Dimeth­yl(1,10-phenanthroline)(pyridine-2,6-dicarboxyl­ato)tin(IV)

The mol­ecule of the title compound, [Sn(C₉H₃NO₄)(CH₃)₂(C₁₂H₈N₂)], occupies a special position on a mirror plane, which passes through the Sn, pyridine N and para-C, and two methyl C atoms. The Sn atom has a distorted penta­gonal-bipyramidal coordination, with the equatorial plane formed by two N atoms of 1,10-phenanthroline [Sn-N = 2.4754 (18) Å], and the pyridine N and two carboxyl­ate O atoms of pyridine-2,6-dicarboxyl­ate [Sn-N = 2.288 (2) Å and Sn-O = 2.2614 (15) Å]; two methyl groups occupy the axial positions [Sn-C = 2.112 (3) and 2.096 (4) Å, and C-Sn-C = 174.26 (13)°].

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.025
• wR factor = 0.059
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

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PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...          4

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

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

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Dimethyl(1,10-phenanthroline)(pyridine-2,6-dicarboxylato)tin

Crystal data

[Sn(C9H3NO4)(CH3)2(C12H8N2)]	F(000) = 492
Mr = 494.07	Dx = 1.739 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
a = 7.4595 (8) Å	Cell parameters from 4502 reflections
b = 13.754 (1) Å	θ = 2.2–25.2°
c = 9.723 (1) Å	µ = 1.39 mm^−1
β = 108.914 (1)°	T = 295 K
V = 943.75 (17) Å^3	Plate, colorless
Z = 2	0.16 × 0.14 × 0.03 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2257 independent reflections
Radiation source: fine-focus sealed tube	2099 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.808, Tmax = 0.959	k = −17→17
10848 measured reflections	l = −12→12

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) = 0.059	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0339P)^2] where P = (Fo^2 + 2Fc^2)/3
2257 reflections	(Δ/σ)max < 0.001
153 parameters	Δρmax = 0.46 e Å^−3
10 restraints	Δρmin = −0.44 e Å^−3

Special details

Experimental. The elemental analyses were performed with a Perkin–Elmer PE2400II instrument.

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	0.19651 (3)	0.2500	0.104475 (19)	0.03814 (9)
O1	0.1735 (2)	0.09596 (11)	0.17834 (17)	0.0523 (4)
O2	0.1513 (3)	−0.00151 (13)	0.3546 (2)	0.0693 (5)
N1	0.2786 (2)	0.15089 (14)	−0.07911 (19)	0.0443 (4)
N2	0.1119 (3)	0.2500	0.3106 (3)	0.0393 (5)
C1	0.4889 (5)	0.2500	0.2235 (4)	0.0457 (7)
H1A	0.564 (4)	0.2500	0.160 (3)	0.053 (10)*
H1B	0.516 (4)	0.1931 (7)	0.283 (2)	0.076 (9)*
C2	−0.0859 (5)	0.2500	−0.0326 (4)	0.0651 (10)
H2A	−0.179 (6)	0.2500	0.017 (5)	0.121 (19)*
H2B	−0.102 (4)	0.1932 (7)	−0.093 (3)	0.092 (10)*
C3	0.1390 (3)	0.07780 (17)	0.2958 (3)	0.0481 (5)
C4	0.0829 (3)	0.16528 (16)	0.3665 (2)	0.0419 (5)
C5	0.0103 (3)	0.16280 (18)	0.4807 (2)	0.0482 (5)
H5	−0.0122	0.1040	0.5194	0.058*
C6	−0.0277 (4)	0.2500	0.5353 (3)	0.0510 (8)
H6	−0.0797	0.2500	0.6103	0.061*
C7	0.2622 (4)	0.05562 (19)	−0.0889 (3)	0.0534 (6)
H7	0.2017	0.0237	−0.0320	0.064*
C8	0.3319 (4)	0.0005 (2)	−0.1813 (3)	0.0621 (7)
H8	0.3166	−0.0667	−0.1862	0.074*
C9	0.4225 (3)	0.0462 (2)	−0.2641 (3)	0.0617 (7)
H9	0.4734	0.0101	−0.3234	0.074*
C10	0.4387 (3)	0.1475 (2)	−0.2597 (2)	0.0531 (6)
C11	0.3616 (3)	0.19811 (17)	−0.1666 (2)	0.0441 (5)
C12	0.5212 (3)	0.2012 (2)	−0.3495 (3)	0.0647 (7)
H12	0.5759	0.1680	−0.4092	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.04170 (13)	0.04257 (13)	0.03360 (12)	0.000	0.01695 (9)	0.000
O1	0.0729 (11)	0.0451 (8)	0.0507 (9)	−0.0053 (7)	0.0364 (8)	−0.0024 (7)
O2	0.0933 (14)	0.0509 (10)	0.0828 (13)	0.0050 (9)	0.0548 (12)	0.0158 (9)
N1	0.0492 (10)	0.0493 (11)	0.0367 (9)	0.0009 (8)	0.0171 (8)	−0.0049 (8)
N2	0.0391 (13)	0.0461 (14)	0.0360 (12)	0.000	0.0171 (10)	0.000
C1	0.0446 (17)	0.0476 (18)	0.0449 (17)	0.000	0.0143 (14)	0.000
C2	0.0450 (19)	0.096 (3)	0.052 (2)	0.000	0.0117 (17)	0.000
C3	0.0471 (12)	0.0502 (13)	0.0530 (13)	−0.0049 (10)	0.0246 (10)	0.0030 (10)
C4	0.0377 (10)	0.0525 (12)	0.0375 (10)	−0.0018 (9)	0.0151 (9)	0.0033 (9)
C5	0.0433 (12)	0.0635 (14)	0.0420 (12)	−0.0042 (10)	0.0194 (10)	0.0060 (10)
C6	0.0425 (17)	0.076 (2)	0.0411 (17)	0.000	0.0225 (14)	0.000
C7	0.0605 (14)	0.0531 (14)	0.0479 (13)	−0.0021 (11)	0.0193 (11)	−0.0090 (10)
C8	0.0652 (16)	0.0621 (15)	0.0561 (15)	0.0070 (12)	0.0157 (13)	−0.0165 (12)
C9	0.0572 (14)	0.0843 (19)	0.0436 (13)	0.0164 (13)	0.0160 (11)	−0.0155 (12)
C10	0.0397 (11)	0.0818 (17)	0.0365 (11)	0.0086 (11)	0.0104 (9)	−0.0068 (11)
C11	0.0364 (10)	0.0653 (13)	0.0302 (10)	0.0009 (9)	0.0101 (8)	−0.0031 (9)
C12	0.0474 (13)	0.110 (2)	0.0413 (12)	0.0035 (12)	0.0210 (10)	−0.0064 (12)

Geometric parameters (Å, º)

Sn1—C2	2.096 (4)	C3—C4	1.511 (3)
Sn1—C1	2.112 (3)	C4—C5	1.385 (3)
Sn1—O1	2.2614 (15)	C5—C6	1.378 (3)
Sn1—O1^i	2.2614 (15)	C5—H5	0.9300
Sn1—N2	2.288 (2)	C6—C5^i	1.378 (3)
Sn1—N1	2.4754 (18)	C6—H6	0.9300
Sn1—N1^i	2.4754 (18)	C7—C8	1.399 (4)
O1—C3	1.274 (3)	C7—H7	0.9300
O2—C3	1.221 (3)	C8—C9	1.360 (4)
N1—C7	1.317 (3)	C8—H8	0.9300
N1—C11	1.367 (3)	C9—C10	1.398 (4)
N2—C4	1.333 (2)	C9—H9	0.9300
N2—C4^i	1.333 (2)	C10—C11	1.405 (3)
C1—H1A	0.959 (16)	C10—C12	1.427 (4)
C1—H1B	0.957 (12)	C11—C11^i	1.428 (5)
C2—H2A	0.97 (5)	C12—C12^i	1.342 (6)
C2—H2B	0.962 (13)	C12—H12	0.9300
C2—Sn1—C1	174.26 (13)	Sn1—C2—H2B	106.8 (18)
C2—Sn1—O1	92.17 (6)	H2A—C2—H2B	109.8 (17)
C1—Sn1—O1	89.83 (5)	O2—C3—O1	126.0 (2)
C2—Sn1—O1^i	92.17 (6)	O2—C3—C4	119.2 (2)
C1—Sn1—O1^i	89.83 (5)	O1—C3—C4	114.73 (19)
O1—Sn1—O1^i	139.08 (8)	N2—C4—C5	120.4 (2)
C2—Sn1—N2	92.93 (12)	N2—C4—C3	113.88 (18)
C1—Sn1—N2	92.81 (11)	C5—C4—C3	125.7 (2)
O1—Sn1—N2	69.57 (4)	C6—C5—C4	118.1 (2)
O1^i—Sn1—N2	69.57 (4)	C6—C5—H5	121.0
C2—Sn1—N1	88.50 (10)	C4—C5—H5	121.0
C1—Sn1—N1	86.71 (9)	C5—C6—C5^i	121.0 (3)
O1—Sn1—N1	77.00 (6)	C5—C6—H6	119.5
O1^i—Sn1—N1	143.79 (6)	C5^i—C6—H6	119.5
N2—Sn1—N1	146.57 (5)	N1—C7—C8	122.7 (3)
C2—Sn1—N1^i	88.50 (10)	N1—C7—H7	118.6
C1—Sn1—N1^i	86.71 (9)	C8—C7—H7	118.6
O1—Sn1—N1^i	143.79 (6)	C9—C8—C7	119.3 (3)
O1^i—Sn1—N1^i	77.00 (6)	C9—C8—H8	120.4
N2—Sn1—N1^i	146.57 (5)	C7—C8—H8	120.4
N1—Sn1—N1^i	66.83 (9)	C8—C9—C10	119.8 (2)
C3—O1—Sn1	121.77 (14)	C8—C9—H9	120.1
C7—N1—C11	118.6 (2)	C10—C9—H9	120.1
C7—N1—Sn1	124.14 (16)	C9—C10—C11	117.7 (2)
C11—N1—Sn1	117.04 (15)	C9—C10—C12	123.2 (2)
C4—N2—C4^i	121.9 (2)	C11—C10—C12	119.0 (3)
C4—N2—Sn1	119.00 (12)	N1—C11—C10	121.9 (2)
C4^i—N2—Sn1	119.00 (12)	N1—C11—C11^i	118.36 (13)
Sn1—C1—H1A	111 (2)	C10—C11—C11^i	119.73 (16)
Sn1—C1—H1B	107.9 (16)	C12^i—C12—C10	121.22 (16)
H1A—C1—H1B	110.0 (14)	C12^i—C12—H12	119.4
Sn1—C2—H2A	115 (3)	C10—C12—H12	119.4
C2—Sn1—O1—C3	−96.5 (2)	Sn1—O1—C3—O2	−168.6 (2)
C1—Sn1—O1—C3	88.88 (19)	Sn1—O1—C3—C4	9.8 (3)
O1^i—Sn1—O1—C3	−0.7 (3)	C4^i—N2—C4—C5	3.8 (4)
N2—Sn1—O1—C3	−4.18 (17)	Sn1—N2—C4—C5	−172.42 (15)
N1—Sn1—O1—C3	175.54 (18)	C4^i—N2—C4—C3	−175.22 (17)
N1^i—Sn1—O1—C3	173.06 (15)	Sn1—N2—C4—C3	8.5 (3)
C2—Sn1—N1—C7	−84.32 (19)	O2—C3—C4—N2	166.8 (2)
C1—Sn1—N1—C7	98.85 (19)	O1—C3—C4—N2	−11.7 (3)
O1—Sn1—N1—C7	8.26 (18)	O2—C3—C4—C5	−12.2 (4)
O1^i—Sn1—N1—C7	−175.96 (16)	O1—C3—C4—C5	169.3 (2)
N2—Sn1—N1—C7	8.7 (2)	N2—C4—C5—C6	−1.0 (3)
N1^i—Sn1—N1—C7	−173.33 (16)	C3—C4—C5—C6	177.9 (2)
C2—Sn1—N1—C11	101.72 (16)	C4—C5—C6—C5^i	−1.8 (5)
C1—Sn1—N1—C11	−75.11 (15)	C11—N1—C7—C8	2.3 (3)
O1—Sn1—N1—C11	−165.70 (16)	Sn1—N1—C7—C8	−171.62 (18)
O1^i—Sn1—N1—C11	10.1 (2)	N1—C7—C8—C9	0.7 (4)
N2—Sn1—N1—C11	−165.22 (15)	C7—C8—C9—C10	−2.3 (4)
N1^i—Sn1—N1—C11	12.71 (17)	C8—C9—C10—C11	0.9 (4)
C2—Sn1—N2—C4	88.17 (18)	C8—C9—C10—C12	−176.1 (2)
C1—Sn1—N2—C4	−91.83 (18)	C7—N1—C11—C10	−3.6 (3)
O1—Sn1—N2—C4	−3.06 (17)	Sn1—N1—C11—C10	170.66 (15)
O1^i—Sn1—N2—C4	179.4 (2)	C7—N1—C11—C11^i	173.64 (15)
N1—Sn1—N2—C4	−3.6 (3)	Sn1—N1—C11—C11^i	−12.05 (15)
N1^i—Sn1—N2—C4	179.90 (13)	C9—C10—C11—N1	2.1 (3)
C2—Sn1—N2—C4^i	−88.17 (18)	C12—C10—C11—N1	179.2 (2)
C1—Sn1—N2—C4^i	91.83 (18)	C9—C10—C11—C11^i	−175.17 (15)
O1—Sn1—N2—C4^i	−179.4 (2)	C12—C10—C11—C11^i	1.9 (2)
O1^i—Sn1—N2—C4^i	3.06 (17)	C9—C10—C12—C12^i	174.97 (17)
N1—Sn1—N2—C4^i	−179.90 (13)	C11—C10—C12—C12^i	−2.0 (2)
N1^i—Sn1—N2—C4^i	3.6 (3)

Symmetry code: (i) x, −y+1/2, z.