{μ-6,6'-Dimeth-oxy-2,2'-[propane-1,3-diyl-bis(nitrilo-methyl-idyne)]-diphenolato}-trinitratocopper(II)samarium(III) acetone solvate.

In the title complex, [CuSm(C(19)H(20)N(2)O(4))(NO(3))(3)]·CH(3)CO-CH(3), the Cu(II) atom is four-coordinated in a square-planar geometry by two O atoms and two N atoms of the deprotonated Schiff base. The Sm(III) atom is ten-coordinate, chelated by three nitrate groups and linked to the four O atoms of the deprotonated Schiff base.

Related literature

See Elmali & Elerman (2003 ▶, 2004 ▶) for similar copper–n class="Chemical">lanthanum complexes of the same Schiff base.

Experimental

Crystal data

[Cun class="Chemical">Sm(C19H20N2O4)(NO3)3]·C3H6O

M = 798.37

Triclinic,

a = 9.384 (5) Å

b = 12.111 (5) Å

c = 13.529 (6) Å

α = 73.071 (18)°

β = 86.984 (19)°

γ = 72.346 (18)°

V = 1400.5 (11) Å3

Z = 2

Mo Kα radiation

μ = 2.91 mm−1

T = 295 (2) K

0.33 × 0.30 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.446, T max = 0.610 (expected range = 0.420–0.575)

13938 measured reflections

6381 independent reflections

5692 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.062

S = 1.09

6381 reflections

392 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.41 e Å−3

Data collection: RAPID-AUTO (Rigaku Corporation, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807061454/ng2393sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061454/ng2393Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[CuSm(C19H20N2O4)(NO3)3]·C3H6O	Z = 2
Mr = 798.37	F000 = 792
Triclinic, P1	Dx = 1.893 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.384 (5) Å	Cell parameters from 12555 reflections
b = 12.111 (5) Å	θ = 6.3–55.0º
c = 13.529 (6) Å	µ = 2.91 mm−1
α = 73.071 (18)º	T = 295 (2) K
β = 86.984 (19)º	Block, green
γ = 72.346 (18)º	0.33 × 0.30 × 0.19 mm
V = 1400.5 (11) Å3

Rigaku R-AXIS RAPID diffractometer	6381 independent reflections
Radiation source: fine-focus sealed tube	5692 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
T = 295(2) K	θmax = 27.7º
ω scan	θmin = 3.2º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	h = −12→12
Tmin = 0.446, Tmax = 0.610	k = −15→15
13938 measured reflections	l = −17→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026	H-atom parameters constrained
wR(F2) = 0.062	w = 1/[σ2(Fo2) + (0.0234P)2 + 0.9589P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
6381 reflections	Δρmax = 0.57 e Å−3
392 parameters	Δρmin = −0.41 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
C1	0.5501 (3)	0.7332 (2)	0.4170 (2)	0.0360 (6)
C2	0.6420 (3)	0.7711 (2)	0.3375 (2)	0.0380 (6)
C3	0.7936 (3)	0.7349 (3)	0.3504 (3)	0.0465 (7)
H1	0.8522	0.7622	0.2969	0.056*
C4	0.8598 (4)	0.6566 (3)	0.4449 (3)	0.0537 (9)
H2	0.9634	0.6310	0.4546	0.064*
C5	0.7740 (4)	0.6175 (3)	0.5226 (3)	0.0527 (8)
H3	0.8195	0.5648	0.5852	0.063*
C6	0.6162 (3)	0.6554 (3)	0.5105 (2)	0.0422 (7)
C7	0.5318 (4)	0.6060 (3)	0.5936 (2)	0.0490 (8)
H4	0.5879	0.5478	0.6504	0.059*
C8	0.3395 (5)	0.5602 (4)	0.6970 (3)	0.0819 (14)
H5	0.3455	0.5953	0.7520	0.098*
H6	0.4067	0.4780	0.7162	0.098*
C9	0.1820 (5)	0.5565 (3)	0.6872 (3)	0.0663 (11)
H7	0.1718	0.5328	0.6260	0.080*
H8	0.1627	0.4960	0.7468	0.080*
C10	0.0698 (4)	0.6750 (3)	0.6799 (2)	0.0538 (8)
H9	−0.0281	0.6636	0.6933	0.065*
H10	0.0937	0.7071	0.7326	0.065*
C11	−0.0655 (3)	0.8406 (3)	0.5481 (2)	0.0424 (7)
H11	−0.1403	0.8359	0.5956	0.051*
C12	−0.1089 (3)	0.9324 (3)	0.4522 (2)	0.0384 (6)
C13	−0.2583 (4)	1.0074 (3)	0.4383 (3)	0.0497 (8)
H12	−0.3221	0.9999	0.4932	0.060*
C14	−0.3108 (4)	1.0906 (3)	0.3460 (3)	0.0533 (8)
H13	−0.4098	1.1394	0.3381	0.064*
C15	−0.2161 (3)	1.1026 (3)	0.2633 (3)	0.0470 (7)
H14	−0.2519	1.1588	0.1998	0.056*
C16	−0.0682 (3)	1.0303 (2)	0.2762 (2)	0.0376 (6)
C17	−0.0128 (3)	0.9440 (2)	0.3701 (2)	0.0340 (6)
C18	−0.0188 (4)	1.1099 (3)	0.0970 (3)	0.0576 (9)
H15	−0.0858	1.0772	0.0718	0.086*
H16	0.0640	1.1107	0.0523	0.086*
H17	−0.0709	1.1909	0.0983	0.086*
C19	0.6504 (4)	0.8849 (4)	0.1599 (3)	0.0568 (9)
H18	0.7168	0.9218	0.1802	0.085*
H19	0.5843	0.9427	0.1042	0.085*
H20	0.7078	0.8167	0.1376	0.085*
C20	0.1935 (7)	0.3884 (5)	−0.0090 (5)	0.1100 (19)
H21	0.1201	0.4099	−0.0636	0.165*
H22	0.1525	0.3581	0.0562	0.165*
H23	0.2805	0.3270	−0.0197	0.165*
C21	0.2360 (6)	0.4971 (4)	−0.0088 (4)	0.0800 (13)
C22	0.3365 (7)	0.4818 (5)	0.0816 (4)	0.1022 (18)
H24	0.3632	0.5547	0.0722	0.153*
H25	0.4256	0.4154	0.0852	0.153*
H26	0.2844	0.4658	0.1447	0.153*
Cu2	0.24465 (4)	0.75758 (3)	0.49629 (3)	0.03670 (8)
N1	0.3895 (3)	0.6310 (2)	0.60036 (19)	0.0498 (7)
N2	0.0646 (3)	0.7631 (2)	0.57760 (18)	0.0402 (5)
N3	0.3263 (3)	1.1105 (2)	0.2284 (2)	0.0510 (7)
N4	0.3808 (3)	0.8126 (3)	0.0426 (2)	0.0478 (6)
N5	0.1427 (3)	0.6889 (3)	0.2369 (2)	0.0528 (7)
O1	0.4021 (2)	0.77107 (19)	0.39863 (15)	0.0439 (5)
O2	0.5643 (2)	0.84507 (19)	0.24634 (16)	0.0447 (5)
O3	0.1281 (2)	0.87450 (18)	0.37652 (15)	0.0411 (5)
O4	0.0358 (2)	1.03583 (18)	0.20020 (16)	0.0436 (5)
O5	0.3167 (3)	1.0333 (2)	0.31093 (18)	0.0543 (6)
O6	0.3339 (4)	1.2091 (2)	0.2275 (2)	0.0787 (9)
O7	0.3255 (3)	1.0798 (2)	0.14667 (18)	0.0535 (6)
O8	0.3018 (3)	0.9182 (2)	0.04383 (17)	0.0524 (5)
O9	0.4101 (3)	0.7863 (3)	−0.0366 (2)	0.0736 (8)
O10	0.4267 (3)	0.7385 (2)	0.12933 (19)	0.0545 (6)
O11	0.0985 (3)	0.7954 (2)	0.1774 (2)	0.0568 (6)
O12	0.0852 (4)	0.6118 (3)	0.2345 (3)	0.0822 (9)
O13	0.2480 (3)	0.6667 (2)	0.2982 (2)	0.0590 (6)
O14	0.2011 (5)	0.5883 (3)	−0.0775 (3)	0.1208 (15)
Sm1	0.286846 (16)	0.877380 (13)	0.233252 (11)	0.03533 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0338 (14)	0.0327 (13)	0.0389 (14)	−0.0044 (11)	−0.0040 (11)	−0.0115 (12)
C2	0.0372 (15)	0.0340 (13)	0.0426 (15)	−0.0094 (11)	−0.0013 (12)	−0.0117 (12)
C3	0.0372 (16)	0.0438 (16)	0.063 (2)	−0.0129 (13)	0.0002 (14)	−0.0205 (16)
C4	0.0359 (16)	0.0490 (18)	0.075 (2)	−0.0042 (14)	−0.0133 (16)	−0.0223 (18)
C5	0.0488 (19)	0.0469 (17)	0.055 (2)	0.0011 (14)	−0.0207 (16)	−0.0163 (16)
C6	0.0437 (16)	0.0355 (14)	0.0418 (16)	−0.0010 (12)	−0.0114 (13)	−0.0120 (13)
C7	0.054 (2)	0.0409 (15)	0.0349 (15)	0.0064 (14)	−0.0118 (14)	−0.0049 (13)
C8	0.084 (3)	0.067 (2)	0.045 (2)	0.009 (2)	0.012 (2)	0.0240 (18)
C9	0.112 (4)	0.0417 (17)	0.0437 (19)	−0.033 (2)	0.014 (2)	−0.0017 (15)
C10	0.060 (2)	0.065 (2)	0.0346 (16)	−0.0272 (17)	0.0042 (14)	−0.0029 (15)
C11	0.0416 (16)	0.0494 (16)	0.0441 (16)	−0.0206 (13)	0.0115 (13)	−0.0198 (14)
C12	0.0362 (15)	0.0393 (14)	0.0442 (16)	−0.0129 (12)	0.0015 (12)	−0.0174 (13)
C13	0.0403 (17)	0.0566 (19)	0.059 (2)	−0.0135 (14)	0.0077 (15)	−0.0286 (17)
C14	0.0332 (16)	0.0585 (19)	0.067 (2)	−0.0022 (14)	−0.0076 (15)	−0.0275 (18)
C15	0.0414 (17)	0.0416 (15)	0.0527 (18)	0.0004 (13)	−0.0143 (14)	−0.0164 (14)
C16	0.0365 (15)	0.0346 (13)	0.0420 (15)	−0.0074 (11)	−0.0021 (12)	−0.0144 (12)
C17	0.0315 (13)	0.0328 (13)	0.0378 (14)	−0.0079 (10)	−0.0037 (11)	−0.0115 (11)
C18	0.061 (2)	0.0499 (18)	0.0401 (17)	0.0023 (16)	−0.0113 (15)	0.0023 (15)
C19	0.051 (2)	0.070 (2)	0.052 (2)	−0.0303 (17)	0.0147 (16)	−0.0114 (18)
C20	0.117 (5)	0.084 (3)	0.109 (4)	−0.019 (3)	−0.038 (4)	−0.003 (3)
C21	0.099 (4)	0.056 (2)	0.063 (3)	−0.003 (2)	0.019 (2)	−0.010 (2)
C22	0.153 (6)	0.071 (3)	0.081 (3)	−0.034 (3)	0.015 (3)	−0.022 (3)
Cu2	0.03880 (19)	0.03451 (16)	0.02912 (16)	−0.00780 (14)	−0.00024 (14)	−0.00084 (14)
N1	0.0625 (18)	0.0373 (13)	0.0317 (13)	−0.0001 (12)	0.0018 (12)	0.0014 (11)
N2	0.0490 (15)	0.0431 (13)	0.0323 (12)	−0.0213 (11)	0.0042 (11)	−0.0092 (11)
N3	0.0517 (16)	0.0426 (14)	0.0546 (17)	−0.0123 (12)	−0.0041 (13)	−0.0090 (13)
N4	0.0424 (15)	0.0607 (17)	0.0417 (15)	−0.0184 (13)	0.0044 (12)	−0.0147 (13)
N5	0.0500 (17)	0.0454 (15)	0.0623 (18)	−0.0177 (13)	0.0185 (14)	−0.0138 (14)
O1	0.0326 (10)	0.0514 (12)	0.0324 (10)	−0.0059 (9)	−0.0036 (8)	0.0044 (9)
O2	0.0373 (11)	0.0522 (12)	0.0375 (11)	−0.0141 (9)	0.0013 (9)	−0.0015 (9)
O3	0.0360 (11)	0.0396 (10)	0.0342 (10)	−0.0018 (8)	0.0006 (8)	−0.0005 (9)
O4	0.0397 (11)	0.0387 (10)	0.0376 (11)	−0.0001 (8)	−0.0067 (9)	0.0004 (9)
O5	0.0666 (16)	0.0520 (13)	0.0429 (12)	−0.0183 (11)	0.0025 (11)	−0.0113 (11)
O6	0.105 (2)	0.0482 (14)	0.085 (2)	−0.0268 (15)	−0.0138 (18)	−0.0155 (14)
O7	0.0694 (16)	0.0457 (12)	0.0414 (12)	−0.0210 (11)	0.0005 (11)	−0.0025 (10)
O8	0.0641 (15)	0.0494 (12)	0.0365 (11)	−0.0139 (11)	0.0023 (10)	−0.0052 (10)
O9	0.0754 (19)	0.098 (2)	0.0495 (15)	−0.0150 (16)	0.0049 (13)	−0.0367 (16)
O10	0.0538 (14)	0.0500 (13)	0.0507 (14)	−0.0041 (10)	−0.0009 (11)	−0.0126 (11)
O11	0.0489 (14)	0.0500 (13)	0.0649 (16)	−0.0132 (10)	−0.0024 (11)	−0.0077 (12)
O12	0.085 (2)	0.0648 (17)	0.115 (3)	−0.0453 (16)	0.0311 (19)	−0.0355 (18)
O13	0.0676 (17)	0.0407 (12)	0.0568 (15)	−0.0125 (11)	0.0042 (13)	−0.0008 (11)
O14	0.180 (4)	0.069 (2)	0.076 (2)	−0.009 (2)	−0.003 (2)	0.0073 (18)
Sm1	0.03475 (8)	0.03416 (8)	0.02833 (8)	−0.00614 (5)	−0.00093 (5)	0.00000 (5)

C1—O1	1.335 (3)	C18—H15	0.9600
C1—C6	1.381 (4)	C18—H16	0.9600
C1—C2	1.402 (4)	C18—H17	0.9600
C2—C3	1.360 (4)	C19—O2	1.436 (4)
C2—O2	1.382 (4)	C19—H18	0.9600
C3—C4	1.393 (5)	C19—H19	0.9600
C3—H1	0.9300	C19—H20	0.9600
C4—C5	1.353 (5)	C20—C21	1.488 (7)
C4—H2	0.9300	C20—H21	0.9600
C5—C6	1.414 (4)	C20—H22	0.9600
C5—H3	0.9300	C20—H23	0.9600
C6—C7	1.433 (5)	C21—O14	1.186 (5)
C7—N1	1.281 (4)	C21—C22	1.518 (7)
C7—H4	0.9300	C22—H24	0.9600
C8—N1	1.481 (4)	C22—H25	0.9600
C8—C9	1.506 (6)	C22—H26	0.9600
C8—H5	0.9700	Cu2—O3	1.933 (2)
C8—H6	0.9700	Cu2—O1	1.942 (2)
C9—C10	1.479 (5)	Cu2—N2	1.962 (3)
C9—H7	0.9700	Cu2—N1	1.965 (3)
C9—H8	0.9700	N3—O6	1.215 (4)
C10—N2	1.474 (4)	N3—O5	1.249 (4)
C10—H9	0.9700	N3—O7	1.265 (4)
C10—H10	0.9700	N4—O9	1.201 (3)
C11—N2	1.291 (4)	N4—O10	1.254 (3)
C11—C12	1.424 (4)	N4—O8	1.274 (3)
C11—H11	0.9300	N5—O12	1.221 (4)
C12—C17	1.395 (4)	N5—O13	1.238 (4)
C12—C13	1.407 (4)	N5—O11	1.261 (4)
C13—C14	1.359 (5)	O1—Sm1	2.359 (2)
C13—H12	0.9300	O2—Sm1	2.520 (2)
C14—C15	1.393 (5)	O3—Sm1	2.380 (2)
C14—H13	0.9300	O4—Sm1	2.510 (2)
C15—C16	1.386 (4)	O5—Sm1	2.501 (2)
C15—H14	0.9300	O7—Sm1	2.517 (2)
C16—O4	1.381 (4)	O8—Sm1	2.469 (2)
C16—C17	1.394 (4)	O10—Sm1	2.525 (2)
C17—O3	1.326 (3)	O11—Sm1	2.515 (3)
C18—O4	1.443 (4)	O13—Sm1	2.577 (3)
O1—C1—C6	122.4 (3)	H25—C22—H26	109.5
O1—C1—C2	118.8 (3)	O3—Cu2—O1	79.81 (9)
C6—C1—C2	118.7 (3)	O3—Cu2—N2	91.27 (10)
C3—C2—O2	124.3 (3)	O1—Cu2—N2	171.07 (9)
C3—C2—C1	121.9 (3)	O3—Cu2—N1	169.89 (10)
O2—C2—C1	113.8 (2)	O1—Cu2—N1	90.75 (11)
C2—C3—C4	119.1 (3)	N2—Cu2—N1	98.18 (12)
C2—C3—H1	120.4	C7—N1—C8	114.6 (3)
C4—C3—H1	120.4	C7—N1—Cu2	124.2 (2)
C5—C4—C3	120.2 (3)	C8—N1—Cu2	121.2 (2)
C5—C4—H2	119.9	C11—N2—C10	114.6 (3)
C3—C4—H2	119.9	C11—N2—Cu2	124.6 (2)
C4—C5—C6	121.2 (3)	C10—N2—Cu2	120.8 (2)
C4—C5—H3	119.4	O6—N3—O5	121.5 (3)
C6—C5—H3	119.4	O6—N3—O7	122.7 (3)
C1—C6—C5	118.8 (3)	O5—N3—O7	115.9 (3)
C1—C6—C7	122.5 (3)	O9—N4—O10	122.3 (3)
C5—C6—C7	118.6 (3)	O9—N4—O8	122.0 (3)
N1—C7—C6	128.8 (3)	O10—N4—O8	115.7 (2)
N1—C7—H4	115.6	O12—N5—O13	121.7 (3)
C6—C7—H4	115.6	O12—N5—O11	122.0 (3)
N1—C8—C9	112.9 (3)	O13—N5—O11	116.3 (3)
N1—C8—H5	109.0	C1—O1—Cu2	128.75 (18)
C9—C8—H5	109.0	C1—O1—Sm1	123.53 (18)
N1—C8—H6	109.0	Cu2—O1—Sm1	107.68 (9)
C9—C8—H6	109.0	C2—O2—C19	117.3 (2)
H5—C8—H6	107.8	C2—O2—Sm1	118.50 (17)
C10—C9—C8	112.1 (3)	C19—O2—Sm1	123.5 (2)
C10—C9—H7	109.2	C17—O3—Cu2	129.08 (18)
C8—C9—H7	109.2	C17—O3—Sm1	123.76 (17)
C10—C9—H8	109.2	Cu2—O3—Sm1	107.15 (9)
C8—C9—H8	109.2	C16—O4—C18	117.2 (2)
H7—C9—H8	107.9	C16—O4—Sm1	118.80 (16)
N2—C10—C9	112.3 (3)	C18—O4—Sm1	121.66 (19)
N2—C10—H9	109.2	N3—O5—Sm1	97.49 (18)
C9—C10—H9	109.2	N3—O7—Sm1	96.27 (18)
N2—C10—H10	109.2	N4—O8—Sm1	97.71 (17)
C9—C10—H10	109.2	N4—O10—Sm1	95.60 (17)
H9—C10—H10	107.9	N5—O11—Sm1	98.4 (2)
N2—C11—C12	128.3 (3)	N5—O13—Sm1	96.02 (18)
N2—C11—H11	115.9	O1—Sm1—O3	63.27 (8)
C12—C11—H11	115.9	O1—Sm1—O8	148.32 (8)
C17—C12—C13	119.5 (3)	O3—Sm1—O8	146.44 (8)
C17—C12—C11	122.5 (3)	O1—Sm1—O5	73.64 (8)
C13—C12—C11	117.8 (3)	O3—Sm1—O5	73.43 (8)
C14—C13—C12	121.1 (3)	O8—Sm1—O5	117.84 (8)
C14—C13—H12	119.5	O1—Sm1—O4	124.51 (7)
C12—C13—H12	119.5	O3—Sm1—O4	64.03 (7)
C13—C14—C15	119.9 (3)	O8—Sm1—O4	87.13 (8)
C13—C14—H13	120.0	O5—Sm1—O4	76.07 (8)
C15—C14—H13	120.0	O1—Sm1—O11	115.72 (8)
C16—C15—C14	119.6 (3)	O3—Sm1—O11	80.42 (8)
C16—C15—H14	120.2	O8—Sm1—O11	73.58 (9)
C14—C15—H14	120.2	O5—Sm1—O11	144.02 (8)
O4—C16—C15	124.5 (3)	O4—Sm1—O11	70.38 (8)
O4—C16—C17	114.3 (2)	O1—Sm1—O7	117.15 (8)
C15—C16—C17	121.2 (3)	O3—Sm1—O7	114.49 (8)
O3—C17—C16	118.4 (3)	O8—Sm1—O7	67.60 (8)
O3—C17—C12	123.0 (3)	O5—Sm1—O7	50.26 (8)
C16—C17—C12	118.6 (3)	O4—Sm1—O7	71.58 (8)
O4—C18—H15	109.5	O11—Sm1—O7	125.99 (8)
O4—C18—H16	109.5	O1—Sm1—O2	64.43 (7)
H15—C18—H16	109.5	O3—Sm1—O2	123.87 (7)
O4—C18—H17	109.5	O8—Sm1—O2	89.45 (8)
H15—C18—H17	109.5	O5—Sm1—O2	73.80 (8)
H16—C18—H17	109.5	O4—Sm1—O2	143.74 (7)
O2—C19—H18	109.5	O11—Sm1—O2	142.17 (8)
O2—C19—H19	109.5	O7—Sm1—O2	73.77 (8)
H18—C19—H19	109.5	O1—Sm1—O10	100.83 (8)
O2—C19—H20	109.5	O3—Sm1—O10	139.45 (8)
H18—C19—H20	109.5	O8—Sm1—O10	50.74 (8)
H19—C19—H20	109.5	O5—Sm1—O10	141.10 (8)
C21—C20—H21	109.5	O4—Sm1—O10	130.89 (7)
C21—C20—H22	109.5	O11—Sm1—O10	73.75 (9)
H21—C20—H22	109.5	O7—Sm1—O10	105.97 (8)
C21—C20—H23	109.5	O2—Sm1—O10	69.44 (8)
H21—C20—H23	109.5	O1—Sm1—O13	69.00 (8)
H22—C20—H23	109.5	O3—Sm1—O13	71.58 (8)
O14—C21—C20	122.5 (5)	O8—Sm1—O13	104.97 (8)
O14—C21—C22	121.5 (5)	O5—Sm1—O13	137.17 (8)
C20—C21—C22	115.9 (4)	O4—Sm1—O13	108.91 (9)
C21—C22—H24	109.5	O11—Sm1—O13	49.23 (8)
C21—C22—H25	109.5	O7—Sm1—O13	172.57 (8)
H24—C22—H25	109.5	O2—Sm1—O13	106.84 (8)
C21—C22—H26	109.5	O10—Sm1—O13	67.87 (9)
H24—C22—H26	109.5