An indenide-tethered N-heterocyclic stannylene

Analysis of the coordination of the Sn to the indenyl ring shows that the Sn inter­acts in an η² fashion. A database survey showed that whilst this coordination mode is unusual for Ge and Pb compounds, Sn displays a wider range of coordination modes to cyclo­penta­dienyl ligands and their derivatives.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.042
• wR factor = 0.096
• Data-to-parameter ratio = 20.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.30 Report
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         52 Ang   3

Alert level G
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT793_ALERT_4_G Model has Chirality at N1          (Centro SPGR)          S Verify
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(µ-1κN:2(η²),κ²N,N'-(2-{[2,6-Bis(propan-2-yl)\ phenyl]azanidyl}ethyl)[2-(1H-inden-1-yl)ethyl]azanido)(1,4,7,10,13,16-\ hexaoxacyclooctadecane-1κ⁶O)lithiumtin

Crystal data

[LiSn(C8H16O4)(C25H32N2)]	F(000) = 1376
Mr = 661.35	Dx = 1.319 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.9766 (8) Å	Cell parameters from 7023 reflections
b = 17.7991 (14) Å	θ = 2.4–25.7°
c = 18.8402 (14) Å	µ = 0.80 mm^−1
β = 95.510 (4)°	T = 100 K
V = 3330.1 (4) Å^3	Block, pale yellow
Z = 4	0.20 × 0.20 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer	5184 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.051
Absorption correction: multi-scan (SADABS; Bruker, 2015)	θmax = 27.5°, θmin = 2.5°
Tmin = 0.614, Tmax = 0.746	h = −12→11
25958 measured reflections	k = −23→20
7615 independent reflections	l = −24→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0367P)^2 + 2.6456P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
7615 reflections	Δρmax = 1.36 e Å^−3
374 parameters	Δρmin = −0.59 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Sn1	0.62831 (2)	0.62730 (2)	0.73575 (2)	0.01853 (8)
O1	0.7755 (3)	0.69869 (14)	0.93346 (13)	0.0333 (6)
O2	0.9148 (3)	0.75607 (14)	0.82933 (13)	0.0337 (6)
O3	0.7698 (3)	0.88333 (13)	0.83378 (12)	0.0291 (6)
O4	0.6260 (3)	0.82577 (14)	0.93572 (12)	0.0311 (6)
N1	0.5656 (3)	0.73222 (15)	0.77937 (13)	0.0189 (6)
N2	0.4936 (3)	0.58853 (15)	0.80578 (14)	0.0208 (6)
C1	0.5055 (4)	0.70370 (19)	0.62151 (17)	0.0221 (8)
C2	0.4399 (3)	0.63288 (19)	0.62289 (16)	0.0215 (7)
H2	0.3654	0.6220	0.6490	0.026*
C3	0.5018 (4)	0.58133 (19)	0.57967 (17)	0.0226 (8)
H3	0.4765	0.5303	0.5718	0.027*
C4	0.6080 (3)	0.61883 (18)	0.55015 (16)	0.0202 (7)
C5	0.7031 (4)	0.5971 (2)	0.50330 (17)	0.0233 (8)
H5	0.7044	0.5468	0.4865	0.028*
C6	0.7938 (4)	0.6485 (2)	0.48200 (19)	0.0293 (9)
H6	0.8570	0.6335	0.4501	0.035*
C7	0.7942 (4)	0.7236 (2)	0.50699 (19)	0.0303 (9)
H7	0.8569	0.7587	0.4913	0.036*
C8	0.7050 (4)	0.7461 (2)	0.55352 (18)	0.0264 (8)
H8	0.7068	0.7965	0.5703	0.032*
C9	0.6111 (4)	0.69545 (18)	0.57669 (17)	0.0198 (8)
C10	0.4676 (4)	0.77556 (19)	0.65700 (17)	0.0235 (8)
H10A	0.3728	0.7720	0.6681	0.028*
H10B	0.4738	0.8177	0.6232	0.028*
C11	0.5574 (4)	0.79301 (18)	0.72628 (17)	0.0237 (8)
H11A	0.6495	0.8044	0.7139	0.028*
H11B	0.5224	0.8387	0.7482	0.028*
C12	0.4363 (4)	0.72044 (19)	0.80929 (18)	0.0231 (8)
H12A	0.3623	0.7200	0.7703	0.028*
H12B	0.4198	0.7622	0.8420	0.028*
C13	0.4379 (4)	0.64653 (19)	0.84949 (18)	0.0249 (8)
H13A	0.4937	0.6513	0.8956	0.030*
H13B	0.3453	0.6328	0.8592	0.030*
C14	0.4705 (4)	0.51260 (18)	0.82625 (18)	0.0226 (8)
C15	0.5655 (4)	0.47385 (19)	0.87310 (18)	0.0251 (8)
C16	0.5425 (4)	0.3981 (2)	0.8873 (2)	0.0331 (9)
H16	0.6060	0.3714	0.9186	0.040*
C17	0.4290 (5)	0.3613 (2)	0.8567 (2)	0.0381 (11)
H17	0.4165	0.3094	0.8658	0.046*
C18	0.3346 (4)	0.3998 (2)	0.8133 (2)	0.0330 (9)
H18	0.2560	0.3745	0.7933	0.040*
C19	0.3522 (4)	0.4757 (2)	0.79801 (18)	0.0250 (8)
C20	0.6928 (4)	0.5109 (2)	0.90675 (19)	0.0271 (8)
H20	0.6865	0.5657	0.8952	0.033*
C21	0.7086 (5)	0.5034 (3)	0.9890 (2)	0.0440 (11)
H21A	0.6293	0.5247	1.0085	0.066*
H21B	0.7893	0.5305	1.0084	0.066*
H21C	0.7172	0.4502	1.0020	0.066*
C22	0.8186 (4)	0.4806 (2)	0.8764 (2)	0.0392 (10)
H22A	0.8278	0.4268	0.8871	0.059*
H22B	0.8980	0.5074	0.8981	0.059*
H22C	0.8106	0.4880	0.8247	0.059*
C23	0.2422 (4)	0.5165 (2)	0.75159 (19)	0.0283 (9)
H23	0.2722	0.5696	0.7462	0.034*
C24	0.2197 (4)	0.4818 (2)	0.6765 (2)	0.0389 (10)
H24A	0.3044	0.4828	0.6541	0.058*
H24B	0.1512	0.5108	0.6475	0.058*
H24C	0.1893	0.4297	0.6802	0.058*
C25	0.1108 (4)	0.5182 (2)	0.7863 (2)	0.0414 (11)
H25A	0.0446	0.5487	0.7573	0.062*
H25B	0.1266	0.5402	0.8341	0.062*
H25C	0.0764	0.4669	0.7900	0.062*
C26	0.9184 (4)	0.6953 (3)	0.9438 (2)	0.0452 (11)
H26A	0.9476	0.6495	0.9708	0.054*
H26B	0.9545	0.7397	0.9709	0.054*
C27	0.9679 (5)	0.6939 (2)	0.8719 (2)	0.0455 (11)
H27A	1.0675	0.6962	0.8768	0.055*
H27B	0.9405	0.6461	0.8477	0.055*
C28	0.9884 (4)	0.8245 (2)	0.8415 (2)	0.0401 (10)
H28A	1.0747	0.8222	0.8197	0.048*
H28B	1.0079	0.8338	0.8933	0.048*
C29	0.9000 (4)	0.8856 (2)	0.8075 (2)	0.0345 (10)
H29A	0.9423	0.9351	0.8183	0.041*
H29B	0.8903	0.8789	0.7551	0.041*
C30	0.7597 (4)	0.9279 (2)	0.8967 (2)	0.0361 (10)
H30A	0.7581	0.9821	0.8847	0.043*
H30B	0.8373	0.9181	0.9323	0.043*
C31	0.6316 (4)	0.9053 (2)	0.9252 (2)	0.0392 (10)
H31A	0.6239	0.9312	0.9712	0.047*
H31B	0.5545	0.9211	0.8915	0.047*
C32	0.6960 (5)	0.8007 (2)	1.00139 (19)	0.0410 (11)
H32A	0.6439	0.8133	1.0419	0.049*
H32B	0.7852	0.8253	1.0091	0.049*
C33	0.7122 (5)	0.7179 (3)	0.9960 (2)	0.0458 (12)
H33A	0.7675	0.6991	1.0387	0.055*
H33B	0.6228	0.6934	0.9941	0.055*
Li1	0.7127 (7)	0.7726 (3)	0.8523 (3)	0.0278 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.02406 (13)	0.01671 (12)	0.01436 (11)	0.00045 (11)	−0.00054 (8)	−0.00026 (10)
O1	0.0362 (17)	0.0370 (15)	0.0244 (14)	−0.0082 (13)	−0.0093 (12)	0.0053 (12)
O2	0.0389 (17)	0.0315 (15)	0.0302 (14)	−0.0023 (13)	0.0007 (13)	−0.0025 (12)
O3	0.0337 (15)	0.0291 (14)	0.0247 (13)	−0.0079 (12)	0.0034 (11)	−0.0044 (11)
O4	0.0347 (16)	0.0370 (16)	0.0213 (13)	−0.0083 (13)	0.0008 (12)	−0.0036 (12)
N1	0.0259 (17)	0.0167 (14)	0.0134 (14)	−0.0006 (12)	−0.0010 (12)	−0.0006 (11)
N2	0.0271 (17)	0.0167 (15)	0.0190 (14)	−0.0017 (12)	0.0050 (13)	−0.0030 (12)
C1	0.025 (2)	0.0235 (18)	0.0161 (17)	0.0013 (16)	−0.0060 (15)	−0.0011 (15)
C2	0.0216 (18)	0.0272 (19)	0.0143 (15)	−0.0012 (16)	−0.0047 (13)	0.0016 (15)
C3	0.030 (2)	0.0181 (18)	0.0182 (17)	−0.0015 (15)	−0.0031 (16)	−0.0018 (14)
C4	0.0253 (19)	0.0199 (18)	0.0145 (15)	0.0028 (16)	−0.0033 (14)	0.0011 (14)
C5	0.029 (2)	0.0232 (18)	0.0164 (17)	0.0020 (16)	−0.0016 (15)	−0.0038 (14)
C6	0.030 (2)	0.038 (2)	0.0213 (19)	0.0017 (17)	0.0049 (16)	−0.0022 (16)
C7	0.030 (2)	0.032 (2)	0.029 (2)	−0.0108 (17)	0.0036 (18)	0.0006 (17)
C8	0.034 (2)	0.0197 (19)	0.0250 (19)	−0.0028 (16)	−0.0008 (17)	−0.0059 (15)
C9	0.026 (2)	0.0186 (17)	0.0131 (16)	0.0013 (15)	−0.0067 (14)	−0.0005 (13)
C10	0.031 (2)	0.0213 (18)	0.0168 (17)	0.0023 (16)	−0.0039 (15)	0.0013 (14)
C11	0.033 (2)	0.0183 (18)	0.0184 (17)	0.0011 (16)	−0.0029 (16)	−0.0046 (14)
C12	0.026 (2)	0.0223 (19)	0.0206 (18)	0.0024 (16)	0.0031 (16)	−0.0038 (15)
C13	0.028 (2)	0.027 (2)	0.0199 (17)	−0.0024 (16)	−0.0001 (15)	−0.0042 (15)
C14	0.033 (2)	0.0181 (18)	0.0190 (17)	0.0004 (16)	0.0139 (16)	−0.0018 (14)
C15	0.033 (2)	0.0246 (19)	0.0195 (18)	0.0022 (17)	0.0120 (16)	0.0016 (15)
C16	0.040 (3)	0.029 (2)	0.032 (2)	0.0072 (19)	0.0117 (19)	0.0048 (17)
C17	0.056 (3)	0.023 (2)	0.039 (2)	−0.007 (2)	0.025 (2)	0.0043 (18)
C18	0.039 (3)	0.029 (2)	0.032 (2)	−0.0115 (18)	0.0089 (19)	−0.0018 (17)
C19	0.029 (2)	0.0254 (19)	0.0222 (18)	−0.0050 (16)	0.0121 (16)	−0.0064 (15)
C20	0.030 (2)	0.027 (2)	0.0251 (19)	0.0017 (17)	0.0044 (16)	0.0071 (16)
C21	0.043 (3)	0.061 (3)	0.028 (2)	−0.002 (2)	0.002 (2)	0.007 (2)
C22	0.039 (3)	0.037 (2)	0.044 (3)	0.005 (2)	0.012 (2)	0.007 (2)
C23	0.029 (2)	0.025 (2)	0.031 (2)	−0.0057 (16)	0.0043 (18)	−0.0043 (15)
C24	0.042 (3)	0.044 (3)	0.031 (2)	−0.005 (2)	0.0024 (19)	−0.0105 (19)
C25	0.040 (3)	0.039 (2)	0.047 (3)	−0.006 (2)	0.012 (2)	−0.009 (2)
C26	0.041 (3)	0.047 (3)	0.044 (3)	−0.003 (2)	−0.012 (2)	0.011 (2)
C27	0.043 (3)	0.038 (2)	0.053 (3)	0.006 (2)	−0.008 (2)	−0.001 (2)
C28	0.036 (3)	0.042 (3)	0.043 (2)	−0.011 (2)	0.007 (2)	−0.007 (2)
C29	0.040 (2)	0.031 (2)	0.034 (2)	−0.0124 (19)	0.0101 (19)	0.0029 (18)
C30	0.045 (3)	0.029 (2)	0.035 (2)	−0.0048 (19)	0.010 (2)	−0.0086 (18)
C31	0.044 (3)	0.034 (2)	0.040 (2)	−0.002 (2)	0.008 (2)	−0.0114 (19)
C32	0.048 (3)	0.059 (3)	0.0156 (19)	−0.016 (2)	0.0013 (18)	−0.0004 (19)
C33	0.057 (3)	0.061 (3)	0.017 (2)	−0.014 (2)	−0.004 (2)	0.006 (2)
Li1	0.038 (4)	0.028 (3)	0.017 (3)	−0.005 (3)	−0.004 (3)	0.000 (3)

Geometric parameters (Å, º)

Sn1—N1	2.157 (3)	C15—C16	1.398 (5)
Sn1—N2	2.089 (3)	C15—C20	1.515 (5)
O1—C26	1.422 (5)	C16—H16	0.9500
O1—C33	1.430 (5)	C16—C17	1.386 (6)
O1—Li1	2.068 (6)	C17—H17	0.9500
O2—C27	1.438 (5)	C17—C18	1.371 (6)
O2—C28	1.430 (5)	C18—H18	0.9500
O2—Li1	2.123 (7)	C18—C19	1.395 (5)
O3—C29	1.435 (4)	C19—C23	1.521 (5)
O3—C30	1.437 (4)	C20—H20	1.0000
O3—Li1	2.090 (6)	C20—C21	1.548 (5)
O4—C31	1.431 (5)	C20—C22	1.526 (5)
O4—C32	1.432 (4)	C21—H21A	0.9800
O4—Li1	2.091 (7)	C21—H21B	0.9800
N1—C11	1.470 (4)	C21—H21C	0.9800
N1—C12	1.471 (4)	C22—H22A	0.9800
N1—Li1	2.043 (7)	C22—H22B	0.9800
N2—C13	1.463 (4)	C22—H22C	0.9800
N2—C14	1.430 (4)	C23—H23	1.0000
C1—C2	1.422 (5)	C23—C24	1.540 (5)
C1—C9	1.420 (5)	C23—C25	1.521 (5)
C1—C10	1.508 (5)	C24—H24A	0.9800
C2—H2	0.9500	C24—H24B	0.9800
C2—C3	1.408 (5)	C24—H24C	0.9800
C3—H3	0.9500	C25—H25A	0.9800
C3—C4	1.411 (5)	C25—H25B	0.9800
C4—C5	1.411 (5)	C25—H25C	0.9800
C4—C9	1.452 (4)	C26—H26A	0.9900
C5—H5	0.9500	C26—H26B	0.9900
C5—C6	1.374 (5)	C26—C27	1.486 (6)
C6—H6	0.9500	C27—H27A	0.9900
C6—C7	1.418 (5)	C27—H27B	0.9900
C7—H7	0.9500	C28—H28A	0.9900
C7—C8	1.367 (5)	C28—H28B	0.9900
C8—H8	0.9500	C28—C29	1.504 (6)
C8—C9	1.400 (5)	C29—H29A	0.9900
C10—H10A	0.9900	C29—H29B	0.9900
C10—H10B	0.9900	C30—H30A	0.9900
C10—C11	1.542 (5)	C30—H30B	0.9900
C11—H11A	0.9900	C30—C31	1.489 (5)
C11—H11B	0.9900	C31—H31A	0.9900
C12—H12A	0.9900	C31—H31B	0.9900
C12—H12B	0.9900	C32—H32A	0.9900
C12—C13	1.517 (5)	C32—H32B	0.9900
C13—H13A	0.9900	C32—C33	1.487 (6)
C13—H13B	0.9900	C33—H33A	0.9900
C14—C15	1.412 (5)	C33—H33B	0.9900
C14—C19	1.410 (5)
N2—Sn1—N1	79.49 (10)	C15—C20—C22	112.1 (3)
C26—O1—C33	114.4 (3)	C21—C20—H20	107.5
C26—O1—Li1	110.9 (3)	C22—C20—H20	107.5
C33—O1—Li1	109.3 (3)	C22—C20—C21	109.6 (3)
C27—O2—Li1	107.4 (3)	C20—C21—H21A	109.5
C28—O2—C27	114.2 (3)	C20—C21—H21B	109.5
C28—O2—Li1	109.4 (3)	C20—C21—H21C	109.5
C29—O3—C30	114.0 (3)	H21A—C21—H21B	109.5
C29—O3—Li1	110.8 (3)	H21A—C21—H21C	109.5
C30—O3—Li1	109.9 (3)	H21B—C21—H21C	109.5
C31—O4—C32	113.9 (3)	C20—C22—H22A	109.5
C31—O4—Li1	108.6 (3)	C20—C22—H22B	109.5
C32—O4—Li1	107.8 (3)	C20—C22—H22C	109.5
C11—N1—Sn1	112.15 (19)	H22A—C22—H22B	109.5
C11—N1—C12	111.9 (3)	H22A—C22—H22C	109.5
C11—N1—Li1	100.8 (3)	H22B—C22—H22C	109.5
C12—N1—Sn1	108.64 (19)	C19—C23—H23	107.7
C12—N1—Li1	113.1 (3)	C19—C23—C24	111.7 (3)
Li1—N1—Sn1	110.2 (2)	C19—C23—C25	111.5 (3)
C13—N2—Sn1	115.1 (2)	C24—C23—H23	107.7
C14—N2—Sn1	127.8 (2)	C25—C23—H23	107.7
C14—N2—C13	115.8 (3)	C25—C23—C24	110.4 (3)
C2—C1—C10	127.4 (3)	C23—C24—H24A	109.5
C9—C1—C2	106.8 (3)	C23—C24—H24B	109.5
C9—C1—C10	125.7 (3)	C23—C24—H24C	109.5
C1—C2—H2	125.1	H24A—C24—H24B	109.5
C3—C2—C1	109.8 (3)	H24A—C24—H24C	109.5
C3—C2—H2	125.1	H24B—C24—H24C	109.5
C2—C3—H3	126.0	C23—C25—H25A	109.5
C2—C3—C4	107.9 (3)	C23—C25—H25B	109.5
C4—C3—H3	126.0	C23—C25—H25C	109.5
C3—C4—C9	107.5 (3)	H25A—C25—H25B	109.5
C5—C4—C3	133.8 (3)	H25A—C25—H25C	109.5
C5—C4—C9	118.7 (3)	H25B—C25—H25C	109.5
C4—C5—H5	119.9	O1—C26—H26A	110.3
C6—C5—C4	120.1 (3)	O1—C26—H26B	110.3
C6—C5—H5	119.9	O1—C26—C27	107.0 (3)
C5—C6—H6	119.6	H26A—C26—H26B	108.6
C5—C6—C7	120.8 (3)	C27—C26—H26A	110.3
C7—C6—H6	119.6	C27—C26—H26B	110.3
C6—C7—H7	119.8	O2—C27—C26	111.0 (4)
C8—C7—C6	120.5 (3)	O2—C27—H27A	109.4
C8—C7—H7	119.8	O2—C27—H27B	109.4
C7—C8—H8	119.7	C26—C27—H27A	109.4
C7—C8—C9	120.5 (3)	C26—C27—H27B	109.4
C9—C8—H8	119.7	H27A—C27—H27B	108.0
C1—C9—C4	108.0 (3)	O2—C28—H28A	110.5
C8—C9—C1	132.5 (3)	O2—C28—H28B	110.5
C8—C9—C4	119.4 (3)	O2—C28—C29	106.0 (3)
C1—C10—H10A	108.9	H28A—C28—H28B	108.7
C1—C10—H10B	108.9	C29—C28—H28A	110.5
C1—C10—C11	113.3 (3)	C29—C28—H28B	110.5
H10A—C10—H10B	107.7	O3—C29—C28	110.2 (3)
C11—C10—H10A	108.9	O3—C29—H29A	109.6
C11—C10—H10B	108.9	O3—C29—H29B	109.6
N1—C11—C10	114.7 (3)	C28—C29—H29A	109.6
N1—C11—H11A	108.6	C28—C29—H29B	109.6
N1—C11—H11B	108.6	H29A—C29—H29B	108.1
C10—C11—H11A	108.6	O3—C30—H30A	110.5
C10—C11—H11B	108.6	O3—C30—H30B	110.5
H11A—C11—H11B	107.6	O3—C30—C31	106.2 (3)
N1—C12—H12A	109.6	H30A—C30—H30B	108.7
N1—C12—H12B	109.6	C31—C30—H30A	110.5
N1—C12—C13	110.3 (3)	C31—C30—H30B	110.5
H12A—C12—H12B	108.1	O4—C31—C30	111.3 (3)
C13—C12—H12A	109.6	O4—C31—H31A	109.4
C13—C12—H12B	109.6	O4—C31—H31B	109.4
N2—C13—C12	108.5 (3)	C30—C31—H31A	109.4
N2—C13—H13A	110.0	C30—C31—H31B	109.4
N2—C13—H13B	110.0	H31A—C31—H31B	108.0
C12—C13—H13A	110.0	O4—C32—H32A	110.3
C12—C13—H13B	110.0	O4—C32—H32B	110.3
H13A—C13—H13B	108.4	O4—C32—C33	107.3 (3)
C15—C14—N2	121.0 (3)	H32A—C32—H32B	108.5
C19—C14—N2	119.3 (3)	C33—C32—H32A	110.3
C19—C14—C15	119.7 (3)	C33—C32—H32B	110.3
C14—C15—C20	122.3 (3)	O1—C33—C32	110.6 (3)
C16—C15—C14	118.6 (4)	O1—C33—H33A	109.5
C16—C15—C20	119.1 (3)	O1—C33—H33B	109.5
C15—C16—H16	119.4	C32—C33—H33A	109.5
C17—C16—C15	121.3 (4)	C32—C33—H33B	109.5
C17—C16—H16	119.4	H33A—C33—H33B	108.1
C16—C17—H17	120.1	O1—Li1—O2	80.6 (2)
C18—C17—C16	119.9 (4)	O1—Li1—O3	131.0 (3)
C18—C17—H17	120.1	O1—Li1—O4	81.4 (2)
C17—C18—H18	119.5	O3—Li1—O2	79.5 (2)
C17—C18—C19	121.0 (4)	O3—Li1—O4	80.7 (2)
C19—C18—H18	119.5	O4—Li1—O2	133.3 (3)
C14—C19—C23	121.7 (3)	N1—Li1—O1	114.9 (3)
C18—C19—C14	119.4 (4)	N1—Li1—O2	116.7 (3)
C18—C19—C23	118.9 (3)	N1—Li1—O3	114.1 (3)
C15—C20—H20	107.5	N1—Li1—O4	110.0 (3)
C15—C20—C21	112.4 (3)
Sn1—N1—C11—C10	54.6 (3)	C13—N2—C14—C15	−92.8 (4)
Sn1—N1—C12—C13	41.9 (3)	C13—N2—C14—C19	88.4 (4)
Sn1—N2—C13—C12	27.7 (3)	C14—N2—C13—C12	−164.2 (3)
Sn1—N2—C14—C15	73.5 (4)	C14—C15—C16—C17	−0.4 (5)
Sn1—N2—C14—C19	−105.3 (3)	C14—C15—C20—C21	126.3 (4)
O1—C26—C27—O2	54.0 (5)	C14—C15—C20—C22	−109.8 (4)
O2—C28—C29—O3	53.8 (4)	C14—C19—C23—C24	118.9 (4)
O3—C30—C31—O4	54.0 (4)	C14—C19—C23—C25	−117.1 (4)
O4—C32—C33—O1	54.1 (5)	C15—C14—C19—C18	−4.0 (5)
N1—C12—C13—N2	−45.8 (4)	C15—C14—C19—C23	175.6 (3)
N2—C14—C15—C16	−175.5 (3)	C15—C16—C17—C18	−2.0 (6)
N2—C14—C15—C20	2.8 (5)	C16—C15—C20—C21	−55.4 (4)
N2—C14—C19—C18	174.8 (3)	C16—C15—C20—C22	68.5 (4)
N2—C14—C19—C23	−5.6 (5)	C16—C17—C18—C19	1.3 (6)
C1—C2—C3—C4	0.0 (4)	C17—C18—C19—C14	1.7 (5)
C1—C10—C11—N1	−54.3 (4)	C17—C18—C19—C23	−177.9 (3)
C2—C1—C9—C4	0.6 (4)	C18—C19—C23—C24	−61.6 (4)
C2—C1—C9—C8	177.3 (4)	C18—C19—C23—C25	62.4 (4)
C2—C1—C10—C11	102.2 (4)	C19—C14—C15—C16	3.3 (5)
C2—C3—C4—C5	−179.4 (3)	C19—C14—C15—C20	−178.4 (3)
C2—C3—C4—C9	0.4 (4)	C20—C15—C16—C17	−178.7 (3)
C3—C4—C5—C6	177.9 (4)	C26—O1—C33—C32	90.1 (4)
C3—C4—C9—C1	−0.6 (4)	C27—O2—C28—C29	−166.0 (3)
C3—C4—C9—C8	−177.8 (3)	C28—O2—C27—C26	83.4 (4)
C4—C5—C6—C7	0.5 (5)	C29—O3—C30—C31	−167.3 (3)
C5—C4—C9—C1	179.2 (3)	C30—O3—C29—C28	89.4 (4)
C5—C4—C9—C8	2.0 (5)	C31—O4—C32—C33	−165.3 (3)
C5—C6—C7—C8	0.8 (6)	C32—O4—C31—C30	82.2 (4)
C6—C7—C8—C9	−0.6 (6)	C33—O1—C26—C27	−166.2 (3)
C7—C8—C9—C1	−177.1 (4)	Li1—O1—C26—C27	−42.0 (4)
C7—C8—C9—C4	−0.8 (5)	Li1—O1—C33—C32	−35.0 (4)
C9—C1—C2—C3	−0.4 (4)	Li1—O2—C27—C26	−38.1 (4)
C9—C1—C10—C11	−81.5 (4)	Li1—O2—C28—C29	−45.6 (4)
C9—C4—C5—C6	−1.9 (5)	Li1—O3—C29—C28	−35.1 (4)
C10—C1—C2—C3	176.5 (3)	Li1—O3—C30—C31	−42.3 (4)
C10—C1—C9—C4	−176.4 (3)	Li1—O4—C31—C30	−37.9 (4)
C10—C1—C9—C8	0.3 (6)	Li1—O4—C32—C33	−44.7 (4)
C11—N1—C12—C13	166.3 (3)	Li1—N1—C11—C10	171.8 (3)
C12—N1—C11—C10	−67.8 (4)	Li1—N1—C12—C13	−80.7 (3)