Trichloridotris{N-[phen-yl(pyridin-2-yl)-methyl-idene]hydroxyl-amine-κN,N'}samarium(III).

The Sm(III) ion in the title compound, [SmCl(3)(C(12)H(10)N(2)O)(3)], shows a coordination number of nine with a slightly distorted tricapped trigonal prismatic geometry based on a Cl(3)N(6) donor set. The mol-ecular structure is stabilized by three intra-molecular O-H⋯Cl hydrogen bonds.

Related literature

For related literature on the phenyl-2-pyridyl ketone oxime ligand chelating one n class="Chemical">metal centre, see: Yin & Liu (2009 ▶); Yan & Liu (2009 ▶); Xiang et al. (2006 ▶); Milios et al. (2004 ▶). For the phenyl-2-pyridyl ketone oxime ligand bridging two metals, see: Liu et al.. (2011 ▶); Holynska & Dehnen (2011 ▶); Papatriantafyllopoulou et al. (2007 ▶). For the applications of phenyl-2-pyridyl ketone oxime complexes, see: Korpi et al. (2005 ▶); Stamatatos et al. (2006 ▶).

Experimental

Crystal data

[SmCl3(C12H10N2O)3]

M = 851.37

Triclinic,

a = 8.6415 (17) Å

b = 10.422 (2) Å

c = 19.771 (4) Å

α = 92.18 (3)°

β = 94.47 (3)°

γ = 92.62 (3)°

V = 1771.8 (6) Å3

Z = 2

Mo Kα radiation

μ = 1.93 mm−1

T = 293 K

0.30 × 0.17 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.595, T max = 0.802

32032 measured reflections

8553 independent reflections

7752 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.068

S = 1.04

8553 reflections

445 parameters

H-atom parameters constrained

Δρmax = 0.97 e Å−3

Δρmin = −0.62 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812008100/tk5061sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008100/tk5061Isup2.hkl

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

[SmCl3(C12H10N2O)3]	Z = 2
Mr = 851.37	F(000) = 850
Triclinic, P1	char
Hall symbol: -P 1	Dx = 1.596 Mg m−3
a = 8.6415 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.422 (2) Å	Cell parameters from 8108 reflections
c = 19.771 (4) Å	θ = 2.2–28.1°
α = 92.18 (3)°	µ = 1.93 mm−1
β = 94.47 (3)°	T = 293 K
γ = 92.62 (3)°	Block, colourless
V = 1771.8 (6) Å3	0.30 × 0.17 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	8553 independent reflections
Radiation source: fine-focus sealed tube	7752 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.073
φ and ω scans	θmax = 28.0°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.595, Tmax = 0.802	k = −13→13
32032 measured reflections	l = −26→26

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0279P)2 + 0.2554P] where P = (Fo2 + 2Fc2)/3
8553 reflections	(Δ/σ)max = 0.002
445 parameters	Δρmax = 0.97 e Å−3
0 restraints	Δρmin = −0.62 e Å−3
0 constraints

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
Sm1	0.834137 (13)	0.905657 (10)	0.251022 (6)	0.03257 (5)
Cl2	0.72244 (8)	0.79917 (6)	0.36744 (4)	0.04910 (16)
Cl3	0.51963 (7)	0.92727 (7)	0.22387 (4)	0.05149 (16)
Cl4	0.89706 (9)	1.14430 (6)	0.20005 (4)	0.05223 (16)
N3	1.0834 (2)	0.84667 (18)	0.18255 (11)	0.0400 (5)
N1	0.7598 (2)	1.08550 (19)	0.33380 (11)	0.0420 (5)
N4	1.0201 (2)	0.72192 (18)	0.29251 (11)	0.0395 (5)
O1	0.6146 (2)	1.1365 (2)	0.32620 (12)	0.0609 (6)
H1	0.5629	1.0988	0.2943	0.091*
N2	1.0487 (2)	1.01068 (18)	0.34079 (11)	0.0380 (4)
N5	0.7661 (2)	0.88995 (19)	0.11666 (11)	0.0436 (5)
N6	0.7487 (2)	0.68142 (19)	0.18849 (11)	0.0424 (5)
C24	0.8012 (3)	1.2479 (2)	0.42591 (13)	0.0413 (6)
C28	1.0078 (3)	1.0932 (2)	0.38971 (13)	0.0387 (5)
C30	1.2153 (3)	0.5636 (2)	0.28091 (13)	0.0387 (5)
C34	1.1492 (3)	0.7327 (2)	0.19293 (13)	0.0377 (5)
C36	1.2342 (4)	0.3413 (3)	0.30392 (17)	0.0619 (9)
H36	1.1901	0.2581	0.3022	0.074*
C39	1.1232 (3)	0.6735 (2)	0.25778 (13)	0.0364 (5)
O2	0.7737 (3)	0.99726 (17)	0.07745 (10)	0.0563 (5)
H2	0.8046	1.0603	0.1016	0.084*
C44	0.7355 (3)	0.7852 (2)	0.08127 (13)	0.0421 (6)
C45	0.8487 (3)	1.1408 (2)	0.38184 (13)	0.0388 (5)
C48	1.1171 (3)	0.9060 (3)	0.12670 (14)	0.0492 (7)
H48	1.0781	0.9866	0.1200	0.059*
C49	0.7139 (3)	0.7787 (3)	0.00623 (14)	0.0488 (6)
C50	1.1485 (3)	0.4409 (2)	0.27872 (15)	0.0492 (6)
H50	1.0466	0.4249	0.2605	0.059*
C56	1.2057 (3)	0.8558 (3)	0.07822 (15)	0.0551 (7)
H56	1.2237	0.9005	0.0396	0.066*
C57	1.1961 (3)	0.9757 (2)	0.34498 (14)	0.0430 (6)
H57	1.2273	0.9214	0.3108	0.052*
C58	1.1091 (3)	1.1342 (3)	0.44452 (14)	0.0512 (7)
H58	1.0761	1.1885	0.4784	0.061*
C60	0.7322 (3)	0.5757 (2)	0.22425 (16)	0.0523 (7)
H60	0.7472	0.5842	0.2713	0.063*
C66	0.8616 (4)	1.3709 (2)	0.42052 (15)	0.0540 (7)
H66	0.9350	1.3880	0.3897	0.065*
C67	0.7224 (3)	0.6673 (2)	0.12071 (14)	0.0456 (6)
C68	1.3676 (3)	0.5872 (3)	0.30676 (15)	0.0504 (7)
H68	1.4142	0.6694	0.3069	0.060*
C72	1.4497 (4)	0.4863 (3)	0.33252 (16)	0.0613 (8)
H72	1.5516	0.5014	0.3509	0.074*
C74	0.5744 (4)	0.8370 (3)	−0.09703 (18)	0.0715 (9)
H74	0.4925	0.8773	−0.1194	0.086*
C76	1.3829 (4)	0.3653 (3)	0.33123 (16)	0.0647 (9)
H76	1.4390	0.2987	0.3491	0.078*
C77	1.3042 (3)	1.0162 (3)	0.39746 (15)	0.0516 (7)
H77	1.4059	0.9906	0.3978	0.062*
C78	1.2397 (3)	0.6766 (3)	0.14662 (14)	0.0498 (6)
H78	1.2820	0.5977	0.1549	0.060*
C81	0.6913 (4)	1.2258 (3)	0.47195 (15)	0.0564 (7)
H81	0.6475	1.1433	0.4754	0.068*
C83	0.5899 (3)	0.8375 (3)	−0.02754 (15)	0.0542 (7)
H83	0.5172	0.8774	−0.0027	0.065*
C87	0.8122 (4)	1.4694 (3)	0.46141 (17)	0.0631 (8)
H87	0.8518	1.5528	0.4571	0.076*
C88	0.7077 (4)	1.4467 (3)	0.50742 (17)	0.0643 (8)
H88	0.6778	1.5136	0.5353	0.077*
C89	0.6464 (4)	1.3248 (4)	0.51256 (18)	0.0729 (10)
H89	0.5736	1.3087	0.5438	0.087*
C91	0.6808 (6)	0.7763 (4)	−0.13346 (19)	0.0888 (13)
H91	0.6697	0.7758	−0.1806	0.107*
C92	1.2599 (3)	1.0943 (3)	0.44881 (16)	0.0600 (8)
H92	1.3293	1.1199	0.4857	0.072*
C93	1.2669 (4)	0.7385 (3)	0.08813 (16)	0.0584 (8)
H93	1.3258	0.7013	0.0559	0.070*
C96	0.8206 (4)	0.7178 (3)	−0.03163 (17)	0.0679 (9)
H96	0.9036	0.6780	−0.0098	0.081*
C99	0.8025 (5)	0.7168 (4)	−0.1020 (2)	0.0835 (11)
H99	0.8729	0.6757	−0.1276	0.100*
C100	0.6944 (4)	0.4556 (3)	0.19527 (19)	0.0700 (9)
H100	0.6852	0.3848	0.2222	0.084*
C102	0.6710 (5)	0.4416 (3)	0.1271 (2)	0.0852 (12)
H102	0.6470	0.3608	0.1063	0.102*
C105	0.6830 (4)	0.5498 (3)	0.08822 (18)	0.0718 (9)
H105	0.6648	0.5428	0.0412	0.086*
O3	1.0089 (2)	0.66543 (19)	0.35400 (10)	0.0568 (5)
H3	0.9363	0.6948	0.3729	0.085*

	U11	U22	U33	U12	U13	U23
Sm1	0.03595 (7)	0.02704 (7)	0.03464 (8)	0.00444 (4)	0.00201 (5)	−0.00155 (5)
Cl2	0.0536 (4)	0.0489 (3)	0.0471 (4)	0.0086 (3)	0.0146 (3)	0.0040 (3)
Cl3	0.0391 (3)	0.0587 (4)	0.0548 (4)	0.0054 (3)	−0.0051 (3)	−0.0076 (3)
Cl4	0.0744 (5)	0.0302 (3)	0.0516 (4)	−0.0016 (3)	0.0043 (3)	0.0013 (3)
N3	0.0425 (11)	0.0322 (10)	0.0460 (13)	0.0034 (8)	0.0052 (9)	0.0048 (9)
N1	0.0362 (10)	0.0395 (11)	0.0506 (13)	0.0126 (9)	0.0015 (9)	−0.0053 (10)
N4	0.0457 (11)	0.0351 (10)	0.0391 (12)	0.0082 (9)	0.0066 (9)	0.0065 (9)
O1	0.0432 (11)	0.0652 (13)	0.0720 (15)	0.0236 (9)	−0.0080 (9)	−0.0256 (11)
N2	0.0391 (11)	0.0318 (10)	0.0430 (12)	0.0037 (8)	0.0037 (9)	−0.0021 (9)
N5	0.0520 (12)	0.0377 (11)	0.0409 (12)	0.0028 (9)	0.0027 (10)	0.0020 (9)
N6	0.0485 (12)	0.0326 (10)	0.0461 (13)	−0.0012 (9)	0.0073 (10)	−0.0015 (9)
C24	0.0470 (14)	0.0371 (12)	0.0395 (14)	0.0075 (10)	0.0027 (11)	−0.0068 (11)
C28	0.0429 (13)	0.0330 (12)	0.0404 (14)	0.0036 (10)	0.0035 (11)	0.0002 (10)
C30	0.0434 (13)	0.0342 (12)	0.0401 (14)	0.0112 (10)	0.0086 (11)	0.0028 (10)
C34	0.0402 (12)	0.0327 (11)	0.0403 (14)	0.0009 (9)	0.0038 (10)	−0.0003 (10)
C36	0.089 (2)	0.0353 (14)	0.066 (2)	0.0183 (14)	0.0260 (18)	0.0078 (14)
C39	0.0411 (12)	0.0286 (11)	0.0395 (13)	0.0043 (9)	0.0031 (10)	0.0004 (10)
O2	0.0848 (14)	0.0400 (10)	0.0428 (11)	−0.0019 (10)	−0.0029 (10)	0.0058 (8)
C44	0.0428 (13)	0.0418 (13)	0.0410 (14)	0.0001 (10)	0.0033 (11)	−0.0061 (11)
C45	0.0425 (13)	0.0333 (12)	0.0408 (14)	0.0063 (10)	0.0043 (11)	−0.0031 (10)
C48	0.0502 (15)	0.0446 (14)	0.0546 (17)	0.0031 (11)	0.0083 (13)	0.0147 (13)
C49	0.0559 (16)	0.0494 (15)	0.0398 (15)	−0.0103 (12)	0.0076 (12)	−0.0076 (12)
C50	0.0520 (15)	0.0390 (13)	0.0576 (18)	0.0066 (11)	0.0086 (13)	0.0029 (12)
C56	0.0549 (16)	0.0630 (18)	0.0492 (17)	−0.0003 (14)	0.0125 (14)	0.0134 (14)
C57	0.0387 (13)	0.0377 (12)	0.0529 (16)	0.0060 (10)	0.0048 (11)	−0.0016 (11)
C58	0.0549 (16)	0.0541 (16)	0.0433 (16)	0.0101 (13)	−0.0042 (13)	−0.0101 (13)
C60	0.0598 (17)	0.0394 (14)	0.0585 (18)	−0.0021 (12)	0.0103 (14)	0.0059 (13)
C66	0.0680 (18)	0.0403 (14)	0.0548 (18)	0.0008 (13)	0.0175 (14)	−0.0077 (13)
C67	0.0478 (14)	0.0401 (13)	0.0481 (16)	−0.0031 (11)	0.0060 (12)	−0.0061 (12)
C68	0.0437 (14)	0.0497 (15)	0.0589 (18)	0.0062 (11)	0.0071 (13)	0.0067 (13)
C72	0.0476 (16)	0.082 (2)	0.0579 (19)	0.0258 (15)	0.0084 (14)	0.0096 (16)
C74	0.083 (2)	0.074 (2)	0.054 (2)	−0.0226 (18)	−0.0092 (18)	0.0093 (17)
C76	0.079 (2)	0.0628 (19)	0.060 (2)	0.0431 (17)	0.0238 (17)	0.0182 (16)
C77	0.0392 (14)	0.0551 (16)	0.0597 (19)	0.0068 (12)	−0.0026 (13)	−0.0007 (14)
C78	0.0563 (16)	0.0450 (14)	0.0503 (16)	0.0104 (12)	0.0152 (13)	0.0003 (12)
C81	0.0697 (19)	0.0482 (15)	0.0518 (18)	−0.0029 (14)	0.0162 (15)	−0.0075 (13)
C83	0.0594 (17)	0.0545 (16)	0.0469 (17)	−0.0102 (13)	0.0011 (14)	−0.0011 (13)
C87	0.088 (2)	0.0374 (14)	0.064 (2)	0.0077 (15)	0.0093 (17)	−0.0080 (14)
C88	0.081 (2)	0.0558 (18)	0.057 (2)	0.0181 (16)	0.0106 (17)	−0.0194 (15)
C89	0.081 (2)	0.079 (2)	0.061 (2)	0.0025 (18)	0.0315 (18)	−0.0168 (18)
C91	0.123 (4)	0.098 (3)	0.041 (2)	−0.040 (3)	0.008 (2)	−0.004 (2)
C92	0.0546 (17)	0.0670 (19)	0.0555 (19)	0.0048 (14)	−0.0121 (14)	−0.0055 (15)
C93	0.0653 (19)	0.0602 (18)	0.0526 (18)	0.0054 (14)	0.0235 (15)	−0.0003 (15)
C96	0.064 (2)	0.080 (2)	0.059 (2)	−0.0016 (17)	0.0114 (16)	−0.0135 (17)
C99	0.096 (3)	0.094 (3)	0.061 (2)	−0.014 (2)	0.032 (2)	−0.024 (2)
C100	0.093 (2)	0.0343 (14)	0.082 (3)	−0.0109 (15)	0.018 (2)	0.0003 (16)
C102	0.130 (3)	0.0441 (18)	0.080 (3)	−0.0266 (19)	0.022 (2)	−0.0168 (18)
C105	0.102 (3)	0.0493 (17)	0.061 (2)	−0.0202 (17)	0.0121 (19)	−0.0149 (16)
O3	0.0663 (13)	0.0632 (12)	0.0468 (11)	0.0267 (10)	0.0195 (10)	0.0191 (10)

Sm1—N1	2.578 (2)	C56—H56	0.9300
Sm1—N2	2.634 (2)	C57—C77	1.381 (4)
Sm1—N6	2.649 (2)	C57—H57	0.9300
Sm1—N4	2.668 (2)	C58—C92	1.384 (4)
Sm1—N5	2.673 (2)	C58—H58	0.9300
Sm1—N3	2.713 (2)	C60—C100	1.371 (4)
Sm1—Cl3	2.7501 (9)	C60—H60	0.9300
Sm1—Cl4	2.7658 (9)	C66—C87	1.386 (4)
Sm1—Cl2	2.8114 (10)	C66—H66	0.9300
N3—C48	1.331 (3)	C67—C105	1.378 (4)
N3—C34	1.356 (3)	C68—C72	1.386 (4)
N1—C45	1.276 (3)	C68—H68	0.9300
N1—O1	1.385 (2)	C72—C76	1.361 (5)
N4—C39	1.276 (3)	C72—H72	0.9300
N4—O3	1.379 (3)	C74—C91	1.373 (5)
O1—H1	0.8200	C74—C83	1.370 (4)
N2—C57	1.338 (3)	C74—H74	0.9300
N2—C28	1.348 (3)	C76—H76	0.9300
N5—C44	1.280 (3)	C77—C92	1.366 (4)
N5—O2	1.387 (3)	C77—H77	0.9300
N6—C60	1.340 (3)	C78—C93	1.376 (4)
N6—C67	1.343 (3)	C78—H78	0.9300
C24—C66	1.373 (4)	C81—C89	1.372 (4)
C24—C81	1.384 (4)	C81—H81	0.9300
C24—C45	1.482 (3)	C83—H83	0.9300
C28—C58	1.380 (4)	C87—C88	1.350 (4)
C28—C45	1.482 (3)	C87—H87	0.9300
C30—C50	1.377 (4)	C88—C89	1.365 (5)
C30—C68	1.381 (4)	C88—H88	0.9300
C30—C39	1.490 (3)	C89—H89	0.9300
C34—C78	1.380 (3)	C91—C99	1.366 (6)
C34—C39	1.472 (3)	C91—H91	0.9300
C36—C76	1.363 (5)	C92—H92	0.9300
C36—C50	1.388 (4)	C93—H93	0.9300
C36—H36	0.9300	C96—C99	1.388 (5)
O2—H2	0.8200	C96—H96	0.9300
C44—C49	1.479 (4)	C99—H99	0.9300
C44—C67	1.484 (4)	C100—C102	1.349 (5)
C48—C56	1.376 (4)	C100—H100	0.9300
C48—H48	0.9300	C102—C105	1.393 (5)
C49—C96	1.392 (4)	C102—H102	0.9300
C49—C83	1.397 (4)	C105—H105	0.9300
C50—H50	0.9300	O3—H3	0.8200
C56—C93	1.369 (4)
N1—Sm1—N2	60.96 (6)	C96—C49—C83	119.2 (3)
N1—Sm1—N6	146.13 (7)	C96—C49—C44	120.2 (3)
N2—Sm1—N6	140.66 (6)	C83—C49—C44	120.5 (2)
N1—Sm1—N4	121.34 (7)	C30—C50—C36	119.5 (3)
N2—Sm1—N4	71.97 (7)	C30—C50—H50	120.2
N6—Sm1—N4	68.71 (7)	C36—C50—H50	120.2
N1—Sm1—N5	126.41 (7)	C93—C56—C48	118.5 (3)
N2—Sm1—N5	139.50 (7)	C93—C56—H56	120.7
N6—Sm1—N5	59.63 (7)	C48—C56—H56	120.7
N4—Sm1—N5	111.97 (7)	N2—C57—C77	123.4 (2)
N1—Sm1—N3	137.56 (7)	N2—C57—H57	118.3
N2—Sm1—N3	83.11 (7)	C77—C57—H57	118.3
N6—Sm1—N3	76.24 (7)	C28—C58—C92	119.6 (3)
N4—Sm1—N3	59.12 (6)	C28—C58—H58	120.2
N5—Sm1—N3	67.77 (7)	C92—C58—H58	120.2
N1—Sm1—Cl3	74.68 (6)	N6—C60—C100	123.6 (3)
N2—Sm1—Cl3	135.50 (5)	N6—C60—H60	118.2
N6—Sm1—Cl3	77.87 (5)	C100—C60—H60	118.2
N4—Sm1—Cl3	136.25 (5)	C24—C66—C87	119.5 (3)
N5—Sm1—Cl3	70.91 (6)	C24—C66—H66	120.3
N3—Sm1—Cl3	138.19 (5)	C87—C66—H66	120.3
N1—Sm1—Cl4	69.59 (5)	N6—C67—C105	122.4 (3)
N2—Sm1—Cl4	76.92 (5)	N6—C67—C44	117.1 (2)
N6—Sm1—Cl4	130.98 (5)	C105—C67—C44	120.5 (3)
N4—Sm1—Cl4	131.71 (5)	C30—C68—C72	118.9 (3)
N5—Sm1—Cl4	71.60 (5)	C30—C68—H68	120.5
N3—Sm1—Cl4	81.51 (5)	C72—C68—H68	120.5
Cl3—Sm1—Cl4	91.54 (4)	C76—C72—C68	120.7 (3)
N1—Sm1—Cl2	69.82 (5)	C76—C72—H72	119.6
N2—Sm1—Cl2	82.21 (5)	C68—C72—H72	119.6
N6—Sm1—Cl2	86.06 (5)	C91—C74—C83	119.4 (4)
N4—Sm1—Cl2	71.06 (5)	C91—C74—H74	120.3
N5—Sm1—Cl2	138.12 (5)	C83—C74—H74	120.3
N3—Sm1—Cl2	130.19 (5)	C72—C76—C36	120.4 (3)
Cl3—Sm1—Cl2	79.46 (3)	C72—C76—H76	119.8
Cl4—Sm1—Cl2	139.37 (3)	C36—C76—H76	119.8
C48—N3—C34	116.5 (2)	C92—C77—C57	119.2 (3)
C48—N3—Sm1	121.95 (16)	C92—C77—H77	120.4
C34—N3—Sm1	118.93 (16)	C57—C77—H77	120.4
C45—N1—O1	113.35 (19)	C93—C78—C34	119.4 (2)
C45—N1—Sm1	126.08 (15)	C93—C78—H78	120.3
O1—N1—Sm1	120.47 (15)	C34—C78—H78	120.3
C39—N4—O3	112.88 (18)	C89—C81—C24	120.4 (3)
C39—N4—Sm1	124.81 (16)	C89—C81—H81	119.8
O3—N4—Sm1	122.25 (13)	C24—C81—H81	119.8
N1—O1—H1	109.5	C74—C83—C49	120.5 (3)
C57—N2—C28	117.1 (2)	C74—C83—H83	119.8
C57—N2—Sm1	122.81 (16)	C49—C83—H83	119.8
C28—N2—Sm1	119.70 (15)	C88—C87—C66	121.4 (3)
C44—N5—O2	113.0 (2)	C88—C87—H87	119.3
C44—N5—Sm1	124.96 (17)	C66—C87—H87	119.3
O2—N5—Sm1	121.83 (14)	C87—C88—C89	119.3 (3)
C60—N6—C67	117.1 (2)	C87—C88—H88	120.3
C60—N6—Sm1	120.33 (18)	C89—C88—H88	120.3
C67—N6—Sm1	122.54 (16)	C88—C89—C81	120.5 (3)
C66—C24—C81	118.8 (2)	C88—C89—H89	119.7
C66—C24—C45	120.9 (2)	C81—C89—H89	119.7
C81—C24—C45	120.2 (2)	C99—C91—C74	121.5 (3)
N2—C28—C58	122.2 (2)	C99—C91—H91	119.2
N2—C28—C45	117.1 (2)	C74—C91—H91	119.2
C58—C28—C45	120.7 (2)	C77—C92—C58	118.3 (3)
C50—C30—C68	120.3 (2)	C77—C92—H92	120.9
C50—C30—C39	120.6 (2)	C58—C92—H92	120.9
C68—C30—C39	119.1 (2)	C56—C93—C78	118.8 (3)
N3—C34—C78	122.3 (2)	C56—C93—H93	120.6
N3—C34—C39	116.2 (2)	C78—C93—H93	120.6
C78—C34—C39	121.5 (2)	C99—C96—C49	119.7 (3)
C76—C36—C50	120.1 (3)	C99—C96—H96	120.1
C76—C36—H36	119.9	C49—C96—H96	120.1
C50—C36—H36	119.9	C91—C99—C96	119.7 (4)
N4—C39—C34	116.61 (19)	C91—C99—H99	120.2
N4—C39—C30	122.7 (2)	C96—C99—H99	120.2
C34—C39—C30	120.7 (2)	C102—C100—C60	119.0 (3)
N5—O2—H2	109.5	C102—C100—H100	120.5
N5—C44—C49	123.6 (2)	C60—C100—H100	120.5
N5—C44—C67	115.4 (2)	C100—C102—C105	119.1 (3)
C49—C44—C67	121.1 (2)	C100—C102—H102	120.4
N1—C45—C28	115.1 (2)	C105—C102—H102	120.4
N1—C45—C24	123.6 (2)	C67—C105—C102	118.8 (3)
C28—C45—C24	121.3 (2)	C67—C105—H105	120.6
N3—C48—C56	124.3 (2)	C102—C105—H105	120.6
N3—C48—H48	117.9	N4—O3—H3	109.5
C56—C48—H48	117.9

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl3	0.82	2.22	2.960 (2)	150
O2—H2···Cl4	0.82	2.18	2.920 (2)	150
O3—H3···Cl2	0.82	2.18	2.920 (2)	149

Table 1

Selected bond lengths (Å)

Sm1—N1	2.578 (2)
Sm1—N2	2.634 (2)
Sm1—N6	2.649 (2)
Sm1—N4	2.668 (2)
Sm1—N5	2.673 (2)
Sm1—N3	2.713 (2)
Sm1—Cl3	2.7501 (9)
Sm1—Cl4	2.7658 (9)
Sm1—Cl2	2.8114 (10)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Cl3	0.82	2.22	2.960 (2)	150
O2—H2⋯Cl4	0.82	2.18	2.920 (2)	150
O3—H3⋯Cl2	0.82	2.18	2.920 (2)	149