(Acetone-2κO){μ-6,6'-dimeth-oxy-2,2'-[propane-1,2-diylbis(nitrilo-methyl-idyne)]diphenolato-κ1:2O,O,O,O:O,N,N',O}tris-(nitrato-1κO,O')copper(II)samarium(III).

In the title heteronuclear complex, [CuSm(C(19)H(20)N(2)O(4))(NO(3))(3)(CH(3)COCH(3))], the Cu(II) ion is five-coordinated by two O and two N atoms from the 6,6'-dimeth-oxy-2,2'-[propane-1,2-diylbis(nitrilo-methyl-idyne)]diphenolate ligand (L) and by an O atom from the acetone mol-ecule in a square-pyramidal geometry. The Sm(III) ion is ten-coordinated by six O atoms from the three nitrate ligands and four O atoms from the L ligand. In L, the C atoms of the diamino-propane fragment are disordered over two positions in a 0.674 (10):0.326 (10) ratio.

Related literature

For similar Cu–Ln (Ln = Gd, Pr and Tb) dinuclear complexes of the N,N′-bis­(3-methoxy­salicyl­idene)propane-1,2-diamine ligand, see: Kara et al. (2000 ▶); Sun et al. (2007 ▶, 2009 ▶).

Experimental

Crystal data

[CuSm(C19H20N2O4)(NO3)3(C3H6O)]

M = 797.38

Monoclinic,

a = 9.882 (4) Å

b = 18.868 (5) Å

c = 15.631 (5) Å

β = 95.320 (16)°

V = 2901.9 (16) Å3

Z = 4

Mo Kα radiation

μ = 2.81 mm−1

T = 291 K

0.39 × 0.33 × 0.29 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.404, T max = 0.500 (expected range = 0.357–0.442)

28125 measured reflections

6634 independent reflections

5584 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.088

S = 1.07

6634 reflections

421 parameters

36 restraints

H-atom parameters constrained

Δρmax = 1.03 e Å−3

Δρmin = −0.74 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902399X/cv2575sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902399X/cv2575Isup2.hkl

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

[CuSm(C19H20N2O4)(NO3)3(C3H6O)]	F(000) = 1580
Mr = 797.38	Dx = 1.825 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 23031 reflections
a = 9.882 (4) Å	θ = 3.0–27.5°
b = 18.868 (5) Å	µ = 2.81 mm−1
c = 15.631 (5) Å	T = 291 K
β = 95.320 (16)°	Block, brown
V = 2901.9 (16) Å3	0.39 × 0.33 × 0.29 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	6634 independent reflections
Radiation source: fine-focus sealed tube	5584 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
Tmin = 0.404, Tmax = 0.500	k = −24→24
28125 measured reflections	l = −19→20

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0469P)2 + 1.8845P] where P = (Fo2 + 2Fc2)/3
6634 reflections	(Δ/σ)max = 0.006
421 parameters	Δρmax = 1.02 e Å−3
36 restraints	Δρmin = −0.74 e Å−3

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	Occ. (<1)
C8'	0.1263 (19)	0.1131 (8)	0.6707 (10)	0.071 (4)	0.326 (10)
H4'	0.0359	0.1213	0.6897	0.086*	0.326 (10)
C9'	0.145 (3)	0.0470 (10)	0.6393 (18)	0.150 (11)	0.326 (10)
H5A	0.1310	0.0479	0.5778	0.225*	0.326 (10)
H6A	0.0817	0.0149	0.6615	0.225*	0.326 (10)
H7A	0.2362	0.0315	0.6566	0.225*	0.326 (10)
C10'	0.1389 (17)	0.1317 (7)	0.5793 (11)	0.051 (4)	0.326 (10)
H8A	0.0701	0.1072	0.5421	0.061*	0.326 (10)
H9A	0.2277	0.1182	0.5631	0.061*	0.326 (10)
C8	0.1982 (10)	0.1147 (4)	0.6338 (6)	0.075 (2)	0.674 (10)
H4	0.1715	0.0691	0.6569	0.091*	0.674 (10)
C9	0.2955 (13)	0.1009 (7)	0.5751 (7)	0.129 (4)	0.674 (10)
H5	0.3049	0.1418	0.5397	0.193*	0.674 (10)
H6	0.2663	0.0612	0.5396	0.193*	0.674 (10)
H7	0.3815	0.0902	0.6062	0.193*	0.674 (10)
C10	0.0731 (13)	0.1457 (5)	0.5815 (8)	0.096 (4)	0.674 (10)
H8	0.0545	0.1216	0.5268	0.115*	0.674 (10)
H9	−0.0069	0.1437	0.6130	0.115*	0.674 (10)
Sm1	0.28473 (2)	0.426361 (8)	0.751802 (10)	0.03909 (7)
Cu	0.20496 (6)	0.25917 (2)	0.67412 (3)	0.05590 (14)
O1	0.3107 (3)	0.30109 (12)	0.76905 (17)	0.0528 (7)
O2	0.4514 (3)	0.37744 (13)	0.87833 (16)	0.0527 (7)
O3	0.1956 (3)	0.35392 (13)	0.63401 (16)	0.0525 (7)
O4	0.2338 (3)	0.48443 (14)	0.59859 (16)	0.0512 (6)
O5	0.4888 (3)	0.39591 (16)	0.6739 (2)	0.0659 (8)
O6	0.6496 (5)	0.4695 (2)	0.6546 (3)	0.1085 (16)
O7	0.4919 (3)	0.49733 (14)	0.7349 (2)	0.0609 (7)
O8	0.2232 (4)	0.55708 (17)	0.7635 (2)	0.0720 (10)
O9	0.2694 (5)	0.62299 (18)	0.8738 (3)	0.1104 (17)
O10	0.3179 (5)	0.51210 (16)	0.87669 (19)	0.0808 (11)
O11	0.1305 (5)	0.3903 (3)	0.8594 (3)	0.0988 (13)
O12	−0.0836 (5)	0.4062 (3)	0.8508 (4)	0.132 (2)
O13	0.0338 (4)	0.4383 (2)	0.7491 (3)	0.0904 (12)
O14	−0.0249 (4)	0.25774 (19)	0.7448 (2)	0.0749 (9)
N1	0.2387 (5)	0.16408 (19)	0.7111 (3)	0.0851 (14)
N2	0.1181 (5)	0.2182 (2)	0.5703 (3)	0.0780 (13)
N3	0.5473 (4)	0.45422 (18)	0.6863 (2)	0.0566 (8)
N4	0.2711 (4)	0.56584 (17)	0.8385 (2)	0.0606 (10)
N5	0.0199 (5)	0.4123 (2)	0.8212 (3)	0.0754 (12)
C1	0.3693 (4)	0.26602 (18)	0.8360 (3)	0.0465 (8)
C2	0.4440 (4)	0.30587 (19)	0.8984 (2)	0.0494 (9)
C3	0.5035 (5)	0.2754 (3)	0.9723 (3)	0.0700 (13)
H1	0.5525	0.3028	1.0138	0.084*
C4	0.4889 (6)	0.2021 (3)	0.9838 (4)	0.0815 (16)
H2	0.5252	0.1809	1.0346	0.098*
C5	0.4224 (5)	0.1622 (2)	0.9217 (4)	0.0770 (15)
H3	0.4164	0.1135	0.9298	0.092*
C6	0.3628 (4)	0.1918 (2)	0.8460 (3)	0.0559 (10)
C7	0.3007 (5)	0.1443 (2)	0.7817 (4)	0.0759 (15)
C11	0.0826 (6)	0.2515 (3)	0.5020 (3)	0.0829 (16)
H10	0.0442	0.2253	0.4555	0.099*
C12	0.0966 (5)	0.3270 (3)	0.4898 (3)	0.0638 (12)
C13	0.0536 (5)	0.3555 (4)	0.4084 (3)	0.0800 (16)
H11	0.0141	0.3258	0.3656	0.096*
C14	0.0686 (6)	0.4248 (3)	0.3915 (3)	0.0792 (16)
H12	0.0377	0.4423	0.3375	0.095*
C15	0.1281 (5)	0.4698 (3)	0.4517 (2)	0.0652 (12)
H13	0.1398	0.5174	0.4387	0.078*
C16	0.1710 (4)	0.4441 (2)	0.5324 (2)	0.0508 (9)
C17	0.1542 (4)	0.3732 (2)	0.5535 (2)	0.0511 (9)
C18	0.2810 (6)	0.5531 (2)	0.5755 (3)	0.0662 (12)
H14	0.2046	0.5825	0.5569	0.099*
H15	0.3388	0.5484	0.5298	0.099*
H16	0.3311	0.5744	0.6245	0.099*
C19	0.5576 (6)	0.4172 (2)	0.9257 (3)	0.0725 (14)
H17	0.5695	0.4616	0.8975	0.109*
H18	0.6409	0.3907	0.9283	0.109*
H19	0.5335	0.4257	0.9829	0.109*
C20	−0.2540 (7)	0.2557 (4)	0.7781 (5)	0.108 (2)
H20	−0.3030	0.2983	0.7886	0.162*
H21	−0.2161	0.2362	0.8319	0.162*
H22	−0.3149	0.2218	0.7493	0.162*
C21	−0.1422 (5)	0.2722 (2)	0.7232 (3)	0.0635 (11)
C22	−0.1820 (6)	0.3064 (3)	0.6394 (4)	0.0856 (16)
H23	−0.2482	0.3426	0.6467	0.128*
H24	−0.2203	0.2715	0.5995	0.128*
H25	−0.1035	0.3272	0.6177	0.128*

	U11	U22	U33	U12	U13	U23
C8'	0.072 (5)	0.071 (5)	0.072 (5)	−0.0003 (10)	0.0066 (11)	−0.0003 (10)
C9'	0.158 (14)	0.134 (13)	0.159 (14)	−0.015 (9)	0.018 (9)	0.004 (9)
C10'	0.056 (7)	0.029 (5)	0.069 (7)	−0.006 (5)	0.015 (6)	−0.023 (5)
C8	0.077 (2)	0.073 (2)	0.076 (2)	−0.0005 (10)	0.0069 (10)	−0.0024 (10)
C9	0.129 (5)	0.128 (4)	0.129 (4)	0.0003 (10)	0.0126 (11)	−0.0001 (10)
C10	0.101 (9)	0.075 (6)	0.107 (7)	0.005 (6)	−0.011 (7)	−0.049 (5)
Sm1	0.04727 (12)	0.03289 (10)	0.03616 (10)	−0.00080 (7)	−0.00128 (7)	−0.00168 (6)
Cu	0.0668 (3)	0.0395 (2)	0.0598 (3)	−0.0081 (2)	−0.0022 (2)	−0.0138 (2)
O1	0.0649 (19)	0.0321 (11)	0.0580 (15)	−0.0026 (11)	−0.0123 (13)	0.0002 (10)
O2	0.0618 (18)	0.0416 (12)	0.0507 (14)	−0.0020 (12)	−0.0166 (13)	0.0029 (11)
O3	0.0677 (19)	0.0485 (14)	0.0396 (13)	−0.0129 (13)	−0.0046 (12)	−0.0065 (10)
O4	0.0583 (17)	0.0523 (14)	0.0421 (13)	−0.0003 (12)	−0.0003 (12)	0.0079 (11)
O5	0.065 (2)	0.0495 (15)	0.085 (2)	−0.0083 (14)	0.0213 (17)	−0.0209 (15)
O6	0.092 (3)	0.073 (2)	0.172 (4)	−0.019 (2)	0.074 (3)	−0.014 (3)
O7	0.0613 (19)	0.0437 (14)	0.0786 (19)	−0.0055 (13)	0.0112 (15)	−0.0144 (13)
O8	0.099 (3)	0.0538 (16)	0.0581 (17)	0.0220 (17)	−0.0187 (17)	−0.0100 (13)
O9	0.175 (5)	0.0548 (19)	0.092 (3)	0.032 (2)	−0.038 (3)	−0.0323 (18)
O10	0.134 (3)	0.0544 (17)	0.0495 (16)	0.0307 (19)	−0.0160 (18)	−0.0106 (13)
O11	0.080 (3)	0.139 (4)	0.081 (3)	0.004 (3)	0.028 (2)	0.038 (3)
O12	0.087 (3)	0.167 (5)	0.151 (5)	0.000 (3)	0.069 (4)	−0.007 (4)
O13	0.061 (2)	0.117 (3)	0.093 (3)	0.005 (2)	0.008 (2)	0.022 (2)
O14	0.060 (2)	0.082 (2)	0.082 (2)	0.0122 (17)	0.0029 (18)	0.0157 (17)
N1	0.091 (3)	0.0357 (18)	0.124 (4)	−0.0006 (19)	−0.016 (3)	−0.015 (2)
N2	0.093 (3)	0.071 (2)	0.070 (3)	−0.030 (2)	0.010 (2)	−0.036 (2)
N3	0.056 (2)	0.0450 (17)	0.070 (2)	−0.0027 (16)	0.0151 (18)	0.0000 (16)
N4	0.078 (3)	0.0443 (17)	0.057 (2)	0.0107 (16)	−0.0078 (19)	−0.0121 (14)
N5	0.070 (3)	0.074 (3)	0.087 (3)	−0.008 (2)	0.032 (3)	−0.007 (2)
C1	0.043 (2)	0.0379 (17)	0.059 (2)	0.0019 (14)	0.0029 (17)	0.0066 (15)
C2	0.044 (2)	0.0475 (19)	0.055 (2)	0.0063 (16)	−0.0028 (17)	0.0117 (16)
C3	0.067 (3)	0.068 (3)	0.071 (3)	0.003 (2)	−0.016 (2)	0.015 (2)
C4	0.072 (3)	0.074 (3)	0.095 (4)	0.007 (3)	−0.011 (3)	0.044 (3)
C5	0.054 (3)	0.050 (2)	0.126 (5)	0.004 (2)	0.001 (3)	0.033 (3)
C6	0.041 (2)	0.0401 (18)	0.086 (3)	0.0040 (16)	0.004 (2)	0.0095 (18)
C7	0.062 (3)	0.0345 (19)	0.129 (5)	0.0030 (19)	−0.003 (3)	0.000 (2)
C11	0.087 (4)	0.105 (4)	0.056 (3)	−0.030 (3)	0.004 (3)	−0.038 (3)
C12	0.054 (3)	0.092 (3)	0.045 (2)	−0.011 (2)	0.0046 (18)	−0.021 (2)
C13	0.062 (3)	0.133 (5)	0.042 (2)	−0.006 (3)	−0.007 (2)	−0.023 (3)
C14	0.060 (3)	0.135 (5)	0.041 (2)	0.010 (3)	−0.005 (2)	0.000 (3)
C15	0.054 (3)	0.100 (3)	0.042 (2)	0.015 (2)	0.0065 (19)	0.009 (2)
C16	0.045 (2)	0.072 (2)	0.0357 (17)	0.0054 (18)	0.0040 (15)	0.0003 (16)
C17	0.047 (2)	0.071 (2)	0.0347 (17)	−0.0033 (18)	0.0016 (15)	−0.0089 (16)
C18	0.077 (3)	0.059 (2)	0.063 (3)	−0.004 (2)	0.009 (2)	0.019 (2)
C19	0.079 (3)	0.056 (2)	0.075 (3)	−0.011 (2)	−0.033 (3)	−0.001 (2)
C20	0.077 (4)	0.131 (6)	0.122 (5)	−0.005 (4)	0.033 (4)	0.010 (5)
C21	0.055 (3)	0.058 (2)	0.078 (3)	0.003 (2)	0.006 (2)	−0.001 (2)
C22	0.065 (3)	0.092 (4)	0.097 (4)	0.017 (3)	−0.005 (3)	0.012 (3)

C8'—C9'	1.358 (10)	O8—N4	1.234 (4)
C8'—C10'	1.49 (2)	O9—N4	1.212 (4)
C8'—N1	1.559 (17)	O10—N4	1.243 (4)
C8'—H4'	0.9800	O11—N5	1.266 (6)
C9'—H5A	0.9600	O12—N5	1.166 (5)
C9'—H6A	0.9600	O13—N5	1.249 (6)
C9'—H7A	0.9600	O14—C21	1.208 (6)
C10'—N2	1.648 (15)	N1—C7	1.267 (7)
C10'—H8A	0.9700	N2—C11	1.261 (7)
C10'—H9A	0.9700	C1—C2	1.388 (5)
C8—C9	1.414 (9)	C1—C6	1.412 (5)
C8—C10	1.533 (15)	C2—C3	1.373 (5)
C8—N1	1.549 (9)	C3—C4	1.405 (7)
C8—H4	0.9800	C3—H1	0.9300
C9—H5	0.9600	C4—C5	1.350 (8)
C9—H6	0.9600	C4—H2	0.9300
C9—H7	0.9600	C5—C6	1.389 (6)
C10—N2	1.455 (12)	C5—H3	0.9300
C10—H8	0.9700	C6—C7	1.441 (7)
C10—H9	0.9700	C11—C12	1.444 (8)
Sm1—O1	2.390 (2)	C11—H10	0.9300
Sm1—O3	2.394 (2)	C12—C17	1.404 (5)
Sm1—O11	2.467 (4)	C12—C13	1.410 (7)
Sm1—O7	2.481 (3)	C13—C14	1.346 (8)
Sm1—O13	2.486 (4)	C13—H11	0.9300
Sm1—O5	2.517 (3)	C14—C15	1.361 (7)
Sm1—O10	2.533 (3)	C14—H12	0.9300
Sm1—O8	2.551 (3)	C15—C16	1.380 (5)
Sm1—O2	2.621 (3)	C15—H13	0.9300
Sm1—O4	2.639 (3)	C16—C17	1.392 (6)
Sm1—Cu	3.4452 (9)	C18—H14	0.9600
Cu—O3	1.894 (3)	C18—H15	0.9600
Cu—N1	1.905 (4)	C18—H16	0.9600
Cu—O1	1.906 (3)	C19—H17	0.9600
Cu—N2	1.926 (4)	C19—H18	0.9600
Cu—O14	2.616 (4)	C19—H19	0.9600
O1—C1	1.325 (4)	C20—C21	1.495 (8)
O2—C2	1.390 (4)	C20—H20	0.9600
O2—C19	1.438 (5)	C20—H21	0.9600
O3—C17	1.337 (4)	C20—H22	0.9600
O4—C16	1.384 (5)	C21—C22	1.479 (7)
O4—C18	1.435 (5)	C22—H23	0.9600
O5—N3	1.250 (5)	C22—H24	0.9600
O6—N3	1.202 (5)	C22—H25	0.9600
O7—N3	1.271 (4)
C9'—C8'—C10'	81.1 (16)	C2—O2—Sm1	118.0 (2)
C9'—C8'—N1	126.6 (19)	C19—O2—Sm1	125.6 (2)
C10'—C8'—N1	97.1 (12)	C17—O3—Cu	124.7 (2)
C9'—C8'—H4'	114.5	C17—O3—Sm1	128.8 (2)
C10'—C8'—H4'	114.5	Cu—O3—Sm1	106.33 (11)
N1—C8'—H4'	114.5	C16—O4—C18	116.3 (3)
C8'—C9'—H5A	109.4	C16—O4—Sm1	119.0 (2)
C8'—C9'—H6A	109.4	C18—O4—Sm1	124.3 (2)
H5A—C9'—H6A	109.5	N3—O5—Sm1	96.0 (2)
C8'—C9'—H7A	109.6	N3—O7—Sm1	97.1 (2)
H5A—C9'—H7A	109.5	N4—O8—Sm1	97.2 (2)
H6A—C9'—H7A	109.5	N4—O10—Sm1	97.8 (2)
C8'—C10'—N2	107.2 (10)	N5—O11—Sm1	98.6 (3)
C8'—C10'—H8A	110.3	N5—O13—Sm1	98.2 (3)
N2—C10'—H8A	110.3	C21—O14—Cu	136.6 (3)
C8'—C10'—H9A	110.3	C7—N1—C8	124.8 (5)
N2—C10'—H9A	110.3	C7—N1—C8'	116.1 (7)
H8A—C10'—H9A	108.5	C8—N1—C8'	35.8 (6)
C9—C8—C10	106.7 (10)	C7—N1—Cu	126.8 (3)
C9—C8—N1	118.4 (8)	C8—N1—Cu	107.7 (4)
C10—C8—N1	109.0 (6)	C8'—N1—Cu	111.1 (6)
C9—C8—H4	107.4	C11—N2—C10	120.5 (6)
C10—C8—H4	107.4	C11—N2—C10'	126.1 (7)
N1—C8—H4	107.4	C10—N2—C10'	25.3 (6)
N2—C10—C8	100.5 (8)	C11—N2—Cu	125.5 (3)
N2—C10—H8	111.7	C10—N2—Cu	113.2 (5)
C8—C10—H8	111.7	C10'—N2—Cu	106.4 (7)
N2—C10—H9	111.7	O6—N3—O5	122.8 (4)
C8—C10—H9	111.7	O6—N3—O7	121.2 (4)
H8—C10—H9	109.4	O5—N3—O7	115.9 (3)
O1—Sm1—O3	63.26 (9)	O9—N4—O8	122.1 (4)
O1—Sm1—O11	73.56 (14)	O9—N4—O10	121.8 (4)
O3—Sm1—O11	99.22 (14)	O8—N4—O10	116.1 (3)
O1—Sm1—O7	117.70 (10)	O12—N5—O13	124.8 (6)
O3—Sm1—O7	118.33 (10)	O12—N5—O11	122.1 (6)
O11—Sm1—O7	142.13 (14)	O13—N5—O11	113.1 (4)
O1—Sm1—O13	100.85 (12)	O1—C1—C2	116.7 (3)
O3—Sm1—O13	75.16 (13)	O1—C1—C6	124.2 (4)
O11—Sm1—O13	50.10 (14)	C2—C1—C6	119.1 (4)
O7—Sm1—O13	141.33 (11)	C3—C2—C1	121.5 (4)
O1—Sm1—O5	75.31 (10)	C3—C2—O2	124.7 (4)
O3—Sm1—O5	75.62 (10)	C1—C2—O2	113.8 (3)
O11—Sm1—O5	147.14 (14)	C2—C3—C4	118.7 (5)
O7—Sm1—O5	50.62 (9)	C2—C3—H1	120.7
O13—Sm1—O5	148.77 (13)	C4—C3—H1	120.7
O1—Sm1—O10	122.67 (9)	C5—C4—C3	120.4 (4)
O3—Sm1—O10	165.75 (12)	C5—C4—H2	119.8
O11—Sm1—O10	72.23 (16)	C3—C4—H2	119.8
O7—Sm1—O10	71.85 (12)	C4—C5—C6	121.9 (4)
O13—Sm1—O10	90.71 (15)	C4—C5—H3	119.1
O5—Sm1—O10	117.81 (13)	C6—C5—H3	119.1
O1—Sm1—O8	166.37 (12)	C5—C6—C1	118.3 (4)
O3—Sm1—O8	122.28 (10)	C5—C6—C7	117.6 (4)
O11—Sm1—O8	92.93 (15)	C1—C6—C7	124.1 (4)
O7—Sm1—O8	71.98 (12)	N1—C7—C6	124.4 (4)
O13—Sm1—O8	70.68 (14)	N2—C11—C12	125.5 (4)
O5—Sm1—O8	117.56 (12)	N2—C11—H10	117.2
O10—Sm1—O8	48.83 (10)	C12—C11—H10	117.2
O1—Sm1—O2	60.88 (8)	C17—C12—C13	118.1 (5)
O3—Sm1—O2	122.66 (9)	C17—C12—C11	123.8 (4)
O11—Sm1—O2	76.89 (13)	C13—C12—C11	118.1 (4)
O7—Sm1—O2	78.67 (10)	C14—C13—C12	121.2 (5)
O13—Sm1—O2	126.90 (12)	C14—C13—H11	119.4
O5—Sm1—O2	79.01 (11)	C12—C13—H11	119.4
O10—Sm1—O2	67.43 (9)	C13—C14—C15	121.3 (5)
O8—Sm1—O2	115.05 (9)	C13—C14—H12	119.4
O1—Sm1—O4	121.49 (9)	C15—C14—H12	119.4
O3—Sm1—O4	60.90 (9)	C14—C15—C16	119.3 (5)
O11—Sm1—O4	130.92 (13)	C14—C15—H13	120.3
O7—Sm1—O4	76.65 (10)	C16—C15—H13	120.3
O13—Sm1—O4	80.85 (12)	C15—C16—O4	124.6 (4)
O5—Sm1—O4	75.50 (11)	C15—C16—C17	121.4 (4)
O10—Sm1—O4	115.74 (9)	O4—C16—C17	114.0 (3)
O8—Sm1—O4	68.73 (9)	O3—C17—C16	116.8 (3)
O2—Sm1—O4	152.18 (10)	O3—C17—C12	124.6 (4)
O1—Sm1—Cu	32.10 (6)	C16—C17—C12	118.6 (4)
O3—Sm1—Cu	31.84 (6)	O4—C18—H14	109.5
O11—Sm1—Cu	81.50 (12)	O4—C18—H15	109.5
O7—Sm1—Cu	128.37 (6)	H14—C18—H15	109.5
O13—Sm1—Cu	83.23 (11)	O4—C18—H16	109.5
O5—Sm1—Cu	77.75 (7)	H14—C18—H16	109.5
O10—Sm1—Cu	149.93 (8)	H15—C18—H16	109.5
O8—Sm1—Cu	149.58 (8)	O2—C19—H17	109.5
O2—Sm1—Cu	92.91 (6)	O2—C19—H18	109.5
O4—Sm1—Cu	92.42 (6)	H17—C19—H18	109.5
O3—Cu—N1	172.44 (19)	O2—C19—H19	109.5
O3—Cu—O1	82.66 (11)	H17—C19—H19	109.5
N1—Cu—O1	94.96 (16)	H18—C19—H19	109.5
O3—Cu—N2	95.50 (16)	C21—C20—H20	109.5
N1—Cu—N2	86.0 (2)	C21—C20—H21	109.5
O1—Cu—N2	172.76 (17)	H20—C20—H21	109.5
O3—Cu—O14	97.58 (12)	C21—C20—H22	109.5
N1—Cu—O14	89.80 (18)	H20—C20—H22	109.5
O1—Cu—O14	96.32 (13)	H21—C20—H22	109.5
N2—Cu—O14	90.86 (17)	O14—C21—C22	121.1 (5)
O3—Cu—Sm1	41.83 (7)	O14—C21—C20	122.2 (5)
N1—Cu—Sm1	136.67 (14)	C22—C21—C20	116.7 (5)
O1—Cu—Sm1	41.80 (7)	C21—C22—H23	109.5
N2—Cu—Sm1	137.23 (14)	C21—C22—H24	109.5
O14—Cu—Sm1	92.28 (8)	H23—C22—H24	109.5
C1—O1—Cu	125.1 (2)	C21—C22—H25	109.5
C1—O1—Sm1	128.1 (2)	H23—C22—H25	109.5
Cu—O1—Sm1	106.11 (11)	H24—C22—H25	109.5
C2—O2—C19	116.2 (3)