(μ-2,2′-Biquinolinyl-4,4′-dicarboxyl­ato-κ²O:O′)bis­[(dimethyl­formamide-κO)triphenyl­tin(IV)]

The molecule of the title compound, [Sn₂(C₆H₅)₆(C₁₀H₅NO₂)₂(C₃H₇NO)₂], is centrosymmetric. Two triphenyl­tin groups are bridged by a 2,2′-biquinolinyl-4,4′-dicarboxyl­ate dianion (L) through its two carboxyl­ate groups. Each Sn atom displays a distorted trigonal–bipyramidal geometry composed of three phenyl groups, one carboxyl­ate O atom from the L dianion and one O atom of N,N-dimethyl­formamide. The mol­ecules display aromatic π–π stacking (face-to-face distance 3.406 Å).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.054
• wR factor = 0.170
• Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C20    -   C21     ..       9.97 su
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N2

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.47
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.09 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.18 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C28     ..       5.34 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     -   C3      ..       5.82 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Sn1    -   O1      ..       5.96 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11
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         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C7     -C12           1.37 Ang.
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C29
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C30

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  13 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

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S1. Comment

To further widen the scope of application of organotin compounds, there is a need to prepare new series of organotin compounds. In this paper, the structure of (I) is described.

The title compound (I) contains one neutral [Sn₂(C₆H₅)₆(C₉H₅NCOO)₂] molecule and two N,N-dimethyl formamide solvent molecules. As shown in Fig.1, two triphenyltin groups are bridged by the 2,2'-biquinoline-4,4'-dicarboxylate dianion, L, through its two carboxylate groups. The central Sn atom adopts distorted SnC₃O₂ trigonal bipyramid geometry composed of three phenyl groups, one carboxylate O atom from L and one O atom of N,N-dimethyl formamide. The N,N-dimethyl formamide, included as solvent molecule, forms no hydrogen-bonding interactions with any other atoms in the structure. In addition, the bond between Sn1 and O3 (2.605 (3) Å) is much more weaker than that of Sn1 and O1 (2.187 (4) Å) (Basu Baul et al., 2004). The L ligand of each molecule provides two quinoline rings to form slipped π-π interaction with the face-to-face distance (d) being about 3.406Å (Fig. 2).

Related literature

For related literature, see: Basu Baul et al. (2004).

S2. Experimental

A mixture of Na₂L (0.388 g, 1 mmol) and Ph₃SnCl (0.770 g, 2 mmol) in 25 ml e thanol was refluxed for 12 h and then filtered. The resulting precipitates were washed with ethanol. Crystals suitable for X-ray diffraction were obtained by slow evaporation of a N,N-dimethyl formamide solution.

S3. Refinement

All H-atoms bound to carbon were refined using a riding model with d(C—H) = 0.93 Å, U_iso=1.2U_eq (C) for aromatic and 0.96 Å, U_iso = 1.5U_eq (C) for CH₃ atoms. The minimum electron-density peak is located 0.96Å from atom Sn1.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. View of the compound (I). Displacement ellipsoids are drawn at the 30% probability level. (symmetry code: (i) 1 - x, 1 - y, 1 - z)
	Fig. 2. A packing diagram of (I).

(µ-2,2'-Biquinolinyl-4,4'-dicarboxylato-κ²O:O')bis[(dimethylformamide- κO)triphenyltin(IV)]

Crystal data

[Sn2(C6H5)6(C10H5NO2)2(C3H7NO)2]	F(000) = 2408
Mr = 1188.47	Dx = 1.472 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6203 reflections
a = 30.4592 (17) Å	θ = 1.6–28.3°
b = 9.5344 (5) Å	µ = 0.99 mm^−1
c = 22.0343 (14) Å	T = 293 K
β = 123.051 (2)°	Block, colourless
V = 5363.5 (5) Å^3	0.54 × 0.48 × 0.39 mm
Z = 4

Data collection

Bruker APEX CCD area-detector diffractometer	6203 independent reflections
Radiation source: fine-focus sealed tube	4618 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −40→26
Tmin = 0.590, Tmax = 0.678	k = −12→10
15947 measured reflections	l = −26→29

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.170	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.1137P)^2] where P = (Fo^2 + 2Fc^2)/3
6203 reflections	(Δ/σ)max = 0.001
334 parameters	Δρmax = 2.82 e Å^−3
0 restraints	Δρmin = −1.14 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	0.347644 (10)	0.11246 (3)	0.186776 (13)	0.04892 (14)
C1	0.37845 (18)	−0.0948 (5)	0.2087 (2)	0.0555 (11)
C2	0.36527 (18)	−0.1935 (5)	0.2426 (2)	0.0593 (11)
H2	0.3448	−0.1670	0.2602	0.071*
C3	0.3825 (2)	−0.3329 (6)	0.2507 (3)	0.0728 (13)
H3	0.3731	−0.3993	0.2724	0.087*
C4	0.4137 (3)	−0.3694 (5)	0.2257 (3)	0.0765 (16)
H4	0.4251	−0.4616	0.2304	0.092*
C5	0.4280 (2)	−0.2738 (7)	0.1948 (3)	0.0810 (15)
H5	0.4495	−0.2999	0.1788	0.097*
C6	0.4110 (2)	−0.1384 (6)	0.1867 (3)	0.0693 (13)
H6	0.4216	−0.0735	0.1657	0.083*
C7	0.27208 (17)	0.1477 (6)	0.1675 (2)	0.0567 (11)
C8	0.2439 (2)	0.0377 (8)	0.1703 (3)	0.0898 (17)
H8	0.2588	−0.0513	0.1823	0.108*
C9	0.1931 (2)	0.0564 (9)	0.1553 (4)	0.0997 (19)
H9	0.1751	−0.0185	0.1588	0.120*
C10	0.1708 (2)	0.1853 (9)	0.1356 (3)	0.094 (2)
H10	0.1365	0.1988	0.1225	0.113*
C11	0.1984 (3)	0.2913 (9)	0.1352 (5)	0.121 (3)
H11	0.1839	0.3807	0.1245	0.145*
C12	0.2486 (3)	0.2729 (8)	0.1503 (4)	0.102 (2)
H12	0.2664	0.3502	0.1485	0.122*
C13	0.37577 (16)	0.2455 (4)	0.1378 (2)	0.0487 (9)
C14	0.3425 (2)	0.3145 (5)	0.0722 (3)	0.0650 (12)
H14	0.3066	0.2999	0.0481	0.078*
C15	0.3608 (3)	0.4014 (6)	0.0428 (4)	0.0840 (18)
H15	0.3374	0.4478	−0.0002	0.101*
C16	0.4128 (4)	0.4219 (6)	0.0753 (5)	0.096 (2)
H16	0.4253	0.4799	0.0540	0.116*
C17	0.4480 (3)	0.3552 (6)	0.1413 (4)	0.0890 (19)
H17	0.4839	0.3697	0.1645	0.107*
C18	0.42890 (18)	0.2687 (5)	0.1710 (3)	0.0672 (12)
H18	0.4522	0.2243	0.2147	0.081*
C19	0.44734 (17)	0.1592 (6)	0.4717 (3)	0.0637 (12)
C20	0.4307 (2)	0.0166 (7)	0.4709 (4)	0.088 (2)
H20	0.4080	−0.0268	0.4267	0.105*
C21	0.4477 (3)	−0.0562 (8)	0.5337 (5)	0.0917 (18)
H21	0.4369	−0.1483	0.5315	0.110*
C22	0.4809 (2)	0.0069 (7)	0.6004 (4)	0.0861 (16)
H22	0.4915	−0.0423	0.6427	0.103*
C23	0.4981 (2)	0.1400 (6)	0.6043 (3)	0.0698 (13)
H23	0.5211	0.1796	0.6495	0.084*
C24	0.48187 (17)	0.2212 (5)	0.5406 (3)	0.0612 (11)
C25	0.48861 (15)	0.4313 (5)	0.4933 (2)	0.0549 (10)
C26	0.45349 (18)	0.3773 (5)	0.4212 (2)	0.0632 (13)
H26	0.4448	0.4320	0.3812	0.076*
C27	0.43283 (16)	0.2450 (6)	0.4116 (3)	0.0658 (14)
C28	0.3947 (2)	0.1862 (8)	0.3373 (3)	0.087 (2)
C29	0.2256 (3)	−0.1292 (7)	−0.0722 (4)	0.109 (3)
H29A	0.2124	−0.1853	−0.1149	0.163*
H29C	0.2084	−0.0397	−0.0852	0.163*
H29B	0.2190	−0.1759	−0.0393	0.163*
C30	0.3076 (4)	−0.1706 (11)	−0.0725 (6)	0.151 (4)
H30B	0.2818	−0.2201	−0.1154	0.226*
H30C	0.3346	−0.2345	−0.0397	0.226*
H30A	0.3226	−0.0972	−0.0853	0.226*
C31	0.3084 (2)	−0.0349 (5)	0.0229 (3)	0.0668 (12)
H31	0.3437	−0.0186	0.0418	0.080*
N1	0.50173 (14)	0.3517 (4)	0.55044 (19)	0.0541 (8)
N2	0.2823 (2)	−0.1090 (4)	−0.0371 (3)	0.0769 (13)
O1	0.40005 (16)	0.2196 (6)	0.2896 (2)	0.1038 (15)
O2	0.3613 (2)	0.0932 (5)	0.3264 (2)	0.0980 (14)
O3	0.29056 (13)	0.0138 (3)	0.05551 (17)	0.0662 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.03819 (19)	0.0677 (2)	0.03760 (19)	0.00386 (11)	0.01859 (14)	0.00340 (11)
C1	0.044 (2)	0.078 (3)	0.042 (2)	0.0083 (19)	0.0216 (19)	0.0107 (19)
C2	0.056 (3)	0.066 (3)	0.053 (2)	0.006 (2)	0.029 (2)	0.001 (2)
C3	0.062 (3)	0.082 (3)	0.058 (3)	−0.006 (3)	0.023 (2)	−0.002 (3)
C4	0.075 (4)	0.064 (3)	0.075 (4)	0.010 (2)	0.030 (3)	−0.005 (2)
C5	0.071 (3)	0.099 (4)	0.084 (4)	0.021 (3)	0.049 (3)	0.001 (3)
C6	0.062 (3)	0.089 (4)	0.063 (3)	0.016 (2)	0.038 (3)	0.010 (2)
C7	0.042 (2)	0.087 (3)	0.043 (2)	0.004 (2)	0.0235 (18)	−0.002 (2)
C8	0.059 (3)	0.105 (4)	0.110 (5)	0.011 (3)	0.049 (3)	0.014 (4)
C9	0.064 (4)	0.131 (5)	0.112 (5)	−0.008 (4)	0.054 (4)	0.004 (5)
C10	0.053 (3)	0.157 (6)	0.078 (4)	0.025 (4)	0.039 (3)	0.001 (4)
C11	0.081 (4)	0.120 (6)	0.174 (8)	0.037 (4)	0.077 (5)	0.020 (5)
C12	0.070 (4)	0.103 (5)	0.141 (6)	0.023 (3)	0.063 (4)	0.024 (4)
C13	0.049 (2)	0.052 (2)	0.048 (2)	−0.0061 (17)	0.0279 (18)	−0.0119 (17)
C14	0.065 (3)	0.079 (3)	0.054 (3)	−0.006 (2)	0.035 (2)	−0.006 (2)
C15	0.122 (6)	0.070 (3)	0.083 (4)	0.006 (3)	0.070 (4)	0.012 (3)
C16	0.136 (7)	0.064 (3)	0.144 (7)	−0.009 (4)	0.112 (6)	0.003 (4)
C17	0.079 (4)	0.080 (4)	0.133 (6)	−0.027 (3)	0.074 (4)	−0.027 (4)
C18	0.051 (3)	0.075 (3)	0.076 (3)	−0.006 (2)	0.034 (2)	−0.017 (2)
C19	0.037 (2)	0.092 (3)	0.060 (3)	0.001 (2)	0.025 (2)	−0.022 (3)
C20	0.048 (3)	0.097 (4)	0.116 (5)	−0.016 (3)	0.043 (3)	−0.049 (4)
C21	0.077 (4)	0.089 (4)	0.126 (6)	0.007 (3)	0.066 (4)	0.018 (4)
C22	0.071 (4)	0.105 (4)	0.091 (4)	0.007 (3)	0.050 (3)	0.008 (4)
C23	0.065 (3)	0.078 (3)	0.074 (3)	0.004 (2)	0.042 (3)	0.000 (3)
C24	0.042 (2)	0.084 (3)	0.058 (3)	−0.002 (2)	0.028 (2)	−0.015 (2)
C25	0.039 (2)	0.089 (3)	0.0334 (18)	0.0039 (19)	0.0180 (17)	−0.013 (2)
C26	0.042 (2)	0.106 (4)	0.035 (2)	0.005 (2)	0.0172 (19)	−0.016 (2)
C27	0.034 (2)	0.099 (4)	0.059 (3)	−0.009 (2)	0.022 (2)	−0.039 (3)
C28	0.052 (3)	0.156 (6)	0.054 (3)	−0.018 (3)	0.029 (2)	−0.045 (4)
C29	0.091 (5)	0.098 (5)	0.091 (5)	−0.041 (4)	0.020 (4)	−0.013 (3)
C30	0.180 (9)	0.156 (7)	0.193 (10)	−0.066 (7)	0.151 (9)	−0.092 (7)
C31	0.059 (3)	0.073 (3)	0.066 (3)	−0.020 (2)	0.032 (2)	−0.014 (2)
N1	0.0448 (19)	0.074 (2)	0.0385 (17)	0.0026 (17)	0.0192 (15)	−0.0070 (16)
N2	0.086 (3)	0.078 (3)	0.072 (3)	−0.031 (2)	0.047 (3)	−0.023 (2)
O1	0.062 (2)	0.178 (5)	0.048 (2)	−0.017 (3)	0.0146 (18)	−0.008 (2)
O2	0.087 (3)	0.118 (3)	0.071 (3)	−0.031 (2)	0.032 (2)	−0.003 (2)
O3	0.066 (2)	0.072 (2)	0.0561 (18)	−0.0086 (16)	0.0304 (16)	−0.0120 (15)

Geometric parameters (Å, º)

Sn1—C13	2.125 (4)	C17—C18	1.364 (8)
Sn1—C7	2.127 (4)	C17—H17	0.9300
Sn1—C1	2.127 (4)	C18—H18	0.9300
Sn1—O1	2.187 (4)	C19—C27	1.407 (8)
C1—C6	1.384 (7)	C19—C24	1.422 (7)
C1—C2	1.390 (6)	C19—C20	1.447 (8)
C2—C3	1.404 (7)	C20—C21	1.371 (9)
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.377 (8)	C21—C22	1.387 (10)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.344 (8)	C22—C23	1.358 (8)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.366 (7)	C23—C24	1.433 (8)
C5—H5	0.9300	C23—H23	0.9300
C6—H6	0.9300	C24—N1	1.349 (6)
C7—C12	1.337 (8)	C25—N1	1.331 (6)
C7—C8	1.378 (8)	C25—C25^i	1.436 (10)
C8—C9	1.406 (8)	C25—C26	1.443 (6)
C8—H8	0.9300	C26—C27	1.373 (7)
C9—C10	1.356 (11)	C26—H26	0.9300
C9—H9	0.9300	C27—C28	1.507 (6)
C10—C11	1.318 (10)	C28—O1	1.190 (7)
C10—H10	0.9300	C28—O2	1.270 (8)
C11—C12	1.385 (9)	C29—N2	1.471 (9)
C11—H11	0.9300	C29—H29A	0.9600
C12—H12	0.9300	C29—H29C	0.9600
C13—C18	1.383 (6)	C29—H29B	0.9600
C13—C14	1.397 (7)	C30—N2	1.482 (9)
C14—C15	1.345 (8)	C30—H30B	0.9600
C14—H14	0.9300	C30—H30C	0.9600
C15—C16	1.351 (11)	C30—H30A	0.9600
C15—H15	0.9300	C31—O3	1.206 (6)
C16—C17	1.403 (11)	C31—N2	1.316 (6)
C16—H16	0.9300	C31—H31	0.9300
C13—Sn1—C7	119.75 (18)	C18—C17—H17	120.4
C13—Sn1—C1	114.85 (16)	C16—C17—H17	120.4
C7—Sn1—C1	119.16 (19)	C17—C18—C13	121.7 (6)
C13—Sn1—O1	88.78 (16)	C17—C18—H18	119.2
C7—Sn1—O1	103.41 (17)	C13—C18—H18	119.2
C1—Sn1—O1	102.48 (19)	C27—C19—C24	115.7 (5)
C6—C1—C2	117.2 (4)	C27—C19—C20	127.4 (5)
C6—C1—Sn1	120.7 (4)	C24—C19—C20	117.0 (5)
C2—C1—Sn1	122.0 (3)	C21—C20—C19	121.8 (6)
C1—C2—C3	120.7 (5)	C21—C20—H20	119.1
C1—C2—H2	119.7	C19—C20—H20	119.1
C3—C2—H2	119.7	C20—C21—C22	120.3 (6)
C4—C3—C2	118.8 (5)	C20—C21—H21	119.9
C4—C3—H3	120.6	C22—C21—H21	119.9
C2—C3—H3	120.6	C23—C22—C21	120.4 (6)
C5—C4—C3	121.0 (5)	C23—C22—H22	119.8
C5—C4—H4	119.5	C21—C22—H22	119.8
C3—C4—H4	119.5	C22—C23—C24	121.8 (6)
C4—C5—C6	120.2 (5)	C22—C23—H23	119.1
C4—C5—H5	119.9	C24—C23—H23	119.1
C6—C5—H5	119.9	N1—C24—C19	124.1 (5)
C5—C6—C1	122.1 (5)	N1—C24—C23	117.2 (4)
C5—C6—H6	119.0	C19—C24—C23	118.7 (5)
C1—C6—H6	119.0	N1—C25—C25^i	117.6 (4)
C12—C7—C8	116.2 (5)	N1—C25—C26	119.9 (5)
C12—C7—Sn1	123.5 (4)	C25^i—C25—C26	122.5 (5)
C8—C7—Sn1	120.2 (4)	C27—C26—C25	120.0 (5)
C7—C8—C9	121.7 (6)	C27—C26—H26	120.0
C7—C8—H8	119.1	C25—C26—H26	120.0
C9—C8—H8	119.1	C26—C27—C19	120.5 (4)
C10—C9—C8	119.0 (7)	C26—C27—C28	121.7 (6)
C10—C9—H9	120.5	C19—C27—C28	117.8 (5)
C8—C9—H9	120.5	O1—C28—O2	120.1 (5)
C11—C10—C9	119.2 (6)	O1—C28—C27	117.7 (6)
C11—C10—H10	120.4	O2—C28—C27	121.8 (6)
C9—C10—H10	120.4	N2—C29—H29A	109.5
C10—C11—C12	121.7 (7)	N2—C29—H29C	109.5
C10—C11—H11	119.2	H29A—C29—H29C	109.5
C12—C11—H11	119.2	N2—C29—H29B	109.5
C7—C12—C11	122.1 (7)	H29A—C29—H29B	109.5
C7—C12—H12	118.9	H29C—C29—H29B	109.5
C11—C12—H12	118.9	N2—C30—H30B	109.5
C18—C13—C14	116.8 (4)	N2—C30—H30C	109.5
C18—C13—Sn1	120.4 (4)	H30B—C30—H30C	109.5
C14—C13—Sn1	122.7 (3)	N2—C30—H30A	109.5
C15—C14—C13	122.1 (5)	H30B—C30—H30A	109.5
C15—C14—H14	119.0	H30C—C30—H30A	109.5
C13—C14—H14	119.0	O3—C31—N2	125.7 (5)
C14—C15—C16	120.5 (6)	O3—C31—H31	117.2
C14—C15—H15	119.7	N2—C31—H31	117.2
C16—C15—H15	119.7	C25—N1—C24	119.8 (4)
C15—C16—C17	119.7 (5)	C31—N2—C29	119.4 (5)
C15—C16—H16	120.2	C31—N2—C30	122.6 (6)
C17—C16—H16	120.2	C29—N2—C30	118.0 (6)
C18—C17—C16	119.1 (6)	C28—O1—Sn1	114.5 (4)
C13—Sn1—C1—C6	−4.8 (5)	C15—C16—C17—C18	1.0 (10)
C7—Sn1—C1—C6	147.4 (4)	C16—C17—C18—C13	−0.2 (8)
O1—Sn1—C1—C6	−99.3 (4)	C14—C13—C18—C17	0.2 (7)
C13—Sn1—C1—C2	178.0 (3)	Sn1—C13—C18—C17	−179.1 (4)
C7—Sn1—C1—C2	−29.8 (4)	C27—C19—C20—C21	−179.9 (5)
O1—Sn1—C1—C2	83.5 (4)	C24—C19—C20—C21	−0.5 (7)
C6—C1—C2—C3	−2.9 (7)	C19—C20—C21—C22	1.2 (8)
Sn1—C1—C2—C3	174.3 (4)	C20—C21—C22—C23	−1.8 (9)
C1—C2—C3—C4	1.4 (7)	C21—C22—C23—C24	1.6 (8)
C2—C3—C4—C5	0.6 (8)	C27—C19—C24—N1	−2.1 (6)
C3—C4—C5—C6	−0.9 (9)	C20—C19—C24—N1	178.5 (4)
C4—C5—C6—C1	−0.8 (9)	C27—C19—C24—C23	179.8 (4)
C2—C1—C6—C5	2.7 (8)	C20—C19—C24—C23	0.3 (6)
Sn1—C1—C6—C5	−174.6 (4)	C22—C23—C24—N1	−179.2 (5)
C13—Sn1—C7—C12	−26.3 (6)	C22—C23—C24—C19	−0.9 (7)
C1—Sn1—C7—C12	−177.2 (5)	N1—C25—C26—C27	1.3 (6)
O1—Sn1—C7—C12	70.0 (5)	C25^i—C25—C26—C27	−180.0 (5)
C13—Sn1—C7—C8	151.7 (4)	C25—C26—C27—C19	−2.6 (6)
C1—Sn1—C7—C8	0.9 (5)	C25—C26—C27—C28	178.1 (4)
O1—Sn1—C7—C8	−111.9 (4)	C24—C19—C27—C26	2.9 (6)
C12—C7—C8—C9	0.5 (9)	C20—C19—C27—C26	−177.7 (4)
Sn1—C7—C8—C9	−177.7 (5)	C24—C19—C27—C28	−177.8 (4)
C7—C8—C9—C10	2.0 (10)	C20—C19—C27—C28	1.6 (7)
C8—C9—C10—C11	−4.1 (11)	C26—C27—C28—O1	33.8 (9)
C9—C10—C11—C12	3.8 (13)	C19—C27—C28—O1	−145.5 (6)
C8—C7—C12—C11	−0.8 (11)	C26—C27—C28—O2	−153.2 (6)
Sn1—C7—C12—C11	177.3 (7)	C19—C27—C28—O2	27.5 (8)
C10—C11—C12—C7	−1.3 (14)	C25^i—C25—N1—C24	−179.2 (4)
C7—Sn1—C13—C18	151.2 (3)	C26—C25—N1—C24	−0.4 (6)
C1—Sn1—C13—C18	−56.8 (4)	C19—C24—N1—C25	0.9 (6)
O1—Sn1—C13—C18	46.4 (4)	C23—C24—N1—C25	179.0 (4)
C7—Sn1—C13—C14	−28.0 (4)	O3—C31—N2—C29	4.4 (8)
C1—Sn1—C13—C14	124.0 (4)	O3—C31—N2—C30	−177.3 (7)
O1—Sn1—C13—C14	−132.8 (4)	O2—C28—O1—Sn1	1.2 (9)
C18—C13—C14—C15	−1.0 (7)	C27—C28—O1—Sn1	174.3 (4)
Sn1—C13—C14—C15	178.2 (4)	C13—Sn1—O1—C28	173.5 (5)
C13—C14—C15—C16	1.9 (9)	C7—Sn1—O1—C28	53.1 (6)
C14—C15—C16—C17	−1.9 (10)	C1—Sn1—O1—C28	−71.3 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.