Tris(2-formyl­phenolato-κ2O,O′)(1,10-phenanthroline-κ2N,N′)samarium(III)

Zhong, Y.; Yang, J.; Hu, L.

doi:10.1107/S1600536813016139

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page m430

doi:10.1107/S1600536813016139

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Tris(2-formylphenolato-κ²O,O′)(1,10-phenanthroline-κ²N,N′)samarium(III)

Yun Zhong,^a ^* Jinbing Yang ^a and Ling Hu ^a

^aSchool of Basical Science, East China Jiaotong University, Nanchang 330013, People's Republic of China
^*Correspondence e-mail: zhongyun1973@126.com

(Received 30 May 2013; accepted 10 June 2013; online 3 July 2013)

In the title compound, [Sm(C₇H₅O₂)₃(C₁₂H₈N₂)], the Sm^III cation is coordinated by six O atoms from three bidentate 2-formylphenolate ligands and by two N atoms from 1,10-phenanthroline ligand. The resulting SmN₂O6 coordination polyhedron is a distorted square antiprism. In the crystal, C—H⋯O interactions connect molecules into chains along the b-axis direction. In addition, π–π stacking interactions are observed with centroid–centroid distances in the range 3.6422 (13)–3.7329 (13) Å.

Related literature

For the structures of metal complexes with 2-formylphenolate ligands, see: Li & Chen (2006 ); Li et al. (2007 ); Xiao & Zhang (2008 ); Yang et al. (2007 ).

Experimental

Crystal data

[Sm(C₇H₅O₂)₃(C₁₂H₈N₂)]
M_r = 693.88
Monoclinic, C 2/c
a = 24.1921 (9) Å
b = 14.6474 (6) Å
c = 17.4681 (7) Å
β = 115.28°
V = 5596.8 (4) Å³
Z = 8
Mo Kα radiation
μ = 2.15 mm⁻¹
T = 298 K
0.35 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.520, T_max = 0.673
20817 measured reflections
5066 independent reflections
4612 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.017
wR(F²) = 0.049
S = 1.09
5066 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Selected bond lengths (Å)

N1—Sm1	2.6398 (18)
N2—Sm1	2.602 (2)
O1—Sm1	2.2906 (16)
O2—Sm1	2.4977 (16)
O3—Sm1	2.2925 (15)
O4—Sm1	2.4714 (18)
O5—Sm1	2.3025 (15)
O6—Sm1	2.4888 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯O6ⁱ	0.93	2.46	3.326 (3)	154
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813016139/ff2109sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813016139/ff2109Isup2.hkl

checkCIF report

Comment top

Many metal complexes with Schiff base ligands, which had been synthesized by salicylaldehyde and amine, have been reported. However, only a few metal complexes with 2-formylphenolate ligands had been reported so far. In metal complexes with 2-formylphenolate ligands, the metal ion had been likely coordinated by O atoms from bidentate 2-formylphenolate ligands in a square-planar geometry.(Li et al.,2006; Yang et al., 2007; Xiao & Zhang, 2008; Li et al., 2007)

The title compound, [Sm(C₇H₅O₂)₃(C₁₂H₈N₂)], was obtained by the reaction of salicylaldehyde, 1,10-phenanthroline and samarium(III) chloride in methanol. The Sm^III cation is coordinated by six O atoms from three bidentate 2-formylphenolate ligands and by two N atoms from 1,10-phenanthroline ligand. The Sm—O distances range from 2.2906 (16) to 2.4977 (16) Å, and the Sm—N distances range from 2.602 (2) to 2.6398 (18) Å.

Related literature top

For the structures of metal complexes with 2-formylphenolate ligands, see: Li & Chen (2006); Li et al. (2007); Xiao & Zhang (2008); Yang et al. (2007).

Experimental top

SmCl₃(0.26 g, 1.0 mmol), salicylaldehyde (0.37 g, 3.0 mmol) and triethylamine (0.3 g, 3 mmol) was stirred for 1 h in methanol (20 ml) at reflux temperature and cooled to room temperature. To this solution, a methanol solution (5 ml) containing 1,10-phenanthroline (0.18 g, 1 mmol) was added. The mixture was stirred for 1 h at room temperature and the precipitate was filtered off. Brown crystals were obtained by a slow evaporation of the filtrate.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids for non-H atoms.

Tris(2-formylphenolato-κ²O,O')(1,10-phenanthroline-κ²N,N')samarium(III) top

Crystal data top

[Sm(C₇H₅O₂)₃(C₁₂H₈N₂)]	F(000) = 2760
M_r = 693.88	D_x = 1.647 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9986 reflections
a = 24.1921 (9) Å	θ = 2.3–28.4°
b = 14.6474 (6) Å	µ = 2.15 mm⁻¹
c = 17.4681 (7) Å	T = 298 K
β = 115.28°	Prism, brown
V = 5596.8 (4) Å³	0.35 × 0.30 × 0.20 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	5066 independent reflections
Radiation source: fine-focus sealed tube	4612 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
phi and ω scans	θ_max = 25.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→28
T_min = 0.520, T_max = 0.673	k = −17→17
20817 measured reflections	l = −20→20

Refinement top

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)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.049	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0247P)² + 4.8252P] where P = (F_o² + 2F_c²)/3
5066 reflections	(Δ/σ)_max = 0.001
379 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Sm(C₇H₅O₂)₃(C₁₂H₈N₂)]	V = 5596.8 (4) Å³
M_r = 693.88	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.1921 (9) Å	µ = 2.15 mm⁻¹
b = 14.6474 (6) Å	T = 298 K
c = 17.4681 (7) Å	0.35 × 0.30 × 0.20 mm
β = 115.28°

Data collection top

Bruker SMART CCD area-detector diffractometer	5066 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4612 reflections with I > 2σ(I)
T_min = 0.520, T_max = 0.673	R_int = 0.017
20817 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.017	0 restraints
wR(F²) = 0.049	H-atom parameters constrained
S = 1.09	Δρ_max = 0.44 e Å⁻³
5066 reflections	Δρ_min = −0.32 e Å⁻³
379 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.31169 (10)	0.86165 (16)	0.37537 (16)	0.0465 (5)
H1	0.3199	0.8625	0.3280	0.056*
C2	0.35943 (11)	0.84125 (17)	0.45406 (17)	0.0528 (6)
H2	0.3985	0.8294	0.4585	0.063*
C3	0.34823 (11)	0.83896 (16)	0.52364 (16)	0.0518 (6)
H3	0.3796	0.8258	0.5764	0.062*
C4	0.28917 (11)	0.85648 (14)	0.51595 (14)	0.0433 (5)
C5	0.27276 (13)	0.85179 (16)	0.58590 (15)	0.0536 (6)
H5	0.3027	0.8387	0.6398	0.064*
C6	0.21547 (13)	0.86576 (17)	0.57504 (16)	0.0560 (6)
H6	0.2062	0.8621	0.6214	0.067*
C7	0.16799 (12)	0.88631 (16)	0.49350 (16)	0.0485 (6)
C8	0.10657 (14)	0.89827 (19)	0.4777 (2)	0.0629 (7)
H8	0.0953	0.8947	0.5222	0.075*
C9	0.06353 (14)	0.9149 (2)	0.3984 (2)	0.0679 (8)
H9	0.0227	0.9222	0.3878	0.081*
C10	0.08197 (13)	0.9208 (2)	0.3334 (2)	0.0635 (8)
H10	0.0524	0.9330	0.2790	0.076*
C11	0.18228 (10)	0.89213 (14)	0.42354 (15)	0.0395 (5)
C12	0.24393 (10)	0.87700 (13)	0.43492 (13)	0.0365 (5)
C13	0.08129 (10)	0.71970 (16)	0.16434 (16)	0.0470 (5)
C14	0.02349 (12)	0.68030 (19)	0.1451 (2)	0.0747 (9)
H14	−0.0062	0.7149	0.1522	0.090*
C15	0.01027 (15)	0.59231 (19)	0.1162 (3)	0.0831 (11)
H15	−0.0285	0.5691	0.1032	0.100*
C16	0.05290 (14)	0.53738 (19)	0.1060 (2)	0.0723 (9)
H16	0.0429	0.4782	0.0853	0.087*
C17	0.10973 (14)	0.57144 (17)	0.12672 (18)	0.0596 (7)
H17	0.1390	0.5344	0.1210	0.071*
C18	0.12548 (10)	0.66124 (15)	0.15659 (14)	0.0424 (5)
C19	0.18756 (11)	0.68770 (16)	0.18207 (16)	0.0486 (6)
H19	0.2133	0.6433	0.1770	0.058*
C20	0.27639 (11)	0.93203 (15)	0.14703 (15)	0.0424 (5)
C21	0.33951 (11)	0.94760 (18)	0.17270 (17)	0.0511 (6)
H21	0.3624	0.9743	0.2251	0.061*
C22	0.36752 (14)	0.92430 (19)	0.1224 (2)	0.0651 (8)
H22	0.4093	0.9343	0.1419	0.078*
C23	0.33551 (17)	0.8860 (3)	0.0428 (2)	0.0798 (10)
H23	0.3554	0.8703	0.0094	0.096*
C24	0.27492 (16)	0.8721 (3)	0.0150 (2)	0.0764 (9)
H24	0.2530	0.8480	−0.0388	0.092*
C25	0.24352 (13)	0.89319 (18)	0.06522 (16)	0.0534 (6)
C26	0.17925 (14)	0.8767 (2)	0.03053 (17)	0.0634 (7)
H26	0.1611	0.8570	−0.0254	0.076*
C27	0.06299 (10)	1.08986 (14)	0.14602 (15)	0.0391 (5)
C28	0.00641 (11)	1.11852 (17)	0.08153 (17)	0.0509 (6)
H28	−0.0168	1.0774	0.0395	0.061*
C29	−0.01491 (13)	1.20557 (19)	0.0797 (2)	0.0681 (8)
H29	−0.0522	1.2224	0.0363	0.082*
C30	0.01791 (14)	1.2692 (2)	0.1412 (3)	0.0832 (10)
H30	0.0025	1.3276	0.1400	0.100*
C31	0.07337 (14)	1.24430 (19)	0.2038 (2)	0.0715 (8)
H31	0.0958	1.2868	0.2449	0.086*
C32	0.09729 (10)	1.15610 (16)	0.20742 (15)	0.0457 (5)
C33	0.15714 (11)	1.13771 (18)	0.27111 (16)	0.0525 (6)
H33	0.1758	1.1851	0.3088	0.063*
N1	0.25528 (8)	0.87989 (12)	0.36524 (11)	0.0394 (4)
N2	0.13901 (9)	0.91009 (13)	0.34420 (13)	0.0469 (5)
O1	0.09273 (7)	0.80347 (11)	0.18874 (13)	0.0598 (5)
O2	0.21128 (7)	0.76192 (11)	0.20986 (11)	0.0520 (4)
O3	0.25049 (7)	0.95453 (11)	0.19573 (9)	0.0441 (4)
O4	0.14503 (8)	0.88545 (14)	0.06560 (11)	0.0590 (4)
O5	0.08275 (7)	1.00738 (10)	0.14640 (10)	0.0466 (4)
O6	0.18739 (8)	1.06706 (11)	0.28260 (11)	0.0519 (4)
Sm1	0.165805 (5)	0.913618 (7)	0.214933 (7)	0.03584 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0328 (12)	0.0541 (14)	0.0520 (14)	0.0006 (10)	0.0175 (10)	0.0100 (11)
C2	0.0300 (12)	0.0578 (14)	0.0624 (16)	−0.0004 (10)	0.0120 (11)	0.0116 (12)
C3	0.0409 (13)	0.0494 (13)	0.0483 (14)	−0.0062 (10)	0.0030 (11)	0.0079 (11)
C4	0.0469 (13)	0.0336 (11)	0.0414 (12)	−0.0087 (9)	0.0112 (10)	−0.0009 (9)
C5	0.0689 (18)	0.0470 (13)	0.0371 (13)	−0.0123 (12)	0.0152 (12)	−0.0046 (10)
C6	0.0786 (19)	0.0516 (14)	0.0466 (14)	−0.0115 (13)	0.0353 (14)	−0.0101 (11)
C7	0.0618 (16)	0.0388 (11)	0.0531 (14)	−0.0061 (11)	0.0322 (13)	−0.0078 (10)
C8	0.0698 (19)	0.0687 (17)	0.0714 (19)	−0.0014 (14)	0.0505 (17)	−0.0100 (14)
C9	0.0515 (17)	0.081 (2)	0.087 (2)	0.0063 (14)	0.0441 (17)	−0.0033 (16)
C10	0.0419 (15)	0.088 (2)	0.0653 (18)	0.0100 (13)	0.0270 (14)	0.0082 (14)
C11	0.0443 (13)	0.0318 (10)	0.0471 (13)	−0.0019 (9)	0.0239 (11)	−0.0010 (9)
C12	0.0380 (11)	0.0287 (10)	0.0408 (12)	−0.0051 (8)	0.0151 (9)	0.0001 (8)
C13	0.0374 (12)	0.0413 (12)	0.0581 (14)	−0.0017 (10)	0.0164 (11)	0.0016 (10)
C14	0.0397 (14)	0.0526 (15)	0.126 (3)	−0.0060 (12)	0.0298 (16)	−0.0042 (17)
C15	0.0470 (17)	0.0553 (18)	0.121 (3)	−0.0153 (13)	0.0111 (18)	0.0009 (17)
C16	0.0662 (19)	0.0404 (14)	0.084 (2)	−0.0048 (13)	0.0068 (16)	−0.0043 (13)
C17	0.0625 (17)	0.0431 (13)	0.0621 (17)	0.0061 (12)	0.0162 (14)	−0.0036 (11)
C18	0.0422 (12)	0.0395 (11)	0.0407 (12)	0.0028 (9)	0.0131 (10)	0.0030 (9)
C19	0.0441 (13)	0.0457 (13)	0.0558 (14)	0.0096 (11)	0.0212 (11)	0.0013 (11)
C20	0.0467 (13)	0.0407 (11)	0.0424 (12)	0.0048 (10)	0.0214 (11)	0.0114 (9)
C21	0.0454 (14)	0.0561 (14)	0.0552 (15)	0.0038 (11)	0.0246 (12)	0.0108 (12)
C22	0.0542 (17)	0.0742 (19)	0.079 (2)	0.0143 (13)	0.0403 (16)	0.0225 (15)
C23	0.083 (2)	0.103 (2)	0.077 (2)	0.024 (2)	0.056 (2)	0.0081 (19)
C24	0.081 (2)	0.102 (2)	0.0538 (17)	0.0125 (19)	0.0354 (16)	−0.0070 (16)
C25	0.0563 (16)	0.0635 (15)	0.0414 (13)	0.0075 (12)	0.0220 (12)	0.0021 (11)
C26	0.0644 (18)	0.0795 (19)	0.0384 (14)	0.0023 (15)	0.0143 (13)	−0.0093 (13)
C27	0.0354 (11)	0.0417 (12)	0.0431 (12)	0.0006 (9)	0.0195 (10)	0.0004 (9)
C28	0.0374 (12)	0.0518 (13)	0.0578 (15)	0.0042 (11)	0.0149 (11)	0.0007 (11)
C29	0.0426 (15)	0.0593 (17)	0.091 (2)	0.0128 (12)	0.0182 (15)	0.0096 (15)
C30	0.0615 (19)	0.0500 (16)	0.130 (3)	0.0175 (14)	0.034 (2)	−0.0042 (18)
C31	0.0613 (18)	0.0531 (16)	0.097 (2)	−0.0012 (13)	0.0307 (17)	−0.0223 (15)
C32	0.0397 (12)	0.0462 (12)	0.0526 (14)	−0.0019 (10)	0.0211 (11)	−0.0069 (10)
C33	0.0495 (14)	0.0513 (14)	0.0524 (14)	−0.0113 (12)	0.0179 (12)	−0.0159 (11)
N1	0.0321 (9)	0.0423 (9)	0.0424 (10)	−0.0011 (8)	0.0145 (8)	0.0068 (8)
N2	0.0340 (10)	0.0582 (12)	0.0500 (12)	0.0033 (8)	0.0193 (9)	0.0071 (9)
O1	0.0401 (9)	0.0434 (9)	0.1014 (15)	−0.0057 (7)	0.0356 (10)	−0.0149 (9)
O2	0.0372 (9)	0.0495 (10)	0.0678 (11)	0.0019 (7)	0.0211 (8)	−0.0022 (8)
O3	0.0427 (9)	0.0518 (9)	0.0408 (8)	−0.0062 (7)	0.0207 (7)	−0.0004 (7)
O4	0.0445 (10)	0.0777 (12)	0.0443 (10)	−0.0014 (9)	0.0089 (8)	−0.0070 (9)
O5	0.0371 (8)	0.0414 (8)	0.0482 (9)	0.0040 (7)	0.0056 (7)	−0.0046 (7)
O6	0.0391 (9)	0.0502 (9)	0.0532 (10)	−0.0047 (7)	0.0071 (8)	−0.0056 (8)
Sm1	0.02721 (7)	0.03827 (7)	0.03935 (8)	−0.00068 (4)	0.01164 (5)	0.00116 (4)

Geometric parameters (Å, º) top

C1—N1	1.326 (3)	C19—H19	0.9300
C1—C2	1.399 (3)	C20—O3	1.296 (3)
C1—H1	0.9300	C20—C21	1.414 (3)
C2—C3	1.354 (4)	C20—C25	1.424 (4)
C2—H2	0.9300	C21—C22	1.363 (4)
C3—C4	1.400 (3)	C21—H21	0.9300
C3—H3	0.9300	C22—C23	1.387 (5)
C4—C12	1.403 (3)	C22—H22	0.9300
C4—C5	1.439 (3)	C23—C24	1.348 (5)
C5—C6	1.332 (4)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.418 (4)
C6—C7	1.429 (4)	C24—H24	0.9300
C6—H6	0.9300	C25—C26	1.428 (4)
C7—C8	1.401 (4)	C26—O4	1.229 (3)
C7—C11	1.407 (3)	C26—H26	0.9300
C8—C9	1.352 (5)	C27—O5	1.298 (3)
C8—H8	0.9300	C27—C28	1.415 (3)
C9—C10	1.390 (4)	C27—C32	1.421 (3)
C9—H9	0.9300	C28—C29	1.371 (4)
C10—N2	1.320 (3)	C28—H28	0.9300
C10—H10	0.9300	C29—C30	1.387 (4)
C11—N2	1.359 (3)	C29—H29	0.9300
C11—C12	1.435 (3)	C30—C31	1.369 (4)
C12—N1	1.358 (3)	C30—H30	0.9300
C13—O1	1.290 (3)	C31—C32	1.406 (4)
C13—C14	1.414 (3)	C31—H31	0.9300
C13—C18	1.421 (3)	C32—C33	1.425 (3)
C14—C15	1.371 (4)	C33—O6	1.233 (3)
C14—H14	0.9300	C33—H33	0.9300
C15—C16	1.379 (5)	N1—Sm1	2.6398 (18)
C15—H15	0.9300	N2—Sm1	2.602 (2)
C16—C17	1.358 (4)	O1—Sm1	2.2906 (16)
C16—H16	0.9300	O2—Sm1	2.4977 (16)
C17—C18	1.406 (3)	O3—Sm1	2.2925 (15)
C17—H17	0.9300	O4—Sm1	2.4714 (18)
C18—C19	1.426 (3)	O5—Sm1	2.3025 (15)
C19—O2	1.228 (3)	O6—Sm1	2.4888 (16)

N1—C1—C2	123.0 (2)	C23—C24—H24	118.9
N1—C1—H1	118.5	C25—C24—H24	118.9
C2—C1—H1	118.5	C24—C25—C20	119.4 (3)
C3—C2—C1	119.3 (2)	C24—C25—C26	118.4 (3)
C3—C2—H2	120.3	C20—C25—C26	122.2 (2)
C1—C2—H2	120.3	O4—C26—C25	127.9 (2)
C2—C3—C4	119.8 (2)	O4—C26—H26	116.0
C2—C3—H3	120.1	C25—C26—H26	116.0
C4—C3—H3	120.1	O5—C27—C28	120.6 (2)
C3—C4—C12	117.4 (2)	O5—C27—C32	122.4 (2)
C3—C4—C5	123.4 (2)	C28—C27—C32	116.9 (2)
C12—C4—C5	119.2 (2)	C29—C28—C27	121.4 (2)
C6—C5—C4	121.3 (2)	C29—C28—H28	119.3
C6—C5—H5	119.3	C27—C28—H28	119.3
C4—C5—H5	119.3	C28—C29—C30	121.4 (3)
C5—C6—C7	121.3 (2)	C28—C29—H29	119.3
C5—C6—H6	119.4	C30—C29—H29	119.3
C7—C6—H6	119.4	C31—C30—C29	118.8 (3)
C8—C7—C11	117.0 (2)	C31—C30—H30	120.6
C8—C7—C6	123.8 (2)	C29—C30—H30	120.6
C11—C7—C6	119.2 (2)	C30—C31—C32	121.6 (3)
C9—C8—C7	120.8 (3)	C30—C31—H31	119.2
C9—C8—H8	119.6	C32—C31—H31	119.2
C7—C8—H8	119.6	C31—C32—C27	119.8 (2)
C8—C9—C10	118.2 (3)	C31—C32—C33	118.0 (2)
C8—C9—H9	120.9	C27—C32—C33	122.1 (2)
C10—C9—H9	120.9	O6—C33—C32	128.3 (2)
N2—C10—C9	123.8 (3)	O6—C33—H33	115.8
N2—C10—H10	118.1	C32—C33—H33	115.8
C9—C10—H10	118.1	C1—N1—C12	117.69 (19)
N2—C11—C7	122.0 (2)	C1—N1—Sm1	122.02 (15)
N2—C11—C12	118.3 (2)	C12—N1—Sm1	120.23 (13)
C7—C11—C12	119.8 (2)	C10—N2—C11	118.2 (2)
N1—C12—C4	122.8 (2)	C10—N2—Sm1	120.39 (18)
N1—C12—C11	117.84 (19)	C11—N2—Sm1	121.33 (15)
C4—C12—C11	119.3 (2)	C13—O1—Sm1	140.77 (15)
O1—C13—C14	121.2 (2)	C19—O2—Sm1	131.52 (15)
O1—C13—C18	122.7 (2)	C20—O3—Sm1	137.92 (15)
C14—C13—C18	116.1 (2)	C26—O4—Sm1	131.83 (17)
C15—C14—C13	121.5 (3)	C27—O5—Sm1	142.69 (14)
C15—C14—H14	119.2	C33—O6—Sm1	133.70 (15)
C13—C14—H14	119.2	O1—Sm1—O3	144.74 (6)
C14—C15—C16	121.8 (3)	O1—Sm1—O5	83.60 (6)
C14—C15—H15	119.1	O3—Sm1—O5	113.82 (6)
C16—C15—H15	119.1	O1—Sm1—O4	83.10 (7)
C17—C16—C15	118.6 (3)	O3—Sm1—O4	71.39 (6)
C17—C16—H16	120.7	O5—Sm1—O4	79.16 (6)
C15—C16—H16	120.7	O1—Sm1—O6	135.93 (6)
C16—C17—C18	121.7 (3)	O3—Sm1—O6	79.29 (6)
C16—C17—H17	119.1	O5—Sm1—O6	70.59 (5)
C18—C17—H17	119.1	O4—Sm1—O6	123.98 (6)
C17—C18—C13	120.2 (2)	O1—Sm1—O2	71.36 (5)
C17—C18—C19	116.9 (2)	O3—Sm1—O2	78.04 (6)
C13—C18—C19	122.8 (2)	O5—Sm1—O2	144.28 (5)
O2—C19—C18	128.0 (2)	O4—Sm1—O2	73.03 (6)
O2—C19—H19	116.0	O6—Sm1—O2	144.49 (5)
C18—C19—H19	116.0	O1—Sm1—N2	72.68 (7)
O3—C20—C21	120.7 (2)	O3—Sm1—N2	134.55 (6)
O3—C20—C25	122.8 (2)	O5—Sm1—N2	88.71 (6)
C21—C20—C25	116.6 (2)	O4—Sm1—N2	154.01 (6)
C22—C21—C20	121.5 (3)	O6—Sm1—N2	71.66 (6)
C22—C21—H21	119.3	O2—Sm1—N2	106.85 (6)
C20—C21—H21	119.3	O1—Sm1—N1	107.57 (6)
C21—C22—C23	121.9 (3)	O3—Sm1—N1	77.88 (5)
C21—C22—H22	119.1	O5—Sm1—N1	142.33 (6)
C23—C22—H22	119.1	O4—Sm1—N1	136.83 (6)
C24—C23—C22	118.5 (3)	O6—Sm1—N1	77.30 (6)
C24—C23—H23	120.7	O2—Sm1—N1	71.48 (6)
C22—C23—H23	120.7	N2—Sm1—N1	62.33 (6)
C23—C24—C25	122.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O6ⁱ	0.93	2.46	3.326 (3)	154

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Sm(C₇H₅O₂)₃(C₁₂H₈N₂)]
M_r	693.88
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	24.1921 (9), 14.6474 (6), 17.4681 (7)
β (°)	115.28
V (Å³)	5596.8 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.15
Crystal size (mm)	0.35 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.520, 0.673
No. of measured, independent and observed [I > 2σ(I)] reflections	20817, 5066, 4612
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.017, 0.049, 1.09
No. of reflections	5066
No. of parameters	379
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.32

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

N1—Sm1	2.6398 (18)	O3—Sm1	2.2925 (15)
N2—Sm1	2.602 (2)	O4—Sm1	2.4714 (18)
O1—Sm1	2.2906 (16)	O5—Sm1	2.3025 (15)
O2—Sm1	2.4977 (16)	O6—Sm1	2.4888 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O6ⁱ	0.93	2.46	3.326 (3)	154

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

This work was supported by the Natural Science Foundation of China (31160187).

References

Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsis, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsis, USA. Google Scholar
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Li, G.-Z., Zhang, S.-H., Liu, Z. & Jin, L.-X. (2007). Acta Cryst. E63, m2107. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
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