Bis(μ-pyridine-2,6-dicarboxyl­ato)-κ⁴O,N,O′:O′;κ⁴O:O,N,O′-bis[aqua­methyl­phen­yltin(IV)] chloro­form disolvate

The dinuclear title compound, [Sn₂(CH₃)₂(C₆H₅)₂(C₇H₃NO₄)₂(H₂O)₂]·2CHCl₃, crystallizes as a dichloro­form solvate; the centrosymmetric compound has Sn in a seven-coordinate, trans-penta­gonal–bipyramidal geometry. The dicarboxyl­ate unit is tetra­dentate; it binds through the N and the two O atoms (one from the dianion); one of the O atoms that is involved in coordination forms a bridge to the other Sn atom.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.007 Å
• H-atom completeness 94%
• R factor = 0.046
• wR factor = 0.132
• Data-to-parameter ratio = 23.1

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.499     0.964
            Tmin(prime) and Tmax expected:      0.570     0.964
            RR(prime) =      0.876
            Please check that your absorption correction is appropriate.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.86
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C15
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C30 H30 Cl6 N2 O10 Sn2
            Atom count from the _atom_site data:  C30 H28 Cl6 N2 O10 Sn2
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C30 H30 Cl6 N2 O10 Sn2
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        120.00    120.00    0.00
           H        120.00    112.00    8.00
           Cl        24.00     24.00    0.00
           N          8.00      8.00    0.00
           O         40.00     40.00    0.00
           Sn         8.00      8.00    0.00

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

   5 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
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX-II software (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

Bis[aquamethylphenyl(µ-pyridine-2,6-dicarboxylato-κ⁴O,N,O':O'')tin(IV)] chloroform disolvate

Crystal data

[Sn2(CH3)2(C6H5)2(C7H3NO4)2(H2O)2]·2CHCl3	F(000) = 2024
Mr = 1028.64	Dx = 1.851 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8494 reflections
a = 22.7306 (3) Å	θ = 2.5–32.4°
b = 10.6253 (2) Å	µ = 1.84 mm^−1
c = 17.1579 (3) Å	T = 173 K
β = 117.028 (1)°	Plate, colorless
V = 3691.4 (1) Å^3	0.30 × 0.18 × 0.02 mm
Z = 4

Data collection

Bruker APEX-II diffractometer	5278 independent reflections
Radiation source: medium-focus sealed tube	3763 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
φ and ω scans	θmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→31
Tmin = 0.499, Tmax = 0.964	k = −14→14
17272 measured reflections	l = −21→24

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0696P)^2 + 5.0368P] where P = (Fo^2 + 2Fc^2)/3
5278 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 1.90 e Å^−3
18 restraints	Δρmin = −1.87 e Å^−3

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

	x	y	z	Uiso*/Ueq
Sn1	0.409535 (14)	0.46852 (3)	0.39391 (2)	0.01197 (10)
Cl1	0.70349 (9)	0.0009 (3)	0.86528 (18)	0.0937 (11)
Cl2	0.57639 (10)	−0.08996 (18)	0.74369 (14)	0.0533 (5)
Cl3	0.58658 (12)	0.15302 (19)	0.82199 (13)	0.0599 (5)
O1w	0.37540 (15)	0.6425 (3)	0.3100 (2)	0.0162 (7)
H1w1	0.4025	0.7010	0.3338	0.024*
H1w2	0.3381	0.6640	0.3044	0.024*
O1	0.31310 (15)	0.4203 (3)	0.2870 (2)	0.0152 (6)
O2	0.23007 (16)	0.2842 (3)	0.2259 (2)	0.0210 (7)
O3	0.49671 (15)	0.3700 (3)	0.5217 (2)	0.0154 (6)
O4	0.53426 (16)	0.1900 (3)	0.5961 (2)	0.0217 (8)
N1	0.38628 (17)	0.2634 (4)	0.4086 (2)	0.0138 (8)
C1	0.4664 (2)	0.4262 (5)	0.3288 (3)	0.0197 (10)
H1a	0.4371	0.4048	0.2677	0.030*
H1b	0.4954	0.3546	0.3575	0.030*
H1c	0.4933	0.4995	0.3309	0.030*
C2	0.3729 (2)	0.5355 (4)	0.4802 (3)	0.0151 (8)
C3	0.3606 (3)	0.6632 (5)	0.4839 (4)	0.0232 (10)
H3	0.3695	0.7209	0.4483	0.028*
C4	0.3355 (3)	0.7071 (5)	0.5393 (4)	0.0304 (12)
H4	0.3268	0.7943	0.5403	0.036*
C5	0.3232 (3)	0.6259 (6)	0.5924 (4)	0.0300 (13)
H5	0.3061	0.6567	0.6299	0.036*
C6	0.3360 (3)	0.4987 (5)	0.5907 (4)	0.0277 (12)
H6	0.3277	0.4418	0.6273	0.033*
C7	0.3611 (2)	0.4544 (5)	0.5351 (3)	0.0222 (10)
H7	0.3703	0.3673	0.5348	0.027*
C8	0.2858 (2)	0.3139 (4)	0.2822 (3)	0.0150 (9)
C9	0.3279 (2)	0.2182 (4)	0.3504 (3)	0.0153 (9)
C10	0.3089 (2)	0.0948 (4)	0.3532 (3)	0.0176 (9)
H10	0.2671	0.0645	0.3113	0.021*
C11	0.3529 (2)	0.0167 (4)	0.4190 (3)	0.0199 (10)
H11	0.3412	−0.0681	0.4228	0.024*
C12	0.4149 (2)	0.0642 (4)	0.4800 (3)	0.0185 (10)
H12	0.4460	0.0122	0.5248	0.022*
C13	0.4287 (2)	0.1886 (4)	0.4724 (3)	0.0151 (9)
C14	0.4924 (2)	0.2531 (4)	0.5364 (3)	0.0145 (9)
C15	0.6265 (3)	0.0445 (6)	0.7850 (4)	0.0338 (13)
H15	0.6323	0.0843	0.7361	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.00812 (14)	0.01176 (15)	0.01533 (15)	0.00030 (11)	0.00471 (11)	−0.00010 (13)
Cl1	0.0227 (9)	0.146 (2)	0.0909 (18)	−0.0047 (11)	0.0071 (10)	0.0816 (18)
Cl2	0.0594 (11)	0.0372 (9)	0.0802 (14)	−0.0084 (8)	0.0464 (11)	−0.0053 (9)
Cl3	0.1001 (16)	0.0453 (11)	0.0553 (11)	−0.0027 (10)	0.0538 (12)	−0.0084 (9)
O1w	0.0106 (15)	0.0164 (16)	0.0191 (16)	−0.0010 (12)	0.0046 (13)	0.0006 (13)
O1	0.0109 (15)	0.0149 (15)	0.0171 (16)	−0.0002 (12)	0.0040 (13)	0.0016 (13)
O2	0.0123 (16)	0.0194 (18)	0.0234 (18)	−0.0009 (12)	0.0013 (14)	0.0020 (14)
O3	0.0123 (15)	0.0116 (15)	0.0194 (16)	−0.0010 (11)	0.0048 (13)	−0.0008 (13)
O4	0.0145 (16)	0.0155 (17)	0.0247 (18)	−0.0008 (12)	−0.0002 (15)	0.0023 (14)
N1	0.0083 (17)	0.0131 (18)	0.0167 (19)	0.0012 (13)	0.0029 (15)	−0.0011 (15)
C1	0.018 (2)	0.019 (2)	0.025 (2)	0.0006 (17)	0.012 (2)	−0.0013 (19)
C2	0.0101 (19)	0.016 (2)	0.016 (2)	−0.0004 (16)	0.0034 (17)	0.0017 (18)
C3	0.026 (3)	0.019 (2)	0.028 (3)	0.0041 (19)	0.016 (2)	0.002 (2)
C4	0.040 (3)	0.023 (3)	0.032 (3)	0.013 (2)	0.019 (3)	−0.002 (2)
C5	0.028 (3)	0.039 (3)	0.029 (3)	0.010 (2)	0.018 (2)	0.000 (2)
C6	0.026 (3)	0.033 (3)	0.027 (3)	0.001 (2)	0.015 (2)	0.003 (2)
C7	0.018 (2)	0.022 (3)	0.027 (3)	0.0020 (18)	0.010 (2)	0.003 (2)
C8	0.010 (2)	0.014 (2)	0.020 (2)	0.0009 (15)	0.0058 (18)	0.0010 (17)
C9	0.010 (2)	0.015 (2)	0.020 (2)	−0.0012 (15)	0.0061 (18)	−0.0025 (18)
C10	0.015 (2)	0.011 (2)	0.025 (2)	−0.0030 (16)	0.0067 (19)	−0.0042 (18)
C11	0.022 (2)	0.007 (2)	0.027 (3)	−0.0037 (17)	0.008 (2)	0.0016 (18)
C12	0.017 (2)	0.014 (2)	0.022 (2)	−0.0003 (16)	0.006 (2)	−0.0014 (17)
C13	0.011 (2)	0.015 (2)	0.018 (2)	0.0009 (15)	0.0051 (18)	0.0001 (17)
C14	0.013 (2)	0.012 (2)	0.019 (2)	−0.0022 (15)	0.0078 (18)	−0.0023 (17)
C15	0.027 (3)	0.038 (3)	0.038 (3)	0.002 (2)	0.017 (3)	0.011 (3)

Geometric parameters (Å, º)

Sn1—C1	2.106 (5)	C2—C7	1.389 (7)
Sn1—C2	2.125 (5)	C2—C3	1.392 (7)
Sn1—O1	2.186 (3)	C3—C4	1.392 (7)
Sn1—N1	2.283 (4)	C3—H3	0.9500
Sn1—O3	2.425 (3)	C4—C5	1.372 (8)
Sn1—O3^i	2.604 (3)	C4—H4	0.9500
Sn1—O1w	2.253 (3)	C5—C6	1.384 (8)
Cl1—C15	1.727 (6)	C5—H5	0.9500
Cl2—C15	1.763 (7)	C6—C7	1.399 (8)
Cl3—C15	1.755 (7)	C6—H6	0.9500
O1w—H1w1	0.8400	C7—H7	0.9500
O1w—H1w2	0.8400	C8—C9	1.516 (6)
O1—C8	1.274 (5)	C9—C10	1.388 (6)
O2—C8	1.236 (5)	C10—C11	1.391 (7)
O3—C14	1.280 (5)	C10—H10	0.9500
O4—C14	1.232 (5)	C11—C12	1.413 (7)
N1—C9	1.336 (5)	C11—H11	0.9500
N1—C13	1.342 (6)	C12—C13	1.378 (6)
C1—H1a	0.9800	C12—H12	0.9500
C1—H1b	0.9800	C13—C14	1.525 (6)
C1—H1C	0.9800	C15—H15	1.0000
C1—Sn1—C2	166.2 (2)	C4—C3—H3	119.7
C1—Sn1—N1	94.8 (2)	C5—C4—C3	120.8 (5)
C1—Sn1—O1	97.4 (2)	C5—C4—H4	119.6
C1—Sn1—O3^i	83.8 (2)	C3—C4—H4	119.6
C1—Sn1—O3	86.6 (2)	C4—C5—C6	119.5 (5)
C1—Sn1—O1w	87.3 (2)	C4—C5—H5	120.2
C2—Sn1—O3	86.1 (1)	C6—C5—H5	120.2
C2—Sn1—O3^i	82.7 (1)	C5—C6—C7	119.7 (5)
C2—Sn1—O1w	92.3 (2)	C5—C6—H6	120.1
C2—Sn1—N1	93.4 (2)	C7—C6—H6	120.1
C2—Sn1—O1	95.9 (2)	C2—C7—C6	121.2 (5)
N1—Sn1—O1	71.0 (1)	C2—C7—H7	119.4
N1—Sn1—O3	67.9 (1)	C6—C7—H7	119.4
N1—Sn1—O3^i	137.7 (1)	O2—C8—O1	125.0 (4)
N1—Sn1—O1w	145.5 (1)	O2—C8—C9	119.7 (4)
O1—Sn1—O1w	74.5 (1)	O1—C8—C9	115.3 (4)
O1—Sn1—O3	138.9 (1)	N1—C9—C10	122.2 (4)
O1—Sn1—O3^i	151.2 (1)	N1—C9—C8	113.5 (4)
O3—Sn1—O3^i	69.9 (1)	C10—C9—C8	124.3 (4)
O3—Sn1—O1w	146.6 (1)	C9—C10—C11	118.2 (4)
O3^i—Sn1—O1w	76.8 (1)	C9—C10—H10	120.9
Sn1—O1w—H1w1	109.5	C11—C10—H10	120.9
Sn1—O1w—H1w2	109.5	C10—C11—C12	119.6 (4)
H1w1—O1w—H1w2	109.5	C10—C11—H11	120.2
C8—O1—Sn1	122.3 (3)	C12—C11—H11	120.2
C14—O3—Sn1	119.5 (3)	C13—C12—C11	117.8 (4)
C9—N1—C13	119.9 (4)	C13—C12—H12	121.1
C9—N1—Sn1	117.5 (3)	C11—C12—H12	121.1
C13—N1—Sn1	122.6 (3)	N1—C13—C12	122.3 (4)
Sn1—C1—H1a	109.5	N1—C13—C14	114.6 (4)
Sn1—C1—H1b	109.5	C12—C13—C14	123.0 (4)
H1a—C1—H1b	109.5	O4—C14—O3	126.3 (4)
Sn1—C1—H1C	109.5	O4—C14—C13	118.4 (4)
H1a—C1—H1C	109.5	O3—C14—C13	115.2 (4)
H1b—C1—H1C	109.5	Cl1—C15—Cl3	113.0 (4)
C7—C2—C3	118.0 (5)	Cl1—C15—Cl2	109.8 (4)
C7—C2—Sn1	121.4 (4)	Cl3—C15—Cl2	109.4 (3)
C3—C2—Sn1	120.5 (4)	Cl1—C15—H15	108.2
C2—C3—C4	120.7 (5)	Cl3—C15—H15	108.2
C2—C3—H3	119.7	Cl2—C15—H15	108.2
C1—Sn1—O1—C8	97.2 (4)	O3^i—Sn1—C2—C3	56.4 (4)
C2—Sn1—O1—C8	−86.9 (4)	C7—C2—C3—C4	−1.9 (7)
O1w—Sn1—O1—C8	−177.7 (4)	Sn1—C2—C3—C4	178.9 (4)
N1—Sn1—O1—C8	4.7 (3)	C2—C3—C4—C5	1.0 (9)
O3—Sn1—O1—C8	3.9 (4)	C3—C4—C5—C6	0.0 (9)
O3^i—Sn1—O1—C8	−172.4 (3)	C4—C5—C6—C7	0.0 (8)
C1—Sn1—O3—C14	−93.0 (4)	C3—C2—C7—C6	1.8 (7)
C2—Sn1—O3—C14	98.8 (3)	Sn1—C2—C7—C6	−178.9 (4)
O1—Sn1—O3—C14	4.3 (4)	C5—C6—C7—C2	−0.9 (8)
O1w—Sn1—O3—C14	−172.9 (3)	Sn1—O1—C8—O2	176.0 (4)
N1—Sn1—O3—C14	3.5 (3)	Sn1—O1—C8—C9	−6.0 (6)
O3^i—Sn1—O3—C14	−177.6 (4)	C13—N1—C9—C10	−0.2 (7)
C1—Sn1—N1—C9	−98.5 (4)	Sn1—N1—C9—C10	179.7 (4)
C2—Sn1—N1—C9	92.7 (3)	C13—N1—C9—C8	−179.6 (4)
O1—Sn1—N1—C9	−2.3 (3)	Sn1—N1—C9—C8	0.3 (5)
O1w—Sn1—N1—C9	−6.3 (5)	O2—C8—C9—N1	−178.5 (4)
O3—Sn1—N1—C9	177.1 (4)	O1—C8—C9—N1	3.5 (6)
O3^i—Sn1—N1—C9	175.6 (3)	O2—C8—C9—C10	2.2 (7)
C1—Sn1—N1—C13	81.4 (4)	O1—C8—C9—C10	−175.9 (5)
C2—Sn1—N1—C13	−87.4 (4)	N1—C9—C10—C11	−0.1 (7)
O1—Sn1—N1—C13	177.6 (4)	C8—C9—C10—C11	179.2 (4)
O1w—Sn1—N1—C13	173.6 (3)	C9—C10—C11—C12	−0.4 (7)
O3—Sn1—N1—C13	−2.9 (3)	C10—C11—C12—C13	1.3 (8)
O3^i—Sn1—N1—C13	−4.5 (4)	C9—N1—C13—C12	1.1 (7)
C1—Sn1—C2—C7	−111.3 (8)	Sn1—N1—C13—C12	−178.8 (4)
O1—Sn1—C2—C7	86.1 (4)	C9—N1—C13—C14	−177.8 (4)
O1w—Sn1—C2—C7	160.7 (4)	Sn1—N1—C13—C14	2.3 (5)
N1—Sn1—C2—C7	14.8 (4)	C11—C12—C13—N1	−1.6 (7)
O3—Sn1—C2—C7	−52.7 (4)	C11—C12—C13—C14	177.2 (4)
O3^i—Sn1—C2—C7	−122.9 (4)	Sn1—O3—C14—O4	176.4 (4)
C1—Sn1—C2—C3	68.0 (9)	Sn1—O3—C14—C13	−3.6 (5)
O1—Sn1—C2—C3	−94.7 (4)	N1—C13—C14—O4	−179.0 (4)
O1w—Sn1—C2—C3	−20.0 (4)	C12—C13—C14—O4	2.1 (7)
N1—Sn1—C2—C3	−165.9 (4)	N1—C13—C14—O3	1.0 (6)
O3—Sn1—C2—C3	126.6 (4)	C12—C13—C14—O3	−177.9 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w2···O2^ii	0.84	1.89	2.656 (5)	151
O1w—H1w1···O4^i	0.84	1.81	2.641 (4)	169

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