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

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.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.025
• wR factor = 0.057
• Data-to-parameter ratio = 19.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....        Sn1 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1 Note

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          1 Info
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units

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

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

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S1. Comment

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

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).

S2. Experimental

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.

S3. Refinement

The H atoms were positioned geometrically (C—H = 0.93—0.97 Å) and refined as riding with U_iso(H) = xU_eq(C), where x = 1.5 for methyl and x = 1.2 for other H-atoms.

Computing details

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

	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']

Crystal data

[Sn(CH3)3(C8H6NO4)]	F(000) = 1360
Mr = 343.93	Dx = 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) Å^3	Prism, white
Z = 8	0.40 × 0.32 × 0.28 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	3074 independent reflections
Radiation source: fine-focus sealed tube	2734 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 7.80 pixels mm^-1	θmax = 27.0°, θmin = 1.8°
ω scans	h = −16→15
Absorption correction: multi-scan SADABS (Bruker, 2005)	k = −12→12
Tmin = 0.532, Tmax = 0.631	l = −29→29
11546 measured reflections

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.057	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0174P)^2 + 4.9157P] where P = (Fo^2 + 2Fc^2)/3
3070 reflections	(Δ/σ)max = 0.002
157 parameters	Δρmax = 0.74 e Å^−3
0 restraints	Δρmin = −0.53 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

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

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—O2^i	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—Sn1^ii	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—O2^i	85.57 (12)	C6—C5—C4	116.3 (2)
C2—Sn1—O2^i	84.62 (10)	C6—C5—H5A	108.2
C1—Sn1—O2^i	90.86 (10)	C4—C5—H5A	108.2
O1—Sn1—O2^i	172.00 (7)	C6—C5—H5B	108.2
C4—O1—Sn1	120.00 (17)	C4—C5—H5B	108.2
C4—O2—Sn1^ii	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)
Sn1^ii—O2—C4—O1	156.5 (2)	C8—C9—C10—C11	1.3 (6)
Sn1^ii—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.