 (1) Å is greater than the values reported for [diphenyl(methoxy-N-salicylideneacetylhydrazonato)tin(IV)] (2.068 (2) Å, Diouf et al., 2004 and 2.131 (3) Å, Chen et al., 2006). The same is true for the bonds Sn1—O2 (2.266 (2) Å) and Sn1—N1 (2.298 (2) Å) also being longer compared to those previously reported (Diouf et al., 2004, Chen et al., 2006). These observations are most probably due to the additional coordination of bipyridine to tin. A CCDC search (Allen, 2002) showed that the title compund is indeed the first structurally characterized tin organyl with a bipyridine ligand attached to tin. The bond distances of N-atoms of bipyridine measure to 2.583 (2) Å (Sn1—N3) and 2.623 (2) Å (Sn1—N4), respectively. The bond distances in the hydrazine ligand are comparable with those reported for {[N-Formyl-N'-(2-oxidobenzylidene)hydrazine-κ³O,N,O']diphenyl tin(IV)} (Shuja et al., 2007b). The bond angles around Sn1 are in the range between 68.60 (6)° and 169.8 (1)°. The dihedral angle between (O1/C1/C2/C3/C4 /C5/C6/C7) and (N1/N2/C8/O2) is 36.0 (1)° while the angle between the rings (N3/C12/C13/C14/C15/C16) and (N4/C17/C18/C19/C20/C21) is 17.0 (1)°. The molecular structure of the title compound as well as the observed conformation are stabilized by three intramolecular H-bonds of C—H···O type (Fig. 1) all involving bipyridine C–H functions (Table 2). The closest intermolecular contact of molecules is at a distance of 3.208 (3) Å between O1···C15ⁱ [symmetry code: i = x, -y + 1/2, z + 1/2]. A postive electron peak corresponding to 1.12 Å^-3 remains at a distance of 0.93 Å near Sn1.

Related literature top

For related literature, see: Chen et al. (2006); Diouf et al. (2004); Shuja et al. (2007a,b, 2007c). For bond-length data, see: Allen (2002).

Experimental top

N-(2-hydroxy-3-methoxy-benzylidene)formylhydrazine (0.58 g, 3 mmol) and Et₃N (0.86 ml, 6 mmol) were added to anhydrous toluene (100 ml) in a round bottom flask equipped with a reflux condenser. Dimethyltin(IV) dichloride (0.66 g, 3 mmol) dissolved in anhydrous toluene (20 ml) and 2,2'-bipyridine (0.47 g, 3 mmol) were then added. The reaction mixture was stirred at room temperature for 5 hr and allowed to stand overnight. The Et₃NHCl salt formed during the reaction was filtered off and the resulting clear yellow solution was evaporated with a rotary evaporator under reduced pressure. Recrystallization from chloroform yielded crystals suitable for X-ray diffraction.

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) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top

	Fig. 1. ORTEP-3 for Windows (Farrugia, 1997) drawing of the title compound, C₂₁H₂₂N₄O₃Sn with the atom numbering scheme. The thermal ellipsoids are drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii. The intramolecular H-bonding is shown by dashed lines.
	Fig. 2. The unit cell packing of (I) (Spek, 2003), showing that there is no intermolecular hydrogen bonding.

(I) top

Crystal data top

[Sn(CH₃)₂(C₉H₈N₂O₃)(C₁₀H₈N₂)]	F(000) = 1000
M_r = 497.12	D_x = 1.610 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4407 reflections
a = 12.3834 (3) Å	θ = 1.7–29.2°
b = 9.9094 (2) Å	µ = 1.28 mm⁻¹
c = 17.1730 (4) Å	T = 296 K
β = 103.302 (1)°	Prismatic, yellow
V = 2050.80 (8) Å³	0.25 × 0.18 × 0.15 mm
Z = 4

Data collection top

Bruker KappaAPEXII CCD diffractometer	5524 independent reflections
Radiation source: fine-focus sealed tube	4407 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 7.3 pixels mm^-1	θ_max = 29.2°, θ_min = 1.7°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→12
T_min = 0.749, T_max = 0.820	l = −23→23
24401 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0299P)² + 0.9401P] where P = (F_o² + 2F_c²)/3
5524 reflections	(Δ/σ)_max = 0.003
280 parameters	Δρ_max = 1.12 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Sn(CH₃)₂(C₉H₈N₂O₃)(C₁₀H₈N₂)]	V = 2050.80 (8) Å³
M_r = 497.12	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3834 (3) Å	µ = 1.28 mm⁻¹
b = 9.9094 (2) Å	T = 296 K
c = 17.1730 (4) Å	0.25 × 0.18 × 0.15 mm
β = 103.302 (1)°

Data collection top

Bruker KappaAPEXII CCD diffractometer	5524 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4407 reflections with I > 2σ(I)
T_min = 0.749, T_max = 0.820	R_int = 0.028
24401 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 1.12 e Å⁻³
5524 reflections	Δρ_min = −0.41 e Å⁻³
280 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 > σ(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	0.268225 (12)	0.389388 (13)	1.008997 (8)	0.03310 (5)
O1	0.22028 (13)	0.22099 (15)	1.07319 (9)	0.0415 (4)
O2	0.31515 (18)	0.61079 (15)	1.01551 (11)	0.0514 (4)
O3	0.11847 (15)	−0.01098 (16)	1.07144 (11)	0.0528 (4)
N1	0.23627 (17)	0.48884 (18)	1.12248 (11)	0.0425 (4)
N2	0.2877 (2)	0.6145 (2)	1.14445 (14)	0.0565 (6)
N3	0.31169 (16)	0.43881 (18)	0.87174 (11)	0.0383 (4)
N4	0.29433 (16)	0.18153 (18)	0.92055 (11)	0.0408 (4)
C1	0.13973 (19)	0.2149 (2)	1.11147 (13)	0.0387 (5)
C2	0.0823 (2)	0.0913 (2)	1.11224 (14)	0.0442 (5)
C3	−0.0043 (2)	0.0808 (3)	1.15032 (17)	0.0594 (7)
H3	−0.0432	0.0001	1.1482	0.071*
C4	−0.0336 (3)	0.1904 (3)	1.19174 (18)	0.0671 (8)
H4	−0.0921	0.1829	1.2171	0.081*
C5	0.0230 (2)	0.3077 (3)	1.19522 (16)	0.0572 (7)
H5	0.0041	0.3795	1.2244	0.069*
C6	0.1101 (2)	0.3234 (2)	1.15545 (13)	0.0425 (5)
C7	0.1685 (2)	0.4502 (3)	1.16414 (14)	0.0467 (6)
H7	0.1559	0.5090	1.2033	0.056*
C8	0.3242 (2)	0.6617 (3)	1.08479 (16)	0.0556 (7)
H8	0.3620	0.7434	1.0939	0.067*
C9	0.1069 (2)	0.4231 (3)	0.94090 (17)	0.0460 (6)
H9A	0.056 (3)	0.407 (3)	0.969 (2)	0.069*
H9B	0.093 (3)	0.370 (3)	0.896 (2)	0.069*
H9C	0.099 (2)	0.506 (3)	0.9240 (18)	0.069*
C10	0.4361 (2)	0.3463 (3)	1.05755 (18)	0.0523 (6)
H10A	0.477 (3)	0.366 (3)	1.027 (2)	0.078*
H10B	0.444 (3)	0.252 (3)	1.0710 (18)	0.078*
H10C	0.463 (3)	0.399 (3)	1.104 (2)	0.078*
C11	0.0699 (3)	−0.1410 (3)	1.07460 (19)	0.0639 (8)
H11A	0.1023	−0.2040	1.0441	0.096*
H11B	−0.0086	−0.1358	1.0527	0.096*
H11C	0.0835	−0.1707	1.1292	0.096*
C12	0.2997 (2)	0.5636 (2)	0.84114 (15)	0.0469 (6)
H12	0.2818	0.6325	0.8727	0.056*
C13	0.3121 (2)	0.5960 (2)	0.76579 (15)	0.0510 (6)
H13	0.3021	0.6840	0.7468	0.061*
C14	0.3398 (2)	0.4948 (3)	0.71961 (15)	0.0557 (7)
H14	0.3498	0.5134	0.6687	0.067*
C15	0.3526 (2)	0.3653 (3)	0.74940 (14)	0.0504 (6)
H15	0.3717	0.2957	0.7188	0.060*
C16	0.33668 (17)	0.3393 (2)	0.82525 (12)	0.0363 (4)
C17	0.34066 (18)	0.2002 (2)	0.85795 (13)	0.0378 (5)
C18	0.3865 (2)	0.0940 (3)	0.82431 (16)	0.0530 (6)
H18	0.4185	0.1088	0.7811	0.064*
C19	0.3843 (3)	−0.0340 (3)	0.85548 (18)	0.0630 (8)
H19	0.4156	−0.1060	0.8338	0.076*
C20	0.3361 (3)	−0.0541 (3)	0.91812 (17)	0.0580 (7)
H20	0.3328	−0.1399	0.9393	0.070*
C21	0.2919 (2)	0.0563 (2)	0.94976 (16)	0.0506 (6)
H21	0.2593	0.0429	0.9928	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03738 (9)	0.02873 (8)	0.03378 (8)	−0.00102 (6)	0.00941 (6)	−0.00056 (5)
O1	0.0526 (9)	0.0335 (8)	0.0437 (9)	0.0000 (7)	0.0223 (7)	0.0018 (6)
O2	0.0729 (12)	0.0353 (8)	0.0494 (10)	−0.0122 (8)	0.0214 (9)	−0.0058 (7)
O3	0.0625 (11)	0.0398 (9)	0.0580 (11)	−0.0116 (8)	0.0180 (9)	0.0027 (8)
N1	0.0546 (12)	0.0355 (9)	0.0383 (10)	−0.0012 (8)	0.0128 (9)	−0.0050 (8)
N2	0.0823 (17)	0.0419 (11)	0.0469 (12)	−0.0131 (10)	0.0181 (12)	−0.0141 (9)
N3	0.0462 (11)	0.0341 (9)	0.0345 (9)	−0.0023 (8)	0.0091 (8)	0.0016 (7)
N4	0.0515 (11)	0.0322 (9)	0.0417 (10)	0.0015 (8)	0.0171 (9)	0.0008 (8)
C1	0.0434 (12)	0.0430 (12)	0.0301 (10)	−0.0003 (9)	0.0093 (9)	0.0070 (9)
C2	0.0502 (14)	0.0445 (13)	0.0379 (12)	−0.0018 (10)	0.0101 (11)	0.0088 (9)
C3	0.0587 (17)	0.0640 (17)	0.0588 (17)	−0.0135 (13)	0.0204 (14)	0.0175 (13)
C4	0.0664 (19)	0.076 (2)	0.0713 (19)	0.0012 (15)	0.0403 (16)	0.0179 (16)
C5	0.0649 (17)	0.0664 (18)	0.0490 (15)	0.0104 (14)	0.0311 (13)	0.0086 (12)
C6	0.0502 (13)	0.0465 (13)	0.0336 (11)	0.0046 (10)	0.0154 (10)	0.0057 (9)
C7	0.0622 (16)	0.0455 (13)	0.0354 (12)	0.0060 (11)	0.0176 (11)	−0.0026 (10)
C8	0.0755 (19)	0.0366 (12)	0.0558 (16)	−0.0149 (12)	0.0172 (14)	−0.0122 (11)
C9	0.0414 (13)	0.0469 (13)	0.0488 (15)	0.0023 (11)	0.0085 (11)	0.0030 (11)
C10	0.0409 (14)	0.0609 (16)	0.0540 (16)	0.0022 (12)	0.0089 (12)	0.0071 (13)
C11	0.075 (2)	0.0450 (14)	0.0666 (18)	−0.0154 (13)	0.0046 (15)	0.0119 (13)
C12	0.0601 (16)	0.0368 (11)	0.0420 (13)	−0.0029 (11)	0.0080 (11)	0.0053 (10)
C13	0.0586 (16)	0.0459 (13)	0.0443 (13)	−0.0095 (11)	0.0030 (12)	0.0123 (10)
C14	0.0630 (17)	0.0678 (17)	0.0354 (13)	−0.0094 (13)	0.0095 (12)	0.0131 (12)
C15	0.0595 (16)	0.0587 (15)	0.0349 (12)	−0.0012 (12)	0.0147 (11)	−0.0012 (10)
C16	0.0359 (11)	0.0404 (11)	0.0324 (10)	−0.0029 (9)	0.0072 (9)	−0.0001 (9)
C17	0.0413 (12)	0.0374 (11)	0.0341 (11)	0.0010 (9)	0.0075 (9)	−0.0027 (8)
C18	0.0666 (18)	0.0526 (15)	0.0438 (14)	0.0124 (12)	0.0208 (13)	−0.0028 (11)
C19	0.086 (2)	0.0432 (14)	0.0623 (17)	0.0189 (14)	0.0222 (16)	−0.0097 (12)
C20	0.079 (2)	0.0317 (12)	0.0644 (17)	0.0067 (12)	0.0197 (15)	−0.0009 (12)
C21	0.0698 (17)	0.0313 (11)	0.0570 (15)	0.0013 (11)	0.0278 (13)	0.0019 (10)

Geometric parameters (Å, º) top

Sn1—C9	2.097 (3)	C7—H7	0.9300
Sn1—C10	2.098 (3)	C8—H8	0.9300
Sn1—O1	2.1572 (14)	C9—H9A	0.90 (3)
Sn1—O2	2.2658 (15)	C9—H9B	0.92 (3)
Sn1—N1	2.2980 (18)	C9—H9C	0.87 (3)
Sn1—N3	2.5825 (18)	C10—H10A	0.84 (3)
Sn1—N4	2.6231 (19)	C10—H10B	0.96 (3)
O1—C1	1.316 (2)	C10—H10C	0.95 (3)
O2—C8	1.273 (3)	C11—H11A	0.9600
O3—C2	1.365 (3)	C11—H11B	0.9600
O3—C11	1.428 (3)	C11—H11C	0.9600
N1—C7	1.280 (3)	C12—C13	1.376 (3)
N1—N2	1.410 (3)	C12—H12	0.9300
N2—C8	1.298 (3)	C13—C14	1.369 (4)
N3—C12	1.338 (3)	C13—H13	0.9300
N3—C16	1.349 (3)	C14—C15	1.378 (3)
N4—C21	1.341 (3)	C14—H14	0.9300
N4—C17	1.343 (3)	C15—C16	1.385 (3)
C1—C6	1.410 (3)	C15—H15	0.9300
C1—C2	1.417 (3)	C16—C17	1.486 (3)
C2—C3	1.383 (3)	C17—C18	1.383 (3)
C3—C4	1.391 (4)	C18—C19	1.379 (4)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.352 (4)	C19—C20	1.360 (4)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.412 (3)	C20—C21	1.389 (3)
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.441 (4)	C21—H21	0.9300

C9—Sn1—C10	169.76 (11)	N1—C7—H7	117.2
C9—Sn1—O1	93.97 (9)	C6—C7—H7	117.2
C10—Sn1—O1	90.20 (9)	O2—C8—N2	128.5 (2)
C9—Sn1—O2	94.23 (9)	O2—C8—H8	115.7
C10—Sn1—O2	87.60 (11)	N2—C8—H8	115.7
O1—Sn1—O2	145.23 (6)	Sn1—C9—H9A	111 (2)
C9—Sn1—N1	94.39 (9)	Sn1—C9—H9B	110 (2)
C10—Sn1—N1	95.65 (10)	H9A—C9—H9B	110 (3)
O1—Sn1—N1	77.12 (6)	Sn1—C9—H9C	110 (2)
O2—Sn1—N1	68.60 (6)	H9A—C9—H9C	109 (3)
C9—Sn1—N3	80.37 (9)	H9B—C9—H9C	106 (3)
C10—Sn1—N3	90.33 (9)	Sn1—C10—H10A	113 (2)
O1—Sn1—N3	138.83 (6)	Sn1—C10—H10B	109.5 (19)
O2—Sn1—N3	75.90 (6)	H10A—C10—H10B	109 (3)
N1—Sn1—N3	143.65 (6)	Sn1—C10—H10C	110 (2)
O1—Sn1—N4	76.91 (6)	H10A—C10—H10C	105 (3)
O2—Sn1—N4	136.43 (6)	H10B—C10—H10C	110 (3)
N1—Sn1—N4	153.65 (6)	O3—C11—H11A	109.5
N3—Sn1—N4	62.68 (6)	O3—C11—H11B	109.5
N4—Sn1—C9	91.77 (9)	H11A—C11—H11B	109.5
N4—Sn1—C10	80.06 (10)	O3—C11—H11C	109.5
Sn1—N4—C17	119.20 (14)	H11A—C11—H11C	109.5
Sn1—N4—C21	119.56 (14)	H11B—C11—H11C	109.5
C17—N4—C21	118.5 (2)	N3—C12—C13	124.0 (2)
C1—O1—Sn1	128.33 (14)	N3—C12—H12	118.0
C8—O2—Sn1	113.35 (15)	C13—C12—H12	118.0
C2—O3—C11	117.4 (2)	C14—C13—C12	118.1 (2)
C7—N1—N2	115.4 (2)	C14—C13—H13	120.9
C7—N1—Sn1	127.50 (16)	C12—C13—H13	120.9
N2—N1—Sn1	116.77 (14)	C13—C14—C15	119.3 (2)
C8—N2—N1	109.0 (2)	C13—C14—H14	120.3
C12—N3—C16	117.6 (2)	C15—C14—H14	120.3
C12—N3—Sn1	120.40 (16)	C14—C15—C16	119.5 (2)
C16—N3—Sn1	121.75 (14)	C14—C15—H15	120.2
C21—N4—C17	118.52 (19)	C16—C15—H15	120.2
O1—C1—C6	123.5 (2)	N3—C16—C15	121.5 (2)
O1—C1—C2	119.0 (2)	N3—C16—C17	116.54 (19)
C6—C1—C2	117.4 (2)	C15—C16—C17	121.9 (2)
O3—C2—C3	124.7 (2)	N4—C17—C18	121.4 (2)
O3—C2—C1	114.3 (2)	N4—C17—C16	116.58 (19)
C3—C2—C1	121.0 (2)	C18—C17—C16	122.0 (2)
C2—C3—C4	120.3 (3)	C19—C18—C17	119.4 (2)
C2—C3—H3	119.9	C19—C18—H18	120.3
C4—C3—H3	119.9	C17—C18—H18	120.3
C5—C4—C3	120.1 (2)	C20—C19—C18	119.6 (2)
C5—C4—H4	120.0	C20—C19—H19	120.2
C3—C4—H4	120.0	C18—C19—H19	120.2
C4—C5—C6	121.3 (3)	C19—C20—C21	118.6 (2)
C4—C5—H5	119.4	C19—C20—H20	120.7
C6—C5—H5	119.4	C21—C20—H20	120.7
C1—C6—C5	119.8 (2)	N4—C21—C20	122.5 (2)
C1—C6—C7	122.3 (2)	N4—C21—H21	118.7
C5—C6—C7	117.8 (2)	C20—C21—H21	118.7
N1—C7—C6	125.5 (2)

C9—Sn1—O1—C1	−51.1 (2)	O3—C2—C3—C4	178.7 (3)
C10—Sn1—O1—C1	138.3 (2)	C1—C2—C3—C4	−2.8 (4)
O2—Sn1—O1—C1	52.2 (2)	C2—C3—C4—C5	−0.3 (5)
N1—Sn1—O1—C1	42.51 (18)	C3—C4—C5—C6	1.9 (5)
N3—Sn1—O1—C1	−131.00 (17)	O1—C1—C6—C5	−179.6 (2)
C9—Sn1—O2—C8	108.9 (2)	C2—C1—C6—C5	−2.6 (3)
C10—Sn1—O2—C8	−81.2 (2)	O1—C1—C6—C7	−1.9 (4)
O1—Sn1—O2—C8	5.7 (3)	C2—C1—C6—C7	175.1 (2)
N1—Sn1—O2—C8	15.83 (19)	C4—C5—C6—C1	−0.4 (4)
N3—Sn1—O2—C8	−172.1 (2)	C4—C5—C6—C7	−178.1 (3)
C9—Sn1—N1—C7	63.7 (2)	N2—N1—C7—C6	−177.0 (2)
C10—Sn1—N1—C7	−118.3 (2)	Sn1—N1—C7—C6	10.3 (4)
O1—Sn1—N1—C7	−29.4 (2)	C1—C6—C7—N1	14.3 (4)
O2—Sn1—N1—C7	156.5 (2)	C5—C6—C7—N1	−168.0 (2)
N3—Sn1—N1—C7	143.42 (19)	Sn1—O2—C8—N2	−16.6 (4)
C9—Sn1—N1—N2	−108.85 (18)	N1—N2—C8—O2	2.1 (4)
C10—Sn1—N1—N2	69.17 (19)	C16—N3—C12—C13	−0.5 (4)
O1—Sn1—N1—N2	158.07 (18)	Sn1—N3—C12—C13	−174.4 (2)
O2—Sn1—N1—N2	−16.02 (17)	N3—C12—C13—C14	−0.8 (4)
N3—Sn1—N1—N2	−29.1 (2)	C12—C13—C14—C15	0.9 (4)
C7—N1—N2—C8	−159.7 (2)	C13—C14—C15—C16	0.3 (4)
Sn1—N1—N2—C8	13.8 (3)	C12—N3—C16—C15	1.8 (3)
C9—Sn1—N3—C12	70.26 (19)	Sn1—N3—C16—C15	175.57 (18)
C10—Sn1—N3—C12	−114.1 (2)	C12—N3—C16—C17	−175.2 (2)
O1—Sn1—N3—C12	155.26 (17)	Sn1—N3—C16—C17	−1.5 (3)
O2—Sn1—N3—C12	−26.62 (18)	C14—C15—C16—N3	−1.7 (4)
N1—Sn1—N3—C12	−14.0 (2)	C14—C15—C16—C17	175.1 (2)
C9—Sn1—N3—C16	−103.34 (18)	C21—N4—C17—C18	−0.8 (4)
C10—Sn1—N3—C16	72.34 (18)	C21—N4—C17—C16	177.2 (2)
O1—Sn1—N3—C16	−18.3 (2)	N3—C16—C17—N4	15.3 (3)
O2—Sn1—N3—C16	159.78 (18)	C15—C16—C17—N4	−161.8 (2)
N1—Sn1—N3—C16	172.37 (15)	N3—C16—C17—C18	−166.7 (2)
Sn1—O1—C1—C6	−36.9 (3)	C15—C16—C17—C18	16.3 (4)
Sn1—O1—C1—C2	146.18 (17)	N4—C17—C18—C19	0.2 (4)
C11—O3—C2—C3	−5.9 (4)	C16—C17—C18—C19	−177.7 (3)
C11—O3—C2—C1	175.5 (2)	C17—C18—C19—C20	0.8 (5)
O1—C1—C2—O3	−0.1 (3)	C18—C19—C20—C21	−1.1 (5)
C6—C1—C2—O3	−177.2 (2)	C17—N4—C21—C20	0.5 (4)
O1—C1—C2—C3	−178.7 (2)	C19—C20—C21—N4	0.5 (5)
C6—C1—C2—C3	4.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2	0.93	2.40	2.993 (3)	121
C21—H21···O1	0.93	2.36	2.968 (3)	123
C21—H21···O3	0.93	2.50	3.390 (3)	161

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₂(C₉H₈N₂O₃)(C₁₀H₈N₂)]
M_r	497.12
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.3834 (3), 9.9094 (2), 17.1730 (4)
β (°)	103.302 (1)
V (Å³)	2050.80 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.28
Crystal size (mm)	0.25 × 0.18 × 0.15

Data collection
Diffractometer	Bruker KappaAPEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.749, 0.820
No. of measured, independent and observed [I > 2σ(I)] reflections	24401, 5524, 4407
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.066, 1.04
No. of reflections	5524
No. of parameters	280
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.12, −0.41

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

Selected geometric parameters (Å, º) top

Sn1—C9	2.097 (3)	Sn1—N1	2.2980 (18)
Sn1—C10	2.098 (3)	Sn1—N3	2.5825 (18)
Sn1—O1	2.1572 (14)	Sn1—N4	2.6231 (19)
Sn1—O2	2.2658 (15)

C9—Sn1—C10	169.76 (11)	C10—Sn1—N3	90.33 (9)
C9—Sn1—O1	93.97 (9)	O1—Sn1—N3	138.83 (6)
C10—Sn1—O1	90.20 (9)	O2—Sn1—N3	75.90 (6)
C9—Sn1—O2	94.23 (9)	N1—Sn1—N3	143.65 (6)
C10—Sn1—O2	87.60 (11)	O1—Sn1—N4	76.91 (6)
O1—Sn1—O2	145.23 (6)	O2—Sn1—N4	136.43 (6)
C9—Sn1—N1	94.39 (9)	N1—Sn1—N4	153.65 (6)
C10—Sn1—N1	95.65 (10)	N3—Sn1—N4	62.68 (6)
O1—Sn1—N1	77.12 (6)	N4—Sn1—C9	91.77 (9)
O2—Sn1—N1	68.60 (6)	N4—Sn1—C10	80.06 (10)
C9—Sn1—N3	80.37 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2	0.93	2.40	2.993 (3)	121
C21—H21···O1	0.93	2.36	2.968 (3)	123
C21—H21···O3	0.93	2.50	3.390 (3)	161

Acknowledgements

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

References

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