Two isostructural triboluminescent lanthanide complexes

(4-Di­methyl­amino­pyridine)­tris(2,2,6,6-tetra­methyl­heptane-3,5-dionato)­terbium(III), [Tb(C₁₁H₁₉O₂)₃(C₇H₁₀N₂)], and its samarium analogue, [Sm(C₁₁H₁₉O₂)₃(C₇H₁₀N₂)], are isostructural. Their polar space group is consistent with observed second harmonic generation and with the involvement of piezoelectric charging in their intense triboluminescence properties, which are of interest for the development of damage sensors in composite materials. The metals display irregular seven-coordination by one substituted pyridine and three chelating diketonate ligands, bond lengths to Tb being shorter than those to Sm.

Computing details

For both compounds, data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1994); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

(I) Tris(1,3-di-tert-butyl-propane-1,3-dionato)(4-dimethylaminopyridine)terbium(III)

Crystal data

[Tb(C11H19O2)3(C7H10N2)]	F(000) = 868
Mr = 830.88	Dx = 1.285 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.9465 (11) Å	Cell parameters from 5819 reflections
b = 18.972 (2) Å	θ = 2.5–28.6°
c = 11.0469 (12) Å	µ = 1.69 mm^−1
β = 110.643 (2)°	T = 160 K
V = 2146.9 (4) Å^3	Prism, colourless
Z = 2	0.40 × 0.25 × 0.18 mm

Data collection

Siemens SMART CCD diffractometer	9868 independent reflections
Radiation source: fine-focus sealed tube	9418 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 8.192 pixels mm^-1	θmax = 28.7°, θmin = 2.0°
ω rotation with narrow frames scans	h = −14→14
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	k = −24→25
Tmin = 0.551, Tmax = 0.751	l = −14→14
18460 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.029	w = 1/[σ^2(Fo^2) + (0.014P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.054	(Δ/σ)max = 0.001
S = 1.19	Δρmax = 1.24 e Å^−3
9868 reflections	Δρmin = −2.54 e Å^−3
463 parameters	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.00062 (18)
Primary atom site location: isostructural with Sm complex	Absolute structure: Flack (1983), 4588 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.019 (7)

Special details

Experimental. Each data collection nominally covered over a hemisphere of reciprocal space, by a combination of three sets of exposures; each set had a different φ angle for the crystal and each exposure covered 0.3° in ω.

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

	x	y	z	Uiso*/Ueq
Tb	0.234803 (11)	0.250139 (13)	0.192346 (11)	0.02199 (4)
N1	0.2711 (3)	0.29692 (14)	0.4166 (3)	0.0282 (6)
N2	0.3236 (3)	0.37410 (18)	0.7883 (3)	0.0420 (8)
O1	0.04500 (17)	0.2548 (2)	0.01499 (18)	0.0284 (4)
O2	0.1643 (2)	0.36512 (12)	0.1658 (2)	0.0308 (5)
O3	0.3726 (2)	0.16377 (12)	0.3102 (2)	0.0312 (5)
O4	0.1082 (2)	0.17409 (12)	0.2622 (2)	0.0304 (5)
O5	0.4348 (2)	0.30107 (11)	0.2167 (2)	0.0285 (5)
O6	0.3003 (2)	0.20348 (12)	0.0347 (2)	0.0297 (5)
C1	0.3895 (3)	0.3116 (2)	0.5031 (3)	0.0377 (8)
H1A	0.4633	0.3034	0.4787	0.045*
C2	0.4107 (4)	0.3378 (2)	0.6245 (3)	0.0422 (9)
H2A	0.4973	0.3476	0.6806	0.051*
C3	0.3059 (3)	0.35034 (17)	0.6669 (3)	0.0308 (7)
C4	0.1818 (3)	0.3356 (2)	0.5753 (3)	0.0379 (8)
H4A	0.1056	0.3434	0.5958	0.046*
C5	0.1719 (3)	0.3099 (2)	0.4561 (3)	0.0386 (8)
H5A	0.0866	0.3005	0.3966	0.046*
C6	0.4544 (5)	0.3849 (2)	0.8807 (4)	0.0530 (11)
H6A	0.5052	0.4126	0.8403	0.079*
H6B	0.4966	0.3391	0.9080	0.079*
H6C	0.4497	0.4102	0.9562	0.079*
C7	0.2182 (5)	0.3725 (3)	0.8395 (4)	0.0581 (12)
H7A	0.1884	0.3239	0.8400	0.087*
H7B	0.1456	0.4016	0.7851	0.087*
H7C	0.2496	0.3911	0.9280	0.087*
C8	−0.0301 (3)	0.30107 (17)	−0.0536 (3)	0.0239 (6)
C9	−0.0212 (3)	0.37271 (16)	−0.0228 (3)	0.0249 (6)
H9A	−0.0835	0.4038	−0.0792	0.030*
C10	0.0742 (3)	0.40111 (16)	0.0861 (3)	0.0231 (6)
C11	−0.1374 (3)	0.27270 (15)	−0.1765 (3)	0.0276 (8)
C12	−0.2172 (4)	0.3308 (2)	−0.2653 (4)	0.0496 (10)
H12A	−0.2621	0.3587	−0.2190	0.074*
H12B	−0.2817	0.3096	−0.3422	0.074*
H12C	−0.1589	0.3615	−0.2915	0.074*
C13	−0.2270 (3)	0.2263 (2)	−0.1309 (4)	0.0450 (10)
H13A	−0.2688	0.2551	−0.0830	0.067*
H13B	−0.1755	0.1889	−0.0745	0.067*
H13C	−0.2941	0.2051	−0.2061	0.067*
C14	−0.0725 (3)	0.22777 (19)	−0.2518 (3)	0.0387 (9)
H14A	−0.0166	0.2577	−0.2826	0.058*
H14B	−0.1399	0.2059	−0.3259	0.058*
H14C	−0.0196	0.1910	−0.1951	0.058*
C15	0.0775 (3)	0.48064 (17)	0.1174 (3)	0.0299 (7)
C16	0.0570 (5)	0.4883 (2)	0.2466 (4)	0.0533 (11)
H16A	0.1231	0.4607	0.3129	0.080*
H16B	−0.0302	0.4710	0.2378	0.080*
H16C	0.0647	0.5380	0.2721	0.080*
C17	−0.0267 (4)	0.52367 (18)	0.0129 (4)	0.0450 (10)
H17A	−0.0167	0.5164	−0.0709	0.067*
H17B	−0.0160	0.5738	0.0355	0.067*
H17C	−0.1138	0.5082	0.0078	0.067*
C18	0.2135 (3)	0.50836 (18)	0.1298 (4)	0.0389 (8)
H18A	0.2806	0.4802	0.1940	0.058*
H18B	0.2216	0.5578	0.1574	0.058*
H18C	0.2248	0.5048	0.0459	0.058*
C19	0.3651 (3)	0.11003 (17)	0.3757 (3)	0.0279 (7)
C20	0.2496 (3)	0.08742 (18)	0.3903 (3)	0.0333 (8)
H20A	0.2539	0.0466	0.4415	0.040*
C21	0.1283 (3)	0.12008 (17)	0.3355 (3)	0.0278 (7)
C22	0.4950 (3)	0.07039 (18)	0.4393 (3)	0.0341 (8)
C23	0.5451 (5)	0.0503 (3)	0.3320 (5)	0.0632 (13)
H23A	0.4796	0.0214	0.2676	0.095*
H23B	0.6263	0.0234	0.3686	0.095*
H23C	0.5618	0.0931	0.2907	0.095*
C24	0.4835 (5)	0.0052 (3)	0.5162 (5)	0.0447 (12)
H24A	0.4263	−0.0295	0.4573	0.067*
H24B	0.4465	0.0187	0.5817	0.067*
H24C	0.5702	−0.0155	0.5586	0.067*
C25	0.5902 (4)	0.1218 (2)	0.5338 (4)	0.0584 (12)
H25A	0.5594	0.1325	0.6049	0.088*
H25B	0.5949	0.1655	0.4881	0.088*
H25C	0.6771	0.1003	0.5684	0.088*
C26	0.0100 (3)	0.09325 (19)	0.3666 (3)	0.0341 (8)
C27	−0.1148 (4)	0.1050 (3)	0.2509 (4)	0.0549 (11)
H27A	−0.1144	0.0746	0.1794	0.082*
H27B	−0.1197	0.1545	0.2238	0.082*
H27C	−0.1905	0.0936	0.2750	0.082*
C28	0.0020 (4)	0.1369 (3)	0.4794 (4)	0.0631 (13)
H28A	0.0818	0.1302	0.5548	0.095*
H28B	−0.0737	0.1217	0.5006	0.095*
H28C	−0.0074	0.1868	0.4552	0.095*
C29	0.0207 (4)	0.0152 (2)	0.4048 (6)	0.0728 (16)
H29A	0.0906	0.0091	0.4889	0.109*
H29B	0.0406	−0.0127	0.3394	0.109*
H29C	−0.0622	−0.0008	0.4107	0.109*
C30	0.5305 (3)	0.28278 (16)	0.1835 (3)	0.0246 (6)
C31	0.5233 (3)	0.22901 (15)	0.0946 (3)	0.0273 (7)
H31A	0.6016	0.2170	0.0808	0.033*
C32	0.4112 (3)	0.19171 (16)	0.0247 (3)	0.0244 (6)
C33	0.6596 (3)	0.32317 (18)	0.2516 (3)	0.0319 (7)
C34	0.7546 (3)	0.3215 (2)	0.1777 (4)	0.0436 (9)
H34A	0.7828	0.2729	0.1729	0.065*
H34B	0.8309	0.3508	0.2230	0.065*
H34C	0.7110	0.3399	0.0901	0.065*
C35	0.6278 (4)	0.3992 (2)	0.2706 (6)	0.0692 (15)
H35A	0.5914	0.4225	0.1863	0.104*
H35B	0.7076	0.4237	0.3237	0.104*
H35C	0.5638	0.4007	0.3142	0.104*
C36	0.7238 (4)	0.2869 (3)	0.3812 (4)	0.0669 (14)
H36A	0.7379	0.2370	0.3671	0.100*
H36B	0.6671	0.2909	0.4325	0.100*
H36C	0.8079	0.3095	0.4277	0.100*
C37	0.4114 (3)	0.13624 (18)	−0.0759 (3)	0.0292 (7)
C38	0.3077 (4)	0.0810 (2)	−0.0861 (6)	0.0684 (15)
H38A	0.2223	0.1039	−0.1086	0.103*
H38B	0.3286	0.0567	−0.0029	0.103*
H38C	0.3053	0.0467	−0.1533	0.103*
C39	0.3779 (5)	0.1753 (3)	−0.2060 (4)	0.0581 (12)
H39A	0.4455	0.2105	−0.1995	0.087*
H39B	0.2933	0.1989	−0.2269	0.087*
H39C	0.3735	0.1414	−0.2744	0.087*
C40	0.5428 (4)	0.0989 (2)	−0.0438 (4)	0.0444 (9)
H40A	0.6092	0.1330	−0.0460	0.067*
H40B	0.5352	0.0616	−0.1074	0.067*
H40C	0.5682	0.0781	0.0428	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Tb	0.02261 (6)	0.02369 (6)	0.01996 (6)	0.00463 (11)	0.00789 (4)	0.00079 (12)
N1	0.0332 (15)	0.0281 (14)	0.0247 (14)	0.0051 (11)	0.0119 (12)	0.0031 (11)
N2	0.053 (2)	0.0443 (19)	0.0310 (17)	−0.0052 (16)	0.0182 (15)	−0.0112 (14)
O1	0.0297 (9)	0.0226 (11)	0.0288 (9)	−0.0001 (16)	0.0053 (7)	−0.0046 (17)
O2	0.0306 (12)	0.0264 (12)	0.0271 (12)	0.0015 (9)	−0.0001 (10)	−0.0033 (9)
O3	0.0262 (11)	0.0339 (13)	0.0357 (13)	0.0052 (9)	0.0139 (10)	0.0108 (10)
O4	0.0239 (11)	0.0324 (13)	0.0343 (13)	0.0002 (9)	0.0095 (10)	0.0036 (10)
O5	0.0300 (12)	0.0269 (12)	0.0320 (12)	−0.0009 (9)	0.0151 (10)	−0.0035 (10)
O6	0.0243 (11)	0.0397 (13)	0.0262 (12)	0.0005 (9)	0.0104 (9)	−0.0086 (10)
C1	0.0302 (18)	0.059 (2)	0.0272 (18)	−0.0024 (16)	0.0138 (15)	−0.0042 (17)
C2	0.0335 (19)	0.064 (3)	0.0297 (19)	−0.0125 (18)	0.0120 (15)	−0.0074 (18)
C3	0.0413 (19)	0.0283 (17)	0.0251 (17)	−0.0041 (14)	0.0145 (15)	−0.0008 (13)
C4	0.0342 (19)	0.053 (2)	0.0310 (19)	0.0091 (16)	0.0163 (16)	−0.0010 (17)
C5	0.0242 (17)	0.056 (2)	0.0307 (19)	0.0025 (16)	0.0039 (14)	−0.0042 (17)
C6	0.068 (3)	0.058 (3)	0.028 (2)	−0.013 (2)	0.010 (2)	−0.0081 (19)
C7	0.070 (3)	0.077 (3)	0.035 (2)	0.007 (3)	0.028 (2)	−0.007 (2)
C8	0.0189 (14)	0.0318 (17)	0.0227 (16)	−0.0024 (12)	0.0094 (12)	−0.0016 (13)
C9	0.0215 (15)	0.0279 (16)	0.0241 (16)	0.0041 (12)	0.0066 (12)	0.0003 (13)
C10	0.0234 (15)	0.0259 (16)	0.0238 (16)	0.0011 (12)	0.0130 (12)	−0.0020 (13)
C11	0.0220 (15)	0.037 (2)	0.0201 (15)	−0.0024 (11)	0.0027 (12)	−0.0071 (12)
C12	0.042 (2)	0.055 (3)	0.034 (2)	0.0042 (19)	−0.0081 (17)	−0.0081 (19)
C13	0.0372 (19)	0.060 (3)	0.039 (2)	−0.0220 (16)	0.0150 (16)	−0.0190 (17)
C14	0.0346 (17)	0.050 (3)	0.0318 (18)	−0.0031 (14)	0.0122 (15)	−0.0154 (15)
C15	0.0340 (18)	0.0248 (17)	0.0322 (18)	0.0006 (14)	0.0136 (15)	−0.0054 (14)
C16	0.087 (3)	0.037 (2)	0.049 (3)	−0.005 (2)	0.040 (2)	−0.0136 (19)
C17	0.040 (2)	0.027 (2)	0.063 (3)	0.0064 (15)	0.0118 (19)	0.0011 (18)
C18	0.0343 (19)	0.0271 (18)	0.052 (2)	−0.0050 (14)	0.0103 (17)	−0.0017 (16)
C19	0.0336 (17)	0.0262 (17)	0.0225 (16)	0.0029 (13)	0.0082 (13)	0.0021 (13)
C20	0.0348 (18)	0.0325 (18)	0.0340 (19)	−0.0005 (14)	0.0140 (15)	0.0084 (15)
C21	0.0273 (16)	0.0302 (18)	0.0277 (17)	−0.0074 (13)	0.0121 (13)	−0.0053 (14)
C22	0.0304 (17)	0.0340 (19)	0.0355 (19)	0.0035 (14)	0.0087 (15)	0.0072 (15)
C23	0.064 (3)	0.071 (3)	0.065 (3)	0.040 (2)	0.036 (2)	0.020 (2)
C24	0.041 (3)	0.041 (2)	0.057 (3)	0.0080 (18)	0.0223 (19)	0.021 (2)
C25	0.040 (2)	0.053 (3)	0.061 (3)	−0.0028 (19)	−0.008 (2)	0.013 (2)
C26	0.0341 (18)	0.0377 (19)	0.0352 (19)	−0.0034 (15)	0.0181 (15)	−0.0002 (15)
C27	0.031 (2)	0.084 (3)	0.050 (3)	−0.014 (2)	0.0151 (18)	−0.003 (2)
C28	0.056 (3)	0.097 (4)	0.053 (3)	−0.023 (3)	0.040 (2)	−0.022 (3)
C29	0.052 (3)	0.051 (3)	0.130 (5)	−0.007 (2)	0.051 (3)	0.026 (3)
C30	0.0272 (16)	0.0245 (15)	0.0221 (16)	−0.0020 (12)	0.0089 (13)	0.0034 (12)
C31	0.0284 (15)	0.0264 (18)	0.0316 (17)	−0.0024 (11)	0.0162 (13)	−0.0042 (12)
C32	0.0320 (16)	0.0241 (16)	0.0211 (15)	0.0011 (13)	0.0143 (13)	0.0005 (12)
C33	0.0316 (17)	0.0375 (19)	0.0284 (17)	−0.0072 (14)	0.0129 (14)	−0.0081 (14)
C34	0.0336 (19)	0.056 (2)	0.046 (2)	−0.0176 (17)	0.0200 (17)	−0.0119 (19)
C35	0.046 (2)	0.043 (3)	0.115 (4)	−0.019 (2)	0.024 (3)	−0.043 (3)
C36	0.049 (3)	0.109 (4)	0.032 (2)	−0.029 (2)	0.0016 (19)	0.008 (2)
C37	0.0278 (17)	0.0308 (18)	0.0354 (19)	−0.0062 (14)	0.0190 (15)	−0.0116 (15)
C38	0.060 (3)	0.051 (3)	0.114 (4)	−0.028 (2)	0.056 (3)	−0.041 (3)
C39	0.083 (3)	0.058 (3)	0.031 (2)	0.013 (2)	0.019 (2)	−0.009 (2)
C40	0.040 (2)	0.042 (2)	0.056 (3)	0.0004 (17)	0.022 (2)	−0.0131 (19)

Geometric parameters (Å, º)

Tb—O6	2.282 (2)	C7—H7B	0.980
Tb—O3	2.296 (2)	C7—H7C	0.980
Tb—O2	2.298 (2)	C9—H9A	0.950
Tb—O1	2.3006 (18)	C12—H12A	0.980
Tb—O4	2.313 (2)	C12—H12B	0.980
Tb—O5	2.320 (2)	C12—H12C	0.980
Tb—N1	2.527 (3)	C13—H13A	0.980
N1—C5	1.329 (4)	C13—H13B	0.980
N1—C1	1.340 (4)	C13—H13C	0.980
N2—C3	1.362 (4)	C14—H14A	0.980
N2—C6	1.450 (5)	C14—H14B	0.980
N2—C7	1.454 (5)	C14—H14C	0.980
O1—C8	1.258 (4)	C16—H16A	0.980
O2—C10	1.265 (4)	C16—H16B	0.980
O3—C19	1.269 (4)	C16—H16C	0.980
O4—C21	1.276 (4)	C17—H17A	0.980
O5—C30	1.274 (4)	C17—H17B	0.980
O6—C32	1.278 (3)	C17—H17C	0.980
C1—C2	1.372 (5)	C18—H18A	0.980
C2—C3	1.403 (5)	C18—H18B	0.980
C3—C4	1.406 (5)	C18—H18C	0.980
C4—C5	1.373 (5)	C20—H20A	0.950
C8—C9	1.396 (4)	C23—H23A	0.980
C8—C11	1.546 (4)	C23—H23B	0.980
C9—C10	1.394 (4)	C23—H23C	0.980
C10—C15	1.546 (4)	C24—H24A	0.980
C11—C12	1.529 (5)	C24—H24B	0.980
C11—C14	1.529 (4)	C24—H24C	0.980
C11—C13	1.530 (4)	C25—H25A	0.980
C15—C16	1.528 (5)	C25—H25B	0.980
C15—C18	1.539 (4)	C25—H25C	0.980
C15—C17	1.540 (5)	C27—H27A	0.980
C19—C20	1.398 (4)	C27—H27B	0.980
C19—C22	1.541 (4)	C27—H27C	0.980
C20—C21	1.395 (5)	C28—H28A	0.980
C21—C26	1.539 (4)	C28—H28B	0.980
C22—C23	1.520 (5)	C28—H28C	0.980
C22—C24	1.531 (6)	C29—H29A	0.980
C22—C25	1.537 (5)	C29—H29B	0.980
C26—C27	1.522 (5)	C29—H29C	0.980
C26—C28	1.524 (5)	C31—H31A	0.950
C26—C29	1.534 (5)	C34—H34A	0.980
C30—C31	1.399 (4)	C34—H34B	0.980
C30—C33	1.550 (4)	C34—H34C	0.980
C31—C32	1.391 (4)	C35—H35A	0.980
C32—C37	1.531 (4)	C35—H35B	0.980
C33—C35	1.517 (5)	C35—H35C	0.980
C33—C36	1.519 (5)	C36—H36A	0.980
C33—C34	1.532 (4)	C36—H36B	0.980
C37—C38	1.520 (5)	C36—H36C	0.980
C37—C40	1.528 (5)	C38—H38A	0.980
C37—C39	1.543 (6)	C38—H38B	0.980
C1—H1A	0.950	C38—H38C	0.980
C2—H2A	0.950	C39—H39A	0.980
C4—H4A	0.950	C39—H39B	0.980
C5—H5A	0.950	C39—H39C	0.980
C6—H6A	0.980	C40—H40A	0.980
C6—H6B	0.980	C40—H40B	0.980
C6—H6C	0.980	C40—H40C	0.980
C7—H7A	0.980
O6—Tb—O3	80.54 (8)	H7B—C7—H7C	109.5
O6—Tb—O2	116.90 (8)	C10—C9—H9A	118.2
O3—Tb—O2	150.90 (8)	C8—C9—H9A	118.2
O6—Tb—O1	78.31 (8)	C11—C12—H12A	109.5
O3—Tb—O1	136.55 (12)	C11—C12—H12B	109.5
O2—Tb—O1	72.12 (12)	H12A—C12—H12B	109.5
O6—Tb—O4	113.49 (8)	C11—C12—H12C	109.5
O3—Tb—O4	73.55 (8)	H12A—C12—H12C	109.5
O2—Tb—O4	114.90 (8)	H12B—C12—H12C	109.5
O1—Tb—O4	80.83 (9)	C11—C13—H13A	109.5
O6—Tb—O5	73.32 (7)	C11—C13—H13B	109.5
O3—Tb—O5	80.03 (8)	H13A—C13—H13B	109.5
O2—Tb—O5	83.12 (8)	C11—C13—H13C	109.5
O1—Tb—O5	127.94 (9)	H13A—C13—H13C	109.5
O4—Tb—O5	150.77 (8)	H13B—C13—H13C	109.5
O6—Tb—N1	154.26 (8)	C11—C14—H14A	109.5
O3—Tb—N1	81.36 (8)	C11—C14—H14B	109.5
O2—Tb—N1	73.83 (8)	H14A—C14—H14B	109.5
O1—Tb—N1	127.16 (9)	C11—C14—H14C	109.5
O4—Tb—N1	78.34 (8)	H14A—C14—H14C	109.5
O5—Tb—N1	85.63 (8)	H14B—C14—H14C	109.5
C5—N1—C1	115.1 (3)	C15—C16—H16A	109.5
C5—N1—Tb	121.5 (2)	C15—C16—H16B	109.5
C1—N1—Tb	123.4 (2)	H16A—C16—H16B	109.5
C3—N2—C6	120.2 (3)	C15—C16—H16C	109.5
C3—N2—C7	121.3 (3)	H16A—C16—H16C	109.5
C6—N2—C7	116.8 (3)	H16B—C16—H16C	109.5
C8—O1—Tb	137.9 (3)	C15—C17—H17A	109.5
C10—O2—Tb	138.2 (2)	C15—C17—H17B	109.5
C19—O3—Tb	137.3 (2)	H17A—C17—H17B	109.5
C21—O4—Tb	136.3 (2)	C15—C17—H17C	109.5
C30—O5—Tb	133.7 (2)	H17A—C17—H17C	109.5
C32—O6—Tb	134.25 (19)	H17B—C17—H17C	109.5
N1—C1—C2	124.1 (3)	C15—C18—H18A	109.5
C1—C2—C3	120.7 (3)	C15—C18—H18B	109.5
N2—C3—C2	122.3 (3)	H18A—C18—H18B	109.5
N2—C3—C4	122.7 (3)	C15—C18—H18C	109.5
C2—C3—C4	115.0 (3)	H18A—C18—H18C	109.5
C5—C4—C3	119.4 (3)	H18B—C18—H18C	109.5
N1—C5—C4	125.7 (3)	C21—C20—H20A	117.4
O1—C8—C9	123.9 (3)	C19—C20—H20A	117.4
O1—C8—C11	114.8 (3)	C22—C23—H23A	109.5
C9—C8—C11	121.3 (3)	C22—C23—H23B	109.5
C10—C9—C8	123.6 (3)	H23A—C23—H23B	109.5
O2—C10—C9	123.7 (3)	C22—C23—H23C	109.5
O2—C10—C15	114.9 (3)	H23A—C23—H23C	109.5
C9—C10—C15	121.4 (3)	H23B—C23—H23C	109.5
C12—C11—C14	108.9 (3)	C22—C24—H24A	109.5
C12—C11—C13	109.8 (3)	C22—C24—H24B	109.5
C14—C11—C13	109.4 (3)	H24A—C24—H24B	109.5
C12—C11—C8	113.4 (3)	C22—C24—H24C	109.5
C14—C11—C8	108.5 (2)	H24A—C24—H24C	109.5
C13—C11—C8	106.7 (2)	H24B—C24—H24C	109.5
C16—C15—C18	109.9 (3)	C22—C25—H25A	109.5
C16—C15—C17	109.6 (3)	C22—C25—H25B	109.5
C18—C15—C17	108.9 (3)	H25A—C25—H25B	109.5
C16—C15—C10	107.6 (3)	C22—C25—H25C	109.5
C18—C15—C10	107.4 (3)	H25A—C25—H25C	109.5
C17—C15—C10	113.4 (3)	H25B—C25—H25C	109.5
O3—C19—C20	123.7 (3)	C26—C27—H27A	109.5
O3—C19—C22	114.7 (3)	C26—C27—H27B	109.5
C20—C19—C22	121.6 (3)	H27A—C27—H27B	109.5
C21—C20—C19	125.1 (3)	C26—C27—H27C	109.5
O4—C21—C20	123.8 (3)	H27A—C27—H27C	109.5
O4—C21—C26	115.9 (3)	H27B—C27—H27C	109.5
C20—C21—C26	120.2 (3)	C26—C28—H28A	109.5
C23—C22—C24	110.6 (3)	C26—C28—H28B	109.5
C23—C22—C25	110.1 (4)	H28A—C28—H28B	109.5
C24—C22—C25	107.8 (4)	C26—C28—H28C	109.5
C23—C22—C19	107.2 (3)	H28A—C28—H28C	109.5
C24—C22—C19	113.8 (3)	H28B—C28—H28C	109.5
C25—C22—C19	107.2 (3)	C26—C29—H29A	109.5
C27—C26—C28	108.3 (3)	C26—C29—H29B	109.5
C27—C26—C29	109.4 (3)	H29A—C29—H29B	109.5
C28—C26—C29	108.7 (4)	C26—C29—H29C	109.5
C27—C26—C21	109.9 (3)	H29A—C29—H29C	109.5
C28—C26—C21	107.4 (3)	H29B—C29—H29C	109.5
C29—C26—C21	113.1 (3)	C32—C31—H31A	117.2
O5—C30—C31	123.5 (3)	C30—C31—H31A	117.2
O5—C30—C33	115.3 (3)	C33—C34—H34A	109.5
C31—C30—C33	121.1 (3)	C33—C34—H34B	109.5
C32—C31—C30	125.5 (3)	H34A—C34—H34B	109.5
O6—C32—C31	122.9 (3)	C33—C34—H34C	109.5
O6—C32—C37	115.3 (3)	H34A—C34—H34C	109.5
C31—C32—C37	121.7 (3)	H34B—C34—H34C	109.5
C35—C33—C36	110.6 (4)	C33—C35—H35A	109.5
C35—C33—C34	109.0 (3)	C33—C35—H35B	109.5
C36—C33—C34	108.5 (3)	H35A—C35—H35B	109.5
C35—C33—C30	108.8 (3)	C33—C35—H35C	109.5
C36—C33—C30	105.8 (3)	H35A—C35—H35C	109.5
C34—C33—C30	114.0 (3)	H35B—C35—H35C	109.5
C38—C37—C40	108.3 (3)	C33—C36—H36A	109.5
C38—C37—C32	109.6 (3)	C33—C36—H36B	109.5
C40—C37—C32	113.1 (3)	H36A—C36—H36B	109.5
C38—C37—C39	109.7 (4)	C33—C36—H36C	109.5
C40—C37—C39	109.6 (3)	H36A—C36—H36C	109.5
C32—C37—C39	106.6 (3)	H36B—C36—H36C	109.5
N1—C1—H1A	118.0	C37—C38—H38A	109.5
C2—C1—H1A	118.0	C37—C38—H38B	109.5
C1—C2—H2A	119.6	H38A—C38—H38B	109.5
C3—C2—H2A	119.6	C37—C38—H38C	109.5
C5—C4—H4A	120.3	H38A—C38—H38C	109.5
C3—C4—H4A	120.3	H38B—C38—H38C	109.5
N1—C5—H5A	117.1	C37—C39—H39A	109.5
C4—C5—H5A	117.1	C37—C39—H39B	109.5
N2—C6—H6A	109.5	H39A—C39—H39B	109.5
N2—C6—H6B	109.5	C37—C39—H39C	109.5
H6A—C6—H6B	109.5	H39A—C39—H39C	109.5
N2—C6—H6C	109.5	H39B—C39—H39C	109.5
H6A—C6—H6C	109.5	C37—C40—H40A	109.5
H6B—C6—H6C	109.5	C37—C40—H40B	109.5
N2—C7—H7A	109.5	H40A—C40—H40B	109.5
N2—C7—H7B	109.5	C37—C40—H40C	109.5
H7A—C7—H7B	109.5	H40A—C40—H40C	109.5
N2—C7—H7C	109.5	H40B—C40—H40C	109.5
H7A—C7—H7C	109.5

(II) Tris(1,3-di-tert-butyl-propane-1,3-dionato)(4-dimethylaminopyridine)samarium(III)

Crystal data

[Sm(C11H19O2)3(C7H10N2)]	F(000) = 862
Mr = 822.31	Dx = 1.264 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.9846 (5) Å	Cell parameters from 4928 reflections
b = 18.9758 (8) Å	θ = 2.2–27.8°
c = 11.0865 (5) Å	µ = 1.40 mm^−1
β = 110.833 (2)°	T = 160 K
V = 2159.80 (17) Å^3	Prism, colourless
Z = 2	0.50 × 0.50 × 0.25 mm

Data collection

Siemens SMART CCD diffractometer	7953 independent reflections
Radiation source: fine-focus sealed tube	6733 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.192 pixels mm^-1	θmax = 28.8°, θmin = 2.0°
ω rotation with narrow frames scans	h = −14→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	k = −13→25
Tmin = 0.578, Tmax = 0.704	l = −14→15
13396 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.026	w = 1/[σ^2(Fo^2) + (0.0202P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.047	(Δ/σ)max = 0.003
S = 0.94	Δρmax = 0.65 e Å^−3
7953 reflections	Δρmin = −0.49 e Å^−3
463 parameters	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.00091 (13)
Primary atom site location: heavy-atom method	Absolute structure: Flack (1983); 2642 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.007 (7)

Special details

Experimental. Each data collection nominally covered over a hemisphere of reciprocal space, by a combination of three sets of exposures; each set had a different φ angle for the crystal and each exposure covered 0.3° in ω.

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

	x	y	z	Uiso*/Ueq
Sm	0.766607 (13)	0.749890 (12)	0.808759 (12)	0.02455 (4)
N1	0.7285 (3)	0.70142 (15)	0.5810 (3)	0.0313 (6)
N2	0.6769 (3)	0.62563 (19)	0.2101 (3)	0.0430 (8)
O1	0.95876 (18)	0.7439 (3)	0.98822 (18)	0.0313 (6)
O2	0.8407 (2)	0.63324 (12)	0.8362 (2)	0.0330 (5)
O3	0.6282 (2)	0.83801 (13)	0.6886 (2)	0.0339 (6)
O4	0.8919 (2)	0.82766 (13)	0.7351 (2)	0.0331 (6)
O5	0.5631 (2)	0.69905 (12)	0.7858 (2)	0.0305 (5)
O6	0.6981 (2)	0.79663 (13)	0.9679 (2)	0.0314 (6)
C1	0.6107 (3)	0.6881 (2)	0.4943 (3)	0.0420 (10)
H1A	0.5371	0.6975	0.5179	0.050*
C2	0.5888 (3)	0.6616 (2)	0.3723 (3)	0.0427 (10)
H2A	0.5025	0.6514	0.3164	0.051*
C3	0.6938 (3)	0.64958 (19)	0.3306 (3)	0.0331 (8)
C4	0.8163 (3)	0.6634 (2)	0.4220 (3)	0.0402 (9)
H4A	0.8922	0.6552	0.4017	0.048*
C5	0.8277 (3)	0.6887 (2)	0.5412 (3)	0.0402 (9)
H5A	0.9130	0.6979	0.6004	0.048*
C6	0.5458 (4)	0.6151 (3)	0.1170 (4)	0.0565 (13)
H6A	0.4957	0.5860	0.1558	0.085*
H6B	0.5505	0.5914	0.0403	0.085*
H6C	0.5028	0.6609	0.0922	0.085*
C7	0.7816 (4)	0.6271 (3)	0.1601 (4)	0.0576 (12)
H7A	0.8152	0.6752	0.1648	0.086*
H7B	0.7490	0.6113	0.0700	0.086*
H7C	0.8517	0.5956	0.2114	0.086*
C8	1.0332 (3)	0.69689 (19)	1.0569 (3)	0.0254 (7)
C9	1.0235 (3)	0.62531 (18)	1.0254 (3)	0.0270 (7)
H9A	1.0851	0.5941	1.0823	0.032*
C10	0.9297 (3)	0.59684 (18)	0.9163 (3)	0.0248 (7)
C11	1.1398 (3)	0.72441 (18)	1.1800 (3)	0.0322 (8)
C12	1.2181 (4)	0.6657 (2)	1.2689 (3)	0.0526 (11)
H12A	1.2822	0.6866	1.3464	0.079*
H12B	1.2632	0.6377	1.2234	0.079*
H12C	1.1590	0.6353	1.2939	0.079*
C13	1.2314 (3)	0.7704 (2)	1.1361 (3)	0.0485 (14)
H13A	1.2963	0.7926	1.2115	0.073*
H13B	1.1807	0.8069	1.0771	0.073*
H13C	1.2756	0.7410	1.0917	0.073*
C14	1.0760 (3)	0.7706 (2)	1.2541 (3)	0.0409 (12)
H14A	1.1436	0.7920	1.3284	0.061*
H14B	1.0186	0.7416	1.2841	0.061*
H14C	1.0248	0.8078	1.1970	0.061*
C15	0.9265 (3)	0.51740 (19)	0.8853 (3)	0.0324 (8)
C16	0.9480 (4)	0.5102 (2)	0.7555 (4)	0.0545 (11)
H16A	1.0355	0.5268	0.7656	0.082*
H16B	0.8830	0.5385	0.6897	0.082*
H16C	0.9390	0.4606	0.7289	0.082*
C17	1.0288 (4)	0.4747 (2)	0.9891 (4)	0.0461 (10)
H17A	1.0198	0.4830	1.0728	0.069*
H17B	1.1159	0.4891	0.9935	0.069*
H17C	1.0164	0.4244	0.9678	0.069*
C18	0.7902 (3)	0.4893 (2)	0.8711 (4)	0.0416 (9)
H18A	0.7770	0.4939	0.9536	0.062*
H18B	0.7834	0.4396	0.8456	0.062*
H18C	0.7235	0.5166	0.8049	0.062*
C19	0.6347 (3)	0.89161 (19)	0.6234 (3)	0.0314 (8)
C20	0.7501 (3)	0.9149 (2)	0.6077 (3)	0.0345 (8)
H20A	0.7455	0.9559	0.5570	0.041*
C21	0.8714 (3)	0.88129 (19)	0.6624 (3)	0.0304 (8)
C22	0.5052 (3)	0.93128 (19)	0.5589 (3)	0.0351 (8)
C23	0.4567 (4)	0.9520 (3)	0.6676 (4)	0.0654 (14)
H23A	0.3720	0.9755	0.6308	0.098*
H23B	0.5195	0.9842	0.7272	0.098*
H23C	0.4477	0.9097	0.7142	0.098*
C24	0.5150 (6)	0.9970 (4)	0.4826 (5)	0.0483 (14)
H24A	0.4288	1.0186	0.4442	0.072*
H24B	0.5475	0.9836	0.4142	0.072*
H24C	0.5752	1.0308	0.5408	0.072*
C25	0.4092 (4)	0.8801 (2)	0.4671 (4)	0.0596 (12)
H25A	0.3243	0.9031	0.4283	0.089*
H25B	0.4001	0.8383	0.5151	0.089*
H25C	0.4417	0.8660	0.3990	0.089*
C26	0.9889 (3)	0.9086 (2)	0.6295 (3)	0.0391 (9)
C27	1.1135 (4)	0.8983 (3)	0.7459 (4)	0.0588 (13)
H27A	1.1887	0.9113	0.7227	0.088*
H27B	1.1209	0.8488	0.7728	0.088*
H27C	1.1110	0.9282	0.8170	0.088*
C28	0.9962 (4)	0.8630 (3)	0.5189 (4)	0.0639 (14)
H28A	1.0686	0.8790	0.4937	0.096*
H28B	0.9144	0.8670	0.4450	0.096*
H28C	1.0103	0.8137	0.5470	0.096*
C29	0.9768 (4)	0.9858 (3)	0.5884 (5)	0.0765 (16)
H29A	1.0582	1.0014	0.5794	0.115*
H29B	0.9593	1.0146	0.6538	0.115*
H29C	0.9050	0.9911	0.5055	0.115*
C30	0.4675 (3)	0.71808 (17)	0.8178 (3)	0.0270 (7)
C31	0.4752 (3)	0.77199 (16)	0.9065 (3)	0.0288 (8)
H31A	0.3972	0.7845	0.9198	0.035*
C32	0.5879 (3)	0.80875 (18)	0.9770 (3)	0.0263 (7)
C33	0.3385 (3)	0.6783 (2)	0.7486 (3)	0.0318 (8)
C34	0.2423 (3)	0.6803 (2)	0.8221 (4)	0.0494 (11)
H34A	0.2178	0.7292	0.8302	0.074*
H34B	0.2840	0.6599	0.9082	0.074*
H34C	0.1643	0.6530	0.7744	0.074*
C35	0.3674 (4)	0.6026 (2)	0.7280 (5)	0.0722 (15)
H35A	0.4290	0.6008	0.6822	0.108*
H35B	0.2865	0.5787	0.6766	0.108*
H35C	0.4055	0.5790	0.8117	0.108*
C36	0.2751 (4)	0.7151 (3)	0.6195 (3)	0.0690 (16)
H36A	0.3336	0.7131	0.5704	0.104*
H36B	0.2580	0.7645	0.6343	0.104*
H36C	0.1928	0.6916	0.5708	0.104*
C37	0.5876 (3)	0.8649 (2)	1.0769 (4)	0.0334 (9)
C38	0.6888 (5)	0.9199 (3)	1.0852 (6)	0.0757 (16)
H38A	0.6638	0.9458	1.0034	0.113*
H38B	0.7732	0.8971	1.1021	0.113*
H38C	0.6952	0.9528	1.1554	0.113*
C39	0.6207 (5)	0.8258 (3)	1.2060 (4)	0.0634 (13)
H39A	0.5508	0.7924	1.2005	0.095*
H39B	0.6296	0.8598	1.2751	0.095*
H39C	0.7028	0.8001	1.2248	0.095*
C40	0.4568 (4)	0.9016 (2)	1.0466 (5)	0.0546 (12)
H40A	0.4285	0.9210	0.9590	0.082*
H40B	0.4656	0.9398	1.1085	0.082*
H40C	0.3921	0.8676	1.0526	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sm	0.02617 (7)	0.02620 (7)	0.02198 (6)	0.00443 (17)	0.00943 (5)	0.00068 (16)
N1	0.0393 (16)	0.0280 (17)	0.0268 (15)	0.0042 (13)	0.0120 (13)	−0.0015 (12)
N2	0.055 (2)	0.046 (2)	0.0313 (17)	0.0004 (18)	0.0195 (16)	−0.0080 (15)
O1	0.0332 (9)	0.0249 (17)	0.0313 (9)	0.0018 (17)	0.0061 (8)	−0.0020 (16)
O2	0.0323 (12)	0.0263 (14)	0.0331 (13)	0.0017 (11)	0.0027 (10)	−0.0030 (11)
O3	0.0320 (12)	0.0354 (15)	0.0379 (13)	0.0050 (11)	0.0169 (11)	0.0105 (12)
O4	0.0272 (12)	0.0363 (15)	0.0354 (13)	0.0016 (11)	0.0106 (10)	0.0016 (12)
O5	0.0314 (12)	0.0288 (14)	0.0326 (12)	0.0009 (10)	0.0132 (10)	−0.0040 (10)
O6	0.0278 (12)	0.0418 (15)	0.0261 (12)	0.0040 (11)	0.0113 (10)	−0.0086 (10)
C1	0.037 (2)	0.063 (3)	0.0302 (19)	−0.0021 (19)	0.0173 (17)	−0.0027 (19)
C2	0.038 (2)	0.061 (3)	0.0290 (19)	−0.0105 (19)	0.0117 (16)	−0.0062 (18)
C3	0.043 (2)	0.031 (2)	0.0276 (18)	−0.0018 (17)	0.0158 (16)	−0.0005 (15)
C4	0.037 (2)	0.056 (3)	0.034 (2)	0.0106 (19)	0.0204 (17)	−0.0015 (19)
C5	0.0285 (18)	0.057 (3)	0.034 (2)	0.0033 (18)	0.0087 (16)	−0.0029 (18)
C6	0.065 (3)	0.069 (4)	0.028 (2)	−0.014 (3)	0.007 (2)	−0.008 (2)
C7	0.072 (3)	0.072 (4)	0.038 (2)	0.006 (3)	0.030 (2)	−0.009 (2)
C8	0.0239 (16)	0.034 (2)	0.0224 (16)	−0.0015 (15)	0.0125 (13)	−0.0037 (15)
C9	0.0256 (16)	0.030 (2)	0.0251 (17)	0.0066 (15)	0.0082 (14)	0.0013 (14)
C10	0.0250 (16)	0.0289 (19)	0.0254 (16)	0.0010 (14)	0.0151 (14)	−0.0025 (14)
C11	0.0270 (17)	0.041 (2)	0.0238 (16)	−0.0023 (14)	0.0039 (14)	−0.0074 (14)
C12	0.044 (2)	0.063 (3)	0.034 (2)	0.002 (2)	−0.0074 (17)	−0.008 (2)
C13	0.0421 (19)	0.065 (4)	0.0414 (18)	−0.024 (2)	0.0180 (16)	−0.021 (2)
C14	0.0402 (18)	0.050 (3)	0.0318 (17)	−0.0037 (17)	0.0123 (15)	−0.0173 (17)
C15	0.0349 (19)	0.028 (2)	0.037 (2)	0.0032 (16)	0.0162 (16)	−0.0033 (16)
C16	0.091 (3)	0.034 (2)	0.049 (2)	−0.004 (2)	0.039 (2)	−0.0153 (19)
C17	0.047 (2)	0.025 (2)	0.065 (3)	0.0069 (18)	0.017 (2)	0.001 (2)
C18	0.041 (2)	0.025 (2)	0.053 (2)	−0.0090 (17)	0.0098 (17)	−0.0047 (18)
C19	0.0366 (19)	0.027 (2)	0.0289 (18)	0.0000 (16)	0.0100 (15)	−0.0019 (15)
C20	0.0343 (19)	0.036 (2)	0.0353 (19)	0.0017 (16)	0.0147 (16)	0.0096 (16)
C21	0.0348 (19)	0.034 (2)	0.0263 (17)	−0.0034 (16)	0.0152 (15)	−0.0047 (16)
C22	0.0342 (19)	0.031 (2)	0.0373 (19)	0.0047 (16)	0.0087 (16)	0.0087 (16)
C23	0.068 (3)	0.071 (4)	0.068 (3)	0.037 (3)	0.037 (2)	0.022 (3)
C24	0.048 (3)	0.045 (3)	0.053 (3)	0.010 (2)	0.020 (2)	0.020 (3)
C25	0.041 (2)	0.055 (3)	0.063 (3)	0.002 (2)	−0.006 (2)	0.011 (2)
C26	0.038 (2)	0.044 (2)	0.040 (2)	−0.0039 (18)	0.0186 (17)	−0.0036 (18)
C27	0.039 (2)	0.086 (4)	0.054 (3)	−0.016 (2)	0.019 (2)	−0.007 (2)
C28	0.064 (3)	0.090 (4)	0.056 (3)	−0.021 (3)	0.043 (2)	−0.025 (3)
C29	0.059 (3)	0.056 (3)	0.130 (5)	−0.007 (3)	0.053 (3)	0.023 (3)
C30	0.0282 (17)	0.0242 (17)	0.0280 (18)	−0.0024 (14)	0.0094 (15)	0.0045 (14)
C31	0.0293 (17)	0.026 (2)	0.0359 (18)	0.0000 (13)	0.0174 (15)	−0.0033 (14)
C32	0.0343 (18)	0.0233 (18)	0.0260 (17)	−0.0005 (15)	0.0164 (14)	0.0007 (14)
C33	0.0316 (18)	0.040 (2)	0.0277 (17)	−0.0067 (16)	0.0147 (15)	−0.0033 (16)
C34	0.044 (2)	0.062 (3)	0.049 (2)	−0.024 (2)	0.0267 (19)	−0.015 (2)
C35	0.054 (3)	0.046 (3)	0.111 (4)	−0.019 (2)	0.023 (3)	−0.037 (3)
C36	0.052 (3)	0.106 (4)	0.035 (2)	−0.024 (2)	−0.0022 (19)	0.013 (2)
C37	0.0308 (19)	0.035 (2)	0.040 (2)	−0.0071 (17)	0.0194 (17)	−0.0106 (17)
C38	0.076 (3)	0.050 (3)	0.125 (4)	−0.030 (3)	0.065 (3)	−0.046 (3)
C39	0.091 (3)	0.067 (4)	0.031 (2)	0.016 (3)	0.020 (2)	−0.013 (2)
C40	0.051 (3)	0.045 (3)	0.076 (3)	−0.001 (2)	0.034 (2)	−0.021 (2)

Geometric parameters (Å, º)

Sm—O6	2.326 (2)	C7—H7B	0.980
Sm—O1	2.3323 (19)	C7—H7C	0.980
Sm—O3	2.333 (2)	C9—H9A	0.950
Sm—O2	2.341 (2)	C12—H12A	0.980
Sm—O4	2.354 (2)	C12—H12B	0.980
Sm—O5	2.364 (2)	C12—H12C	0.980
Sm—N1	2.578 (3)	C13—H13A	0.980
N1—C1	1.334 (4)	C13—H13B	0.980
N1—C5	1.334 (4)	C13—H13C	0.980
N2—C3	1.359 (4)	C14—H14A	0.980
N2—C7	1.444 (5)	C14—H14B	0.980
N2—C6	1.457 (5)	C14—H14C	0.980
O1—C8	1.265 (5)	C16—H16A	0.980
O2—C10	1.267 (4)	C16—H16B	0.980
O3—C19	1.265 (4)	C16—H16C	0.980
O4—C21	1.268 (4)	C17—H17A	0.980
O5—C30	1.275 (4)	C17—H17B	0.980
O6—C32	1.271 (4)	C17—H17C	0.980
C1—C2	1.383 (5)	C18—H18A	0.980
C2—C3	1.405 (5)	C18—H18B	0.980
C3—C4	1.392 (5)	C18—H18C	0.980
C4—C5	1.370 (5)	C20—H20A	0.950
C8—C9	1.397 (5)	C23—H23A	0.980
C8—C11	1.540 (4)	C23—H23B	0.980
C9—C10	1.389 (4)	C23—H23C	0.980
C10—C15	1.544 (5)	C24—H24A	0.980
C11—C14	1.531 (4)	C24—H24B	0.980
C11—C12	1.532 (5)	C24—H24C	0.980
C11—C13	1.536 (5)	C25—H25A	0.980
C15—C17	1.525 (5)	C25—H25B	0.980
C15—C18	1.544 (4)	C25—H25C	0.980
C15—C16	1.545 (5)	C27—H27A	0.980
C19—C20	1.411 (4)	C27—H27B	0.980
C19—C22	1.542 (5)	C27—H27C	0.980
C20—C21	1.406 (5)	C28—H28A	0.980
C21—C26	1.550 (5)	C28—H28B	0.980
C22—C25	1.525 (5)	C28—H28C	0.980
C22—C23	1.532 (5)	C29—H29A	0.980
C22—C24	1.532 (7)	C29—H29B	0.980
C26—C27	1.523 (5)	C29—H29C	0.980
C26—C28	1.526 (5)	C31—H31A	0.950
C26—C29	1.526 (6)	C34—H34A	0.980
C30—C31	1.401 (4)	C34—H34B	0.980
C30—C33	1.547 (4)	C34—H34C	0.980
C31—C32	1.393 (4)	C35—H35A	0.980
C32—C37	1.539 (5)	C35—H35B	0.980
C33—C35	1.506 (5)	C35—H35C	0.980
C33—C36	1.521 (5)	C36—H36A	0.980
C33—C34	1.547 (4)	C36—H36B	0.980
C37—C38	1.504 (5)	C36—H36C	0.980
C37—C40	1.522 (5)	C38—H38A	0.980
C37—C39	1.537 (6)	C38—H38B	0.980
C1—H1A	0.950	C38—H38C	0.980
C2—H2A	0.950	C39—H39A	0.980
C4—H4A	0.950	C39—H39B	0.980
C5—H5A	0.950	C39—H39C	0.980
C6—H6A	0.980	C40—H40A	0.980
C6—H6B	0.980	C40—H40B	0.980
C6—H6C	0.980	C40—H40C	0.980
C7—H7A	0.980
O6—Sm—O1	79.07 (8)	H7B—C7—H7C	109.5
O6—Sm—O3	80.72 (8)	C10—C9—H9A	117.9
O1—Sm—O3	136.93 (13)	C8—C9—H9A	117.9
O6—Sm—O2	116.96 (8)	C11—C12—H12A	109.5
O1—Sm—O2	71.06 (13)	C11—C12—H12B	109.5
O3—Sm—O2	151.40 (8)	H12A—C12—H12B	109.5
O6—Sm—O4	114.27 (8)	C11—C12—H12C	109.5
O1—Sm—O4	82.14 (10)	H12A—C12—H12C	109.5
O3—Sm—O4	72.26 (8)	H12B—C12—H12C	109.5
O2—Sm—O4	114.76 (8)	C11—C13—H13A	109.5
O6—Sm—O5	71.87 (7)	C11—C13—H13B	109.5
O1—Sm—O5	127.32 (9)	H13A—C13—H13B	109.5
O3—Sm—O5	80.31 (8)	C11—C13—H13C	109.5
O2—Sm—O5	84.24 (8)	H13A—C13—H13C	109.5
O4—Sm—O5	149.98 (8)	H13B—C13—H13C	109.5
O6—Sm—N1	153.57 (8)	C11—C14—H14A	109.5
O1—Sm—N1	126.90 (9)	C11—C14—H14B	109.5
O3—Sm—N1	81.42 (9)	H14A—C14—H14B	109.5
O2—Sm—N1	73.60 (8)	C11—C14—H14C	109.5
O4—Sm—N1	78.16 (8)	H14A—C14—H14C	109.5
O5—Sm—N1	86.04 (8)	H14B—C14—H14C	109.5
C1—N1—C5	115.2 (3)	C15—C16—H16A	109.5
C1—N1—Sm	123.4 (2)	C15—C16—H16B	109.5
C5—N1—Sm	121.4 (2)	H16A—C16—H16B	109.5
C3—N2—C7	121.5 (3)	C15—C16—H16C	109.5
C3—N2—C6	119.8 (3)	H16A—C16—H16C	109.5
C7—N2—C6	116.9 (3)	H16B—C16—H16C	109.5
C8—O1—Sm	138.0 (3)	C15—C17—H17A	109.5
C10—O2—Sm	138.8 (2)	C15—C17—H17B	109.5
C19—O3—Sm	138.2 (2)	H17A—C17—H17B	109.5
C21—O4—Sm	136.9 (2)	C15—C17—H17C	109.5
C30—O5—Sm	134.1 (2)	H17A—C17—H17C	109.5
C32—O6—Sm	134.7 (2)	H17B—C17—H17C	109.5
N1—C1—C2	124.1 (3)	C15—C18—H18A	109.5
C1—C2—C3	120.3 (3)	C15—C18—H18B	109.5
N2—C3—C4	122.5 (3)	H18A—C18—H18B	109.5
N2—C3—C2	122.4 (3)	C15—C18—H18C	109.5
C4—C3—C2	115.1 (3)	H18A—C18—H18C	109.5
C5—C4—C3	120.1 (3)	H18B—C18—H18C	109.5
N1—C5—C4	125.3 (3)	C21—C20—H20A	118.0
O1—C8—C9	124.0 (3)	C19—C20—H20A	118.0
O1—C8—C11	114.8 (3)	C22—C23—H23A	109.5
C9—C8—C11	121.1 (3)	C22—C23—H23B	109.5
C10—C9—C8	124.2 (3)	H23A—C23—H23B	109.5
O2—C10—C9	123.2 (3)	C22—C23—H23C	109.5
O2—C10—C15	115.2 (3)	H23A—C23—H23C	109.5
C9—C10—C15	121.6 (3)	H23B—C23—H23C	109.5
C14—C11—C12	109.3 (3)	C22—C24—H24A	109.5
C14—C11—C13	108.7 (3)	C22—C24—H24B	109.5
C12—C11—C13	109.6 (3)	H24A—C24—H24B	109.5
C14—C11—C8	108.7 (2)	C22—C24—H24C	109.5
C12—C11—C8	113.6 (3)	H24A—C24—H24C	109.5
C13—C11—C8	106.8 (3)	H24B—C24—H24C	109.5
C17—C15—C10	113.5 (3)	C22—C25—H25A	109.5
C17—C15—C18	108.8 (3)	C22—C25—H25B	109.5
C10—C15—C18	107.7 (3)	H25A—C25—H25B	109.5
C17—C15—C16	109.9 (3)	C22—C25—H25C	109.5
C10—C15—C16	107.2 (3)	H25A—C25—H25C	109.5
C18—C15—C16	109.7 (3)	H25B—C25—H25C	109.5
O3—C19—C20	124.0 (3)	C26—C27—H27A	109.5
O3—C19—C22	115.3 (3)	C26—C27—H27B	109.5
C20—C19—C22	120.7 (3)	H27A—C27—H27B	109.5
C21—C20—C19	124.0 (3)	C26—C27—H27C	109.5
O4—C21—C20	124.5 (3)	H27A—C27—H27C	109.5
O4—C21—C26	116.3 (3)	H27B—C27—H27C	109.5
C20—C21—C26	119.2 (3)	C26—C28—H28A	109.5
C25—C22—C23	109.7 (3)	C26—C28—H28B	109.5
C25—C22—C24	108.6 (4)	H28A—C28—H28B	109.5
C23—C22—C24	109.7 (4)	C26—C28—H28C	109.5
C25—C22—C19	107.6 (3)	H28A—C28—H28C	109.5
C23—C22—C19	106.4 (3)	H28B—C28—H28C	109.5
C24—C22—C19	114.8 (3)	C26—C29—H29A	109.5
C27—C26—C28	108.6 (3)	C26—C29—H29B	109.5
C27—C26—C29	109.4 (4)	H29A—C29—H29B	109.5
C28—C26—C29	109.2 (4)	C26—C29—H29C	109.5
C27—C26—C21	109.3 (3)	H29A—C29—H29C	109.5
C28—C26—C21	106.6 (3)	H29B—C29—H29C	109.5
C29—C26—C21	113.6 (3)	C32—C31—H31A	117.3
O5—C30—C31	123.5 (3)	C30—C31—H31A	117.3
O5—C30—C33	115.1 (3)	C33—C34—H34A	109.5
C31—C30—C33	121.4 (3)	C33—C34—H34B	109.5
C32—C31—C30	125.4 (3)	H34A—C34—H34B	109.5
O6—C32—C31	123.1 (3)	C33—C34—H34C	109.5
O6—C32—C37	115.4 (3)	H34A—C34—H34C	109.5
C31—C32—C37	121.4 (3)	H34B—C34—H34C	109.5
C35—C33—C36	110.3 (4)	C33—C35—H35A	109.5
C35—C33—C34	108.9 (3)	C33—C35—H35B	109.5
C36—C33—C34	108.3 (3)	H35A—C35—H35B	109.5
C35—C33—C30	109.6 (3)	C33—C35—H35C	109.5
C36—C33—C30	105.9 (3)	H35A—C35—H35C	109.5
C34—C33—C30	113.8 (3)	H35B—C35—H35C	109.5
C38—C37—C40	108.4 (4)	C33—C36—H36A	109.5
C38—C37—C39	110.7 (4)	C33—C36—H36B	109.5
C40—C37—C39	108.6 (3)	H36A—C36—H36B	109.5
C38—C37—C32	109.5 (3)	C33—C36—H36C	109.5
C40—C37—C32	113.7 (3)	H36A—C36—H36C	109.5
C39—C37—C32	106.0 (3)	H36B—C36—H36C	109.5
N1—C1—H1A	118.0	C37—C38—H38A	109.5
C2—C1—H1A	118.0	C37—C38—H38B	109.5
C1—C2—H2A	119.9	H38A—C38—H38B	109.5
C3—C2—H2A	119.9	C37—C38—H38C	109.5
C5—C4—H4A	120.0	H38A—C38—H38C	109.5
C3—C4—H4A	120.0	H38B—C38—H38C	109.5
N1—C5—H5A	117.3	C37—C39—H39A	109.5
C4—C5—H5A	117.3	C37—C39—H39B	109.5
N2—C6—H6A	109.5	H39A—C39—H39B	109.5
N2—C6—H6B	109.5	C37—C39—H39C	109.5
H6A—C6—H6B	109.5	H39A—C39—H39C	109.5
N2—C6—H6C	109.5	H39B—C39—H39C	109.5
H6A—C6—H6C	109.5	C37—C40—H40A	109.5
H6B—C6—H6C	109.5	C37—C40—H40B	109.5
N2—C7—H7A	109.5	H40A—C40—H40B	109.5
N2—C7—H7B	109.5	C37—C40—H40C	109.5
H7A—C7—H7B	109.5	H40A—C40—H40C	109.5
N2—C7—H7C	109.5	H40B—C40—H40C	109.5
H7A—C7—H7C	109.5