catena-Poly­[[tri­methyl­tin(IV)]-μ-(2,5-dioxo-2,5-di­hydro-1H-pyrrol-1-yl)-3-phenyl­propionato-κ²O:O′]

The mol­ecules of the title compound, [Sn(CH₃)₃(C₁₃H₁₀NO₄)], form polymeric chains involving both O atoms of the acid moiety. The geometry around the Sn atom is distorted trigonal bipyramidal, whith three methyl C atoms occupying the equatorial positions and O atoms from two symmetry-related mol­ecules at axial positions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.023
• wR factor = 0.060
• Data-to-parameter ratio = 23.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.94

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.88 Ratio
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      31.00 A   3  

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.00
           From the CIF: _reflns_number_total               4688
           Count of symmetry unique reflns         3016
           Completeness (_total/calc)            155.44%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1672
           Fraction of Friedel pairs measured     0.554
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

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Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

catena-Poly[[trimethyltin(IV)]-µ-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)- 3-phenylpropionato-κ²O:O']

Crystal data

[Sn(CH3)3(C13H10NO4)]	F(000) = 816
Mr = 408.01	Dx = 1.504 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4688 reflections
a = 6.492 (1) Å	θ = 3.5–30.0°
b = 9.857 (2) Å	µ = 1.43 mm^−1
c = 28.154 (6) Å	T = 173 K
V = 1801.6 (6) Å^3	Block, colorless
Z = 4	0.16 × 0.12 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	4688 independent reflections
Radiation source: fine-focus sealed tube	4553 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.00
ω and φ scans	θmax = 30.0°, θmin = 3.5°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −8→9
Tmin = 0.803, Tmax = 0.894	k = −13→13
4688 measured reflections	l = −39→39

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.023	w = 1/[σ^2(Fo^2) + 0.58P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.060	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.34 e Å^−3
4688 reflections	Δρmin = −0.41 e Å^−3
200 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0084 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1841 Friedels
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.01 (2)

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

	x	y	z	Uiso*/Ueq
Sn1	0.42149 (2)	0.321170 (15)	0.769873 (5)	0.02156 (6)
O1	0.3375 (3)	0.18160 (18)	0.82535 (6)	0.0309 (4)
O2	0.4675 (3)	0.00183 (18)	0.78748 (6)	0.0266 (4)
O3	0.4216 (3)	0.1307 (2)	0.95182 (7)	0.0445 (5)
O4	−0.1017 (3)	0.0149 (2)	0.85278 (8)	0.0516 (6)
N1	0.1931 (3)	0.0408 (2)	0.89766 (6)	0.0217 (4)
C1	0.2645 (5)	0.4790 (3)	0.80569 (10)	0.0364 (6)
H1A	0.3531	0.5159	0.8308	0.055*
H1B	0.1378	0.4432	0.8198	0.055*
H1C	0.2300	0.5511	0.7831	0.055*
C2	0.7420 (4)	0.3028 (3)	0.78196 (10)	0.0338 (6)
H2A	0.7962	0.2265	0.7635	0.051*
H2B	0.7671	0.2868	0.8158	0.051*
H2C	0.8112	0.3866	0.7722	0.051*
C3	0.2573 (4)	0.2265 (3)	0.71381 (9)	0.0305 (5)
H3A	0.3428	0.1552	0.6997	0.046*
H3B	0.2230	0.2941	0.6896	0.046*
H3C	0.1302	0.1864	0.7263	0.046*
C4	0.3855 (3)	0.0561 (2)	0.82228 (7)	0.0232 (4)
C5	0.3424 (4)	−0.0278 (2)	0.86735 (7)	0.0229 (4)
H5	0.4744	−0.0310	0.8856	0.027*
C6	0.2830 (4)	−0.1753 (3)	0.85694 (8)	0.0300 (5)
H6A	0.1512	−0.1763	0.8393	0.036*
H6B	0.3896	−0.2162	0.8363	0.036*
C7	0.2603 (5)	−0.2613 (2)	0.90111 (8)	0.0307 (5)
C8	0.0749 (5)	−0.3209 (3)	0.91215 (11)	0.0482 (7)
H8	−0.0412	−0.3056	0.8923	0.058*
C9	0.0550 (7)	−0.4036 (4)	0.95202 (14)	0.0659 (11)
H9	−0.0742	−0.4438	0.9592	0.079*
C10	0.2210 (7)	−0.4272 (4)	0.98079 (12)	0.0583 (10)
H10	0.2076	−0.4841	1.0078	0.070*
C11	0.4042 (7)	−0.3690 (4)	0.97054 (14)	0.0649 (11)
H11	0.5193	−0.3850	0.9906	0.078*
C12	0.4259 (5)	−0.2860 (4)	0.93100 (12)	0.0521 (8)
H12	0.5557	−0.2457	0.9243	0.062*
C13	0.2491 (4)	0.1227 (3)	0.93545 (8)	0.0289 (5)
C14	0.0600 (5)	0.1966 (3)	0.95058 (10)	0.0432 (7)
H14	0.0499	0.2572	0.9767	0.052*
C15	−0.0895 (4)	0.1638 (3)	0.92174 (10)	0.0419 (6)
H15	−0.2264	0.1975	0.9234	0.050*
C16	−0.0118 (4)	0.0652 (3)	0.88583 (10)	0.0305 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.02443 (9)	0.01644 (8)	0.02381 (8)	0.00004 (6)	0.00359 (6)	−0.00039 (5)
O1	0.0477 (10)	0.0160 (7)	0.0291 (8)	−0.0010 (8)	0.0132 (7)	0.0023 (7)
O2	0.0370 (9)	0.0208 (8)	0.0219 (7)	0.0015 (7)	0.0063 (7)	−0.0020 (6)
O3	0.0420 (10)	0.0518 (13)	0.0395 (10)	0.0019 (11)	−0.0133 (10)	−0.0180 (9)
O4	0.0413 (11)	0.0491 (13)	0.0643 (13)	0.0046 (11)	−0.0234 (11)	−0.0136 (11)
N1	0.0235 (9)	0.0215 (9)	0.0200 (8)	−0.0002 (8)	0.0024 (7)	−0.0011 (7)
C1	0.0397 (14)	0.0202 (12)	0.0494 (15)	0.0004 (11)	0.0152 (13)	−0.0057 (11)
C2	0.0257 (11)	0.0330 (14)	0.0427 (14)	−0.0006 (11)	−0.0035 (10)	0.0004 (10)
C3	0.0292 (12)	0.0270 (11)	0.0352 (11)	−0.0045 (10)	−0.0060 (10)	−0.0005 (9)
C4	0.0285 (11)	0.0206 (10)	0.0204 (9)	−0.0029 (9)	0.0020 (8)	−0.0010 (7)
C5	0.0307 (11)	0.0189 (10)	0.0191 (9)	0.0003 (9)	0.0016 (8)	−0.0016 (8)
C6	0.0438 (13)	0.0205 (11)	0.0256 (10)	−0.0040 (12)	0.0039 (9)	−0.0013 (9)
C7	0.0450 (14)	0.0189 (11)	0.0282 (11)	−0.0010 (11)	0.0062 (11)	0.0015 (8)
C8	0.0419 (15)	0.0505 (18)	0.0523 (16)	0.000 (2)	0.0083 (14)	0.0196 (15)
C9	0.057 (2)	0.068 (3)	0.073 (2)	−0.004 (2)	0.021 (2)	0.034 (2)
C10	0.078 (2)	0.050 (2)	0.0472 (17)	0.001 (2)	0.0102 (19)	0.0264 (15)
C11	0.066 (2)	0.067 (2)	0.062 (2)	0.004 (2)	−0.009 (2)	0.0345 (19)
C12	0.0427 (16)	0.053 (2)	0.0603 (18)	−0.0048 (16)	−0.0020 (16)	0.0244 (15)
C13	0.0364 (13)	0.0282 (12)	0.0221 (10)	0.0002 (11)	0.0010 (10)	−0.0044 (9)
C14	0.0474 (16)	0.0449 (17)	0.0373 (13)	0.0065 (16)	0.0122 (12)	−0.0137 (12)
C15	0.0317 (12)	0.0447 (17)	0.0494 (15)	0.0074 (16)	0.0114 (13)	−0.0034 (13)
C16	0.0266 (11)	0.0269 (13)	0.0381 (13)	−0.0013 (10)	−0.0019 (10)	0.0004 (10)

Geometric parameters (Å, º)

Sn1—C2	2.116 (3)	C4—C5	1.540 (3)
Sn1—C1	2.116 (3)	C5—C6	1.532 (3)
Sn1—C3	2.121 (2)	C5—H5	1.0000
Sn1—O1	2.1517 (17)	C6—C7	1.512 (3)
Sn1—O2^i	2.5094 (17)	C6—H6A	0.9900
O1—C4	1.278 (3)	C6—H6B	0.9900
O2—C4	1.237 (3)	C7—C8	1.375 (4)
O2—Sn1^ii	2.5095 (17)	C7—C12	1.387 (4)
O3—C13	1.213 (3)	C8—C9	1.393 (4)
O4—C16	1.205 (3)	C8—H8	0.9500
N1—C13	1.385 (3)	C9—C10	1.368 (5)
N1—C16	1.392 (3)	C9—H9	0.9500
N1—C5	1.458 (3)	C10—C11	1.352 (6)
C1—H1A	0.9800	C10—H10	0.9500
C1—H1B	0.9800	C11—C12	1.389 (4)
C1—H1C	0.9800	C11—H11	0.9500
C2—H2A	0.9800	C12—H12	0.9500
C2—H2B	0.9800	C13—C14	1.489 (4)
C2—H2C	0.9800	C14—C15	1.306 (4)
C3—H3A	0.9800	C14—H14	0.9500
C3—H3B	0.9800	C15—C16	1.490 (4)
C3—H3C	0.9800	C15—H15	0.9500
C2—Sn1—C1	117.38 (12)	N1—C5—H5	106.5
C2—Sn1—C3	125.18 (11)	C6—C5—H5	106.5
C1—Sn1—C3	115.86 (11)	C4—C5—H5	106.5
C2—Sn1—O1	94.46 (9)	C7—C6—C5	113.53 (19)
C1—Sn1—O1	90.12 (9)	C7—C6—H6A	108.9
C3—Sn1—O1	97.56 (9)	C5—C6—H6A	108.9
C2—Sn1—O2^i	83.21 (9)	C7—C6—H6B	108.9
C1—Sn1—O2^i	85.59 (9)	C5—C6—H6B	108.9
C3—Sn1—O2^i	88.73 (8)	H6A—C6—H6B	107.7
O1—Sn1—O2^i	173.49 (6)	C8—C7—C12	117.8 (2)
C4—O1—Sn1	120.51 (14)	C8—C7—C6	120.7 (3)
C4—O2—Sn1^ii	160.11 (16)	C12—C7—C6	121.4 (3)
C13—N1—C16	109.5 (2)	C7—C8—C9	120.9 (3)
C13—N1—C5	123.1 (2)	C7—C8—H8	119.6
C16—N1—C5	125.1 (2)	C9—C8—H8	119.6
Sn1—C1—H1A	109.5	C10—C9—C8	120.2 (3)
Sn1—C1—H1B	109.5	C10—C9—H9	119.9
H1A—C1—H1B	109.5	C8—C9—H9	119.9
Sn1—C1—H1C	109.5	C11—C10—C9	119.6 (3)
H1A—C1—H1C	109.5	C11—C10—H10	120.2
H1B—C1—H1C	109.5	C9—C10—H10	120.2
Sn1—C2—H2A	109.5	C10—C11—C12	120.7 (3)
Sn1—C2—H2B	109.5	C10—C11—H11	119.7
H2A—C2—H2B	109.5	C12—C11—H11	119.6
Sn1—C2—H2C	109.5	C7—C12—C11	120.7 (3)
H2A—C2—H2C	109.5	C7—C12—H12	119.6
H2B—C2—H2C	109.5	C11—C12—H12	119.6
Sn1—C3—H3A	109.5	O3—C13—N1	124.9 (2)
Sn1—C3—H3B	109.5	O3—C13—C14	128.3 (2)
H3A—C3—H3B	109.5	N1—C13—C14	106.8 (2)
Sn1—C3—H3C	109.5	C15—C14—C13	108.3 (2)
H3A—C3—H3C	109.5	C15—C14—H14	125.9
H3B—C3—H3C	109.5	C13—C14—H14	125.9
O2—C4—O1	125.3 (2)	C14—C15—C16	109.4 (2)
O2—C4—C5	119.9 (2)	C14—C15—H15	125.3
O1—C4—C5	114.79 (18)	C16—C15—H15	125.3
N1—C5—C6	112.6 (2)	O4—C16—N1	125.2 (3)
N1—C5—C4	110.74 (19)	O4—C16—C15	128.9 (3)
C6—C5—C4	113.43 (18)	N1—C16—C15	105.9 (2)
C2—Sn1—O1—C4	−65.87 (19)	C6—C7—C8—C9	178.0 (3)
C1—Sn1—O1—C4	176.64 (19)	C7—C8—C9—C10	−0.3 (6)
C3—Sn1—O1—C4	60.52 (19)	C8—C9—C10—C11	0.5 (7)
Sn1^ii—O2—C4—O1	−157.8 (3)	C9—C10—C11—C12	−0.3 (7)
Sn1^ii—O2—C4—C5	24.9 (6)	C8—C7—C12—C11	0.3 (5)
Sn1—O1—C4—O2	−5.4 (3)	C6—C7—C12—C11	−177.8 (3)
Sn1—O1—C4—C5	171.99 (14)	C10—C11—C12—C7	−0.1 (6)
C13—N1—C5—C6	136.0 (2)	C16—N1—C13—O3	−175.1 (3)
C16—N1—C5—C6	−62.9 (3)	C5—N1—C13—O3	−11.5 (4)
C13—N1—C5—C4	−95.8 (3)	C16—N1—C13—C14	4.4 (3)
C16—N1—C5—C4	65.3 (3)	C5—N1—C13—C14	168.0 (2)
O2—C4—C5—N1	−162.7 (2)	O3—C13—C14—C15	176.4 (3)
O1—C4—C5—N1	19.8 (3)	N1—C13—C14—C15	−3.0 (3)
O2—C4—C5—C6	−34.9 (3)	C13—C14—C15—C16	0.6 (4)
O1—C4—C5—C6	147.5 (2)	C13—N1—C16—O4	175.8 (3)
N1—C5—C6—C7	−58.7 (3)	C5—N1—C16—O4	12.6 (4)
C4—C5—C6—C7	174.5 (2)	C13—N1—C16—C15	−4.0 (3)
C5—C6—C7—C8	118.7 (3)	C5—N1—C16—C15	−167.2 (2)
C5—C6—C7—C12	−63.2 (4)	C14—C15—C16—O4	−177.7 (3)
C12—C7—C8—C9	−0.1 (5)	C14—C15—C16—N1	2.1 (3)

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