Tris[6-meth-oxy-2-(phenyl-iminiometh-yl)phenolato]-κO,O';κO-tris-(thio-cyanato-κN)samarium(III).

In the crystal structure of title compound, [Sm(NCS)(3)(C(14)H(13)NO(2))(3)], two of the zwitterionic Schiff base 6-meth-oxy-2-(phenyl-iminiometh-yl)phenolate ligands coordinate to the Sm(III) atom in a bidentate fashion via the phenolate and meth-oxy O atoms. The third Schiff base ligand is monodentate, binding only through the phenolate O atom. The coordination sphere of the eight-coordinate Sm atom is completed by the three independent thio-cyanate ions binding through their N atoms, affording a square-anti-prismatic geometry. An S atom of one of the thio-cyanate anions is disordered over two sites in a 0.85:0.15 ratio. In the phenolate ligands, the proton of the phenolic hy-droxy group transfers to the imine N atom. This proton is also involved in an intra-molecular N-H⋯O hydrogen bond that imposes a nearly planar conformation on each ligand, with dihedral angles of 1.75 (4), 3.68 (5) and 3.86 (4)° between the aromatic rings of each ligand.

Related literature

For related La(III) and Tb(III) complexes, see: Liu et al. (2009 ▶); Zhao et al. (2007 ▶). For a coordination polymer derived from the same ligand, see: Li et al. (2008 ▶). For other complexes of N-salicyl­idene­amino acids, see: Burrows & Bailar (1966 ▶). For the synthesis of rare earth complexes with Schiff bases derived from o-vanillin and adamantane­amine, see: Zhao et al. (2005 ▶) and for chiral lanthanide La(III), Ce(III), Eu(III) complexes with macrocyclic Schiff bases, see: Mazurek & Lisowski (2003 ▶).

Experimental

Crystal data

[Sm(NCS)3(C14H13NO2)3]

M = 1006.35

Orthorhombic,

a = 19.5821 (13) Å

b = 20.3531 (14) Å

c = 22.4764 (16) Å

V = 8958.1 (11) Å3

Z = 8

Mo Kα radiation

μ = 1.51 mm−1

T = 296 K

0.19 × 0.11 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.820, T max = 0.879

44977 measured reflections

10202 independent reflections

5925 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.077

S = 0.99

10202 reflections

562 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; 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/S1600536811016205/sj5128sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016205/sj5128Isup2.hkl

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

[Sm(NCS)3(C14H13NO2)3]	F(000) = 4072
Mr = 1006.35	Dx = 1.492 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8408 reflections
a = 19.5821 (13) Å	θ = 1.7–27.4°
b = 20.3531 (14) Å	µ = 1.51 mm−1
c = 22.4764 (16) Å	T = 296 K
V = 8958.1 (11) Å3	Block, red
Z = 8	0.19 × 0.11 × 0.09 mm

Bruker APEXII CCD diffractometer	10202 independent reflections
Radiation source: fine-focus sealed tube	5925 reflections with I > 2σ(I)
graphite	Rint = 0.046
φ and ω scans	θmax = 27.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→17
Tmin = 0.820, Tmax = 0.879	k = −17→26
44977 measured reflections	l = −29→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0276P)2P] where P = (Fo2 + 2Fc2)/3
10202 reflections	(Δ/σ)max = 0.002
562 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.48 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)
Sm1	0.386756 (8)	0.065497 (8)	0.674038 (7)	0.04009 (7)
C1	0.38840 (17)	−0.1108 (2)	0.69993 (17)	0.0559 (10)
C2	0.38077 (16)	0.18885 (17)	0.55898 (17)	0.0472 (9)
C3	0.2424 (2)	0.01245 (19)	0.58901 (18)	0.0649 (12)
C4	0.23106 (19)	0.17975 (19)	0.67437 (17)	0.0808 (13)
H4A	0.1855	0.1693	0.6869	0.121*
H4B	0.2365	0.1684	0.6332	0.121*
H4C	0.2391	0.2259	0.6795	0.121*
C5	0.27647 (16)	0.14943 (18)	0.77058 (17)	0.0470 (9)
C6	0.24777 (16)	0.20102 (18)	0.8016 (2)	0.0601 (11)
H6	0.2249	0.2343	0.7815	0.072*
C7	0.25349 (19)	0.2027 (2)	0.8639 (2)	0.0636 (12)
H7	0.2345	0.2376	0.8849	0.076*
C8	0.28607 (19)	0.1547 (2)	0.89360 (19)	0.0645 (11)
H8	0.2898	0.1571	0.9348	0.077*
C9	0.31460 (17)	0.10066 (19)	0.86309 (17)	0.0494 (9)
C10	0.30971 (15)	0.09743 (18)	0.80081 (17)	0.0435 (9)
C11	0.35044 (19)	0.0510 (2)	0.89350 (18)	0.0596 (11)
H11	0.3550	0.0546	0.9346	0.072*
C12	0.4210 (2)	−0.0509 (2)	0.8890 (2)	0.0647 (11)
C13	0.4511 (2)	−0.0488 (2)	0.9441 (2)	0.0906 (14)
H13	0.4418	−0.0149	0.9706	0.109*
C14	0.4343 (3)	−0.1015 (3)	0.8512 (2)	0.0960 (15)
H14	0.4125	−0.1034	0.8144	0.115*
C18	0.5674 (2)	0.16708 (17)	0.65924 (17)	0.0792 (13)
H18A	0.5378	0.1974	0.6794	0.119*
H18B	0.5886	0.1887	0.6261	0.119*
H18C	0.6019	0.1518	0.6863	0.119*
C19	0.56142 (17)	0.06593 (17)	0.60434 (15)	0.0441 (8)
C20	0.62817 (16)	0.06757 (17)	0.58762 (16)	0.0523 (10)
H20	0.6559	0.1021	0.5998	0.063*
C21	0.65513 (17)	0.01726 (19)	0.55211 (16)	0.0569 (10)
H21	0.7006	0.0190	0.5402	0.068*
C22	0.61540 (16)	−0.03382 (19)	0.53513 (16)	0.0523 (9)
H22	0.6336	−0.0670	0.5115	0.063*
C23	0.54599 (16)	−0.03695 (17)	0.55328 (14)	0.0414 (8)
C24	0.51804 (16)	0.01387 (17)	0.58791 (15)	0.0428 (9)
C25	0.50616 (16)	−0.09166 (17)	0.53564 (14)	0.0452 (9)
H25	0.5263	−0.1231	0.5113	0.054*
C26	0.53626 (17)	−0.02210 (17)	0.73674 (17)	0.0710 (12)
H26A	0.5346	−0.0500	0.7712	0.106*
H26B	0.5818	−0.0055	0.7318	0.106*
H26C	0.5234	−0.0469	0.7021	0.106*
C27	0.50429 (16)	0.07603 (17)	0.78924 (16)	0.0442 (9)
C28	0.47831 (17)	0.18348 (17)	0.82938 (16)	0.0473 (9)
C29	0.54684 (18)	0.06406 (19)	0.83630 (17)	0.0602 (11)
H29	0.5698	0.0242	0.8388	0.072*
C30	0.5558 (2)	0.1110 (2)	0.88003 (18)	0.0734 (12)
H30	0.5852	0.1025	0.9116	0.088*
C31	0.5223 (2)	0.1691 (2)	0.87766 (17)	0.0712 (12)
H31	0.5282	0.1998	0.9079	0.085*
C32	0.46979 (15)	0.13687 (17)	0.78335 (15)	0.0408 (8)
C33	0.44407 (19)	0.24441 (18)	0.82642 (17)	0.0592 (10)
H33	0.4499	0.2740	0.8575	0.071*
C34	0.36501 (17)	0.31872 (19)	0.7765 (2)	0.0561 (10)
C35	0.3451 (2)	0.3563 (2)	0.8245 (2)	0.0721 (12)
H35	0.3588	0.3453	0.8628	0.086*
C36	0.34359 (19)	0.33435 (19)	0.7203 (2)	0.0698 (12)
H36	0.3575	0.3089	0.6881	0.084*
C37	0.3013 (2)	0.3878 (2)	0.7112 (2)	0.0921 (15)
H37	0.2855	0.3977	0.6732	0.111*
C38	0.39794 (16)	−0.15331 (17)	0.53783 (14)	0.0436 (9)
C39	0.41983 (17)	−0.20829 (17)	0.50737 (15)	0.0523 (10)
H39	0.4647	−0.2117	0.4942	0.063*
C40	0.33179 (17)	−0.14836 (18)	0.55728 (15)	0.0553 (10)
H40	0.3175	−0.1110	0.5777	0.066*
C41	0.2829 (2)	0.4263 (2)	0.7592 (3)	0.0990 (19)
H41	0.2557	0.4632	0.7535	0.119*
C42	0.3046 (2)	0.4104 (2)	0.8146 (3)	0.0956 (17)
H42	0.2919	0.4366	0.8466	0.115*
C43	0.28665 (18)	−0.1986 (2)	0.54662 (17)	0.0650 (11)
H43	0.2418	−0.1955	0.5599	0.078*
C44	0.3076 (2)	−0.2534 (2)	0.51645 (17)	0.0627 (11)
H44	0.2771	−0.2875	0.5093	0.075*
C45	0.37362 (19)	−0.25807 (18)	0.49683 (17)	0.0619 (11)
H45	0.3875	−0.2953	0.4761	0.074*
N1	0.37935 (14)	−0.05526 (14)	0.69309 (14)	0.0592 (9)
N2	0.38159 (15)	0.15884 (15)	0.60278 (15)	0.0626 (9)
N3	0.28872 (16)	0.03283 (15)	0.61340 (14)	0.0638 (9)
N4	0.37735 (15)	0.00056 (16)	0.86737 (14)	0.0589 (9)
H4N	0.3672	−0.0028	0.8303	0.071*
N5	0.40494 (13)	0.26107 (13)	0.78251 (13)	0.0496 (8)
H5N	0.4029	0.2337	0.7534	0.059*
N6	0.44248 (13)	−0.10033 (13)	0.55171 (11)	0.0451 (7)
H6N	0.4253	−0.0699	0.5736	0.054*
O1	0.33589 (11)	0.04926 (10)	0.76964 (9)	0.0477 (6)
O2	0.27958 (11)	0.14291 (12)	0.70981 (11)	0.0606 (7)
O3	0.52826 (11)	0.11233 (12)	0.63829 (11)	0.0593 (7)
O4	0.45412 (10)	0.01339 (10)	0.60439 (10)	0.0506 (6)
O5	0.48975 (11)	0.03197 (11)	0.74444 (11)	0.0536 (6)
O6	0.43125 (10)	0.14810 (9)	0.73654 (9)	0.0413 (5)
S1	0.40327 (6)	−0.18882 (5)	0.70832 (6)	0.0935 (4)
S2	0.37988 (5)	0.23007 (5)	0.49660 (5)	0.0640 (3)
S3	0.17603 (7)	−0.02499 (10)	0.55935 (7)	0.0962 (5)	0.85
S3'	0.1863 (4)	0.0303 (5)	0.5308 (4)	0.081 (3)	0.15
C17	0.4967 (3)	−0.0997 (3)	0.9590 (3)	0.1057 (18)
H17	0.5171	−0.0999	0.9963	0.127*
C16	0.5111 (3)	−0.1476 (3)	0.9205 (3)	0.112 (2)
H16	0.5428	−0.1797	0.9305	0.134*
C15	0.4796 (3)	−0.1498 (3)	0.8670 (3)	0.118 (2)
H15	0.4888	−0.1841	0.8409	0.142*

	U11	U22	U33	U12	U13	U23
Sm1	0.04677 (11)	0.04036 (12)	0.03315 (11)	0.00306 (9)	0.00068 (9)	−0.00664 (9)
C1	0.057 (2)	0.057 (3)	0.054 (3)	0.002 (2)	−0.001 (2)	−0.011 (2)
C2	0.043 (2)	0.048 (2)	0.051 (3)	0.0075 (18)	0.0031 (19)	−0.010 (2)
C3	0.057 (3)	0.077 (3)	0.060 (3)	0.015 (2)	−0.004 (2)	−0.023 (2)
C4	0.072 (3)	0.094 (3)	0.077 (3)	0.024 (3)	−0.020 (2)	0.003 (3)
C5	0.040 (2)	0.053 (2)	0.048 (3)	−0.0033 (19)	0.0100 (18)	−0.006 (2)
C6	0.048 (2)	0.056 (3)	0.076 (3)	0.000 (2)	0.018 (2)	−0.005 (2)
C7	0.060 (3)	0.059 (3)	0.072 (4)	−0.008 (2)	0.030 (2)	−0.026 (3)
C8	0.060 (3)	0.078 (3)	0.055 (3)	−0.016 (2)	0.015 (2)	−0.022 (3)
C9	0.050 (2)	0.058 (3)	0.041 (3)	−0.006 (2)	0.0101 (19)	−0.004 (2)
C10	0.040 (2)	0.047 (2)	0.044 (2)	−0.0097 (18)	0.0076 (17)	−0.009 (2)
C11	0.060 (2)	0.075 (3)	0.043 (3)	−0.012 (2)	0.010 (2)	−0.007 (2)
C12	0.069 (3)	0.078 (3)	0.048 (3)	−0.009 (3)	0.000 (2)	0.021 (3)
C13	0.086 (3)	0.117 (4)	0.069 (4)	−0.003 (3)	−0.008 (3)	0.006 (3)
C14	0.144 (5)	0.076 (4)	0.069 (4)	0.017 (4)	−0.001 (3)	0.001 (3)
C18	0.099 (3)	0.056 (3)	0.083 (3)	−0.028 (2)	0.024 (3)	−0.019 (2)
C19	0.049 (2)	0.045 (2)	0.038 (2)	0.001 (2)	−0.0007 (17)	−0.0071 (19)
C20	0.045 (2)	0.061 (3)	0.051 (3)	−0.0131 (19)	−0.0001 (17)	−0.005 (2)
C21	0.039 (2)	0.071 (3)	0.061 (3)	−0.003 (2)	0.0064 (19)	−0.002 (2)
C22	0.044 (2)	0.057 (2)	0.056 (3)	0.003 (2)	0.0033 (19)	−0.008 (2)
C23	0.0390 (19)	0.049 (2)	0.036 (2)	−0.0021 (18)	0.0006 (16)	−0.0018 (19)
C24	0.042 (2)	0.051 (2)	0.035 (2)	−0.0018 (19)	0.0049 (17)	−0.0018 (19)
C25	0.045 (2)	0.050 (2)	0.040 (2)	0.0088 (19)	0.0064 (17)	−0.0029 (19)
C26	0.072 (3)	0.064 (3)	0.077 (3)	0.028 (2)	0.001 (2)	0.000 (2)
C27	0.0412 (19)	0.050 (2)	0.042 (2)	0.0030 (18)	0.0001 (17)	0.003 (2)
C28	0.055 (2)	0.046 (2)	0.041 (2)	−0.0047 (19)	−0.0063 (19)	0.000 (2)
C29	0.057 (2)	0.064 (3)	0.060 (3)	0.000 (2)	−0.012 (2)	0.009 (2)
C30	0.079 (3)	0.082 (3)	0.059 (3)	0.002 (3)	−0.029 (2)	0.009 (3)
C31	0.093 (3)	0.074 (3)	0.046 (3)	−0.003 (3)	−0.029 (2)	−0.013 (2)
C32	0.0366 (19)	0.046 (2)	0.039 (2)	−0.0080 (17)	0.0003 (17)	0.0024 (19)
C33	0.069 (3)	0.055 (3)	0.053 (3)	−0.008 (2)	−0.008 (2)	−0.008 (2)
C34	0.051 (2)	0.041 (2)	0.076 (3)	−0.0066 (19)	−0.003 (2)	−0.007 (2)
C35	0.072 (3)	0.057 (3)	0.087 (3)	0.007 (2)	−0.001 (2)	−0.024 (3)
C36	0.067 (3)	0.062 (3)	0.080 (4)	0.010 (2)	−0.008 (3)	−0.006 (3)
C37	0.083 (3)	0.079 (4)	0.115 (5)	0.011 (3)	−0.036 (3)	0.000 (3)
C38	0.044 (2)	0.048 (2)	0.038 (2)	−0.0058 (18)	−0.0022 (16)	−0.0033 (18)
C39	0.049 (2)	0.048 (2)	0.060 (3)	−0.0038 (19)	−0.0063 (19)	−0.006 (2)
C40	0.048 (2)	0.063 (3)	0.055 (3)	−0.005 (2)	0.0050 (19)	−0.011 (2)
C41	0.067 (3)	0.061 (3)	0.169 (6)	0.012 (2)	−0.027 (4)	−0.024 (4)
C42	0.073 (3)	0.071 (4)	0.142 (6)	0.006 (3)	−0.005 (3)	−0.044 (4)
C43	0.049 (2)	0.084 (3)	0.062 (3)	−0.014 (2)	0.003 (2)	−0.006 (3)
C44	0.062 (3)	0.067 (3)	0.059 (3)	−0.017 (2)	−0.019 (2)	0.003 (2)
C45	0.067 (3)	0.049 (3)	0.069 (3)	−0.001 (2)	−0.009 (2)	−0.007 (2)
N1	0.069 (2)	0.046 (2)	0.063 (2)	0.0055 (17)	0.0125 (16)	−0.0055 (17)
N2	0.070 (2)	0.066 (2)	0.052 (2)	0.0013 (17)	−0.0009 (18)	0.0064 (19)
N3	0.063 (2)	0.069 (2)	0.059 (2)	−0.0020 (19)	−0.0075 (18)	−0.0119 (19)
N4	0.067 (2)	0.070 (2)	0.040 (2)	−0.0049 (19)	0.0010 (17)	0.0039 (19)
N5	0.0502 (18)	0.0411 (19)	0.057 (2)	−0.0014 (15)	−0.0027 (16)	−0.0063 (16)
N6	0.0447 (16)	0.0482 (18)	0.0425 (19)	−0.0017 (15)	0.0058 (14)	−0.0098 (15)
O1	0.0552 (14)	0.0450 (14)	0.0430 (15)	−0.0002 (12)	0.0069 (12)	−0.0081 (12)
O2	0.0634 (16)	0.0774 (18)	0.0409 (17)	0.0180 (14)	−0.0021 (13)	−0.0037 (14)
O3	0.0580 (15)	0.0552 (16)	0.0645 (18)	−0.0069 (14)	0.0082 (13)	−0.0191 (14)
O4	0.0408 (13)	0.0598 (16)	0.0513 (16)	−0.0045 (12)	0.0109 (11)	−0.0150 (13)
O5	0.0544 (14)	0.0504 (15)	0.0559 (17)	0.0158 (13)	−0.0083 (13)	−0.0085 (14)
O6	0.0449 (13)	0.0418 (13)	0.0371 (14)	0.0018 (11)	−0.0036 (11)	−0.0021 (12)
S1	0.1156 (10)	0.0449 (7)	0.1200 (11)	0.0103 (6)	−0.0151 (8)	−0.0014 (7)
S2	0.0645 (6)	0.0674 (7)	0.0601 (7)	0.0146 (5)	0.0041 (5)	0.0142 (6)
S3	0.0590 (9)	0.1447 (15)	0.0849 (13)	0.0049 (11)	−0.0177 (8)	−0.0495 (12)
S3'	0.057 (5)	0.120 (7)	0.067 (6)	0.022 (5)	−0.031 (4)	−0.042 (6)
C17	0.088 (4)	0.134 (5)	0.095 (5)	0.009 (4)	−0.019 (3)	0.049 (4)
C16	0.113 (4)	0.103 (5)	0.120 (6)	0.024 (4)	0.029 (4)	0.049 (4)
C15	0.163 (6)	0.088 (4)	0.104 (5)	0.037 (4)	0.006 (4)	0.025 (4)

Sm1—O4	2.305 (2)	C23—C25	1.416 (4)
Sm1—O6	2.358 (2)	C24—O4	1.306 (3)
Sm1—O1	2.391 (2)	C25—N6	1.310 (3)
Sm1—N3	2.447 (3)	C25—H25	0.9300
Sm1—N2	2.487 (3)	C26—O5	1.439 (3)
Sm1—N1	2.499 (3)	C26—H26A	0.9600
Sm1—O5	2.653 (2)	C26—H26B	0.9600
Sm1—O2	2.745 (2)	C26—H26C	0.9600
C1—N1	1.155 (4)	C27—C29	1.368 (4)
C1—S1	1.625 (4)	C27—O5	1.378 (4)
C2—N2	1.159 (4)	C27—C32	1.417 (4)
C2—S2	1.634 (4)	C28—C33	1.411 (4)
C3—N3	1.139 (4)	C28—C32	1.414 (4)
C3—S3	1.647 (4)	C28—C31	1.415 (4)
C3—S3'	1.746 (8)	C29—C30	1.381 (5)
C4—O2	1.449 (4)	C29—H29	0.9300
C4—H4A	0.9600	C30—C31	1.355 (5)
C4—H4B	0.9600	C30—H30	0.9300
C4—H4C	0.9600	C31—H31	0.9300
C5—O2	1.374 (4)	C32—O6	1.315 (3)
C5—C6	1.380 (4)	C33—N5	1.295 (4)
C5—C10	1.416 (4)	C33—H33	0.9300
C6—C7	1.405 (5)	C34—C36	1.367 (5)
C6—H6	0.9300	C34—C35	1.379 (5)
C7—C8	1.345 (5)	C34—N5	1.416 (4)
C7—H7	0.9300	C35—C42	1.374 (5)
C8—C9	1.411 (5)	C35—H35	0.9300
C8—H8	0.9300	C36—C37	1.382 (5)
C9—C10	1.405 (4)	C36—H36	0.9300
C9—C11	1.407 (5)	C37—C41	1.382 (6)
C10—O1	1.310 (4)	C37—H37	0.9300
C11—N4	1.295 (4)	C38—C40	1.371 (4)
C11—H11	0.9300	C38—C39	1.380 (4)
C12—C14	1.361 (5)	C38—N6	1.422 (4)
C12—C13	1.372 (5)	C39—C45	1.379 (4)
C12—N4	1.436 (5)	C39—H39	0.9300
C13—C17	1.408 (6)	C40—C43	1.373 (4)
C13—H13	0.9300	C40—H40	0.9300
C14—C15	1.371 (6)	C41—C42	1.355 (6)
C14—H14	0.9300	C41—H41	0.9300
C18—O3	1.432 (4)	C42—H42	0.9300
C18—H18A	0.9600	C43—C44	1.369 (5)
C18—H18B	0.9600	C43—H43	0.9300
C18—H18C	0.9600	C44—C45	1.369 (4)
C19—C20	1.360 (4)	C44—H44	0.9300
C19—O3	1.377 (3)	C45—H45	0.9300
C19—C24	1.407 (4)	N4—H4N	0.8600
C20—C21	1.402 (4)	N5—H5N	0.8600
C20—H20	0.9300	N6—H6N	0.8600
C21—C22	1.354 (4)	C17—C16	1.333 (6)
C21—H21	0.9300	C17—H17	0.9300
C22—C23	1.421 (4)	C16—C15	1.351 (7)
C22—H22	0.9300	C16—H16	0.9300
C23—C24	1.405 (4)	C15—H15	0.9300
O4—Sm1—O6	121.41 (7)	C23—C25—H25	118.2
O4—Sm1—O1	141.71 (7)	O5—C26—H26A	109.5
O6—Sm1—O1	73.57 (7)	O5—C26—H26B	109.5
O4—Sm1—N3	86.89 (9)	H26A—C26—H26B	109.5
O6—Sm1—N3	144.66 (9)	O5—C26—H26C	109.5
O1—Sm1—N3	97.83 (9)	H26A—C26—H26C	109.5
O4—Sm1—N2	86.41 (9)	H26B—C26—H26C	109.5
O6—Sm1—N2	81.60 (9)	C29—C27—O5	125.1 (3)
O1—Sm1—N2	131.86 (9)	C29—C27—C32	121.2 (4)
N3—Sm1—N2	79.45 (10)	O5—C27—C32	113.7 (3)
O4—Sm1—N1	72.37 (9)	C33—C28—C32	119.9 (3)
O6—Sm1—N1	128.36 (9)	C33—C28—C31	120.4 (4)
O1—Sm1—N1	71.69 (8)	C32—C28—C31	119.6 (3)
N3—Sm1—N1	77.45 (10)	C27—C29—C30	120.3 (4)
N2—Sm1—N1	149.24 (10)	C27—C29—H29	119.9
O4—Sm1—O5	81.47 (7)	C30—C29—H29	119.9
O6—Sm1—O5	63.07 (7)	C31—C30—C29	121.0 (4)
O1—Sm1—O5	75.23 (7)	C31—C30—H30	119.5
N3—Sm1—O5	149.21 (9)	C29—C30—H30	119.5
N2—Sm1—O5	127.70 (8)	C30—C31—C28	120.3 (4)
N1—Sm1—O5	71.88 (9)	C30—C31—H31	119.8
O4—Sm1—O2	154.22 (8)	C28—C31—H31	119.8
O6—Sm1—O2	72.46 (7)	O6—C32—C28	122.5 (3)
O1—Sm1—O2	59.84 (7)	O6—C32—C27	120.0 (3)
N3—Sm1—O2	73.69 (9)	C28—C32—C27	117.5 (3)
N2—Sm1—O2	73.68 (9)	N5—C33—C28	123.2 (3)
N1—Sm1—O2	118.03 (8)	N5—C33—H33	118.4
O5—Sm1—O2	123.66 (7)	C28—C33—H33	118.4
N1—C1—S1	178.2 (4)	C36—C34—C35	120.4 (4)
N2—C2—S2	179.1 (3)	C36—C34—N5	116.8 (4)
N3—C3—S3	172.8 (4)	C35—C34—N5	122.7 (4)
N3—C3—S3'	141.8 (5)	C42—C35—C34	118.8 (4)
S3—C3—S3'	45.4 (3)	C42—C35—H35	120.6
O2—C4—H4A	109.5	C34—C35—H35	120.6
O2—C4—H4B	109.5	C34—C36—C37	120.3 (4)
H4A—C4—H4B	109.5	C34—C36—H36	119.9
O2—C4—H4C	109.5	C37—C36—H36	119.9
H4A—C4—H4C	109.5	C41—C37—C36	119.1 (5)
H4B—C4—H4C	109.5	C41—C37—H37	120.4
O2—C5—C6	126.4 (4)	C36—C37—H37	120.4
O2—C5—C10	112.6 (3)	C40—C38—C39	120.7 (3)
C6—C5—C10	120.9 (4)	C40—C38—N6	117.0 (3)
C5—C6—C7	119.3 (4)	C39—C38—N6	122.2 (3)
C5—C6—H6	120.3	C45—C39—C38	118.5 (3)
C7—C6—H6	120.3	C45—C39—H39	120.7
C8—C7—C6	121.0 (4)	C38—C39—H39	120.7
C8—C7—H7	119.5	C38—C40—C43	119.9 (3)
C6—C7—H7	119.5	C38—C40—H40	120.1
C7—C8—C9	120.9 (4)	C43—C40—H40	120.1
C7—C8—H8	119.6	C42—C41—C37	120.0 (5)
C9—C8—H8	119.6	C42—C41—H41	120.0
C10—C9—C11	119.0 (4)	C37—C41—H41	120.0
C10—C9—C8	119.6 (4)	C41—C42—C35	121.4 (5)
C11—C9—C8	121.4 (4)	C41—C42—H42	119.3
O1—C10—C9	122.8 (4)	C35—C42—H42	119.3
O1—C10—C5	118.9 (3)	C44—C43—C40	120.0 (4)
C9—C10—C5	118.3 (4)	C44—C43—H43	120.0
N4—C11—C9	123.5 (4)	C40—C43—H43	120.0
N4—C11—H11	118.2	C43—C44—C45	120.0 (4)
C9—C11—H11	118.2	C43—C44—H44	120.0
C14—C12—C13	120.3 (5)	C45—C44—H44	120.0
C14—C12—N4	117.0 (4)	C44—C45—C39	120.9 (4)
C13—C12—N4	122.6 (5)	C44—C45—H45	119.5
C12—C13—C17	117.6 (5)	C39—C45—H45	119.5
C12—C13—H13	121.2	C1—N1—Sm1	167.7 (3)
C17—C13—H13	121.2	C2—N2—Sm1	161.9 (3)
C12—C14—C15	120.3 (5)	C3—N3—Sm1	173.1 (3)
C12—C14—H14	119.9	C11—N4—C12	131.8 (4)
C15—C14—H14	119.9	C11—N4—H4N	114.1
O3—C18—H18A	109.5	C12—N4—H4N	114.1
O3—C18—H18B	109.5	C33—N5—C34	128.1 (3)
H18A—C18—H18B	109.5	C33—N5—H5N	116.0
O3—C18—H18C	109.5	C34—N5—H5N	116.0
H18A—C18—H18C	109.5	C25—N6—C38	128.7 (3)
H18B—C18—H18C	109.5	C25—N6—H6N	115.6
C20—C19—O3	126.1 (3)	C38—N6—H6N	115.6
C20—C19—C24	121.7 (3)	C10—O1—Sm1	122.7 (2)
O3—C19—C24	112.2 (3)	C5—O2—C4	117.9 (3)
C19—C20—C21	120.1 (3)	C5—O2—Sm1	112.4 (2)
C19—C20—H20	120.0	C4—O2—Sm1	129.6 (2)
C21—C20—H20	120.0	C19—O3—C18	117.6 (3)
C22—C21—C20	120.4 (3)	C24—O4—Sm1	137.6 (2)
C22—C21—H21	119.8	C27—O5—C26	117.1 (3)
C20—C21—H21	119.8	C27—O5—Sm1	115.19 (18)
C21—C22—C23	120.2 (3)	C26—O5—Sm1	127.3 (2)
C21—C22—H22	119.9	C32—O6—Sm1	124.4 (2)
C23—C22—H22	119.9	C16—C17—C13	121.2 (6)
C24—C23—C25	121.3 (3)	C16—C17—H17	119.4
C24—C23—C22	119.9 (3)	C13—C17—H17	119.4
C25—C23—C22	118.8 (3)	C17—C16—C15	120.3 (6)
O4—C24—C23	121.7 (3)	C17—C16—H16	119.9
O4—C24—C19	120.7 (3)	C15—C16—H16	119.9
C23—C24—C19	117.7 (3)	C16—C15—C14	120.2 (6)
N6—C25—C23	123.6 (3)	C16—C15—H15	119.9
N6—C25—H25	118.2	C14—C15—H15	119.9
O2—C5—C6—C7	−175.1 (3)	O5—Sm1—N2—C2	106.9 (9)
C10—C5—C6—C7	1.9 (5)	O2—Sm1—N2—C2	−132.8 (9)
C5—C6—C7—C8	−0.4 (5)	C9—C11—N4—C12	172.7 (3)
C6—C7—C8—C9	−0.9 (5)	C14—C12—N4—C11	172.7 (4)
C7—C8—C9—C10	0.8 (5)	C13—C12—N4—C11	−10.2 (6)
C7—C8—C9—C11	178.2 (3)	C28—C33—N5—C34	175.8 (3)
C11—C9—C10—O1	1.5 (5)	C36—C34—N5—C33	161.9 (4)
C8—C9—C10—O1	179.0 (3)	C35—C34—N5—C33	−21.3 (5)
C11—C9—C10—C5	−176.9 (3)	C23—C25—N6—C38	−178.8 (3)
C8—C9—C10—C5	0.6 (5)	C40—C38—N6—C25	−175.9 (3)
O2—C5—C10—O1	−3.0 (4)	C39—C38—N6—C25	5.5 (5)
C6—C5—C10—O1	179.6 (3)	C9—C10—O1—Sm1	−143.4 (2)
O2—C5—C10—C9	175.4 (3)	C5—C10—O1—Sm1	35.0 (4)
C6—C5—C10—C9	−1.9 (5)	O4—Sm1—O1—C10	166.8 (2)
C10—C9—C11—N4	−2.7 (5)	O6—Sm1—O1—C10	46.5 (2)
C8—C9—C11—N4	179.9 (3)	N3—Sm1—O1—C10	−98.3 (2)
C14—C12—C13—C17	1.3 (6)	N2—Sm1—O1—C10	−15.5 (3)
N4—C12—C13—C17	−175.7 (4)	N1—Sm1—O1—C10	−172.3 (2)
C13—C12—C14—C15	−2.1 (7)	O5—Sm1—O1—C10	112.3 (2)
N4—C12—C14—C15	175.0 (4)	O2—Sm1—O1—C10	−32.4 (2)
O3—C19—C20—C21	−179.1 (3)	C6—C5—O2—C4	−21.7 (5)
C24—C19—C20—C21	1.3 (5)	C10—C5—O2—C4	161.1 (3)
C19—C20—C21—C22	−1.2 (5)	C6—C5—O2—Sm1	154.3 (3)
C20—C21—C22—C23	−0.1 (5)	C10—C5—O2—Sm1	−22.9 (3)
C21—C22—C23—C24	1.4 (5)	O4—Sm1—O2—C5	179.93 (19)
C21—C22—C23—C25	−178.9 (3)	O6—Sm1—O2—C5	−53.0 (2)
C25—C23—C24—O4	−1.2 (5)	O1—Sm1—O2—C5	27.8 (2)
C22—C23—C24—O4	178.6 (3)	N3—Sm1—O2—C5	137.3 (2)
C25—C23—C24—C19	179.0 (3)	N2—Sm1—O2—C5	−139.2 (2)
C22—C23—C24—C19	−1.3 (5)	N1—Sm1—O2—C5	71.7 (2)
C20—C19—C24—O4	−179.9 (3)	O5—Sm1—O2—C5	−14.4 (2)
O3—C19—C24—O4	0.4 (4)	O4—Sm1—O2—C4	−4.7 (4)
C20—C19—C24—C23	0.0 (5)	O6—Sm1—O2—C4	122.3 (3)
O3—C19—C24—C23	−179.7 (3)	O1—Sm1—O2—C4	−156.8 (3)
C24—C23—C25—N6	−2.7 (5)	N3—Sm1—O2—C4	−47.3 (3)
C22—C23—C25—N6	177.6 (3)	N2—Sm1—O2—C4	36.2 (3)
O5—C27—C29—C30	−177.5 (3)	N1—Sm1—O2—C4	−113.0 (3)
C32—C27—C29—C30	1.5 (5)	O5—Sm1—O2—C4	161.0 (3)
C27—C29—C30—C31	0.7 (6)	C20—C19—O3—C18	−1.3 (5)
C29—C30—C31—C28	−1.3 (6)	C24—C19—O3—C18	178.4 (3)
C33—C28—C31—C30	−179.1 (4)	C23—C24—O4—Sm1	163.2 (2)
C32—C28—C31—C30	−0.4 (5)	C19—C24—O4—Sm1	−16.9 (5)
C33—C28—C32—O6	0.8 (5)	O6—Sm1—O4—C24	3.3 (3)
C31—C28—C32—O6	−178.0 (3)	O1—Sm1—O4—C24	−100.5 (3)
C33—C28—C32—C27	−178.8 (3)	N3—Sm1—O4—C24	160.8 (3)
C31—C28—C32—C27	2.5 (5)	N2—Sm1—O4—C24	81.2 (3)
C29—C27—C32—O6	177.4 (3)	N1—Sm1—O4—C24	−121.4 (3)
O5—C27—C32—O6	−3.5 (4)	O5—Sm1—O4—C24	−47.8 (3)
C29—C27—C32—C28	−3.1 (5)	O2—Sm1—O4—C24	120.2 (3)
O5—C27—C32—C28	176.1 (3)	C29—C27—O5—C26	−18.8 (5)
C32—C28—C33—N5	−1.0 (5)	C32—C27—O5—C26	162.1 (3)
C31—C28—C33—N5	177.8 (3)	C29—C27—O5—Sm1	168.3 (3)
C36—C34—C35—C42	−1.4 (6)	C32—C27—O5—Sm1	−10.7 (3)
N5—C34—C35—C42	−178.0 (3)	O4—Sm1—O5—C27	145.8 (2)
C35—C34—C36—C37	−0.4 (6)	O6—Sm1—O5—C27	13.97 (19)
N5—C34—C36—C37	176.4 (3)	O1—Sm1—O5—C27	−64.8 (2)
C34—C36—C37—C41	2.1 (6)	N3—Sm1—O5—C27	−145.2 (2)
C40—C38—C39—C45	0.1 (5)	N2—Sm1—O5—C27	67.1 (2)
N6—C38—C39—C45	178.6 (3)	N1—Sm1—O5—C27	−140.0 (2)
C39—C38—C40—C43	0.2 (5)	O2—Sm1—O5—C27	−27.9 (2)
N6—C38—C40—C43	−178.4 (3)	O4—Sm1—O5—C26	−26.2 (2)
C36—C37—C41—C42	−1.9 (7)	O6—Sm1—O5—C26	−158.1 (3)
C37—C41—C42—C35	0.1 (8)	O1—Sm1—O5—C26	123.1 (2)
C34—C35—C42—C41	1.5 (7)	N3—Sm1—O5—C26	42.8 (3)
C38—C40—C43—C44	−0.2 (5)	N2—Sm1—O5—C26	−104.9 (3)
C40—C43—C44—C45	−0.1 (6)	N1—Sm1—O5—C26	47.9 (2)
C43—C44—C45—C39	0.5 (6)	O2—Sm1—O5—C26	160.0 (2)
C38—C39—C45—C44	−0.5 (5)	C28—C32—O6—Sm1	−160.2 (2)
O4—Sm1—N1—C1	41.7 (14)	C27—C32—O6—Sm1	19.3 (4)
O6—Sm1—N1—C1	−74.8 (14)	O4—Sm1—O6—C32	−76.9 (2)
O1—Sm1—N1—C1	−124.8 (14)	O1—Sm1—O6—C32	64.2 (2)
N3—Sm1—N1—C1	132.4 (14)	N3—Sm1—O6—C32	144.4 (2)
N2—Sm1—N1—C1	90.2 (14)	N2—Sm1—O6—C32	−157.5 (2)
O5—Sm1—N1—C1	−44.9 (14)	N1—Sm1—O6—C32	14.9 (2)
O2—Sm1—N1—C1	−164.0 (14)	O5—Sm1—O6—C32	−17.2 (2)
O4—Sm1—N2—C2	30.6 (9)	O2—Sm1—O6—C32	127.1 (2)
O6—Sm1—N2—C2	153.1 (9)	C12—C13—C17—C16	1.2 (7)
O1—Sm1—N2—C2	−148.0 (9)	C13—C17—C16—C15	−2.9 (9)
N3—Sm1—N2—C2	−56.9 (9)	C17—C16—C15—C14	2.0 (9)
N1—Sm1—N2—C2	−15.1 (10)	C12—C14—C15—C16	0.5 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···O1	0.86	1.83	2.543 (4)	139
N5—H5N···O6	0.86	1.87	2.573 (3)	131
N6—H6N···O4	0.86	1.92	2.610 (3)	137

Table 1

Selected bond lengths (Å)

Sm1—O4	2.305 (2)
Sm1—O6	2.358 (2)
Sm1—O1	2.391 (2)
Sm1—N3	2.447 (3)
Sm1—N2	2.487 (3)
Sm1—N1	2.499 (3)
Sm1—O5	2.653 (2)
Sm1—O2	2.745 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4N⋯O1	0.86	1.83	2.543 (4)	139
N5—H5N⋯O6	0.86	1.87	2.573 (3)	131
N6—H6N⋯O4	0.86	1.92	2.610 (3)	137