Crystal structure of catena-poly[[tri­methyl­tin(IV)]-μ-2-(2-nitro­phen­yl)acetato-κ2O:O′]

Danish, M.; Tahir, M.N.; Iftikhar, S.; Raza, M.A.; Ashfaq, M.

doi:10.1107/S205698901500198X

metal-organic compounds

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Volume 71| Part 3| March 2015| Pages m52-m53

doi:10.1107/S205698901500198X

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Crystal structure of catena-poly[[trimethyltin(IV)]-μ-2-(2-nitrophenyl)acetato-κ²O:O′]

Muhammad Danish,^a Muhammad Nawaz Tahir,^b ^* Sana Iftikhar,^a Muhammad Asam Raza ^a and Muhammad Ashfaq ^a

^aDepartment of Chemistry, Institute of Natural Sciences, University of Gujrat, Gujrat 50700, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Punjab, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 27 January 2015; accepted 30 January 2015; online 4 February 2015)

In the title one-dimensional coordination polymer, [Sn(CH₃)₃(C₈H₆NO₄)]_n, the Sn^IV atom is coordinated by three methyl C atoms and two carboxylate O atoms (one symmetry generated), resulting in an almost regular SnC₃O₂ trigonal pyramid. The C atoms occupy the equatorial sites and the O atoms occupy the axial sites. In the ligand, the dihedral angles between the benzene ring and the pendant acetate and nitro groups are 57.7 (1) and 36.9 (3)°, respectively. The bridging ligand leads to [010] chains in the crystal, with adjacent metal atoms related by a 2₁ screw axis. A weak π–π interaction exists between the centroids of symmetry-related benzene rings at a distance of 3.9131 (19) Å.

Keywords: crystal structure; one-dimensional coordination polymer; trimethyltin(IV) complex; π–π interaction.

CCDC reference: 1046314

1. Related literature

For related structures see: Tahir et al. (1997a ,b ); Tariq et al. (2013 ); Yang et al. (2009 ); Wen et al. (2009 ); Danish et al. (2015 ).

2. Experimental

2.1. Crystal data

[Sn(CH₃)₃(C₈H₆NO₄)]
M_r = 343.93
Monoclinic, C 2/c
a = 12.6068 (5) Å
b = 9.9798 (4) Å
c = 22.7581 (9) Å
β = 100.174 (2)°
V = 2818.25 (19) Å³
Z = 8
Mo Kα radiation
μ = 1.82 mm⁻¹
T = 296 K
0.40 × 0.32 × 0.28 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan SADABS (Bruker, 2005 ) T_min = 0.532, T_max = 0.631
11546 measured reflections
3074 independent reflections
2734 reflections with I > 2σ(I)
R_int = 0.022

2.3. Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.057
S = 1.10
3070 reflections
157 parameters
H-atom parameters constrained
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—C3	2.114 (3)
Sn1—C2	2.120 (3)
Sn1—C1	2.121 (3)
Sn1—O1	2.1970 (18)
Sn1—O2ⁱ	2.359 (2)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (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: ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Supporting information

CCDC reference: 1046314

Crystal structure: contains datablocks global, I. DOI: 10.1107/S205698901500198X/hb7359sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S205698901500198X/hb7359Isup2.hkl

checkCIF report

Comment top

The tin complex (I), (Fig. 1) is in continuation of synthesizing various metal complexes with (2-nitrophenyl)acetic acid. In this context, we have reported the cobalt complex namely "Tetraaquabis((2-nitrophenyl)acetato-O) cobalt(II)" (Danish et al., 2015).

The crystal structures of catena-Poly[[trimethyltin(IV)]-µ-2-(2-chlorophenyl) acetato] (Wen et al., 2009), catena-[bis(µ2–3-(2- fluorophenyl)-2-methylprop-2-enoato)-hexamethyl-di-tin] (Tariq et al., 2013), catena-poly[[trimethyltin(IV)]-µ-2-(3-thienyl)acetato] (Yang et al., 2009), catena-((µ2–2-(3-benzoylphenyl)propanoato-)- trimethyl-tin(iv)) (Tahir et al., 1997a), {2-[(2,3-Dimethylphenyl)amino] benzoato-O:O'}trimethyltin(IV) (Tahir et al., 1997b) have been published which are related to the title compound due to coordination around the tin.

The Sn atom has a distorted trigonal bipyramidal geometry. The basal plane consists of three methyl groups and the apical position are occupied by the O-atoms of two carboxylate ligands. The Sn atom is 0.1082 (20) Å out of the equatorial plane towards the more strongly bound O1 atom. The Sn—O bond lengths are significantly different [Snl–O1 2.197 (2) and Snl–O2 2.359 (2) Å]. In the asymmetric unit the acetato moiety A (O1/C4/C5/O2), benzene ring B (C6–C11) are planar with r.m.s. deviation of 0.0020 and 0.0059 Å, respectively. The dihedral angle between A/B is 57.727 (115)°. The nitro group is oriented at a dihedtal angle of 36.896 (298)° with the benzene ring. The molecules form one-dimensional polymeric chains (Fig. 2) running along the crystallographic b-axis. There exist a π–π interaction between Cg1···Cg1ⁱ [i = 1 - x, -y, -z] at a distance of 3.9131 (19) Å, where Cg1 is the centroid of benzene ring.

Related literature top

For related structures see: Tahir et al. (1997a,b); Tariq et al. (2013); Yang et al. (2009); Wen et al. (2009); Danish et al. (2015).

Experimental top

The silver salt (1.44 g, 0.01 M) of 2-nitrophenyl acetic acid was suspended in 50 ml chloroform in a round bottom flask equipped with condenser and magnetic stirrer. Trimethyltin chloride (0.995 g, 0.01 M) in 5 ml of chloroform was added under inert atmosphere and reflux the reaction mixture for 4 h. The reaction mixture was allowed to cool to room temperature and stayed overnight then filtered. The residue was washed with chloroform and collected. It was concentrated on rotary evaporated and kept for crystallization. Colourless prisms were obtained after a week.

Computing details top

Data collection: APEX2 (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: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Fragment of an [010] chain in the structure of the title compound.

catena-poly[[trimethyltin(IV)]-µ-2-(2-nitrophenyl)acetato-κ²O:O'] top

Crystal data top

[Sn(CH₃)₃(C₈H₆NO₄)]	F(000) = 1360
M_r = 343.93	D_x = 1.621 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.6068 (5) Å	Cell parameters from 2734 reflections
b = 9.9798 (4) Å	θ = 1.8–27.0°
c = 22.7581 (9) Å	µ = 1.82 mm⁻¹
β = 100.174 (2)°	T = 296 K
V = 2818.25 (19) Å³	Prism, white
Z = 8	0.40 × 0.32 × 0.28 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3074 independent reflections
Radiation source: fine-focus sealed tube	2734 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 7.80 pixels mm^-1	θ_max = 27.0°, θ_min = 1.8°
ω scans	h = −16→15
Absorption correction: multi-scan SADABS (Bruker, 2005)	k = −12→12
T_min = 0.532, T_max = 0.631	l = −29→29
11546 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) = 0.057	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0174P)² + 4.9157P] where P = (F_o² + 2F_c²)/3
3070 reflections	(Δ/σ)_max = 0.002
157 parameters	Δρ_max = 0.74 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Sn(CH₃)₃(C₈H₆NO₄)]	V = 2818.25 (19) Å³
M_r = 343.93	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 12.6068 (5) Å	µ = 1.82 mm⁻¹
b = 9.9798 (4) Å	T = 296 K
c = 22.7581 (9) Å	0.40 × 0.32 × 0.28 mm
β = 100.174 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3074 independent reflections
Absorption correction: multi-scan SADABS (Bruker, 2005)	2734 reflections with I > 2σ(I)
T_min = 0.532, T_max = 0.631	R_int = 0.022
11546 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.057	H-atom parameters constrained
S = 1.10	Δρ_max = 0.74 e Å⁻³
3070 reflections	Δρ_min = −0.53 e Å⁻³
157 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	0.69602 (2)	0.44371 (2)	0.23090 (2)	0.04257 (7)
O1	0.61758 (15)	0.28730 (18)	0.17044 (8)	0.0471 (4)
O2	0.72746 (19)	0.1326 (2)	0.21529 (9)	0.0624 (6)
O3	0.6779 (3)	0.4159 (3)	0.04647 (14)	0.1042 (10)
O4	0.7472 (2)	0.2230 (3)	0.07130 (12)	0.0876 (8)
N1	0.6705 (3)	0.2954 (3)	0.05335 (12)	0.0681 (8)
C1	0.6587 (3)	0.3576 (3)	0.30997 (13)	0.0573 (7)
H1A	0.5941	0.3052	0.3003	0.086*
H1B	0.6480	0.4275	0.3373	0.086*
H1C	0.7170	0.3011	0.3281	0.086*
C2	0.5890 (3)	0.5844 (3)	0.18216 (15)	0.0633 (8)
H2A	0.5272	0.5954	0.2010	0.095*
H2B	0.5664	0.5527	0.1421	0.095*
H2C	0.6250	0.6690	0.1813	0.095*
C3	0.8483 (3)	0.4203 (4)	0.20539 (16)	0.0690 (9)
H3A	0.8964	0.3757	0.2367	0.104*
H3B	0.8770	0.5068	0.1984	0.104*
H3C	0.8406	0.3679	0.1695	0.104*
C4	0.6539 (2)	0.1693 (3)	0.17451 (12)	0.0464 (6)
C5	0.6056 (3)	0.0706 (3)	0.12693 (13)	0.0569 (8)
H5A	0.6640	0.0225	0.1137	0.068*
H5B	0.5639	0.0056	0.1450	0.068*
C6	0.5342 (2)	0.1286 (3)	0.07277 (11)	0.0444 (6)
C7	0.4315 (3)	0.0782 (3)	0.05457 (13)	0.0535 (7)
H7	0.4080	0.0084	0.0761	0.064*
C8	0.3627 (3)	0.1280 (4)	0.00569 (14)	0.0617 (8)
H8	0.2946	0.0907	−0.0056	0.074*
C9	0.3944 (3)	0.2319 (4)	−0.02628 (15)	0.0684 (9)
H9	0.3480	0.2656	−0.0593	0.082*
C10	0.4947 (3)	0.2861 (3)	−0.00945 (14)	0.0641 (8)
H10	0.5163	0.3580	−0.0305	0.077*
C11	0.5636 (2)	0.2338 (3)	0.03875 (12)	0.0490 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.04503 (11)	0.04110 (11)	0.04012 (11)	−0.00067 (8)	0.00347 (7)	0.00225 (8)
O1	0.0541 (11)	0.0384 (10)	0.0459 (10)	0.0023 (8)	0.0006 (8)	−0.0024 (8)
O2	0.0797 (15)	0.0481 (12)	0.0518 (12)	0.0101 (11)	−0.0096 (11)	0.0010 (9)
O3	0.116 (2)	0.093 (2)	0.104 (2)	−0.0586 (19)	0.0209 (18)	0.0090 (17)
O4	0.0527 (14)	0.133 (3)	0.0780 (17)	−0.0086 (16)	0.0135 (13)	−0.0147 (17)
N1	0.0668 (19)	0.086 (2)	0.0540 (16)	−0.0253 (17)	0.0186 (14)	−0.0068 (15)
C1	0.0634 (19)	0.0589 (18)	0.0512 (17)	0.0007 (15)	0.0141 (14)	0.0050 (14)
C2	0.066 (2)	0.0493 (17)	0.068 (2)	0.0012 (15)	−0.0085 (16)	0.0092 (15)
C3	0.0542 (19)	0.085 (2)	0.070 (2)	−0.0089 (17)	0.0177 (16)	−0.0059 (18)
C4	0.0551 (16)	0.0409 (14)	0.0416 (14)	−0.0017 (12)	0.0039 (12)	0.0019 (11)
C5	0.073 (2)	0.0393 (15)	0.0527 (17)	0.0006 (14)	−0.0041 (14)	−0.0015 (12)
C6	0.0546 (16)	0.0384 (13)	0.0396 (13)	−0.0023 (12)	0.0066 (12)	−0.0056 (11)
C7	0.0619 (18)	0.0480 (16)	0.0519 (16)	−0.0125 (13)	0.0139 (14)	−0.0047 (13)
C8	0.0505 (17)	0.074 (2)	0.0588 (19)	−0.0074 (16)	0.0050 (14)	−0.0105 (17)
C9	0.071 (2)	0.076 (2)	0.0523 (18)	0.0025 (18)	−0.0070 (16)	0.0032 (17)
C10	0.084 (2)	0.0593 (19)	0.0479 (17)	−0.0088 (18)	0.0076 (16)	0.0102 (15)
C11	0.0508 (16)	0.0533 (16)	0.0429 (14)	−0.0090 (13)	0.0088 (12)	−0.0046 (12)

Geometric parameters (Å, º) top

Sn1—C3	2.114 (3)	C3—H3A	0.9600
Sn1—C2	2.120 (3)	C3—H3B	0.9600
Sn1—C1	2.121 (3)	C3—H3C	0.9600
Sn1—O1	2.1970 (18)	C4—C5	1.510 (4)
Sn1—O2ⁱ	2.359 (2)	C5—C6	1.507 (4)
O1—C4	1.261 (3)	C5—H5A	0.9700
O2—C4	1.245 (3)	C5—H5B	0.9700
O2—Sn1ⁱⁱ	2.359 (2)	C6—C7	1.383 (4)
O3—N1	1.219 (4)	C6—C11	1.393 (4)
O4—N1	1.218 (4)	C7—C8	1.376 (4)
N1—C11	1.465 (4)	C7—H7	0.9300
C1—H1A	0.9600	C8—C9	1.367 (5)
C1—H1B	0.9600	C8—H8	0.9300
C1—H1C	0.9600	C9—C10	1.366 (5)
C2—H2A	0.9600	C9—H9	0.9300
C2—H2B	0.9600	C10—C11	1.375 (4)
C2—H2C	0.9600	C10—H10	0.9300

C3—Sn1—C2	117.01 (14)	Sn1—C3—H3C	109.5
C3—Sn1—C1	122.46 (14)	H3A—C3—H3C	109.5
C2—Sn1—C1	119.75 (13)	H3B—C3—H3C	109.5
C3—Sn1—O1	94.58 (11)	O2—C4—O1	122.8 (3)
C2—Sn1—O1	88.20 (10)	O2—C4—C5	119.7 (3)
C1—Sn1—O1	95.78 (10)	O1—C4—C5	117.5 (2)
C3—Sn1—O2ⁱ	85.57 (12)	C6—C5—C4	116.3 (2)
C2—Sn1—O2ⁱ	84.62 (10)	C6—C5—H5A	108.2
C1—Sn1—O2ⁱ	90.86 (10)	C4—C5—H5A	108.2
O1—Sn1—O2ⁱ	172.00 (7)	C6—C5—H5B	108.2
C4—O1—Sn1	120.00 (17)	C4—C5—H5B	108.2
C4—O2—Sn1ⁱⁱ	143.50 (19)	H5A—C5—H5B	107.4
O4—N1—O3	123.7 (3)	C7—C6—C11	115.7 (3)
O4—N1—C11	118.1 (3)	C7—C6—C5	119.8 (3)
O3—N1—C11	118.2 (3)	C11—C6—C5	124.4 (3)
Sn1—C1—H1A	109.5	C8—C7—C6	122.3 (3)
Sn1—C1—H1B	109.5	C8—C7—H7	118.9
H1A—C1—H1B	109.5	C6—C7—H7	118.9
Sn1—C1—H1C	109.5	C9—C8—C7	120.2 (3)
H1A—C1—H1C	109.5	C9—C8—H8	119.9
H1B—C1—H1C	109.5	C7—C8—H8	119.9
Sn1—C2—H2A	109.5	C10—C9—C8	119.6 (3)
Sn1—C2—H2B	109.5	C10—C9—H9	120.2
H2A—C2—H2B	109.5	C8—C9—H9	120.2
Sn1—C2—H2C	109.5	C9—C10—C11	119.7 (3)
H2A—C2—H2C	109.5	C9—C10—H10	120.1
H2B—C2—H2C	109.5	C11—C10—H10	120.1
Sn1—C3—H3A	109.5	C10—C11—C6	122.5 (3)
Sn1—C3—H3B	109.5	C10—C11—N1	116.6 (3)
H3A—C3—H3B	109.5	C6—C11—N1	120.9 (3)

Sn1ⁱⁱ—O2—C4—O1	156.5 (2)	C8—C9—C10—C11	1.3 (6)
Sn1ⁱⁱ—O2—C4—C5	−24.2 (5)	C9—C10—C11—C6	−1.8 (5)
Sn1—O1—C4—O2	6.9 (4)	C9—C10—C11—N1	178.8 (3)
Sn1—O1—C4—C5	−172.5 (2)	C7—C6—C11—C10	0.8 (4)
O2—C4—C5—C6	−167.8 (3)	C5—C6—C11—C10	−178.2 (3)
O1—C4—C5—C6	11.6 (4)	C7—C6—C11—N1	−179.7 (3)
C4—C5—C6—C7	−127.1 (3)	C5—C6—C11—N1	1.2 (4)
C4—C5—C6—C11	51.9 (4)	O4—N1—C11—C10	−143.4 (3)
C11—C6—C7—C8	0.5 (4)	O3—N1—C11—C10	36.1 (4)
C5—C6—C7—C8	179.6 (3)	O4—N1—C11—C6	37.2 (4)
C6—C7—C8—C9	−1.0 (5)	O3—N1—C11—C6	−143.3 (3)
C7—C8—C9—C10	0.0 (5)

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2.

Selected bond lengths (Å) top

Sn1—C3	2.114 (3)	Sn1—O1	2.1970 (18)
Sn1—C2	2.120 (3)	Sn1—O2ⁱ	2.359 (2)
Sn1—C1	2.121 (3)

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

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