Bis(μ-3-nitro­benzoato)-1:2κ2O:O′;3:4κ2O:O′-bis­(3-nitro­benzoato)-1κ2O,O′;3κ2O,O′-di-μ3-oxo-1:2:4κ3O;2:3:4κ3O-tetra­kis[di-n-butyl­tin(IV)]

Hong, M.; Yin, H.-D.; Wang, D.-Q.

doi:10.1107/S1600536805028369

Buy article online - an online subscription or single-article purchase is required to access this article.

Bis(μ-3-nitrobenzoato)-1:2κ²O:O′;3:4κ²O:O′-bis(3-nitrobenzoato)-1κ²O,O′;3κ²O,O′-di-μ₃-oxo-1:2:4κ³O;2:3:4κ³O-tetrakis[di-n-butyltin(IV)]

M. Hong, H.-D. Yin and D.-Q. Wang

The reaction of bis(tributyltin) oxide with 3-nitrobenzoic acid yields a stable crystalline material with the composition [Sn₄O₂(C₄H₉)₈(C₇H₄NO₄)₄O₂], which contains two bridging and two non-bridging (bidentate) 3-nitrobenzoate groups. It is a tetranuclear dimer in which there are two six-coordinate endocyclic and two six-coordinate exocyclic Sn atoms.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028369/br6213sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028369/br6213Isup2.hkl Contains datablock I

CCDC reference: 287455

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.010 Å
Disorder in main residue
R factor = 0.039
wR factor = 0.114
Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.26 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.24 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.55 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Sn1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT301_ALERT_3_C Main Residue  Disorder .........................       6.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.11 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  12 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
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Fig. 1 shows that the title compound, (I), is a tetranuclear centrosymmetric dimer with a central four-membered ring defined by Sn1—O9—Sn1ⁱ—O9ⁱ [symmetry code: (i) −x + 1, −y + 1, −z]. Two bridging carboxyl groups link the four Sn atoms, while the remaining two act as bidentate ligands to the exocyclic Sn atoms. Consideration of the axial angles O1—Sn1—O9 and O5—Sn2—O2ⁱ and of the Sn—O distances leads to the conclusion that the two Sn atoms are in different environments. Both Sn atoms are coordinated by two n-butyl moieties. In particular, as can be seen from Fig. 1, two of the eight n-butyl groups, those coordinated to atoms Sn1 or Sn1ⁱ atoms, contain three atoms, C16, C17 or C18, which occupy two positions. In the case of the exocyclic atom Sn2, coordination is completed by atoms O5, O6, O2ⁱ and O9. For the endocyclic atom Sn1, atoms O1, O9 and O9ⁱ all coordinate at different distances, and there is a weak but significant interaction to atom O5. Thus, it may be concluded that the exocyclic atom Sn2 is best described as six-coordinate and the endocyclic atom Sn1 as pseudo-six-coordinate.

A comparison between the structure of (I) and those of the amino-, ortho-methoxy- or ortho-nitrobenzoatodistannoxanes published previously (Narula et al., 1992; Chandrasechar et al., 1988), reveal that endocyclic Sn atoms in all types of compounds are six-coordinate, while the exocyclic Sn atoms are five-coordinate in the o-nitrobenzoato- and six-coordinate in the amino-, o-methoxy- or m-nitrobenzoatostannoxanes. The existence of such six- and five-coordinate Sn atoms has also been shown by X-ray analysis (Graziani et al., 1977; Valle et al., 1984) in tetra n-butyl bis(tri- or -dichloroacetoxy)distannoxanes. A close scrutiny of the available structural data for diorganostannoxanes (Graziani et al., 1977; Valle et al., 1984; Chow, 1971; Chandrasekhar Chandrasechar? et al., 1988; Narula et al., 1988) reveals that the choice between five- and six-coordinated exocyclic Sn atoms in this type of compound may depend upon the electronic effects of the substituents in the carboxyl ligands. This is supported by similar observations on triphenyltin benzoates (Molloy et al., 1988). Interestingly, the electronegative ligands influence the bonding characteristics of non-bridging but not those of bridging carboxyl groups.

Experimental top

meta-Nitrobenzoic acid (1 mmol) was added to a benzene suspension (30 ml) of bis(tributyltin) oxide (1 mmol) and the mixture was stirred and heated at reflux for 6 h. The clear solution obtained after filtration was evaporated in vacuo to give a solid, which was then recrystallized in dichloromethane–hexane (Ratio?). Light-yellowish crystals of (I) suitable for X-ray diffraction were obtained (m.p. 388 K). Elemental analysis, calculated for C₆₀H₈₈N₄O₁₈Sn₄: C 44.22, H 5.41, N 3.44%; found: C 44.25, H 5.33, N 3.51%.

Computing details top

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.

Figures top

Fig. 1. The structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity. Unlabelled atoms are related to labelled atoms by the symmetry operation (−x + 1, −y + 1, −z).

Bis(µ-3-nitrobenzoato)-1:2κ²O:O';3:4κ²O:O'-bis(3-nitrobenzoato)- 1κ²O,O';3κ²O,O'-di-µ₃-oxo-1:2:4κ³O;2:3:4κ³O- tetrakis[di-n-butyltin(IV)] top

Crystal data top

[Sn₄O₂(C₄H₉)₈(C₇H₄NO₄)₄O₂]	F(000) = 1640
M_r = 1628.10	D_x = 1.567 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 388 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.7885 (13) Å	Cell parameters from 5842 reflections
b = 11.6149 (13) Å	θ = 2.4–27.0°
c = 25.301 (3) Å	µ = 1.50 mm⁻¹
β = 94.903 (2)°	T = 298 K
V = 3451.6 (7) Å³	Block, colourless
Z = 2	0.41 × 0.35 × 0.29 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	6064 independent reflections
Radiation source: fine-focus sealed tube	4273 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→14
T_min = 0.579, T_max = 0.671	k = −13→13
17627 measured reflections	l = −30→19

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0576P)² + 4.7483P] where P = (F_o² + 2F_c²)/3
6064 reflections	(Δ/σ)_max < 0.001
408 parameters	Δρ_max = 0.79 e Å⁻³
243 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

[Sn₄O₂(C₄H₉)₈(C₇H₄NO₄)₄O₂]	V = 3451.6 (7) Å³
M_r = 1628.10	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.7885 (13) Å	µ = 1.50 mm⁻¹
b = 11.6149 (13) Å	T = 298 K
c = 25.301 (3) Å	0.41 × 0.35 × 0.29 mm
β = 94.903 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	6064 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4273 reflections with I > 2σ(I)
T_min = 0.579, T_max = 0.671	R_int = 0.035
17627 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	243 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.00	Δρ_max = 0.79 e Å⁻³
6064 reflections	Δρ_min = −0.56 e Å⁻³
408 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	Occ. (<1)
Sn1	0.40245 (3)	0.47798 (3)	0.042390 (16)	0.04126 (14)
Sn2	0.53073 (3)	0.76957 (3)	0.044228 (16)	0.04309 (14)
N1	0.0516 (5)	−0.1311 (6)	0.0528 (3)	0.0737 (18)
N2	0.1203 (7)	0.5520 (8)	0.2172 (3)	0.093 (2)
O1	0.2916 (4)	0.3265 (4)	0.05674 (19)	0.0658 (13)
O2	0.3393 (4)	0.1740 (4)	0.0121 (2)	0.0668 (13)
O3	0.1074 (6)	−0.1733 (5)	0.0210 (3)	0.115 (2)
O4	−0.0272 (6)	−0.1804 (6)	0.0712 (3)	0.127 (3)
O5	0.4062 (3)	0.7083 (3)	0.09710 (16)	0.0495 (10)
O6	0.4194 (4)	0.8938 (4)	0.11631 (19)	0.0687 (13)
O7	0.1591 (7)	0.4691 (7)	0.1960 (4)	0.130 (3)
O8	0.0491 (6)	0.5449 (7)	0.2493 (3)	0.133 (3)
O9	0.5234 (3)	0.6054 (3)	0.01624 (15)	0.0414 (9)
C1	0.2796 (4)	0.2209 (5)	0.0429 (2)	0.0418 (14)
C2	0.1859 (5)	0.1577 (5)	0.0659 (2)	0.0431 (14)
C3	0.1640 (5)	0.0457 (5)	0.0496 (2)	0.0480 (15)
H3	0.2072	0.0101	0.0251	0.058*
C4	0.0764 (5)	−0.0115 (5)	0.0708 (3)	0.0534 (16)
C5	0.0135 (6)	0.0366 (7)	0.1075 (3)	0.067 (2)
H5	−0.0448	−0.0049	0.1212	0.080*
C6	0.0365 (6)	0.1460 (7)	0.1240 (3)	0.073 (2)
H6	−0.0056	0.1799	0.1493	0.088*
C7	0.1229 (6)	0.2066 (6)	0.1031 (3)	0.0606 (18)
H7	0.1387	0.2816	0.1144	0.073*
C8	0.3761 (5)	0.7994 (6)	0.1216 (2)	0.0505 (16)
C9	0.2841 (5)	0.7839 (6)	0.1584 (2)	0.0478 (15)
C10	0.2436 (5)	0.6762 (6)	0.1693 (3)	0.0562 (17)
H10	0.2728	0.6112	0.1538	0.067*
C11	0.1587 (6)	0.6658 (7)	0.2036 (3)	0.066 (2)
C12	0.1139 (7)	0.7623 (9)	0.2260 (3)	0.080 (2)
H12	0.0564	0.7545	0.2487	0.096*
C13	0.1533 (7)	0.8680 (8)	0.2150 (3)	0.084 (2)
H13	0.1231	0.9328	0.2302	0.101*
C14	0.2389 (6)	0.8797 (7)	0.1812 (3)	0.0649 (19)
H14	0.2661	0.9526	0.1737	0.078*
C15	0.2529 (7)	0.5615 (7)	0.0104 (4)	0.088 (2)
H15A	0.2004	0.5673	0.0378	0.105*
H15B	0.2722	0.6391	0.0003	0.105*
C16	0.1945 (9)	0.5021 (8)	−0.0365 (4)	0.113 (2)	0.50
H16A	0.1494	0.4393	−0.0241	0.135*	0.50
H16B	0.2519	0.4688	−0.0572	0.135*	0.50
C17	0.1180 (17)	0.5777 (19)	−0.0724 (7)	0.111 (3)	0.518 (16)
H17A	0.0408	0.5691	−0.0624	0.133*	0.518 (16)
H17B	0.1402	0.6571	−0.0656	0.133*	0.518 (16)
C18	0.117 (2)	0.557 (2)	−0.1295 (7)	0.126 (5)	0.482 (16)
H18A	0.0668	0.6117	−0.1482	0.189*	0.482 (16)
H18B	0.0899	0.4805	−0.1374	0.189*	0.482 (16)
H18C	0.1922	0.5658	−0.1404	0.189*	0.482 (16)
C16'	0.1945 (9)	0.5021 (8)	−0.0365 (4)	0.113 (2)	0.50
H16C	0.1847	0.4219	−0.0272	0.135*	0.50
H16D	0.2449	0.5041	−0.0649	0.135*	0.50
C17'	0.0805 (19)	0.548 (2)	−0.0583 (11)	0.110 (3)	0.482 (16)
H17C	0.0265	0.5369	−0.0318	0.132*	0.482 (16)
H17D	0.0873	0.6298	−0.0643	0.132*	0.482 (16)
C18'	0.037 (2)	0.4965 (18)	−0.1049 (10)	0.122 (5)	0.518 (16)
H18D	−0.0351	0.5298	−0.1162	0.183*	0.518 (16)
H18E	0.0286	0.4154	−0.0993	0.183*	0.518 (16)
H18F	0.0891	0.5086	−0.1318	0.183*	0.518 (16)
C19	0.4924 (6)	0.4534 (6)	0.1179 (2)	0.0602 (16)
H19A	0.5687	0.4278	0.1120	0.072*
H19B	0.4999	0.5281	0.1350	0.072*
C20	0.4458 (7)	0.3710 (7)	0.1568 (3)	0.0753 (19)
H20A	0.4502	0.2931	0.1433	0.090*
H20B	0.3662	0.3886	0.1599	0.090*
C21	0.5110 (8)	0.3774 (8)	0.2123 (3)	0.091 (2)
H21A	0.4929	0.3099	0.2325	0.110*
H21B	0.5922	0.3762	0.2084	0.110*
C22	0.4827 (9)	0.4840 (8)	0.2425 (4)	0.114 (3)
H22A	0.5267	0.4849	0.2762	0.171*
H22B	0.4031	0.4839	0.2480	0.171*
H22C	0.5002	0.5511	0.2226	0.171*
C23	0.4071 (5)	0.8620 (5)	−0.0041 (2)	0.0553 (16)
H23A	0.3326	0.8420	0.0068	0.066*
H23B	0.4186	0.9435	0.0029	0.066*
C24	0.4057 (6)	0.8433 (7)	−0.0625 (3)	0.0724 (19)
H24A	0.4165	0.7620	−0.0692	0.087*
H24B	0.4693	0.8844	−0.0756	0.087*
C25	0.2977 (7)	0.8822 (7)	−0.0932 (3)	0.084 (2)
H25A	0.2351	0.8373	−0.0815	0.100*
H25B	0.2843	0.9619	−0.0842	0.100*
C26	0.2950 (9)	0.8730 (10)	−0.1517 (3)	0.121 (3)
H26A	0.2236	0.9016	−0.1675	0.182*
H26B	0.3037	0.7938	−0.1615	0.182*
H26C	0.3561	0.9176	−0.1641	0.182*
C27	0.6729 (7)	0.7793 (7)	0.1019 (3)	0.080 (2)
H27A	0.7354	0.7398	0.0871	0.096*
H27B	0.6942	0.8599	0.1050	0.096*
C28	0.6676 (7)	0.7363 (8)	0.1552 (3)	0.094 (2)
H28A	0.6507	0.6546	0.1532	0.113*
H28B	0.6046	0.7737	0.1706	0.113*
C29	0.7745 (7)	0.7532 (9)	0.1925 (3)	0.101 (2)
H29A	0.8391	0.7231	0.1756	0.121*
H29B	0.7868	0.8351	0.1978	0.121*
C30	0.7711 (10)	0.6975 (11)	0.2449 (4)	0.137 (4)
H30A	0.8408	0.7129	0.2662	0.206*
H30B	0.7621	0.6159	0.2403	0.206*
H30C	0.7081	0.7275	0.2623	0.206*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0445 (2)	0.0376 (2)	0.0444 (3)	−0.00190 (18)	0.01919 (18)	−0.00214 (17)
Sn2	0.0455 (3)	0.0347 (2)	0.0518 (3)	−0.00400 (18)	0.02003 (19)	−0.00503 (18)
N1	0.056 (4)	0.058 (4)	0.109 (6)	−0.013 (3)	0.017 (4)	0.004 (4)
N2	0.076 (5)	0.116 (7)	0.090 (6)	−0.022 (5)	0.027 (4)	0.015 (5)
O1	0.076 (3)	0.047 (3)	0.079 (3)	−0.015 (2)	0.037 (3)	−0.004 (2)
O2	0.060 (3)	0.057 (3)	0.091 (4)	−0.010 (2)	0.047 (3)	0.000 (3)
O3	0.103 (5)	0.064 (4)	0.188 (7)	−0.023 (3)	0.066 (5)	−0.034 (4)
O4	0.119 (5)	0.082 (4)	0.191 (7)	−0.055 (4)	0.070 (5)	−0.004 (5)
O5	0.054 (3)	0.040 (2)	0.058 (3)	−0.0026 (19)	0.028 (2)	−0.0052 (19)
O6	0.083 (3)	0.049 (3)	0.079 (3)	−0.016 (3)	0.038 (3)	−0.013 (2)
O7	0.126 (6)	0.099 (6)	0.173 (8)	−0.015 (5)	0.068 (6)	0.030 (5)
O8	0.105 (5)	0.176 (8)	0.128 (6)	−0.040 (5)	0.066 (5)	0.029 (5)
O9	0.045 (2)	0.032 (2)	0.049 (2)	−0.0015 (17)	0.0206 (18)	−0.0046 (17)
C1	0.027 (3)	0.059 (4)	0.041 (3)	0.005 (3)	0.009 (2)	0.012 (3)
C2	0.037 (3)	0.048 (4)	0.046 (4)	0.000 (3)	0.012 (3)	0.008 (3)
C3	0.043 (3)	0.044 (4)	0.059 (4)	0.006 (3)	0.016 (3)	0.006 (3)
C4	0.047 (4)	0.045 (4)	0.070 (5)	−0.002 (3)	0.013 (3)	0.007 (3)
C5	0.050 (4)	0.071 (5)	0.083 (5)	−0.006 (4)	0.029 (4)	0.019 (4)
C6	0.066 (5)	0.080 (6)	0.080 (6)	−0.005 (4)	0.041 (4)	−0.004 (4)
C7	0.062 (4)	0.052 (4)	0.071 (5)	−0.005 (3)	0.026 (4)	−0.005 (3)
C8	0.046 (4)	0.057 (4)	0.051 (4)	0.009 (3)	0.017 (3)	−0.002 (3)
C9	0.042 (3)	0.061 (4)	0.042 (4)	0.010 (3)	0.011 (3)	−0.007 (3)
C10	0.045 (4)	0.064 (4)	0.061 (4)	0.003 (3)	0.016 (3)	−0.001 (3)
C11	0.045 (4)	0.098 (6)	0.058 (5)	−0.003 (4)	0.020 (3)	0.011 (4)
C12	0.060 (5)	0.121 (8)	0.062 (5)	0.008 (5)	0.032 (4)	0.000 (5)
C13	0.080 (6)	0.098 (7)	0.078 (6)	0.019 (5)	0.032 (4)	−0.011 (5)
C14	0.068 (5)	0.074 (5)	0.055 (4)	0.012 (4)	0.019 (4)	−0.003 (4)
C15	0.066 (4)	0.068 (4)	0.126 (6)	0.007 (3)	−0.010 (4)	−0.010 (4)
C16	0.093 (4)	0.096 (4)	0.143 (5)	0.014 (4)	−0.026 (4)	−0.011 (4)
C17	0.092 (6)	0.092 (6)	0.143 (7)	0.010 (5)	−0.025 (6)	−0.009 (5)
C18	0.115 (9)	0.111 (8)	0.148 (9)	0.009 (8)	−0.013 (8)	−0.002 (8)
C16'	0.093 (4)	0.096 (4)	0.143 (5)	0.014 (4)	−0.026 (4)	−0.011 (4)
C17'	0.088 (6)	0.093 (6)	0.142 (7)	0.008 (5)	−0.024 (6)	−0.005 (6)
C18'	0.108 (8)	0.102 (8)	0.151 (9)	0.005 (7)	−0.029 (8)	−0.016 (8)
C19	0.070 (4)	0.062 (4)	0.050 (4)	0.001 (3)	0.014 (3)	0.008 (3)
C20	0.084 (4)	0.084 (5)	0.059 (4)	0.004 (4)	0.013 (3)	0.014 (4)
C21	0.100 (5)	0.108 (5)	0.066 (4)	0.013 (5)	0.008 (4)	0.013 (4)
C22	0.121 (7)	0.137 (8)	0.082 (6)	0.009 (6)	−0.003 (5)	0.003 (6)
C23	0.058 (4)	0.044 (3)	0.067 (4)	0.006 (3)	0.018 (3)	0.000 (3)
C24	0.075 (4)	0.075 (4)	0.070 (4)	0.015 (4)	0.017 (3)	0.006 (4)
C25	0.090 (5)	0.078 (4)	0.082 (5)	0.014 (4)	0.004 (4)	0.007 (4)
C26	0.135 (8)	0.144 (8)	0.083 (6)	0.026 (7)	−0.002 (6)	0.012 (6)
C27	0.070 (4)	0.099 (5)	0.071 (5)	−0.014 (4)	0.004 (4)	−0.015 (4)
C28	0.084 (5)	0.111 (5)	0.086 (5)	−0.009 (4)	0.000 (4)	−0.004 (4)
C29	0.087 (5)	0.129 (6)	0.086 (5)	0.000 (5)	−0.004 (4)	−0.015 (5)
C30	0.115 (8)	0.166 (9)	0.126 (8)	0.012 (7)	−0.016 (7)	0.011 (8)

Geometric parameters (Å, º) top

Sn1—O9ⁱ	2.031 (3)	C16—H16A	0.9700
Sn1—C15	2.112 (7)	C16—H16B	0.9700
Sn1—C19	2.125 (6)	C17—C18	1.463 (17)
Sn1—O9	2.195 (4)	C17—H17A	0.9700
Sn1—O1	2.240 (4)	C17—H17B	0.9700
Sn1—O5	3.011 (4)	C18—H18A	0.9600
Sn2—O9	2.034 (3)	C18—H18B	0.9600
Sn2—C23	2.113 (6)	C18—H18C	0.9600
Sn2—C27	2.129 (7)	C17'—C18'	1.38 (3)
Sn2—O5	2.188 (4)	C17'—H17C	0.9700
Sn2—O2ⁱ	2.275 (4)	C17'—H17D	0.9700
Sn2—O6	2.746 (4)	C18'—H18D	0.9600
N1—O3	1.188 (8)	C18'—H18E	0.9600
N1—O4	1.217 (8)	C18'—H18F	0.9600
N1—C4	1.483 (9)	C19—C20	1.510 (8)
N2—O7	1.212 (10)	C19—H19A	0.9700
N2—O8	1.220 (9)	C19—H19B	0.9700
N2—C11	1.448 (11)	C20—C21	1.543 (9)
O1—C1	1.280 (7)	C20—H20A	0.9700
O2—C1	1.223 (7)	C20—H20B	0.9700
O2—Sn2ⁱ	2.275 (4)	C21—C22	1.508 (10)
O5—C8	1.292 (7)	C21—H21A	0.9700
O6—C8	1.222 (7)	C21—H21B	0.9700
O9—Sn1ⁱ	2.031 (3)	C22—H22A	0.9600
C1—C2	1.485 (8)	C22—H22B	0.9600
C2—C7	1.372 (8)	C22—H22C	0.9600
C2—C3	1.382 (8)	C23—C24	1.494 (8)
C3—C4	1.375 (8)	C23—H23A	0.9700
C3—H3	0.9300	C23—H23B	0.9700
C4—C5	1.359 (10)	C24—C25	1.502 (9)
C5—C6	1.357 (10)	C24—H24A	0.9700
C5—H5	0.9300	C24—H24B	0.9700
C6—C7	1.380 (9)	C25—C26	1.482 (10)
C6—H6	0.9300	C25—H25A	0.9700
C7—H7	0.9300	C25—H25B	0.9700
C8—C9	1.499 (8)	C26—H26A	0.9600
C9—C10	1.375 (9)	C26—H26B	0.9600
C9—C14	1.381 (9)	C26—H26C	0.9600
C10—C11	1.386 (9)	C27—C28	1.445 (10)
C10—H10	0.9300	C27—H27A	0.9700
C11—C12	1.381 (11)	C27—H27B	0.9700
C12—C13	1.349 (11)	C28—C29	1.521 (10)
C12—H12	0.9300	C28—H28A	0.9700
C13—C14	1.385 (10)	C28—H28B	0.9700
C13—H13	0.9300	C29—C30	1.479 (11)
C14—H14	0.9300	C29—H29A	0.9700
C15—C16	1.491 (10)	C29—H29B	0.9700
C15—H15A	0.9700	C30—H30A	0.9600
C15—H15B	0.9700	C30—H30B	0.9600
C16—C17	1.506 (14)	C30—H30C	0.9600

O9ⁱ—Sn1—C15	109.7 (3)	C15—C16—H16B	108.5
O9ⁱ—Sn1—C19	112.3 (2)	C17—C16—H16B	108.5
C15—Sn1—C19	137.9 (3)	H16A—C16—H16B	107.5
O9ⁱ—Sn1—O9	76.70 (15)	C18—C17—C16	117.1 (15)
C15—Sn1—O9	96.7 (3)	C18—C17—H17A	108.0
C19—Sn1—O9	94.3 (2)	C16—C17—H17A	108.0
O9ⁱ—Sn1—O1	92.16 (15)	C18—C17—H17B	108.0
C15—Sn1—O1	86.7 (3)	C16—C17—H17B	108.0
C19—Sn1—O1	90.1 (2)	H17A—C17—H17B	107.3
O9—Sn1—O1	168.86 (15)	C17—C18—H18A	109.5
O9ⁱ—Sn1—O5	140.27 (12)	C17—C18—H18B	109.5
C15—Sn1—O5	75.3 (2)	H18A—C18—H18B	109.5
C19—Sn1—O5	73.7 (2)	C17—C18—H18C	109.5
O9—Sn1—O5	63.59 (11)	H18A—C18—H18C	109.5
O1—Sn1—O5	127.54 (14)	H18B—C18—H18C	109.5
O9—Sn2—C23	105.6 (2)	C18'—C17'—H17C	108.7
O9—Sn2—C27	107.2 (3)	C18'—C17'—H17D	108.7
C23—Sn2—C27	146.4 (3)	H17C—C17'—H17D	107.6
O9—Sn2—O5	84.08 (14)	C17'—C18'—H18D	109.5
C23—Sn2—O5	93.1 (2)	C17'—C18'—H18E	109.5
C27—Sn2—O5	97.4 (2)	H18D—C18'—H18E	109.5
O9—Sn2—O2ⁱ	93.63 (15)	C17'—C18'—H18F	109.5
C23—Sn2—O2ⁱ	87.7 (2)	H18D—C18'—H18F	109.5
C27—Sn2—O2ⁱ	83.2 (2)	H18E—C18'—H18F	109.5
O5—Sn2—O2ⁱ	177.70 (15)	C20—C19—Sn1	119.3 (5)
O9—Sn2—O6	135.69 (14)	C20—C19—H19A	107.5
C23—Sn2—O6	76.8 (2)	Sn1—C19—H19A	107.5
C27—Sn2—O6	84.8 (3)	C20—C19—H19B	107.5
O5—Sn2—O6	51.77 (14)	Sn1—C19—H19B	107.5
O2ⁱ—Sn2—O6	130.52 (15)	H19A—C19—H19B	107.0
O3—N1—O4	123.4 (7)	C19—C20—C21	112.4 (6)
O3—N1—C4	119.2 (6)	C19—C20—H20A	109.1
O4—N1—C4	117.4 (7)	C21—C20—H20A	109.1
O7—N2—O8	123.3 (9)	C19—C20—H20B	109.1
O7—N2—C11	118.9 (7)	C21—C20—H20B	109.1
O8—N2—C11	117.8 (9)	H20A—C20—H20B	107.9
C1—O1—Sn1	139.5 (4)	C22—C21—C20	112.7 (7)
C1—O2—Sn2ⁱ	136.6 (4)	C22—C21—H21A	109.1
C8—O5—Sn2	104.7 (4)	C20—C21—H21A	109.1
C8—O5—Sn1	162.7 (4)	C22—C21—H21B	109.1
Sn2—O5—Sn1	89.56 (12)	C20—C21—H21B	109.1
C8—O6—Sn2	80.2 (4)	H21A—C21—H21B	107.8
Sn1ⁱ—O9—Sn2	133.87 (18)	C21—C22—H22A	109.5
Sn1ⁱ—O9—Sn1	103.30 (15)	C21—C22—H22B	109.5
Sn2—O9—Sn1	122.46 (17)	H22A—C22—H22B	109.5
O2—C1—O1	123.0 (5)	C21—C22—H22C	109.5
O2—C1—C2	121.2 (6)	H22A—C22—H22C	109.5
O1—C1—C2	115.8 (5)	H22B—C22—H22C	109.5
C7—C2—C3	119.8 (6)	C24—C23—Sn2	116.6 (4)
C7—C2—C1	121.9 (6)	C24—C23—H23A	108.1
C3—C2—C1	118.4 (5)	Sn2—C23—H23A	108.1
C4—C3—C2	117.8 (6)	C24—C23—H23B	108.1
C4—C3—H3	121.1	Sn2—C23—H23B	108.1
C2—C3—H3	121.1	H23A—C23—H23B	107.3
C5—C4—C3	122.7 (6)	C23—C24—C25	113.9 (6)
C5—C4—N1	119.4 (6)	C23—C24—H24A	108.8
C3—C4—N1	117.9 (6)	C25—C24—H24A	108.8
C6—C5—C4	119.3 (6)	C23—C24—H24B	108.8
C6—C5—H5	120.4	C25—C24—H24B	108.8
C4—C5—H5	120.4	H24A—C24—H24B	107.7
C5—C6—C7	119.7 (7)	C26—C25—C24	116.0 (7)
C5—C6—H6	120.2	C26—C25—H25A	108.3
C7—C6—H6	120.2	C24—C25—H25A	108.3
C2—C7—C6	120.8 (7)	C26—C25—H25B	108.3
C2—C7—H7	119.6	C24—C25—H25B	108.3
C6—C7—H7	119.6	H25A—C25—H25B	107.4
O6—C8—O5	123.2 (6)	C25—C26—H26A	109.5
O6—C8—C9	120.5 (6)	C25—C26—H26B	109.5
O5—C8—C9	116.3 (6)	H26A—C26—H26B	109.5
C10—C9—C14	119.8 (6)	C25—C26—H26C	109.5
C10—C9—C8	121.1 (6)	H26A—C26—H26C	109.5
C14—C9—C8	119.2 (6)	H26B—C26—H26C	109.5
C9—C10—C11	119.1 (7)	C28—C27—Sn2	121.8 (6)
C9—C10—H10	120.4	C28—C27—H27A	106.9
C11—C10—H10	120.4	Sn2—C27—H27A	106.9
C12—C11—C10	120.6 (7)	C28—C27—H27B	106.9
C12—C11—N2	120.4 (7)	Sn2—C27—H27B	106.9
C10—C11—N2	119.0 (7)	H27A—C27—H27B	106.7
C13—C12—C11	120.2 (7)	C27—C28—C29	115.8 (7)
C13—C12—H12	119.9	C27—C28—H28A	108.3
C11—C12—H12	119.9	C29—C28—H28A	108.3
C12—C13—C14	119.9 (8)	C27—C28—H28B	108.3
C12—C13—H13	120.0	C29—C28—H28B	108.3
C14—C13—H13	120.0	H28A—C28—H28B	107.4
C9—C14—C13	120.4 (8)	C30—C29—C28	114.5 (8)
C9—C14—H14	119.8	C30—C29—H29A	108.6
C13—C14—H14	119.8	C28—C29—H29A	108.6
C16—C15—Sn1	114.0 (6)	C30—C29—H29B	108.6
C16—C15—H15A	108.8	C28—C29—H29B	108.6
Sn1—C15—H15A	108.8	H29A—C29—H29B	107.6
C16—C15—H15B	108.8	C29—C30—H30A	109.5
Sn1—C15—H15B	108.8	C29—C30—H30B	109.5
H15A—C15—H15B	107.7	H30A—C30—H30B	109.5
C15—C16—C17	115.0 (10)	C29—C30—H30C	109.5
C15—C16—H16A	108.5	H30A—C30—H30C	109.5
C17—C16—H16A	108.5	H30B—C30—H30C	109.5

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Sn₄O₂(C₄H₉)₈(C₇H₄NO₄)₄O₂]
M_r	1628.10
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.7885 (13), 11.6149 (13), 25.301 (3)
β (°)	94.903 (2)
V (Å³)	3451.6 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.50
Crystal size (mm)	0.41 × 0.35 × 0.29

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.579, 0.671
No. of measured, independent and observed [I > 2σ(I)] reflections	17627, 6064, 4273
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.114, 1.00
No. of reflections	6064
No. of parameters	408
No. of restraints	243
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.56

Computer programs: SMART (Siemens, 1996), SMART, SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

Selected geometric parameters (Å, º) top

Sn1—O9ⁱ	2.031 (3)	Sn2—O9	2.034 (3)
Sn1—C15	2.112 (7)	Sn2—C23	2.113 (6)
Sn1—C19	2.125 (6)	Sn2—C27	2.129 (7)
Sn1—O9	2.195 (4)	Sn2—O5	2.188 (4)
Sn1—O1	2.240 (4)	Sn2—O2ⁱ	2.275 (4)
Sn1—O5	3.011 (4)	Sn2—O6	2.746 (4)

O9ⁱ—Sn1—C15	109.7 (3)	O9—Sn2—C23	105.6 (2)
O9ⁱ—Sn1—C19	112.3 (2)	O9—Sn2—C27	107.2 (3)
C15—Sn1—C19	137.9 (3)	C23—Sn2—C27	146.4 (3)
O9ⁱ—Sn1—O9	76.70 (15)	O9—Sn2—O5	84.08 (14)
C15—Sn1—O9	96.7 (3)	C23—Sn2—O5	93.1 (2)
C19—Sn1—O9	94.3 (2)	C27—Sn2—O5	97.4 (2)
O9ⁱ—Sn1—O1	92.16 (15)	O9—Sn2—O2ⁱ	93.63 (15)
C15—Sn1—O1	86.7 (3)	C23—Sn2—O2ⁱ	87.7 (2)
C19—Sn1—O1	90.1 (2)	C27—Sn2—O2ⁱ	83.2 (2)
O9—Sn1—O1	168.86 (15)	O5—Sn2—O2ⁱ	177.70 (15)
O9ⁱ—Sn1—O5	140.27 (12)	O9—Sn2—O6	135.69 (14)
C15—Sn1—O5	75.3 (2)	C23—Sn2—O6	76.8 (2)

Symmetry code: (i) −x+1, −y+1, −z.

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page